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Eicosanoid


DATA No : XPR1400 INFORMANT : Shouzo Yamamoto

NAME : 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

COMMON NAME: PROSTAGLANDIN E1
SYMBOL: PGE1
FORMULA: C20H34O5 MOL.WT (average) : 354.481


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BIOLOGICAL ACTIVITY
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).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:115-117degC (Ref. 1107)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]578=-61.6deg(C=0.56, TETRAHYDROFURAN) (Ref. 1108)

DENSITY:

SOLUBILITY:DIETHYL ETHER, ETHYL ACETATE (Ref. 1107), METHANOL (Ref. 1106), TETRAHYDROFURAN (Ref. 1108)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:METHYL ESTER ; n 1726, 1717sh, 1699, 980 cm-1 (Ref. 1109)

NMR SPECTRA: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)

MASS SPECTRA:METHYL ESTER ; m/e 350, 332, 319, 301, 279 (Ref. 1104)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
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).
CHEMICAL SYNTHESIS
(Ref. 1108)
[Table 0001]
METABOLISM
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).
GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:Bergstrom, S.
TITLE:Prostaglandins: members of a new hormonal system. These physiologically very potent compounds of ubiquitous occurrence are formed from essential fatty acids PubMed ID:4291104
JOURNAL:Science.
VOL:157 PAGE : 382-391 (1967)
[TOP]

[0002]
AUTHOR:Bergstrom, S., Carlson, L. A., and Weeks, J. R.
TITLE:The prostaglandins: a family of biologically active lipids PubMed ID:4873508
JOURNAL:Pharmacol Rev.
VOL:20 PAGE : 1-48 (1968)
[TOP]

[0082]
AUTHOR:Horton, E. W.
TITLE:Hypotheses on physiological roles of prostaglandins PubMed ID:4302663
JOURNAL:Physiol Rev.
VOL:49 PAGE : 122-161 (1969)
[TOP]

[0083]
AUTHOR:Speroff, L., and Ramwell, P. W.
TITLE:Prostaglandins in reproductive physiology PubMed ID:4914185
JOURNAL:Am J Obstet Gynecol.
VOL:107 PAGE : 1111-1130 (1970)
[TOP]

[0084]
AUTHOR:Horton, E. W.
TITLE:Biological activities of pure prostaglandins PubMed ID:5318739
JOURNAL:Experientia.
VOL:21 PAGE : 113-118 (1965)
[TOP]

[0085]
AUTHOR:Karim, S. M., Hillier, K., and Devlin, J.
TITLE:Distribution of prostaglandins E1,E2, F1-alpha and F2-alpha in some animal tissues PubMed ID:4386742
JOURNAL:J Pharm Pharmacol.
VOL:20 PAGE : 749-753 (1968)
[TOP]

[0086]
AUTHOR:Karim, S. M., Sandler, M., and Williams, E. D.
TITLE:Distribution of prostaglandins in human tissues PubMed ID:12262295
JOURNAL:Bri Pharm Chemother.
VOL:31 PAGE : 340-344 (1967)
[TOP]

[0087]
AUTHOR:Kirtland, S. J.
TITLE:Prostaglandin E1: a review PubMed ID:2901111
JOURNAL:Prostaglandins Leukot Essent Fatty Acids.
VOL:32 PAGE : 165-174 (1988)
[TOP]

[0088]
AUTHOR:Horton,E.W., and Main,I.H.M.
TITLE:The relationship between the chemical structure of prostagladnins and their biological activities.
JOURNAL:Mem. Soc. Endocr.
VOL:14 PAGE : 29 -36 (1966)
[TOP]

[0089]
AUTHOR:Ogino, N., Miyamoto, T., Yamamoto, S., and Hayaishi, O.
TITLE:Prostaglandin endoperoxide E isomerase from bovine vesicular gland microsomes, a glutathione-requiring enzyme PubMed ID:838703
JOURNAL:J Biol Chem.
VOL:252 PAGE : 890-895 (1977)
[TOP]

[1008]
AUTHOR:Lukacs,G., Piriou,F., and Gero,S.D.
TITLE:Carbon-13 Nuclear Magnetic Resonance Spectroscopy of Naturally Occurring Substances. Prostaglandins.
JOURNAL:Tetrah. Lett.
VOL: PAGE : 515 -518 (1973)
[TOP]

[1104]
AUTHOR:Hamberg, M., and Samuelsson, B.
TITLE:Prostaglandins in human seminal plasma. Prostaglandins and related factors 46 PubMed ID:5903721
JOURNAL:J Biol Chem.
VOL:241 PAGE : 257-263 (1966)
[TOP]

[1106]
AUTHOR:Struijk,M.C.B., Beerthuis,R.K., Pabon,H.J.J. and Van Dorp,D.A.
TITLE:Specificity in the Enzymic Conversion of Polyunsaturated Fatty Acids into Prostaglandins.
JOURNAL:Recueil
VOL:85 PAGE : 1233 -1250 (1966)
[TOP]

[1107]
AUTHOR:Bergströ$m,S. and Sjö$vall
TITLE:The Isolation of Prostaglandin E from Sheep Prostate Glands.
JOURNAL:Acta Chem. Scand.
VOL:14 PAGE : 1701 -1705 (1960)
[TOP]

[1108]
AUTHOR:Corey, E. J., Vlattas, I., and Harding, K.
TITLE:Total synthesis of natural (levo) and enantiomeric (dextro) forms of prostaglandin El PubMed ID:5782511
JOURNAL:J Am Chem Soc.
VOL:91 PAGE : 535-536 (1969)
[TOP]

[1109]
AUTHOR:Hayashi,M. and Miyamoto,T.
TITLE:Chemistry of Prostaglandins.
JOURNAL:Metabolism and Disease (Taisha)
VOL:12 PAGE : 1461 -1476 (1975)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.