LipidBank - Eicosanoid

No	Structure	COMMON NAME	NAME	DATA No	INFORMANT	SYMBOL	FORMULA	MOL.WT(ave)	Download	BIOOGICAL ACTIVITY	PHYSICAL AND CHEMICAL PROPERTIES						SPECTRAL DATA					CHROMATOGRAM DATA	SOURCE	CHEMICAL SYNTHESIS	METABOLISM	GENETIC INFORMATION	NOTE	REFERENCES
No	Structure	COMMON NAME	NAME	DATA No	INFORMANT	SYMBOL	FORMULA	MOL.WT(ave)	Download	BIOOGICAL ACTIVITY	MELTING POINT	BOILING POINT	DENSITY	REFRACTIVE INDEX	OPTICAL ROTATION	SOLUBILITY	UV SPECTRA	IR SPECTRA	NMR SPECTRA	MASS SPECTRA	OTHER SPECTRA	CHROMATOGRAM DATA	SOURCE	CHEMICAL SYNTHESIS	METABOLISM	GENETIC INFORMATION	NOTE	REFERENCES
1		PROSTAGLANDIN A1	7-[2(R)-(3(S)-Hydroxy-1(E)-octenyl)-5-oxo-3-cyclopenten-1(R)-yl]heptanoic acid / (8R,12S,13E,15S)-15-Hydroxy-9-oxo-10,13-prostadienoic acid	XPR1000	Shouzo Yamamoto	PGA1	C₂₀H₃₂O₄	336.466		Prostaglandin A1 relaxes uterine muscle and shows hypotensive effects on rat and dog (Ref. 0002).	42-44C (Ref. 1005)				ORD (H₂O, C=0.0040g/ml) : 256(+35.000), 220(-43.000) (Ref. 1101)	ETHANOL, CHLOROFORM (Ref. 1005), METHANOL (Ref. 1101)	l ^E^t^O^H_m_a_x = 217nm(e 11,650) (Ref. 1005)	NUJOL : n 3420, 2740, 2700, 2660, 2600, 1715, 1700, 1585, 1275, 1200,1180, 1020, 720cm^-¹ (Ref. 1005)	¹H-NMR(CDCl₃, TMS) : d, 7.52(dd, 1H), 6.17(dd, 1H), 5.6(m, 2H), 4.1(m, 1H, 15-CH), 3.25(12H) (Ref. 1005)	m/e, 336(M⁺), 318(M-18), 300(M-36), 265(M-71), 247, 219, 190 (Ref. 1005)	ORD(H₂O, C=0.0040g/100ml), 256(+35, 000), 220(-43,000) (Ref. 1101)		Prostaglandin A1 is found in human seminal plasma (Ref. 0001).	(Ref. 1005) [Table 0001]				[0001] / [0002] / [1005] / [1101]
2		PROSTAGLANDIN A2	7-[2(R)-(3(S)-Hydroxy-1(E)-octenyl)-5-oxo-3-cyclopenten-1(R)-yl]-5(Z)-heptenoic acid	XPR1001	Shouzo Yamamoto	PGA2	C₂₀H₃₀O₄	334.450		Antitumor activity of prostaglandin A2 is known (Ref. 0038), and prostaglandin A2 rduces blood pressure (Ref. 0002).					[a]=+140(C=1.15, CHLOROFORM) (Ref. 1042)	ETHANOL, CHLOROFORM, METHANOL, DIETHYLETHER (Ref. 1005)	EtOH: 217 nm (e 9900) (Ref. 1005)	NUJOL : n 3400, 1705, 1580, 1255, 1115, 1070, 1015 cm^-¹ (Ref. 1005)	¹H-NMR(CDCl₃) : d 7.57(dd, 1H, 10-CH), 6.2(dd, 1H, 11-CH), 5.6(m, 2H, 13,14-CH), 5.4 (m, 2H, 5,6-CH), 4.12(1H, m, 12-CH), 3.23(m, 1H), 0.89(t, 3H, 0-CH3) (Ref. 1043). METHYL ESTER : ¹³C-NMR(CDCl3) 210.3, 174.0, 165.0, 135.2, 133.3, 131.0, 130.2, 126.7, 72.4, 52.1, 51.5, 49.6, 37.3, 33.5, 31.8, 27.4, 26.7, 25.1, 24.8, 22.6, 14.0 (Ref. 1044)	m/e 334(M⁺), 316, 190 (Ref. 1005)			Prostaglandin A2 was found in human semen in an amount of about 50 micrograms per ml as measured in combination with prostaglandins A1, B1 and B2 (Ref. 0001).	(Ref. 1042) [Table 0001]	Prostaglandin A2 is produced by non-enzymatic degradation of prostaglandin E2 (Ref. 0039), and human serum has an enzymatic activity to convert prostaglandin E2 to A2 (Ref. 0040).			[0001] / [0002] / [0038] / [0039] / [0040] / [1005] / [1042] / [1043] / [1044]
3		19-HYDROXY-PROSTAGLANDIN A2	7-[2(R)-(3(S),7-Dihydroxy-1(E)-octenyl)-5-oxo-3-cyclopenten-1(R)-yl]-5(Z)-heptenoic acid / 15(S),19-Dihydroxy-9-oxo-8(12),13-trans-prostadienoic acid	XPR1031	Shouzo Yamamoto	19-HYDROXY-PGA2	C₂₀H₃₀O₅	350.449		19-Hydroxy-prostaglandin A2 relaxes uterine myometriuim (Ref. 0082).						DIETHYL ETHER, CHLOROFORM, ETHANOL (Ref. 1104)	l ^E^t^O^H_m_a_x = 217 nm(e 10,000) (Ref. 1104)	5.87, 6.30, 10.3mm (Ref. 1104)	¹H-NMR : d 5.75-5.50(m, 2H,13, 14-CH), 5.50-5.25(m, 2H, 5,6-CH), 1.15(d, 3H, 20-CH) (Ref. 1104)	METHYL ESTER ; m/e 364(M⁺), 246, 328, 315 (Ref. 1104)			The compound is contained in human seminal plasma in a considerable amount (Ref. 0001), but it is attributed presumably to a degradation product of 19-hydroxy-prostagaldnin E2 (Ref. 0094).					[0001] / [0082] / [0094] / [1104]
4		PROSTAGLANDIN B1	7-[2-(3(S)-Hydroxy-1(E)-octenyl)-5-oxo-1-cyclopenten-1-yl]heptanoic acid / (E,S)-15-Hydroxy-9-oxo-8(12),13-prostadienoic acid	XPR1100	Shouzo Yamamoto	PGB1	C₂₀H₃₂O₄	336.466			70-71C (Ref. 1102)						l _m_a_x = 278nm(e 28,650) (Ref. 1103)	5.91, 6.10, 6.27, 10.3mm (Ref. 1104)	¹H-NMR :d 6.87(d, J=16Hz, 1H, 13-CH), 6.25(d,d, J=16.6Hz, 1H, 14-CH), 4.38(1H, 15-CH) (Ref. 1105)	METHYL ESTER ; m/e 350(M⁺), 332, 319, 301, 251, 219 (Ref. 1106)			Prostaglandin B1 is found in human seminal plasma (Ref. 0001).	(Ref. 1105) [Table 0001]				[0001] / [1102] / [1103] / [1104] / [1105] / [1106]
5		PROSTAGLANDIN B2	7-[2-(3(S)-Hydroxy-1(E)-octenyl)-5-oxo-1-cyclopenten-1-yl]-5(Z)-heptenoic acid	XPR1101	Shouzo Yamamoto	PGB2	C₂₀H₃₀O₄	334.450									MeOH: 278 nm (e 26000) (Ref. 1045)		METHYL ESTER ; ¹H-NMR : d 6.9(d, J=16Hz, 1H, 13-CH), 6.3(dd, J=5.5, 16Hz, 1H,14-CH), 5.7-5.1(m, 2H), 4.5-4.1(m, 1H, 15-CH), 3.65(S, 3H, OCH3), 3.15-2.85(m, 2H, 7-CH) (Ref. 1046)	METHYL ESTER; m/e 348(M⁺), 317, 249, 247, 245, 217, 215, 133, 119, 109 (Ref. 1046)			Prostaglandin B2 was found in human seminal plasma in an amout of 50 micrograms per ml as measured in combination with prostaglandins A1,A2 and B1 (Ref. 0001).		Prostaglandin E2 is converted to prostaglandin B2 non-enzymatically at alkaline condition (Ref. 0039). Huma serum contains a dehydrase converting prostaglandin E2 to A2, an isomerase converting prostaglandin A2 to C2, and another isomerase converting prostaglandin C2 to B2 (Ref. 0040).			[0001] / [0039] / [0040] / [1045] / [1046]
6		19-HYDROXY-PROSTAGLANDIN B2	7-[2-(3(S),7-Dihydroxy-1(E)-octenyl)-5-oxo-1-cyclopenten-1-yl]-5(Z)-heptenoic acid / 15(S),19-Dihydroxy-9-oxo-5-cis-8(12),13-trans-prostatrienoic acid	XPR1131	Shouzo Yamamoto	19-HYDROXY-PGB2	C₂₀H₃₀O₅	350.449		19-Hydroxy-prostaglandin B2 relaxes uterine myometriuim (Ref. 0082).						ETHANOL (Ref. 1104)	l ^E^t^O^H_m_a_x = 278 nm(e 20,000) (Ref. 1104)	5.92, 6.09, 6.26, 10.3mm (Ref. 1104)					The compound is contained in human seminal plasma in a considerable amount (Ref. 0001), but it is attributed presumably to a degradation product of 19-hydroxy-prostagaldnin E2 (Ref. 0094).					[0001] / [0082] / [0094] / [1104]
7		PROSTAGLANDIN C2	7-[2-(3(S)-Hydroxy-1(E)-octenyl)-5-oxo-2-cyclopenten-1(R)-yl]-5(Z)-heptenoic acid	XPR1201	Shouzo Yamamoto	PGC2	C₂₀H₃₀O₄	334.450								METHANOL, CHLOROFORM (Ref. 1047)	l ^M^e^O^H_m_a_x = 234 nm (e 17000) (Ref. 1047)	CHLOROFORM solution, n 1750,1715 cm^-¹ (Ref. 1047)	METHYL ESTER ; d 6.3(d, J=16Hz, 1H, 13-CH), 6.1-5.95(m, 2H, 11-CH), 5,7(dd, J=6,16Hz, 1H, 14-CH), 5.7-5.1(m, 2H, 5,6-CH), 4.4-4.0(m, 1H, 15-CH), 3.69(S, 3H, OCH₃), 3.3-3.0(m, 1H,8-CH), 3.0-2.8(m, 2H, 10-CH) (Ref. 1046)	METHYL ESTER; m/e 348(M⁺), 330, 249, 245, 217, 215, 190, 133, 119, 109 (Ref. 1046)				(Ref. 1047) [Table 0001]	Prostaglandin A isomerase converts prostaglandin A2 to C2, and the enzyme is found in human serum (Ref. 0040) and in the plasma of rabbit, cat, pig, dog and rat (Ref. 0041).			[0040] / [0041] / [1046] / [1047]
8		PROSTAGLANDIN D2	7-[5(S)-Hydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)-3-oxocyclopentan-1(R)-yl]-5(Z)-heptenoic acid	XPR1301	Shouzo Yamamoto	PGD2	C₂₀H₃₂O₅	352.465		Biological significance of prostaglandin D2 was unknown except anti-aggregatory and bronchoconstrictive activities (Ref. 0009). Recently prostaglandin D2 has been noted as antineoplastic agent (actually attributed to D12-prostaglandin J2) (Ref. 0010/0011) and as a sleep-inducing compound (Ref. 0012). Prostaglandin D2 binds to a receptor with 7 transmembrane domains (DP) coupled to a Gs protein (Ref. 0003).	68C (Ref. 1010)				[a]=9 (C=2.11,THF) (Ref. 1012)	ETHYL ACETATE,THF,CHLOROFORM (Ref. 1012)		KBr : 3400-2500, 1740, 1700, 975cm^-¹ (Ref. 1010)	¹H-NMR(270MHz, CDCl₃) : d 5.63(dd,J=7 & 16Hz,1H,14-CH), 5.43(dd,J=16 & 8.5Hz,1H,13-CH), 4.47(m, 1H, 9-CH), 4.09(bq, J=7Hz, 1H, 15-CH), 2.87(dd, J=12 & 8.5Hz, 1H, 12-CH), 2.45(m, 2H, 10-CH2), 1.95(bm, 1H, 8-CH) (Ref. 1011)	m/e 334, 316, 246, 245, 191, 190, 161, 55 (Ref. 1012)			In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin D2. Prostaglandin D2 is produced in barin, lung, spleen, mast cells and other tissues (Ref. 0005).	(Ref. 1010) [Table 0001]	Prostaglandin D2 is produced by isomerization of 9,11-endoperoxide of prostaglandin H2. There are two isozymes of prostaglandin D synthase (hematopoietic type and lipocalin type) distinguished by glutathione reequirement and effect of inhibitor (Ref. 0005). Prostaglandin D2 is either reduced to 9a,11b-prostaglandin F or oxidized to 15-keto-prostaglandin D2 by a specific dehydrogenase (Ref. 0009). Non-enzymatic transformation of prostaglandin D2 produces anti-neoplastic D12-prostaglandin J2 (Ref. 0011).	cDNA and genomic DNA of prostaglandin D synthase were cloned (Ref. 0005). cDNA for DP was isolated (Ref. 0011).		[0003] / [0005] / [0009] / [0010] / [0011] / [0012] / [1010] / [1011] / [1012]
9		PROSTAGLANDIN E1	7-[3(R)-Hydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)-5-oxocyclopentan-1(R)-yl]-heptanoic acid / (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid	XPR1400	Shouzo Yamamoto	PGE1	C₂₀H₃₄O₅	354.481		Prostaglandin E1 is generally considered as active as E2, and the biological activities of both compounds are compared in references (Ref. 0002/0088). However, platelet aggregation is inhibited by prostaglandin E1 whereas prostaglandin E2 is much less active (Ref. 0002).	115-117C (Ref. 1107)				[a]₅₇₈=-61.6(C=0.56, TETRAHYDROFURAN) (Ref. 1108)	DIETHYL ETHER, ETHYL ACETATE (Ref. 1107), METHANOL (Ref. 1106), TETRAHYDROFURAN (Ref. 1108)		METHYL ESTER ; n 1726, 1717sh, 1699, 980 cm^-¹ (Ref. 1109)	¹H-NMR(CDCl₃+DMSO-d₆,TMS) : d 5.70-5.51(m, 2H), 4.14-3.86(m, 2H), 2.72(d,d, 1H)(Ref. 1109). ¹³C-NMR(CHCl₃-CH₃OH, TMS) : d 215.2(C-9), 176.7(C-1), 136.6(C-14), 131.9(C-13), 72.9(C-15), 71.6(C-11), 54.6(C-8), 54.2(C-12), 45.9(C-10), 36.9(C-16), 33.8(C-2), 31.5(C-18), 29.0(C-4), 28.6(C-5), 27.4(C-7), 26.3(C-6), 25.0(C-17), 24.5(C-3), 22.5(C-19), 13.8(C-20) (Ref. 1008)	METHYL ESTER ; m/e 350, 332, 319, 301, 279 (Ref. 1104)			Prostaglandin E1 is contained in human seminal plasma in an amount of 25 microgram/ml (Ref. 0001), and has been found in ovine seminal plasma and seminal vesicle, human menstrual and amniotic flluid, human uterine endometrium, umbilical cord, placental vessels and decidua, frog spinal cord, rat adrenal, human and bovine thymus, frog intestine, rat fat tissue, and human phrenic nerve (Ref. 0082/0083/0084/0085/0086/0087).	(Ref. 1108) [Table 0001]	Prostagalndin E1 is produced from H1 at almost the same rate of E2 synthesis from H2 by an enzyme of bovine seminal vesicle (Ref. 0089).			[0001] / [0002] / [0082] / [0083] / [0084] / [0085] / [0086] / [0087] / [0088] / [0089] / [1008] / [1104] / [1106] / [1107] / [1108] / [1109]
10		Prostaglandin E2	7-[3(R)-Hydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl-5-oxocyclopentan-1(R)-yl]-5(Z)-heptenoic acid	XPR1401	Shouzo Yamamoto	PGE2	C₂₀H₃₂O₅	352.465		Prostaglandin E2 exhibits various biological activities such as vasodilatation, uterine contraction, gastrointestinal contraction, bronchodilatation, diuresis, pyrexia, inhibition of gastric secretion, bone resorption and immunosuppression (Ref. 0002). Prostaglandin E2 is a ligand to receptors present in the cell membrane, and there are at least 4 subtypes of its receptor. Different tissue distributions and signal transductions of these receptor subtypes explain a variety of biological activities of prostaglandin E2 (Ref. 0003).	65-66C (Ref. 1001)				[a]=-61.0(C=1.0, TETRAHYDROFURAN) (Ref. 1001)	ETHYL ACETATE,THF,CHLOROFORM(Ref. 1002/1006). STABILITIES: to be stable under neutral condition. to decompose to PGA2 under acidic and to PGB2 under basic conditions (Ref. 1004/1005)		d,l-mixture ; 3400, 1710, 970cm^-¹ (Ref. 1003)	¹³C-NMR(CDCl₃) : 214.71(C9),178.39(C1), 136.62(C14), 131.52(C13), 130.91(C5), 126.69(C6), 73.19(C15), 72.13(C11), 54.55(C12), 53.51(C8), 46.23(C10), 37.00 (C16), 33.56(C2), 31.73(C18), 26.47(C4), 25.20(C7,17), 24.60(C3), 22.64(C19), 14.04. (Ref. 1002). ¹H-NMR(CDCl₃) : d5.67(dd, J=6.6Hz, 15.4, 1H, 14-CH), 5.57(dd, J=8.1, 15.4Hz, 1H, 13-CH), 5.40(m, 2H, 5.6-CH), 4.12(q, J=6.5, 6.7, 6.8Hz, 1H, 15-CH), 4.06(q, J=8.1, 8.2, 8.3Hz, 1H, 11-CH), 2.72(dd, J= (Ref. 1002)	d,l-mixture ; 334(M⁺-18), 316, 298, 190 (Ref. 1003)			Prostaglandin E2 was found to be accummulating in human semen in an amount of about 13 microgram per ml (Ref. 0001). In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin E2.	[Table 0001] (Ref. 1001)	Prostaglandin E2 is produced from arachidonic acid via prostaglandins G2 and H2 by the catalyses of prostaglandin endoperoxide synthase (cyclooxygenase) (Ref. 0004) and prostaglandin E synthase (Ref. 0005). Two isoforms of the cyclooxygnease enzyme responsible for prostaglandin H2 synthesis are present. Cyclooxygenase-1 is constitutively found in most mammalian tissues, while cyclooxygnease-2 is induced rapidly and transiently in physiological and pathological events, especially in inflammation (Ref. 0004). The biological activities of prostaglandin E2 are lost by oxidation of its 15-hydroxyl group catalyzed by 15-hydroxyprostaglandin dehydrogenase (Ref. 0006).	cDNAs of the two cyclooxygenase isozymes responsible for prostaglandin H2 synthesis have been cloned, and the primary structures of these enzymes were deduced from the nucleotide seuences (Ref. 0007/0008). Their genomic DNA were also cloned, and the genomic structure were eludicated (Ref. 0007). cDNAs of four subtypes of prostaglandin E2 receptors (EP1-4) were cloned, and the 7-transmembrane domain structures of the receptors coupled with certain G proteins were reported (Ref. 0003).		[0001] / [0002] / [0003] / [0004] / [0005] / [0006] / [0007] / [0008] / [1001] / [1002] / [1003] / [1004] / [1005] / [1006]
11		PROSTAGLANDIN E3	7-[3(R)-Hydroxy-2(R)-(3(S)-hydroxyocta-1(E),5(Z)-dienyl)-5-oxocyclopentan-1(R)-yl]-5(Z)-heptenoic acid / (5Z,8R,11R,12R,13E,15S,17Z)-11,15-Dihydroxy-9-oxo-5,13,17-prostatrienoic acid	XPR1402	Shouzo Yamamoto	PGE3	C₂₀H₃₀O₅	350.449		As presented in Table 1 of reference (Ref. 0002), prostaglandin E3 is 1/10-1/2 as active as prostaglandin E2.	84.5-85.5C (Ref. 1113)				[a]=-48.9(C=1.2, TETRAHYDROFURAN) (Ref. 1114)	TETRAHYDROFURAN (Ref. 1114)			METHYL ESTER ; ¹H-NMR(CDCl₃) : d 5.8-5.5(m, 2H,13, 14-CH), 5.5-5.2(m, 4H, 5,6,17,18-CH), 4.4-3.8(m, 2H, 11,15-CH), 0.95(t, 3H, 20-CH) (Ref. 1115)	METHYL ESTER ; m/e 346(M-18), 328(M-18x2), 315, 297, 277, 259, 188 (Ref. 1116)			Prostaglandin E3 is contained in human seminal plasma in an amount of 5.5 micrograms/ml (Ref. 0001), and also found in ovine seminal vesicle and plasma (Ref. 0083).	(Ref. 1114) [Table 0001]				[0001] / [0002] / [0083] / [1113] / [1114] / [1115] / [1116]
12		15-KETOPROSTAGLANDIN E2	7-[3(R)-Hydroxy-2(R)-(3-oxo-1(E)-octenyl)-5-oxocyclopentan-1(R)-yl]-5(Z)-heptenoic acid	XPR1411	Shouzo Yamamoto	15-KETO-PGE2	C₂₀H₃₀O₅	350.449		It is well known that the biological activities of various prostaglandins are reduced upon their dehydrogenation at carbon-15 by the catalysis of 15-hydroxyprostaglandin dehydrogenase (Ref. 0044).							METHYL ESTER ; l ^M^e^O^H_m_a_x = 227nm (e 9000) (Ref. 1055)			DIMETHOXIME TMS ETHER METHYL ESTER ; m/z 494(M⁺), 479, 463, 404, 373, 321, 180 (Ref. 1055)			15-Keto-prostaglandin E2 is the oxidized product of prostaglandin E2 by 15-hydroxyprostaglandin dehydrogenase, which is present in lung, kidney, placenta and other tissues and catalyzes the NAD- or NADP-dependent dehydrogenation of 15-hydroxyl group (Ref. 0006).		15-Keto-prostaglandin E2 is further metabolized by its D13-reduction, b-oxidation and w oxidation. The ultimate metabolite is (7a-hydroxy-5,11-diketotetranorprosta-1,16-dioic acid) and excreted in urine (Ref. 0045).	cDNA for placental 15-hydroxyprostaglandin dehydrogenase was cloned (Ref. 0046).		[0006] / [0044] / [0045] / [0046] / [1055]
13		PROSTAGLANDIN E-MAJOR URINARY METABOLITE	8-[2(R)-(2-Carboxyethyl)-5(R)-hydroxy-3-oxocyclopentan-1(R)-yl]-6-oxooctanoic acid	XPR1421	Shouzo Yamamoto	PGE-MUM	C₁₆H₂₄O₇	328.358								ETHYL ACETATE (Ref. 1061)				DIMETHYL ESTER DI-O-METHYLOXIME TMS ETHER DERIVATIVE ; m/e 486, 455, 369, 365, 355, 286, 279, 268, 265, 196, 115 (Ref. 1061)			When prostaglandin E2 or E1 was administered intravenously to man, 7a-hydroxy-5,11-diketo-tetranor-prosta-1,16-dioic acid was found as a major urinary metabolite (PGE-MUM) (Ref. 0045).					[0045] / [1061]
14		6-KETO-PROSTAGLANDIN E1	7-[3(R)-Hydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)-5-oxocyclopentan-1(R)-yl]-6-oxoheptanoic acid	XPR1430	Shouzo Yamamoto	6-KETO-PGE1	C₂₀H₃₂O₆	368.464		6-Keto-prostaglandin E1 is a stable metabolite. The compound inhibits platelet aggregation with activity comparable or greater than prostaglandin D2 although less potent than prostaglandin I2. Its vasodilatory and hypotensive activities, bronchodilatory property, and inhibition of gastric acid secretion were reported (Ref. 0054).	65C (Ref. 1053)				[a]=-50(C=1.55, METHANOL) (Ref. 1053)	METHANOL, CHLOROFORM (Ref. 1053)		KBr: n 3400, 1740, 1720, 1710, 1245, 1160, 1075, 970 cm^-¹ (Ref. 1053)	¹H-NMR(CDCl₃) : d 5.58(m, 2H, 13,14-CH), 4.09(m, 1H, 11-CH), 4.02(m, 1H, 15-CH), 2.7(2H, 7-CH), 2.69(IH, 10b-CH), 2.45-2.47(m, 3H, 5,8,12-CH), 2.29(1H, 10a-CH), 2.28(2H, 2-CH), 1.58 - 1.32(12H), 0.91(t, 3H, 20-CH₃) (Ref. 1069). METHYL ESTER ; ¹³C-NMR(CDCl₃) : 216.6, 208.4, 173.8, 138.0, 126.5, 72.3, 51.5, 44.6, 45.7, 42.4, 37.6, 33.8, 31.8, 25.2, 24.5, 23.4, 22.6, 14.0 (Ref. 1053)	DIRECT EXPOSURE AMMONIA CI, POSITIVE : 386(M⁺+18), 368(M+), 351, 350, 244, 136. NEGATIVE : 368(M⁺) ,350, 338, 332 (Ref. 1054)			There were reports of prolonged biological activity of chemically unstable prostaglandin I2, which suggested a possible transformation of prostaglandin I2 to a more stable metabolite with potent bioactivity (Ref. 0053). Futher investigations led to the discovery of 6-keto-prostaglandin E1.	(Ref. 1053) [Table 0001]	A potential role of 9-hydroxyprostaglandin dehydrogenase was demonstrated in the transformation of prostaglandin I2 to 6-keto-prostaglandin E1 (Ref. 0053).			[0053] / [0054] / [1053] / [1054] / [1069]
15		PROSTAGLANDIN F1a	7-[3(R),5(S)-Dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)cyclopentan-1(R)-yl]-heptanoic acid / (8R,9S,11R,13E,15S)-9,11,15-Trihydroxyprost-13-enoic acid	XPR1500	Shouzo Yamamoto	PGF1a	C₂₀H₃₆O₅	356.497		In terms of contraction of gastrointestinal smooth muscles, prostaglandin F1a was repoprted to be about 10 times less active than prostaglandin F2a (Ref. 0082). Reference (Ref. 0002) contains a table for comparison of biological activities of various prostaglandins including F1a.	102-103C (Ref. 1110)				[a]=+30(ETHANOL) (Ref. 1005)	DIETHYL ETHER, ETHYL ACETATE, METHANOL (Ref. 1110), ETHANOL (Ref. 1005)		d,l-PGF1a ; KBr : n 3330, 1716, 967 cm^-¹ (Ref. 1111)	¹H-NMR(ACETONE-d₆, TMS) : d 5.50(2H, 13-,14-CH), 3.75-4.3(m, 3H), 0.88(t, 3H) (Ref. 1102)¹H-NMR(CD₃OD, TMS, 300MHz):d4.10(1H, 9-CH), 3.81(1H, 11-CH), 2.36(1H, 10b-CH), 1.57(1H, 10a-CH)(Ref. 1112)	m/e 356(M⁺), 338, 320 (Ref. 1102)			Prostaglandin F1a is contained in human seminal plasma in an amount of 3.6 microgram/ml (Ref. 0001), and is detected in ovine seminal plasma and seminal vesicle, human amniotic fluid, umbilical cord, placental vessels and decidua, frog spinal cord and intestine, and rat adrenal (Ref. 0084).	(Ref. 1111) [Table 0001]				[0001] / [0002] / [0082] / [0084] / [1005] / [1102] / [1110] / [1111] / [1112]
16		PROSTAGLANDIN F2a	7-[3(R),5(S)-Dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenylcyclopentan-1(R)-yl]-5(Z)-heptenoic acid	XPR1501	Shouzo Yamamoto	PGF2a	C₂₀H₃₄O₅	354.481		Prostaglandin F2a exhibits various biological activities such as uterine contraction, gastrointestinal contraction, bronchoconstriction, luteolysis and vasoconstriction (Ref. 0002). Prostaglandin F2a is a ligand to a receptor (FP) present in the cell membrane (Ref. 0003).	25-35C (Ref. 1007)				[a]=23.8 (C=1,THF) (Ref. 1001)	ETHYL ACETATE, ACETONE, DIETHYLETHER (Ref. 1005). STABILITIES: to be stable under neutral and basic conditions (Ref. 1004)		NEAT : 3320, 2640, 1710, 1295, 1260, 1245, 1120, 1080, 1055, 1025, 975cm^-¹ (Ref. 1005)	¹H-NMR(d₆-ACETONE) : d 5.48(m, 4H), 4.05(m, 3H), 0.9(t, 3H, 20-CH3) (Ref. 1005). ¹³C-NMR : 176.6(C1), 135.0(C14), 132.8(C5), 129.1(C13 or C6), 128.9(C6 or C13), 77.2(C11), 72.9(C15), 71.8(C9), 55.0(C12), 49.9(C8), 42,6(C10), 36.8(C16), 33.2(C2), 31,5(C18), 26.3(C4), 25.1(C7), 25.1(C17), 24.5 (Ref. 1008)	354(M⁺), 336, 318, 292, 274, 264(100), 247, 229, 191, 177, 165, 137, 99, 81, 67 (Ref. 1009)			Prostaglandin F2a was found to be accummulating in human semen in an amount of about 2 microgram per ml (Ref. 0001). In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin F2a.	(Ref. 1001) [Table 0001]	Prostaglandin F synthase reduces 9,11-endoperoxide of prostaglandin H2 requiring NADPH, and produces prostaglandin F2a. The same enzyme also reduces 9-keto group of prostaglandin D2 producing 11b-prostaglandin F2 (Ref. 0005).	cDNA for prostaglandin F synthase was cloned from bovine lung (Ref. 0005). cDNA for prostaglandin F2a receptor (FP) was cloned, and its 7ptransmembrane structure was reported (Ref. 0003).		[0001] / [0002] / [0003] / [0005] / [1001] / [1004] / [1005] / [1007] / [1008] / [1009]
17		PROSTAGLANDIN F3a	7-[3(R),5(S)-Dihydroxy-2(R)-(3(S)-hydroxyocta-1(E),5(Z)-dienyl)cyclopentan-1(R)-yl]-5(Z)-heptenoic acid / (5Z,8R,9S,11R,12R,13E,15S,17Z)-9,11,15-Trihydroxyprosta-5,13,17-trienoic acid	XPR1502	Shouzo Yamamoto	PGF3a	C₂₀H₃₂O₅	352.465							[a]=+29.6(C=0.54, TETRAHYDROFURAN) (Ref. 1114)	TETRAHYDROFURAN (Ref. 1114)				TRI-TMS ETHER, METHYL ESTER ; AMMONIA CI : m/e, 600(M⁺18), 585, 583(M⁺1), 510, 493, 420, 403 (Ref. 1117)			Prostaglandin F3a is found in bovine lung (Ref. 0083).	(Ref. 1114) [Table 0001]				[0083] / [1114] / [1117]
18		15-KETOPROSTAGLANDIN F2a	7-[3(R),5(S)-Dihydroxy-2(R)-(3-oxo-1(E)-octenyl)cyclopentan-1(R)-yl]-5(Z)-heptenoic acid	XPR1511	Shouzo Yamamoto	15-KETO-PGF2a	C₂₀H₃₂O₅	352.465		It is well known that the biological activities of various prostaglandins are reduced upon their dehydrogenation at carbon-15 by the catalysis of 15-hydroxyprostaglandin dehydrogenase (Ref. 0044).													15-Keto-prostaglandin F2a is the oxidized product of prostaglandin F2a by 15-hydroxyprostaglandin dehydrogenase, which is present in lung, kidney, placenta and other tissues and catalyzes the NAD- or NADP-dependent dehydrogenation of 15-dydroxyl group (Ref. 0006).		15-Keto-prostaglandin F2a is further metabolized by its D13-reduction, b-oxidation and w oxidation. The ultimate metabolite is 5a,7a-dihydroxy-11-keto-tetranorprosta-1,16-dioic acid, and excreted in urine (Ref. 0047).	cDNA for placental 15-hydroxyprostaglandin dehydrogenase was cloned (Ref. 0046).		[0006] / [0044] / [0046] / [0047]
19		PROSTAGLANDIN Fa-MAJOR URINARY METABOLITE	8-[2(R)-(2-Carboxyethyl)-3(S),5(R)-dihydroxycyclopentan-1(R)-yl]-6-oxooctanoic acid	XPR1521	Shouzo Yamamoto	PGFa-MUM	C₁₆H₂₆O₇	330.373												DIMETHYL ESTER DI-TMS ETHER ; m/e 502(M⁺), 487, 412, 397, 325, 322, 291, 254, 241, 228, 217, 191, 179, 143 (Ref. 1062)			When prostaglandin F2a was administered intravenously to female subjects, 5a,7a-dihydroxy-11-keto-tetranor-prosta-1,16-dioic acid was found as a major urinary metabolite (PGFa-MUM) (Ref. 0047).					[0047] / [1062]
20		PROSTAGLANDIN G2	7-[2(R)-(3(S)-Hydroperoxy-1(E)-octenyl)-1(R),4(S)-5,6-dioxabicyclo[2.2.1]-heptan-3(R)-yl]-5(Z)-heptenoic acid	XPR1601	Shouzo Yamamoto	PGG2	C₂₀H₃₂O₆	368.464		Prostaglandin G2 is a metabolic intermediate, but the compound as such has biological activities of bronchoconstriction and vasoconstriction (Ref. 0013/0020).									¹³C-NMR : d 84.6(C15) (Ref. 1016)				Prostaglandin G2 is produced by bis-dioxygenation and cyclization of arachidonic acid as an intermediate for the biosyntheses of various prostaglandins and thromboxanes. The responsible enzyme is prostaglandin endoperoxide synthase usually referred to as fatty acid cyclooxygenase, and distributed in various animal tissues (Ref. 0015/0019).	(Ref. 1016) [Table 0001]	Prostaglandin endoperoxide synthase is a bifunctional enzyme with an oxygenase activity (fatty acid cyclooxygenase) producing prostaglandin G2 from arachidonic acid and a peroxidase activity (prostagladnin hydroperoxidase) converting prostaglandin G2 to prostaglandin H2 (Ref. 0019). The enzyme is usually referred to briefly as cyclooxygenase. There are two isozymes of the enzyme. Cyclooxygenase-1 is a constitutive enzyme expressed in most mammalian cells, while cyclooxygenase-2 is a product of immediate early gene and is induced rapidly and transiently in certain types of cell by various bioactive compounds (Ref. 0004/0008).	cDNA and genomic DNA each for cyclooxygenas-1 and 2 were cloned (Ref. 0007).	Stability:unstable in water around neutrality with a half life of about 5 min at 37C and decomposes to PGE2, PGD2, PGF2 and 12L-hydroxy-5,8,10-heptadecatrienoic acid(Ref. 0068).	[0004] / [0007] / [0008] / [0013] / [0015] / [0019] / [0020] / [0068] / [1016]
21		PROSTAGALANDIN H2	7-[2(R)-(3(S)-Hydroxy-1(E)-octenyl)-1(R),4(S)-5,6-dioxabicyclo[2.2.1]heptan-3(R)-yl]-5(Z)-heptenoic acid	XPR1701	Shouzo Yamamoto	PGH2	C₂₀H₃₂O₅	352.465		Prostaglandin H2 is a metabolic intermediate, but the compound as such is bioactive to aggregate platelets and to contract artery (Ref. 0013/0020).						CHLOROFORM, METHYLENE CHLORIDE, ETHYL ACETATE (Ref. 1018/1019)		METHYL ESTER:to be cited the Chart(Ref. 1018)	¹H-NMR :to be cited the Chart(Ref. 1018). ¹³C-NMR(CD₂Cl₂) : 178.5(C1), 133.5, 130.4, 130,0, 128.4, 82.1, 79.6(C9 & C11), 72.7(C15), 50.4, 48.2, 42.4, 37.0, 33.1, 31.7, 26.9, 26.3, 25.1, 24.5, 22.7, 14.0 (Ref. 1019)	15-TRIMETHYLSILYL ETHER METHYL ETHER :to be cited the Chart(Ref. 1020)			Prostaglandin H2 is produced by 15-hydroperoxide reduction of prostaglandin G2 as an intermediate for the biosyntheses of various prostaglandins and thromboxanes. The responsible enzyme is prostaglandin endoperoxide synthase usually referred to as fatty acid cyclooxygenase, and distributed in various animal tissues (Ref. 0015/0019).	(Ref. 1019) [Table 0001]	Prostaglandin endoperoxide synthase is a bifunctional enzyme with an oxygenase activity (fatty acid cyclooxygenase) producing prostaglandin G2 from arachidonic acid and a peroxidase activity (prostagladnin hydroperoxidase) converting prostaglandin G2 to prostaglandin H2 (Ref. 0019). The enzyme is usually referred to briefly as cyclooxygenase. There are two isozymes of the enzyme. Cyclooxygenase-1 is a constitutive enzyme expressed in most mammalian cells, while cyclooxygenase-2 is a product of immediate early gene and is induced rapidly and transiently in certain types of cell by various bioactive compounds (Ref. 0004/0008).	cDNA and genomic DNA each for cyclooxygenase-1 and 2 were cloned (Ref. 0007).	Stability:unstable in water around neutrality with a half life of about 5 min at 37C and decomposes to PGE2, PGD2, PGF2 and 12L-hydroxy-5,8,10-heptadecatrienoic acid(Ref. 0068).	[0004] / [0007] / [0008] / [0013] / [0015] / [0019] / [0020] / [0068] / [1018] / [1019] / [1020]
22		Prostaglandin A3	9-oxo-15S-hydroxy-prosta-5Z,10,13E,17Z-tetraen-1-oic acid	XPR1702	Takehiko Yokomizo		C₂₀H₂₈O₄	332.434															PGA3 is non-enzymatic dehydration product of PGE3.
23		Prostaglandin B3	9-oxo-15S-hydroxy-prosta-5Z,8(12),13E,17Z-tetraen-1-oic acid	XPR1703	Takehiko Yokomizo		C₂₀H₂₈O₄	332.434															PGB3 is a non-enzymatic dehydration product resulting from the treatment of PGE3 with strong base.
24		13,14-dihydro-15keto Prostaglandin D2	9a-hydroxy-11,15-dioxo-prost-5Z-en-1-oic acid	XPR1704	Takehiko Yokomizo		C₂₀H₃₂O₅	352.465															13,14-dihydro-15keto PGD2 is a metabolite of PGD2 which is formed through the PG 15-dehydrogenase pathway.(Ref. 2003)					[2003]
25		Prostaglandin D3	9a,15S-dihydroxy-11-oxo-prosta-5Z,13E,17Z-trien-1-oic acid	XPR1705	Takehiko Yokomizo		C₂₀H₃₀O₅	350.449		PGD3 has almost same ability to decrease systemic blood pressure in rats and to decrease intraocular pressure in rabbits.(Ref. 2005/2006/2007) However, it is 3 to 5 times more potent than PGD2 in the inhibition of ADP-induced human platelet aggregation.<<													PGD3 is produced by the metabolism of EPA via the cyclooxygenase pathway.(Ref. 2004)					[0004] / [0008] / [0019] / [2004] / [2005] / [2006] / [2007]
26		D¹⁷-Prostaglandin E1	9-oxo-11a,15S-dihydroxy-prosta-13E,17Z-dien-1-oic acid	XPR1706	Takehiko Yokomizo		C₂₀H₃₂O₅	352.465		D¹⁷-PGE1 is about half as potent as PGE1 as an inhibitor of ADP-induced aggregation of rabbbit PRP.(Ref. 2008) In humanPRP, D¹⁷-PGE1 is a more potent antiplatelet agonist than PGE1.													D¹⁷-PGE1 is produced by the cyclooxigenase metabolism of w-3 arachidonic acid.					[2008]
27		13,14-dihydro Prostaglandin E1	9-oxo-11a,15S-dihydroxy-prostan-1-oic acid	XPR1707	Takehiko Yokomizo		C₂₀H₃₆O₅	356.497		13,14-dihydro PGE1 is an inhibitor of ADP-induced platelet aggregation in human PRP.
28		13,14-dihydro-15keto Prostaglandin E1	9,15-dioxo-11a-hydroxy-prostan-1-oic acid	XPR1708	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		13,14-dihydro-15keto PGE1 is a week inhibitor of ADP-induced platelet aggregation in human PRP.													13,14-dihydro-15keto PGE1 is a metabolite of PGE1.(Ref. 2010/2011)					[2010] / [2011]
29		15-keto Prostaglandin E1	9,15-dioxo-11a-hydroxy-prost-13E-en-1-oic acid	XPR1709	Takehiko Yokomizo		C₂₀H₃₂O₅	352.465		15-keto PGE1 has very slight biological activity compared to PGE1.(Ref. 2013)													15-keto PGE1 is the inactive metabolite of PGE1 via PG15-dehydrogenase					[2013]
30		19(R)-hydroxy Prostaglandin E1	9-oxo-11a,15S,19R-trihydroxy-prost-13E-en-1-oic acid	XPR1710	Takehiko Yokomizo		C₂₀H₃₄O₆	370.480		19(R)-hydroxy PGE1 has contractile activity on smooth muscle preparations.(Ref. 2014/2015)													19(R)-hydroxy PGE1 is the major prostaglandin found in the semen of primates.					[2014] / [2015]
31		5-trans Prostaglandin E2	9-oxo-11a,15S-dihydroxy-prosta-5E,13E-dien-1-oic acid	XPR1711	Takehiko Yokomizo		C₂₀H₃₂O₅	352.465		5-trans PGE2 has 18 times potency in activating adenylate cyclase compared to PGE2.(Ref. 2017) 5-trans PGE2 accelerates fibrinolysis by enhancing plasminogen activation mediated dby tissue-type plasminogen activator.(Ref. 2018) And it also inhibits platelet													5-trans PGE2 is naturally produced by some gorgonian corals and is also a common impurity in commercial lots of PGE1.					[2017] / [2018]
32		13,14-dihydro-15keto Prostaglandin E2	9,15-dioxo-11a-hydroxy-prost-5Z-en-1-oic acid	XPR1712	Takehiko Yokomizo		C₂₀H₃₂O₅	352.465															13,14-dihydro-15keto PGE2 is the primary metabolite of PGE2 in plasma via PG 15-dehydrogenase.(Ref. 2010)					[2010]
33		19(R)-hydroxy Prostaglandin E2	9-oxo-11a,15S,19R-trihydroxy-prosta-5Z,13E-dien-1-oic acid	XPR1713	Takehiko Yokomizo		C₂₀H₃₂O₆	368.464		19(R)-hydroxy PGE2 is a potent smooth muscle relaxant and a selective agonist for the EP2 receptor.(Ref. 2014/2015)																		[2014] / [2015]
34		20-hydroxy Prostaglandin E2	9-oxo-11a,15S,20-trihydroxy-prosta-5Z,13E-dien-1-oic acid	XPR1714	Takehiko Yokomizo		C₂₀H₃₂O₆	368.464															20-hydroxy PGE2 is a product of cytochrome P450 metabolism of PGE2.(Ref. 2019/2020)					[2019] / [2020]
35		6,15-diketo-13,14-dihydro Prostaglandin F1a	6,15-dioxo-9a,11a-dihydroxy-prostan-1-oic acid	XPR1715	Takehiko Yokomizo		C₂₀H₃₄O₆	370.480		6,15-diketo-13,14-dihydro PGF1a is hown to enhance the intracellular cAMP and cholesterol catabolism in bovine arterial smooth muscle cells.(Ref. 2021)																		[2021]
36		D¹⁷-6-keto Prostaglandin F1a	6-oxo-9a,11a,15S-trihydroxy-prosta-13E,17Z-dien-1-oic acid	XPR1716	Takehiko Yokomizo		C₂₀H₃₂O₆	368.464															D¹⁷-6-keto PGF1a is no enzymatic hydrolysis product of PGI3.
37		15-keto Prostaglandin F1a	9a,11a-dihydroxy-15-oxo-prost-13E-en-1-oic acid	XPR1717	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		In fish, the 15-keto compounds (including 15-keto PGF1a) serve as post-ovulatory pheromones and are more active tha the parent prostaglandins.(Ref. 2022)													15-keto PGF1a is the initial metabolite of PGF1a via PG 15-dehydrogenase.					[2022]
38		19(R)-hydroxy Prostaglandin F1a	9a,11a,15S,19R-tetrahydroxy-prost-13E-en-1-oic acid	XPR1718	Takehiko Yokomizo		C₂₀H₃₆O₆	372.496															19(R)-hydroxy PGF1a is and w-1 hydroxylase metabolite of 19(R)-hydroxy PGF1a.(Ref. 2023)					[2023]
39		11b-Prostaglandin F2a	9a,11b,15S-trihydroxy-prosta-5Z,13E-dien-1-oic acid	XPR1719	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481															11b-PGF2a is the primary plasma metabolite of PGD2 in vivo.(Ref. 2025)					[2025]
40		13,14-dihydro-15-keto Prostaglandin F2a	9a,11a-dihydroxy-15-oxo-prost-5Z-en-1-oic acid	XPR1720	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481															13,14-dihydro-15-keto PGF2a is the first prominent plasma metabolite of PGF2a via PG 15-dehydrogenase pathway.(Ref. 2026)					[2026]
41		15(R)-Prostaglandin F2a	9a,11a,15R-trihydroxy-prosta-5Z,13E-dien-1-oic acid	XPR1721	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		15(R)-PGF2a has only quarter of the ability of PGF2a in hamster antifertility studies(Ref. 2027) due to reduced affinity for FP receptors.													15(R)-PGF2a is the C-15 epimer of the naturally occurring PGF2a.					[2027]
42		19(R)-hydroxy Prostaglandin F2a	9a.11a,15S,19R-tetrahydroxy-prosta-5Z,13E-dien-1-oic acid	XPR1722	Takehiko Yokomizo		C₂₀H₃₄O₆	370.480															19(R)-hydroxy PGF2a is an w-1 hydroxylase metabolite of PGF2a found in human semen.
43		20-hydroxy Prostaglandin F2a	9a,11a,15S,20-tetrahydroxy-prosta-5Z,13E-dien-1-oic acid	XPR1723	Takehiko Yokomizo		C₂₀H₃₄O₆	370.480															20-hydroxy PGF2a is the w-oxidation product of PGF2a via P450 w-oxidation in cultured type-II alveolar cells from pregnant rabbits.(Ref. 2028)					[2028]
44		Prostaglandin H1	9a,11a-epidioxy-15S-hydroxy-prost-13E-en-1-oic acid	XPR1724	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		PGH1 is known as suicide substrate and inhibits platelet thromboxane synthase with a Ki of 28 mM.(Ref. 2029)													PGH1 is a cylooxygenase metabolige of DGLA.					[2029]
45		Prostaglandin I3	6,9a-epoxy-11a,15S-dihydroxy-prosta-5Z,13E,17Z-trien-1-oic acid	XPR1725	Takehiko Yokomizo		C₂₀H₂₉O₅	349.441		PGI3 has equal ability to PGI2 in inhibitting human platelet aggregation.(Ref. 2031)													PGI3 is synthesized from EPA by cyclooxygenase and PGI synthase.					[2031]
46		D¹²-Prostaglandin J2	11-oxo-15S-hydroxy-prosta-5Z,9,12E-trien-1-oic acid	XPR1726	Takehiko Yokomizo		C₂₀H₃₀O₄	334.450		D¹²-PGJ2 has antitumor and antibiral activity, inhibiting growth of cultured L1210 cells with an IC50 of 0.7 mg/ml.(Ref. 2033)													D¹²-PGJ2 is a decomposition product of PGD2 in the presence of albumin.(Ref. 2032)					[2032] / [2033]
47		15-epi Prostaglandin A1	9-oxo-15R-hydroxy-prostsa-10,13E-dien-1-oic acid	XPR1728	Takehiko Yokomizo		C₂₀H₃₂O₄	336.466															15-epi PGA1 is produced by gorgonia soft corals.(Ref. 2000)					[2000]
48		13,14-dihydro-15-keto Prostaglandin A2	9-oxo-15R-hydroxy-prostsa-10,13E-dien-1-oic acid	XPR1729	Takehiko Yokomizo		C₂₀H₃₀O₄	334.450															13,14-dihydro-15-keto PGA2 is produced via non-enzymatic dehydration of 13,14-dihydro-15-keto PGE2, whose process is a ccelerated by the presence of albumin.(Ref. 2001/2002)					[2001] / [2002]
49		Prostaglandin D1	9a,15S-dihydroxy-11-oxo-prost-13E-en-1-oic acid	XPR1731	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		Prostaglandin D1 inhibits ADP-induced human platelet aggregation effect (IC50 value of 320 ng/ml). (Ref. 2040)Prostaglandin D1 inhibits the increase in vascular permeability in rat skin produced by prostaglandin E1, E2 and D2.(Ref. 2073) PGD1 is equal in activity to PGF1 alpha in causing constriction of central and peripheral airways of the dog.(Ref. 2083)																		[2040] / [2073] / [2083]
50		15(S)-15-methyl Prostaglandin D2	9a,15S-dihydroxy-11-oxo-15-methyl-prosta-5Z,13E-dien-1-oic acid	XPR1732	Takehiko Yokomizo		C₂₁H₃₄O₅	366.492		15(S)-15-methyl Prostaglandin D2 is reported to inhibit ADP-induce human platelet aggregation (IC50 value of 320 ng/ml) and increase systemic blood pressure in rat. (Ref. 2040)15(S)-15-methyl Prostaglandin D2 shows strong anti-fertility effect in hamster (100% at 50 mg/hamster).(Ref. 2040)																		[2040]
51		15-deoxy-D¹²^.¹⁴-Prostaglandin D2	9a-hydroxy-11-oxo-prosta-5Z,12E,14E-trien-1-oic acid	XPR1733	Takehiko Yokomizo		C₂₀H₃₀O₄	334.450		15-deoxy-D¹²^.¹⁴-Prostaglandin D2 shows cytotoxity on murine leukemia cell line (IC50 value of 0.3 mg/ml).(Ref. 1047) 15-deoxy-D¹²^.¹⁴-Prostaglandin D2 is a potent activator of eosinophils, inducing calcium mobilization, actin polymerization, and CD11b expression.(Ref. 2074)							lmax=296nm e296=18300					PGD2 and other metabolites are separated with HPLC. Please reffer following paper.(Ref. 2084)			15-deoxy-D¹²^.¹⁴-Prostaglandin D2 is formed from Prostaglandin D2 via D¹²-Prostaglandin D2. This reaction is proceeded under co-culture with Prostaglandin D2 and serum.(Ref. 2084)			[1047] / [2074] / [2084]
52		16,16-dimethyl Prostaglandin D2	9a,15R-dihydroxy-11-oxo-16,16-dimethyl-prosta-5Z,13E-dien-1-oic acid	XPR1734	Takehiko Yokomizo		C₂₂H₃₆O₅	380.518		16,16-dimethyl Prostaglandin D2 enhances ADP-induce human platelet aggregation and increase increase systemic blood pressure in rat. (Ref. 2040)																		[2040]
53		Prostaglandin E1 Alcohol	1,11a,15S-trihydroxy-prost-13E-en-9-one	XPR1735	Takehiko Yokomizo		C₂₀H₃₆O₄	340.497		Prostaglandin E1 Alcohol shows bronchodialational effect on human respiratory tract muscle.(Ref. 2042)Prostaglandin E1 Alcohol shows agnoist effects selectively for EP2 and EP4.(Ref. 2085)Prostaglandin E1 Alcohol inhibits M-CSF synthesis by bone marrow stromal cells.(Ref. 2086)																		[2042] / [2085] / [2086]
54		11-deoxy Prostaglandin E1	9-oxo-15S-hydroxy-prosto-13E-en-1-oic acid	XPR1736	Takehiko Yokomizo		C₂₀H₃₄O₄	338.482		11-deoxy Prostaglandin E1 shows spieces and subtype dependent EP agonistic effect. In guinea pig, 11-deoxy Prostaglandin E1 induce bronchodilation and vasodepression. (Ref. 2043) 11-deoxy Prostaglandin E1 is reported to increase cAMP release via EP receptors in Jurkat cells. (Ref. 2079) The Ki value of each murine EPs is 600 nM (EP1), 45 nM (EP2), 1.1 nM (EP3), 23 nM (EP4) .(Ref. 2036) 11-deoxy Prostaglandin E1, a selective EP2/EP3/EP4 agonist, inhibites IL-1beta-induced IL-6 production in human gingival fibroblast.(Ref. 2089) 11-deoxy Prostaglandin E1 stimulates K secretion through EP2 receptors at EC50 values of 8.3 nM in guinea pig distal colonic mucosa .(Ref. 2090)																		[2036] / [2043] / [2079] / [2089] / [2090]
55		15(R)-Prostaglandin E1	9-oxo-11a,15R-dihydroxy-prost-13E-en-1-oic acid	XPR1737	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		15(R)-Prostaglandin E1 dosen't have biological significance but inhibit 15-hydroxy PGDH (IC50 value of 189 mM).(Ref. 2044)																		[2044]
56		15(S)-15-methyl Prostaglandin E1	9-oxo-11a,15S-dihydroxy-15-methyl-prost-13E-en-1-oic acid	XPR1738	Takehiko Yokomizo		C₂₁H₃₆O₅	368.508		15(S)-15-methyl Prostaglandin E1 shows weak constriction effect on human respiratory tract smooth muscle.(Ref. 2045)15(S)-15-methyl Prostaglandin E1 at 300 ng/kg administered systemically (subcutaneously), selectively suppresses PMN-dependent edema formation.(Ref. 2078) In hamsters, 15(S)-15-methyl Prostaglandin E1 of 150 micrograms reduced the number of PMNLs adherent to blood vessels and infiltrating the ICT (infiltrated connective tissue) and other inflammation.(Ref. 2091)																		[2045] / [2078] / [2091]
57		16,16-dimethyl Prostaglandin E1	9-oxo-11a,15R-dihydroxy-16,16-dimethyl-prost-13E-en-1-oic acid	XPR1739	Takehiko Yokomizo		C₂₂H₃₈O₅	382.534		16,16-dimethyl Prostaglandin E1 shows vascular constriction in human.(Ref. 2045) 16,16-dimethyl Prostaglandin E1 inhibited electrically evoked [3H]norepinephrine (NE) overflow from the isolated, superfused rabbit iris-ciliary body without affecting basal tritium efflux.(Ref. 2092)																		[2045] / [2092]
58		9-deoxy-9-methylene Prostaglandin E2	9-methylene-11a,15S-dihydroxy-prosta-5Z,13E-dien-1-oic acid	XPR1740	Takehiko Yokomizo		C₂₁H₃₄O₄	350.492		9-deoxy-9-methylene Prostaglandin E2 decreases blood pressure in rat and (Ref. 2047)																		[2047]
59		9-deoxy-9-methylene-16,16-dimethyl Prostaglandin E2	9-methylene-11a,15R-dihydroxy-16,16-dimethyl-prosta-5Z,13E-dien-1-oic acid	XPR1741	Takehiko Yokomizo		C₂₃H₃₈O₄	378.545		9-deoxy-9-methylene-16,16-dimethyl Prostaglandin E2 shows term dependent termination of pregnant in conbination with other PGs.(Ref. 2048)																		[2048]
60		11b-Prostaglandin E2	9-oxo-11b,15S-dihydroxy-prosta-5Z,13E-dien-1-oic acid	XPR1742	Takehiko Yokomizo		C₂₀H₃₂O₅	352.465		11b-Prostaglandin E2 induces bone resorption at 10^-⁸ ~ 10^-⁶ M in rats.(Ref. 2049)																		[2049]
61		11-deoxy Prostaglandin E2	9-oxo-15S-hydroxy-prosta-5Z,13E-dien-1-oic acid	XPR1743	Takehiko Yokomizo		C₂₀H₃₂O₄	336.466		11-deoxy Prostaglandin E2 shows strong bronchoconstriction of human smooth muscle .(Ref. 2045)																		[2045]
62		11-deoxy-16,16-dimethyl Prostaglandin E2	9-oxo-15R-hydroxy-16,16-dimethyl-prosta-5Z,13E-dien-1-oic acid	XPR1744	Takehiko Yokomizo		C₂₂H₃₆O₄	364.519		In rat, 11-deoxy-16,16-dimethyl Prostaglandin E2 inhibits secretion of gastric acid secretion so that suppresses ulcer formation.(Ref. 2050) 11-deoxy-16,16-dimethyl Prostaglandin E2 contracts human resporatory tract smooth muscle.(Ref. 2045)																		[2045] / [2050]
63		15(R)-15-methyl Prostaglandin E2	9-oxo-11a,15R-dihydroxy-15-methyl-prosta-5Z,13E-dien-1-oic acid	XPR1745	Takehiko Yokomizo		C₂₁H₃₄O₅	366.492		15(R)-15-methyl Prostaglandin E2 shows increase of bicarbonate secretion in duodenum and inhibition of gastric acid secretion.(Ref. 2051)																		[2051]
64		15(S)-15-methyl Prostaglandin E2	9-oxo-11a,15S-dihydroxy-15-methyl-prosta-5Z,13E-dien-1-oic acid	XPR1746	Takehiko Yokomizo		C₂₁H₃₄O₅	366.492		15(S)-15-methyl Prostaglandin E2 inhibits gastric acid secretion and consequent ulcer formation.(Ref. 2052)																		[2052]
65		16,16-dimethyl Prostaglandin E2	9-oxo-11a,15R-dihydroxy-16,16-dimethyl-prosta-5Z,13E-dien-1-oic acid	XPR1747	Takehiko Yokomizo		C₂₂H₃₆O₅	380.518		16,16-dimethyl Prostaglandin E2 shows cervical ripening and uterine constriction and consequent inhibition of ulcer formation.(Ref. 2041/2046) 16,16-dimethyl Prostaglandin E2 increases eNOS mRNA expression of adult microvessels to values in the newborn pig.(Ref. 2076) 16,16-dimethyl Prostaglandin E2 prevents indomethacin-induced gastric lesions.(Ref. 2080)																		[2041] / [2046] / [2076] / [2080]
66		16-phenyl tetranor Prostaglandin E2	9-oxo-11a,15S-dihydroxy-16-phenyl-17,18,19,20-tetranor-prosta-5Z13E-dien-1-oic acid	XPR1748	Takehiko Yokomizo		C₂₂H₂₈O₅	372.455		16-phenyl tetranor Prostaglandin E2 induces hypotation in dogs and inhibit bronchoconstriction induced by histamine.(Ref. 2053)																		[2053]
67		17-phenyl trinor Prostaglandin E2	9-oxo-11a,15S-dihydroxy-17-phenyl-18,19,20-trinor-prosta-5Z13E-dien-1-oic acid	XPR1749	Takehiko Yokomizo		C₂₃H₃₀O₅	386.481		17-phenyl trinor Prostaglandin E2 shows constriction of the guinea pig ileum and strong anti-fertility effect in hamster.(Ref. 2054)																		[2054]
68		11-deoxy Prostaglandin F1a	9a,15S-dihydroxy-prost-13E-en-1-oic acid	XPR1750	Takehiko Yokomizo		C₂₀H₃₆O₄	340.497		11-deoxy Prostaglandin F1a shows inhibits gastric acid secretion and induces uterine constriction. (Ref. 2055/2056) 11-deoxy Prostaglandin F1a shows vasopression and bronchoconstriction effect in guinea pig.(Ref. 2043)																		[2043] / [2055] / [2056]
69		Prostaglandin F1b	9b,11a,15S-trihydroxy-prost-13E-en-1-oic acid	XPR1751	Takehiko Yokomizo		C₂₀H₃₆O₅	356.497		Prostaglandin F1b increase respiratory rate after application intravenously.(Ref. 2057)																		[2057]
70		11-deoxy Prostaglandin F1b	9b,15S-dihydroxy-prost-13E-en-1-oic acid	XPR1752	Takehiko Yokomizo		C₂₀H₃₆O₄	340.497		11-deoxy Prostaglandin F1b shows vasodepression and bronchodilationeffect in guinea pig.(Ref. 2043)																		[2043]
71		Prostaglandin F2a 1,11-lactone	9a,11a,15S-trihydroxy-prosta-5Z,13E-dien-1-oic acid, 1,11-lactone	XPR1753	Takehiko Yokomizo		C₂₀H₃₂O₄	336.466		Prostaglandin F2a 1,11-lactone shows reduction of vasoacitivity and anti-fertility effect.(Ref. 2058)																		[2058]
72		Prostaglandin F2a 1,15-lactone	9a,11a,15S-trihydroxy-prosta-5Z,13E-dien-1-oic acid, 1,15-lactone	XPR1754	Takehiko Yokomizo		C₂₀H₃₂O₄	336.466		Prostaglandin F2a 1,15-lactone terminates pregnancy at early stage.(Ref. 2059)																		[2059]
73		Prostaglandin F2a Alcohol methyl ether	1-methyl-9a,11a,15S-trihydroxy-prosta-5Z,13E-diene	XPR1755	Takehiko Yokomizo		C₂₁H₃₈O₄	354.524		Prostaglandin F2a Alcohol methyl ether shows hypotensive effect in ocular.(Ref. 2060)																		[2060]
74		Prostaglandin F2a dimethyl amide	N,N-dimethyl-9a,11a,15S-trihydroxy-prosta-5Z,13E-dien-1-amide	XPR1756	Takehiko Yokomizo		C₂₂H₃₉O₄	367.543		Prostaglandin F2a dimethyl amide shows inhibition of PGF2a -induced contraction in gerbil colon.
75		Prostaglandin F2a Ethanolamide	N-(2-hydroxyethyl)-9a,11a,15S-trihydroxy-prosta-5Z,13E-dien-1-amide	XPR1757	Takehiko Yokomizo		C₂₂H₃₉NO₅	397.549		Prostaglandin F2a Ethanolamide shows dialation effect in cat iris sphincter.(Ref. 2062)																		[2062]
76		Prostaglandin F2a isopropyl ester	9a,11a,15S-trihydroxy-prosta-5Z,13E-dien-1-oic acid, isopropyl ester	XPR1758	Takehiko Yokomizo		C₂₃H₄₀O₅	396.561		Prostaglandin F2a isopropyl ester is easily hydrolyzed into PGF2a and reduces intraocular pressure after admiration into eyes.(Ref. 2063)																		[2063]
77		5-trans Prostaglandin F2a	9a,11a,15S-trihydroxy-prosta-5E,13E-dien-1-oic acid	XPR1759	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		5-trans Prostaglandin F2a shows incease of respiratory rate in rabbit.(Ref. 2057)																		[2057]
78		11-deoxy Prostaglandin F2a	9a,15S-dihydroxy-prosta-5Z,13E-dien-1-oic acid	XPR1760	Takehiko Yokomizo		C₂₀H₃₄O₄	338.482		11-deoxy Prostaglandin F2a shows smooth muscle contraction effect in rabbit aorta, dog saphenous vein, guinea pig trachea.(Ref. 2064)																		[2064]
79		13,14-dihydro Prostaglandin F2a	9a,11a,15S-trihydroxy-prost-5Z-en-1-oic acid	XPR1761	Takehiko Yokomizo		C₂₀H₃₆O₅	356.497		13,14-dihydro Prostaglandin F2ainduce leuteolysis in hamster.(Ref. 2034)																		[2034]
80		15(S)-15-methyl Prostaglandin F2a	9a,11a,15S-trihydroxy-15-methyl-prosta-5Z,13E-dien-1-oic acid	XPR1762	Takehiko Yokomizo		C₂₁H₃₆O₅	368.508		Intramuscularly injection of 15(S)-15-methyl Prostaglandin F2a induce abortion.(Ref. 2067) 15(S)-15-methyl Prostaglandin F2a causes sustained contractions in human vascular smooth muscle tissues (fetal aorta and arterial smooth muscle from chorionic vessels).(Ref. 2077)15(S)-15-methyl Prostaglandin F2a shows reduction of serum progesterone and induction of luteolysis in non-pregnant animal.(Ref. 2065)																		[2065] / [2067] / [2077]
81		17-phenyl trinor Prostaglandin F2a	9a,11a,15S-trihydroxy-17-phenyl-18,19,20-trinor-prosta-5Z,13E-dien-1-oic acid	XPR1763	Takehiko Yokomizo		C₂₃H₃₂O₅	388.497		17-phenyl trinor Prostaglandin F2a reduces the intraocular pressure in the cat eye.(Ref. 2038)																		[2038]
82		Prostaglandin F2b	9b,11a,15S-trihydroxy-prosta-5Z,13E-dien-1-oic acid	XPR1764	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		Prostaglandin F2b shows bronchodialation effect in guinea pig and cat.(Ref. 2069)																		[2069]
83		16,16-dimethyl Prostaglandin F2b	9b,11a,15R-trihydroxy-16,16-dimethyl-prosta-5Z,13E-dien-1-oic acid	XPR1765	Takehiko Yokomizo		C₂₂H₃₈O₅	382.534		16,16-dimethyl Prostaglandin F2b reduce asthmatic bronchospasm.(Ref. 2070)																		[2070]
84		15-deoxy-D¹²^.¹⁴-Prostaglandin J2	11-oxo-prosta-5Z,9,12E,14Z-tetraen-1-oic acid	XPR1766	Takehiko Yokomizo		C₂₀H₂₈O₃	316.435		15-deoxy-D¹²^.¹⁴-Prostaglandin J2 induces lipogenesis and adipocyte differentiation in cultured cell line.(Ref. 2035) 15-deoxy-D¹²^.¹⁴-Prostaglandin J2 shows powerful proapoptotic effects by inhibiting I kappa B alpha degradation.(Ref. 2075)																		[2035] / [2075]
85		16,16-dimethyl Prostaglandin A1	9-oxo-15R-hydroxy-16,16-dimethyl-prosta-10,13E-dien-1-oic acid	XPR1767	Takehiko Yokomizo		C₂₂H₃₆O₄	364.519		16,16-dimethyl Prostaglandin A1 shows inhibition against infection of HSV and HIV-1 at the ID50 of 3.8-7.3 and 2.5 mg/ml respectively. (Ref. 2039) 16,16-dimethyl Prostaglandin A1 shows dose-dependent inhibition in growth of human oral squamous carcinoma cells.(Ref. 2071) 16,16-dimethyl Prostaglandin A1 shows cell cycle arrest at the G1/S phase due to nhibiting DNA synthesis. (Ref. 2081)						16,16-dimethyl Prostaglandin A1 is soluble in organic solvents (i.e. methyl acetate, DMSO, ethanol) at least 50 mg/ml and also in aqueous buffers or isotonic saline at least 2 mg/ml. But in basic solutions (pH >7.4) 16,16-dimethyl Prostaglandin A1 will be converted into 16,16-dimethyl Prostaglandin PGB1.	lmax=216nm e216=13000						16,16-dimethyl Prostaglandin A1 is a metabolism resistant analogue of PGA1.		16,16-dimethyl Prostaglandin A1 is a metabolism resistant analogue of PGA1.			[2039] / [2071] / [2081]
86		16,16-dimethyl Prostaglandin A2	9-oxo-15R-hydroxy-16,16-dimethyl-prosta-5Z,10,13E-trien-1-oi acid	XPR1768	Takehiko Yokomizo		C₂₂H₃₄O₄	362.503		16,16-dimethyl Prostaglandin A2 shows inhibitory effect on the proliferation of Sendai virus in monkey cells.(Ref. 1053) 16,16-dimethyl Prostaglandin A2 significantly increases mouse survival against nfection with influenza A by an average of 40% and decreases virus titers in the lungs without alteration of the host immune response.(Ref. 2082)						16,16-dimethyl Prostaglandin A2 is soluble in organic solvents (i.e. methyl acetate, DMSO, ethanol) at least 50 mg/ml and also in aqueous buffers or isotonic saline at least 2.4 mg/ml. But in basic solutions (pH >7.4) 16,16-dimethyl Prostaglandin A2 will be converted into 16,16-dimethyl Prostaglandin PGB2.	lmax=215nm e216=12200											[1053] / [2082]
87		16,16-dimethyl Prostaglandin A2 methyl ester	9-oxo-15R-hydroxy-16,16-dimethyl-prosta-5Z,10,13E-trien-1-oi acid, methyl ester	XPR1769	Takehiko Yokomizo					16,16-dimethyl Prostaglandin A2 methyl ester shows increase of survival from influenza A virus in infected mice (10 mg/day). Daily treatment of mice with 16,16-dimethyl Prostaglandin A2 methyl ester delayed tumour appearance, inhibited tumour growth and increased the survival time by 15-35%.(Ref. 2072)																		[2072]
88		d12-Prostaglandin D2	9a,15S-dihydroxy-11-oxo-prosta-5Z,12E-dien-1-oic acid	XPR1771	Takehiko Yokomizo		C₂₀H₃₂O₅	352.465		d12-PGD2 is catalyzed to d12-PGJ2, which has antimitotic and carcinogenic activities.(Ref. 2142)(Ref. 2143)																		[2142] / [2143]
89		15(R)-Prostaglandin D2	9a,15R-dihydroxy-11-oxo-prosta-5E,13E-dien-1-oic acid	XPR1772	Takehiko Yokomizo		C₂₀H₃₂O₅	352.465		15(R)-PGD2 is reported to have potent agonistic effect to the DP2 receptor 5 time higher than PGD2.(Ref. 2144)																		[2144]
90		11-deoxy-11-methylene Prostaglandin D2	9a,15S-dihydroxy-11-methylene-prosta-5Z,13E-dien-1-oic acid	XPR1773	Takehiko Yokomizo		C₂₁H₃₄O₄	350.492		11-deoxy-11-methylene PGD2 has been reported to be essentially without agonist activity on human platelets, a DP receptor assay.(Ref. 2145)																		[2145]
91		11-deoxy-11-methylene-15-keto Prostaglandin D2	9a-hydroxy-11-methylene-15-oxo-prosta-5Z,13E-dien-1-oic acid	XPR1774	Takehiko Yokomizo		C₂₁H₃₂O₄	348.476		PGD2 has been reported to have two receptors, DP1 and CRTH2. The latter was recently identified on human eosinophils, and 11-deoxy-11methylene-15-keto PGD2 ischemically stable ligand for this receptor.(Ref. 2146)																		[2146]
92		15(R)-15-methyl Prostaglandin D2	9a,15R-dihydroxy-11-oxo-15methyl-prosta-5Z.13E-dien-1-oic acid	XPR1775	Takehiko Yokomizo		C₂₁H₃₄O₅	366.492		15(R)-15-methyl PGD2 is reported as a potent selective agonist for the DP2 and CRTH2 and induce CD11b expression, actin polymerization, and chemotaxis in eosinophyils.(Ref. 2147)																		[2147]
93		11b-Prostaglandin E1	9-oxo-11b,15S-dihydroxy-prost-13E-en-1-oic acid	XPR1776	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		11b-PGE1 is reported to contract the rat uterus and guinea pig ileum with less potent activity.(Ref. 2148)																		[2148]
94		8-iso Prostaglandin E1	9-oxo-11a,15S-dihydroxy-(8b)-prost-13E-en-1-oic acid	XPR1777	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		8-iso PGE1 is reported as a pulmonary vasoconstrictor in anesthetized dogs at similar concentration to PGF2a.(Ref. 2150)													8-iso PGE1 is an isoprostane which is found in human semen at the concentration of 7 mg/ml.(Ref. 2149)					[2149] / [2150]
95		1a,1b-dihomo Prostaglandin E1	9-oxo-11a,15S-dihydroxy-1a,1b-dihomo-prost-13E-en-1-oic acid	XPR1778	Takehiko Yokomizo		C₂₂H₃₈O₅	382.534		1a,1b-dihomo PGE1 is produced during incubation of whole sheep seminal vessels but not in human. 1a,1b-dihomo PGE1 has been reported the activity in ex vivo preparations of rat aorta and rat PRP.(Ref. 2151)																		[2151]
96		15(R)-Prostaglandin E2	9-oxo-11a,15R-dihydroxy-prosta-5Z,13E-dien-1-oic acid	XPR1779	Takehiko Yokomizo		C₂₀H₃₂O₅	352.465		15(R)-PGE2 is shown to inhibito fertility at a dose of 1.0 mg in hamsters.(Ref. 2152)																		[2152]
97		8-iso Prostaglandin E2	9-oxo-11a,15S-dihydroxy-(8b)-prosta-5Z,13E-dien-1-oic acid	XPR1780	Takehiko Yokomizo		C₂₀H₃₂O₅	352.465		8-iso PGE2 inhibits U-46619 or I-BOP-induced platelet aggregation with IC50 values of 0.5 and 5 mM.(Ref. 2153) 8-iso PGE2 is also reported to decrease 80% of the GFR and renal plasma flow without affecting blood pressure in infusing into the renal artery of rats.(Ref. 2154)																		[2153] / [2154]
98		Prostaglandin F1b	9b,11a,15S-trihydroxy-prost-13E-en-1-oic acid	XPR1781	Takehiko Yokomizo		C₂₀H₃₆O₅	356.497		PGF1b has been reported to show enhance respiratory rate in experimental animals after intravenous application.(Ref. 2155)																		[2155]
99		11-deoxy Prostaglandin F1b	9b,15S-dihydroxy-prost-13E-en-1-oic acid	XPR1782	Takehiko Yokomizo					11-deoxy PGF1b shows vasodepressor and bronchodilator activities in guinea pigs at a dose of 500 mg/kg.(Ref. 2156)																		[2156]
100		Prostaglandin F2a Alcohol	1,9a,11a,15S-tetrahydroxyprosta-5Z,13E-dien	XPR1783	Takehiko Yokomizo		C₂₀H₃₆O₄	340.497		PGF2a Alcohol is reported to retain ocular hypotensive properties (Ref. 2157), but the target receptor is not cleared yet.(Ref. 2158)																		[2157] / [2158]
101		Prostaglandin F2a dimethyl amine	1-dimethylamino-9a,11a,15S-trihydroxy-prosta-5Z,13E-diene	XPR1784	Takehiko Yokomizo		C₂₂H₄NO₃	330.272		PGF2a is shown to inhibit the contractile effects of PGF2a by60% at 6 ng/ml.(Ref. 2159)																		[2159]
102		Prostaglandin F2a methyl ester	9a,11a,15S-trihydroxy-prosta-5Z,13E-dien-1-oic acid, methyl ester	XPR1785	Takehiko Yokomizo		C₂₁H₃₆O₅	368.508		PGF2a methyl ester is reported to have higher ocular hypotensive activity than PGF2a with application to eyes of cats at 2.5 mg of dose.(Ref. 2093)																		[2093]
103		15(R)-Prostaglandin F2a	9a,11a,15R-trihydroxy-prosta-5Z,13E-dien-1-oic acid	XPR1787	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		In hamster antifertility study, 15(R)-PGF2a is reported quarter potency of PGF2a, which is due to reduced affinity to FP receptors.(Ref. 2152)																		[2152]
104		8-iso Prostaglandin F2a	9a,11a,15S-trihydroxy-(8b)-prosta-5Z,13E-dien-1-oic acid	XPR1788	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		8-iso PGF2a is reported to inhibit platelet aggregation induced by U-46619 (1 mM) and I-BOP (0.3 mM) with IC50 of 1.6 mM and 1.8 mM, respectively.(Ref. 2094)													In normal human urine, 8-iso PGF2a level are about 180-200 pg/mg of creatinine.(Ref. 2095)					[2094] / [2095]
105		8-iso-13,14-dihydro-15-keto Prostaglandin F2a	9a,11a-dihydroxy-15-oxo-(8b)-prost-5Z-en-1-oic acid	XPR1789	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		8-iso-13,14-dihydro-15-keto PGF2a weakly has been reported to inhibit the U-46619 or collagen-induced platelet aggregation.(Ref. 2096)																		[2096]
106		8-iso-15-keto Prostaglandin F2a	9a,11a-dihydroxy-15-oxo-(8b)-prosta-5Z,13E-dien-1-oic acid	XPR1790	Takehiko Yokomizo		C₂₀H₃₂O₅	352.465		In vasoconstriction studies, 8-iso-15-keto PGF2a has been reported as a membern of vasoconstrictor on the rato isolated thoraacic aorta through TP receptor.(Ref. 2097)																		[2097]
107		20-ethyl Prostaglandin F2a	9a,11a-15S-trihydroxy-20a,20b-dihomoprosta-5Z,13E-dien-1-oic acid	XPR1791	Takehiko Yokomizo		C₂₂H₃₈O₅	382.534		20-ethyl PGF2a is considered as an intraocular hypotensive agent compared to unoprostone, due to the natural15(S) allylic hydroxyl in the lower side chain.
108		15(R)-15-methyl Prostaglandin F2a	9a,11a,15R-methyl-prosta-5Z,13E-dien-1-oic acid	XPR1792	Takehiko Yokomizo		C₂₁H₃₆O₅	368.508		15(R)-15-methyl PGF2a is converted into the active 15(S)-isomer, which induce luteolysis after injection in rhesus monkeys at a dose of 12 mg/animal.(Ref. 2098)																		[2098]
109		15(S)-15-methyl Prostaglandin F2a methyl ester	9a,11a,15S-trihydroxy-15-methyl-prosta-5Z,13E-dien-1-oic acid, methyl ester	XPR1793	Takehiko Yokomizo		C₂₂H₃₈O₅	382.534		15(S)-15methyl PGF2a methylester is hydrolysed in vivo to 15(S)-15-methyl PGF2a shown as a potent uterine stimulant and abortifacient.<<>><<>><<>>
110		17-phenyl trinor Prostaglandin F2a amide	9a,11a,15S-trihydroxy-17-phenyl-18,19,20-trinor-5Z,13E-dien-1-amide	XPR1794	Takehiko Yokomizo		C₂₃H₃₃NO₄	387.512		17-phenyl trinor PGF2a amide is expected to show the typical intraocular effects of latanoprost. In vivo study revlealed that 17-phenyl trinor PGF2a amide was converted the amides of various PGs to the free acids.(Ref. 2102)																		[2102]
111		17-phenyl trinor Prostaglandin F2a isopropyl ester	9a,11a,15S-trihydroxy-17-phenyl-18,19,20-trinor-prosta-5Z,13E-dien-1-oic acid, isopropyl ester	XPR1795	Takehiko Yokomizo		C₂₆H₃₈O₅	430.577		In the monky, 17-phenyl trinor PGF2a isopropyl ester shows the most potent activity in reducing IOP, lowering the IOP 1.3 mmHg below the level achieved by latanoprost at the dose of 3 mg/eye.<<>>
112		8-iso Prostaglandin F2b	9b,11a,15S-trihydroxy-(8b)-prosta-5Z,13E-dien-1-oic acid	XPR1796	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		8-iso PGF2b has been reported to show very weak contraction of human umbilical vein artery and does not promote aggregation of human whole blood.(Ref. 2104)(Ref. 2096)																		[2096] / [2104]
113		8-iso Prostaglandin F3a	9a,11a,15S-trihydroxy-(8b)-prosta-5Z,13E,17Z-trien-1-oic acid	XPR1797	Takehiko Yokomizo		C₂₀H₃₂O₅	352.465		There is only one report on 8-iso PGF3a showing inactive in a TP receptor mediated assay of human platelet shape change, where 8-iso PGF2a has an ED50 value of 1 mM.(Ref. 2105)																		[2105]
114		Prostaglandin H2	9a,11a-epidioxy-15S-hydroxy-prosta-5Z,13E-dien-1-oic acid	XPR1798	Takehiko Yokomizo		C₂₀H₃₂O₅	352.465		PGH2 was firstly reported as a potent vasoconstrictor.(Ref. 2106) And PGH2 has been reported as a TP receptor agonist which irreversibly aggregates huma platelets at 50-100 ng/ml and also as a suicide substrate for platelet TX synthase prosessing a Ki value of 18 mM .(Ref. 2107)																		[2106] / [2107]
115		6a-Prostaglandin I1	6R,9a-epoxy-11a,15S-dihydroxy-prost-13E-en-1-oic acid	XPR1799	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		6a-PGI1 is reported to promote cAMP accumulation in human thyroied slices and cells in a concentration dependent manner.(Ref. 2108) And also exhibits 6a-PGI1 inhibition of ADP-induced platelet aggregation at the IC50 value of 350 ng/ml.(Ref. 2109)																		[2108] / [2109]
116		6b-Prostaglandin I1	6S,9a-epoxy-11a,15S-dihydroxy-prost-13E-en-1-oic acid	XPR1800	Takehiko Yokomizo		C₂₀H₃₄O₅	354.481		6b-PGI1 has a Kact for adenylate cyclase in NCB-20 cells of 4.2 mM compared with 18 nM for PGI2.(Ref. 2110)																		[2110]
117		PROSTAGLANDIN I2	5(Z)-[7(R)-Hydroxy-6(R)-(3(S)-hydroxyocten-1(E)-yl)-1(S),5(R)-2-oxabicyclo[3.3.0]oct-3-ylidenpentanoic acid	XPR1801	Shouzo Yamamoto	PGI2	C₂₀H₃₂O₅	352.465		Prostaglandin I2 is a potent anti-aggregatory agent for platelets, relaxes blood vessels, and enhances vascular permeability (Ref. 0014). It binds to a receptor with 7 transmembrne domains (IP) coupled to a Gs protein (Ref. 0003).					[a]_D=78(C=0.8820, CHCl3) (Ref. 1014)			METHYL ESTER ; LIQUID MELT n 3370, 1740, 1695cm^-¹ (Ref. 1014)	¹-H-NMR(D₂O, GLYCINE BUFFER, pH10.4) : d 5.60(m, 2H, 13,14-CH), 4.66(m, 1H, 9-CH), 4.39(t, 1H, 5-CH), 4.15(q, 1H, 15-CH), 3.97(q, 1H, 11-CH), 2.20(t, 2H, 2-CH₂) (Ref. 1013)	11,15-BIS(TRIMETHYLSILYL) ETHER METHYL ESTER ; 495(M⁺-CH₃), 479, 439, 423, 349, 327, 323, 315, 313, 199, 173 (Ref. 1014)			In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin I2. Prostaglandin I2 is produced in blood vessels, lung and other tissues (Ref. 0013).	(Ref. 1014) [Table 0001]	Prostaaglandin I2 is produced by isomerization of 9,11-endoperoxide of prostaglandin H2 by the catalysis of prostaglandin I synthaase (Ref. 0015/0016). Prostaglandin I2 is unstable and decomposes readily to 6-keto-prostaglandin F2a. Its 2,3-dinor derivative is a major urinary metabolite (Ref. 0017).	cDNA (Ref. 0016) and genomic DNA (Ref. 0018) for prostaglandin I synthase were cloned. cDNA for IP was isolated (Ref. 0003).	Stability:unstable in water around neutrality with a half life of about 5 min at 37C and decomposes to 6-keto-PGF1a(Ref. 0011).	[0003] / [0011] / [0013] / [0014] / [0015] / [0016] / [0017] / [0018] / [1013] / [1014]
118		6-KETOPROSTAGLANDIN F1a	7-[3(R),5(S)-Dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)cyclopentan-1(R)-yl]-6-oxoheptanoic acid	XPR1811	Shouzo Yamamoto	6-KETO-PGF1a	C₂₀H₃₆O₆	372.496		Degradation of prostaglandin I2 to 6-keto-prostaglandin F1a brings about the loss of biological activities. For example, the hypotensive effect of prostaglandin I2 is at least 100 times mor active than 6-keto-prostaglandin F1a (Ref. 0013).					[a]= -9.6 (C=1.04 METHANOL) (Ref. 1053)	DIETHYL ETHER(Ref. 1052)METHANOL, ACETONE, ETHYL ACETATE (Ref. 1053)		NEAT: n 3400, 1715, 1245, 1045, 975, 915, 875, 845, 800, 730 cm^-¹ (Ref. 1053)	¹H-NMR(ACETONE-D₆) : d 6.1-5.4(bs, 4H), 5.5-5.2(m, 2H), 4.7-3.5(m, 3H), 2.5-1.1 (m, 22H), 0.86(t, 3H) (Ref. 1053)	METHYL ESTER ; 366(M⁺-18), 348, 335, 330, 323, 319, 279, 265, 223, 196, 195, 164, 143, 121, 111, 99, 95, 71 (Ref. 1053). DIRECT EXPOSURE AMMONIA CI POSITIVE : 370, 353, 244, 163, 153, 136. NEGATIVE : 368, 351, 334, 316, 225, 219, 166, 135, 127 (Ref. 1054)			When prostaglandin I2 is produced in animal tissues, it is unstable in aqueous solution, especially at acidic pH, and readily decomposed to 6-keto-prostaglandin F1a (Ref. 0013). Therefore, 6-keto-prostaglandin F1a is detected where prostaglandin I2 is produced.	(Ref. 1053) [Table 0001]	6-Keto-prostaglandin F1a is subjected to b-oxidation, and converted to 2,3-dinor-6-keto-prostaglandin F1a which appears in urine as a major metabolite (Ref. 0017).			[0013] / [0017] / [1052] / [1053] / [1054]
119		2,3-DINOR-6-KETOPROSTAGLANDIN F1a	5-[3(R),5(S)-Dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)cyclopentan-1(R)-yl]-4-oxopentanoic acid	XPR1821	Shouzo Yamamoto	2,3-DINOR-6-KETO-PGF1a	C₁₈H₃₂O₆	344.443							[a]²⁰^.²_D= +16.9 (C=1.76 CHLOROFORM, measured after 24 hours at 20C) (Ref. 1060)	METHANOL (Ref. 1059)				METHOXIME TRI-TMS ETHER METHYL ESTER ; m/e 601(M⁺), 586, 570, 530, 511, 496, 480, 440, 421, 390, 350, 300, 294, 263, 217, 205, 191, 73 (Ref. 1059)			When prostaglandin I2 or its non-enzymatic degradation product (6-keto-prostaglandin F1a) was infused into man, a major urinary metbolite was 2,3-dinor-6-keto-prostaglandin F1a, a b-oxidation product (Ref. 0017).	(Ref. 1060) [Table 0001]				[0017] / [1059] / [1060]
120		PROSTAGLANDIN J2	7-[2(R)-(3(S)-Hydroxy-1(E)-octenyl)-3-oxo-4-cyclopenten-1(R)-yl]-5(Z)-heptenoic acid	XPR1901	Shouzo Yamamoto	PGJ2	C₂₀H₃₀O₄	334.450		The anti-tumor and anti-viral activities of prostaglandin J2 are attributed to D12-prostaglandin J2 which is a degradation product of prostagladnin J2 and is characteristic of its alkylidene cyclopentenone structure (Ref. 0010).						ACETONITRILE(Ref. 1048)CHLOROFORM, ETHANOL (Ref. 1049)	l ^M^e^O^H_m_a_x = 305(e 1200), 216(e 9900)nm (Ref. 1049)	n 3400, 3200, 2660, 1710, 1085, 970 cm^-¹ (Ref. 1049)	¹H-NMR(CDCl₃) : d 7.75-7.55(m, 1H, 9-CH), 6.30-6.10(m, 1H, 10-CH), 5.90(brs, 2H, OH), 5.75-5.35(m, 4H), 4.30-3.95(m, 1H, 15-CH) (Ref. 1049)	TMS ETHER ; M⁺ 478.2934 (Ref. 1049)				(Ref. 1049) [Table 0001]	In aqueous solution prostaglandin D2 undergoes non-enzymatic dehydration and is converted to prostaglandin J2 (Ref. 0010).			[0010] / [1048] / [1049]
121			7-[2(E)-(3(S)-Hydroxyoctylidene)-3-oxo-4-cyclopenten-1(R)-yl]-5(Z)-heptenoic acid	XPR1911	Shouzo Yamamoto	D12-PGJ2	C₂₀H₃₀O₄	334.450		D12-Prostaglandin J2 is considered to be an ultimate metabolite of prostaglandin D2 with anti-tumor and anti-viral activities (Ref. 0042). The compound has no cell surface recptor, but is transported into cells and then inot nuclei. The biological activities of D12-prostaglandin J2 are due to the syntheses of various proteins including heat shock proteins, g-glutamylcysteine synthetase, collagen and heme oxygenase (Ref. 0043).						METHANOL(Ref. 1050)ETHANOL, CHLOROFORM, ETHYL ACETATE (Ref. 1051)	l ^E^t^O^H_m_a_x = 244(e 6100)nm (Ref. 1051)	n : 2930, 1700, 1640, 1580, 1232, 028 cm^-¹ (Ref. 1051)	¹H-NMR(CDCl₃) : d 7.5(dd, 1H, 9-CH), 6.56(t, 1H, 13-CH), 6.35(dd,1 H, 10-CH), 5.48(m, 2H, 5,6-CH), 3.88(m, 1H, 15-CH), 3.44(m, 1H, 8-CH) (Ref. 1051)	m/e 334(M⁺), 316, 245, 236 (Ref. 1051)				(Ref. 1049) [Table 0001]	In human plasma prostaglandin D2 is dehydrated and converted to 9-deoxy-D9,12-13,14-dihydro-prostaglandin D2 (D12-prostaglandin J2) catalyzedby serum albumin (Ref. 0042).			[0042] / [0043] / [1049] / [1050] / [1051]
122		THROMBOXANE A2	7-[3-(3(S)-Hydroxy-1(E)-octenyl)-1(S),5(S),4,6-dioxabicyclo[3.1.1]hept-2-yl]-5(Z)-heptenoic acid	XPR2001	Shouzo Yamamoto	TXA2	C₂₀H₃₂O₅	352.465		Thromboxane A2 aggregates platelets and constricts blood vessels and bronchi (Ref. 0014). Thromboxane A2 binds to a specific recptor (TP) coupled to Gq protein (Ref. 0033).													Thromboxane A2 is produced in platelets, polymorphonuclear leukocytes, macrophages, lung, kidney and spleen of various animals upon various biological stimulations (Ref. 0013).		Prostaglandin H2 produced by the catalysis of cyclooxygenase is further metabolized to thrombaxne A2 by thromboxane synthaase. Thromboxane A2 is unstable (half life 30 sec) and its oxetane ring is hydrolyzed to hemiacetal thromboxane B2 (Ref. 0017). The major urinary metabolite of tromboxane B2 is 2,3-dinor-thromboxane B2 (Ref. 0031), and 11-dehydro-thromboxane B2 is known as a suitble parameter for monitoring thromboxane production in human (Ref. 0032).	cDNA and genomic DNA for thromboxane A synthase (Ref. 0016) and those fro thromboxane A2 receptor (Ref. 0033) were cloned.	Stability:unstable in water around neutrality with a half life of about 40 sec at 37C and decomposes to TXB2 and 12-hydroxy-5,8,10-heptadecatrienoic acid(Ref. 0013).	[0013] / [0014] / [0016] / [0017] / [0031] / [0032] / [0033]
123		THROMBOXANE A3	7-[3-(3(S)-Hydroxy-1(E),5(Z)-octadienyl)-1(S),5(S),4,6-dioxabicyclo[3.1.1]hept-2-yl ]-5(Z)-heptenoic acid	XPR2002	Shouzo Yamamoto	TXA3	C₂₀H₃₀O₅	350.449		Thromboxane A3 did not cause platelet aggregation unlike thromboxane A2, and inhibited platelet aggregation by other agonists (Ref. 0090).															Prostaglandin H3 is produced from 5,8,11,14,17-eicosapentaenoic acid, which is one-eighth as efficient a substrate as arachidonic acid, by the catalysis of fatty acid cyclooxygenase, and then transformed to unstable thromboxane A3 (Ref. 0090), which is converted non-enzymatically to stable thromboxane B3.			[0090]
124		THROMBOXANE B2	7-[Tetrahydro-4(S),6-dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)-2H-pyran-3(S)-yl]-5(Z)-heptenoic acid	XPR2101	Shouzo Yamamoto	TXB2	C₂₀H₃₄O₆	370.480		Thromboxane B2 as s stable degradation product of thromboxane A2 shows diminishd biological activity (Ref. 0014).	95-96C (Ref. 1033)				[a]=57.4(C=0.26 ETHYL ACETATE) (Ref. 1033)	ETHYL ACETATE (Ref. 1035)		FILM: n 3380, 1705cm^-¹ (Ref. 1033)	¹H-NMR(CDCl₃) : d 5.86(m, 1H, 14-CH), 5.72(m, 1H, 13-CH), 5.46(m, 2H, 5,6-CH), 5.35 and 5.23(m, 1H, 11-CH), 4.41(m, 1H, 12-CH), 4.22(m, 1H, 15-CH), 4.11(m, 1H, 9-CH), 2.35(t, 2H, 2-CH₂), 0.89(m, 3H, 20-CH₃) (Ref. 1034)	m/e 335, 317 (Ref. 1033)			Thromboxane B2 as a stable degradation product of bioactive but unstable thromboxane A2 is detected in the tissue where thromboxane A2 is produced (Ref. 0013).	(Ref. 1033) [Table 0001]	The major urinary metabolite of tromboxane B2 is 2,3-dinor-thromboxane B2 (Ref. 0031), and 11-dehydro-thromboxane B2 is known as a suitble parameter for monitoring thromboxane production in human (Ref. 0032). 11-Hydroxythromboxane B2 dehydrogenase responsible for the 11-dehydro-thromboxane B2 production was identified as cytosolic aldehyde dehydrogenase (Ref. 0034).			[0013] / [0014] / [0031] / [0032] / [0034] / [1033] / [1034] / [1035]
125		THROMBOXANE B3	7-[Tetrahydro-4(S),6-dihydroxy-2(R)-(3(S)-hydroxy-1(E),5(Z)-octadienyl)-2H-pyran-3(S)-yl]-5(Z)-heptenoic acid	XPR2102	Shouzo Yamamoto	TXB3	C₂₀H₃₂O₆	368.464								DIETHYL ETHER (Ref. 1118), ETHYL ACETATE, CHLOROFORM (Ref. 1119)		FILM : n 3392, 3010, 2932, 1713, 1407, 1363, 1231, 1154, 1104, 1024, 973, 895 cm^-¹ (Ref. 1119)	¹H-NMR(CDCl₃, TMS) : d 5.85(dd, J=17.5, 6.3Hz,1H, 14-CH), 5.71(dd, J=17.5, 7.5Hz, 1H, 13-CH), 5.55(td, J=20.0, 12.5Hz, 1H, 18-CH), 5.48-5.31(m, 4H, 5,6,11,17-CH), 4.41(dd, J=12.5, 7.5Hz, 1H, 12-CH), 4.23(dt, J=12.5, 6.3Hz, 1H, 15-CH), 4.08(m, 1H, 9-CH), 2.40-2.24(m, 4H, 4,16-CH), 2.18-1.96(m, 7H, 2,7,10,19-CH), 1.81(m, 2H, 3-CH), 1.74-1.63(m, 2H, 3-CH), 1.45(tdd, J=8.8, 5.0, 5.0Hz, 1H, 8-CH), 0.96(t, J=7.5Hz, 3H, 20-CH) (Ref. 1119) ¹³C-NMR(CDCl₃) : 177.25, 136.52, 135.22, 130.75, 129.22, 127.49, 123.66, 123.59, 92.56, 71.58, 69.20, 64.95, 44.99, 36.01, 34.72, 32.89, 26.31, 24.80, 24.58, 24.58, 20.76, 14.21(Ref. 1119)	FAB : m/e 351(M⁺¹-H₂O), 333, 315, 307 (Ref. 1119)				(Ref. 1119) [Table 0001]	Prostaglandin H3 is produced from 5,8,11,14,17-eicosapentaenoic acid by the catalysis of fatty acid cyclooxygenase, and then transformed to unstable thromboxane A3 (Ref. 0090), which is converted non-enzymatically to stable thromboxane B3.			[0090] / [1118] / [1119]
126		2,3-DINORTHROMBOXANE B2	5-[Tetrahydro-4(S),6-dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)-2H-pyran-3(S)-yl]-3(Z)-pentenoic acid	XPR2111	Shouzo Yamamoto	2,3-DINOR-TXB2	C₁₈H₃₀O₆	342.427								ETHYL ACETATE, DIETHYL ETHER, DICHLOROMETHANE (Ref. 1057)			METHYL ESTER ; ¹H-NMR(CDCl₃) : d 5.77-5.0(m, 6H), 4.50-3.96(m, 5H), 3.71(s, 3H, OCH₃), 3.20-3.00(m, 2H) (Ref. 1057)	METHYL ESTER TRIS-TMS ETHER ; m/e 557, 482, 467, 411, 338, 301, 295, 267, 228, 225, 217 (Ref. 1056)			When thromboxane B2 is infused, 2,3-dinor-thromboxane B2 is found in urine of monkey (Ref. 0031) and man (Ref. 0048) as a major metabolite.		2,3-Dinor-thromboxane B2 is a b-oxidation product of thromboxane B2.			[0031] / [0048] / [1056] / [1057]
127		11-DEHYDROTHROMBOXANE B2	7-[Tetrahydro-4(S)-hydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)-6-oxo-2H-pyran-3(S)-yl]-5(Z)-heptenoic acid	XPR2121	Shouzo Yamamoto	11-DEHYDRO-TXB2	C₂₀H₃₂O₆	368.464								METHANOL, ETHYL ACETATE (Ref. 1058)		METHYL ESTER ; CHLOROFORM solution, n 1730 cm^-¹ (Ref. 1057)	METHYL ESTER ; ¹H-NMR(CDCl₃) : d 5.86-5.78(m, 2H), 5.56-5.32(m, 2H), 5.13-4.72(m, 1H), 5.23-4.05(m, 2H), 3.67(S, 3H, OCH₃)(Ref. 1057)	METHYL ESTER BIS-TMS ETHER ; m/e 526(M⁺), 511, 455, 370, 295 (Ref. 1057)			When thromboxane B2 is infused, 11-dehydro-thromboxane B2 is found as a major metabolite in the blood of rabbit (Ref. 0049) and man (Ref. 0032). The compound appears in urine as one of the mejor metabolites (Ref. 0032/0049).		11-Hydroxythromboxane B2 dehydrogenase is considered to be the enzyme responsible for 11-dehydro-thromboxane B2 production (Ref. 0034).			[0032] / [0034] / [0049] / [1057] / [1058]
128		LEUKOTRIENE A4	5(S),6(S)-Epoxyeicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid	XPR3001	Shouzo Yamamoto	LTA4	C₂₀H₃₀O₃	318.450		Leukotriene A4 as such is biologically less active than its active metabolites, leukotrienes B4 and C4. For example, leukotriene A4 is at least two orders of magnitude less potent than leukotrienes C4, D4 and E4 in contraction of guinea pig lung strips (Ref. 0022).					[a]=-21.9(C=0.32,CYCLOHEXANE) (Ref. 1024)	SOL. IN CYCLOHEXANE,METHANOL(Ref. 1024). STABILITIES : to decompose to 5,12-DIHYDROXY-6,8,10,14-EICOSATETRAENOIC ACID and 5,6-DIHYDROXY-7,9,11,14-EICOSATETRAENOIC ACID under neutral aqueous solution at 37C with one minite of half-life(Ref. 1030).	METHYL ESTER ; l ^M^e^O^H_m_a_x = 269(e 30,500), 278(e 40,000), 287(e 34,400) nm (Ref. 1031)			METHYL ESTER ; 332(M⁺), 316, 300, 221, 189, 181, 129, 101 (Ref. 1029)			Leukotriene A4 is produced as an intermediate for the biosyntheses of leukotrienes B4 and C4 in polymorphonuclear leukocytes, mast cells and macrophages of various animal species (Ref. 0022).	(Ref. 1031) [Table 0001]	Arachidonate 5-lipoxygenase is a bifunctional enzyme with a 5-oxygenase activity converting arachidonic acid to 5-hydroperoxy-6,8,11,14-eicosatetraenoic acid and a leukotriene A synthase activity converting the 5-hydroperoxy acid to leukotriene A4. The same enzyme produces leukotriene A4 from arachidonic acid via 5-hydroperoxy acid (Ref. 0025). The produced leukotriene A4 ia converted either to leukotriene B4 or to leukotriene C4 (Ref. 0022).	cDNA and genomic DNA for 5-lipoxygenase were cloned (Ref. 0007).	Stability:unstable in water around neutrality with a half life of about 1 min at 37C and decomposes to 5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid and 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid(Ref. 0021)	[0007] / [0021] / [0022] / [0025] / [1024] / [1029] / [1030] / [1031]
129		LEUKOTRIENE B4	5(S),12(R)-Dihydroxyeicosa-6(Z),8(E),10(E),14(Z)-tetraenoic acid	XPR3101	Shouzo Yamamoto	LTB4	C₂₀H₃₂O₄	336.466		Leukotriene B4 causes adhesion of leukocytes to endothelial cells, stimulates chemotaxis and chemokinesis of leukocytes(Ref. 0022), and enhances superoxide anion production by human polymorphonuclear leukocytes (Ref. 0023). Leukotriene B4 binds to a specific receptor with 7 transmembrane domains coupled to Gi/Go or Gq protein (Ref. 0024).						METHANOL (Ref. 1021)	METHANOL : 260(e 38,000), 270.5(e 50,000), 281(e 39,000)nm (Ref. 1021)		¹H-NMR(250MHz, D₂O) : d 6.45(m, 1H, 8-CH), 6.15(m, 2H, 9,10-CH), 6.0(m, 1H, 7-CH), 5.65(m, 1H, 11-CH), 5.40(m, 1H, 15-CH), 5.25(m, 2H, 6,14-CH), 4.60(5-CH), 4.05(m, 1H, 12-CH), 2.15(m, 2H, 13-CH), 2.00(m, 1H, 2-CH), 1.85(m, 2H, 16-CH), 1.35-1.60(m, 4H, 3,4-CH), 1.00-1.25(m, 6H, 17,18,19-CH), 0.70(m, 3H, 20-CH) (Ref. 1022)	m/e 336, 319, 301 (Ref. 1023)			Leukotriene B4 is produced by polymorphonuclear leukocytes and macrophages of various animal species upon various stimulations on the cells (Ref. 0021/0022).	(Ref. 1021) [Table 0001]	Arachidonic acid is metabolized to leukotrienen A4 with 5,6-epoxide by 5-lipoxygenases, and the product is further transformed to leukotrienee B4 by leukotriene A hydrolase (Ref. 0025). Leukotriene B4 is metabolized to lose its bioactivities either by w-oxidation (Ref. 0022) or by leukotriene B4 12-hydroxydehydrogenase (Ref. 0026).	cDNA and genomic DNA of 5-lipoxygenase (Ref. 0007) and cDNA for Leukotriene A hydrolase (Ref. 0007) were cloned. cDNA for leukotriene B 12-hydroxydehydrogenase was cloned (Ref. 0027).		[0007] / [0021] / [0022] / [0023] / [0024] / [0025] / [0026] / [0027] / [1021] / [1022] / [1023]
130		12-oxo-Leukotriene B4	5S-hydroxy-12-keto-[6Z, 8E, 10E, 14Z]-eicosatetraenoic acid	XPR3111	Takao Shimizu	12-oxo-LTB4	C₂₀H₃₀O₄	334.450		Increase in intracellular calcium in human leukocytes probably through BLT (LTB4 receptor). The IC 50 value is 100 times higher than that of LTB4.						Soluble in ethanol, methanol, ethyl acetate, acetonitril	UV maxima 316 nm, Absorbance at 320 nm is 41000/M					12-oxo-LTB4 is eluted at 7.8 min on RP-HPLC system as follows: Solvent:acetonitril/water/acetic acid, 50:50:0.01 (v/v/v), 0.01 % (w/v) Na2EDTA, pH 5.6 with ammonia Flow: 1 ml/min, isocratic Column: Cosmosil 5C18-AR (4.6 x 150 mm, Nacalai tesque, Tokyo) (Ref. 3111)	This metabolite is derived from LTB4 by LTB4 12-hydroxydehydrogenase. LTB4 12-hydroxydehydrogenase is expressed most abunduntly in liver and kidney.			LTB4 12-hydroxydehydrogenase cDNA is cloned from various animals. The accession numbers in DDBJ/EMBL/Genbank are shown in ( ). Pig (D49386) (Ref. 3112) (Ref. 3113) Human (D49387) (Ref. 3112) Rat (U66322) (Ref. 3114)		[3111] / [3112] / [3113] / [3114]
131		10,11,14,15-tetrahydro-12-keto-Leukotriene B4	5S-hydroxy-12R-keto-[6Z, 8E]-eicosatedienoic acid	XPR3112	Takao Shimizu	10,11,14,15-tetrahydro-12-keto-LTB4	C₂₀H₃₄O₄	338.482		unknown						Soluble in ethanol, methanol, ethyl acetate, acetonitril	UV maxima 235 nm, Absorbance at 320 nm is 30500/M					10, 11, 14, 15-tetrahydro-12-oxo-LTB4 is eluted at 12.6min on RP-HPLC system as follows: Solvent:acetonitril/water/acetic acid, 50:50:0.01 (v/v/v), 0.01 % (w/v) Na2EDTA, pH 5.6 with ammonia Flow: 1 ml/min, isocratic Column: Cosmosil 5C18-AR (4.6 x 150 mm, Nacalai tesque, Tokyo) (Ref. 3111)						[3111]
132		LeukotrieneB4 dimethyl amide	N,N-dimethy-5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraenamide	XPR3113	Takehiko Yokomizo		C₂₂H₃₇NO₃	363.534		Leukotriene B4 dimethylamide inhibits LTB4 induced degranulation of human neutrophils at the concentration of 130 nM (Ki) and release of lysozyme of PMNL.(Ref. 2120/2121/2122) The effect may be due to the antagonistic effect against LTB4 receptor.(Ref. 2120)																		[2120] / [2121] / [2122]
133		Leukotriene B4 Ethanolamide	N-(2-hydroxyethyl)-5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraenamide	XPR3114	Takehiko Yokomizo		C₂₂H₃₇NO₄	379.534		LTB4-EA is reported as a potent antagonist about 3 fold higher affinity for the human LTB4 receptor that LTB4. And LTB4-EA antagonizes the LTB4-induced contractions of guinea pig lung parenchyma with 10 nM as an EC50.(Ref. 2123)																		[2123]
134		6-trans Leukotriene B4	5S,12R-dihydroxy-6E,8E,10E,14Z-eicosatetraenoic acid	XPR3115	Takehiko Yokomizo		C₂₀H₃₂O₄	336.466		6-trans LTB4 is reported as a chemoattractant to neutrophils but the properties is relatively weal compared with LTB4.(Ref. 2124)																		[2124]
135		6-trans-12-epi Leukotriene B4	5S,12S-dihydroxy-6E,8E,10E,14Z-eicsatetraenoic acid	XPR3116	Takehiko Yokomizo		C₂₀H₃₂O₄	336.466		6-trans-12-epi LTB4 is reported as a weak chemotactic factors for PMNL with 20 times less potency thant LTB4 .(Ref. 2127)																		[2127]
136		12-epi Leukotriene B4	5S,12S-dihydroxy-6Z,8E,10E,14Z-eicsatetraenoic acid	XPR3117	Takehiko Yokomizo		C₂₀H₃₂O₄	336.466		12-epi LTB4 has a week agonistic character at both recombinant human BLT1 and BLT2 approximately 10 _M for complete activation.(Ref. 2128)																		[2128]
137		20-carboxy Leukotriene B4	5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraene-1,20-dioic acid	XPR3118	Takehiko Yokomizo		C₂₀H₃₀O₆	366.449		The biological activity of 20-carboxy LTB4 is only about 2.6% compared to that of LTB4 in causing PMNL degradation.(Ref. 2130)													20-carboxy LTB4 is a metabolite of LTB4 in human neutrophils					[2130]
138		14,15-dehydro Leukotriene B4	5S,12R-dihydroxy-6Z,8E,10E-eicosatriene-14-ynoic acid	XPR3119	Takehiko Yokomizo		C₂₀H₃₀O₄	334.450		14,15-dehydro LTB4 is reported as a selective ligand for the BLT1 and act as a selective antagonist of LTB4 in vivo.(Ref. 2131)																		[2131]
139		20-hydroxy Leukotriene B4	5S,12R,20-trihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid	XPR3120	Takehiko Yokomizo		C₂₀H₃₂O₅	352.465		20-hydroxy LTB4 is commonly accepted as a inactive metabolite of LTB4 but reported to contract parenchymal strips from guinea pig lung (Ref. 2129) and as a good ligand form BLT2 receptor.(Ref. 2128)																		[2128] / [2129]
140		20-trifluoro Leukotriene B4	5S,12R-dihydroxy-20,20,20-trifluoro-6Z,8E,10E,14Z-eicosatetraenoic acid	XPR3121	Takehiko Yokomizo		C₂₀H₂₉F₃O₄	390.437		20-trifluoro LTB4 has equal chemotactic activity to LTB4 with an EC50 of 3 nM (Ref. 2133/2134) but not degranulation activity of neutrophils.(Ref. 2132/2133/2134)																		[2132] / [2133] / [2134]
141		LEUKOTRIENE C4	5(S)-Hydoxy-6(R)-S-g-glutamylcysteinylglycinyleicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid	XPR3201	Shouzo Yamamoto	LTC4	C₃₀H₄₇O₉N₃S₁	625.775		Leukotriene C4 is a potent stimulator of airway smooth muscles and causes bronchoconstriction as demonstrated in vitro and in vivo experiments, and gastrointestinal smooth muscles are also contracted. Vascular permeability is enhanced by leukotriene C4 at concentrations lower by 3-4 orders of magnitude than histamine (Ref. 0022). Gasstrointestinal smooth muscles are contracted (Ref. 0021/0022). Leukotriene C4 binds to a receptor with 7 transmembrane domains coupled to Gia/o protein (CysLT1) with an affinity lower by two orders of magnitude than that of leukotriene D4 (Ref. 0030).						METHANOL (Ref. 1024)	l ^M^e^O^H_m_a_x = 270(e 32,000), 280(e 40,000), 290(e 31,000)nm (Ref. 1024)			the Chart(Ref. 1025)			Leukotriene C4 is produced by polymorphonuclear leukocytes, mast cells and macrophages of various animal species upon various stimulations on the cells (Ref. 0021/0022).	(Ref. 1024) [Table 0001]	Arachidonic acid is metabolized to leukotrienen A4 with 5,6-epoxide by 5-lipoxygenases, and the product is further transformed to leukotrienee C4 incorporating glutathione by the catalysis of leukotriene C synthase (Ref. 0021).	cDNA and genomic DNA of 5-lipoxygenase (Ref. 0007) and those for leukotriene C synthase (Ref. 0028/0029) were cloned. cDNA for CysLT1 was cloned (Ref. 0030).		[0007] / [0021] / [0022] / [0028] / [0029] / [0030] / [1024] / [1025]
142		11-trans Leukotriene C4	5S-hydroxy-6R-(S-glutathionyl)-7E,9E,11E14Z-eicosatetraenoic acid	XPR3202	Takehiko Yokomizo		C₃₀H₄₇N₃O₉	593.709		The contraction effect on guinea pig parenchymal and ileum is almost equal to LTC4.(Ref. 2137/2138)																		[2137] / [2138]
143		LEUKOTRIENE D4	5(S)-Hydroxy-6(R)-S-cysteinylglycinyleicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid	XPR3301	Shouzo Yamamoto	LTD4	C₂₅H₄₀O₆N₂S₁	496.661		Leukotriene D4 stimulates airway smooth muscles and causes bronchoconstriction. Vascular permeability is enhanced. Gasstrointestinal smooth muscles are contracted (Ref. 0021/0022). Leukotriene D4 binds to a receptor with 7 transmembrane domains coupled to Gia/o protein (CysLT1) with an affinity higher by two orders of magnitude than that of leukotriene C4 (Ref. 0030).						METHANOL (Ref. 1026)	l ^M^e^O^H_m_a_x = 270(e 32,000), 280(e 40,000), 290(e 31,000)nm (Ref. 1027)			N-ACETYL, 5-TRIMETHYLSILYL ETHER DIMETHYL ESTER derivative ; 638(M⁺), 623, 607, 548, 508, 405, 404, 315, 314, 274, 273 (Ref. 1026)			Leukotriene D4 is produced by basophils, eosinophils and macrophages of various animal species upon various stimulations on the cells (Ref. 0021/0022).	(Ref. 1028) [Table 0001]	g-Glutamyl transpeptidase hydrolyzes the glutathione moiety of leukotriene C4 and produces leukotriene D4 liberating glutamic acid (Ref. 0022),	cDNA for CysLT1 was cloned (Ref. 0030).		[0021] / [0022] / [0030] / [1026] / [1027] / [1028]
144		11-trans Leukotriene D4	5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E14Z-eicosatetraenoic acid	XPR3302	Takehiko Yokomizo		C₂₅H₄₀N₂O₆	464.595		The potency for contraction of guinea pig ileum, trachea, and parenchyma of 11-trans LTD4 is 10-25% compared to LTD4.(Ref. 2139/2140)																		[2139] / [2140]
145		LEUKOTRIENE E4	5(S)-Hydroxy-6(R)-S-cysteinyleicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid	XPR3401	Shouzo Yamamoto	LTE4	C₂₃H₃₇O₅N₁S₁	439.610		Leukotriene E4 stimulates airway smooth muscles from different animal species, and is less potent than C4 in contracting isolated guinea pig ileum (Ref. 0022).					DIMETHYL ESTER ; [a]=+35.2 (Ref. 1063)	METHANOL (Ref. 1063/1028)	MONO-POTASSIUM SALT;l = 270(e 40000), 280(e 49400), 291nm( e 40000) (Ref. 1028)		DIMETHYL ESTER ; ¹H-NMR(CDCl₃) : d 6.33(dd, J=14.5Hz, 10Hz, 1H, 10CH), 6.0(t, J=10Hz, 1H, 11-CH), 5.62(dd, J=14.4, 9.6Hz, 1H, 7-CH), 5.3(m, J=10,9Hz, 1H, 14-CH), 3.71 and 3.62(2S, 6H, OCH₃), 3.65(m, 1H, 5-CH), 3.4(m, 1H, 6-CH), 2.95(t, J=9Hz, 2H, 13-CH), 2.02(m, 2H, 16-CH), 0.86(t, J=6Hz, 3H, 20-CH) (Ref. 1063)				When leukotriene C4 was injected into male subjects, leukotriene E4 was found as a major urinary metabolite (Ref. 0050). Incubation of leukotriene D4 with human polymorphonuclear leukocytes produced leukotriene E4 (Ref. 0051).	(Ref. 1028) [Table 0001]	Leukotriene D4 is converted to E4 by extracellular action of a dipeptidase released from granules of human polymorphonuclear leukocytes (Ref. 0051). Leukotriene E4 is transformed to leukotriene F4 by g-glultamyltransferase in the presence of glutathione, and to N-acetyl leukotriene E4 by incubation with rat liver microsomes (Ref. 0052).			[0022] / [0050] / [0051] / [0052] / [1028] / [1063]
146		11-trans Leukotriene E4	5S-hydroxy-6R-(S-cysteinyl)-7E,9E,11E14Z-eicosatetraenoic acid	XPR3402	Takehiko Yokomizo		C₂₃H₃₇NO₅	407.544		11-trans LTE4 has equal potency to LTE4 in contracting guinea pig ileum.(Ref. 2141)																		[2141]
147		N-ACETYL-LEUKOTRIENE E4	5(S)-Hydroxy-6(R)-S-(N-acetylcysteinyl)eicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid	XPR3411	Shouzo Yamamoto	N-ACETYL-LTE4	C₂₅H₃₉O₆N₁S₁	481.646									l = 280 nm (270sh, 290sh) (Ref. 1067)							(Ref. 1068) [Table 0001]	Upon subcutaneous injection of leukotriene C4 in rats N-acetyl leukotriene E4 and N-acetyl 11-trans-leukotriene E4 are found in feces. Leukotriene E4 is transformed to N-acetyl leukotriene E4 by incubation with rat liver microsomes (Ref. 0052).			[0052] / [1067] / [1068]
148		LEUKOTRIENE F4	5(S)-Hydroxy-6(R)-S-glutamylcysteinyleicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid	XPR3501	Shouzo Yamamoto	LTF4	C₂₈H₄₄O₈N₂S₁	568.724									l = 270sh, 280(e 40000), 290sh nm (Ref. 1064)	N-TRIFLUOROACETYL METHYL ESTER ; n 3300, 1720, 1650, 1200, 985cm^-¹ (Ref. 1065)	N-TRIFLUOROACETYL METHYL ESTER ; ¹H-NMR(CDCl₃) : d 6.9-5.2(m, 8H), 5.0-4.5(m, 2H), 3.8-3.6(m, 1H, 5-CH), 3.79(s, 3H, OCH₃), 3.76(s, 3H, OCH₃), 3.67(s, 3H, OCH₃), 3.6-3.3(m, 1H, 6-CH), 3.1-2.7(m, 4H), 0.9(t, J=7Hz, 3H, 20-CH₃) (Ref. 1065)	N-TRIFLUOROACETYL METHYL ESTER ; 701(M⁺), 688, 675, 674, 662, 657, 649, 648, 578, 550, 465 (Ref. 1065)				(Ref. 1066) [Table 0001]	Leukotriene E4 is transformed to leukotriene F4 by g-glultamyltransferase in the presence of glutathione (Ref. 0052).			[0052] / [1064] / [1065] / [1066]
149		LIPOXIN A4	5(S),6(R),15(S)-Trihydroxyeicosa-7(E),9(E),11(Z),13(E)-tetraenoic acid	XPR4001	Shouzo Yamamoto	LXA4	C₂₀H₃₂O₅	352.465		Lipoxin A4 is either vasoconstrictive or vasodilatory, and has immunoregulatory activities blocking the cytotoxic action of NK cell, inhibiting adherence and chemotaxis of leukocytes induced by FMLP, PAF or leukotriene B4 (Ref. 0035).						DIETHYL ETHER, METHANOL (Ref. 1037)	l ^M^e^O^H_m_a_x = 287, 301(e 50,000), 316nm (Ref. 1037/1038)		¹H-NMR(250MHz, 5% CD₃OD/D₂O ) : d 0.8-0.9(brt, 3H), 1.2-1.8(m, 14H), 2.1-2.3(m, 2H), 3.4-3.6(m, 1H), 3.95-4.05(t, J=6.8Hz, 1H), 4.1-4.2(q, J=7.1Hz, 1H), 5.6-5.85(seven lines, 2H), 5.9-6.1(m, 2H), 6.2-6.45(m, 2H), 6.6-6.8(m, 2H) (Ref. 1037)	TMS-derivs. ; 582(M⁺), 492, 482, 379, 289, 203, 173, 171 (Ref. 1036)			Lipoxin A4 is produced by activated leukocytes (Ref. 0035/0036).	(Ref. 1037) [Table 0001]	Dual lipoxygenation pathways are considered for lipoxin A4 synthesis from arachidonic acid; either 15-lipoxygenase and 5-lipoxygenase in leukocytes or 5-lipoxygenase in leukocytes and 12-lipoxygenase in platelets (Ref. 0035).	cDNA for a receptor specific for lipoxin A4 was cloned out of orphan cDNAs (Ref. 0037).		[0035] / [0036] / [0037] / [1036] / [1037] / [1038]
150		LIPOXIN B4	5(S),14(R),15(S)-Trihydroxyeicosa-6(E),8(Z),10(E),12(E)-tetraenoic acid	XPR4101	Shouzo Yamamoto	LXB4	C₂₀H₃₂O₅	352.465		Lipoxin B4 is either vasoconstrictive or vasodilatory, and blocks the cytotoxic action of NK cell (Ref. 0035).					METHYL ESTER ; [a]=19.2(C=1.16, CHLOROFORM) (Ref. 1041)	METHANOL (Ref. 1039)	l ^M^e^O^H_m_a_x = 288, 300(e 50,000), 315nm (Ref. 1040)	METHYL ESTER ; CHCl₃ solution, n 3610, 3470, 3030, 3015, 2960, 2935, 2860, 1735, 1605, 1440, 1230, 1000, 980cm^-¹ (Ref. 1041)	¹H-NMR(250MHz, CDCl₃) : d 6.68(m, 2H), 6.36(dd, J=14.8 and 10.5Hz, 1H), 6.23(dd, J=14.1 and 10.7Hz, 1H), 6.0(m, 2H), 5.75(m, 2H), 4.17(m, 2H), 3.70(m, 1H), 3.65(s, 3H), 2.34(t, J=7.1Hz, 2H), 1.78-1.21(m, 12H), 0.86(t, J=6.4Hz, 3H) (Ref. 1041)	TRIMETHYLSILYL ETHER METHYL ESTER ; 582(M⁺), 492, 482, 409, 402, 379, 329, 319, 307, 289, 203, 173 (Ref. 1040)			Lipoxin B4 is produced by activated leukocytes (Ref. 0035/0036).	(Ref. 1041) [Table 0001]	Dual lipoxygenation pathways are considered for lipoxin B4 synthesis from arachidonic acid; either 15-lipoxygenase and 5-lipoxygenase in leukocytes or 5-lipoxygenase in leukocytes and 12-lipoxygenase in platelets (Ref. 0035).			[0035] / [0036] / [1039] / [1040] / [1041]
151		LEUKOTRIENE B5	5(S),12(R)-Dihydroxy-6(Z),8(E),10(E),14(Z),17(Z)-eicosapentaenoic acid	XPR4102	Shouzo Yamamoto	LTB5	C₂₀H₃₀O₄	334.450		Leukotriene B5 is about 1/30 as active as leukotriene B4 in stimulating aggregation of rat neutrophils, migration and lysosomal enzyme release of human polymorphonuclear leukocytes, and bradykinin-induced vascular permeability (Ref. 0092). Leukotriene B5 is much less active than B4 to increase intracellular calciuim level in human neutrophils (Ref. 0093).						METHANOL (Ref. 1120)	l _m_a_x = 260sh, 270, 290sh nm (Ref. 1121)		METHYL ESTER DIACETATE ; ¹H-NMR(BENZEN-d₆, 270MHz) : 6.79(dd, J=11.53, 14.83Hz, 1H, 8-CH), 6.34(dd, J=10.55, 14.83Hz, 1H, 10-CH), 6.09(dd, J=10.87, 14.83Hz, 1H, H-9), 6.03(t, J=11.53Hz, 7-CH), 5.90(dt, J =Ca.9.5, 11Hz, 5-CH), 5.63(dd, J=6.92, 14.82Hz, 11-CH), 5.60-5.38(m, 5H, 12,14,15,17,18-CH), 5.33(t, J=10.22Hz, 6-CH), 3.35(s, 3H), 2.83(m, 2H, 16-CH), 2.47(m, 1H, 13-CH), 2.38(m, 1H, 13-CH), 1.74(s, 3H), 1.68(s, 3H), 0.95(t, J=7.5Hz, 3H, 20-CH) (Ref. 1120)	METHYL ESTER TRIMETHYLSILYL ETHER M/E, 492(M⁺), 477, 461, 402, 391, 383,293, 267, 229, 217, 203 (Ref. 1121)			Leukotriene B5 is hardly detectable in human neutrophils, but is produced in the subjects fed with 5,8,11,14,17-eicosapentaenoic acid (Ref. 0091).	(Ref. 1120) [Table 0001]	Leukotriene B5 is produced via leukotriene A5 from 5,8,11,14,17-eicosapentaenoic acid, which is almost as active as arachidonic acid as substrate (Ref. 0065).			[0065] / [0091] / [0092] / [0093] / [1120] / [1121]
152		HEPOXILIN A3	8-Hydroxy-11,12(S,S)-epoxyeicosa-5,14(Z,Z),9(E)-trienoic acid	XPR5001	Shouzo Yamamoto	HxA3	C₂₀H₃₂O₄	336.466		As the biological activities of hepoxilin A3, insulin secretion from pancreas is stimulated, the enhanced vascular permeability by bradykinin is potentiated, hyperpolarization in hippocampal CA1 neurons is caused, and platelet aggregation is inhibited. At the molecular level hepoxilin A3 releases intracellular calcium, and opens potassium channel. Hepoxilin-specific binding proteins are present in human neutrophils (Ref. 0055).						DIETHYL ETHER (Ref. 1071)				METHYL ESTER TRIS-TMS ETHER ; m/e 422(M⁺), 407, 391, 332, 311, 282, 269(base peak) (Ref. 1070)			Hepoxilin A3 together with hepoxilin B3 is produced from arachidonic acid or more directly from 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid in various animal tissues including brain, pineal gland, pancreas and skin (Ref. 0055).	(Ref. 1072) [Table 0001]	The presence of hepoxilin synthase was suggested by a finding that intact cells (skin) and tissue slices (brain hippocampus and pineal gland) transformed 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid to hepoxilins A3 and B3, but tissue boiling inhibited the hepoxilin production (Ref. 0056).			[0055] / [0056] / [1070] / [1071] / [1072]
153		TRIOXILIN A3	8,11(R),12(S)-Trihydroxyeicosa-5(Z,9(E,14(Z)-trienoic acid	XPR5011	Shouzo Yamamoto	TrXA3	C₂₀H₃₄O₅	354.481												METHYL ESTER TRIS-TMS ETHER ; m/e 444, 384, 371, 353, 281, 243, 213(base peak) (Ref. 1074)					Trioxilin A3 is produced from hepoxilin A3 by the catalysis of hepoxilin epoxide hydrase of rat liver cytosol (Ref. 0058).			[0058] / [1074]
154		HEPOXILIN B3	10-Hydroxy-11(R),12(S)-epoxyeicosa-5,8,14(Z,Z,Z)-trienoic acid	XPR5101	Shouzo Yamamoto	HxB3	C₂₀H₃₂O₄	336.466		Little has been described about the biological actvity of hepoxilin B3 except for its poteniation of glucose-dependent insulin secretion (Ref. 0055) and of bradykinin-induced increase of vascular permeability (Ref. 0057).					ACETATE, METHYL ESTER ; [a]=-10.9(C=0.11, CHLOROFORM) (Ref. 1073)	DIETHYL ETHER (Ref. 1071)		ACETATE METHYL ESTER ; n(CHLOROFORM) 2956, 1743, 1550, 1372, 1234, 1033, 999cm^-¹ (Ref. 1073)	ACETATE METHYL ESTER ; ¹H-NMR(C₆D₆) : d 5.67(dd, J=9.2, 6.4Hz, 1H, 10-CH), 5.52, 5.46, 5.42, 5.35, 5.32, 3.36(s, 3H, OCH₃), 2.95(m, 2H, 7-CH), 2.92(m, 1H, 11-CH), 2.86(ddd, J=7.4, 7.4, 2.1Hz, 1H, 12-CH), 2.30(ddd, J=14.8, 7.4, 7.4Hz, 1H, 13-CH), 2.18(ddd, J=14.8, 7.4, 7.4Hz, 1H, 13-CH), 2.12(t, J=7.4Hz, 2H, 2-CH), 1.98(dt, J=7.4, 7.4Hz, 2H, 4-CH), 1.92(dt, J=8.8, 8.8Hz, 2H, 16-CH), 1.65(s, 3H, COCH₃), 1.60(tt, J=7.4, 7.4Hz, 2H, 3-CH), 1.25(m, 6H), 0.88(t, J=7.0Hz, 3H, 20-CH). (Ref. 1073) ¹³NMR(C₆D₆) : 134.22, 133.35, 130.17, 127.74, 124.31, 123.37, 70.86, 58.30, 55.71, 50.94, 33.30, 31.71, 29.66, 29.52, 27.59, 26.73, 25.00, 22.88, 20.53, 14.23 (Ref. 1073)	METHYL ESTER TMS ETHER ; m/e 311, 282, 269(base peak) (Ref. 1073)			Hepoxilin B3 together with hepoxilin A3 is produced from arachidonic acid or more directly from 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid in various animal tissues including brain, pineal gland, pancreas and skin (Ref. 0055).	(Ref. 1075) [Table 0001]	The presence of hepoxilin synthase was suggested by a finding that intact cells (skin) and tissue slices (brain hippocampus and pineal gland) transformed 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid to hepoxilins A3 and B3, but tissue boiling inhibited the hepoxilin production (Ref. 0056).			[0055] / [0056] / [0057] / [1071] / [1073] / [1075]
155		TRIOXILIN B3	10,11(S),12(R)-Trihydroxyeicosa-5,8,14(Z,Z,Z)-trienoic acid	XPR5111	Shouzo Yamamoto	TrXB3	C₂₀H₃₄O₅	354.481												METHYL ESTER TRIS-TMS ETHER ; m/e 342, 315, 269, 225, 213, 129(base peak) (Ref. 1074)					Trioxilin B3 is produced by hydrolysis of hepoxilin B3 with ammonium sulfate fraction of rat lung cytosol (Ref. 0056).			[0056] / [1074]
156			5(S)-Hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid	XPR6001	Shouzo Yamamoto	5(S)-HPETE	C₂₀H₃₂O₄	336.466								DIETHYL ETHER (Ref. 1077). ETHYL ACETATE (Ref. 1078)	l ^M^e^O^H_m_a_x = 230nm (Ref. 1076)								Arachidonic acid is oxygenated at the position 5 by the 5-oxygenase activity of arachidonate 5-lipoxygenase, and transformed to 5(S)-hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid, which is further converted to leukotriene A4 by the same enzyme. Thus, the 5-hydroperoxy acid is an intermediate for leukotriene A4 synthesis (Ref. 0025).	cDNA and genomic DNA of 5-lipoxygenase were cloned (Ref. 0007).		[0007] / [0025] / [1076] / [1077] / [1078]
157			12(S)-Hydroperoxy-5,8,10,14-(Z,Z,E,Z)-eicosatetraenoic acid	XPR6002	Shouzo Yamamoto	12(S)-HPETE	C₂₀H₃₂O₄	336.466		There are reports for various biological activities of 12(S)-hydroperoxy acid such as neurotransmission, melatonin secretion, inhibition of platelet function and constriction of basilar artery, but a general theory has not been established (Ref. 0059/0060).						DIETHYL ETHER (Ref. 1077), ETHYL ACETATE (Ref. 1078)	METHYL ESTER;l ^E^t^O^H_m_a_x = 237nm (e 31,000) (Ref. 1081)								When arachidonic acid is allowed to react with 12-lipoxygenase, the predominant product is 12(S)-hydroperoxy-5,8,10,14-(Z,Z,E,Z)-eicosatetraenoic acid (Ref. 0059). The produced 12(S)-hydroperoxy acid is a precursor of hepoxilin (Ref. 0055).	cDNA and genomic DNA for 12-lipoxygenases were cloned (Ref. 0060).		[0055] / [0059] / [0060] / [1077] / [1078] / [1081]
158			15(S)-Hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid	XPR6003	Shouzo Yamamoto	15(S)-HPETE	C₂₀H₃₂O₄	336.466		15-Lipoxygenase present in rabbit reticulocytes is presumed to be involved in the breakdown of mitochondrial membrane and the maturation of red cells (Ref. 0062). The enzyme is active with esterified polyunsaturated fatty acids contained in the membrane of subcelluar orgnelles or serum lipoprotein, and its peroxy products may be involved in the pathogenesis of arteriosclerosis (Ref. 0063).						DIETHYL ETHER (Ref. 1077), ETHYL ACETATE(Ref. 1078), ETHANOL(Ref. 1086), METHANOL(Ref. 1087)	l_m_a_x = 236nm(e 27000) (Ref. 1086) l_m_a_x(ISO-OCTANE) = 236nm(e 30000) (Ref. 1085)		METHYL ESTER ; ¹H-NMR(360MHz) : d 6.61(dd, J=11, 15.5Hz, 1H, 13-CH), 6.03(dd, J=10.5, 11Hz, 1H, 12-CH), 5.61(J=7.5Hz, 1H, 14-CH), 5.46(dd, J=7.5, 10.5Hz, 1H,11-CH), 5.39(m, 4H, 5,6,8,9-CH), 4.39(m, 1H, 15-CH), 3.67(s, 3H, OCH₃), 2.98(2H, 10-CH), 2.81(2H, 7-CH), 2.33(2H, 2-CH), 2.11(2H, 4-CH), 1.72(2H, 3-CH), 1.64(2H, 16-CH), 1.30(6H), 0.88(3H, 20-CH) (Ref. 1087)					(Ref. 1086) [Table 0001]	When arachidonic acid is allowed to react with 15-lipoxygenase, the predominant product is 15(S)-hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid (Ref. 0061). The 15-hydroperoxy acid is further transformed to dihydroperoxy acids or 14,15-epoxy acid with a conjugated triene by the catalyses of 12- and 15-lipoxygenases (Ref. 0065), and is a precursor for lipoxin biosynthesis (Ref. 0035).	cDNA and genomic DNA of 15-lipoxygenases were cloned (Ref. 0064).		[0035] / [0061] / [0062] / [0063] / [0064] / [0065] / [1077] / [1078] / [1085] / [1086] / [1087]
159			(R),(Z,E,Z,Z)-8-Hydroperoxy-5,9,11,14-eicosatetraenoic acid	XPR6014	Shouzo Yamamoto	8(R)-HPETE	C₂₀H₃₂O₄	336.466								ETHYL ACETATE , METHANOL (Ref. 1092)	l _m_a_x = 235.8nm (e 28,000) (Ref. 1092)						The compound is produced by the catalysis of 8(R)-lipoxygenase as an intermediate of coral prostanoid biosynthesis (Ref. 0073).					[0073] / [1092]
160			5(S)-Hydroxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid	XPR6101	Shouzo Yamamoto	5(S)-HETE	C₂₀H₃₂O₂	304.467							METHYL ESTER ; [a]=+14.0(C=2.0, BENZENE) (Ref. 1079)	DIETHYL ETHER (Ref. 1080)	METHYL ESTER ; l ^M^e^O^H_m_a_x = 235nm (e 30,500) (Ref. 1080)			METHYL ESTER ETHER ; m/e 406(M⁺), 391, 375, 316, 305, 255, 216, 215, 203, 190, 155, 150, 143, 136, 105, 80, 79 (Ref. 1080)				(Ref. 1079) [Table 0001]	When arachidonic acid is oxygenated by 5-lipoxygenase, 5(S)-hydroperoxy-6,,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid is produced (Ref. 0025). The latter compound is reduced to a corresponding 5(S)-hydroxy acid with whole cells or crude enzyme preparations.			[0025] / [1079] / [1080]
161			12(S)-Hydoxy-5,8,10,14-(Z,E,Z,Z)-eicosatetraenoic acid	XPR6102	Shouzo Yamamoto	12(S)-HETE	C₂₀H₃₂O₃	320.466		There are reports for various biological activities of 12(S)-hydroxy acid such as rat hypothalamic secretion of LH-RH, stimulated chemotactic activity of human eosinophils and neutrophils, stimulated migration of epidermal tumor cells and rat aortic smooth muscle cells, involvement in angiotension II-mediated aldosterone biosynthesis in human adrenal glomerulosa, and expression or activation of GpIIb/IIIa in tumor cells, but a general theory has not been established (Ref. 0059/0060).					METHYL ESTER ; [a]=+1.50(C=0.2, CHLOROFORM) (Ref. 1082), [a]=+13(C=1.5, ACETONE) (Ref. 1083)	DIETHYL ETHER , ACETONE , BENZENE (Ref. 1083)	METHYL ESTER ; l ^M^e^O^H_m_a_x = 234nm (Ref. 1084)METHYL ESTER ; l ^E^t^O^H_m_a_x = 237nm(e 30500) (Ref. 1081)	NEAT : n 3480b, 1710, 1460, 1400cm^-¹ (Ref. 1083)	¹H-NMR(250MHz, ACETONE-D₆) ; d 6.58(dd, J=15.3, 11.0Hz, 1H, 10-CH), 5.97(t, J=11.0Hz, 1H, 9-CH), 5.72(dd, J=15.3, 6.2 Hz, 1H, 11-CH), 5.29(m, 5H, 5,6,8,14,15-CH), 4.16(q, J=6.3Hz, 1H, 12-CH), 2.94(t, J=6.1Hz, 2H, 7-CH), 2.27(t,J= 7.4Hz, 2H,2-CH), 2.22(m, 2H, 13-CH), 1.66 and 2.14(m, 2H, 4-and 16-CH), 0.87(t, J=6.3Hz, 3H, 20-CH) (Ref. 1083). ¹³NMR(C₆D₆) : 174.3, 137.77, 132.02, 129.98, 129.62, 128.88, 128.69, 125.96, 124.44 (Ref. 1083)	METHYL ESTER ; m/e 316, 303, 223, 191, 141, 107(base peak) (Ref. 1084)				(Ref. 1082) [Table 0001]	When arachidonic acid is oxygenated by 12-lipoxygenase, 12(S)-hydroperoxy-5,8,10,14-(Z,Z,E,Z)-eicosatetraenoic acid is produced (Ref. 0059). The latter compound is reduced to a corresponding 12(S)-hydroxy acid with whole cells or crude enzyme preparations.			[0059] / [0060] / [1081] / [1082] / [1083] / [1084]
162			15(S)-Hydroxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid	XPR6103	Shouzo Yamamoto	15(S)-HETE	C₂₀H₃₂O₃	320.466		In connection with biological activities of 15-hydroxyeicosatetraenoic acid, there are reports for pain response of skin, mucus secretion in airway, histamine hypersensitivity, prolactin secretion, and regulation of protein phosporylation and cell signalling (Ref. 0064).						DIETHYL ETHER (Ref. 1086)	METHYL ESTER ; l (ISOOCTANE) = 236nm(e 27200) (Ref. 1086)		METHYL ESTER ; ¹H-NMR(90MHz) : d 6.56(dd, J=11, 14.5Hz, 1H, 13-CH), 6.02(dd, J=11,11Hz, 1H, 12-CH), 5.7(dd, J=6.8, 14.5Hz, 1H,14-CH), 5.51(dd, J=6,11Hz, 1H, 11-CH), 4.16(dd, J=6.8, 6.8Hz, 1H, 15-CH), 3.69(s, 3H, OCH₃), 2.98(2H, 10-CH), 2.84(2H, 7-CH), 2.35(2H, 2-CH), 2.08(2H, 4-CH), 1.47(2H, 16-CH), 2.3-0.9(11H) (Ref. 1086)	METHYL ESTER TMS ETHER ; m/e 406(M⁺), 391, 335, 316, 305, 225, 173 (Ref. 1086)				(Ref. 1086) [Table 0001]	When arachidonic acid is oxygenated by 15-lipoxygenase, 15(S)-hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid is produced (Ref. 0061). The latter compound is reduced to a corresponding 15(S)-hydroxy acid with whole cells or crude enzyme preparations.			[0061] / [0064] / [1086]
163			(R),(Z,Z,E,Z)-12-Hydroxy-5,8,10,14-eicosatetraenoic acid	XPR6112	Shouzo Yamamoto	12(R)-HETE	C₂₀H₃₂O₃	320.466								METHANOL (Ref. 1089), ETHYL ACETATE , 1-CHLOROBUTANE (Ref. 1090)	l _m_a_x = 237nm (Ref. 1089)			METHYL ESTER TMS ETHER ; m/e 406(M⁺), 391, 375, 316, 295 (Ref. 1089)			The compound is detected in the pathological skin of psoriasis patient (Ref. 0069), and it is a P-450 product from arachidonic acid as demonstrated with microsomal preparations of bovine cornea (Ref. 0070) and rat liver (Ref. 0071). The compound is also found in sea urchin eggs (Ref. 0072).	(Ref. 1091) [Table 0001]				[0069] / [0070] / [0071] / [0072] / [1089] / [1090] / [1091]
164			(R),(Z,E,Z,Z)-8-Hydroxy-5,9,11,14-eicosatetraenoic acid	XPR6114	Shouzo Yamamoto	8(R)-HETE	C₂₀H₃₂O₃	320.466		The compound is involved in the maturation of starfish oocyte (Ref. 0074).					8(S)-ISOMER METHYL ESTER ; [a]=-4.75(C=0.4, CHLOROFORM) (Ref. 1091)	ETHYL ACETATE (Ref. 1092)	METHYL ESTER ; l _m_a_x = 235.8nm (e 28,000)(Ref. 1092)		8(S)-ISOMER METHYL ESTER ; ¹H-NMR(CDCl₃) : d 6.56(dd, J=14.5, 11.1Hz, 1H, 10-CH), 6.00(brt, J=11.1, 9.7Hz, 1H, 11-CH), 5.72(dd, J=7.3, 14.5Hz, 1H, 9-CH), 5.59-5.16(m, 5H), 4.23(q, 1H,8-CH), 3.71(s, 3H,OCH₃), 2.95(t, 2H,13-CH), 2.35(t, 4H, 4,7-CH), 2.11(sextet, 4H), 1.73(pentet, 2H, 3-CH), 1.56(brs, S, 1H, OH), 1.32(m, 6H), 0.91(t, 3H, 20-CH) (Ref. 1091)	METHYL ESTER, TMS ETHER ; m/e 265 (Ref. 1092). 8(S)-ISOMER METHYL ESTER TMS ETHER ; m/e 406, 391, 316, 265, 243 (Ref. 1091)				(Ref. 1091) [Table 0001]				[0074] / [1091] / [1092]
165			(R),(Z,Z,Z)-12-Hydroxy-5,8,14-eicosatetraenoic acid	XPR6122	Shouzo Yamamoto		C₂₀H₃₄O₃	322.482		The compound has vasodilatory activity, and may be involved in the wound-healing of corneal injury (Ref. 0075).					METHYL ESTER ; [a]=-3.0(C=0.8, ACETONE) (Ref. 1093)	ETHYL ACETATE (Ref. 1094)			METHYL ESTER ; ¹H-NMR(CDCL₃) : d 5.63-5.51(m, 1H), 5.47-5.28(m, 5H), 3.67(S, 3H), 3.67-3.57(m, 1H), 2.79(t, J=5.5Hz, 2H), 2.32(t, J=7.4Hz, 3H), 2.30-1.99(m, 6H), 1.76-1.39(m, 6H), 1.40-1.23(m, 6H), 0.88(t, J=6.8Hz, 3H) (Ref. 1093)	METHYL ESTER TMS ETHER ; m/e 393, 319, 297 (Ref. 1094)			The compound is produced from arachidonic acid which is incubated with bovine corneal microsomes in the presenc of NADPH (Ref. 0075).	(Ref. 1093) [Table 0001]				[0075] / [1093] / [1094]
166			(S),(Z,E,E)-12-Hydroxy-5,8,10-heptadecatrienoic acid	XPR6201	Shouzo Yamamoto	HHT	C₁₈H₃₀O₃	294.429		The compound stimulates chemotactic and chemokinetic activities of human polymorphonuclear leukocytes (Ref. 0066).					METHYL ESTER ; [a] =+7.5(C=0.2, CHLOROFORM) (Ref. 1088)	DIETHYL ETHER (Ref. 1081)	METHYL ESTER ; ETHANOL : 232nm(e 33,400)(Ref. 1081). METHANOL : 240nm (Ref. 1088)		METHYL ESTER ; ¹H-NMR(CDCl₃) : d 6.17(dd, J=15.11, 10.36Hz, 1H, 10-CH), 6.04(dd, J=15,05, 10.52Hz, 1H, 9-CH), 5.66(dt, J=15.16, 6.48Hz, 1H), 5.60(dd, J=17.17, 7.04Hz, 1H, 11-CH), 5.42(m, 2H, 5-CH, 6-CH), 4.1(m, 1H, 12-CH), 3.66(s, 3H, COOCH₃), 2.81(m, 2H, 7-CH), 2.36(t, J=7.51Hz, 2H, 2-CH), 2.1-0.85(m, 16H, CH₂ and CH₃) (Ref. 1088)	METHYL ESTER TMS ETHER ; m/e 366(M⁺), 335, 295, 276, 225, 173, (128)(Ref. 1017) METHYL ESTER ; 298(M⁺), 224 (Ref. 1088)				(Ref. 1088) [Table 0001]	When prostaglandin H2 reacts with thromboxane A synthase and the endoperoxide moiety is cleaved, the production of thromboxane A2 is accompanied by the formation of 12(S)-hydroxy-5,8,10-heptadecatrienoic acid in an almost equimolar amount liberating malondialdehyde (Ref. 0067). This compound is also a product of non-enxymatic degradation of prostaglandin H2 (Ref. 0068).			[0066] / [0067] / [0068] / [1017] / [1081] / [1088]
167		5(6)OXIDO-8,11,14-EICOSATRIENOIC ACID	(Z,Z,Z)-5,6-Epoxy-8,11,14-eicosatrienoic acid	XPR6300	Shouzo Yamamoto	5,6-EET	C₂₀H₃₂O₃	318.450		The compound is active in stimulated secretion of somatostatin, insulin and glucagon, vasodilataion and regulation of intracellular calcium (Ref. 0078).										METHYL ESTER ; m/e 334(M⁺), 316, 303, 283, 267, 233, 190, 176, 163,143(base peak) (Ref. 1095). METHYL ESTER ; m/e 334(M⁺), 316, 303, 285, 245 (Ref. 1096)			The compound is produced when arachidonic acid in the presence of NADPH is incubated with the liver microsomes of rat (Ref. 0076) or rabbit (Ref. 0077).	(Ref. 1097) [Table 0001]				[0076] / [0077] / [0078] / [1095] / [1096] / [1097]
168		8(9)OXIDO-5,11,14-EICOSATRIENOIC ACID	(Z,Z,Z)-8,9-Epoxy-5,11,14-eicosatrienoic acid	XPR6301	Shouzo Yamamoto	8,9-EET	C₂₀H₃₂O₃	318.450		The compound relaxes intestinal artery (Ref. 0078).					8(S)9(R)-EET METHYL ESTER ; [a]=+2.33(C=1, ACETONE) (Ref. 1098)	CHLOROFORM (Ref. 1099)			¹H-NMR(CDCl₃) : d 5.70-5.08(m, 6H), 3.06-2.65(m, 4H), 2.62-1.04(complex m, 18H), 0.88(t, 3H) (Ref. 1099)	METHYL ESTER ; m/e 334(M⁺), 316, 303, 290, 245, 193, 183, 175, 165 (Ref. 1096)			The compound is produced when arachidonic acid in the presence of NADPH is incubated with the liver microsome of rat (Ref. 0076) or rabbit (Ref. 0077). It is also found in rabbit kidney (Ref. 0079) and human urine (Ref. 0080).	(Ref. 1098) [Table 0001]				[0076] / [0077] / [0078] / [0079] / [0080] / [1096] / [1098] / [1099]
169		11(12)OXIDO-5,8,14-EICOSATRIENOIC ACID	(Z,Z,Z)-11,12-Epoxy-5,8,14-eicosatrienoic acid	XPR6302	Shouzo Yamamoto	11,12-EET	C₂₀H₃₂O₃	318.450		The compound relaxes intestinal artery, inhibits vasopressin-dependent water flow in urinary bladder, and regulates intracellular calcium level (Ref. 0078).					11(R),12(S)-EET METHYL ESTER ; [a]=+4.94(C=1.64 ,ACETONE) (Ref. 1098) 11(S),12(R)-EET METHYL ESTER ; [a]=-2.34(C=0.66, CHLOROFORM) (Ref. 1099)				¹H-NMR(CDCl₃) : d 5.54-5.20(m, 6H), 3.61(s, 3H), 3.00-2.68(m, 4H), 2.37-2.00(m, 10H), 1.81-1.54(m, 2H), 1.46-1.13(m, 6H), 0.88(t, J=7Hz, 3H) (Ref. 1098)	METHYL ESTER ; m/e 340(M⁺), 322, 309, 227, 155 (Ref. 1096)			The compound is produced when arachidonic acid in the presence of NADPH is incubated with the liver microsome of rat (Ref. 0076) or rabbit (Ref. 0077).	(Ref. 1098) [Table 0001]				[0076] / [0077] / [0078] / [1096] / [1098] / [1099]
170		14(15)OXIDO-5,8,11-EICOSATRIENOIC ACID	14,15-Epoxy-(Z,Z,Z)-5,8,11-eicosatrienoic acid	XPR6303	Shouzo Yamamoto	14,15-EET	C₂₀H₃₂O₃	318.450		The compound stimulates glulcagon release, inhibits vasopressin-dependent water flow in urinary bladder, regulates intracellular calcium level, and inhibits platelet aggregation (Ref. 0078).					14(R),15(S)-EET METHYL ESTER ; [a]=-2,75(C=0.70, CHLOROFORM) 14(S),15(R)-EET METHYL ESTER ; [a]=+2.78(C=0.82, CHLOROFORM) (Ref. 1099)					METHYL ESTER ; m/e 334(M⁺), 316, 281, 263, 220, 161, 147, 119, 91(base peak) (Ref. 1095). METHYL ESTER ; m/e 334(M⁺), 316, 303, 263, 245, 235, 234, 220, 119, 91 (Ref. 1096)			The compound is produced when arachidonic acid in the presence of NADPH is incubated with the liver microsome of rat (Ref. 0076) or rabbit (Ref. 0077). It is also found in rabbit kidney (Ref. 0079) and human urine (Ref. 0080).	(Ref. 1099) [Table 0001]				[0076] / [0077] / [0078] / [0079] / [0080] / [1095] / [1096] / [1099]
171		17(R)(18S)OXIDO-5,8,11,14-EICOSATETRATENOIC ACID	17,18-(R,S)-Epoxy-5,8,11,14-(Z,Z,Z,Z)-eicosatetraenoic acid	XPR6304	Shouzo Yamamoto	17(18)EpETE	C₂₀H₂₈O₃	316.435												d,l-mixture, METHYL ESTER ; m/e 303, 301, 285, 275, 273, 271, 260, 257, 253, 245, 243, 231, 217, 213, 206, 199, 187, 180, 173, 159, 145, 131, 119, 117, 105, 93, 91(100%), 81, 79, 71, 67, 59, 57, 55 (Ref. 1100)			The compound is produced when the microsomes of monkey seminal vesicle is incubated with 5,8,11,14,17-eicosapentaenoic acid (Ref. 0081).	(Ref. 1100) [Table 0001]				[0081] / [1100]
172		Anandamide(20:4, n-6)	N-Arachidonoylethanolamine	XPR7001	Keizo Waku		C₂₂H₃₇NO₂	347.535		Anandamide inhibited the specific binding of cannabinoid probe to synaptosomal membrane and produced a concentration-dependent inhibition of the electrically evoked twitch response of the mouse vas deferens, a characteristic effect of psychotropic cannabinoids. Anandamidefunctions as a natural ligand for the cannabinoid receptor (CBl). Binding to rat brain CB1, Ki(nM) = 39.5.7(Ref. 7001)	oil(Ref. 7001)					soluble in organic solvent(Ref. 7001)			¹H NMR spectra.The peaks attributed to double bond protons(d5.30 to 5.45, multiplet)were coupled with those of protons that have the chemical shifts of doubly allylic protons(d2.75 to 2.90, multiplet). (Ref. 7001)	CID measurement of m/z 348 MH⁺ion gave rise to the following significant fragments:m/z 287, 245 ,203, 62 (highest abundance), and 44. m/z 62 fragment ion is HOCH₂CH₂NH₂⁺. (Ref. 7001)		1-Anthroyl derivatives of various types of N-acylethanolamine were separated by reverse phase HPLC (Ref. 7005) [Chromatogram 7001]	Originally found in porcine brain (Ref. 7006). It was also found in rat brain (Ref. 7005)and testis(Ref. 7008)	N-Arachidonoylethanolamine was synthesized from arachidonyl chloride and ethanolamine. The product was purified by silica gel column chromatography. It was 97 % pure as judged by GC-MS. (Ref. 7001)	It was biosynthesized from N-acylphosphatidylethanolamine by phospholipase D like reaction in rat brain microsomes (Ref. 7005).It was hydrolyzed by the anandamide amidohydrolase in rat brain microsomes to ethanolamine and arachidonic acid (Ref. 7007).	1. CB1(Ref. 7002) 2. CB2(Ref. 7003) 3. CB1A(Ref. 7004)		[7001] / [7002] / [7003] / [7004] / [7005] / [7006] / [7007] / [7008]
173		Anandamide (20:2, n-6)	N-cis-11,14-eicosadienoyl ethanolamine	XPR7002	Keizo Waku		C₂₂H₂₇NO₂	337.455		Binding of 20:2 anandamide to the Brain cannabinoid receptor (CB1)Ki (nM)= 1500(Ref. 7001)	oil (Ref. 7001)					soluble in organic solvent (Ref. 7001)			¹H NMR (CDCl3) d5.90 (br s, 1H), 5.30-5.38 (m, 4H), 3.70 (t, J=4.4Hz, 2H), 3.40-3.45 (m, 2H), 2.78 (t, J=5.4Hz,2H), 2.18 (t, J=7.1 Hz, 2H), 2.00-2.12 (m, 2H), 1.50-1.70 (m, 8H), 1.30 (br s, 8H), 0.89 (t, J=7.5 Hz, 3H). (Ref. 7001)					Anandamide (20:2, n-6) was prepared from cis-11, 14-eicosadienoyl chloride and ethanolamine in 81 % yield as a colorless oil. (Ref. 7001)	Chemically synthesized. (Ref. 7001)			[7001]
174		Anandamide (18:3, n-6)	N-cis-6,9,12-octadecatrienoylethanolamine	XPR7003	Keizo Waku		C₂₀H₃₅NO₂	321.497		Binding to the brain cannabinoid receptor (CB1) Ki (nM)= 4600300 (Ref. 7001)	oil (Ref. 7001)				soluble in organic solvent (Ref. 7001)				¹H NMR (CDCl3) d6.13 (br s 1H), 5.29-5.41 (m, 6H), 3.71 (t, J=5.1 Hz, 2H), 3.41 (q, J=5.1 Hz, 2H), 2.80 (t, J=5.7 Hz, 4H), 2.20 (t, J=8.1 Hz, 2H), 2.00-2.12 (m, 4H), 1.60-1.70 (m, 4H), 1.31 (brs 6H), 0.88 (t, J=7.5Hz, 3H). (Ref. 7001)					This compound was synthesized from cis-octadecatrienoyl chloride and ethanolamine in 79 % yield as a colorless oil. (Ref. 7001)				[7001]
175		Anandamide (18:2, n-6)	N-cis-9-cis-12-Octadecadienoylethanolamine	XPR7004	Keizo Waku		C₂₀H₃₇NO₂	323.513		The binding of this compound to the brain cannabinoid receptor (CBl) was scarecely found Ki(nM)>2500(Ref. 7001)	oil (Ref. 7001)					soluble in organic solvents (Ref. 7001)			¹H NMR (CDCl3) d5.90 (br s 1H), 5.30-5.39 (m, 4H), 3.72 (t, J=5.1 Hz, 2H), 3,42 (q, J=5.4 Hz, 2H), 2.76 (t, J=5.7 Hz, 2H), 2.20 (t, J=8.1 Hz, 2H), 2.01-2.06 (m, 4H), 1.60-1.70 (m, 2H), 1.30 (br s 14H), 0.88 (t, J=7.2Hz, 3H). (Ref. 0001)					Anandamide (l8:2, n-6) was prepared from cis-9,cis-12-octadecadienoylchloride and ethanolamine in 84 % yield as a colorless oil. (Ref. 7001)	This compound was found in rat brain and testis. (Ref. 7002/7003)			[0001] / [7001] / [7002] / [7003]
176		Anandamide (20:3, n-3)	N-cis-11, 14,17-eicosatrienoylethanolamine	XPR7005	Keizo Waku		C₂₂H₃₉NO₂	349.551		Binding of this compound to the brain cannabinoid receptor (CB1)is scarecely found Ki (nM)> 10000(Ref. 7001)	oil (Ref. 7001)					soluble in organic solvent (Ref. 7001)			¹H NMR (CDCl3) d5.90 (br s 1H), 5.30-5.39 (m, 4H), 3.72 (t, J=5.1 Hz, 2H), 3.42 (q, J=5.4 Hz, 2H), 2.80 (t, J=5.7 Hz, 4H), 2.20 (t, J=8.l Hz, 2H), 2.01-2.12 (m, 4H), 1.56-1.67 (m, 4H), 1.26 (br s 10H), 0.97 (t, J=7.5 Hz, 3H). (Ref. 7001)					This compound was prepared from cis-11,14,17-eicosatrienoyl chloride and ethanolamine in 50 % yield as a colorless oil. (Ref. 7001)				[7001]
177		Anandamide (18:4, n-3)	N-cis-6,9,12,15-Octadecatetraenoylethanolamine	XPR7006	Keizo Waku		C₂₀H₃₃NO₂	319.482		Binding of this compound to the brain cannabinoid receptor (CB1) Ki (nM)>1000 (Ref. 7001)	oil (Ref. 7001)					soluble in organic solvent (Ref. 7001)			¹H NMR (CDCl3) d5.92 (br s 1H), 5.33-5.40 (m, 8H), 3.72 (t, J=5.1 Hz, 2H), 3.42 (q, J=5.2 Hz, 2H), 2.79-2.84 (m, 6H), 2.22 (t, J=7.8Hz, 2H), 2.02-2.12 (m, 4H), 1.60- 1.72 (m, 2H), 1.38-1.48 (m, 2H), 0.98 (t, J= 7.5 Hz, 3H). (Ref. 7001)					cis-6,9,12,15-Octadecatetraenoyl chloride and ethanolamine in 76 % yield as a colorless oil.(Ref. 7001)				[7001]
178		Anandamide (18:3, n-3)	N-cis-9,12,15-Octadecatrienoylethanolamine	XPR7007	Keizo Waku		C₂₀H₃₅N₀₂	303.505		Binding of this compound to the brain cannabinoid receptor (CB1) Ki (nM) = 4600300(Ref. 7001)	oil (Ref. 7001)				soluble in organic solvent (Ref. 7001)				¹H NMR (CDCl3) d6.13 (br s, 1H), 5.29-5.42 (m, 6H), 3.71 (t, J=5.1 Hz, 2H), 3.41 (q, J=5.1 Hz, 2H), 2.80 (t, J=5.7 Hz, 4H), 2.20 (t, J=8.1 Hz, 2H), 2.04-2.12 (m, 4H), 1.63 (t, J=6.9 Hz, 2H), 1.31 (br s 10H), 0.97 (t, J=7.5 Hz, 3H). (Ref. 7001)					This compound was prepared from cis-9,12,15-octadecatrienoyl chloride and ethanolaminein 74 .5% yield as a colorless oil. (Ref. 7001)	This compound was not found in rat brain and testis. (Ref. 0002/0003)			[0002] / [0003] / [7001]
179		Anandamide (20:5, n-3)	N-cis-5,8, 11,14,17-eicosapentaenoylethanolamine	XPR7008	Keizo Waku		C₂₂H₃₅N₀₂	327.527		Binding of this compound to the brain cannabinoid receptor (CB1) Ki (nM) = 162.313.6 (Ref. 7001)	oil (Ref. 7001)					soluble in organic solvent (Ref. 7001)			¹H NMR (CDCl3) d5.90 (br s 1H), 5.22-5.42 (m, 10H), 3.71 (t, J= 5.1 Hz, 2H), 3.41 (q, J=4.9 Hz, 2H), 2.79-2.86 (m, 8H), 2.05-2.22 (m, 6H), 1.60-1.72 (m, 2H), 0.97 (t, J=7.9 Hz, 3H) (Ref. 7001)					This compound was synthesized from cis-5,8,11,14,17-eicosapentaenoyl chloride and ethanolamine in 72% yield as a colorless oil. (Ref. 7001)				[7001]
180		Anandamide (22:6, n-3)	N-cis-4,7,10,13,16,19-docosahexanoylethanolamine	XPR7009	Keizo Waku		C₂₄H₃₇N₀₂	353.564		Binding of this compound to the brain cannabinoid receptor (CB1) Ki (nM) = 324.19.2 (Ref. 7001)	oil (Ref. 7001)					soluble in organic solvent (Ref. 7001)			¹H NMR (CDCl3) d5.90 (br s 1H), 5.28-5.42 (m, 12H), 3.72 (t, J=5.1 Hz, 2H), 3.41 (q, J=4.9 Hz, 2H), 2.77-2.88 (m, 10H), 2.42 (t, J=8.1 Hz, 2H), 2.22-2.30 (m, 2H), 2.02-2.14 (m, 2H), 0.97 (t,J=7.8 Hz, 3H) (Ref. 7001)					This compound was synthesized from docosahexanoyl chloride and ethanolamine in 65 % yield as a colorless oil. (Ref. 7001)				[7001]
181		Anandamide (20:l, n-9)	N-cis-11 -eicosaenoylethanolamine	XPR7010	Keizo Waku		C₂₂H₄₃N₀₂	335.590		Binding of this compound to the brain cannabinoid receptor (CB1), Ki (nM)>1000(Ref. 7001)	67 - 68C (Ref. 7001)					soluble in organic solvent (Ref. 7001)			¹H NMR (CDCl3) d5.90 (br s 1H), 5.32-5.36 (m, 2H), 3.70 (t, J=5.1 Hz, 2H), 3.40-3.42 (m, 2H), 2.18 8t, J=7.8 Hz, 2H), 1.96-2.02 (m, 4H), 1.54-1.63 (m, 6H), 0.86 (t, J=6.1 Hz, 3H). (Ref. 7001)					This compound was synthesized from cis-11-eicosaenoylchloride and ethanolamine in 70 % yield. (Ref. 7001)				[7001]
182		Anandamide (20:3, n-6)	dihomo-g-linolenoylethanol amide	XPR7011	Keizo Waku		C₂₂H₃₉NO₂	349.551		Binding of this compound to the brain cannabinoid receptor (CB1), Ki(nM)=53.4 5.5 (Ref. 7001)						colorless oil, soluble in organic solvent (Ref. 7001)								This compound was synthesized from di-homo-g-linoleoylchloride and ethanolamine. (Ref. 7001)				[7001]
183		Anandamide (22:4, n-6)	docosatetraenoylethanolamide	XPR7012	Keizo Waku		C₂₄H₄₁NO₂	375.588		Binding of this compound to the brain cannabinoid receptor CB1,Ki= 34.43.2 (Ref. 7001)	colorless oil (Ref. 7001)					soluble in organic solvent (Ref. 7001)								This compound was synthesized from docosatetraenoylchloride and ethanolamine. (Ref. 7001)				[7001]
184		Anandamide (16:0)	palmitoylethanolamide	XPR7013	Keizo Waku		C₁₈H₃₇NO₂	299.492		Binding of this compound to the brain cannabinoid receptor (CB1)was not found. (Ref. 7001)	100-101C (Ref. 7001)								¹H NMR (CDCl3) d6.00 (br s 1H), 3.72 (t, J=5.1 Hz, 2H),					This compound was synthesized from palmitoylchloride and ethanolamine in 79 % yield. (Ref. 7001)				[7001]
185			oleoylamide	XPR7014	Keizo Waku		C₂₀H₃₈NO₂	324.521		Binding of this compound to the brain cannabinoid receptor (CBl)was not found. (Ref. 7001)	74-75C(Ref. 7001)								¹H NMR (CDCl3) d5.42 (br s, 2H), 5.32-5.36 (m, 2H), 2.22 (t, J=7.8 Hz 2H), 1.98-2.02 (m,6H), 1.62-1.66 (m, 4H), 1.27-1.31 (m, 16H), 0.88 (t, J=6.9Hz, 3H). (Ref. 7001)					This compound was synthesized from oleic acid and ammonium hydroxide in 60 % yield.(Ref. 7001)				[7001]
186			cis-5,8,11,14-eicosatetrayoyl ethanolamide	XPR7015	Keizo Waku		C₂₂H₂₉NO₂	339.471		Binding of this compound to the brain cannabinoid receptor (CBl)was not found. (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d6.15 (br s 1H), 3.73 (t, J=					This compound was prepared from cis-5,8,11,14-eicosatetrayoic acid and ethanolamine in 64% yield.(Ref. 7001)				[7001]
187			anandamide 0-phosphate	XPR7016	Keizo Waku		C₂₂H₃₈NO₅P	427.515		Binding of this compound to the brain cannabinoid receptor (CBl),Ki(nM)= 190.811.1(Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.34-5.42 (m, 8H), 3.98 (br s 2H), 3.46 (br s 2H), 2.77-2.81 (m, 6H), 2.26 (t, J=6.8Hz, 2H), 2.00-2.06 (m, 4H), 1.60-1.69 (m, 2H), 1.29-1.42 (m, 6H), 0.88 (t, J=6.9Hz,3H) (Ref. 7001)					This compound was synthesized from N-hydroxysuccinimide ester of arachidonic acid and O-phosphoethanolamine in 60% yield. (Ref. 7001)				[7001]
188			N-arachidonoylglycine	XPR7017	Keizo Waku		C₂₂H₃₅NO₃	361.518		Binding of this compound to the brain cannabinoid receptor (CBl),Ki(nM)>10000(Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d6.25 (br s 1H), 5.30-5.37 (m, 8H), 4.05 (d, J=5.1Hz, 2H), 2.76-2.82 (m, 6H), 2.22 (t, J=7.8Hz, 2H), 2.04-2.18 (m, 2H), 1.70-1.82 (m, 4H), 1.25-1.35 (m, 6H), 0.89 (t, J=7.1Hz, 3H) (Ref. 7001)					This compound was synthesized from arachidonoylchloride and glycine in potassium hydroxide solution. Yield is 34%. (Ref. 7001)				[7001]
189			N-arachidonoyl-D-serine	XPR7018	Keizo Waku		C₂₃H₃₇NO₄	391.544		Binding of this compoud to the brain cannabinoid receptor (CBl), Ki(nM)>10000 (Ref. 7001)	colorless oil (Ref. 7001)				d= -8.9(C=1,CHCl3)(Ref. 7001)				¹H NMR (CD3OD) d5.30-5.43 (m, 8H), 4.49 (t, J=4.8Hz, 1H), 3.80-3.88 (m, 2H), 2.80-2.86 (m, 6H), 2.30 (t, J=6.6Hz, 2H), 2.04-2.18 (m, 4H), 1.66-1.72 (m, 2H), 1.29-1.39 (m, 6H), 0.90 (t, J=6.9Hz, 3H) (Ref. 7001)					This compound was synthesized from D-serine and N-hydroxysuccinimide ester of arachidonic acid. The yield was 60 %. (Ref. 7001)				[7001]
190			N-arachidonoyl-L-serine	XPR7019	Keizo Waku		C₂₃H₃₇NO₄	391.544		Binding of this compound to the brain cannabinoid receptor(CB1),Ki(nM)>10000 (Ref. 7001)	colorless oil (Ref. 7001)				d= +8.9 (Ref. 7001)				¹H NMR (CD3OD) d5.33-5.40 (m, 8H), 4.50 (t, J=4.8 Hz, 1H), 3.78-3.90 (m, 2H), 2.80-2.86 (m, 6H), 2.29 (t, J=6.6Hz, 2H), 2.04-2.18 (m, 4H), 1.64-1.72 (m, 2H), 1.29-1.39 (m, 6H), 0.90 (t, J=7.2Hz, 3H) (Ref. 7001)					this compound was synthesized from D-serine and N-hydroxysuccinimide ester of arachidonicacid. yield is 55%. (Ref. 7001)				[7001]
191			N-ethyl arachidonoyl amide	XPR7020	Keizo Waku		C₂₂H₃₇NO	331.535		Binding of this compound to the brain cannabinoid receptor (CB1), Ki (nM)= 34.02.7 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.31-5.41 (m, 8H), 3.22-3.34 (m, 2H), 2.78-2.84 (m, 6H), 1.68-1.78 (m, 4H), 1.22-1.40 (m, 6H), 1.13 (t, J=7.3, 3H), 0.88 (t, J=7.1H, 3H) (Ref. 7001)					This compound was synthesized from arachidonoyl chloride and ethylamine, yield is 73 %. (Ref. 7001)				[7001]
192			N-methyl arachidonoyl amide	XPR7021	Keizo Waku		C₂₂H₃₇NO	331.535		Binding of this compound to the brain cannabinoid receptor (CB1),Ki(nM)= 60.07.4 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.80 (br s, lH), 5.30-5.40 (m, 8H), 2.78-2.85 (m, 9H), 2.03-2.19 (m, 6H), 1.66-1.76 (m, 2H), 1.25-1.34 (m, 6H), 0.88 (t, J=9Hz, 3H) (Ref. 7001)					This compound was synthesized from arachidonoylchloride and methylamine.Yield is 67 %.(Ref. 7001)				[7001]
193			arachidonoyl amide	XPR7022	Keizo Waku		C₂₂H₃₃NO	327.504		Binding of this compound to the brain cannabinoid receptor (CBl),Ki (nM)>1000 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.82 (br s, lH), 5.31-5.42 (m, 8H), 2.79-2.85 (m, 6H), 2.23 (t, J=8.1Hz, 2H), 2.04-2.15 (m, 4H), 1.70-1.77 (m, 2H), 1.25-1.38 (m, 6H), 0.89 (t, J=6.8Hz,3H). (Ref. 7001)					This compound was synthesized from arachidonyl chloride and ammonium hydroxide. Yield is 80 %. (Ref. 7001)				[7001]
194			N-propylarachidonoyl amide	XPR7023	Keizo Waku		C₂₃H₃₉NO	345.562		Binding of this compound to the rat brain cannabinoid receptor (CBl), Ki= 11.72.1 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.62 (br s, 1H), 5.26-5.38 (m, 8H), 3.13 (q, J=6Hz, 2H), 2.62-2.80 (m, 6H), 2.10 (t, J=7.3Hz, 2H), 1.96-2.06 (m, 4H), 1.56-1.66 (m, 2H), 1,38-1.48 (m, 2H), 1.20-1.32 (m, 6H), 0.79-0.86 (m, 6H) (Ref. 7001)					This compound was synthesized from arachidonoylchloride and n-propylamine.Yield 71%. (Ref. 7001)				[7001]
195			N-isopropyl arachidonoyl amide	XPR7024	Keizo Waku		C₂₃H₃₉NO	345.562		Binding of this compound to the rat brain cannabinoid receptor (CBl), Ki (nM)= 13.61.1(Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.30-5.44 (m, 8H), 4.02-4.12 (m, 1H), 2.76-2.86 (m, 6H), 2.02-2.16 (m, 6H), 1.66-1.76 (m, 2H), 1.26-1.38 (m, 6H), 1.14 (d, J=6.6Hz, 6H), 0.89 (t, J=6.9Hz, 3H) (Ref. 7001)					This compound was synthesized from arachidonoylchloride and isopropylamine.Yield 46%.(Ref. 7001)				[7001]
196			N-butylarachidonoyl amide	XPR7025	Keizo Waku		C₂₄H₄₁NO	359.588		Binding of this compound to the brain cannabinoid receptor (CB1),Ki (nM)= 235.7l4.2 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.26-5.44 (m, 8H), 3.24 (q, J=6Hz, 2H), 2.76-2.86 (m, 6H), 2.02-2.22(m, 6H), 1.64-1.78 (m, 2H), 1.22-1.56 (m, 10H), 0.86-0.98 (m, 6H). (Ref. 7001)					This compound was synthesized from arachidonoylchloride and n-butylamine. Yield is 56%. (Ref. 7001)				[7001]
197			N-tert-butyl arachidonoyl amide	XPR7026	Keizo Waku		C₂₄H₄₁NO	359.588		Binding of this compound to the brain cannabinoid receptor (CBl),Ki(nM)>1000 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CCCl3) d5.30-5.40 (m,					This compound was synthesized from arachidonoyl chloride and tert-butylamine. Yield 72 % (Ref. 7001)				[7001]
198			N-amyl arachidohoyl amide	XPR7027	Keizo Waku		C₂₅H₄₃NO	373.615		Binding of this compound to the brain cannabinoid receptor (CBl),Ki(nM)>l000 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.70 (br s lH), 5.23-5.33 (m, 8H), 3.15 (q, J=3Hz, 2H), 2.71-2.77(m, 6H), 1.97-2.16 (m, 6H), 1.58-1.68 (m, 2H), 1.18-1.42 (m, l2H), 0.79-0.85 (m, 6H). (Ref. 7001)					This compound was synthesized from arachidonoylchloride and amylamine.Yield 70 % (Ref. 7001)				[7001]
199			N-(3-methylbutyl)arachidonoyl amide	XPR7028	Keizo Waku		C₂₅H₄₃NO	373.615		Binding of this compound to the brain cannabinoid receptor (CBl),Ki(nM)= 575.135.3 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.30-5.42 (m, 8H), 3.26 (q, J=3Hz, 2H), 2.76-2.86 (m, 6H), 2.02-2.20 (m, 6H), 1.68-1.78 (m, 2H), 1.54-1.64 (m, lH), 1.26-1.40 (m, 8H), 0.82-0.96 (m, 9H) (Ref. 7001)					This compound was synthesized from arachidonoylchloride and isoamylamine.Yield 7l % (Ref. 7001)				[7001]
200			N-(1,1-dimethylpropyl)arachidonoyl amide	XPR7029	Keizo Waku		C₂₅H₄₃NO	373.615		Binding of this compound to the brain cannabinoid receptor (CBl),Ki(nM)= 446.740.3 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.28-5.38 (m, 8H), 5.10 (br s, lH), 2.67-2.82 (m, 6H), 2.04-2.12 (m, 6H), 1.66-1.76 (m, 4H), 1.24-1.32 (m, l2 H), 0.81-0.90 (m, 6H). (Ref. 7001)					This compound was synthesized from arachidonoyl chloride and 1,1-dimethylpropylamine.Yield 58 % (Ref. 7001)				[7001]
201			N-((R-(-)-1-methylpropyl)arachidonoyl amide	XPR7030	Keizo Waku		C₂₄H₄₁NO	359.588		Binding to the brain cannabinoid receptor (CBl),Ki(nM)= 239.963.8 (Ref. 7001)	colorless oil (Ref. 7001)				d= -7.08(c=l,EtOH)(Ref. 7001)				¹H NMR (CDCl3) d5.30-5.42 (m, 8H), 5.20 (br s, lH), 3.86-4.00 (m, lH), 2.75-2.86 (m, 6H), 2.00-2.20 (m, 6H), 1.65-1.80 (m, 2H), 1.22-1.50 (m, 8H), 1.10 (d, J=7.5Hz, 3H),0.82-0.92 (m, 6H). (Ref. 7001)					This compound was synthesized from arachidonoyl chloride and (R)-(-)-sec-butylamine.Yield 63 % (Ref. 7001)				[7001]
202			N-((S)-(+)-1-methylpropyl)arachidonoyl amide	XPR7031	Keizo Waku		C₂₄H₄₁NO	359.588		Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 377.255.4 (Ref. 7001)	colorless oil (Ref. 0001)				d= +7.08 (C=1, EtOH) (Ref. 0001)				¹H NMR (CDCl3) d5.30-5.42 (m, 8H), 5.22 (br s, lH), 3.88-3.98 (m, lH), 2.75-2.90 (m, 6H), 2.00-2.20 (m, 6H), 1.65-1.76 (m, 2H), 1.22-1.50 (m, 8H), 1.12 (d, J=7.5Hz, 3H), 0.82-0.96 (m, 6H). (Ref. 7001)					This compound was synthesized from arachidonoylchloride and (S)-(+)-sec-butylamine. Yield 55%. (Ref. 7001)				[0001] / [7001]
203			N-(3-hydroxypropyl)arachidonoylamide	XPR7032	Keizo Waku		C₂₃H₃₉NO₂	361.561		Binding to the brain cannabinoid receptor (CBl),Ki(nM)= 29.90.4(Ref. 7001)	colorless oil (Ref. 0001)								¹H NMR (CDCl3) d6.42 (br s lH), 5.22-5.38 (m, 8H), 3.90 (br s, lH), 3.54 (t, J=5.5 Hz, 2H), 3.32 (q, J=6Hz, 2H), 2.62-2.80 (m, 6H), 1.92-2.18 (m, 6H), 1.50-1.70 (m, 4H), 1.20-1.3 (m, 6H), 0.90 (t, J=7Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonoyl chloride and 3-amino-l-propanol. Yield 68%. (Ref. 7001)				[0001] / [7001]
204			N-(1,1-dimethyl-2-hydroxyethyl)arachidonoyl amide	XPR7033	Keizo Waku		C₂₄H₄₁NO₂	375.588		Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 161.834.1 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.50 (br s, 1H), 5.28-5.40 (m,8H), 3.57 (s, 2H), 2.78-2.90 (m, 6H), 2.02-2.20 (m, 6H), 1.62-1.74 (m, 2H), 1.20-1.40 (m, 12H), 0.89 (t, J=7.1Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonoyl chloride and 2-amino-2-methyl-l-propanol.Yield 48 %. (Ref. 7001)				[7001]
205			N-(5-hydroxypentyl)arachidonoyl amide	XPR7034	Keizo Waku		C₂₅H₄₃NO₂	389.614		Binding to the rat brain cannabinoid receptor (CBl), Ki(nM)= 497.427.1 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.60 (br s lH), 5.22-5.42 (m, 8H), 3.64 (t, J=5.5Hz, 2H), 3.20-3.32 (m, 2H), 2.76-2.89 (m, 6H), 2.00-2.22 (m, 6H), 1.90 (br s lH), 1.20-1.80 (series of m, l4H), 0.89 (t, J=7.1Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonoylchloride and 5-amino-l-pentanol. Yield 6l %. (Ref. 7001)				[7001]
206			N-(2-methoxyethyl)arachidonoyl amide	XPR7035	Keizo Waku		C₂₃H₃₉NO	345.562		Binding to the rat brain cannabinoid receptor (CBl), Ki(nM)= 85.23.8 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.80 (br s lH), 5.30-5.42 (m, 8H), 3.45 (d, J=2.1Hz, 4H), 3.35 (s, 3H), 2.75-2.85 (m, 6H), 2.00-2.20 (m, 6H), 1.62-1.80 (m, 2H), 1.20-1.40 (m, 6H), 0.89 (t, J=6.8Hz, 3H) (Ref. 7001)					This compound was synthesized from arachidonoylchloride and methoxyethylamine. Yield 4l%. (Ref. 7001)				[7001]
207			N'-arachidonoyl-N''-diethylethylenediamine	XPR7036	Keizo Waku		C₂₆H₄₆N₂O	402.656		Binding to the brain cannabinoid receptor (CBl), Ki(nM)>1000 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d6.10 (br s lH), 5.26-5.42 (m, 8H), 3.22-3.30 (m, 2H), 2.76-2.90 (m, 6H), 2.50-2.62 (m, 6H), 1.66-1.80 (m, 2H), 1.20-1.40 (m, 6H), 1.02 (t, J=7.1Hz, 6H), 0.89 (t, J=6.5Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonoylchloride and N,N-diethylenediamine. Yield 70 %. (Ref. 7001)				[7001]
208			N,N-dimethyl arachidonoyl amide	XPR7037	Keizo Waku		C₂₂H₃₇NO	331.535		Binding to the rat brain cannabinoid receptor (CBl), Ki(nM)>1000 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.24-5.44 (m, 8H), 2.99 (s, 3H), 2.94 (s, 3H), 2.76-2.86 (m, 6H), 2.31 (t, J=7Hz, 2H), 2.00-2.18 (m, 4H), 1.66-1.78 (m, 2H), 1.20-1.38 (m, 6H), 0.89 (t, J=7.lHz, 3H)(Ref. 7001)					This compound was synthesized from arachidonoyl chloride and dimethylamine. Yield 59 %. (Ref. 7001)				[7001]
209			N,N-diethyl arachidonoyl amide	XPR7038	Keizo Waku		C₂₄H₄₁NO	359.588		Binding to the rat brain cannabinoid receptor (CBl), Ki(nM)>1000 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.30-5.42 (m, 8H), 3.20-3.42 (m, 4H), 2.76-2.86 (m, 6H), 2.29 (t, J=7.l Hz, 2H), 2.00-2.20 (m, 4H), 1.60-1.80 (m, 2H), 1.22-1.40 (m, 6H), 1.04-1.20 (m, 6H), 0.90 (t, J=6.1Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonoyl chloride and diethylamine. Yield 66%.(Ref. 7001)				[7001]
210			N-methyl -N-(2-hydroxyethyl)arachidonoyl amide	XPR7039	Keizo Waku		C₂₃H₃₉NO₂	361.561		Binding to the brain cannabinoid receptor (CBl), Ki(nM)>10000 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.30-5.42 (m, 8H), 3.77 (t, J=5Hz, 2H), 3.55 (t, J=7.8Hz,2H), 2.04-2.15 (m, 4H), 1.64-1.75 (m, 2H), 1.25-1.38 (m, 6H), 0.89 (t, J=6.8Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonoyl chloride and 2-(methylamino)ethanol. Yield 75 %.(Ref. 7001)				[7001]
211			N-ethyl -N-(2-hydroxyethyl)arachidonoyl amide	XPR7040	Keizo Waku		C₂₄H₄₁NO₂	375.588		Binding to the brain cannabinoid receptor (CBl), Ki(nM)>10000 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.31-5.42 (m, 8H), 3.75 (t, J=4.6 Hz, 2H), 3.51 (t, J=4.6Hz, 2H), 3.34(q, J=7.l Hz, 2H), 3.34 (q, J=7.l Hz, 2H), 2.79-2.86 (m, 6H), 2.35 (t, J=7.8Hz, 2H), 2.04-2.15(m, 4H), 1.64-1.77 (m, 2H), 1.25-1.40 (m, 6H), 1.19 (t, J=7.l Hz, 3H), 0.89 (t, J=7.lHz, 3H).(Ref. 7001)					This compound was synthesized from arachidonoyl chloried and 2-(ethylamino)ethanol. Yield 83 %. (Ref. 7001)				[7001]
212			N-propyl -N-(2-hydroxyethyl)arachidonoyl amide	XPR7041	Keizo Waku		C₂₅H₄₃NO₂	389.614		Binding to the brain cannabinoid receptor (CBl), Ki(nM)>10000 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.30-5.42 (m, 8H), 3.76 (t, J=4.9 Hz, 2H), 3.52 (t, J=4.4 Hz, 2H), 3.24 (t, J=8.l Hz, 2H), 2.79-2.86 (m, 6H), 2.35 (t, J=8.l Hz, 2H), 2.02-2.20 (m, 4H), 1.54-1.76 (m, 4H), 1.25-1.38 (m, 6H), 0.86-0.89 (m, 6H). (Ref. 7001)					This compound was synthesized from arachidonoyl chloride and 2-(propylamino)ethanol. Yield 6l %. (Ref. 7001)				[7001]
213			N,N-(di-2-hydroxyethyl)arachidonoylamide	XPR7042	Keizo Waku		C₂₄H₄₁NO₃	391.587		Binding to the brain cannabinoid receptor (CBl), Ki>10000 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.60-5.42 (m, 8H), 3.83 (t, J=4.9Hz, 2H), 3.77 (t, J=5.lHz, 2H), 3.54(t, J=5.1Hz, 2H), 3.49 (t, J=4.9Hz, 2H), 2.77-2.86 (m, 6H), 2.40 (t, J=7.3Hz, 2H), 2.02-2.16 (m, 4H), 1.69-1.76 (m, 2H), 1.25-1.38 (m, 6H), 0.88 (t, J=6.6Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonoyl chloride and diethanolamine. Yield 45 %. (Ref. 7001)				[7001]
214			N-hydroxy -N-arachidonoyl amide	XPR7043	Keizo Waku		C₂₀H₃₃NO	303.482		Binding to the brain cannabinoid receptor (CBl), Ki (nM)>1000 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.30-5.43 (m, 8H), 2.78-2.86 (m, 6H), 2.02-2.17 (m, 6H), l.70-1.78(m, 2H), 1.22-1.38 (m, 6H), 0.89 (t, J=6.9 Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonoyl chloride and hydroxylamine hydrochloride.Yield 49%. (Ref. 7001)				[7001]
215			()-N-(1-methyl-2-hydroxy-2-phenylethyl)arachidonoyl amide	XPR7044	Keizo Waku		C₂₉H₄₃NO₂	437.657		Binding to the brain cannabinoid receptor (CBl), Ki(nM)>1000 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d7.27-7.35 (m, 5H), 5.54 (br s , lH), 5.63-5.41 (m, 8H), 4.84 (br s, lH),4.31-4.36 (m, lH), 3.60 (br s, lH), 2.78-2.85 (m, 6H), 2.01-2.22 (m, 6H), 1.67-1.77 (m, 2H),1.25-1.37 (m, 6H), 1.01 (d, J=7.l Hz, 3H), 0.89 (t, J=7.l Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonoylchloride and ()phenylpropanolamine.Yield 67 %. (Ref. 7001)				[7001]
216			a-methyl anandamide	XPR7045	Keizo Waku		C₂₃H₃₉NO	345.562		Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 32.55.1 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d6.10 (br s lH), 5.22-5.40 (m, 8H), 3.75 (t, J=5.1Hz, 2H), 3.42 (q, J=4.9 Hz, 2H), 2.74-2.86 (m, 6H), 2.20-2.30 (m, lH), 2.00-2.12 (m, 4H), 1.68-1.80 (m, lH), 1.20-1.50 (m, 6H), 1.16 (d, J=6.6Hz, 3H), 0.89 (t, J=6.9Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonic acid and ethanolamine. Yield 82 %. (Ref. 7001)				[7001]
217			a,a-dimethyl anandamide	XPR7046	Keizo Waku		C₂₄H₄₁NO	359.588		Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 25.52.8 (Ref. 7001)	colorless oil(Ref. 7001)								¹H NMR (CDCl3) d6.10 (br s, lH), 5.30-5.42 (m, 8H), 3.75 (t, J=5.l Hz, 2H), 3.42 (q, J=4.9Hz, 2H), 2.78-2.86 (m, 6H), 2.00-2.10 (m, 4H), 1.50-1.62 (m, 4H), 1.24-1.40 (m, 4H), 1.22 (s, 6H), 0.90 (t, J=6.9 Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonic acid and ethanolamine. Yield 47 %.(Ref. 7001)				[7001]
218			N-propyl a-methyl arachidonoyl amide	XPR7047	Keizo Waku		C₂₄H₄₁NO	359.588		Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 7.40.2 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.20-5.45 (m,					This compound was synthesized from arachidonic acid and propylamine. Yield 84 %. (Ref. 7001)				[7001]
219			N-propyl a,a-dimethylarachidonoyl amide	XPR7048	Keizo Waku		C₂₅H₄₃NO	373.615		Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 6.90.7 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.60 (br s, lH), 5.30-5.40 (m, 8H), 3.20-3.23 (m, 2H), 2.79-2.84 (m, 6H), 2.00-2.10 (m, 4H), 1.20-1.60 (series of m, 10H), 1.15 (s, 6H), 0.86-0.94 (m, 6H). (Ref. 7001)					This compound was synthesized from arachidonic acid and propylamine. Yield 70 %. (Ref. 7001)				[7001]
220			N-isopropyl a-methyl arachidonoyl amide	XPR7049	Keizo Waku		C₂₄H₄₁NO	359.588		Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 8.41.1 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.30-5.42 (m, 8H), 4.02-4.14 (m, lH), 2.76-2.90 (m, 6H), 1.92-2.12 (m, 5H), 1.10-1.60 (series of m, 17H), 0.89 (t, J=6.9Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonic acid and isopropylamine. Yield 85 %. (Ref. 7001)				[7001]
221			N-isopropyl a,a-dimethylarachidonoyl amide	XPR7050	Keizo Waku		C₂₅H₄₃NO	373.615		Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 7.20.1 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.20-5.50 (m, 9H), 4.04-4.14 (m, lH), 2.76-2.90 (m, 6H), 1.90-2.15 (m, 4H), 1.10-1.60 (series of m, 20H), 0.90 (t, J=6.9Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonic acid and isopropylamine. Yield 78 %. (Ref. 7001)				[7001]
222			N-((S)-(+)-2-hydroxypropyl) a ,a-dimethylarachidonoyl amide	XPR7051	Keizo Waku		C₂₅H₄₃NO₂	389.614		Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 46.62.2 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d5.95 (br s, lH), 5.30-5.42 (m, 8H), 3.92-3.96 (m, lH), 3.40-3.50 (m, lH), 3.02-3.23 (m, lH), 2.70-2.95 (m, 7H), 2.20-2.28 (m, lH), 2.00-2.15 (m, 4H), 1.70-1.75 (m, 2H) 1.20-1.52 (series of m, 14H), 0.89 (t, J=6.7Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonic acid and (S)-(+)-l-amino-2-propanol. Yield is 57 %. (Ref. 7001)				[7001]
223			N-((R)-(-)-1-methyl-2-hydroxyethyl)a,a-dimethylarachidonoyl amide	XPR7052	Keizo Waku		C₂₅H₄₃NO₂	389.614		Binding to the brain cannabinoid receptor (CBl), Ki(nM)= 3l.l1.0 (Ref. 7001)	colorless oil(Ref. 7001)								¹H NMR (CDCl3) d5.80 (br s, lH), 5.30-5.42 (m, 8H), 4.01-4.12 (m, lH), 3.60-3.68 (m, lH), 3.50-3.55 (m, lH), 2.98-3.01 (m, lH), 2.76-2.84 (m, 6H), 1.90-2.10 (m, 4H), 1.15-1.62 (series of m, l7H), 0.90 (t, J=7.1Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonic acid and (R)-(-)-2-amino-l-propanol. Yield is 45 %. (Ref. 7001)				[7001]
224			N-((S)-(+)-1-methyl-2-hydroxyethyl)a,a-dimethylarachidonoyl amide	XPR7053	Keizo Waku		C₂₅H₄₃NO₂	389.614		binding to the brain cannabinoid receptor (CBl), Ki(nM)= 191.424.5 (Ref. 7001)	colorless oil(Ref. 7001)								¹H NMR (CDCl3) d5.80 (br s, lH), 5.30-5.42 (m, 8H), 4.01-4.12 (m, lH), 3.60-3.68 (m, lH),3.50-3.55 (m, lH), 2.98-3.01 (m, lH), 2.76-2.84 (m, 6H), 1.90-2.10 (m, 4H), 1.15-1.62 (series of m, l7H), 0.90 (t, J=7.l Hz, 3H). (Ref. 7001)					This compound was synthesized from arachidonic acid and (S)-(+)-2-amino-l-propanol. Yield is 44 %. (Ref. 7001)				[7001]
225			N-(1-methyl-2-hydroxyethyl)arachidonoylamide (R)	XPR7054	Keizo Waku		C₂₃H₃₉NO₂	361.561		[Table 7054] (Ref. 7009)	colorless liquid (Ref. 7012>.				d= +10.9 (Ref. 7012)				¹H NMR (200 MHz, CDCl3) d(TMS)5.57 (m, 1H), 5.47-5.30 (m, 8H), 4.14-4.02 (m, 1H), 3.71-3.48 (m, 2H), 2.84-2.81 (m, 6H), 2.24-2.01 (m, 6H), 1.77-1.65 (m, 2H), 1.39-1.26 (m, 6H), 1.17 (d, J=3.46Hz, 3H), 0.89 (t, J=6.12Hz, 3H) (Ref. 7012)			Rf 0.3(5% MeOH/CHCl3) (Ref. 0012)		This compound was synthesized from arachidonic acid and (R)-(-)-2-amino-l-propanol in 69% yield. (Ref. 7012)				[0012] / [7009] / [7012]
226			N-(2-methyl-2-hydroxyethyl)arachidonoylamide (S)	XPR7055	Keizo Waku		C₂₃H₃₉NO₂	361.561		[Table 7055] (Ref. 7009)	colorless oil (Ref. 7012)				d= +9.44 (Ref. 7012)				¹H NMR (200 MHz, CDCl3) d(TMS)6.42 (m, 1H), 5.46-5.30 (m, 8H), 3.93-3.85 (m, 1H), 3.47-3.36 (m, 1H), 3.16-3.03 (m, 1H), 2.83-2.80 (m, 6H), 2.26-2.01 (m, 6H), 1.78-1.64 (m, 2H), 1.39-1.25 (m, 6H), 1.18 (d, J=3.18Hz, 3H), 0.89 (t, J=6.43 Hz, 3H) (Ref. 7012)			Rf 0.3(5% MeOH/CHCl3)		This compound was synthesized from arachidonic acid and (S)-(+)-l-amino-2-propanol in 63% yield. (Ref. 7012)				[7009] / [7012]
227			(16,16-dimethyldocosa-cis-5,8,11,14-tetraenoyl)ethanolamine	XPR7056	Keizo Waku		C₂₆H₄₅NO₂	403.641		[Table 7056] (Ref. 7056)									¹H NMR (CDCl3) d5.79 (br s, lH, NH), 5.38 (m, 6H, 5,6,8,9,11,12-vinyl-H), 5.21 (m, 2H, 14,15-vinyl-H), 3.44, 3.43 (s&d overlapped, 4H, OCH2-CH2-N), 3.36 (s, 3H, OCH3), 2.92 (t, 2H, J=6.0Hz, 13-CH2), 2.80 (m, 4H, 7,10-CH2), 2.18 (t, 2H, J=7.7Hz, 2-CH2), 2.12 (m, 2H, 4-CH2), 1.71(p, 2H, J=7.7Hz, 3-CH2), 1.25 (m, 10H, 17-21CH2), 1.08 (s, 6H, gem-Me2), 0.86 (m, 3H, 22-CH2) (Ref. 7009)					This compound was synthesized from 16,16-dimethyldocosa-cis-5,8,11,14-tetraenoic methyl ester, NaCN and ethanolamine by heating (50C in methanol)in a sealed tube. Yield 82 %. (Ref. 7009)				[7009]
228			(R)-(16,16-dimethyldocosa-cis-5,8,11,14-tetraenoyl)-1'-hydroxy-2'-propylamine	XPR7057	Keizo Waku		C₂₇H₄₇NO₂	417.668		[Table 7057] (Ref. 7009)									¹H NMR (CDCl3) d5.73 (br d, 1H, J=6.5Hz, NH), 5.36 (m, 6H, 5,6,8,9,11,12-vinyl-H), 5.21 (m, 2H, 14,15-vinyl-H), 4.04 (m, lH, N-CH), 3.64 (br m, 1H, OCH3), 3.52 (br m, 1H, OCH'), 3.18 (br s, 1H, OH), 2.91 (t, 2H, J=5.9Hz, 13-CH2), 2.79 (m, 4H, 7,10-CH2), 2.18 (t, 2H, J=7.6Hz,2-CH2), 2.08 (m, 2H, 4-CH2), 1.71 (p, 2H, J=7.4 Hz, 3-CH2), 1.27 (m, 10H, 17-21-CH2), 1.15 (d, 3H, J=6.8Hz, N-C-CH3), 1.08 (s, 6H, gem-Me2), 0.86 (m, 3H, 22-CH3) (Ref. 7009)					(R)-(16,16-Dimethyldocosa-cis-5,8,11,14-tetraenoic methyl ester (methyl alcohol solution), NaCN and (R)-(-)-2-amino-1-propanol are heated at 50C overnight in a sealed tube. Yield 77%. (Ref. 7009)				[7009]
229			(S)-(16,16-dimethyldocosa-cis-5,8,11,14-tetraenoyl)-2'-hydroxy-1'-propylamine	XPR7058	Keizo Waku		C₂₇H₄₇NO₂	417.668		[Table 7058] (Ref. 7009)									¹H NMR (CDCl3) d5.99 (br s, 1H, NH), 5.36 (m, 6H, 5,6,8,9,11,12-vinyl-H), 5.18 (m, 2H,14,15-vinyl-H), 3.89 (m, 1H, O-CH), 3.42 (m, 1H, NCH), 3.10 (m, 1H, NCH'), 2.92 (t,2H, J=6.1Hz, 13-CH2), 2.81 (m, 4H, 7,10-CH2), 2.21 (t, 2H, J=7.6Hz, 2-CH2), 2.09 (m, 2H, 4-CH2), 1.71 (p, 2H, J=7.5Hz, 3-CH2), 1.25 (br, m, 10H, 17-21-CH2), 1.18 (d, 3H, J=6.3Hz, O-C-CH3), 1.08 (s, 6H, gem-Me2), 0.87 (m, 3H, 22-CH39) (Ref. 7009)					A methanol solution of the corresponding ester , NaCN and (S)-(+)-1-amino-2-propanol are heated 2-days in a hot block at 50C. Yield 65%. (Ref. 7009)				[7009]
230			(16,16-dimethyldocosa-cis-5,8,11,14-tetraenoyl)-2'-methoxyethylamine	XPR7059	Keizo Waku		C₂₇H₄₇NO₂	417.668		[Table 7059] (Ref. 7009)									¹H NMR (CDCl3) d5.79 (br s, 1H, NH), 5.38 (m, 6H, 5,6,8,9,11,12-vinyl-H), 5.21 (m, 2H, 14,15-vinyl-H), 3.44,3.43 (s & d overlapped, 4H, O-CH2-CH2-N), 3.36 (s, 3H, OCH3), 2.92 (t, 2H, J=6.0Hz, 13-CH2), 2.80 (m, 4H, 7,10-CH2), 2.18 (t, 2H, J=7.7Hz, 2-CH2), 2.12(m, 2H, 4-CH2), 1.71 (p, 2H, J=7.7Hz, 3-CH2), 1.25 (m, 10H, 17-21-CH2), 1.08 (s, 6H, gem-Me2), 0.86 (m, 3H, 22-CH2) (Ref. 7009)					A methanol solution of the corresponding ester, NaCN and 2-methoxyethylamine heated 2-days in a hot block at 50C.Yield 4l %. (Ref. 7009)				[7009]
231			(16,16-dimethyldocosa-cis-5,8,11,14-tetraenoyl)propylamine	XPR7060	Keizo Waku		C₂₇H₄₇NO	401.668		[Table 7060] (Ref. 7009)									¹H NMR (CDCl3) d5.36 (overlap m, 7H, NH, 5,6,8,9,11,12-vinyl-H), 5.21 (m, 2H, 14,15-vinyl-H), 3.21 (q, 2H, J=6.7Hz, N-CH2), 2.92 (t, 2H, J=5.9Hz, 13-CH2), 2.80 (m, 4H, 7,10-CH2), 2.16,2.12 (t, m, 4H, J=7.6Hz, 2&4-CH2), 1.71 (p, 2H, J=7.4Hz, 3-CH2), 1.52 (hx, 2H, J=7.3Hz, 2'-CH2), 1.25 (m, 10H, 17-21-CH2), 1.08 (s, 6H, gem-Me2), 0.91,0.87 (t,m, 6H, 3'-CH3, 22-CH3) (Ref. 7009)					Heating a methanolic solution of the corresponding ester, NaCN and n-propylamine for 2days in a hot block at 50C.Yield 44%. (Ref. 7009)				[7009]
232			N-((R)-(-)-2-hydroxypropyl)a,a-dimethylarachidonoylamide	XPR7061	Keizo Waku		C₂₅H₄₃NO₂	389.614		Binding to the brain cannabinoid receptor(CBl), Ki(nM)= 153.930.0 (Ref. 7001)	colorless oil (Ref. 7001)								¹H NMR (CDCl3) d 5.95 (br s, l H), 5.30-5.42 (m, 8H), 3.92-3.96 (m, 1H), 3.40-3.50 (m, 1H), 3.02-3.23 (m, 1H), 2.70-2.95 (m, 7H), 2.20-2.28(m, 1H), 2.00-2.15 (m, 4H), 1.70-1.75 (m, 2H), 1.20-1.52 (series of m, 14H), 0.89 (t, J=6.7 Hz, 3H), (Ref. 7001)					This compound was synthesized from arachidonic acid and (R)-(-)-l-amino-2-propanolyield 63%. (Ref. 7001)				[7001]
233			N-eicosanoylethanolamine	XPR7062	Keizo Waku		C₂₂H₄₅NO₂	355.598		[Table 7062] (Ref. 7010)														This compound was synthesized from eicosanoylchloride and ethanolamine. (Ref. 7010)				[7010]
234			N-eicosanoyl-(2'-fluoroethyl)amine	XPR7063	Keizo Waku		C₂₂H₄₄NOF	357.589		[Table 7063] (Ref. 7010)														This compound was synthesized from eicosanoylchloride and 2-fluoroethylamine. (Ref. 7010)				[7010]
235			arachidonoyl-N-(4-benzenesulfonamide)amide	XPR7064	Keizo Waku		C₂₆H₃₇N₂₀₂S	3210.999		[Table 7064] (Ref. 7010)														This compound was synthesized from arachidonoylchloride and 4-aminobenzenesulfonamide. (Ref. 7010)				[7010]
236			arachidonoyl-(4'-bromobenzenesulfon)amide	XPR7065	Keizo Waku		C₂₆H₃₅O₃SBr	507.524		[Table 7065] (Ref. 7010)														This compound was synthesized from the reaction of arachidonic acid and p-bromobenzene sulfonamide in the presence of l-ethyl-3-[3-(dimethylamino)propyl]carbodiimide and 4-dimethylaminopyridene in methylene chloride at room temperature. (Ref. 7010)				[7010]
237			arachidonoylmorpholine	XPR7066	Keizo Waku		C₂₄H₃₅NO	353.541		[Table 7066] (Ref. 7010)														This compound was synthesized from arachidonoylchloride and morpholine. (Ref. 7010)				[7010]
238			arachidonoyl-(2'-(4-bezenesulfonamide)ethyl)amide	XPR7067	Keizo Waku		C₂₉H₄₂NSO₃	484.715		[Table 7067] (Ref. 7010)														This compound was synthesized from arachidonoylchloride and 2-(4'-benzenesulfonamide)ethylamine. (Ref. 7010)				[7010]
239			arachidonoyl-(2'-phenoxyethyl)amide	XPR7068	Keizo Waku		C₂₉H₄₁NO₂	435.641		[Table 7068] (Ref. 7010)														This compound was synthesized from arachidonoylchloride and phenoxyethylamine. (Ref. 7010)				[7010]
240			arachidonoyl-(2'-fluoroethyl)amide	XPR7069	Keizo Waku		C₂₃H₃₆NOF	361.536		[Table 7069] (Ref. 7010)														This compound was synthesized from arachidonoylchloride and 2-fluoroethylamine. (Ref. 7010)				[7010]
241			2-methylarachidonoyl-(2'-fluoroethyl)amide	XPR7070	Keizo Waku		C₂₃H₃₈NOF	363.552		[Table 7070] (Ref. 7010)														This compound was synthesized from 2-methylarachidonoylchloride and 2-fluoroethylamine. (Ref. 7010)				[7010]
242			2-isopropylarachidonoyl-(2'-hydroxyethyl)amide	XPR7071	Keizo Waku		C₂₆H₄₃NO₂	401.625		[Table 7071] (Ref. 7010)														This compound was synthesized from 2-isopropylarachidonoylchloride and ethanolamine. (Ref. 7010)				[7010]
243			5,8,11,14-all-cis-heneicosatetraenoylethanolamine	XPR7072	Keizo Waku		C₂₃H₄₀NO₂	362.569		[Table 7072] (Ref. 7011)	oil (Ref. 7011)								d0.88 (t, J=7.5Hz, 3H), 1.3 (br s 8H), 1.60-2.30 (m, 8H), 2.82 (br s, 7H), 3.30-3.50 (m, 2H), 3.65-3.80 (m, 2H), 5.20-5.55 (m, 8H), 6.05 (br s, 1H) (Ref. 7011)					This compound was synthesized from 5,8,11,14-all-cis-Heneicosatetraenoylchloride and ethanolamine. Yield 76 %. (Ref. 7011)				[7011]
244			5,8,11,14-all-cis-docosatetraenoylethanolamine	XPR7073	Keizo Waku		C₂₄H₄₂NO₂	376.596		[Table 7073] (Ref. 7011)	oil (Ref. 7011)								d 0.88 (t, J=7.5Hz, 3H), 1.29 (br s, 10H), 1.60-1.90 (m, 2H), 2.0-2.30 (m, 6H), 2.65-2.95 (m, 7H), 3.30-3.55 (m, 2H), 3.65-3.80 (m, 2H), 5.20-5.55 (m, 8H), 5.9 (br s, 1H) (Ref. 7011)					This compound was synthesized from 5,8,11,14-all-cis-docosatetraenoylchloride and ethanolamine. Yield 35 %. (Ref. 7011)				[7011]
245			5,8,11,14-all-cis-tricosatetraenoylethanolamine	XPR7074	Keizo Waku		C₂₅H₄₄NO₂	390.622		[Table 7074] (Ref. 7011)	oil (Ref. 7011)								d0.89 (t, J=7.5Hz, 3H), 1.29 (br s, 12H), 1.60-1.90 (m, 2H), 2.05-3.50 (m, 6H), 2.65-2.95 (m, 7H), 3.30-3.50 (m, 2H), 3.60-3.85 (m, 2H), 5.20-5.55 (m, 8H), 5.95 (br s, 1H) (Ref. 7011)					This compound was synthesized from 5,8,11,14-tricosatetraenoyl chloride and ethanolamine. Yield 57%. (Ref. 7011>				[7011]
246			5,8,11,14-all-cis-tetracosanoylethanolamide	XPR7075	Keizo Waku		C₂₆H₄₆NO₂	404.649		[Table 7075] (Ref. 7011)	oil (Ref. 7011)								d0.88 (J=7.5Hz, 3H), 1.28 (br s, 14H), 1.60-1.90 (m, 2H), 2.05-2.30 (m, 6H), 2.75-2.95 (m, 7H), 3.35-3.55 (m, 2H), 3.65-3.80 (m, 2H), 5.20-5.55 (m, 8H), 5.85 (br s, 1H). (Ref. 7011)					This compound was synthesized from 5,8,11,14-tetracosanoylchloride and ethanolamine. Yield 66%. (Ref. 7011)				[7011]
247			16,16-dimethyl-5,8,11,14-all-cis-docosatetraenoylethanolamine	XPR7076	Keizo Waku		C₂₆H₄₅NO₂	403.641		[Table 7076] (Ref. 7011)	yellow oil (Ref. 7011)								d0.88 (t, J=5.4Hz, 3H), 1.09 (s, 6H), 1.27 (br s, 10H), 1.62-1.86 (m, 2H), 2.03-2.30 (m, 4H), 2.68-2.98 (m, 6H), 3.40 (dt, J=4.0, 6.3Hz, 2H), 3.71 (t, J=5.0Hz, 2H), 5.13-5.41 (m, 8H), 6.19 (br s, 1H) (Ref. 7011)					This compound was synthesized from 16,16-dimethyl-5,8,11,14-docosatetraenoylchloride and ethanolamine. Yield 93%. (Ref. 7011)				[7011]
248			17,17-dimethyl-5,8,11,14-all-cis-docosatetraenoylethanolamide	XPR7077	Keizo Waku		C₂₆H₄₆NO₂	404.649		[Table 7077] (Ref. 7011)	oil (Ref. 7011)								d0.88 (s, 6H), 0.90 (t, J=7.5Hz, 3H), 1.20 (br s, 8H), 1.60-2.30 (m, 8H), 2.70-2.95 (m, 7H), 3.35-3.55 (m, 2H), 3.65-3.80 (m, 2H), 5.20-5.60 (m, 8H), 6.05 (br s, 1H) (Ref. 7011)					This compound was synthesized from 17,17-dimethyl-docosatetraenoylchloride and ethanolamine. Yield 61%. (Ref. 7011)				[7011]
249			17,17-dimethyl-5,8,11,14-all-cis-heneicosanoylethanolamine	XPR7078	Keizo Waku		C₂₅H₄₄NO₂	390.622		[Table 7078] (Ref. 7011)	oil (Ref. 7011)								d0.85 (s, 6H), 0.90 (t, J=7.5Hz, 3H), 1.25 (br s, 6H), 1.65-2.30 (m, 8H), 2.65-2.95 (m, 7H), 3.30-3.50 (m, 2H), 3.65-3.80 (m, 2H), 5.20-5.50 (m, 8H), 6.05 (br s, 1H) (Ref. 7011)					This compound was synthesized from 17,17-dimethyl-5,8,11,14-heneicosanoyl chloride and ethanolamine. Yield 40%. (Ref. 7011)				[7011]
250			17-methyl-5,8,11,14-all-cis-docosatetraenoylethanolamine	XPR7079	Keizo Waku		C₂₅H₄₄NO₂	390.622		[Table 7079] (Ref. 7011)	oil (Ref. 7011)								d0.90 (m, 6H), 1.28 (br s, 9H), 1.60-2.35 (m, 8H), 2.65-2.95 (m, 7H), 3.30-3.50 (m, 2H), 3.65-3.85 (m, 2H), 5.20-5.60 (m, 8H), 5.95 (br s, 1H) (Ref. 7011)					This compound was synthesized from 17-methyl-5,8,11,14-docosatetraenoylchloride and ethanolamine. Yield 64%. (Ref. 7011)				[7011]
251			()-2,16,16-trimethyl-5,8,11,14-all-cis-docosatetraenoyl-2'-fluoroethyamine	XPR7080	Keizo Waku		C₂₇H₄₇FNO	420.667		[Table 7080] (Ref. 7011)	yellow oil (Ref. 7011)								d0.88 (t, J=4.0Hz, 3H), 1.09 (s, 6H), 1.16 (d, J=6.9Hz, 3H), 1.26 (br s, 10H), 1.39-2.34 (m, 5H), 2.72-2.98 (m, 6H), 3.58 (ddt, J=29.0, 5.0, 4.5Hz, 2H), 4.49 (dt, J=47.5, 4.6Hz, 2H), 5.13-5.53 (m, 8H), 5.82 (br s, 1H) (Ref. 7011)					This compound was synthesized from 2,16,16-trimethyl-5,8,11,14-all-cis-docosatetraenoylchloride and2-fluoroethanolamine.Yield 65%. (Ref. 7011)				[7011]
252			()-2,16,16-trimethyl-5,8,11,14-all-cis-tricosatetraenoyl-2'-fluoroethylamine	XPR7081	Keizo Waku		C₂₈H₄₈NOF	433.685		[Table 7081] (Ref. 7011)	oil (Ref. 7011)								d0.88 (t, 6.0Hz, 3H), 1.09 (s, 6H), 1.16 (d, J=6.8Hz, 3H), 1.25 (br s, 10H), 1.39-2.40 (m, 5H), 2.81-2.97 (m, 6H), 3.57 (ddt, J=28.5, 5.2, 4.5Hz, 2H), 4.49 (dt, J=47.4, 4.6Hz, 2H), 5.13-5.52 (m, 8H), 5.86 (br s, 1H) (Ref. 7011)					This compound was synthesized from 2,16,16-trimethyl-5,8,11,14-tricosatetraenoylchloride and 2-fluoroethylamine. Yield 57%. (Ref. 7011)				[7011]
253			()-2,16,-dimethyl-5,8,11,14-all-cis-docosatetraenoyl-2'-fluoroethylamine	XPR7082	Keizo Waku		C₂₆H₄₅FNO	406.640		[Table 7082] (Ref. 7011)	oil (Ref. 7011)								d0.88 (t, J=6.0Hz, 3H), 0.94 (d, J=6.2Hz, 2H), 1.16 (d, J=6.8Hz, 3H), 1.25 (br s, 10H), 1.36-2.60 (m, 6H), 2.70-2.90 (m, 6H), 3.60 (ddt, J=28.5, 5.1, 4.6Hz, 2H), 4.49 (dt, J=47.4, 4.8Hz, 2H), 5.15-5.60 (m, 8H), 5.81 (br s, 1H) (Ref. 7011)					This compound was synthesized from 2,16,dimethyl-5,8,11,14-docosatetraenoylchloride and 2-fluoroethylamine. Yield 37%. (Ref. 7011)				[7011]
254			()-2,17,17,-trimethyl-5,8,11,14-all-cis-docosatetraenoyl-2'-fluoroethylamine	XPR7083	Keizo Waku		C₂₇H₄₇FNO	420.667		[Table 7083] (Ref. 7011)	oil (Ref. 7011)								d0.85 (s, 6H), 0.90 (t, J=6.0Hz, 3H), 1.15 (d, J=7.0Hz, 3H), 1.25 (br s, 8H), 1.40-2.40 (m, 7H), 2.70-2.95 (m, 6H), 3.58 (ddt, J=28.5, 5.2, 4.5Hz, 2H), 4.50 (dt, J=47.4, 4.6 Hz, 2H), 5.20-5.55 (m, 8H), 5.85 (br s, 1H) (Ref. 7011)					This compound was synthesized from 2,17,17,-trimethyl-5,8,11,14-docosatetraenoylchloride and 2-fluoroethylamine. Yield 72%. (Ref. 7011)				[7011]
255			()-2,17,-dimethyl-5,8,11,14-all-cis-docosatetraenoyl-2'-fluoroethylamine	XPR7084	Keizo Waku		C₂₆H₄₄FNO	405.632		[Table 7084] (Ref. 7011)	oil (Ref. 7011)								d0.80-0.98 (m, 6H), 1.15 (d, J=6.5Hz, 3H), 1.25 (br s, 8H), 1.38-2.40 (m, 8H), 2.65-3.0 (m, 6H), 3.60 (ddt, J=28.5, 5.2, 4.6Hz, 2H), 4.50 (dt, J=47.5, 4.8Hz, 2H), 5.20-5.55 (m, 8H), 5.80 (br s, 1H) (Ref. 7011)					This compound was synthesized from 2,17,-dimethyl-5,8,11,14-docosatetraenoylchloride and 2-fluoroethylamine. Yield 69%. (Ref. 7011)				[7011]
256			()-2-methyl-5,8,11,14-all-cis-tricosatetraenoyl-2'-fluoroethylamine	XPR7085	Keizo Waku		C₂₆H₄₅FNO	406.640		[Table 7085] (Ref. 7011)	oil (Ref. 7011)								d0.88 (t, J=6.0 Hz, 3H), 1.13 (d, J=7.5Hz, 3H), 1.25 (br s, 12H), 1.38-2.40 (m, 7H), 2.70-2.95 (m, 6H), 3.60 (ddt, J=28.5, 5.2, 4.5Hz, 2H), 4.50 (dt, J=47.5, 4.5Hz, 2H), 5.20-5.60 (m, 8H), 5.80 (br s, 1H) (Ref. 7011)					This compound was synthesized from 2-methyl-5,8,11,14-tricosatetraenoylchloride and 2-fluoroethylamine. Yield 72%. (Ref. 7011)				[7011]
257		2-Arachidonoylglycerol	2-Mono((all Z)-5', 8', 11', 14'-eicosatetraenoyl)glycerol	XPR7086	Keizo Waku	2-AG	C₂₃H₃₈O₄	378.545		Effect of 2-arachidonoylglycerol on the specific binding of CP55940 to rat synaptosomal membrane. Ki= 3.1M (Ref. 7014)The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by 2-arachidonoylglycerol is demonstrated as follows. (Ref. 7014) [Table 7086]						soluble in the organic solvent(Ref. 0014)						2-arachidonoylglycerol was purified by TLC using petroleum ether:diethylether:acetic acid(20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)	This compound was distributed in rat brain (Ref. 7014) and canine gut (Ref. 7017).	2-Arachidonoyl-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and arachidonic anhydride. 2-arachidonoylglycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85C under vacuum for 3 min. (Ref. 7014)	2-arachidonoylglycerol was easily hydrolyzed in the rat brain to arachidonic acid and glycerol.(Ref. 7013)			[0014] / [7013] / [7014] / [7017]
258		1-Arachidonoylglycerol	1-Mono((all Z)-5', 8', 11', 14'-eicosatetraenoyl)glycerol	XPR7087	Keizo Waku	1-AG	C₂₃H₃₈O₄	378.545		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by 1-arachidonoylglycerol is demonstrated as follows. (Ref. 7014) [Table 7087]												1-arachidonoylglycerol was purified by TLC using petroleum ether:diethylether:acetic acid(20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)		1-Arachidonoyl-sn-glycerol was synthesized from 2,3-O-isopropyridene-sn-glycerol and arachidonic acid anhydride using dimethylaminopyridine as a catalyst. The purified l-arachidonoyl-2,3-isopropyrideneglycerol was treated with boric acid and boric acid trimethylester, at 85C under vacuum for 3 min, to yield 1-arachidonoylglycerol. (Ref. 7014)				[7014]
259		3-Arachidonoylglycerol	3-Mono((all Z)-5', 8', 11', 14'-eicosatetraenoyl)glycerol	XPR7088	Keizo Waku	3-AG	C₂₃H₃₈O₄	378.545		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by 3-arachidonoylglycerol is demonstrated as follows. (Ref. 7014) [Table 7088]												3-arachidonoylglycerol was purified by TLC using petroleum ether:diethylether:acetic acid(20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)		3-Arachidonoyl-sn-glycerol was synthesized from 1,2-O-isopropyridene-sn-glycerol and arachidonic acid anhydride using dimethylaminopyridine as a catalyst. The purified l,2-isopropyrideneglycerol-3-arachidonoylglycerol was treated with boric acid and boric acid trimethylester, at 85C under vacuum for 3 min, to yield 3-arachidonoylglycerol. (Ref. 7014)				[7014]
260		Ether-linked analogue of 2-arachidonoylglycerol	2-O-((all Z)-5',8',11',14'-Eicosatetraenyl)glycerol	XPR7089	Keizo Waku	Ether type 2-AG	C₂₃H₄₀O₃	364.562		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by 2-eicosatetraenylglycerol is demonstrated as follows. (Ref. 7014) [Table 7089]												2-Eicosatetraenylglycerol was purified by TLC (ethyl acetate as solvent, Rf, 0.48). (Ref. 7014)		2-Eicosatetraenyl-1,3-benzylideneglycerol was obtained by condensating eicosatetraenyl iodide and 1,3-benzylideneglycerol using dimethylformamide as the solvent and Ag₂O and tetra-n-butylammonium iodide as catalysts. 2-Eicosatetraenylglycerol was prepared from 2-eicosatetraenyl-1,3-benzylideneglycerol by treatment of boric acid and boric acid trimethylester. (Ref. 7014)				[7014]
261		Ether-linked analogue of 1-arachidonoylglycerol	1-O-((all Z)-5',8',11',14'-Eicosatetraenyl)glycerol	XPR7090	Keizo Waku	Ether type 1-AG	C₂₃H₄₀O₃	364.562		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by 1(3)-eicosatetraenylglycerol is demonstrated as follows. (Ref. 0014) [Table 7090]												1(3)-Eicosatetraenylglycerol was purified by TLC (ethyl acetate as solvent, Rf, 0.48). (Ref. 7014)		1(3)-Eicosatetraenyl-1,2-O-isopropylideneglycerol was obtained by condensating eicosatetraenyl iodide and 1,2-O-isopropylideneglycerol using dimethylformamide as the solvent and Ag₂O and tetra-n-butylammonium iodide as catalysts. 1(3)-Eicosatetraenylglycerol was prepared from 1(3)-eicosatetraenyl-1,2-O-isopropylideneglycerol by treatment of boric acid and boric acid trimethylester. (Ref. 7014)				[0014] / [7014]
262		Methylene-linked analogue of 2-arachidonoylglycerol	2-Hydroxymethyl (all Z)-7,10,13,16-docosatetraen-1-ol	XPR7091	Keizo Waku	Methylene linked 2-AG	C₂₃H₄₀O₂	348.563		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014) [Table 7091]												The Rf value for the methylene-linked analogue of 2-arachidonoylglycerol in the TLC system using hexane:ethyl acetate (6:4) as the developing solvent was 0.15. (Ref. 7017)		The eicosatetraenol iodide and diethyl malonate were mixed and refluxed for 4 hr in a mixture of tetrahydrofuran and dimethylformamide. The diethylmalonate derivative was reduced in dry diethylether with LiAlH4. (Ref. 7014)				[7014] / [7017]
263			2-Hydroxypropyl arachidonate	XPR7092	Keizo Waku		C₂₃H₃₈O₃	362.546		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014) [Table 7092]												This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (65:35:19) as the solvent system (Rf, 0.20) (Ref. 7014)		2-Oxopropylarachidonate was prepared from hydroxyacetone and arachidonic anhydride. The resultant 2-oxopropyl arachidonate was treated with NaBH4 to yield 2-hydroxypropylarachidonate. (Ref. 7014)				[7014]
264			3-Hydroxypropyl arachidonate	XPR7093	Keizo Waku		C₂₃H₃₈O₃	362.546		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014) [Table 7093]												This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.58). (Ref. 7014)		This compound was prepared from 1,3-propanediol and arachidonic anhydride using dimethylaminopyridine as a catalyst and purified by TLC. (Ref. 7014)				[7014]
265		2-eicosatetraynoyl(n-6)glycerol	2-Mono(5',8',11',14'-eicosatetraynoyl)glycerol	XPR7094	Keizo Waku		C₂₃H₃₀O₄	370.482		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014) [Table 7094]												This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)		2-Eicosatetraynoyl-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and eicosatetraynoyl anhydride. 2-Eicosatetraynoylglycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85 C under vacuum for 3 min. (Ref. 7014)				[7014]
266		2-oleoylglycerol	2-Mono(9'-octadecenoyl)glycerol	XPR7095	Keizo Waku		C₂₁H₄₀O₄	356.540		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014) [Table 7095]												This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)		2-Oleoyl-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and oleoyl anhydride. 2-Oleoylglycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85C under vacuum for 3 min. (Ref. 7014)				[7014]
267		2-linoleoylglycerol	2-Mono((all Z)-9',12'-octadecadienoyl)glycerol	XPR7096	Keizo Waku		C₂lH₃₈O₄			The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014) [Table 7096]												This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)		2-Linoleoyl-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and linoleoyl anhydride. 2-Linoleoylglycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85C under vacuum for 3 min. (Ref. 7014)				[7014]
268		2-g-linolenoylglycerol	2-Mono((all Z)-6',9',12'-octadecatrienoyl)glycerol	XPR7097	Keizo Waku		C₂₁H₃₆O₄	352.508		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014) [Table 7097]												This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)		2-gLinolenoyl-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and glinolenoyl anhydride. 2-gLinolenoylglycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85C under vacuum for 3 min. (Ref. 7014)				[7014]
269		2-eicosatrienoyl(n-3)glycerol	2-Mono((all Z)-11',14',17'-eicosatrienoyl)glycerol	XPR7098	Keizo Waku		C₂₃H₄₀O₄	380.561		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014) [Table 7098]												This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)		2-Eicosatrienoyl(n-3)-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and eicosatrienoyl(n-3) anhydride. 2-Eicosatrienoyl(n-3)glycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85C under vacuum for 3 min. (Ref. 7014)				[7014]
270		2-eicosatrienoyl(n-6)glycerol	2-Mono((all Z)-8',11',14',-eicosatrienoyl)glycerol	XPR7099	Keizo Waku		C₂₃H₄₀O₄	380.561		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014) [Table 7099]												This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)		2-Eicosatrienoyl(n-6)-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and eicosatrienoyl(n-6) anhydride. 2-Eicosatrienoyl(n-6)glycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85C under vacuum for 3 min. (Ref. 7014)				[7014]
271		2-eicosatrienoyl(n-9)glycerol	2-Mono((all Z)-5',8',11',-eicosatrienoyl)glycerol	XPR7100	Keizo Waku		C₂₃H₄₀O₄	380.561		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014) [Table 7100]												This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)		2-Eicosatrienoyl(n-9)-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and eicosatrienoyl(n-9) anhydride. 2-Eicosatrienoyl(n-9)glycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85C under vacuum for 3 min. (Ref. 7014)				[7014]
272		2-eicosapentaenoyl(n-3)glycerol	2-Mono((all Z)-5',8',11',14',17'-eicosapentaenoyl)glycerol	XPR7101	Keizo Waku		C₂₃H₃₆O₄	376.530		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014) [Table 7101]												This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)		2-Eicosapentaenoyl(n-3)-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and eicosapentaenoyl(n-3) anhydride. 2-Eicosapentaenoyl(n-3)glycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85C under vacuum for 3 min. (Ref. 7014)				[7014]
273		2-docosatetraenoyl(n-6)glycerol	2-Mono((all Z)-7',10',13',16'-docosatetraenoyl)glycerol	XPR7102	Keizo Waku		C₂₅H₄₂O₄	406.599		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014) [Table 7102]												This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)		2-Docosatetraenoyl(n-6)-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and docosatetraenoyl(n-6) anhydride. 2-Docosatetraenoyl(n-6)glycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85 C under vacuum for 3 min. (Ref. 7014)				[7014]
274		2-docosahexaenoyl(n-3)glycerol	2-Mono((all Z)-4',7',10',13',16',19'-docosahexaenoyl)glycerol	XPR7103	Keizo Waku		C₂₅H₃₈O₄	402.567		The increase of [Ca²⁺]in NG108-15 neuroblastoma x glioma hybrid cells by this compound is demonstrated as follows. (Ref. 7014) [Table 7103]												This compound was purified by TLC using petroleum ether:diethyl ether:acetic acid (20:80:1) as the solvent system (Rf, 0.23). (Ref. 7014)		2-Docosahexaenoyl(n-3)-1,3-benzylidene-sn-glycerol was synthesized from 1,3-benzylidine-sn-glycerol and docosahexaenoyl(n-3) anhydride. 2-Docosahexaenoyl(n-3)glycerol was synthesized by treatment the above compound by boric acid and boric acid trimethyl ester at 85 C under vacuum for 3 min. (Ref. 7014)				[7014]
275		N-oleoylethanolamine/N-oleoylethanolamide	N-(cis-9-octadecenoyl) ethanolamine/N-(hydroxyethyl) oleamide	XPR7501	Takehiko Yokomizo	OEA	C₂₀H₃₉NO₂	325.529		Causes a potent and persistent decrease in food intake and gain in body mass(Ref. 7503).						Soluble in ethanol and DMSO				HPLC/MS (Ref. 7504)					Synthesized from N-oleoyl-phosphatidylethanolamine by phosphodiesterase or from free oleic acid and ethanolamine by acyltransferase(Ref. 7501). Degraded by amidohydrolase(Ref. 7502).			[7501] / [7502] / [7503] / [7504]
276		clavulone I(Ref. 8001/8003)/claviridenone-d(Ref. 8002/8006)	methyl (4R,5Z,7E)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8001	Yasuji Yamada		C₂₅H₃₄O₇	446.533		Clavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8001)Clavulone I showed strong antiproliferative activity in the human myeloid leukemia (HL-60) cells (IC₅₀ 0.2 mg/ml). Clavulone arrests the cells in the G1-phase and inhibits the cell growth of HL-60 cells by inhibiting S-phase DNA synthesis.(Ref. 8009)Clavulone showed positive chronotropic action on the cultured myocardial cells.(Ref. 8014)					[a]_D -28.9(C 0.36, CHCl₃)(Ref. 8001)	Clavulones are soluble in MeOH, EtOH, CHCl₃ or hexane.	l_m_a_x(EtOH) 230 nm(e13600),292 nm(e17300)(Ref. 8001)	n_m_a_x(film)1730,1700,1635,and 1230cm^-¹(Ref. 8001)	¹H-NMR(270MHz,CDCl₃)dppm0.88(3H,t,J=6.7Hz),2.03(3H,s),2.05(3H,s),2.38(2H,t,J=7.7Hz),2.66(1H,dd,J=7,14.5Hz),2.97(1H,dd,J=7,14.5Hz),3.70(3H,s),5.22(1H,dt,J=10.9,7Hz),5.45(1H,dt,J=10.9,8Hz),5.78(1H,m),5.86(1H,t,J=10Hz),6.42(1H,d,J=6.3Hz),6.59(1H,dd,J=10,12.5Hz),7.25(1H,d,J=12.5Hz),7.47(1H,d,J=6.3Hz).(Ref. 8001)¹³C-NMR(67.8MHz,CDCl₃)dppm14.0(q),20.9(q),21.2(q),22.5(t),27.4(t),29.0(t),29.8(t),29.8(t),31.4(t),35.9(t),51.7(q),69.4(d),85.2(s),121.0(d),124.3(d),124.4(d),134.9(d),137.5(s),138.7(d),157.8(d),169.0(s),169.7(s),172.7(s),193.0(s).(Ref. 8001)		CDl_e_x_t(EtOH)(De)nm 248(+3.8),291(-5.0).(Ref. 8022)		Clavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8001/8002/8003/8006)	Clavulone I was synthesized from cyclopentadiene and methyl 3-chloroformylpropionate as a racemic form.(Ref. 8007)Clavulones were synthesized from L-(+)-diethyl tartarate and D-mannitol as a natural form.(Ref. 8008)Other synthesis of clavulone.(Ref. 8015/8016/8017)	The biosynthesis of clavulone is suggested to proceed from arachidonic acid via 8(R)-HEPETE and pre-clavulone A.(Ref. 8004/8005/8012/8013)			[8001] / [8002] / [8003] / [8004] / [8005] / [8006] / [8007] / [8008] / [8009] / [8012] / [8013] / [8014] / [8015] / [8016] / [8017] / [8022]
277		clavulone II(Ref. 8001/8003)/claviridenone-c(Ref. 8002/8006)	methyl (4R,5E,7E)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8002	Yasuji Yamada		C₂₅H₃₄O₇	446.533		Clavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8001)Clavulone showed positive chronotropic action on the cultured myocardial cells.(Ref. 8014)Clavulone II showed strong antiproliferative activity in the human myeloid leukemia (HL-60) cells (IC₅₀ 0.2 mg/ml).(Ref. 8019)Clavulone II was entrapped into lipid microspheres of 0.2 mm diameter to lipo-drug. Daily treatment with lipo-clavulone II (12.5 mg/kg/day, i.p.) on days 1 through 5 markedly prolonged the survival time (73% ILS) of mice inoculated with sarcoma 180 as compared with that of corresponding dose of respective free clavulone II.(Ref. 8021)					[a]_D +10.9(C 0.35, CHCl₃)(Ref. 8001)	Clavulones are soluble in MeOH, EtOH, CHCl₃, or hexane.	l_m_a_x(EtOH) 230 nm(e14500),292 nm(e19300) (Ref. 8001)	n_m_a_x(film)1730,1700,1640,and 1230cm^-¹(Ref. 8001)	¹H-NMR(270MHz,CDCl₃)dppm0.88(3H,t,J=6.9Hz),2.07(3H,s),2.08(3H,s),2.38(2H,t,J=7.5Hz),2.69(1H,dd,J=8,14.5Hz),2.88(1H,dd,J=7,14.5Hz),3.68(3H,s),5.22(1H,m),5.52(1H,dt,J=10.9,8Hz),5.42(1H,q,J=7Hz),6.02(1H,dd,J=7,14.5Hz),6.41(1H,d,J=6.3Hz),6.75(1H,dd,J=11.6,14.5Hz),6.87(1H,d,J=11.6Hz),7.47(1H,d,J=6.3Hz).(Ref. 8001)¹³C-NMR(67.8MHz,CDCl₃)dppm14.0(q),21.0(q),21.2(q),22.5(t),27.4(t),29.1(t),29.1(t),29.6(t),31.5(t),36.0(t),51.8(q),72.8(d),85.1(s),121.1(d),126.9(d),129.3(d),135.0(d),137.0(s),141.3(d),158.1(d),169.5(s),169.9(s),172.9(s),193.4(s).(Ref. 8001)		CDl_e_x_t(EtOH)(De)nm 250(+4.2),293(-3.4).(Ref. 8022)		Clavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8001/8002/8003/8006)	Clavulone II was synthesized from cyclopentadiene and methyl 3-chloroformylpropionate as a racemic form.(Ref. 8007)Clavulones were synthesized from L-(+)-diethyl tartarate and D-mannitol as a natural form.(Ref. 8008)Other synthesis of clavulone.(Ref. 8010/8011/8015/8016/8017/8018)	The biosynthesis of clavulones is suggested to proceed from arachidonic acid via 8(R)-HEPETE and pre-clavulone A.(Ref. 8004/8005/8012/8013)			[8001] / [8002] / [8003] / [8004] / [8005] / [8006] / [8007] / [8008] / [8010] / [8011] / [8012] / [8013] / [8014] / [8015] / [8016] / [8017] / [8018] / [8019] / [8021] / [8022]
278		clavulone III(Ref. 8001/8003)/claviridenone-b(Ref. 8002/8006)	methyl (4R,5E,7Z)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8003	Yasuji Yamada		C₂₅H₃₄O₇	446.533		Clavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8001)Clavulone showed positive chronotropic action on the cultured myocardial cells.(Ref. 8014)					[a]_D +45.5(C 0.22, CHCl₃)(Ref. 8001)	Clavulones are soluble in MeOH, EtOH, CHCl₃, or hexane.	l_m_a_x(EtOH) 230 nm(e17200),295 nm(e17600)(Ref. 8022)	n_m_a_x(film)1735,1690,1640,and 1230cm^-¹(Ref. 8022)	¹H-NMR(270MHz,CDCl₃)dppm0.88(3H,t,J=6.9Hz),2.04(3H,s),2.10(3H,s),2.39(2H,t,J=7.5Hz),2.66(1H,dd,J=7,14.5Hz),2.86(1H,dd,J=7,14.5Hz),3.67(3H,s),5.21(1H,dt,J=11,7Hz),5.52(1H,dt,J=11,8Hz),5.44(1H,q,J=6Hz),6.02(1H,dd,J=6,15.5Hz),6.36(1H,d,J=6.3Hz),6.52(1H,d,J=11.2Hz),7.50(1H,d,J=6.3Hz),7.74(1H,dd,J=11.2,15.5Hz).(Ref. 8001)¹³C-NMR(67.8MHz,CDCl₃)dppm14.0(q),21.0(q),21.7(q),22.5(t),27.4(t),29.1(t),29.2(t),29.8(t),31.5(t),35.6(t),51.7(q),72.5(d),85.3(s),121.4(d),126.5(d),133.4(d),134.8(d),135.7(s),141.0(d),156.1(d),169.7(s),170.1(s),173.1(s),194.1(s).(Ref. 8001)		CDl_e_x_t(EtOH)(De)nm 245(+3.4),297(-0.6).(Ref. 8022)		Clavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8001/8002/8003/8006)	Clavulones were synthesized from L-(+)-diethyl tartarate and D-mannitol as a natural form.(Ref. 8008)Other synthesis of clavulone.(Ref. 8010/8015/8016/8017/8018)	The biosynthesis of clavulones is suggested to proceed from arachidonic acid via 8(R)-HEPETE and pre-clavulone A.(Ref. 8004/8005/8012/8013)			[8001] / [8002] / [8003] / [8004] / [8005] / [8006] / [8008] / [8010] / [8012] / [8013] / [8014] / [8015] / [8016] / [8017] / [8018] / [8022]
279		clavulone IV(Ref. 8022)/claviridenone-a(Ref. 8002/8006)	methyl (4R,5Z,7Z)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8004	Yasuji Yamada		C₂₅H₃₄O₇	446.533		Clavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8001)Clavulone showed positive chronotropic action on the cultured myocardial cells.(Ref. 8014)					[a]_D -80.0(CHCl₃)(Ref. 8022)	Clavulones are soluble in MeOH, EtOH, CHCl₃, or hexane.	l_m_a_x(EtOH) 230 nm(e10600),295 nm(e9900)(Ref. 8022)	n_m_a_x(film)1730,1695,1640,and 1240cm^-¹(Ref. 8022)	¹H-NMR(270MHz,CDCl₃)dppm0.88(3H,t,J=6.9Hz),2.03(3H,s),2.07(3H,s),2.36(2H,t,J=7.5Hz),2.65(1H,dd,J=7.3,14.2Hz),2.83(1H,dd,J=8,14.2Hz),3.68(3H,s),5.27(1H,m),5.52(1H,m),5.73(1H,t,J=10.6Hz),5.83(1H,m),6.39(1H,d,J=5.9Hz),7.02(1H,d,J=12.5Hz),7.49(1H,d,J=5.9Hz),7.61(1H,t,J=11.5Hz).(Yamada Yasuji)¹³C-NMR(67.8MHz,CDCl₃)dppm14.0(q),21.1(q),21.6(q),22.5(t),27.4(t),29.1(t),29.6(t),29.8(t),31.5(t),36.1(t),51.7(q),68.1(d),85.0(s),121.5(d),126.0(d),127.9(d),134.8(d),136.5(d),136.6(d),137.0(s),156.7(d),169.9(s),170.1(s),172.9(s),194.2(s).(Yasuji Yamada)		CDl_e_x_t(EtOH)(De)nm 245(+1.2),290(-1.4).(Ref. 8022)		Clavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8003/8006/8022)	Clavulones were synthesized from L-(+)-diethyl tartarate and D-mannitol as a natural form.(Ref. 8008)Other synthesis of clavulone.(Ref. 8015/8016/8017)	The biosynthesis of clavulones is suggested to proceed from arachidonic acid via 8(R)-HEPETE and pre-clavulone A.(Ref. 8004/8005/8012/8013)			[8001] / [8002] / [8003] / [8004] / [8005] / [8006] / [8008] / [8012] / [8013] / [8014] / [8015] / [8016] / [8017] / [8022]
280		20-acetoxyclavulone I (Ref. 8024)	methyl (4R,5Z,7E)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-7-acetoxy-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8005	Yasuji Yamada		C₂₇H₃₆O₉	504.569		20-Acetoxyclavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8022)					[a]_D -31.1(C 0.09, CHCl₃)(Ref. 8024)	20-Acetoxyclavulones are soluble in MeOH, EtOH, CHCl₃, or hexane.	l_m_a_x(EtOH) 230 nm(e10900),288 nm(e13700)(Ref. 8024)	n_m_a_x(film)1735,1705,1640,and 1235cm^-¹(Ref. 8024)	¹H-NMR(270MHz,CDCl₃)dppm2.03(3H,s),2.05(6H,s),2.38(2H,t,J=7.5Hz),2.66(1H,dd,J=8,14.5Hz),3.00(1H,dd,J=7,14.5Hz),3.70(3H,s),4.04(2H,t,J=6.6Hz),5.22(1H,m),5.47(1H,m),5.79(1H,m),5.79(1H,m),5.84(1H,t,J=10.2Hz),6.42(1H,d,J=6.3Hz),6.58(1H,dd,J=10.2,12.5Hz),7.27(1H,d,J=12.5Hz), 7.47(1H,d,J=6.3Hz).(Ref. 8024)¹³C-NMR(67.8MHz,CDCl₃)dppm21.0(q,2C),21.3(q),25.6(t),27.3(t),28.5(t),29.0(t),29.8(t,2C),35.8(t),51.8(q),64.5(t),69.4(d),85.1(s),121.5(d),124.2(d),124.6(d),134.5(d),135.2(d),137.4(s),138.9(d),157.8(d),169.1(s),169.9(s),171.2(s),172.9(s),193.1(s).(Ref. 8024)		CDl_e_x_t(EtOH)(De)nm 247(+2.6),290(-3.6).(Ref. 8022/8024)		20-Acetoxyclavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8024)					[8022] / [8024]
281		20-acetoxyclavulone II (Ref. 8024)	methyl (4R,5E,7E)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-7-acetoxy-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8006	Yasuji Yamada		C₂₇H₃₆O₉	504.569		20-Acetoxyclavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8022)					[a]_D +3.7(C 0.54, CHCl₃)(Ref. 8024)	20-Acetoxyclavulones are soluble in MeOH, EtOH, CHCl₃, or hexane.	l_m_a_x(EtOH) 230 nm(e14200),292 nm(e18700)(Ref. 8024)	n_m_a_x(film)1730,1700,1640,and 1235cm^-¹(Ref. 8024)	¹H-NMR(270MHz,CDCl₃)dppm2.05(3H,s),2.07(3H,s),2.08(3H,s),2.38(2H,t,J=7.3Hz),2.69(1H,dd,J=7.6,16Hz),2.87(1H,dd,J=7.3,16Hz),3.68(3H,s),4.04(2H,t,J=6.9Hz),5.20(1H,m),5.41(1H,q,J=7Hz),5.51(1H,dt,J=11,7.3Hz),6.03(1H,dd,J=7,14.8Hz),6.41(1H,d,J=6.9Hz),6.74(1H,dd,J=12.2,14.8Hz),6.86(1H,d,J=12.2Hz),7.47(1H,d,J=5.9Hz).(Ref. 8024)¹³C-NMR(67.8MHz,CDCl₃)dppm21.0(q,2C),21.2(q),25.6(t),27.3(t),28.5(t),29.2(t,2C),29.5(t),36.0(t),51.8(q),64.4(t),72.8(d),85.0(s),121.5(d),126.8(d),129.3(d),134.5(d),135.0(d),136.8(s),141.3(d),158.1(d),169.5(s),169.9(s),171.2(s),172.9(s),193.3(s).(Ref. 8024)		CDl_e_x_t(EtOH)(De)nm 247(+2.6),295(-1.0).(Ref. 8022/8024)		20-Acetoxyclavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8024)					[8022] / [8024]
282		20-acetoxyclavulone III (Ref. 8024)	methyl (4R,5E,7Z)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-7-acetoxy-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8007	Yasuji Yamada		C₂₇H₃₆O₉	504.569		20-Acetoxyclavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8022)					[a]_D +26.4(C 0.86, CHCl₃)(Ref. 8024)	20-Acetoxyclavulones are soluble in MeOH, EtOH, CHCl₃, or hexane.	l_m_a_x(EtOH) 230 nm(e12400),295 nm(e12100)(Ref. 8024)	n_m_a_x(film)1730,1695,1640,and 1235cm^-¹(Ref. 8024)	¹H-NMR(270MHz,CDCl₃)dppm2.02(3H,s),2.05(3H,s),2.10(3H,s),2.39(2H,t,J=7.6Hz),2.62(1H,dd,J=7.6,14.2Hz),2.87(1H,dd,J=7.3,14.2Hz),3.68(3H,s),4.04(2H,t,J=6.9Hz),5.21(1H,m),5.44(1H,q,J=5.9Hz),5.51(1H,m),6.03(1H,dd,J=5.9,15.5Hz),6.36(1H,d,J=6.3Hz),6.52(1H,d,J=11.2Hz),7.50(1H,d,J=6.3Hz),7.47(1H,dd,J=11.2,15.5Hz).(Ref. 8024)¹³C-NMR(67.8MHz,CDCl₃)dppm21.0(q,2C),21.7(q),25.6(t),27.3(t),28.5(t),29.0(t),29.2(t),29.8(t),35.6(t),51.7(q),64.4(t),72.5(d),85.2(s),121.8(d),126.4(d),133.5(d),134.2(d),135.6(s),136.9(d),141.1(d),156.0(d),169.9(s),170.1(s),171.2(s),173.1(s),194.0(s).(Ref. 8024)		CDl_e_x_t(EtOH)(De)nm 243(+2.5),291(-0.6).(Ref. 8022/8024)		20-Acetoxyclavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8024)					[8022] / [8024]
283		chlorovulone I (Ref. 8025/8026)	methyl (5Z,7E)-7-[(R)-4-chloro-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8008	Yasuji Yamada		C₂₁H₂₉O₄Cl	380.905		Chlorovulone I showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC₅₀ 0.01 mg/ml, cytotoxic effect >0.1 mg/ml).(Ref. 8019/8023/8025)Chlorovulone I was entrapped into lipid microspheres of 0.2 mm diameter to lipo-drug. Daily treatment with lipo-chlorovulone I (1.6 mg/kg/day, i.p.) on days 1 through 5 markedly prolonged the survival time (135% ILS) of mice inoculated with sarcoma 180 as compared with that of corresponding dose of respective free chlorovulone I.(Ref. 8021)					[a]_D -1.2(C 0.17, CHCl₃)(Ref. 8025)	Chlorovulones are soluble in MeOH, EtOH, CHCl₃, or hexane.	l_m_a_x(EtOH) 243 nm(e14600),315 nm(e15100)(Ref. 8025)	n_m_a_x(CHCl₃)1705cm^-¹(Ref. 8025)	¹H-NMR(400MHz,CDCl₃)dppm0.88(3H,t,J=7.2Hz),1.30(6H,m),1.80(2H,quint.,J=7.4Hz),1.97(2H,brq,J=7.0Hz),2.35(2H,t,J=7.4Hz),2.42(2H,m),2.67(1H,ddd,J=0.5,7.8,14.2Hz),2.82(1H,ddd,J=0.5,7.5,14.2Hz),3.68(3H,s),5.22(1H,ttd,J=1.5,7.7,10.9Hz),5.54(1H,ttd,J=1.4,8.7,10.9Hz),6.11(1H,tdd,J=7.9,0.9,10.9Hz),6.77(1H,tdd,J=1.5,10.9,12.6Hz),7.21(1H,d,J=0.6Hz),7.33(1H,brd,J=12.6Hz).(Ref. 8025)¹³C-NMR(100MHz,CDCl₃)dppm13.9(q),22.4(t),24.3(t),27.1(t),27.3(t),29.0(t),31.4(t),33.2(t),33.6(t),51.6(q),77.7(s),121.7(d),123.8(d),127.9(d),134.8(d),136.4(s),137.9(s),143.6(d),154.0(d),173.6(s),187.7(s).(Ref. 8025)		CDl_e_x_t(EtOH)(De)nm 232(+7.6),265(-6.1),360(+3.1).(Ref. 8028)		Chlorovulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8025/8026)	Photoisomerization of chlorovulone I (fluoresent lamp, benzene, 40 hr) gave a mixture of chlorovulones I, II and III.(Ref. 8025)				[8019] / [8021] / [8023] / [8025] / [8026] / [8028]
284		chlorovulone II (Ref. 8025/8026)	methyl (5E,7E)-7-[(R)-4-chloro-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8009	Yasuji Yamada		C₂₁H₂₉O₄Cl	380.905		(-)-Chlorovulone II showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC₅₀ 0.01 mg/ml, cytotoxic effect >0.1 mg/ml).(Ref. 8023)					[a]_D +22.7(C 0.075, CHCl₃)(Ref. 8025)	Chlorovulones are soluble in MeOH, EtOH, CHCl₃, or hexane.	l_m_a_x(EtOH) 237 nm(e10000),312 nm(e10100)(Ref. 8025)	n_m_a_x(CHCl₃)3560,3300,1730,1705, and 1635cm^-¹(Yamada Yasuji)	¹H-NMR(400MHz,CDCl₃)dppm0.88(3H,t,J=7.1Hz),1.30(6H,m),1.82(2H,quint.,J=7.4Hz),1.96(2H,brq,J=7.5Hz),2.30(2H,t,J=7.5Hz),2.35(2H,t,J=7.4Hz),2.68(1H,brdd,J=7.9,14.3Hz),2.81(1H,brdd,J=7.5,14.3Hz),3.67(3H,s),5.23(1H,ttd,J=1.4,7.7,10.9Hz),5.55(1H,brtd,J=7.5,10.9Hz),6.28(1H,td,J=7.4,15.1Hz),6.77(1H,tdd,J=1.3,11.9,15.1Hz),7.03(1H,d,J=11.9Hz),7.20(1H,s).(Ref. 8025)				Chlorovulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8025/8026)	Photoisomerization of chlorovulone I (fluoresent lamp, benzene, 40 hr) gave a mixture of chlorovulones I, II and III.(Ref. 8025)(-)-Cholovulone II was synthesized from D-(-)-diethyl tartarate.(Ref. 8026)				[8023] / [8025] / [8026]
285		chlorovulone III (Ref. 8025/8026)	methyl (5E,7Z)-7-[(R)-4-chloro-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8010	Yasuji Yamada		C₂₁H₂₉O₄Cl	380.905							[a]_D +27.3(C 0.033, CHCl₃)(Ref. 8025)	Chlorovulones are soluble in MeOH, EtOH, CHCl₃, or hexane.	l_m_a_x(EtOH) 238 nm(e13200),315 nm(e11900)(Ref. 8025)	n_m_a_x(CHCl₃)1725,1700, and 1630cm^-¹(Yamada Yasuji)	¹H-NMR(400MHz,CDCl₃)dppm0.88(3H,t,J=7.1Hz),1.30(6H,m),1.81(2H,quint.,J=7.5Hz),2.00(2H,brq,J=6.9Hz),2.30(2H,brq,J=7.5Hz),2.35(2H,t,J=7.5Hz),2.55(1H,brdd,J=7.6,14.4Hz),2.67(1H,brdd,J=8.3,14.4Hz),3.68(3H,s),5.29(1H,ttd,J=1.7,7.6,10.9Hz),5.38(1H,brtd,J=7.4,10.9Hz),6.19(1H,td,J=7.1,15.7Hz),6.68(1H,d,J=11.4Hz),7.15(1H,s),7.56(1H,tdd,J=1.4,11.4,15.7Hz).(Ref. 8025)				Chlorovulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8025/8026)	Photoisomerization of chlorovulone I (fluoresent lamp, benzene, 40 hr) gave a mixture of chlorovulones I, II and III.(Ref. 8025)				[8025] / [8026]
286		chlorovulone IV (Ref. 8025/8026)	methyl (5Z,7Z)-7-[(R)-4-chloro-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8011	Yasuji Yamada		C₂₁H₂₉O₄Cl	380.905							12-O-acetylchlorovulone IV[a]_D -12(C 0.025, CHCl₃)(Ref. 8025)	Chlorovulones are soluble in MeOH, EtOH, CHCl₃, or hexane.			12-O-acetylchlorovulone IV¹H-NMR(400MHz,CDCl₃)dppm0.88(3H,t,J=7.2Hz),1.79(2H,quint.,J=7.4Hz),1.81(2H,quint.,J=7.5Hz),1.97(2H,brq,J=7.4Hz),2.04(3H,s),2.35(2H,t,J=7.4Hz),2.70(1H,brdd,J=7.1,14.3Hz),2.94(1H,brdd,J=7.4,14.3Hz),3.67(3H,s),5.21(1H,brq,J=10.8Hz),5.54(1H,brtd,J=7.4,10.8Hz),6.02(1H,brtd,J=8.8,10.8Hz),6.98(1H,d,J=12.0Hz),7.44(1H,s),7.55(1H,brt,J=12.0Hz).(Ref. 8025)				Chlorovulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8025/8026)					[8025] / [8026]
287		10,11-epoxychlorovulone I (Ref. 8027)	methyl (5Z,7E)-7-[(2S,3S,4R)-4-chloro-3,4-epoxy-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentanylidene]-5-heptenoate	XPR8012	Yasuji Yamada		C₂₁H₂₉O₅Cl	396.905		10,11-Epoxychlorovulone I showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC⁵⁰ 0.04 mg/ml, cytotoxic effect >0.3 mg/ml).(Ref. 8019/8027)					[a]_D -24.1(C 0.44, CHCl₃)(Ref. 8025)	10,11-Epoxychlorovulone I is soluble in MeOH, EtOH, CHCl₃, or hexane.	l_m_a_x(EtOH) 300 nm(e4300)(Ref. 8027)	n_m_a_x(CHCl₃)3580,1740, and 1625cm^-¹(Ref. 8027)	¹H-NMR(400MHz,CDCl₃)dppm0.88(3H,t,J=7.2Hz),1.80(2H,quint.,J=7.4Hz),1.99(2H,brq,J=7.7Hz),2.33(2H,t,J=7.3Hz),2.39(2H,m),2.72(1H,brd,J=7.3Hz),3.68(3H,s),3.96(1H,s),5.23(1H,m),5.60(1H,m),6.13(1H,tdd,J=7.9,10.9,1.0Hz),6.82(1H,tdd,J=1.6,10.9,12.5Hz),7.54(1H,d,J=12.5Hz).(Ref. 8027)	HRCIMS m/z 397.1815 (M+1, calcd for C₂₁H₃₀³⁵ClO₅, 397.1780)(Ref. 8027)			10,11-Epoxychlorovulone I was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8027)	Epoxidation of chlorovulone I with excess 5% aqueous sodium hypochlorite solution in DMF gave 10,11-epoxychlorovulone I.(Ref. 8027)				[8019] / [8025] / [8027]
288		bromovulone I (Ref. 8028)	methyl (5Z,7E)-7-[(R)-4-bromo-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8013	Yasuji Yamada		C₂₁H₂₉O₅Br	441.356		Bromovulone I showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC₅₀ 0.025 mg/ml, cytotoxic effect >0.4 mg/ml).(Ref. 8019/8023/8028)					[a]_D +6.0(C 0.05, MeOH)(Yamada Yasuji)	Bromovulone I is soluble in MeOH, EtOH, CHCl₃, or hexane.	l^E^t^O^H_m_a_x 247 nm(e12000),312 nm(e12000)(Ref. 8028)	n_m_a_x(CHCl₃)3300,1730, 1700, and 1630cm^-¹(Ref. 8028)	¹H-NMR(400MHz,CDCl₃)dppm0.89(3H,t,J=7.2Hz),1.30(6H,m),1.80(2H,quint.,J=7.4Hz),1.98(2H,brq,J=7.0Hz),2.36(2H,t,J=7.4Hz),2.42(2H,m),2.66(1H,brdd,J=7.8,14.9Hz),2.81(1H,brdd,J=7.6,14.9Hz),3.69(3H,s),5.22(1H,brtd,J=7.8,11.0Hz),5.55(1H,brtd,J=7.0,11.0Hz),6.11(1H,brtd,J=7.3,10.9Hz),6.77(1H,brdd,J=10.9,12.6Hz),7.35(1H,d,J=12.6Hz),7.43(1H,d,J=0.5Hz).(Ref. 8028)	EIMS m/z 424 and 426 (1:1)(Ref. 8028)	CDl_e_x_t(EtOH)(De)nm 235(+5.6),260(-3.0),360(+1.2).(Ref. 8028)		Bromovulone I was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8028)					[8019] / [8023] / [8028]
289		iodovulone I (Ref. 8028)	methyl (5Z,7E)-7-[(R)-4-iodoo-2-hydroxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8014	Yasuji Yamada		C₂₁H₂₉O₅I	488.356		Iodovulone I showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC⁵⁰ 0.06 mg/ml, cytotoxic effect >0.4 mg/ml).(Ref. 8019/8023/8028)					[a]_D +15.2(C 0.07, MeOH)(Yamada Yasuji)	Iodovulone I is soluble in MeOH, EtOH, CHCl₃, or hexane.	l_m_a_x(EtOH) 240 nm(e22000),313 nm(e19500)(Ref. 8028)	n_m_a_x(CHCl₃)3300,1720, 1690, and 1620cm^-¹(Ref. 8028)	¹H-NMR(400MHz,CDCl₃)dppm0.89(3H,t,J=7.2Hz),1.30(6H,m),1.80(2H,quint.,J=7.4Hz),1.97(2H,brq,J=7.7Hz),2.36(2H,t,J=7.4Hz),2.42(2H,m),2.65(1H,brdd,J=7.7,14.3Hz),2.78(1H,brdd,J=7.4,14.3Hz),3.69(3H,s),5.21(1H,brtd,J=7.7,11.0Hz),5.55(1H,brtd,J=7.4,11.0Hz),6.10(1H,tdd,J=7.9,0.9,10.9Hz),6.77(1H,brdd,J=10.9,12.6Hz),7.34(1H,d,J=12.6Hz),7.69(1H,d,J=0.5Hz).(Ref. 8028)	CIMS m/z 473 (M+1)(Ref. 8028)	CDl_e_x_t(EtOH)(De)nm 235(+11.4),260(-5.3),365(+2.7).(Ref. 8028)		Iodovulone I was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8028)					[8019] / [8023] / [8028]
290		punaglandin 1	methyl (5S,6R,7R)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenyl]-5,6,7-triacetoxyheptanoate	XPR8015	Yasuji Yamada	PUG 1	C₂₇H₃₇ClO₁₀	557.029							[a]_D+10.6(c 2.4, MeOH)(Ref. 8029/8036/8037)		l_m_a_x (MeOH)228 nm(e7900) (Ref. 8029/8036/8037)	n_m_a_x(CHCl₃)3500, 3430, 2930, 2860, 1740, 1610, 1375, 1235, 1025cm^-¹ (Ref. 8029/8036/8037)	¹H-NMR(500MHz, CDCl₃)dppm 1.00(3H, t, J=7.5Hz), 1.6(4H, m), 2.00(3H, s), 2.05(2H, m), 2.08(3H, s), 2.11(3H, s), 2.2(2H, m), 2.45(1H, dd, J=8.1, 14.7Hz), 2.53(1H, dd, J=7.0, 14.7Hz), 2.75(1H, d, J=4.2Hz), 2.78(2H, m), 3.57(1H, s), 3.65(3H, s), 5.18(1H, ddd, J=5.3, 5.3, 7.5Hz), 5.24(1H, dt, J=1.7.10.6Hz), 5.30(1H, ddd, J=7, 8.1, 10.8Hz), 5.34(1H, dd, J=4.2, 5.3Hz), 5.41(1H, dt, J=7, 10.6Hz), 5.61(1H, dt, J=7,10.8Hz), 5.61(1H, dd, J=5.3, 5.3Hz), 7.26(1H, s). (Ref. 8029/8036/8037)¹³C-NMR(125MHz, CDCl₃)dppm1 4.3(q), 20.2(t), 20.7(t), 20.9(q), 21.0(q), 21.1(q), 25.8(t), 30.1(t), 33.5(t), 39.4(t), 51.8(q), 53.4(d), 70.0(d), 71.6(d), 72.9(d), 77.2(s), 121.5(d), 126.0(d), 132.9(d), 134.6(d), 136.1(s), 158.1(d), 170.4(s), 170.5(s), 171.3(s), 173.8(s), 196.0(s). (Ref. 8029/8036/8037)	EIMS(30 eV)m/z 496(3), 478(5), 447(17), 418(25), 387(100), 358(22), 327(37), 267(58).DCIMS m/z 574(100). (Ref. 8029/8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
291		punaglandin 1 acetate	methyl (5S,6R,7R)-7-[(1R,2S)-2-acetoxy-4-chloro-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenyl]-5,6,7-triacetoxyheptanoate	XPR8016	Yasuji Yamada		C₂₉H₃₉ClO₁₁	599.066											¹H-NMR(300MHz, CDCl₃)dppm 0.9(3H, t), 1.6(4H, m), 1.6(2H, m), 1.9(3H, s), 2.0(3H, s), 2.1(3H, s), 2.1(2H, m), 2.2(3H, s), 2.3(2H, s), 2.8(1H, t), 2.9(1H, dd), 3.1(1H, d), 3.5(1H, dd), 3.6(3H, s), 5.3(1H, m), 5.3(1H, m), 5.3(1H, m), 5.3(1H, m), 5.3(1H, m), 5.6(1H, dt), 5.7(1H, dt), 7.8(1H, s). (Ref. 8036/8037)				Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
292		punaglandin 2	methyl (5S,6R,7R)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenyl]-5,6,7-triacetoxyheptanoate	XPR8017	Yasuji Yamada	PUG 2	C₂₇H₃₉ClO₁₀	559.045							[a]_D+8.8(c 1.9, MeOH)(Ref. 8029/8036/8037)		l_m_a_x (MeOH)227 nm(e7500) (Ref. 8029/8036/8037)	n_m_a_x(CH₂CI₂) 3420(br), 2920, 1730(br), 1375, 1230, 1045cm^-¹ (Ref. 8029/8036/8037)	¹H-NMR(500MHz, CDCl₃)dppm 0.85(3H, t, J=6.7Hz), 1.26(6H, m), 1.6(4H, m), 1.95(2H, m), 1.98(3H, s), 2.06(3H, s), 2.09(3H, s), 2.3(2H, m), 2.40(1H, dd, J=7.9, 14.4Hz), 2.48(1H, dd, J=7.3, 14.4Hz), 2.74(1H, d, J=4.2Hz), 3.48(1H, s), 3.65(3H, s), 5.18(1H, ddd, J=5.3, 5.3, 7.5Hz), 5.25(1H, dt, J=7.3, 7.9, 10.9Hz), 5.31(1H, dd, J=4.2, 5.3Hz), 5.61(1H, dd, J=5.3, 5.3Hz), 5.63(1H, dt, J=7, 10.9Hz), 7.26(1H, s).(Ref. 8029/8036/8037)¹³C-NMR(125MHz, CDCl₃)dppm 14.2(q), 20.2(t), 20.9(q), 21.0(q), 21.1(q), 22.7(t), 27.6(t), 29.3(t), 30.2(t), 31.7(t), 33.5(t), 39.5(t), 51.9(q), 53.5(d), 70.0(d), 71.7(d), 72.9(d), 77.2(s), 121.1(d), 136.0(d), 136.8(s), 158.2(d), 170.4(s), 170.6(s), 171.9(s), 173.8(s), 196.0(s). (Ref. 8029/8036/8037)	EIMS(70 eV)m/z 498(1), 480(1), 467(4), 447(5), 387(100), 327(100), 285(28).CIMS m/z 541(7), 499(58), 481(30), 439(13), 421(100), 361(59).HRCIMS m/z 499.21350 for C₂₅H₃₆³⁵Cl, calcd 499.20988.DCIMS m/z 576 (M⁺+NH₄).(Ref. 8029/8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
293		punaglandin 2 acetate	methyl (5S,6R,7R)-7-[(1R,2S)-2-acetoxy-4-chloro-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenyl]-5,6,7-triacetoxyheptanoate	XPR8018	Yasuji Yamada		C₂₉H₄₁ClO₁₁	601.082							[a]_D+10(c 0.6, MeOH) (Ref. 8036/8037)		l_m_a_x(CHCl₃) 242 nm(e5600) (Ref. 8036/8037)	n_m_a_x(CHCl₃) 2960, 2920, 2870, 1740(br), 1440, 1370, 1225, 1030cm^-¹ (Ref. 8036/8037)	¹H-NMR(300MHz, CDCl₃)dppm 0.86(3H, t, J=6.0Hz), 1.26(6H, m), 1.6(4H, m), 1.90(3H, s), 1.99(3H, s), 2.05(3H, s), 2.09(2H, m), 2.14(3H, s), 2.3(2H, t), 2.77(1H, dd, J=8.3, 10.2Hz), 2.87(1H, dd, J=8.3, 10.2Hz), 3.01(1H, d, J=1.7Hz), 3.65(3H, s), 5.10(1H, dt, J=2.4, 7.8Hz), 5.27(1H, br dt, J=1.1Hz), 5.33(1H, dd, J=1.1, 7.8Hz), 5.50(1H, dt, J=1.7, 7.8Hz), 5.58(1H, dt, J=2.4, 7.8Hz), 7.82(1H, s). (Ref. 8036/8037)¹³C-NMR(75MHz, CDCl₃)dppm 14.0, 20.4, 20.6, 20.8, 21.0, 21.6, 22.5, 27.5, 29.0, 30.3, 31.4, 33.4, 51.6, 52.9, 69.5, 71.1, 72.7, 83.8, 120.0, 136.4, 137.7, 155.1, 169.3, 169.9, 169.9, 170.7, 173.3, 195.0. (Ref. 8036/8037)	EIMS(70 eV)m/z 387(2.6), 378(1.0),327(3.8), 308(1.2), 279(42.5), 167(66.6), 149(99.5), 46(100). (Ref. 8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
294		punaglandin 3	methyl (5S,6R,7E)-7-[(2S)-4-chloro-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate	XPR8019	Yasuji Yamada	PUG 3	C₂₅H₃₃ClO₈	496.977		Punaglandin 3 inhibits L 1210 leukemia cell proliferation with ac IC₅₀ value of 0.02 mg/ml.(Ref. 8029)					[a]_D+66.8(c 0.54, MeOH) (Ref. 8029/8036/8037)		l_m_a_x (MeOH)238 nm(e8600) (Ref. 8029/8036/8037)	n_m_a_x(CHCl₃) 3100-3600(br), 2960, 2940, 1725, 1680(sh), 1378, 1235, 1110-990(br) cm^-¹ (Ref. 8029/8036/8037)	¹H-NMR(300MHz, CDCl₃)dppm 0.94(3H, t, J=7.5Hz), 1.6(4H, m), 2.05(2H, m), 2.05(3H, s), 2.09(3H, s), 2.3(2H, m), 2.68(1H, dd, J=7.0, 14.3Hz), 2.74(2H, br dd, J=7.1, 7.1Hz), 3.01(1H, dd, J=8.1, 14.3Hz), 3.50(1H, s), 3.65(3H, s), 5.2(1H, m), 5.2(1H, m), 5.25(1H, m), 5.41(1H, m), 5.53(1H, m), 6.02(1H, dd, J=4.3, 9.1Hz), 6.35(1H, d, J=9.1Hz), 7.27(1H, s). (Ref. 8029/8036/8037)¹³C-NMR(75MHz, CDCl₃)dppm 14.2(q), 20.2(t), 20.5(t), 20.8(q), 20.8(q), 25.6(t), 29.6(t), 33.2(t), 35.6(t), 51.7(q), 69.8(d), 73.7(d), 77.2(s), 122.0(d), 126.1(d), 130.5(d), 132.5(d), 133.1(d), 137.2(s), 140.5(s), 155.7(d), 169.9(s), 171.1(s), 173.8(s), 186.6(s). (Ref. 8029/8036/8037)	EIMS(25 eV)m/z 478(1), 418(14), 387(50), 376(14), 358(26), 327(100), 275(30), 267(38), 253(30), 235(35). (Ref. 8029/8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)	Punaglandin 3 was synthesized from D-(-)-diethyl tartrate and 2-deoxy-D-ribose.(Ref. 8030)				[8029] / [8030] / [8036] / [8037]
295		punaglandin 3 acetate	methyl (5S,6R,7E)-7-[(2S)-2-acetoxy-4-chloro-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate	XPR8020	Yasuji Yamada		C₂₇H₃₅ClO₉	539.014							[a]_D+31(c 2.7, CHCl₃) (Ref. 8036/8037)		l_m_a_x(CHCl₃) 251 nm(e8000) (Ref. 8036/8037)	n_m_a_x(CHCl₃) 3020, 2960, 2940, 2929, 2870, 1744(br), 1370, 1220(br), 1020(br) cm^-¹ (Ref. 8036/8037)	¹H-NMR(300MHz, CDCl₃)dppm 0.94(3H, t, J=7.5Hz), 1.6(4H, m), 1.9(2H, m), 2.05(3H, s), 2.08(3H, s), 2.10(3H, s), 2.3(2H, t), 2.70(2H, t, J=7.0Hz), 2.8(1H, dd, J=6.6, 14.0Hz), 3.33(1H, dd, J=8.7, 14.0Hz), 3.63(3H, s), 5.2(1H, m), 5.2(1H, m), 5.2(1H, m), 5.38(1H, ddd, J=2, 7, 10.2Hz), 5.46(1H, dt, J=7.0, 10.6Hz), 5.86(1H, dd, J=4.1, 9.4Hz), 6.47(1H, d, J=9.4Hz), 7.59(1H, s). (Ref. 8036/8037)¹³C-NMR(75MHz, CDCl₃)dppm 14.2, 20.2, 20.6, 20.7, 20.8, 21.6, 25.7, 30.0, 33.3, 33.9, 51.6, 69.6, 73.3, 83.3, 120.9, 121.5, 125.9, 130.4, 132.7, 133.8, 135.4, 151.5, 169.3, 169.9, 170.1, 173.6, 185.4. (Ref. 8036/8037)	EIMS(70 eV)m/z 538(0.1), 496(0.1), 478(0.3), 436(0.3), 387(7.0), 376(8.4), 358(10.9), 345(5.3), 327(25.9), 285(12.5), 253(26.2), 235(25.4), 207(21.5), 43(100). (Ref. 8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
296		punaglandin 4	methyl (5S,6R,7E)-7-[(2S)-4-chloro-2-hydroxy-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate	XPR8021	Yasuji Yamada	PUG 4	C₂₅H₃₅ClO₈	498.993		Punaglandin 4 inhibits L 1210 leukemia cell proliferation with ac IC₅₀ value of 0.07 mg/ml.(Ref. 8034)					[a]_D+46.3(c 1.6, MeOH) (Ref. 8029/8036/8037)		l_m_a_x (MeOH)240 nm(e6900) (Ref. 8029/8036/8037)	n_m_a_x(CHCl₃) 3150-3600(br), 2930, 2860(sh), 1725, 1675(sh), 1375, 1150-1300(br), 1000-1100(br) cm^-¹ (Ref. 8029/8036/8037)	¹H-NMR(300MHz, CDCl₃)dppm 0.86(3H, t, J=7.1Hz), 1.3(6H, m), 1.6(4H, m), 2.0(2H, m), 2.05(3H, s), 2.10(3H, s), 2.3(2H, m), 2.62(1H, dd, J=7.2, 13.5Hz), 2.95(1H, dd, J=8.5, 13.5Hz), 3.63(3H, s), 3.63(1H, s), 5.25(1H, m), 5.25(1H, m), 5.41(1H, m), 5.52(1H, dt, J=6.7, 10.9Hz), 6.01(1H, dd, J=4.3, 9.1Hz), 6.33(1H, d, J=9.1Hz), 7.25(1H, s). (Ref. 8029/8036/8037)¹³C-NMR(75MHz, CDCl₃)dppm 14.2(q), 20.2(t), 20.5(t), 20.8(q), 20.8(q), 25.6(t), 29.6(t), 33.2(t), 35.6(t), 51.7(q), 69.8(d), 73.7(d), 77.2(s), 122.0(d), 126.1(d), 130.5(d), 132.5(d), 133.1(d), 137.2(s), 140.5(s), 155.7(d), 169.9(s), 171.1(s), 173.8(s), 186.6(s). (Ref. 8029/8036/8037)	EIMS(70 eV)m/z 420(2), 387(23), 378(8), 360(6), 347(19), 327(100), 285(44), 267(84), 253(74), 235(82). (Ref. 8029/8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)	Punaglandin 4 was synthesized from D-(-)-diethyl tartrate and 2-deoxy-D-ribose.(Ref. 8030)Punaglandin 4 was synthesized from (4S)-3-chloro-4-(dimethyl-t-butylsilyloxy)cyclopent-2-enone which is available in five steps from phenol.(Ref. 8031/8034)Other synthesis of punaglandin 4.(Ref. 8032/8033/8035)				[8029] / [8030] / [8031] / [8032] / [8033] / [8034] / [8035] / [8036] / [8037]
297		punaglandin 4 acetate	methyl (5S,6R,7E)-7-[(2S)-2-acetoxy-4-chloro-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate	XPR8022	Yasuji Yamada		C₂₇H₃₅ClO₉	539.014							[a]_D+9.4(c 3.6, CHCl₃) (Ref. 8036/8037)		l_m_a_x(CHCl₃) 249 nm(e6700) (Ref. 8036/8037)	n_m_a_x(film) 3020, 2960, 2920, 2860, 1740(br), 1680(sh), 1440, 1370, 1220(br), 1020 cm^-¹ (Ref. 8036/8037)	¹H-NMR(300MHz, CDCl₃)dppm 0.86(3H, t, J=6.3Hz), 1.3(6H, m), 1.6(4H, m), 1.94(2H, t, J=6.7Hz), 2.06(3H, s), 2.09(3H, s), 2.11(3H, s), 2.3(2H, m), 2.77(1H, dd, J=6.6, 14.3Hz), 3.31(1H, dd, J=6.6, 14.3Hz), 3.64(3H, s), 5.07(1H, m), 5.1(1H, dt, J=6.6, 10.7Hz), 5.49(1H, dt, J=6.7, 10.7Hz), 5.86(1H, dd, J=4.1, 9.2Hz), 6.47(1H, d, J=9.2Hz), 7.6(1H, s). (Ref. 8036/8037)¹³C-NMR(75MHz, CDCl₃)dppm 14.5, 21.1, 21.2, 21.2, 22.1, 23.0, 27.9, 29.4, 30.5, 32.0, 33.8, 34.4, 52.1, 70.0, 73.7, 83.8, 120.9, 130.8, 136.3, 137.6, 139.0, 152.1, 169.8, 170.3, 170.6, 173.6, 185.9. (Ref. 8036/8037)	EIMS(70 eV)m/z 540(3.2), 498(0.8), 480(0.5), 462(1.6), 438(2.2), 420(3.8), 387(25.1), 378(23.5), 327(50.6), 308(29.3), 266(41.4), 253(44.2), 237(37.5), 222(43.4), 207(37.3), 43(100). (Ref. 8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
298		Z-punaglandin 3	methyl (5S,6R,7Z)-7-[(2S)-4-chloro-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate	XPR8023	Yasuji Yamada	(7Z)-PUG 3	C₂₅H₃₃ClO₈	496.977											¹H-NMR(300MHz, CDCl₃)dppm 0.95(3H,t,J=7.5Hz), 1.6(4H,m), 2.0(2H,m), 2.03(3H,s), 2.10(3H,s), 2.3(2H,m), 2.47(1H,dd,J=7.3,14.5Hz), 2.59(1H,dd,J=7.7,14.5Hz), 2.74(2H,dd,J=6.4,7.2Hz), 3.5(1H,s), 3.64(3H,s), 5.1(1H,m), 5.1(1H,m), 5.1(1H,m), 5.2(1H,m), 5.36(1H,dt,J=7.2,10.9Hz), 6.08(1H,d), 6.32(1H,dd,J=3.5,7.7Hz), 7.20(1H,s). (Ref. 8029/8036/8037)	EIMS(70 eV)m/z 436(1.2), 418(0.9), 387(5.2), 376(4.1), 345(7.5), 327(41.7), 285(28.2), 43(100). (Ref. 8029/8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
299		Z-punaglandin 3 acetate	methyl (5S,6R,7Z)-7-[(2S)-2-acetoxy-4-chloro-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate	XPR8024	Yasuji Yamada		C₂₇H₃₅ClO₉	539.014							[a]_D+19(c 1.8, CHCl₃) (Ref. 8036/8037)		l_m_a_x(CHCl₃) 255 nm(e9000), 242 nm(e7900) (Ref. 8036/8037)		¹H-NMR(300MHz, CDCl₃)dppm 0.95(3H, t, J=7.5Hz), 1.6(4H, m), 2.00(3H, s), 2.02(3H, s), 2.07(2H, m), 2.10(3H, s), 2.3(2H, m), 2.63(1H, dd, J=6.7, 14.5Hz), 2.73(2H, t, J=4.8Hz), 2.88(1H, dd, J=6.7, 14.5Hz), 3.64(3H, s), 5.15(1H, ddd, J=6.7, 7.5, 10.6Hz), 5.18(1H, dt, J=3.4Hz), 5.20(1H, dt, J=4.8, 10.5Hz), 5.40(1H, dt, J=7.0, 10.5Hz), 5.53(1H, dt, J=7.3, 10.6Hz), 6.1(1H, d), 6.46(1H, dd, J=3.4, 7.7Hz), 7.53(1H, s). (Ref. 8036/8037)¹³C-NMR(75MHz, CDCl₃)dppm 14.2, 20.6, 20.6, 20.8, 20.8, 21.6, 25.7, 30.0, 33.4, 35.3, 51.6, 69.9, 74.0, 82.1, 120.9, 125.8, 132.7, 133.7, 136.0, 136.5, 139.6, 150.1, 169.5, 169.6, 170.0, 173.7, 193.8. (Ref. 8036/8037)	EIMS(70 eV)m/z 538(3.5), 478(2.4), 436(2.8), 418(12.5), 387(16.3), 376(20.8), 366(11.2), 358(23.0), 345(13.4), 327(28.6), 43(100). (Ref. 8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
300		Z-punaglandin 4	methyl (5S,6R,7Z)-7-[(2S)-4-chloro-2-hydroxy-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate	XPR8025	Yasuji Yamada	(7Z)-PUG 4	C₂₅H₃₅ClO₈	498.993		Z-Punaglandin 4 inhibits L 1210 leukemia cell proliferation with ac IC₅₀ value of 0.06 mg/ml.(Ref. 8034)									¹H-NMR(300MHz, CDCl₃)dppm 0.87(3H, t, J=6Hz), 1.3(6H, m), 1.6(4H, m), 1.97(2H, m), 2.03(3H, s), 2.10(3H, s), 2.3(2H, m), 2.44(1H, dd, J=8, 14Hz), 2.56(1H, dd, J=8, 14Hz), 2.79(1H, s), 3.64(3H, s), 5.2(1H, m), 5.2(1H, m, J=3.4Hz), 5.57(1H, dt, J=7.6, 10.9Hz), 6.07(1H, d), 6.32(1H, dd, J=3.6, 7.8Hz), 7.20(1H, s). (Ref. 8029/8036/8037)				Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)	Z-Punaglandin 4 was synthesized from (4S)-3-chloro-4-(dimethyl-t-butylsilyloxy)cyclopent-2-enone which is available in five steps from phenol.(Ref. 8031/8034)Other synthesis of Z-punaglandin 4.(Ref. 8032/8033/8035)				[8029] / [8031] / [8032] / [8033] / [8034] / [8035] / [8036] / [8037]
301		Z-punaglandin 4 acetate	methyl (5S,6R,7Z)-7-[(2S)-2-acetoxy-4-chloro-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate	XPR8026	Yasuji Yamada		C₂₇H₃₅ClO₉	539.014							[a]_D+11(c 1.8, CHCl₃) (Ref. 8036/8037)		l_m_a_x (MeOH)254 nm(e6700), 241 nm(e5100) (Ref. 8036/8037)		¹H-NMR(300MHz, CDCl₃)dppm 0.87(3H, t, J=6.1Hz), 1.3(6H, m), 1.6(4H, m), 1.9(2H, m), 2.00(3H, s), 2.02(3H, s), 2.10(3H, s), 2.3(2H, m), 2.58(1H, dd), 2.86(1H, dd), 3.64(3H, s), 5.2(1H, m), 5.2(1H, m), 5.54(1H, dt, J=8.8, 10.7Hz), 6.09(1H, d), 6.46(1H, dd, J=3.9, 7.8Hz), 7.53(1H, s). (Ref. 8036/8037)¹³C-NMR(75MHz, CDCl₃)dppm 14.0, 20.6, 20.8, 21.6, 22.6, 23.1, 27.5, 29.0, 30.0, 31.5, 33.5, 35.4, 51.6, 69.8, 74.0, 82.3, 120.6, 135.7, 135.8, 136.5, 142.5, 149.0, 173.1, 173.4, 173.7, 176.3, 190.8. (Ref. 8036/8037)	EIMS(70 eV)m/z 540(3.2), 480(0.9), 438(2.7), 429(2.6), 420(3.5), 387(18.6), 378(17.2), 360(14.1), 327(27.9), 308(20.4), 285(14.9), 43(100). (Ref. 8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
302		punaglandin 3 epoxide	methyl (5S,6R,7E)-7-[(2S,3R,4S)-4-chloro-3,4-epoxy-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentanylidene]-5,6-diacetoxyheptanoate	XPR8027	Yasuji Yamada		C₂₅H₃₃ClO₉	512.977							[a]_D+16(c 3.0, MeOH) (Ref. 8036/8037)		l_m_a_x(CHCl₃) 245 nm(e7400) (Ref. 8036/8037)	n_m_a_x(film) 3483(br), 3010, 2960, 2875, 1736(br), 1375, 1223(br), 1024 cm^-¹ (Ref. 8036/8037)	¹H-NMR(300MHz, CDCl₃)dppm 0.94(3H, t, J=7.5Hz), 1.6(4H, m), 2.0(2H, m), 2.03(3H, s), 2.08(3H, s), 2.3(2H, m), 2.7(2H, m), 2.8(1H, m), 2.8(1H, m), 3.65(3H, s), 3.67(1H, s), 3.96(1H, s), 5.2(1H, m), 5.2(1H, m), 5.2(1H, m), 5.4(1H, m), 5.58(1H, m), 5.98(1H, dd, J=4.2, 9.0Hz), 6.54(1H, d, J=9.0Hz). (Ref. 8036/8037)¹³C-NMR(75MHz, CDCl₃)dppm 14(q), 20.2(t), 20.6(t), 20.7(q), 20.8(q), 25.7(t), 29.6(t), 29.7(t), 33.2(t), 34.2(t), 51.8(q), 66.7(d), 69.5(d), 73.6(d), 93.1(s), 120.9(d), 125.9(d), 132.8(d), 133.9(d), 138.6(s), 139.9(d), 169.9(s), 170.7(s), 173.6(s), 187.3(s). (Ref. 8036/8037)	EIMS(70 eV)m/z 512(0.1), 494(0.8), 403(3.4), 343(24.3), 283(18.9), 43(100). (Ref. 8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
303		punaglandin 4 epoxide	methyl (5S,6R,7E)-7-[(2S,3R,4S)-4-chloro-3,4-epoxy-2-hydroxy-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentanylidene]-5,6-diacetoxyheptanoate	XPR8028	Yasuji Yamada		C₂₅H₃₅ClO₉	514.993							[a]_D+22.5(c 0.8, MeOH) (Ref. 8036/8037)				¹H-NMR(300MHz, CDCl₃)dppm 0.86(3H, t, J=6.0Hz), 1.2(6H, m), 1.5(6H, m), 2.0(2H, m), 2.03(3H, s), 2.09(3H, s), 2.3(2H, m), 2.76(1H, dd, J=8, 4Hz), 2.85(1H, dd, J=8, 4Hz), 3.55(1H, s), 3.66(3H, s), 3.95(1H, s), 5.2(1H, m), 5.2(1H, m), 5.59(1H, m), 5.97(1H, dd, J=4.4, 8.9Hz), 6.55(1H, d, J=8.9Hz). (Ref. 8036/8037)	EIMS(70 eV)m/z 514(0.2), 496(4), 436(1), 423(5), 403(7), 343(39), 283(22), 269(22), 43(100). (Ref. 8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
304		punaglandin 5	methyl (5S,6R)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenyl]-5,6-diacetoxyheptanoate	XPR8029	Yasuji Yamada	PUG 5	C₂₅H₃₅ClO₈	498.993							[a]_D+10.2(c 4.7, CHCl₃) (Ref. 8036/8037)		l_m_a_x(CHCl₃) 244 nm(e5000) (Ref. 8036/8037)	n_m_a_x(CHCl₃) 3450(br), 3010, 2960, 2930, 2870, 1748, 1600, 1440, 1380, 1230, 1170, 1040 cm^-¹ (Ref. 8036/8037)	¹H-NMR(300MHz, CDCl₃)dppm 0.94(3H, t, J=7.3Hz), 1.6(4H, m), 1.73(1H, dd, J=7.8, 15.2Hz), 2.0(2H, t), 2.08(3H, s), 2.09(3H, s), 2.16(1H, dd, J=8.1, 14.3Hz), 2.3(2H, t), 2.58(1H, s), 2.65(1H, dd, J=4.6, 8.5Hz), 2.67(1H, dd, J=7.7, 7.8Hz), 2.77(2H, t), 2.80(1H, dd, J=8.0, 8.5Hz), 3.64(3H, s), 5.1(1H, m), 5.1(1H, m), 5.1(1H, m), 5.11(1H, br d, J=3.4Hz), 7.30(1H, s). (Ref. 8036/8037)¹³C-NMR(75MHz, CDCl₃)dppm 14.2, 20.2, 20.6, 20.9, 25.7, 29.9, 30.0, 33.4, 35.9, 38.7, 51.6, 55.1, 72.2, 73.7, 77, 121.6, 125.9, 132.9, 134.3, 134.6, 157.5, 170.6, 170.7, 171.1, 196.6. (Ref. 8036/8037)	EIMS(70 eV)m/z 480(0.4), 419(5.9), 389(9.4), 387(8.1), 329(31.4), 285(10.8), 43(100). (Ref. 8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
305		punaglandin 5 acetate	methyl (5S,6R)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenyl]-5,6-diacetoxyheptanoate	XPR8030	Yasuji Yamada		C₂₇H₃₇ClO₉	541.030							[a]_D+8(c 1.2, MeOH) (Ref. 8036/8037)		l_m_a_x(CHCl₃) 240 nm(e4500) (Ref. 8036/8037)		¹H-NMR(300MHz, CDCl₃)dppm 0.95(3H, t, J=7Hz), 1.6(4H, m), 1.9(2H, m), 2.0(2H, m), 2.1(3H, s), 2.2(3H, s), 2.2(3H, s), 2.3(2H, m), 2.3(2H, m), 2.6(2H, t), 3.0(1H,dd), 3.2(1H, t), 3.6(3H, s), 5.0(1H, m), 5.2(1H, dt, J=10.5Hz), 5.2(1H, dd, J=8, 10Hz), 5.3(1H, m), 5.4(1H, m), 5.5(1H, ddd, J=1, 7, 10.8Hz), 7.5(1H, s). (Ref. 8036/8037)¹³C-NMR(75MHz, CDCl₃)dppm 14.2, 20.6, 20.9, 21.0, 21.5, 25.7, 26.4, 30.0, 33.4, 35, 36, 52, 52.2, 72.3, 72.8, 85.5, 121.0, 123.0, 125.7, 132.8, 133.4, 155.6, 169.9, 170.3, 170.5, 173.0, 197. (Ref. 8036/8037)	EIMS(70 eV)m/z 480(4.9), 420(27.4), 407(13.6), 378(12.4), 360(25.6), 329(33.4), 269(29.2), 43(100). (Ref. 8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
306		punaglandin 6	methyl (5S,6R)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenyl]-5,6-diacetoxyheptanoate	XPR8031	Yasuji Yamada	PUG 6	C₂₅H₃₇ClO₈	501.009							[a]_D+14(c 0.9, CHCl₃) (Ref. 8036/8037)		l_m_a_x(CHCl₃) 231 nm(e5300) (Ref. 8036/8037)	n_m_a_x(CCl₄) 3450(br), 3010, 2950, 2920, 2750, 1720(br), 1600, 1440, 1370, 1230(br), 1030 cm^-¹ (Ref. 8036/8037)	¹H-NMR(300MHz, CDCl₃)dppm 0.85(3H, t, J=6.2Hz), 1.3(6H, m), 1.6(4H, m), 1.73(1H, ddd, J=1.2, 8.4, 15.4Hz), 2.03(2H, dt, J=6.2, 6.4Hz), 2.10(3H, s), 2.10(1H, dd, J=1.4, 13.5Hz), 2.11(3H, s), 2.12(1H, ddd, J=4.5, 15.4Hz), 2.3(2H, t), 2.54(1H, s), 2.66(1H, dd, J=4.5, 8.4Hz), 2.77(1H, dd, J=1.4, 13.5Hz), 3.65(3H, s), 5.11(1H, br d, J=3.4Hz), 5.28(1H, ddd, J=1.2, 3.4, 8Hz), 5.65(1H, dt, J=6.4, 11.1Hz), 7.29(1H, s). (Ref. 8036/8037)¹³C-NMR(75MHz, CDCl₃)dppm 14.0, 20.6, 20.8, 21.1, 22.5, 25.5, 27.5, 29.0, 30.0, 31.5, 33.4, 35.8, 51.6, 55.1, 72.1, 72.2, 78.9, 121.3, 134.4, 136.2, 157.6, 170.6, 170.6, 173.5, 196.7. (Ref. 8036/8037)	EIMS(70 eV)m/z 409(4.1), 329(31.8), 315(5.4), 269(28.1), 255(28.6), 43(100).EIMS(25 eV)m/z 482(0.9), 329(100), 269(37.9), 255(16.3), 173(20.1), 107(32.1), 60(18.6), 43(42.5), 36(19.6). (Ref. 8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
307		punaglandin 7	methyl (5Z,7S)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenyl]-5-heptenoate	XPR8032	Yasuji Yamada	PUG 7	C₂₃H₃₁ClO₆	438.941											¹H-NMR(300MHz, CDCl₃)dppm 0.9(3H, t), 1.6(4H, m), 2.0(3H, s), 2.2(2H, m), 2.3(2H, m), 2.4(1H, dd), 2.5(1H, dd), 2.6(1H, d), 2.7(2H, t), 3.2(1H, s), 3.6(3H, s), 5.3(1H, m), 5.3(1H, m), 5.3(1H, m), 5.3(1H, m), 5.6(1H, dt), 5.9(1H, dd), 7.30(1H, s). (Ref. 8036/8037)				Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
308		punaglandin 8	methyl (5Z,7S)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenyl]-5-heptenoate	XPR8033	Yasuji Yamada	PUG 8	C₂₃H₃₃ClO₆	440.957									l_m_a_x (MeOH)227 nm(e6900) (Ref. 8036/8037)	n_m_a_x(CHCl₃) 3300-3600(br), 2929, 2860, 1730, 1375, 1200-1250 cm^-¹ (Ref. 8036/8037)	¹H-NMR(300MHz, CDCl₃)dppm 0.86(3H, t, J=6.7Hz), 1.3(6H, m), 1.7(2H, m), 1.98(3H, s), 2.00(2H, dt, J=6.7, 7.0Hz), 2.19(2H, dt, J=6.7, 7.0Hz), 2.3(2H, t), 2.38(1H, dd, J=7.1, 14.7Hz), 2.53(1H, dd, J=8.1, 14.7Hz), 3.18(1H, s), 3.65(3H, s), 5.32(1H, ddd, J=7.1, 8.1, 11.2Hz), 5.57(1H, dd, J=6.7, 7Hz), 5.64(1H, dt, J=6.7, 7.0Hz), 5.83(1H, dd, J=9.6, 10.7Hz), 5.94(1H, dd, J=3.3, 9.6Hz), 7.26(1H, s). (Ref. 8036/8037)	EIMS(70 eV)m/z 380, 362, 349, 269(100), 237 (Ref. 8036/8037)			Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)					[8029] / [8036] / [8037]
309		clavulolactone I (Ref. 8038)	(R)-4-{(1Z,3E)-3-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-1-propenyl}-4-butanolide	XPR8034	Yasuji Yamada		C₂₂H₂₈O₅	372.455							[a]_D -7.8(C 0.26, CHCl₃)(Ref. 8038)		l^E^t^O^H_m_a_x 231 nm(log e4.14),292 nm(log e4.20)(Ref. 8038)	n^fⁱ^l^m_m_a_x1770,1732, 1704, 1643, and 1230cm^-¹(Ref. 8038)	¹H-NMR(500MHz,CDCl₃)dppm0.88(3H,t,J=6.9Hz),1.20-1.35(6H,m),1.94(2H,m),1.97-2.04(1H,m),2.04(3H,s),2.48-2.58(1H,m),2.60(1H,d,J=9.5Hz),2.62(1H,dd,J=2.5,9.5Hz),2.70(1H,dd,J=8.3,14.6Hz),2.93(1H,dd,J=6.9,14.6Hz),5.18(1H,ddd,J=6.9,8.3,10.8Hz),5.53(1H,q,J=7.3Hz),5.53-5.59(1H,m),6.01(1H,ddd,J=0.6,8.7,10.9Hz),6.45(1H,d,J=6.1Hz),6.67(1H,ddd,J=1.2,10.9,12.8Hz),7.01(1H,d,J=12.8Hz),7.48(1H,d,J=6.1Hz).(Ref. 8038) ¹³C-NMR(125MHz,CDCl₃)dppm14.0,21.3,22.5,27.4,29.7,29.0,29.3,31.5,36.0,75.5,85.1,120.7,123.3,125.0,135.1,135.4,138.2,138.4,158.2,169.2,176.3,193.3.(Ref. 8038)	EIMS m/z 372 (M⁺). HREIMS m/z 372.1916 for C₂₂H₂₈O₅, calcd 372.1937.(Ref. 8038)			Clavulolactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8038/8039)	Clavulolactone I was converted from clavulone I.(Ref. 8038)				[8038] / [8039]
310		clavulolactone II (Ref. 8039)	(R)-4-{(1E,3E)-3-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-1-propenyl}-4-butanolide	XPR8035	Yasuji Yamada		C₂₂H₂₈O₅	372.455							[a]_D -25.6(C 0.26, CHCl₃)(Ref. 8039)		l^E^t^O^H_m_a_x 292 nm(e16500),231 nm(e12500)(Ref. 8039)	n^fⁱ^l^m_m_a_x1778,1745, 1704, 1644, and 1231cm^-¹(Ref. 8039)	¹H-NMR(400MHz,CDCl₃)dppm0.87(3H,t,J=7.2Hz),1.20-1.34(6H,m),1.94(2H,brq,J=6.3Hz),2.02(3H,s),2.04(1H,m),2.52(1H,m),2.55(2H,m),2.71(1H,brdd,J=8.1,14.2Hz),2.91(1H,brdd,J=7.1,14.2Hz),5.15(1H,m),5.15(1H,m),5.52(1H,m),6.17(1H,dd,J=4.9,14.7Hz),6.42(1H,d,J=6.1Hz),6.82(1H,ddd,J=1.5,12.0,14.7Hz),6.91(1H,brd,J=12.0Hz),7.50(1H,brd,J=6.1Hz).(Ref. 8039) ¹³C-NMR(100MHz,CDCl₃)dppm14.0,21.2,22.5,27.4,27.7,28.2,29.0,31.5,35.8,78.6,85.2,121.0,124.9,128.9,135.06,135.14,137.2,140.8,158.0,169.3,176.2,193.3.(Ref. 8039)	EIMS m/z 372 (M⁺). HREIMS m/z 372.1920 for C₂₂H₂₈O₅, calcd 372.1937.(Ref. 8039)			Clavulolactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8038/8039)	Clavulolactone II was converted from clavulone II.(Ref. 8039)				[8038] / [8039]
311		clavulolactone III (Ref. 8038)	(R)-4-{(1E,3Z)-3-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-1-propenyl}-4-butanolide	XPR8036	Yasuji Yamada		C₂₂H₂₈O₅	372.455							[a]_D -7.3(C 0.21, CHCl₃)(Ref. 8039)		l^E^t^O^H_m_a_x 293 nm(e15500),229 nm(e17900)(Ref. 8039)	n^fⁱ^l^m_m_a_x1778,1742, 1698, 1643, and 1232cm^-¹(Ref. 8039)	¹H-NMR(400MHz,CDCl₃)dppm0.88(3H,t,J=7.1Hz),1.22-1.33(6H,m),1.97(2H,brq,J=7.2Hz),2.03(3H,s),2.05(1H,m),2.47(1H,m),2.58(2H,dd,J=6.9,9.3Hz),2.65(1H,brdd,J=7.6,14.3Hz),2.84(1H,brdd,J=7.3,14.3Hz),5.10(1H,brdd,J=7.3,7.9Hz),5.22(1H,m),5.54(1H,m),6.08(1H,dd,J=7.3,15.6Hz),6.38(1H,d,J=6.1Hz),6.53(1H,d,J=11.3Hz),7.49(1H,d,J=6.1Hz),7.82(1H,brdd,J=11.3,15.6Hz).(Ref. 8039) ¹³C-NMR(100MHz,CDCl₃)dppm14.0,21.6,22.5,27.4,28.6,28.6,29.0,31.4,35.7,80.0,85.0,121.1,127.6,132.4,135.0,136.6,139.8,139.8,156.3,169.6,176.5,194.0.(Ref. 8039)	EIMS m/z 372 (M⁺). HREIMS m/z 372.1961 for C₂₂H₂₈O₅, calcd 372.1937.(Ref. 8039)			Clavulolactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8038/8039)	Clavulolactone III was converted from clavulone III.(Ref. 8039)				[8038] / [8039]
312		17,18-dehydroclavulone I (Ref. 8038)	methyl (4R,5Z,7E)-4-acetoxy-7-[(S)-2-acetoxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8037	Yasuji Yamada		C₂₅H₃₂O₇	444.517							[a]_D -27.1(C 0.31, CHCl₃)(Ref. 8038)		l^E^t^O^H_m_a_x 228 nm(loge3.98),293nm(loge4.01)(Ref. 8038)	n^fⁱ^l^m_m_a_x1770,1732,1704,1643, and 1230cm^-¹(Ref. 8038)	¹H-NMR(500MHz,CDCl₃)dppm0.96(3H,t,J=7.5Hz),1.90-2.02(2H,m),2.00-2.10(2H,m),2.03(3H,s),2.04(3H,s),2.38(2H,q,J=7.3Hz),2.67-2.76(2H,m),2.69(1H,dd,J=8.0,14.2Hz),2.98(1H,dd,J=7.4,14.2Hz),3.69(3H,s),5.21(1H,dt,J=7.6,10.8Hz),5.23(1H,ddd,J=7.4,8.0,10.9Hz),5.39(1H,dt,J=7.4,10.8Hz),5.50(1H,dt,J=7.5,10.9Hz),5.78(1H,dt,J=5.4,8.1Hz),5.86(1H,ddd,J=1.1,8.1,11.1Hz),6.43(1H,d,J=6.1Hz),6.59(1H,dd,J=11.1,12.7Hz),7.27(1H,d,J=12.7Hz),7.48(1H,d,J=6.1Hz).(Ref. 8038) ¹³C-NMR(125MHz,CDCl₃)dppm14.2,20.6,21.0,21.2,25.7,29.8,29.8,35.8,51.8,69.4,85.1,121.4,124.2,124.6,126.2,132.5,133.1,135.2,135.7,138.9,157.8,169.1,169.9,172.9,193.1.(Ref. 8038)	EIMS m/z 444 (M⁺). HREIMS m/z 384.1925 for C₂₃H₂₈O₅ (M-CH₃-CO₂H)⁺, calcd 384.1937.(Ref. 8038)			17,18-Dehydroclavulone I was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8038)					[8038]
313			sodium (4R,5E,7E)-7-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-4-hydroxy-5-heptenoate	XPR8038	Yasuji Yamada		C₂₀H₂₇O₅Na	370.415							[a]_D -92.3(C 0.16, MeOH)(Ref. 8040)		l^M^e^O^H&_m_a_x 301 nm(log e4.01),233 nm(log e4.03)(Ref. 8040)	n^fⁱ^l^m_m_a_x3382,1694,1633,1567, and 1556cm^-¹(Ref. 8040)	¹H-NMR(400MHz,CD₃OD)dppm0.93(3H,t,J=6.9Hz),1.25-1.40(6H,m),1.85-1.95(2H,brm),2.00(2H,m),2.37(2H,brm),2.72(1H,dd,J=7.4,14.0Hz),2.84(1H,dd,J=8.2,14.0Hz),4.34(1H,brm),5.16(1H,ddd,J=7.4,8.2,11.0Hz),5.45(1H,td,J=7.3,11.0Hz),6.30(1H,dd,J=5.5,15.0Hz),6.32(1H,d,J=6.0Hz),6.92(1H,d,J=11.9Hz),7.09(1H,dd,J=11.9,15.0Hz),7.40(1H,dd,J=0.8,6.0Hz).(Ref. 8040) ¹³C-NMR(100MHz,CD₃OD)dppm15.2,24.4,29.2,31.2,33.5,35.1,38.5,73.6,81.1,124.7,126.3,133.2,135.4,135.7,140.7,150.3,165.2,198.9.(Ref. 8040)	ESIMS m/z 371 (M+H)⁺. HREIMS m/z 330.1834 for C₂₀H₂₆O₄ (M-NaOH)⁺, calcd 330.1831.(Ref. 8040)	CDl^E^t^O^H&_e_x_t(De)nm 257(+5.4),230(-15.3).(Ref. 8040)		This marine prostanoidesodium solts was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8040)					[8040]
314			sodium (4R,5E,7Z)-7-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-4-hydroxy-5-heptenoate	XPR8039	Yasuji Yamada		C₂₀H₂₇O₅Na	370.415							[a]_D -83.2(C 0.095, MeOH)(Ref. 8040)		l^M^e^O^H&_m_a_x 305 nm(log e4.11),233 nm(log e4.14)(Ref. 8040)	n^fⁱ^l^m_m_a_x3382,1694,1574, and 1550cm^-¹(Ref. 8040)	¹H-NMR(400MHz,CD₃OD)dppm0.93(3H,t,J=6.9Hz),1.25-1.40(6H,m),1.88(2H,brm),2.02(2H,m),2.36(2H,brm),2.62(2H,m),4.29(1H,brm),5.26(1H,ttd,J=1.6,7.6,11.0Hz),5.48(1H,td,J=7.3,11.0Hz),6.21(1H,dd,J=5.5,15.3Hz),6.28(1H,d,J=6.0Hz),6.70(1H,d,J=11.4Hz),7.34(1H,d,J=6.0Hz),7.73(1H,dd,J=11.4,15.3Hz).(Ref. 8040) ¹³C-NMR(100MHz,CD₃OD)dppm15.2,24.4,29.1,31.1,33.4,35.2,39.0,73.6,80.6,124.9,126.7,135.2,136.7,137.2,140.1,149.4,163.0,198.7(Ref. 8040)	ESIMS m/z 371 (M+H)⁺. HREIMS m/z 330.1832 for C₂₀H₂₆O₄ (M-NaOH)⁺, calcd 330.1831.(Ref. 8040)	CDl^E^t^O^H&_e_x_t(De)nm 257(+4.0),228(-12.3).(Ref. 8040)		This marine prostanoidesodium solts was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8040)					[8040]
315		preclavulone lactone I (Ref. 8041)	(R)-4-{(Z)-3-[(1R,2S)-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenyl]-1-propenyl}-4-butanolide	XPR8040	Yasuji Yamada		C₂₀H₂₈O₃	316.435							[a]_D -168.0(Ref. 8041)		l^C^H³^C^N&_m_a_x 215 nm(e5740)(Ref. 8041)	n 1775 and 1706cm^-¹(Ref. 8041)	¹H-NMR(500MHz,CDCl₃)dppm0.89(3H,t,J=7.5Hz),1.2-1.4(6H,m),1.92(1H,dtd,8.4,9.7,12.9Hz),2.01(2H,brq,J=7.3Hz),2.11(1H,dt,J=2.3,5.9),2.27(1H,brtd,J=7.0,14.5Hz),2.32(1H,brtd,J=7.1,14.5Hz),2.41(1H,qd,J=6.6,12.9Hz),2.52(2H,m),2.57(2H,dd,J=6.6,9.7Hz),2.72(1H,qt,J=2.3,7.0Hz),5.27(1H,dt,J=6.6,8.4Hz),5.36(1H,brtd,J=7.1,10.8Hz),5.53(1H,dd,J=8.4,11.1Hz),5.54(1H,m),5.56(1H,td,J=7.2,11.1Hz),6.16(1H,dd,J=2.3,5.1Hz),7.60(1H,dd,J=2.3,5.8Hz).(Ref. 8041) ¹³C-NMR(125MHz,CDCl₃)dppm14.0,22.5,27.3,27.5,28.9,29.1,29.2,31.3,31.5,46.3,50.3,76.0,125.2,129.9,130.9,133.1,133.4,167.2,177.0,210.6(Ref. 8041)	HRFABMS m/z 316.2028 for C₂₀H₂₈O₃ (M⁺), calcd 316.2038.(Ref. 8041)			Preclavulone lactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8041)	Preclavulone lactone I was synthesized from (S)-(-)-malic acid.(Ref. 8041)	Preclavulone lactone may possibly be biosynthesized from preclavulon A. Clavulones may be biosynthesized from preclavulone lactones via clavulolactones by oxygenation at C-12, dehydration between C-7 and C-8, and esterification at C-1 and C-4. (Ref. 8041)			[8041]
316		preclavulone lactone II (Ref. 8041)	(R)-4-{(E)-3-[(1R,2S)-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenyl]-1-propenyl}-4-butanolide	XPR8041	Yasuji Yamada		C₂₀H₂₈O₃	316.435							[a]_D -110(Ref. 8041)				¹H-NMR(500MHz,CDCl₃)dppm0.89(3H,t,J=7.2Hz),1.2-1.4(6H,m),1.96(1H,m),2.00(2H,brq,J=7.3Hz),2.11(1H,m),2.27(1H,m),2.32(1H,m),2.37(1H,m),2.50(2H,m),2.52(2H,m),2.67(1H,qt,J=2.4,7.0Hz),4.89(1H,q,J=6.7Hz),5.33(1H,brtd,J=7.8,10.9Hz),5.52(1H,brtd,J=7.3,10.9Hz),5.58(1H,brdd,J=6.7,15.2Hz),5.76(1H,brtd,J=7.7,15.2Hz),6.15(1H,dd,J=2.4,5.8Hz),7.58(1H,dd,J=2.4,5.8Hz).(Ref. 8041) ¹³C-NMR(125MHz,CDCl₃)dppm14.0,22.5,27.3,28.5,28.7,29.2,31.3,31.5,33.1,46.9,50.2,80.4,125.2,130.1,131.5,133.0,133.1,166.9,176.8,210.6(Ref. 8041)				Preclavulone lactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8041)		Preclavulone lactone may possibly be biosynthesized from preclavulon A. Clavulones may be biosynthesized from preclavulone lactones via clavulolactones by oxygenation at C-12, dehydration between C-7 and C-8, and esterification at C-1 and C-4. (Ref. 8041)			[8041]
317		4-epiclavulone II (Ref. 8042)	methyl (4R,5E,7E)-4-acetoxy-7-[(R)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8042	Yasuji Yamada		C₂₅H₃₄O₇	446.533							[a]_D -18.7(C 0.30, CHCl₃)(Ref. 8042)		l^E^t^O^H_m_a_x 228 nm(log e4.28),291 nm(log e4.27)(Ref. 8042)	n^fⁱ^l^m_m_a_x1738,1732,1704,1644,and 1232cm^-¹(Ref. 8042)	¹H-NMR(500MHz,CDCl₃)dppm0.88(3H,t,J=7.2Hz),1.20-1.34(6H,m),1.94(2H,q,J=6.8Hz),1.98-2.06(2H,m),2.03(3H,s),2.09(3H,s),2.37(2H,t,J=7.4Hz),2.71(1H,dd,J=8.4,14.1Hz),2.98(1H,dd,J=7.0,14.1Hz),3.67(3H,s),5.18(1H,ddd,J=7.0,8.4,10.9Hz),5.43(1H,dt,J=6.4,7.0Hz),5.50(1H,dt,J=7.4,10.9Hz),6.07(1H,dd,J=6.4,11.9Hz),6.41(1H,d,J=6.1Hz),6.70(1H,ddd,J=1.0,11.9,15.1Hz),6.88(1H,d,J=15.1Hz),7.48(1H,d,J=6.1Hz).(Ref. 8042) ¹³C-NMR(125MHz,CDCl₃)dppm14.0,20.9,21.2,22.5,27.4,29.1,29.2,29.6,31.5,35.9,51.8,72.7,85.3,121.1,126.0,129.4,135.1,135.1,136.7,141.5,157.9,169.2,169.9,172.9,193.4.(Ref. 8042)	EIMS m/z 446 (M⁺). HREIMS m/z 446.2315 for C₂₅H₃₄O₇ (M⁺), calcd 446.2305.(Ref. 8042)			4-Epiclavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8042)	4-Epiclavulone II was synthesized from clavulone II.(Ref. 8042)				[8042]
318		4-epiclavulone III (Ref. 8042)	methyl (4R,5E,7Z)-4-acetoxy-7-[(R)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate	XPR8043	Yasuji Yamada		C₂₅H₃₄O₇	446.533							[a]_D -10.0(C 0.06, CHCl₃)(Ref. 8042)		l^E^t^O^H_m_a_x 229 nm(log e4.23),295 nm(log e4.14)(Ref. 8042)	n^fⁱ^l^m_m_a_x1738,1698 and 1229cm^-¹(Ref. 8042)	¹H-NMR(500MHz,CDCl₃)dppm0.88(3H,t,J=7.1Hz),1.21-1.34(6H,m),1.94(2H,q,J=7.3Hz),1.99-2.07(2H,m),2.03(3H,s),2.09(3H,s),2.40(2H,t,J=7.4Hz),2.63(1H,dd,J=7.3,14.2Hz),2.87(1H,dd,J=8.1,14.2Hz),3.68(3H,s),5.21(1H,ddd,J=7.3,8.1,10.9Hz),5.45(1H,dd,J=5.4,5.8Hz),5.53(1H,dt,J=7.3,10.9Hz),6.01(1H,dd,J=5.4,15.6Hz),6.35(1H,d,J=6.1Hz),6.51(1H,d,J=11.3Hz),7.51(1H,d,J=6.1Hz),7.73(1H,ddd,J=1.3,11.3,15.6Hz).(Ref. 8042) ¹³C-NMR(125MHz,CDCl₃)dppm14.0,21.0,21.7,22.5,27.4,29.0,29.2,29.7,31.5,35.6,51.7,72.4,85.2,121.3,126.3,133.4,134.7,135.6,136.7,141.0,156.1,169.7,170.2,173.2,194.1.(Ref. 8042)	EIMS m/z 446 (M⁺). HREIMS m/z 446.2328 for C₂₅H₃₄O₇ (M⁺), calcd 446.2305.(Ref. 8042)			4-Epiclavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8042)	4-Epiclavulone III was synthesized from clavulone III.(Ref. 8042)				[8042]
319		clavirin I (Ref. 8043)	(Z)-2-[(R)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]acetaldehyde	XPR8044	Yasuji Yamada		C₁₇H₂₂O₄	290.354		Clavirins showed growth-inhibitory activity toward Hela S3 at 1 mg/ml.(Ref. 8043)					[a]_D -17.1(C 0.48, CHCl₃)(Ref. 8043)			n^fⁱ^l^m_m_a_x1735,1714,1682, and 1227cm^-¹(Ref. 8043)	¹H-NMR(500MHz,CDCl₃)dppm0.88(3H,t,J=7.1Hz),1.20-1.36(6H,m),1.96(2H,brq,J=7.1Hz),2.05(3H,s),2.68(1H,dd,J=7.7,14.6Hz),2.77(1H,dd,J=7.4,14.6Hz),5.23(1H,dt,J=7.1,10.9Hz),5.59(1H,ddd,J=7.4,7.7,10.9Hz),6.21(1H,d,J=7.6Hz),6.49(1H,d,J=6.2Hz),7.56(1H,d,J=6.2Hz),10.79(1H,d,J=7.6Hz).(Ref. 8043) ¹³C-NMR(125MHz,CDCl₃)dppm14.0,21.3,22.5,27.4,29.0,31.4,36.0,83.5,120.1,129.9,136.0,136.1,150.2,169.5,11.7,192.9.(Ref. 8043)	HREIMS m/z 230.1298 for C₁₅H₁₈O₂ (M⁺-CH₃CO₂H), calcd 230.1307.(Ref. 8043)			Clavirins were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8043)	Clavirin I and II were synthesized from 4-alkoxy-2-cyclopentenone.(Ref. 8043)	Clavirins may possibly be biosynthesized from clavulone.(Ref. 8043)			[8043]
320		clavirin II (Ref. 8043)	(E)-2-[(R)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]acetaldehyde	XPR8045	Yasuji Yamada		C₁₇H₂₂O₄	290.354		Clavirins showed growth-inhibitory activity toward Hela S3 at 1 mg/ml.(Ref. 8043)					[a]_D -33.7(C 0.43, CHCl₃)(Ref. 8043)				¹H-NMR(500MHz,CDCl₃)dppm0.88(3H,t,J=7.1Hz),1.20-1.40(6H,m),1.95(2H,brq,J=7.2Hz),2.09(3H,s),2.88(1H,dd,J=7.1,14.5Hz),2.91(1H,dd,J=7.5,14.5Hz),5.23(1H,ddd,J=1.6,7.2,10.9Hz),5.62(1H,ddd,J=7.1,7.5,10.9Hz),6.53(1H,d,J=8.0Hz),6.54(1H,d,J=6.2Hz),7.65(1H,d,J=6.2Hz),10.33(1H,d,J=8.0Hz).(Ref. 8043) ¹³C-NMR(125MHz,CDCl₃)dppm14.0,21.3,22.5,27.5,28.9,31.4,37.3,84.4,120.1,125.6,134.8,136.5,149.4,159.3,169.2,190.6,192.5.(Ref. 8043)				Clavirins were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8043)	Clavirin I and II were synthesized from 4-alkoxy-2-cyclopentenone.(Ref. 8043)	Clavirins may possibly be biosynthesized from clavulone.(Ref. 8043)			[8043]
321		15-epi-prostaglandin A₂(Ref. 8044)	(5Z, 13E)-(8R,12S,15R)-15-hydroxy-9-oxoprost-5,10,13-trienoic acid	XPR8046	Yasuji Yamada	(15R)-PGA₂	C₂₀H₃₄O₄	338.482										n^fⁱ^l^m_m_a_x1350 and 970cm^-¹(Ref. 8044)	¹H-NMRdppm5.41, 5.58.(Ref. 8044)				15-Epi-prostaglandin A ₂ and its acetate methyl ester were isolated from Caribbean Gorgonian, Plexaura homomalla.(Ref. 8044)					[8044]
322		15-epi-prostaglandin A₂ acetate, methyl ester(Ref. 8044)	methyl (5Z, 13E)-(8R,12S,15R)-15-hydroxy-9-oxoprost-5,10,13-trienoate	XPR8047	Yasuji Yamada		C₂₃H₃₄O₅	390.513										n^fⁱ^l^m_m_a_x1735 and 1710cm^-¹(Ref. 8044)	¹H-NMRdppm0.89(3H,t),1.98(3H,s),3.22(1H),3.61(3H,s),5.15(1H),5.2-5.7(4H),6.12(1H,dd,J=6.12,7.44Hz),7.44(1H,dd,J=6.12,7.44Hz).(Ref. 8044)				15-Epi-prostaglandin A ₂ and its acetate methyl ester were isolated from Caribbean Gorgonian, Plexaura homomalla.(Ref. 8044)					[8044]
323		15-epi-prostaglandin E₂ acetate, methyl ester(Ref. 8045)	(5Z, 13E)-(8R,11R,12R,15R)-11,15-dihydroxy-9-oxoprost-5,13-dienoic acid	XPR8048	Yasuji Yamada	(15R)-PGE₂	C₂₀H₃₂O₅	352.465															15-Epi-prostaglandin E₂ and its methyl ester were isolated from Gorgonian, Plexaura homomalla.(Ref. 8045)					[8045]
324		15-epi-prostaglandin E₂ methyl ester(Ref. 8045)	methyl (5Z, 13E)-(8R,11R,12R,15R)-11,15-dihydroxy-9-oxoprost-5,13-dienoate	XPR8049	Yasuji Yamada		C₂₁H₃₄O₅	366.492															15-Epi-prostaglandin E₂ and its methyl ester were isolated from Gorgonian, Plexaura homomalla.(Ref. 8045)					[8045]
325		prostaglandin F₂a -11-acetate(Ref. 8046)	(5Z,13E)-(8R,9S,11R,12R,15S)-11-acetoxy-9,15-dihydroxyprost-5,13-dienoic acid	XPR8050	Yasuji Yamada		C₂₂H₃₆O₆	396.518															Prostaglandin F₂a -11-acetate was isolated from soft coral, Lobophyton depressum.(Ref. 8046)					[8046]
326		prostaglandin F₂a -11-acetate methyl ester(Ref. 8046)	methyl (5Z,13E)-(8R,9S,11R,12R,15S)-11-acetoxy-9,15-dihydroxyprost-5,13-dienoate	XPR8051	Yasuji Yamada		C₂₃H₃₈O₆	410.544			55(hexane)(Ref. 8046)							n^K^B^r&_m_a_x3700, 3610, 3510, 1740, 1730, and 970 cm^-¹(Ref. 8046)	¹H-NMR(270MHz,CDCl₃)dppm0.88(3H,t,J=6.0Hz),1.26(6H,brs),2.04(3H,s),2.32(2H,t,J=7.2Hz),2.39(1H,ddd,J=15.2,9.0,5.4Hz),2.55(1H,ddd,J=11.8,8.4,7.0Hz),3.67(3H,s),4.08(1H,q,J=6.1Hz),4.17(1H,dd,J=5.4,3.5Hz),4.90(1H,ddd,J=9.0,7.0,3.8Hz),5.41(2H,m),5.53(1H,m),5.55(1H,m).(Ref. 8046)	CIMS m/z 411 ([M⁺+1], 1), 392(7), 350(6), 332(98),314(100),288(2),282(15). (Ref. 8046)			Prostaglandin F₂a -11-acetate methyl ester was isolated from soft coral, Lobophyton depressum.(Ref. 8046)					[8046]
327		18-acetoxyprostaglandin F₂a -11-acetate(Ref. 8046)	(5Z,13E)-(8R,9S,11R,12R,15S)-11,18-diacetoxy-9,15-dihydroxyprost-5,13-dienoic acid	XPR8052	Yasuji Yamada		C₂₄H₃₈O₈	454.554															18-Acetoxyprostaglandin F₂a -11-acetate was isolated from soft coral, Lobophyton depressum.(Ref. 8046)					[8046]
328		18-acetoxyprostaglandin F₂a -11-acetate methyl ester(Ref. 8046)	methyl (5Z,13E)-(8R,9S,11R,12R,15S)-11,18-diacetoxy-9,15-dihydroxyprost-5,13-dienoate	XPR8053	Yasuji Yamada		C₂₅H₄₀O₈	468.580										nⁿ^e^a^t&_m_a_x3470,1740,1730,1715,1465,1435,1375,1260,1030, and 970cm^-¹(Ref. 8046)	¹H-NMR(270MHz,CDCl₃)dppm0.90(3H,t,J=7.2Hz),2.04(3H,s),2.31(2H,t,J=7.0Hz),2.38(1H,ddd,J=15.3,9.0,5.5Hz),2.55(1H,ddd,J=10.8,8.4,6.8Hz),3.67(3H,s),4.08(1H,dt,J=5.6,4.0Hz),4.17(1H,dd,J=5.5,3.5Hz),4.82(1H,q,J=5.3Hz),4.90(1H,ddd,J=9.0,6.8,4.0Hz),5.40(2H,m),5.54(2H,m.(Ref. 8046)	CIMS m/z 450 ([M-H₂O]⁺, 5), 408(5), 390(12), 372(16), 348(20), 330(100), 312(66), 298(18), 280(20). (Ref. 8046)			18-Acetoxyprostaglandin F₂a -11-acetate methyl ester was isolated from soft coral, Lobophyton depressum.(Ref. 8046)					[8046]
329		5-trans-prostaglandin A₂(Ref. 8047)	(5E, 13E)-(8R,12S,15S)-15-hydroxy-9-oxoprost-5,10,13-trienoic acid	XPR8054	Yasuji Yamada	5-trans-PGA₂	C₂₀H₃₀O₄	334.450							[a]_D +128(CHCl₃)(Ref. 8047)		l_m_a_x 217 nm(e9050))(Ref. 8047)			HREIMS m/z 478.2998 for TMS derivative C₂₆H₄₆O₄ Si₂, calcd 478.2932.(Ref. 8047)			5-trans-Prostaglandin A₂ was isolated from Gorgonian, Plexaura homomalla.(Ref. 8047)					[8047]

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TITLE	:	Lipoxins: Novel Series of Biologically Active Compounds Formed from Arachidonic Acid in Human Leukocytes. PubMed ID:6089195
JOURNAL	:	Proc. Nat. Acad. Sci. USA
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AUTHOR	:	Serhan, C. N., Hamberg, M., Samuelsson, B., Morris, J., and Wishka, D. G.
TITLE	:	On the stereochemistry and biosynthesis of lipoxin B PubMed ID:3083410
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AUTHOR	:	Nicolaou,K.C., and Webber,S.E.
TITLE	:	Stereocontrolled Total Synthesis of Lipoxin B.
JOURNAL	:	Synthesis
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AUTHOR	:	Corey, E. J., and Moinet, G.
TITLE	:	Direct, stereocontrolled synthesis of a prostaglandins using the bicyclo[2.2.1]heptene approach PubMed ID:4746271
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AUTHOR	:	Schneider, W. P., Bundy, G. L., Lincoln, F. H., Daniels, E. G., and Pike, J. E.
TITLE	:	Isolation and chemical conversions of prostaglandins from Plexaura homomalla: Preparation of prostaglandin E2, prostaglandin F2alpha, and their 5,6-trans isomers PubMed ID:13095
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AUTHOR	:	Cooper, G. F., and Fried, J.
TITLE	:	Carbon-13 nuclear magnetic resonance spectra of prostaglandins and some prostaglandin analogs PubMed ID:4514326
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AUTHOR	:	Floyd,M.B., Schaub,R.E., Siuta,G.J., Skotnicki,J.S., Grudzinskas,C.V., Weiss,M.J., Dessy,F., and VanHumbeeck,L.
TITLE	:	Prostaglandins and Congeners. 22. Synthesis of 11-Substituted Derivatives of 11-Deoxyprostaglandins E1 and E2. Potential Bronchodilators. PubMed ID:7401116
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AUTHOR	:	Kelly,R.C., Schletter,I, Jones,R.L.
TITLE	:	Total Synthesis of PGC2 Methyl Ester. Comparison with Enzymatically Produced Material. PubMed ID:7401116
JOURNAL	:	Prostaglandins
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AUTHOR	:	Corey,E.J., and Cyr, C.R.
TITLE	:	Transformation of Prostaglandin A2 into Prostaglandin C2.
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AUTHOR	:	Mubarik Ali,S., Chapeleo,C.B., Finch,M.A.W., Roberts,S.M., Woolley,G.T., Cave,R.J., and Newton,R.F.
TITLE	:	Preparation and Some Reactions of 2-Oxatricyclo[3.3.0.0⁴^.⁶]oct-7-en-3-one: Synthesis of 9-Deoxa-9,10-dehydroprostaglandin D2.
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AUTHOR	:	Bundy,G.L., Morton,D.R., Peterson,D.C., Nishizawa,E.E., and Miller,W.L.
TITLE	:	Synthesis and Platetet Aggregation Inhibiting Activity of Prostaglanin D Analogues. PubMed ID:6854581
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AUTHOR	:	Fitzpatrick,F.A., and Wynalda,M.A.
TITLE	:	Albumin-catalyzed Metabolism of Prostaglandin D2. Identification of Products Formed in vitro. PubMed ID:6578214
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AUTHOR	:	Kikawa, Y., Narumiya, S., Fukushima, M., Wakatsuka, H., and Hayaishi, O.
TITLE	:	9-Deoxy-delta 9, delta 12-13,14-dihydroprostaglandin D2, a metabolite of prostaglandin D2 formed in human plasma PubMed ID:6584883
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AUTHOR	:	Pace-Asciak,C.
TITLE	:	Isolation, Structure, and Biosynthesis of 6-Ketoprostaglandin F1a in the Rat Stomach. PubMed ID:1254872
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TITLE	:	Nitro-Olefin Trapping Reaction of Enolates In Situ Generated by Conjugate Addition Reaction: Short Synthesis of PGE1, 6-Oxo-PGE1, 6-Oxo-PGF1a, and PGI2.
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AUTHOR	:	Cepa, S. R., Hall, E. R., and Venton, D. L.
TITLE	:	Positive-negative, chemical-ionization, direct exposure mass spectrometry of underivatized prostaglandins PubMed ID:6547237
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AUTHOR	:	Morrison, A. R., McLaughlin, L., Bloch, M., and Needleman, P.
TITLE	:	A novel cyclooxygenase metabolite of arachidonic acid PubMed ID:6436248
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AUTHOR	:	Kindahl,H.
TITLE	:	Metabolism of Thromboxane B2 in the Cynomolgus Monkey. PubMed ID:404670
JOURNAL	:	Prostaglandins
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AUTHOR	:	Nelson, N. A., Jackson, R. W., and Sebek, O. K.
TITLE	:	Synthesis of thromboxane B2 metabolites PubMed ID:704927
JOURNAL	:	Prostaglandins.
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AUTHOR	:	Roberts, L. J., 2nd, Sweetman, B. J., and Oates, J. A.
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AUTHOR	:	Pace-Asciak, C. R., Carrara, M. C., and Domazet, Z.
TITLE	:	Identification of the major urinary metabolites of 6-ketoprostaglandin F1alpha (6K-PGF1alpha) in the rat PubMed ID:907663
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TITLE	:	A Novel Synthesis of 2,3-Dinor-6-oxo-prostaglandin F1a.
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AUTHOR	:	Hamberg, M., and Samuelsson, B.
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AUTHOR	:	Rosenberger,M., Newkom,C., and Aig,E.R.
TITLE	:	Total Synthesis of Leukotriene E4, a Member of the SRS-A Family.
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AUTHOR	:	Denis, D., Charleson, S., Rackham, A., Jones, T. R., Ford-Hutchinson, A. W., Lord, A., Cirino, M., Girard, Y., Larue, M., and Rokach, J.
TITLE	:	Synthesis and biological activities of leukotriene F4 and leukotriene F4 sulfone PubMed ID:6300970
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AUTHOR	:	Okuyama, S., Miyamoto, S., Shimoji, K., Konishi, Y., Fukushima, D., Niwa, H., Arai, Y., Toda, M., and Hayashi, M.
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TITLE	:	The synthesis of N-acetyl-leukotriene E4 and its effects on cardiovascular and respiratory function of the anesthetized pig PubMed ID:3763939
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AUTHOR	:	Kotovych,G. and Aarts,G.H.M.
TITLE	:	Homonuclear One- and Two-Dimentional Nuclear Overhauser Effect Experiments and Spin-Echo Correlated Spectroscopy. Application to Prostaglandin E1 and 6-Keto-Prostaglandin E1.
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AUTHOR	:	Walker, I. C., Jones, R. L., and Wilson, N. H.
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AUTHOR	:	Corey,E.J. and Su,W.
TITLE	:	Total Synthesis of Biologically Active Metabolites of Arachidonic Acid. The Two 8-Hydroxy-11,12(S,S)-epoxyeicosa-5,14(Z),9(E)-trienoic Acids.
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AUTHOR	:	Moghaddam, M. F., Gerwick, W. H., and Ballantine, D. L.
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AUTHOR	:	Corey,E.J., Kang,J., Laguzza,B.C. and Jones, R.L.
TITLE	:	Total Synthesis of 12-(S)-10-Hydroxy-trans-11,12-epoxyeicosa-5,9,14-(Z)-Trienoic Acids, Metabolites of Arachidonic Acid in Mammalian Blood Platelets.
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AUTHOR	:	Corey,E.J., Wright,S.W. and Matsuda,S.P.T.
TITLE	:	Stereochemistry and Mechanism of the Biosynthesis of Leukotriene A4 from 5(S)-Hydroxy-6(E),8,11,14(Z)-eicosatetraenoic Acid. Evidence for an Organoiron Intermediates.
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AUTHOR	:	Porter,N.A., Logan,J. and Kontoyiannidou,V.
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AUTHOR	:	Boeynaems, J. M., Brash, A. R., Oates, J. A., and Hubbard, W. C.
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AUTHOR	:	Corey,E.J. and Hashimoto,S.
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TITLE	:	Transformation of Arachidonic Acid and Homo-g-linolenic Acid by Rabbit Polymorphonuclear Leukocytes. Monohydroxy Acids from Novel Lipoxygenases. PubMed ID:826538
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AUTHOR	:	Corey,E.J., Niwa,H. and Knolle,J.
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AUTHOR	:	Leblanc,Y., Fitzsimmons,B.J., Adams,J., Perez,F. and Rokach,J.
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AUTHOR	:	Hawkins, D.J. and Brash,A.R.
TITLE	:	Eggs of the Sea Urchin, Strongylocentrotus purpuratus, Contain a Prominent (11R) and (12R) Lipoxygenase Activity. PubMed ID:3108255
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AUTHOR	:	Bundy, G. L., Nidy, E. G., Epps, D. E., Mizsak, S. A., and Wnuk, R. J.
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AUTHOR	:	Kikuchi,H., Tsukitani,Y., Iguchi,K., and Yamada,Y.
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AUTHOR	:	Kobayashi,M., Yasuzawa,T., Yoshihara,M., Akutsu,H., Kyogoku,Y., and Kitagawa,I.
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AUTHOR	:	Kikuchi,H., Tsukitani,Y., Iguchi,K., and Yamada,Y.
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AUTHOR	:	Corey,E.J.
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JOURNAL	:	Experientia
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AUTHOR	:	Corey,E.J., Schmidt,G., and Shimoji,K.
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AUTHOR	:	Kobayashi,M., Yasuzawa,T., Yoshihara,M., Son,B.W., Kyogoku,Y., and Kitagawa,I.
TITLE	:	Absolute Stereostructures of Claviridenone-a,b,c, and -d Four Prostanoids from the Okinawan Soft Coral Clavuraria viridis.
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AUTHOR	:	Corey,E.J., and Mehrotra,M.M.
TITLE	:	Total Synthesis of ()-Clavulones.
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AUTHOR	:	Nagaoka,H., Miyakoshi,T., and Yamada,Y.
TITLE	:	Total Synthesis of Marine Prostanoids: Clavulones.
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AUTHOR	:	Honda, A., Yamamoto, Y., Mori, Y., Yamada, Y., and Kikuchi, H.
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AUTHOR	:	Hashimoto,S., Arai,Y., and Hamanaka,N.
TITLE	:	Synthesis of Clavulones (Claviridenones).
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AUTHOR	:	Shibasaki,M., and Ogawa,Y.
TITLE	:	Total Synthesis of Clavulones.
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AUTHOR	:	Corey,E.J., Lansbury,Jr.,P.T., and Yamada,Y.
TITLE	:	Identification of a New Eicosanoid from in vitro Biosynthetic Experiments with Clavularia viridis. Implications for the biosynthesis of Clavulones.
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AUTHOR	:	Corey,E.J., D'Alarcao,M., Matsuda,S., Lansbury,P.T.Jr., and Yamada,Y.
TITLE	:	Intermediacy of 8-(R)-HPETE in the Conversion of Arachidonic Acid to Pre-clavulone a by Clavularia viridis. Implications for the Biosynthesis of Marine Prostanoids.
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AUTHOR	:	Honda, A., Hong, S., Yamada, Y., and Mori, Y.
TITLE	:	Effect of marine coral prostanoids, clavulones, on spontaneous beating rate of cultured myocardial cells from fetal mouse hearts PubMed ID:1719591
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AUTHOR	:	Klunder,A.J.H., Zwanenburg,B., and Liu,Z.Y.
TITLE	:	A Stereospecific Formal Synthesis of Clavulones from tricyclo[5.2.1.0²^.⁶]decadienone Epoxides.
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AUTHOR	:	Takemoto,M., Koshida.,A., Miyazima,K., Suzuki,K., and Achiwa,K.
TITLE	:	Prostanoids and Related Compounds. IV. Total Synthesis of Clavulones.
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AUTHOR	:	Zhu,J., Yang,J.-Y., Klunder,A.J.H., Liu,Z.-Y., and Zwanenburg,B.
TITLE	:	A Stereo- and Enantioselective Approach to Clavulones from Tricyclodecadienone using Flash Vacum Thermolysis.
JOURNAL	:	Tetrahedron
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AUTHOR	:	Takeda,K., Nakajima,A., and Yoshii,E.
TITLE	:	Synthesis of Clavulones (Claviridenones) via [3+2] Annulation using Reaction of [b-(phenylthio)acryloyl]silane with Lithium Enolate of Alkyl Methyl Ketone.
JOURNAL	:	Synlett
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AUTHOR	:	Honda, A., Mori, Y., Iguchi, K., and Yamada, Y.
TITLE	:	Structure requirements for antiproliferative and cytotoxic activities of marine coral prostanoids from the Japanese stolonifer Clavularia viridis against human myeloid leukemia cells in culture PubMed ID:3238009
JOURNAL	:	Prostaglandins.
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AUTHOR	:	Corey E.J., Matsuda, S.P.T., Nagata,R., and Cleaver, M.B.
TITLE	:	Biosynthesis of 8-R-HPETE and Preclavulone from Arachidonate in Several Species of Caribbean Coral. A Widespread Route to Marine Prostanoids.
JOURNAL	:	Tetrahedron Lett.
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AUTHOR	:	Honda, A., Mori, Y., Yamada, Y., Nakaike, S., Hayashi, H., and Otomo, S.
TITLE	:	Prolonged survival time of sarcoma 180-bearing mice treated with lipid microspheres-entrapped antitumor marine coral prostanoids PubMed ID:3187200
JOURNAL	:	Res Commun Chem Pathol Pharmacol.
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AUTHOR	:	Kikuchi,H., Tsukitani,Y., Iguchi,K., and Yamada,Y.
TITLE	:	Isolation and Structure Elucidation of New Type of Prostanoids Clavulone I, II, III, IV and Their Congeners, from the Okinawan Marine Animal Clavularia viridis Quoy and Gaimard.
JOURNAL	:	Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th
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AUTHOR	:	Honda, A., Mori, Y., Iguchi, K., and Yamada, Y.
TITLE	:	Antiproliferative and cytotoxic effects of newly discovered halogenated coral prostanoids from the Japanese stolonifer Clavularia viridis on human myeloid leukemia cells in culture PubMed ID:2890095
JOURNAL	:	Mol Pharmacol.
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AUTHOR	:	Iguchi,K., Yamada,Y., Kikuchi,H., and Tsukitani,Y.
TITLE	:	Novel C-20-oxygenated Prostanoids, 20-Acetoxyclavulones, from the Stolonifer Clavularia viridis Quoy and Gaimard.
JOURNAL	:	Tetrahedron Lett.
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AUTHOR	:	Iguchi,K., Kaneta,S., Mori,K., Yamada,Y., Honda,A., and Mori,Y.
TITLE	:	Chlorovulones, New Halogenated Marine Prostanoids with Antitumor Activity from the Stolonifer Clavularia viridis Quoy and Gaimard.
JOURNAL	:	Tetrahedron Lett.
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AUTHOR	:	Nagaoka,H., Iguchi,K., Miyakoshi,T., Yamada,N., and Yamada,Y.
TITLE	:	Determination of Absolute Configuration of Chlorovulones by CD Measurement and by Enantioselective Synthesis of (-)-Chlorovulone II.
JOURNAL	:	Tetrahedron Lett.
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AUTHOR	:	Iguchi, K., Kaneta, S., Mori, K., and Yamada, Y.
TITLE	:	A new marine epoxy prostanoid with an antiproliferative activity from the stolonifer Clavularia viridis Quoy and Gaimard PubMed ID:3435962
JOURNAL	:	Chem Pharm Bull (Tokyo).
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AUTHOR	:	Iguchi,K., Kaneta,S., Mori,K., Yamada,Y., Honda, A., and Mori, Y.
TITLE	:	Bromovulone I and Iodovulone I, Unprecedented Brominated and Iodinated Marine Prostanoids with Antitumor Activity isolated from the Japanese Stolonifer Clavularia viridis Quoy and Gaimard.
JOURNAL	:	J. Chem. Soc., Chem. Commun.
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AUTHOR	:	Baker,B.J., Okuda,R.K., Yu,P.T.K., and Scheuer, P.J.
TITLE	:	Punaglandins: Halogenated Antitumor Eicosanoids from the Octocoral Telesto riisei.
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AUTHOR	:	Nagaoka,H.,Miyaoka,H.,Miyakoshi,T., and Yamada,Y.
TITLE	:	Synthesis of Punaglandin 3 and 4. Revision of the Structures.
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AUTHOR	:	Suzuki,M.,Morita,Y.,Yanagisawa,A.,Noyori,R.,Baker,B.J., and Scheuer,P.J.
TITLE	:	Synthesis of (7E)- and (7Z)-Punaglandin 4. Structural Revision.
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AUTHOR	:	Sasai,H., and Shibasaki,M.
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AUTHOR	:	Mori,K. and Takeuchi,T.
TITLE	:	Synthesis of Punaglandin 4 by Means of Enzymatic Resolution of the Key Chlorocyclopentene Derivative.
JOURNAL	:	Tetrahedron
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AUTHOR	:	Suzuki,M.,Morita,Y.,Yanagisawa,A.,Baker,B.J.,Scheuer,P.J., and Noyori,R.
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AUTHOR	:	Iwasaki,G.,Sano,M.,Sodeoka,M.,Yoshida,K., and Shibasaki,M.
TITLE	:	Asymmetric Synthesis of (2R)-2-Hydroxy-2-(2(Z)-octenyl)-1-cyclopentanone.
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AUTHOR	:	Baker, B. J., and Scheuer, P. J.
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AUTHOR	:	Scheuer.P.J.
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AUTHOR	:	Iwashima, M., Okamoto, K., Konno, F., and Iguchi, K.
TITLE	:	New marine prostanoids from the okinawan soft coral, clavularia viridis PubMed ID:10075785
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AUTHOR	:	Iguchi, K., Iwashima, M., and Watanabe, K.
TITLE	:	Clavulolactones, New Marine Prostanoids with g-Lactonic Moiety in the a-Side-Chain from the Okinawan Soft Coral, Clavularia viridis.
JOURNAL	:	J. Nat. Prod.
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AUTHOR	:	Watanabe, K., Iwashima, M., and Iguchi, K.
TITLE	:	New Marine Prostanoid Carboxylate Salts from the Okinawan Soft Coral, Clavularia viridis.
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AUTHOR	:	Iwashima, M., Watanabe, K., and Iguchi, K.
TITLE	:	New Marine Prostanoid, Preclavulone Lactone, from the Okinawan Soft Coral, Clavularia viridis.
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AUTHOR	:	Iwashima, M., Okamoto, K., Miyai, Y., and Iguchi, K.
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AUTHOR	:	Iwashima, M., Okamoto, K., and Iguchi, K.
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[8047]

AUTHOR	:	Bundy, G. L., Daniels, E. G., Lincoln, F. H., and Pike, J. E.
TITLE	:	Isolation of a new naturally occurring prostaglandin, 5-trans-PGA 2. Synthesis of 5-trans-PGE 2 and 5-trans-PGF 2a PubMed ID:4401384
JOURNAL	:	J Am Chem Soc.
VOL	:	94 PAGE : 2124- (1972)

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