LipidBank - Isoprenoid

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		Isopentenyl diphosphate	3-Methyl-3-butenyl diphosphate	IIP0001	Hiroshi Sagami	IPP	C₅H₈O₇P₂	242.060		The compound is an active isoprene unit commonly occurring in various organisms.														Procedures for the synthesis and purification of this compound, other 20 isoprenoid diphosphates and methanediphosphate analogues from the corresponding alcohols are found in (Ref. 0014). The synthesis of isoprenoid (phosphinylmethyl)phosphonates are described in (Ref. 0015) . Negative ion fast atom bombardment mass spectrometry (FABMS) has been used to obtain mass spectra of the naturally occurring isoprenoid metabolites including isopentenyl diphosphate, dimethylallyl diphosphate, geranyl diphosphate, and farnesyl diphosphate, presqualene diphosphate, and of several synthetic analogs including methylene-bridged diphosphates, bisphosphates, and nitrogen-containing analogs.(Ref. 0023) The study of plant polyisoprenoid alcohols including polyprenols and dolichols has been reviewed in (Ref. 0024).				[0014] / [0015] / [0023] / [0024]
2		Dimethylallyl diphosphate	3-Methyl-2-butenyl diphosphate	IIP0002	Hiroshi Sagami	DMAPP	C₅H₈O₇P₂	242.060																This compound can be synthesized from dimethylallyl alcohol (Ref. 0014).	The steroisomer of isopentenyl diphosphate and the product formed by the action of isopentenyl diphosphate isomerase.	The nucleotide sequence of isopentenyl diphosphate:dimethylallyl diphosphate isomerase (Saccharomyces cerevisiae) has been submitted to the GenBankTM/EMBL data bank with accession number J05090.(Ref. 0010)		[0010] / [0014]
3		Geranyl diphosphate, Geranyl pyrophosphate	[2E]-3,7-Dimethyl-2,6-octadien-1-yl diphosphate	IIP0003	Yoshichika Yoshioka	GOPP, GPP	C₁₀H₂₀O₇P₂	314.209		Metabolic labeling of rat liver slices with mevalonic acid revealed the accumulation of E,E,E-geranylgeranyl (di)phosphate as well as dolichyl (di)phosphate (C85 and C90) and dehydrodolichol (C85 and C90), but no accumulation of Z,E,E-geranylgeranyl (di)phosphate or E,E-farnesyl (di)phosphate was detected(Ref. 0026).														The compound can be synthesized from geraniol.(Ref. 0014)	The product formed by the action of geranyl diphosphate synthase and the first intermediate product by the action of farnesyl diphosphate synthase from dimethylallyl diphosphate and isopentenyl diphosphate. The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capacity was as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors(Ref. 0039).			[0014] / [0026] / [0039]
4		Geraniol	[2E]-3,7-Dimethyl-2,6-octadien-1-ol	IIP0004	Yoshichika Yoshioka	GOH	C₁₀H₁₈O	154.249											The 2H-labeled geraniol gave rise to 2H NMR powder patterns interpretable in terms of quadrupole splittings and splin-lattice relaxation times. Spin-lattice relaxation time measurements revealed high rates of motion for geraniol relative to cholesterol in similar membrane hosts and revealed correlation times close to the fatty acyl methyl termini in phosphatidylcholine.(Ref. 0038)						The product derived from geranyl diphosphate. The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capasity were as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors(Ref. 0039).			[0038] / [0039]
5		Farnesyl diphosphate, Farnesyl pyrophosphate	[2E,6E]-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl diphosphate	IIP0005	Yoshichika Yoshioka	FPP, FOPP	C₁₅H₂₈O₇P₂	382.326		Rat liver microsomes catalyzed the formation of Z,E,E-geranylgeranyl diphosphate from farnesyl diphosphate and isopentenyl diphosphate in the presence of Triton X-100(Ref. 0026). Metabolic labeling of rat liver slices with mevalonic acid revealed the accumulation of E,E,E-geranylgeranyl (di)phosphate as well as dolichyl (di)phosphate (C85 and C90) and dehydrodolichol (C85 and C90), but no accumulation of Z,E,E-geranylgeranyl (di)phosphate or E,E-farnesyl (di)phosphate was detected(Ref. 0026). HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture. Geranylgeranylpyrophosphate and mevalonate completely reversed the effect of the inhibitors, while farnesylpyrophosphate partially reversed it and dolichol had no effect(Ref. 0064).														The compound can be synthesized from farnesol.(Ref. 0014)	The rate of de novo synthesis of geranylgeranyl diphosphate from mevalonic acid is comparable to that of farnesyl diphosphate(Ref. 0078). Geranylgeranyl diphosphate synthase catalyzing the single condensation between isopentenyl diphosphate and farnesyl diphosphate. The enzyme required Mg2+ and Mn2+ for maximum activity. Octylglucoside showed a stimulatory effect on the enzyme activity. Farnesyl diphosphate is the common intermediate at the branch point for the synthesis of geranylgeranylated proteins as well as cholesterol, ubiquinone, dolichol, and farnesylated proteins(Ref. 0070). The uptake of F-PP and GG-PP was studied using primary cultures of chromaffin cells. Dolichylmonophosphate and isopentenylpyrophosphate promoted the uptake(Ref. 0079). The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capasity were as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors(Ref. 0039).	The crystal structure of recombinant farnesyl diphosphate synthase has been reported in (Ref. 0017). The nucleotide sequence of yeast farnesyl diphosphate synthase has been reported in (Ref. 0019). Arabidopsis thaliana contains two differentially expressed farnesyl-diphosphate genes.(Ref. 0038)		[0014] / [0017] / [0019] / [0026] / [0038] / [0039] / [0064] / [0070] / [0078] / [0079]
6		Geranylgeranyl diphosphate, Geranylgeranyl pyrophosphate	[2E,6E,10E]-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-yl diphosphate	IIP0006	Yoshichika Yoshioka	GGOPP, GGPP	C₂₀H₃₆O₇P₂	450.443		Rat liver microsomes catalyzed the formation of Z,E,E-geranylgeranyl diphosphate from farnesyl diphosphate and isopentenyl diphosphate in the presence of Triton X-100(Ref. 0026). HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture. Geranylgeranylpyrophosphate and mevalonate completely reversed the effect of the inhibitors, while farnesylpyrophosphate partially reversed it and dolichol had no effect(Ref. 0064).														The compound can be synthesized from geranylgeraniol .(Ref. 0014)	The product formed by the action of geranylgeranyl diphosphate synthase. The rate of de novo synthesis of geranylgeranyl diphosphate from mevalonic acid is comparable to that of farnesyl diphosphate(Ref. 0078). Geranylgeranyl diphosphate synthase catalyzing the single condensation between isopentenyl diphosphate and farnesyl diphosphate. The enzyme required Mg2+ and Mn2+ for maximum activity. Octylglucoside showed a stimulatory effect on the enzyme activity. Farnesyl diphosphate is the common intermediate at the branch point for the synthesis of geranylgeranylated proteins as well as cholesterol, ubiquinone, dolichol, and farnesylated proteins(Ref. 0070). Purification and properties of geranylgeranyl-diphosphate synthase from bovine brain(Ref. 0080). The uptake of F-PP and GG-PP was studied using primary cultures of chromaffin cells. Dolichylmonophosphate and isopentenylpyrophosphate promoted the uptake(Ref. 0079). The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capasity were as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors(Ref. 0039).	The nucleotide sequences of yeast Saccharomyces cerevisiae and human geranylgeranyl diphosphate synthase have been reported in (Ref. 0011)and (Ref. 0016). African swine fever virus trans-polyprenyltransferase also catalyzes mainly geranylgeranyl diphosphate from farnesyl diphosphate and isopentenyl diphosphate. (Ref. 0013)		[0011] / [0013] / [0014] / [0016] / [0026] / [0039] / [0064] / [0070] / [0078] / [0079] / [0080]
7		w-E,E,Z-Geranylgeranyl diphosphate, Cis-Geranylgeranyl diphosphate, geranylneryl diphosphate	[2Z,6E,10E]-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-yl diphosphate	IIP0007	Hiroshi Sagami		C₂₀H₃₆O₇P₂	450.443																The compound can be synthesized from cis-geranylgeraniol .(Ref. 0014)	The product formed by the action of cis-geranylgeranyl diphosphate synthase and the first product by the action of dehydrodolichul diphosphate synthase from farnesyl diphosphate and isopentenyl diphosphate.(Ref. 0026)			[0014] / [0026]
8		Geranylgeraniol	[2E,6E,10E]-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol	IIP0008	Yoshichika Yoshioka	GGOH	C₂₀H₃₄O	290.483		Geranylgeraniol had a potent apoptosis-inducing activity in HL-60 cells.(Ref. 0040) Geranylgeraniol causes a decrease in levels of calreticulin and tyrosine phosphorylation of a 36-kDa protein prior to the appearance of apoptotic features in HL-60 cells.(Ref. 0041) Geranylgeraniol potently induces caspase-3-like activity during apoptosis in human leukemia U937 cells.(Ref. 0042)															The product derived from geranylgeranyl diphosphate.			[0040] / [0041] / [0042]
9		Geranylgeranic acid, geranylgeranoic acid	[2E,6E,10E]-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenic acid	IIP0009	Yoshichika Yoshioka	GGA	C₂₀H₃₂O₂	304.467		Synthetic 4,5-didehydro geranylgeranoic acid, a potent ligand both for cellular retionoic acid-binding protein and for nuclear retinoid receptors, induced apoptosis in human hepatoma-derived cell line HuH-7 but not in primary hepatocytes, although all-trans or 9-cis retinoic acid did not induce any growth inhibition(Ref. 0081). A synthetic geranylgeranoic acid (GGA) induced apoptotic cell deth in a human hepatoma cell line, HuH-7, but not in mouse primary cultured hepatocytes. Prior to chromatin condensation, GGA induced a dramatic loss of the mitochondrial membrane potential in 1 hour and in a dose dependent manner in HuH-7 cells, but not in the primary hepatocytes. GGA induces apoptosis in hepatoma cells through derangement of mitochondrial function and subsequent activation of the cysteine protease cascade(Ref. 0082).															The product derived from geranylgeranyl diphosphate.			[0081] / [0082]
10		Geranylfarnesyl diphosphate	[2E,6E,10E,14E]-3,7,11,15,19-Pentamethyl-2,6,10,14,18-eicosapentaen-1-yl diphosphate	IIP0010	Hiroshi Sagami	GFPP	C₂₅H₄₄O₇P₂	518.560																	The product formed by the action of geranylfarnesyl diphosphate synthase.
11		Pentaprenol, Prenol-25	[2Z,6E]-3,7,11,15,19-Pentamethyl-2,6-eicosadien-1-ol	IIP0011	Hiroshi Sagami		C₂₅H₄₈O	364.648		The function is not known.													The compound was isolated from the leaves of potato, Solanum tuberosum. (Ref. 0001) and comprises a phytyl residue and a Z-a terminal residue.					[0001]
12		Hexaprenyl diphosphate, w-E,E,E,E,E-Hexaprenyl diphosphate, trans-Hexaprenyl diphosphate	[2E,6E,10E,14E,18E]-3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaen-1-yl diphosphate	IIP0012	Hiroshi Sagami		C₃₀H₅₂O₇P₂	586.677																	The product formed by the action of hexaprenyl diphosphate synthase.
13		Betulaprenol-6, Hexaprenol	[2Z,6Z,10Z,14E,18E]-3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaen-1-ol	IIP0013	Hiroshi Sagami		C₃₀H₅₀O	426.717																	The product derived from betulaprenyl (C30) diphosphate. This compound contains internal two trans isoprene residues at the w-end and the other internal isoprene residues and the a-residue are cis.(Ref. 0006/0007)			[0006] / [0007]
14		w-E,E,E,E,E,E-Heptaprenyl diphosphate, Heptaprenyl diphosphate	[2E,6E,10E,14E,18E,22E]-3,7,11,15,19,23,27-Heptamethyl-2,6,10,14,18,22,26-octacosaheptaen-1-yl diphosphate	IIP0014	Hiroshi Sagami		C₃₅H₆₀O₇P₂	654.794																	The product formed by the action of heptaprenyl diphosphate synthase. Isoprene double bonds are trans except for w-isoprene double bond.
15		Betulaprenol-7, cis-Heptaprenol	[2Z,6Z,10Z,14Z,18E,22E]-3,7,11,15,19,23,27-Heptamethyl-2,6,10,14,18,22,26-octacosaheptaen-1-ol	IIP0015	Hiroshi Sagami		C₃₅H₅₈O	494.834																	The product derived from betulaprenyl (C35) diphosphate. This compound contains internal two trans isoprene residues at the w-end and the other internal isoprene residues and the a-residue are cis.(Ref. 0006/0007)			[0006] / [0007]
16		Octaprenyl diphosphate, trans-Octaprenyl diphosphate	[2E,6E,10E,14E,18E,22E,26E]-3,7,11,15,19,23,27,31-Octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaen-1-yl diphosphate	IIP0016	Hiroshi Sagami		C₄₀H₆₈O₇P₂	722.911																	The product formed by the action of octaprenyl diphosphate synthase. This compound contains trans isoprene double bonds except for w isoprene double bond.	The amino acid sequence of Escherichia coli octaprenyl diphosphate synthase has (GenBank accession no. U18997) been reported in (Ref. 0018).		[0018]
17		Betulaprenol-8, Octaprenol	[2Z,6Z,10Z,14Z,18Z,22E,26E]-3,7,11,15,19,23,27,31-Octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaen-1-ol	IIP0017	Hiroshi Sagami		C₄₀H₆₆O	562.951																	The product derived from betulaprenyl (C40) diphosphate. This contains internal two trans isoprene residues at the w-end and the other internal isoprene residues and the a-residue are cis.(Ref. 0006/0007)			[0006] / [0007]
18		Bombiprenone	[all-E]- 6,10,14,18,22,26,30,34-octamethyl-5,9,13,17,21,25,29,33-pentatriacontaoctaen-2-one	IIP0018	Hiroshi Sagami		C₄₃H₇₀O	603.015															The compound was isolated from silkworm feces.(Ref. 0004)					[0004]
19		Solanesyl diphosphate, Nonaprenyl diphosphate	[2E,6E,10E,14E,18E,22E,26E,30E]-3,7,11,15,19,23,27,31,35-Nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaen-1-yl diphosphate	IIP0019	Hiroshi Sagami		C₄₅H₇₆O₇P₂	791.028																	The product formed by the action of nonaprenyl diphosphate synthase.	The amino acid sequence of solanesyl diphosphate synthase from Rhodobacter capsulatus (Ref. 0012).		[0012]
20		Nor-solanesene	[all-E]- 2,6,10,14,18,22,26,30,34-Nonamethyl-1,5,9,13,17,21,25,29,33-pentatriacotanonaene	IIP0020	Hiroshi Sagami		C₄₄H₇₂	601.042															The compound was isolated from tabacco.(Ref. 0005)					[0005]
21		Betulaprenol-9, Nonaprenol	[2Z,6Z,10Z,14Z,18Z,22Z,26E,30E]-3,7,11,15,19,23,27,31,35-Nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaen-1-ol	IIP0021	Hiroshi Sagami		C₄₅H₇₄O	631.068																	The product derived from betulaprenyl (C45) diphosphate. This contains internal two trans isoprene residues at the w-end and the other internal isoprene residues and the a-residue are cis.(Ref. 0007)			[0007]
22		Glycinoprenol-9, Hexahydrononaprenol	[2Z,6Z,10Z,14Z,18Z,22E]-3,7,11,15,19,23,27,31,35-Nonamethyl-2,6,10,14,18,22-hexatriacontahexaen-1-ol	IIP0022	Hiroshi Sagami		C₄₅H₈₀O	637.116		The function is not known.													The compound was isolated from the leaves of soybean.(Ref. 0002)		The compound contains a phytyl residue at the w-terminal.			[0002]
23		Decaprenyl diphosphate, trans-decaprenyl diphosphate	[2E,6E,10E,14E,18E,22E,26E,30E,34E]-3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-yl diphosphate	IIP0023	Hiroshi Sagami		C₅₀H₈₄O₇P₂	859.145																	The product formed by the action of decaprenyl diphosphate synthase.
24		wt2c7-Decaprenol, cis-Decaprenol	[2Z,6Z,10Z,14Z,18Z,22Z,26Z,30E,34E]-3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-ol	IIP0024	Hiroshi Sagami		C₅₀H₈₂O	699.185															The compound was isolated from bovine pituitary glands.(Ref. 0025)					[0025]
25		cis-Decaprenol, wt3c6-Decaprenol	[2Z,6Z,10Z,14Z,18Z,22Z,26E,30E,34E]-3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-ol	IIP0025	Hiroshi Sagami		C₅₀H₈₂O	699.185															The compound was isolated from bovine pituitary glands.(Ref. 0025)					[0025]
26		Glycinoprenol-10	[2Z,6Z,10Z,14Z,18Z,22Z,26E]-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26-tetracontaheptaen-1-ol	IIP0026	Hiroshi Sagami		C₅₀H₈₈O	705.233															The compound was isolated from the leaves of soybean.(Ref. 0002) This contains a phytyl residue at the w-terminal.					[0002]
27		Undecaprenyl diphosphate, wt2c8-C55-prenyl diphosphate	[2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E]-3,7,11,15,19,23,27,31,35,39,43-Undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaen-1-yl diphosphate	IIP0027	Hiroshi Sagami		C₅₅H₉₀O₇P₂	925.246																	The compound is synthesized by the action of undecaprenyl diphosphate synthase.	The nucleotide sequence of Micrococcus luteus undecaprenyl diphosphate synthase (Ref. 0020).		[0020]
28		Undecaprenol, wt3c7-C55-prenol, Prenol-11	[2Z,6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E]-3,7,11,15,19,23,27,31,35,39,43-Undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaen-1-ol	IIP0028	Hiroshi Sagami		C₅₅H₉₀O	767.303											1H-NMR spectrum at 100MHz (with spectrum)(Ref. 0021). The head and tail sites of undecaprenol exibit a fast motion as exibited in the short chain isoprenols. Undecaprenol appears to induce a non-bilayer (isotropic) organization of phospholipid molecules in PE/PC (2:1) vesicles.(Ref. 0085)	(with spectrum)(Ref. 0021)			The compound was isolated from silkworm feces.(Ref. 0003) Plant(Ref. 0021).				The effect of dolichols, polyprenols, dolichol esterified with fatty acids, and dolichyl phosphate on the structure and fluidity of model membranes was studied using 31P NMR, small-angle x-ray scattering, differential scanning calorimetry, and freeze-fracture electron microscopy. Dolichol and dolichol derivatives destabilize unsaturated phosphatidylethanolamine containing bilayer structures and promote hexagonal II phase formation. Dolichol and dolichyl-P increase the fatty acid fluidity in phosphatidylethanolamine mixtures(Ref. 0044).	[0003] / [0021] / [0044] / [0085]
29		C55-dolichol, wt3c6-C55-dolichol, a-Dihydroundecaprenol, Dolichol-11	[6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E]-3,7,11,15,19,23,27,31,35,39,43-Undecamethyl-6,10,14,18,22,26,30,34,38,42-tetratetracontadecaen-1-ol	IIP0029	Yoshichika Yoshioka	Dol-11	C₅₅H₉₂O	769.318		The biological role of dolichol (review)(Ref. 0043).									1H-NMR spectrum at 100MHz (with spectrum)(Ref. 0021).	m/z=768 (with spectrum)(Ref. 0021).			The compound was isolated from pig liver.(Ref. 0021)	Chemical hydrogenation of plant undecaprenol(Ref. 0021).			Dolichol-11 from pig liver was identified as cis/trans-dihydroundecaprenol in which the OH-terminal isoprene residue was saturated(Ref. 0021). The effect of dolichols, polyprenols, dolichol esterified with fatty acids, and dolichyl phosphate on the structure and fluidity of model membranes was studied using 31P NMR, small-angle x-ray scattering, differential scanning calorimetry, and freeze-fracture electron microscopy. Dolichol and dolichol derivatives destabilize unsaturated phosphatidylethanolamine containing bilayer structures and promote hexagonal II phase formation. Dolichol and dolichyl-P increase the fatty acid fluidity in phosphatidylethanolamine mixtures(Ref. 0044).	[0021] / [0043] / [0044]
30		exo-Methylene-hexahydroprenol-18	exo-Methylene-hexahydroprenol-18	IIP0030	Hiroshi Sagami		C₉₁H₁₅₂O	1262.180															The compound was isolated from Aspergillus niger.(Ref. 0008)					[0008]
31		Dolichol-19, a-Dihydrononadecaprenol	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66E,70E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75-Nonadecamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74-hexaheptacontaoctadecaen-1-ol	IIP0031	Yoshichika Yoshioka	DOL-19	C₉₅H₁₅₆O	1314.255		The compound functions as a sugar carrier lipid in the glycoprotein biosynthesis. The biological role of dolichol (review)(Ref. 0043). Content of dolichol and activity of GlcNAc-1-P (UDP-N-acetylglucosamine:dolichyl phosphate N-acetylglucosamine 1-phosphate transferase) in fibroblasts from patients with carbohydrate-deficient glycoprotein (CDG) syndrome were analyzed. The major defect of CDG syndrome is not found in the synthesys of dolichyl phosphate or GlcNAc-PP-Dol(Ref. 0061). The influence of dolichol on microsomal membrane functions: Dolichol affected microsomal membrane fluidity, but did not modify the activities of certain microsome membrane enzymes(Ref. 0062). Dolichol was covalently bound to cellular proteins with size of 5, 10, 27, 75, and >140 kDa(Ref. 0063). Dolichyl, dihydroheptaprenyl, and dihydrodecaprenyl phosphates induced apoptosis in U937 cells, while farnesyl phosphate, geranylgeranyl phosphate, dolichol, dolichal, and dlichoic acid did not induce apoptosis. Apoptosis induced by dihydroprenyl phosphate was mediated by caspase-3-like activation but not by caspase-1-like activation(Ref. 0065).								IR spectrum was observed(Ref. 0084).	1H-NMR spectrum at 100MHz (with spectrum)(Ref. 0084/0021). The arrangement of isoprene units in pig liver dolichol was determined by 1H- and 13C-NMR spectroscopy. 1H-NMR at 200MHz, 13C-NMR at 50.1MHz (with spectra)(Ref. 0045). The head and tail sites of dolichol exibit a fast motion as exibited in the short chain isoprenols. Dolichol appears to induce a non-bilayer (isotropic) organization of phospholipid molecules in PE/PC (2:1) vesicles(Ref. 0085).	m/z=1312 (19 isoprene units)(Ref. 0084).		HPLC (with chromatograph)(Ref. 0046/0047/0048/0049/0050/0051). Separation of dolichol from dehydrodolichol by a simple two-plate thin-layer chromatography(Ref. 0052). Sequential microanalyses of free dolichol, dolichyl fatty acid ester and dolichyl phosphate in human serum were made fluorometrically by HPLC. The calibration curve of dolichol standard against the internal standard showed linearity at dolichol concentrations of 10ng to 500ng(Ref. 0053).	The compound was isolated from human kidney, ox kidney, pig heart, pig liver, rat liver, and ox intestine.(Ref. 0009). Beef and human pituitaries(Ref. 0083/0084>. Pig liver(Ref. 0021). Human tissues(Ref. 0054). Mouse testes(Ref. 0046). Rat and human tissues (Ref. 0048). Distribution in rat liver subcellular organelles (Ref. 0048). Contents in human tissues (Ref. 0055). Rat and human tissues (spleen, liver, kidney, myocardium, lung, pancreas, adrenal)(Ref. 0051). Levels of dolichol in neonatal and adult human tissues (thyroid, testis, liver, heart, kidney, lung, spleen)(Ref. 0056). Content in human serum(Ref. 0053). The effects of dietary proteins on the accumulation of dolichol in kidney, spleen, brain, and heart (Ref. 0057). Dolichol content in different regions of the rat brain (cerebral cortex, striatum, hippocampus, cerebellum, and brain stem) (Ref. 0058). Content of dolichol and retinol in isolated rat non-parenchymal liver cells(Ref. 0059). Distribution of radiolabeled dolichol in rat liver fractions (Ref. 0060).					[0009] / [0021] / [0043] / [0045] / [0046] / [0047] / [0048] / [0049] / [0050] / [0051] / [0052] / [0053] / [0054] / [0055] / [0056] / [0057] / [0058] / [0059] / [0060] / [0061] / [0062] / [0063] / [0065] / [0083] / [0084] / [0085]
32		exo-Methylene-hexhydroprenol-19	exo-Methylene-hexhydroprenol-19	IIP0032	Hiroshi Sagami		C₉₆H₁₆₀O	1330.297															The compound was isolated from Aspergillus niger.(Ref. 0008)					[0008]
33		Dolichol-20, a-Dihydroeicosaprenol	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66Z,70E,74E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79-Eicosamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78-octacontanonadecaen-1-ol	IIP0033	Yoshichika Yoshioka	Dol-20	C₁₀₀H₁₆₄O	1382.372		The biological role of dolichol (review)(Ref. 0043). Content of dolichol and activity of GlcNAc-1-P (UDP-N-acetylglucosamine:dolichyl phosphate N-acetylglucosamine 1-phosphate transferase) in fibroblasts from patients with carbohydrate-deficient glycoprotein (CDG) syndrome (Ref. 0061). Extraction of microsomes with n-heptane and subsequent reincorporation of dolichol were done in order to investigate the influence of dolichol on microsomal membrane functions. Dolichol affected microsomal membrane fluidity, but did not modify the activities of certain microsome membrane enzymes(Ref. 0062). Dolichol was covalently bound to cellular proteins with size of 5, 10, 27, 75, and >140 kDa(Ref. 0063). HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture(Ref. 0064). Dolichyl, dihydroheptaprenyl, and dihydrodecaprenyl phosphates induced apoptosis in U937 cells. Apoptosis induced by dihydroprenyl phosphate was mediated by caspase-3-like activation but not by caspase-1-like activation(Ref. 0065).									The arrangement of isoprene units in pig liver dolichol was determined by 1H- and 13C-NMR spectroscopy. 1H-NMR at 200MHz, 13C-NMR at 50.1MHz (with spectra)(Ref. 0045).			HPLC (with chromatograph)(Ref. 0046/0047/0048/0049/0050/0051). Separation of dolichol from dehydrodolichol by a simple two-plate thin-layer chromatography(Ref. 0052). Sequential microanalyses of free dolichol, dolichyl fatty acid ester and dolichyl phosphate in human serum were made fluorometrically by HPLC. The calibration curve of dolichol standard against the internal standard showed linearity at dolichol concentrations of 10ng to 500ng(Ref. 0053).	The compound was isolated from human kidney, ox kidney, pig heart, pig liver, rat liver, and ox intestine.(Ref. 0009/0022). Human tissues (Ref. 0054). Mouse testes(Ref. 0046). Rat and human tissues (Ref. 0048). Distribution in rat liver subcellular organelles (Ref. 0048). Contents in human tissues (Ref. 0055). Rat and human tissues (spleen, liver, kidney, myocardium, lung, pancreas, adrenal)(Ref. 0051). Levels of dolichol in neonatal and adult human tissues (Ref. 0056). Content in human serum(Ref. 0053). The effects of dietary proteins on the accumulation of dolichol (Ref. 0057). Dolichol content in different regions of the rat brain (cerebral cortex, striatum, hippocampus, cerebellum, and brain stem) were analyzed from birth to the age of 2 years. The level of dolichol increased almost 100-fold during the first 10 months of life and continued to increase thereafter(Ref. 0058). Content of dolichol and retinol in isolated rat non-parenchymal liver cells(Ref. 0059). Distribution of radiolabeled dolichol in rat liver fractions (nuclei, debris, mitochondria, lysosomes, microsomes, Golgi, cytosol)(Ref. 0060).		Incorporation of tritium from tritiated water into dolichol (Ref. 0066). Age-associated changes in dolichol metabolism (Ref. 0066). Elevated dolichol synthesis during spermatogenesis(Ref. 0046). Synthesis in liver of normal and mutant mice(Ref. 0046). Presence of abnormal amounts of dolichols (Ref. 0047). Rat liver hyperplastic nodules(Ref. 0048). Human liver cirrosis and hepatocarcinoma(Ref. 0048). Brain dolichols (Ref. 0049). Content of cerebral cortex during aging (Ref. 0049). Composition of isolated pronase-treated cytosome fractions (Ref. 0049). The content in hyperplastic nodules and developed hepatocarcinoma(Ref. 0050). Effect of age (Ref. 0067). Content in cerebral cortex of ceroid-lipofuscinosis(Ref. 0068). Age-related chnges of dolichyl phosphate content (Ref. 0051). Biosynthesis of dolichol from mevalonic acid (Ref. 0069). Farnesyl diphosphate is the common intermediate (Ref. 0070). Dolichol contents of various organs of mice(Ref. 0071). The effects of TSH on dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells (Ref. 0072). Dehydrodolichol is a common branch point intermediate(Ref. 0073).		Metabolism of dolichol, dolichoic acid, and nordolichoic acid in MDCK and HepG2 cells (Ref. 0074). The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway (Ref. 0039). Age-dependent changes in hepatic dolichol content in rats fed either ad libitum, or subjected to restriction of daily food intake or every-other-day feeding ad libitum(Ref. 0075/0076). The effects of alcohol and glucagon on the biliary excretion of dolichols in rats (Ref. 0077). Modifications in the concentration and distribution of rat liver microsomal dolichol and dolichyl phosphate after acute ethanol adiministration (Ref. 0059). Pro-oxidant agents lead to a significant decrease of both free dolichol and dolichyl phosphate in isolated rat hepatocytes(Ref. 0059). Distribution of radiolabeled dolichol in rat liver fractions(Ref. 0060). The effect of dolichols, polyprenols, dolichol esterified with fatty acids, and dolichyl phosphate on the structure and fluidity of model membranes was studied using 31P NMR, small-angle x-ray scattering, differential scanning calorimetry, and freeze-fracture electron microscopy. (Ref. 0044).	[0009] / [0022] / [0039] / [0043] / [0044] / [0045] / [0046] / [0047] / [0048] / [0049] / [0050] / [0051] / [0052] / [0053] / [0054] / [0055] / [0056] / [0057] / [0058] / [0059] / [0060] / [0061] / [0062] / [0063] / [0064] / [0065] / [0066] / [0067] / [0068] / [0069] / [0070] / [0071] / [0072] / [0073] / [0074] / [0075] / [0076] / [0077]
34		exo-Methylene-hexahydroprenol-20	exo-Methylene-hexahydroprenol-20	IIP0034	Hiroshi Sagami		C₁₀₁H₁₆₈O	1398.414															The compound was isolated from Aspergillus niger.(Ref. 0008)					[0008]
35		exo-Methylene-hexahydroprenol-21	exo-Methylene-hexahydroprenol-21	IIP0035	Hiroshi Sagami		C₁₀₆H₁₇₆O	1466.531															The compound was isolated from Aspergillus niger.(Ref. 0008)					[0008]
36		exo-Methylene-hexhydroprenol-22	exo-Methylene-hexhydroprenol-22	IIP0036	Hiroshi Sagami		C₁₁₁H₁₈₄O	1534.648															The compound was isolated from Aspergillus niger.(Ref. 0008)					[0008]
37		exo-Methylene-hexhydroprenol-23	exo-Methylene-hexhydroprenol-23	IIP0037	Hiroshi Sagami		C₁₁₆H₁₉₂O	1602.765															The compound was isolated from Aspergillus niger.(Ref. 0008)					[0008]
38		exo-Methylene-hexahydroprenol-24	exo-Methylene-hexahydroprenol-24	IIP0038	Hiroshi Sagami		C₁₂₁H₂₀₀O	1670.882															The compound was isolated from Aspergillus niger.(Ref. 0008)					[0008]
39		Phytyl diphosphate	[2E]-3,7,11,15-Tetramethyl-2-hexadecen-1-yl diphosphate	IIP0039	Hiroshi Sagami		C₂₀H₄₂O₇P₂	456.491																	The compound is formed from geranylgeranyl diphosphate by the action of geranylgeranyl reductase.	The nucleotide sequence of geranylgeranyl reductase is shown in (Ref. 0027).		[0027]
40		Dolichol-16, a-Dihydrohexadecaprenol	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54E,58E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-Hexadecamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-tetrahexacontapentadecaen-1-ol	IIP0040	Yoshichika Yoshioka	Dol-16	C₈₀H₁₃₂O	1109.903		The biological role of dolichol (review)(Ref. 0043).												Separation of dolichol from dehydrodolichol by a simple two-plate thin-layer chromatography(Ref. 0052).	The compound was found as prenol in Schizosaccharomyces pombe(Ref. 0028). Dolichol content in different regions of the rat brain (cerebral cortex, striatum, hippocampus, cerebellum, and brain stem) were analyzed from birth to the age of 2 years. The level of dolichol increased almost 100-fold during the first 10 months of life and continued to increase thereafter(Ref. 0058).		Incorporation of tritium from tritiated water into dolichol in the kidneys and liver of mice as a function of age(Ref. 0066). Age-associated changes in dolichol metabolism in the kidneys and liver of mice(Ref. 0066). Dolichol contents of various organs of mice used as a model for Niemann-Pick's type C disease (liver, spleen, kidney, brain, testis, lung, adipose tissue, heart, intestine, skeletal muscle). Contents in subfractions isolated from the liver of mice used as a model for NPC (mitocondria, lysosomes, microsomes)(Ref. 0071). The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capasity were as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors(Ref. 0039).			[0028] / [0039] / [0043] / [0052] / [0058] / [0066] / [0071]
41		Dolichol-17, a-Dihydroheptadecaprenol	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58E,62E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67-Heptadecamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66-octahexacontahexadecaen-1-ol	IIP0041	Yoshichika Yoshioka	Dol-17	C₈₅H₁₄₀O	1178.020		The biological role of dolichol (review) (Ref. 0043). Content of dolichol and activity of GlcNAc-1-P (UDP-N-acetylglucosamine:dolichyl phosphate N-acetylglucosamine 1-phosphate transferase) in fibroblasts from patients with carbohydrate-deficient glycoprotein (CDG) syndrome (Ref. 0061). Extraction of microsomes with n-heptane and subsequent reincorporation of dolichol were done in order to investigate the influence of dolichol on microsomal membrane functions. Dolichol affected microsomal membrane fluidity, but did not modify the activities of certain microsome membrane enzymes(Ref. 0062). Dolichol was covalently bound to cellular proteins with size of 5, 10, 27, 75, and >140 kDa(Ref. 0063). Dolichyl, dihydroheptaprenyl, and dihydrodecaprenyl phosphates induced apoptosis in U937 cells, while farnesyl phosphate, geranylgeranyl phosphate, dolichol, dolichal, and dlichoic acid did not induce apoptosis. Apoptosis induced by dihydroprenyl phosphate was mediated by caspase-3-like activation but not by caspase-1-like activation(Ref. 0065).												HPLC (with chromatograph)(Ref. 0046/0048/0050/0051). Separation of dolichol from dehydrodolichol by a simple two-plate thin-layer chromatography(Ref. 0052). Sequential microanalyses of free dolichol, dolichyl fatty acid ester and dolichyl phosphate in human serum were made fluorometrically by HPLC. The calibration curve of dolichol standard against the internal standard showed linearity at dolichol concentrations of 10ng to 500ng(Ref. 0053).	The compound was found as prenol in Schizosaccharomyces pombe(Ref. 0028). Human tissues (Ref. 0054). Mouse testes(Ref. 0046). Rat and human tissues(Ref. 0048). In rat liver, outer mitochondrial and Golgi membranes, lysosomes and plasmamembranes contain considerable amounts of dolichol(Ref. 0048). Contents in human tissues (Ref. 0055). Rat and human tissues(Ref. 0051). Levels of dolichol in neonatal and adult human tissues (Ref. 0056). Content in human serum(Ref. 0053). The effects of dietary proteins on the accumulation of dolichol in kidney, spleen, brain, and heart were studied. There were increases in dolichol contents in rat tissues with age. The contents of kidney and spleen were influenced by the diet(Ref. 0057). Dolichol content in different regions of the rat brain were analyzed from birth to the age of 2 years. The level of dolichol increased almost 100-fold during the first 10 months of life and continued to increase thereafter(Ref. 0058). Content of dolichol and retinol in isolated rat non-parenchymal liver cells(Ref. 0059). Distribution of radiolabeled dolichol in rat liver fractions (Ref. 0060).		Incorporation of tritium from tritiated water into dolichol (Ref. 0066). Age-associated changes in dolichol metabolism (Ref. 0066). Elevated dolichol synthesis during spermatogenesis(Ref. 0046). Synthesis in liver of normal and mutant mice(Ref. 0046). Rat liver hyperplastic nodules(Ref. 0048). Human liver cirrosis and hepatocarcinoma(Ref. 0048). The content in hyperplastic nodules of rat liver (Ref. 0050). Effect of age on the content in brain, liver, spleen, kidney, and testis of the rat(Ref. 0067). Content in cerebral cortex of ceroid-lipofuscinosis(Ref. 0068). Age-related chnges of dolichyl phosphate content (Ref. 0051). Farnesyl diphosphate is the common intermediate (Ref. 0070). Dolichol contents of various organs of mice (Ref. 0071). The effects of TSH on dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells (Ref. 0072). Dehydrodolichol is a common branch point intermediate (Ref. 0073). Metabolism of dolichol, dolichoic acid, and nordolichoic acid (Ref. 0074). The potential for feedback inhibition by isoprene intermediates (Ref. 0039).		Age-dependent changes in hepatic dolichol content in rats fed either ad libitum, or subjected to restriction of daily food intake or every-other-day feeding ad libitum (Ref. 0075/0076). The effects of alchol and glucagon on the biliary excretion of dolichols in rats were investigated. Chronic ethanol treatment decreased both biliary dolichol and beta-hexosaminidase excretion. (Ref. 0077). Modifications in the concentration and distribution of rat liver microsomal dolichol and dolichyl phosphate after acute ethanol adiministration (6 g/kg body weight) were investigated. Between 3 and 24 hr after ethanol administration, the microsomal dolichyl phosphate concentration was significantly lower than in control rats. An earlier and more marked reduction of total dolichol was observed in the Golgi apparatus(Ref. 0059). Pro-oxidant agents lead to a significant decrease of both free dolichol and dolichyl phosphate in isolated rat hepatocytes(Ref. 0059). Distribution of radiolabeled dolichol in rat liver fractions(Ref. 0060).	[0028] / [0039] / [0043] / [0046] / [0048] / [0050] / [0051] / [0052] / [0053] / [0054] / [0055] / [0056] / [0057] / [0058] / [0059] / [0060] / [0061] / [0062] / [0063] / [0065] / [0066] / [0067] / [0068] / [0070] / [0071] / [0072] / [0073] / [0074] / [0075] / [0076] / [0077]
42		Squalene	2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetraacosahexaene	IIP0042	Hiroshi Sagami		C₃₀H₅₀	410.718															The compound was isolated from Halobacterium cutirubrum with its di- and tetrahydrosqualenes(Ref. 0029).			Molecular cloning of the yeast gene for squalene synthetase(Ref. 0030)		[0029] / [0030]
43		2-Demethylplastoquinol, 2-Methyl-6-nonaprenylbenzoquinol		IIP0043	Hiroshi Sagami		C₅₂H₈₀O₂	737.190																	The compound is formed from homogentisate and nonaprenyl pyrophosphate by the action of homogentisate decarboxylase-nonaprenyltransferase(Ref. 0031).			[0031]
44		Aspulvinone H		IIP0044	Hiroshi Sagami		C₂₇H₂₈O₅	432.508																	The compound is formed from Aspulvinone E and dimethylallyl diphosphate by the action of dimethylallyl pyrophosphate:aspulvinone dimethylallyltransferase.(Ref. 0032)			[0032]
45		Aspulvinone J		IIP0045	Hiroshi Sagami		C₂₇H₂₈O₃	400.509																	The compound is formed from Aspulvinone G and dimethylallyl diphosphate by the action of dimethylallyl pyrophosphate:aspulvinone dimethylallyltransferase.(Ref. 0032)			[0032]
46		3-Nonaprenyl-4-hydroxybenzoate		IIP0046	Hiroshi Sagami		C₅₂H₇₈O₃	751.174																	The compound is formed from 4-hydroxybenzoate derived from tyrosine metabolism and nonaprenyl pyrophosphate derived from mevalonic acid by the action of 4-hydroxybenzoate polyprenyltransferase (Ref. 0033).This is the major product of the enzymatic reaction in rat liver.			[0033]
47		3-Decaprenyl-4-hydroxybenzoate		IIP0047	Hiroshi Sagami		C₅₇H₈₆O₃	819.291																	The compound is formed from 4-hydroxybenzoate derived from tyrosine metabolism and decaprenyl pyrophosphate derived from mevalonic acid by the action of 4-hydroxybenzoate polyprenyltransferase (Ref. 0033). This is the major product of the enzymatic reaction in human and guinea pig.			[0033]
48		4-Dimethylallyltryptophan		IIP0048	Hiroshi Sagami		C₁₆H₂₀O₂N₂	272.342																	The compound is formed from tryptophan and dimethylallyl pyrophosphate by the action of dimethylallylpyrophosphate:L-tryptophan dimethylallyltransferase(Ref. 0034).			[0034]
49		Isopentenyladenine		IIP0049	Hiroshi Sagami		C₁₀H₁₃N₅	203.244		The compound acts as a mediator of mevalonate-regulated DNA replication (Ref. 0035).													Isolation procedures are described in (Ref. 0036).					[0035] / [0036]
50		Dimethylallyladenosine5'-phosphate, N⁶-(d²-isopentenyl)adenosine5'-phosphate, N⁶-(g,g-dimethylallyl)adenosine5'-phosphate		IIP0050	Hiroshi Sagami	iPA-5'P, iPeAde-5'P	C₁₅H₂₂O₇N₅P₁	415.338																	The compound is formed from 5'-AMP and dimethylallyl pyrophosphate by the action of dimethylallyladenosine 5'-AMP dimethylallyltransferase(Ref. 0037).			[0037]
51		Farnesol	3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol	IIP0051	Yoshichika Yoshioka	FOH	C₁₅H₂₆O	222.366		Farnesol inhibited growth of leukemia cells (CEM-C1) without causing cell lysis.(Ref. 0086) Farnesol inhibited phosphatidylcholine biosynthesis in cultured cells dy decreasing cholinephosphotransferase activity.(Ref. 0087) In HeLa cells farnesol caused translocation of PKC from membrane fraction to cytosol after 1hr of incubation and also prevented PMA-stimulated induction of PKC translocation from cytosol to membranes.(Ref. 0088)		120 degree Celsius (at 0.2 mmHg)							The 2H-labeled farnesol gave rise to 2H NMR powder patterns interpretable in terms of quadrupole splittings and splin-lattice relaxation times. Spin-lattice relaxation time measurements revealed high rates of motion for geraniol relative to cholesterol in similar membrane hosts and revealed correlation times close to the fatty acyl methyl termini in phosphatidylcholine.(Ref. 0038)				Pig liver(Ref. 0021).		Incorporation of mevalonic acid-derived materials into proteins was studied with extremely halophilic archaebacteria, Halobacterium halobium and Halobacterium cutirubrum. The amount of farnesylated proteins was very small in H. halobium(Ref. 0089). The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capasity were as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors(Ref. 0039).		Tree dimansional structure(Ref. 0090).	[0021] / [0038] / [0039] / [0086] / [0087] / [0088] / [0089] / [0090]
52		Geranylfarnesol	3,7,11,15,18-Pentamethyl-2,6,10,14,18-eicosapentaen-1-ol	IIP0052	Yoshichika Yoshioka	GFOH	C₂₅H₄₂O	358.600		Geranylfarnesol had a potent apoptosis-inducing activity in HL-60 cells.(Ref. 0040)																		[0040]
53		Solanesol, Prenol-9, Nonaprenol	[2E,6E,10E,14E,18E,22E,26E,30E]-3,7,11,15,19,23,27,31,35-Nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaene-1-ol	IIP0053	Yoshichika Yoshioka		C₄₅H₇₄O	631.068											The 2H-labeled solanesol gave rise to 2H NMR powder patterns interpretable in terms of quadrupole splittings and splin-lattice relaxation times. Spin-lattice relaxation time measurements revealed high rates of motion for geraniol relative to cholesterol in similar membrane hosts and revealed correlation times close to the fatty acyl methyl termini in phosphatidylcholine.(Ref. 0038)									[0038]
54		Decaprenol, Prenol-10	[2E,6E,10E,14E,18E,22E,26E,30E,34E]-3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaene-1-ol	IIP0054	Yoshichika Yoshioka		C₅₀H₈₂O	699.185
55		Dolichol-18, a-Dihydrooctadecaprenol	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62E,66E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71-Octadecamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70-doheptacontaheptadecaen-1-ol	IIP0055	Yoshichika Yoshioka	Dol-18	C₉₀H₁₄₈O	1246.138		The biological role of dolichol (review)(Ref. 0043). Content of dolichol and activity of GlcNAc-1-P (UDP-N-acetylglucosamine:dolichyl phosphate N-acetylglucosamine 1-phosphate transferase) in fibroblasts from patients with carbohydrate- deficient- glycoprotein (CDG) syndrome were analyzed. The major defect of CDG syndrome is not found in the synthesys of dolichyl phosphate or GlcNAc-PP-Dol(Ref. 0061). Extraction of microsomes with n-heptane and subsequent reincorporation of dolichol were done in order to investigate the influence of dolichol on microsomal membrane functions. Dolichol affected microsomal membrane fluidity, but did not modify the activities of certain microsome membrane enzymes(Ref. 0062). Dolichol was covalently bound to cellular proteins with size of 5, 10, 27, 75, and >140 kDa(Ref. 0063). Dolichyl, dihydroheptaprenyl, and dihydrodecaprenyl phosphates induced apoptosis in U937 cells, while farnesyl phosphate, geranylgeranyl phosphate, dolichol, dolichal, and dlichoic acid did not induce apoptosis. Apoptosis induced by dihydroprenyl phosphate was mediated by caspase-3-like activation but not by caspase-1-like activation(Ref. 0065).									The arrangement of isoprene units in pig liver dolichol was determined by 1H- and 13C-NMR spectroscopy. 1H-NMR at 200MHz, 13C-NMR at 50.1MHz (with spectra)(Ref. 0045).			HPLC (with chromatograph)(Ref. 0046/0047/0048/0049/0050/0051). Separation of dolichol from dehydrodolichol by a simple two-plate thin-layer chromatography(Ref. 0052). Sequential microanalyses of free dolichol, dolichyl fatty acid ester and dolichyl phosphate in human serum were made fluorometrically by HPLC. The calibration curve of dolichol standard against the internal standard showed linearity at dolichol concentrations of 10ng to 500ng(Ref. 0053).	Human tissues (testes, adrenal ,liver, thyroid, pancreas, prostate, heart, kidney, spleen, lung)(Ref. 0054). Mouse testes(Ref. 0046). Rat and human tissues (heart, kidney, liver, lung, intestine, testis, brain, spleen, pituitary)(Ref. 0048). Distribution in rat liver subcellular organelles (outer mitochondrial and Golgi membranes, lysosomes and plasmamembranes contain considerable amount)(Ref. 0048). Contents in human tissues (adrenal, aorta, brain, colon, fatty tissue, heart, kidney, liver, lung, muscle, ovary, pancreas, pituitary gland, placenta, prostate, small intestine, spleen, testis, tyroid grand, uterus, and stomach)(Ref. 0055). Rat and human tissues (spleen, liver, kidney, myocardium, lung, pancreas, adrenal)(Ref. 0051). Levels of dolichol in neonatal and adult human tissues (thyroid, testis, liver, heart, kidney, lung, spleen)(Ref. 0056). Content in human serum(Ref. 0053). The effects of dietary proteins on the accumulation of dolichol in kidney, spleen, brain, and heart were studied. There were increases in dolichol contents in rat tissues with age. The contents of kidney and spleen were influenced by the diet(Ref. 0057). Dolichol content in different regions of the rat brain (cerebral cortex, striatum, hippocampus, cerebellum, and brain stem) were analyzed from birth to the age of 2 years. The level of dolichol increased almost 100-fold during the first 10 months of life and continued to increase thereafter(Ref. 0058). Content of dolichol and retinol in isolated rat non-parenchymal liver cells(Ref. 0106). Distribution of radiolabeled dolichol in rat liver fractions (nuclei, debris, mitochondria, lysosomes, microsomes, Golgi, cytosol)(Ref. 0060).		Incorporation of tritium from tritiated water into dolichol in the kidneys and liver of mice as a function of age(Ref. 0066). Age-associated changes in dolichol metabolism in the kidneys and liver of mice(Ref. 0066). Elevated dolichol synthesis in mouse testes during spermatogenesis(Ref. 0046). Synthesis in liver of normal and mutant mice(Ref. 0046). Presence of abnormal amounts of dolichols in the urinary sediment of Batten disease (neuronal ceroid lipofuscinosis) patients(Ref. 0047). Rat liver hyperplastic nodules(Ref. 0048). Human liver cirrosis and hepatocarcinoma(Ref. 0048). Brain dolichols in neuronal ceroid lipofuscinosis, epilepsy, Tay-Sachs desease, Juvenile Huntington disease, Alzheimer's disease, Pick disease, Astrocytoma(grade III-IV)(Ref. 0049). Content of cerebral cortex during aging (human & rat)(Ref. 0049). Composition of isolated pronase-treated cytosome fractions from neuronal ceroid-lipofuscinosis patients(Ref. 0049). The dolichol content of hyperplastic nodules in rat liver was four times that of normal. In developed hepatocarcinoma, the amount of dolichol was doubled(Ref. 0050). Effect of age on the content in brain, liver, spleen, kidney, and testis of the rat(Ref. 0067). Absorption and distribution of dolichol intubated into rats(Ref. 0091). Content in cerebral cortex of ceroid-lipofuscinosis(Ref. 0068). Age-related chnges of dolichyl phosphate content in rat and human tissues (Ref. 0051). Biosynthesis of dolichol from mevalonic acid was measured in non-malignant and malignant cultured human lymphocytes, freshly isolated human mononuclear leucocytes and in cultured human hepatoma cells(Ref. 0069). Formation of dolichol from dehydrodolichol is catalyzed by NADPH-dependent reductase localized in microsomes of rat liver. Dolichol was syntesized from isopentenyl diphosphate and Z,E,E-geranylgeranyl diphosphate. Neither dolichyl diphosphate nor dolichyl phosphate was detected(Ref. 0092). Farnesyl diphosphate is the common intermediate at the branch point for the synthesis of geranylgeranylated proteins as well as cholesterol, ubiquinone, dolichol, and farnesylated proteins(Ref. 0070). Dolichol contents of various organs of mice used as a model for Niemann-Pick's type C disease . Contents in subfractions isolated from the liver of mice used as a model for NPC (mitocondria, lysosomes, microsomes)(Ref. 0071).		The effects of TSH on dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells were investigated. TSH slightly increased the amount of dolichol and acitivated the oligosaccharyltransferase(Ref. 0072). Dehydrodolichol is a common branch point intermediate in the biosynthetic pathways leading to dolichal and dolichol(Ref. 0073). Metabolism of dolichol, dolichoic acid, and nordolichoic acid in MDCK and HepG2 cells were investigated. Dolichoic acid was broken down by alpha-oxidation and also converted to a mixture of polar compounds. No oxidative breakdown of dolichol was found(Ref. 0074). The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capasity were as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors(Ref. 0039). Age-dependent changes in hepatic dolichol content in rats fed either ad libitum, or subjected to restriction of daily food intake or every-other-day feeding ad libitum (antiaging dietary restriction). Both types of antiaging dietary restriction fully prevented the age-associated accumulation of dolichol in the liver and had a much smaller preventive effect in the kidney(Ref. 0075/0076). The effects of alcohol and glucagon on the biliary excretion of dolichols in rats were investigated. Chronic ethanol treatment decreased both biliary dolichol and beta-hexosaminidase excretion. The absolute amount of dolichol excreted into the bile correlated highly significantly with the absolute amount of biliary beta-hexosaminidase. Biliary dolichols are derived from hepatic lysosomes(Ref. 0077). Modifications in the concentration and distribution of rat liver microsomal dolichol and dolichyl phosphate after acute ethanol adiministration (6 g/kg body weight) were investigated. Between 3 and 24 hr after ethanol administration, the microsomal dolichyl phosphate concentration was significantly lower than in control rats. An earlier and more marked reduction of total dolichol was observed in the Golgi apparatus(Ref. 0059). Pro-oxidant agents lead to a significant decrease of both free dolichol and dolichyl phosphate in isolated rat hepatocytes(Ref. 0059). Distribution of radiolabeled dolichol in rat liver fractions(Ref. 0060).	[0039] / [0043] / [0045] / [0046] / [0047] / [0048] / [0049] / [0050] / [0051] / [0052] / [0053] / [0054] / [0055] / [0056] / [0057] / [0058] / [0059] / [0060] / [0061] / [0062] / [0063] / [0065] / [0066] / [0067] / [0068] / [0069] / [0070] / [0071] / [0072] / [0073] / [0074] / [0075] / [0076] / [0077] / [0091] / [0092] / [0106]
56		Dolichol-21, a-Dihydroheneicosaprenol	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66Z,70Z,74E,78E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79,83-Henicosamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78,82-tetraoctacontaeicosaen-1-ol	IIP0056	Yoshichika Yoshioka	Dol-21	C₁₀₅H₁₇₂O	1450.489		The biological role of dolichol (review)(Ref. 0043). Content of dolichol and activity of GlcNAc-1-P (UDP-N-acetylglucosamine:dolichyl phosphate N-acetylglucosamine 1-phosphate transferase) in fibroblasts from patients with carbohydrate-deficient-glycoprotein (CDG) syndrome were analyzed. The major defect of CDG syndrome is not found in the synthesys of dolichyl phosphate or GlcNAc-PP-Dol(Ref. 0061). Extraction of microsomes with n-heptane and subsequent reincorporation of dolichol were done in order to investigate the influence of dolichol on microsomal membrane functions. Dolichol affected microsomal membrane fluidity, but did not modify the activities of certain microsome membrane enzymes(Ref. 0062). Dolichol was covalently bound to cellular proteins with size of 5, 10, 27, 75, and >140 kDa(Ref. 0063). HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture. Geranylgeranylpyrophosphate and mevalonate completely reversed the effect of the inhibitors, while farnesylpyrophosphate partially reversed it and dolichol had no effect(Ref. 0064). Dolichyl, dihydroheptaprenyl, and dihydrodecaprenyl phosphates induced apoptosis in U937 cells, while farnesyl phosphate, geranylgeranyl phosphate, dolichol, dolichal, and dlichoic acid did not induce apoptosis. Apoptosis induced by dihydroprenyl phosphate was mediated by caspase-3-like activation but not by caspase-1-like activation(Ref. 0065).												HPLC (with chromatograph)(Ref. 0046/0047/0048/0049/0050/0051). Sequential microanalyses of free dolichol, dolichyl fatty acid ester and dolichyl phosphate in human serum were made fluorometrically by HPLC. The calibration curve of dolichol standard against the internal standard showed linearity at dolichol concentrations of 10ng to 500ng(Ref. 0053).	Human tissues (testes, adrenal, liver, thyroid, pancreas, prostate, heart, kidney, spleen, lung)(Ref. 0054). Mouse testes(Ref. 0046). Rat and human tissues (heart, kidney, liver, lung, intestine, testis, brain, spleen, pituitary)(Ref. 0048). Distribution in rat liver subcellular organelles (outer mitochondrial and Golgi membranes, lysosomes and plasmamembranes contain considerable amount)(Ref. 0048). Contents in human tissues (adrenal, aorta, brain, colon, fatty tissue, heart, kidney, liver, lung, muscle, ovary, pancreas, pituitary gland, placenta, prostate, small intestine, spleen, testis, tyroid grand, uterus, and stomach)(Ref. 0055). Rat and human tissues (spleen, liver, kidney, myocardium, lung, pancreas, adrenal)(Ref. 0051). Levels of dolichol in neonatal and adult human tissues (thyroid, testis, liver, heart, kidney, lung, spleen)(Ref. 0056). Content in human serum(Ref. 0053). The effects of dietary proteins on the accumulation of dolichol in kidney, spleen, brain, and heart were studied. There were increases in dolichol contents in rat tissues with age. The contents of kidney and spleen were influenced by the diet(Ref. 0057). Dolichol content in different regions of the rat brain (cerebral cortex, striatum, hippocampus, cerebellum, and brain stem) were analyzed from birth to the age of 2 years. The level of dolichol increased almost 100-fold during the first 10 months of life and continued to increase thereafter(Ref. 0058). Content of dolichol and retinol in isolated rat non-parenchymal liver cells(Ref. 0106).		Incorporation of tritium from tritiated water into dolichol in the kidneys and liver of mice as a function of age(Ref. 0066). Age-associated changes in dolichol metabolism in the kidneys and liver of mice(Ref. 0066). Elevated dolichol synthesis in mouse testes during spermatogenesis(Ref. 0046). Synthesis in livers of normal and mutant mice(Ref. 0046). Presence of abnormal amounts of dolichols in the urinary sediment of Batten disease (neuronal ceroid lipofuscinosis) patients(Ref. 0047). Rat liver hyperplastic nodules(Ref. 0048). Human liver cirrosis and hepatocarcinoma(Ref. 0048). Brain dolichols in neuronal ceroid lipofuscinosis, epilepsy, Tay-Sachs desease, Juvenile Huntington disease, Alzheimer's disease, Pick disease, Astrocytoma(grade III-IV)(Ref. 0049). Content of cerebral cortex during aging (human & rat)(Ref. 0049). Composition of isolated pronase-treated cytosome fractions from neuronal ceroid-lipofuscinosis patients(Ref. 0049). The content in hyperplastic nodules of rat liver increased four times in the homoginate and six times in the microsomes. In developed hepatocarcinoma, the amount was doubled(Ref. 0050). Effect of age on the content in brain, liver, spleen, kidney, and testis of the rat(Ref. 0067). Content in cerebral cortex of ceroid-lipofuscinosis(Ref. 0068). Age-related chnges of dolichyl phosphate content in rat and human tissues (Ref. 0051). Biosynthesis of dolichol from mevalonic acid was measured in non-malignant and malignant cultured human lymphocytes, freshly isolated human mononuclear leucocytes and in cultured human hepatoma cells(Ref. 0069). Dolichol contents of various organs of mice used as a model for Niemann-Pick's type C disease . Contents in subfractions isolated from the liver of mice used as a model for NPC (Ref. 0071). The effects of TSH on dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells were investigated. TSH slightly increased the amount of dolichol and acitivated the oligosaccharyltransferase(Ref. 0072). Age-dependent changes in hepatic dolichol content in rats fed either ad libitum, or subjected to restriction of daily food intake or every-other-day feeding ad libitum (antiaging dietary restriction). Both types of antiaging dietary restriction fully prevented the age-associated accumulation of dolichol in the liver and had a much smaller preventive effect in the kidney(Ref. 0075/0076).		The effects of alchol and glucagon on the biliary excretion of dolichols in rats were investigated. Chronic ethanol treatment decreased both biliary dolichol and beta-hexosaminidase excretion. The absolute amount of dolichol excreted into the bile correlated highly significantly with the absolute amount of biliary beta-hexosaminidase. Biliary dolichols are derived from hepatic lysosomes(Ref. 0077). Modifications in the concentration and distribution of rat liver microsomal dolichol and dolichyl phosphate after acute ethanol adiministration (6 g/kg body weight) were investigated. Between 3 and 24 hr after ethanol administration, the microsomal dolichyl phosphate concentration was significantly lower than in control rats. An earlier and more marked reduction of total dolichol was observed in the Golgi apparatus(Ref. 0059). Pro-oxidant agents lead to a significant decrease of both free dolichol and dolichyl phosphate in isolated rat hepatocytes(Ref. 0059).	[0043] / [0046] / [0047] / [0048] / [0049] / [0050] / [0051] / [0053] / [0054] / [0055] / [0056] / [0057] / [0058] / [0059] / [0061] / [0062] / [0063] / [0064] / [0065] / [0066] / [0067] / [0068] / [0069] / [0071] / [0072] / [0075] / [0076] / [0077] / [0106]
57		Dolichol-22, a-Dihydrodocosaprenol	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66Z,70Z,74Z,78E,82E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79,83,87-Docosamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78,82,86-octaoctacontahenicosaen-1-ol	IIP0057	Yoshichika Yoshioka	Dol-22	C₁₁₀H₁₈₀O	1518.606		The biological role of dolichol (review)(Ref. 0043). Extraction of microsomes with n-heptane and subsequent reincorporation of dolichol were done in order to investigate the influence of dolichol on microsomal membrane functions. Dolichol affected microsomal membrane fluidity, but did not modify the activities of certain microsome membrane enzymes(Ref. 0062). HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture. Geranylgeranylpyrophosphate and mevalonate completely reversed the effect of the inhibitors, while farnesylpyrophosphate partially reversed it and dolichol had no effect(Ref. 0064).												HPLC (with chromatograph)(Ref. 0048/0051).	Human tissues (testes, adrenal, liver, thyroid, pancreas, prostate, heart, kidney, spleen, lung)(Ref. 0054). Human tissues (liver, testis, spleen, pituitary)(Ref. 0048). Rat and human tissues (spleen, liver, kidney, myocardium, lung, pancreas, adrenal)(Ref. 0051). The effects of dietary proteins on the accumulation of dolichol in kidney, spleen, brain, and heart were studied. There were increases in dolichol contents in rat tissues with age. The contents of kidney and spleen were influenced by the diet(Ref. 0057). Dolichol content in different regions of the rat brain (cerebral cortex, striatum, hippocampus, cerebellum, and brain stem) were analyzed from birth to the age of 2 years. The level of dolichol increased almost 100-fold during the first 10 months of life and continued to increase thereafter(Ref. 0058).		Rat liver hyperplastic nodules(Ref. 0048). Human liver cirrosis and hepatocarcinoma (Ref. 0048). Age-related chnges of dolichyl phosphate content in rat and human tissues (spleen, liver, kidney, heart, lung, pancreas, adrenal)(Ref. 0051). Dolichol contents of various organs of mice used as a model for Niemann-Pick's type C disease (liver, spleen, kidney, brain, testis, lung, adipose tissue, heart, intestine, skeletal muscle). Contents in subfractions isolated from the liver of mice used as a model for NPC (mitocondria, lysosomes, microsomes)(Ref. 0071).			[0043] / [0048] / [0051] / [0054] / [0057] / [0058] / [0062] / [0064] / [0071]
58		Dolichol-23, a-Dihydrotricosaprenol	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66Z,70Z,74Z,78Z,82E,86E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79,83,87,91-Tricosamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78,82,86,90-dononacontadocosaen-1-ol	IIP0058	Yoshichika Yoshioka	Dol-23	C₁₁₅H₁₈₈O	1586.723		The biological role of dolichol (review)(Ref. 0043). HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture. Geranylgeranylpyrophosphate and mevalonate completely reversed the effect of the inhibitors, while farnesylpyrophosphate partially reversed it and dolichol had no effect(Ref. 0064).									1H-NMR spectrum at 100MHz (with spectrum)(Ref. 0048).				Bovine pituitary glands(Ref. 0048).					[0043] / [0048] / [0064]
59		Dolichol-24, a-Dihydrotetracosaprenol	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66Z,70Z,74Z,78Z,82Z,86E,90E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79,83,87,91,95-Tetracosamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78,82,86,90,94-hexanonacontatricosaen-1-ol	IIP0059	Yoshichika Yoshioka	Dol-24	C₁₂₀H₁₉₆O	1654.840		HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture. Geranylgeranylpyrophosphate and mevalonate completely reversed the effect of the inhibitors, while farnesylpyrophosphate partially reversed it and dolichol had no effect(Ref. 0064).																	The effect of dolichols, polyprenols, dolichol esterified with fatty acids, and dolichyl phosphate on the structure and fluidity of model membranes was studied using 31P NMR, small-angle x-ray scattering, differential scanning calorimetry, and freeze-fracture electron microscopy. Dolichol and dolichol derivatives destabilize unsaturated phosphatidylethanolamine containing bilayer structures and promote hexagonal II phase formation. Dolichol and dolichyl-P increase the fatty acid fluidity in phosphatidylethanolamine mixtures(Ref. 0044).	[0044] / [0064]
60		Geranyl monophosphate	[2E]-3,7-Dimethyl-2,6-octadien-1-yl monophosphate	IIP0060	Yoshichika Yoshioka	GOP	C₁₀H₁₉O₄P	234.229		Metabolic labeling of rat liver slices with mevalonic acid revealed the accumulation of E,E,E-geranylgeranyl (di)phosphate as well as dolichyl (di)phosphate (C85 and C90) and dehydrodolichol (C85 and C90), but no accumulation of Z,E,E-geranylgeranyl (di)phosphate or E,E-farnesyl (di)phosphate was detected(Ref. 0026).																		[0026]
61		Farnesyl monophosphate	[2E,6E]-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl monophosphate	IIP0061	Yoshichika Yoshioka	FOP	C₁₅H₂₇O₄P	302.346		Metabolic labeling of rat liver slices with mevalonic acid revealed the accumulation of E,E,E-geranylgeranyl (di)phosphate as well as dolichyl (di)phosphate (C85 and C90) and dehydrodolichol (C85 and C90), but no accumulation of Z,E,E-geranylgeranyl (di)phosphate or E,E-farnesyl (di)phosphate was detected(Ref. 0026). Dolichyl, dihydroheptaprenyl, and dihydrodecaprenyl phosphates induced apoptosis in U937 cells, while farnesyl phosphate, geranylgeranyl phosphate, dolichol, dolichal, and dlichoic acid did not induce apoptosis. Apoptosis induced by dihydroprenyl phosphate was mediated by caspase-3-like activation but not by caspase-1-like activation(Ref. 0065).																		[0026] / [0065]
62		Geranylgeranyl monophosphate	[2E,6E,10E]-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-yl monophosphate	IIP0062	Yoshichika Yoshioka	GGOP	C₂₀H₃₅O₄P	370.463		Dolichyl, dihydroheptaprenyl, and dihydrodecaprenyl phosphates induced apoptosis in U937 cells, while farnesyl phosphate, geranylgeranyl phosphate, dolichol, dolichal, and dlichoic acid did not induce apoptosis. Apoptosis induced by dihydroprenyl phosphate was mediated by caspase-3-like activation but not by caspase-1-like activation(Ref. 0065).																		[0065]
63		Prenyl-11 monophosphate, Undecaprenyl monophosphate	[6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E]-3,7,11,15,19,23,27,31,35,39,43-Undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaen-1-yl monophosphate	IIP0063	Yoshichika Yoshioka		C₅₅H₉₁O₄P	847.282											The head and tail sites of undecaprenol exibit a fast motion as exibited in the short chain isoprenols. Undecaprenol appears to induce a non-bilayer (isotropic) organization of phospholipid molecules in PE/PC (2:1) vesicles(Ref. 0085).									[0085]
64		Dihydroprenyl-7 monophosphate, a-Dihydroheptaprenyl monophosphate	[6E,10E,14E,18E,22E]-3,7,11,15,19,23,27-Heptamethyl-6,10,14,18,22,26-octacosahexaen-1-yl monophosphate	IIP0064	Yoshichika Yoshioka		C₃₅H₆₁O₄P	576.830		Dolichyl, dihydroheptaprenyl, and dihydrodecaprenyl phosphates induced apoptosis in U937 cells, while farnesyl phosphate, geranylgeranyl phosphate, dolichol, dolichal, and dlichoic acid did not induce apoptosis. Apoptosis induced by dihydroprenyl phosphate was mediated by caspase-3-like activation but not by caspase-1-like activation(Ref. 0065).																		[0065]
65		Dihydroprenyl-10 monophosphate, a-Dihydrodecaprenyl monophosphate	[6E,10E,14E,18E,22E,26E,30E,34E]-3,7,11,15,19,23,27,31,35,39-Decamethyl-6,10,14,18,22,26,30,34,38-Tetracontanonaen-1-yl monophosphate	IIP0065	Yoshichika Yoshioka		C₅₀H₈₅O₄P	781.181		Dolichyl, dihydroheptaprenyl, and dihydrodecaprenyl phosphates induced apoptosis in U937 cells, while farnesyl phosphate, geranylgeranyl phosphate, dolichol, dolichal, and dolichoic acid did not induce apoptosis. Apoptosis induced by dihydroprenyl phosphate was mediated by caspase-3-like activation but not by caspase-1-like activation(Ref. 0065).																	The dynamics of dolichyl phosphate molecules in membranes can be regulated by transmembrane electrical potential(Ref. 0093).	[0065] / [0093]
66		Dolichyl-12 monophosphate, a-Dihydrododecaprenyl monophosphate	3,7,11,15,19,23,27,31,35,39,43,47-Dodecamethyl-6,10,14,18,22,26,30,34,38,42,46-octatetracontaundecaen-1-yl monophosphate	IIP0066	Yoshichika Yoshioka	Dol-12-P	C₆₀H₁₀₁O₄P	917.415																			The dynamics of dolichyl phosphate molecules in membranes can be regulated by transmembrane electrical potential(Ref. 0093).	[0093]
67		Dolichyl-17 monophosphate, a-Dihydroheptadecaprenyl monophosphate	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58E,62E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67-Heptadecamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66-octahexacontahexadecaen-1-yl monophosphate	IIP0067	Yoshichika Yoshioka	Dol-17-P	C₈₅H₁₄₁O₄P	1258.000		Role of Dol-P in regulation of protein glycosylation in 2- acetylaminofluorene- induced carcinogenesis in rat liver(Ref. 0050). Effect of Dol-P concentration on the formation of lipid-saccharides and the N-glycosylation of protein by thyroid ER vesicles(Ref. 0095). The microsomal fraction of liver has been found to catalyze glucose transfer from UDPG to a lipid acceptor to be identical to the compound obtained by chemical phosphorylation of Dol (Ref. 0096). The biological role of Dol (review) (Ref. 0043). Metabolic labeling of rat liver slices with mevalonic acid revealed the accumulation of E,E,E-geranylgeranyl (di)phosphate as well as dolichyl (di)phosphate (C85 and C90) and dehydrodolichol (C85 and C90), but no accumulation of Z,E,E-geranylgeranyl (di)phosphate or E,E-farnesyl (di)phosphate was detected(Ref. 0026). Dol-P pathway leading to N-glycosylation of protein(Ref. 0097). Content of dolichol and activity of GlcNAc-1-P (UDP-N-acetylglucosamine:dolichyl phosphate N-acetylglucosamine 1-phosphate transferase) in fibroblasts from patients with carbohydrate- deficient- glycoprotein (CDG) syndrome were analyzed. The major defect of CDG syndrome is not found in the synthesys of Dol-P or GlcNAc-PP-Dol(Ref. 0061). Dolichyl phosphate is a potent inducer of apoptosis in rat glioma cells. Apoptotic changes were also observed in HL-60 cells, SIRC cells and HeLa cells(Ref. 0098). Exogenous dolichyl phosphate induced apoptosis in the human monoblastic leukemia cell line U937 within 4 hours. Dol-P-induced apoptosis is mediated by mitogen-activated protein kinase (MAP kinase) cascade(Ref. 0099). Treatment of U937 cells with dolichyl phosphate led to an increase in the activity of the ICE family protease CPP32, accompanied with cleavage of pre-CPP32 to generate p17. The modulation of cAMP synthesis due to the stimulation of adenylate cyclase by dolichyl phosphate plays a critical role in CPP32 activation and apoptosis(Ref. 0100). Dolichyl, dihydroheptaprenyl, and dihydrodecaprenyl phosphates induced apoptosis in U937 cells, while farnesyl phosphate, geranylgeranyl phosphate, dolichol, dolichal, and dolichoic acid did not induce apoptosis. Apoptosis induced by dihydroprenyl phosphate was mediated by caspase-3-like activation but not by caspase-1-like activation(Ref. 0065).												HPLC (with chromatograph)(Ref. 0094/0048/0051). Sequential microanalyses of free dolichol, dolichyl fatty acid ester and dolichyl phosphate in human serum were made fluorometrically by HPLC. The calibration curve of dolichol standard against the internal standard showed linearity at dolichol concentrations of 10ng to 500ng(Ref. 0053).	Direct estimation of dolichyl phosphate in rat liver by high pressure liquid chromatography(Ref. 0094). Human liver and testis(Ref. 0048). Rat liver(Ref. 0048). Contents in human tissues (adrenal, aorta, colon, heart, kidney, liver, lung, muscle, pancreas, pituitary gland, prostate, small intestine, spleen, testis, tyroid grand, and stomach)(Ref. 0055). Rat and human tissues (spleen, liver, kidney, myocardium, lung, pancreas, adrenal)(Ref. 0051). Levels of dolichyl phosphate in neonatal and adult human tissues (liver, heart, kidney, lung, spleen)(Ref. 0056). Content in human serum(Ref. 0053). Distribution of radiolabeled dolichol-P in rat liver fractions (nuclei, debris, mitochondria, lysosomes, microsomes, Golgi, cytosol)(Ref. 0060).		Incorporation of tritium from tritiated water into dol-P in the kidneys and liver of mice as a function of age(Ref. 0066). Age-associated changes in dol-P metabolism in the kidneys and liver of mice(Ref. 0066). Rat liver hyperplastic nodules(Ref. 0048). Human liver cirrosis and hepatocarcinoma(Ref. 0048). The amount was greatly decreased in hyperplastic nodules of rat liver(Ref. 0050). Effect of age on the content in brain, liver, spleen, kidney, and testis of the rat(Ref. 0067). Age-related chnges of dolichyl phosphate content in rat and human tissues (Ref. 0051). The uptake of F-PP and GG-PP was studied using primary cultures of chromaffin cells. Dolichylmonophosphate and isopentenylpyrophosphate promoted the uptake(Ref. 0079). Contents of various organs of mice used as a model for Niemann-Pick's type C disease . Contents in subfractions isolated from the liver of mice used as a model for NPC (Ref. 0071). The effects of TSH on dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells were investigated. TSH slightly increased the amount of dolichol-P and acitivated the oligosaccharyltransferase(Ref. 0072). The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capasity were as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors(Ref. 0039). Modifications in the concentration and distribution of rat liver microsomal dolichol and dolichyl phosphate after acute ethanol adiministration (6 g/kg body weight) were investigated. Between 3 and 24 hr after ethanol administration, the microsomal dolichyl phosphate concentration was significantly lower than in control rats. An earlier and more marked reduction of total dolichol was observed in the Golgi apparatus(Ref. 0059). Pro-oxidant agents lead to a significant decrease of both free dolichol and dolichyl phosphate in isolated rat hepatocytes(Ref. 0059). Distribution of radiolabeled dolichol-P in rat liver fractions(Ref. 0060). The presence of covalently bound dolichyl phosphate in rat liver(Ref. 0060).		Monoclonal antibody to amphomycin is a tool to study the topography of dolichol monophosphate in the membrane(Ref. 0101).	[0026] / [0039] / [0043] / [0048] / [0050] / [0051] / [0053] / [0055] / [0056] / [0059] / [0060] / [0061] / [0065] / [0066] / [0067] / [0071] / [0072] / [0079] / [0094] / [0095] / [0096] / [0097] / [0098] / [0099] / [0100] / [0101]
68		Dolichyl-18 monophosphate, a-Dihydrooctadecaprenyl monophosphate	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62E,66E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71-Octadecamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70-doheptacontaheptadecaen-1-yl monophosphate	IIP0068	Yoshichika Yoshioka	Dol-18-P	C₉₀H₁₄₉O₄P	1326.117		Role of Dol-P in regulation of protein glycosylation in 2-acetylaminofluorene-induced carcinogenesis in rat liver(Ref. 0050). Effect of Dol-P concentration on the formation of lipid-saccharides and the N-glycosylation of protein by thyroid ER vesicles(Ref. 0095). The microsomal fraction of liver has been found to catalyze glucose transfer from UDPG to a lipid acceptor to be identical to the compound obtained by chemical phosphorylation of Dol (Ref. 0096). The biological role of dolichol (review) (Ref. 0043). Metabolic labeling of rat liver slices with mevalonic acid revealed the accumulation of E,E,E-geranylgeranyl (di)phosphate as well as dolichyl (di)phosphate (C85 and C90) and dehydrodolichol (C85 and C90), but no accumulation of Z,E,E-geranylgeranyl (di)phosphate or E,E-farnesyl (di)phosphate was detected(Ref. 0026). Dol-P pathway leading to N-glycosylation of protein(Ref. 0097). Content of Dol and activity of GlcNAc-1-P (UDP-N-acetylglucosamine: Dol-P N-acetylglucosamine 1-phosphate transferase) in fibroblasts from patients with carbohydrate-deficient-glycoprotein (CDG) syndrome were analyzed. The major defect of CDG syndrome is not found in the synthesys of Dol-P or GlcNAc-PP-Dol (Ref. 0061). Dolichyl phosphate is a potent inducer of apoptosis in rat glioma cells. Apoptotic changes were also observed in HL-60 cells, SIRC cells and HeLa cells(Ref. 0098). Exogenous dolichyl phosphate induced apoptosis in the human monoblastic leukemia cell line U937 within 4 hours. Dol-P-induced apoptosis is mediated by mitogen-activated protein kinase (MAP kinase) cascade(Ref. 0099). Treatment of U937 cells with dolichyl phosphate led to an increase in the activity of the ICE family protease CPP32, accompanied with cleavage of pre-CPP32 to generate p17. The modulation od cAMP synthesis due to the stimulation of adenylate cyclase by dolichyl phosphate plays a critical role in CPP32 activation and apoptosis(Ref. 0100). Dolichyl, dihydroheptaprenyl, and dihydrodecaprenyl phosphates induced apoptosis in U937 cells, while farnesyl phosphate, geranylgeranyl phosphate, dolichol, dolichal, and dolichoic acid did not induce apoptosis. Apoptosis induced by dihydroprenyl phosphate was mediated by caspase-3-like activation but not by caspase-1-like activation(Ref. 0065).												HPLC (with chromatograph)(Ref. 0094/0048/0051). Sequential microanalyses of free dolichol, dolichyl fatty acid ester and dolichyl phosphate in human serum were made fluorometrically by HPLC. The calibration curve of dolichol standard against the internal standard showed linearity at dolichol concentrations of 10ng to 500ng(Ref. 0053).	Direct estimation of dolichyl phosphate in rat liver by high pressure liquid chromatography(Ref. 0094). Human liver and testis(Ref. 0048). Rat liver(Ref. 0048). Contents in human tissues (adrenal, aorta, colon, heart, kidney, liver, lung, muscle, pancreas, pituitary gland, prostate, small intestine, spleen, testis, tyroid grand, and stomach)(Ref. 0055). Rat and human tissues (spleen, liver, kidney, myocardium, lung, pancreas, adrenal)(Ref. 0051). Levels of dolichyl phosphate in neonatal and adult human tissues (liver, heart, kidney, lung, spleen)(Ref. 0056). Content in human serum(Ref. 0053). Distribution of radiolabeled dolichol-P in rat liver fractions (nuclei, debris, mitochondria, lysosomes, microsomes, Golgi, cytosol)(Ref. 0060).		Incorporation of tritium from tritiated water into Dol-P in the kidneys and liver of mice as a function of age(Ref. 0066). Age-associated changes in Dol-P metabolism in the kidneys and liver of mice(Ref. 0066). Rat liver hyperplastic nodules(Ref. 0048). Human liver cirrosis and hepatocarcinoma(Ref. 0048). The amount was greatly decreased in hyperplastic nodules of rat liver(Ref. 0050). Effect of age on the content in brain, liver, spleen, kidney, and testis of the rat(Ref. 0067). Age-related chnges of Dol-P content in rat and human tissues (Ref. 0051). The uptake of F-PP and GG-PP was studied using primary cultures of chromaffin cells. Dolichylmonophosphate and isopentenylpyrophosphate promoted the uptake(Ref. 0079). Contents of various organs of mice used as a model for Niemann-Pick's type C disease. Contents in subfractions isolated from the liver of mice used as a model for NPC (Ref. 0071). The effects of TSH on dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells were investigated. TSH slightly increased the amount of Dol-P and acitivated the oligosaccharyltransferase(Ref. 0072). The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capasity were as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors(Ref. 0039). Modifications in the concentration and distribution of rat liver microsomal dolichol and dolichyl phosphate after acute ethanol adiministration (6 g/kg body weight) were investigated. Between 3 and 24 hr after ethanol administration, the microsomal dolichyl phosphate concentration was significantly lower than in control rats. An earlier and more marked reduction of total dolichol was observed in the Golgi apparatus(Ref. 0059). Pro-oxidant agents lead to a significant decrease of both free Dol and Dol-P in isolated rat hepatocytes(Ref. 0059). Distribution of radiolabeled Dol-P in rat liver fractions(Ref. 0060). The presence of covalently bound Dol-P in rat liver(Ref. 0060).		Monoclonal antibody to amphomycin is a tool to study the topography of dolichol monophosphate in the membrane(Ref. 0101).	[0026] / [0039] / [0043] / [0048] / [0050] / [0051] / [0053] / [0055] / [0056] / [0059] / [0060] / [0061] / [0065] / [0066] / [0067] / [0071] / [0072] / [0079] / [0094] / [0095] / [0096] / [0097] / [0098] / [0099] / [0100] / [0101]
69		Dolichyl-19 monophosphate, a-Dihydrononadecaprenyl monophosphate	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66E,70E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75-Nonadecamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74-hexaheptacontaoctadecaen-1-yl monophosphate	IIP0069	Yoshichika Yoshioka	Dol-19-P	C₉₅H₁₅₇O₄P	1394.234		Role of dolichyl phosphate in regulation of protein glycosylation in 2-acetylaminofluorene- induced carcinogenesis in rat liver(Ref. 0050). Effect of Dol-P concentration on the formation of lipid-saccharides and the N-glycosylation of protein by thyroid ER vesicles (Ref. 0095). The microsomal fraction of liver has been found to catalyze glucose transfer from UDPG to a lipid acceptor to be identical to the compound obtained by chemical phosphorylation of Dol (Ref. 0096). The biological role of Dol (review) (Ref. 0043). Dol-P pathway leading to N-glycosylation of protein(Ref. 0097). Content of Dol and activity of GlcNAc-1-P (UDP-N-acetylglucosamine:Dol-P N-acetylglucosamine 1-phosphate transferase) in fibroblasts from patients with carbohydrate-deficient-glycoprotein (CDG) syndrome were analyzed. The major defect of CDG syndrome is not found in the synthesys of Dol-P or GlcNAc-PP-Dol (Ref. 0061). Dol-P is a potent inducer of apoptosis in rat glioma cells. Apoptotic changes were also observed in HL-60 cells, SIRC cells and HeLa cells (Ref. 0098). Exogenous dolichyl phosphate induced apoptosis in the human monoblastic leukemia cell line U937 within 4 hours. Dol-P-induced apoptosis is mediated by mitogen-activated protein kinase (MAP kinase) cascade(Ref. 0099). Treatment of U937 cells with dolichyl phosphate led to an increase in the activity of the ICE family protease CPP32, accompanied with cleavage of pre-CPP32 to generate p17. The modulation od cAMP synthesis due to the stimulation of adenylate cyclase by dolichyl phosphate plays a critical role in CPP32 activation and apoptosis(Ref. 0100). Dolichyl, dihydroheptaprenyl, and dihydrodecaprenyl phosphates induced apoptosis in U937 cells, while farnesyl phosphate, geranylgeranyl phosphate, dolichol, dolichal, and dolichoic acid did not induce apoptosis. Apoptosis induced by dihydroprenyl phosphate was mediated by caspase-3-like activation but not by caspase-1-like activation(Ref. 0065).									The head and tail sites of dolichol exibit a fast motion as exibited in the short chain isoprenols. Dolichol appears to induce a non-bilayer (isotropic) organization of phospholipid molecules in PE/PC (2:1) vesicles.(Ref. 0085)			HPLC (with chromatograph)(Ref. 0094/0048/0051). Sequential microanalyses of free dolichol, dolichyl fatty acid ester and dolichyl phosphate in human serum were made fluorometrically by HPLC. The calibration curve of dolichol standard against the internal standard showed linearity at dolichol concentrations of 10ng to 500ng(Ref. 0053).	Direct estimation of dolichyl phosphate in rat liver by high pressure liquid chromatography(Ref. 0094). Human liver and testis(Ref. 0048). Rat liver(Ref. 0048). Contents in human tissues (adrenal, aorta, colon, heart, kidney, liver, lung, muscle, pancreas, pituitary gland, prostate, small intestine, spleen, testis, tyroid grand, and stomach)(Ref. 0055). Rat and human tissues (spleen, liver, kidney, myocardium, lung, pancreas, adrenal)(Ref. 0051). Levels of dolichyl phosphate in neonatal and adult human tissues (liver, heart, kidney, lung, spleen)(Ref. 0056). Content in human serum(Ref. 0053). Distribution of radiolabeled dolichol-P in rat liver fractions (nuclei, debris, mitochondria, lysosomes, microsomes, Golgi, cytosol)(Ref. 0060).		Incorporation of tritium from tritiated water into Dol-P in the kidneys and liver of mice as a function of age(Ref. 0066). Age-associated changes in Dol-P metabolism in the kidneys and liver of mice(Ref. 0066). Rat liver hyperplastic nodules(Ref. 0048). Human liver cirrosis and hepatocarcinoma(Ref. 0048). The amount was greatly decreased in hyperplastic nodules of rat liver(Ref. 0050). Effect of age on the content in brain, liver, spleen, kidney, and testis of the rat(Ref. 0067). Age-related chnges of Dol-P content in rat and human tissues (Ref. 0051). The uptake of F-PP and GG-PP was studied using primary cultures of chromaffin cells. Dol-P and isopentenylpyrophosphate promoted the uptake(Ref. 0079). Contents of various organs of mice used as a model for Niemann-Pick's type C disease (liver, spleen, kidney, brain, testis, lung, adipose tissue, heart, intestine, skeletal muscle). Contents in subfractions isolated from the liver of mice used as a model for NPC (mitocondria, lysosomes, microsomes) (Ref. 0071). The effects of TSH on Dol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells were investigated. TSH slightly increased the amount of Dol-P and acitivated the oligosaccharyltransferase (Ref. 0072). The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capasity were as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and Dol were not inhibitors(Ref. 0039). Modifications in the concentration and distribution of rat liver microsomal Dol and Dol-Pafter acute ethanol adiministration (6 g/kg body weight) were investigated. Between 3 and 24 hr after ethanol administration, the microsomal Dol-P concentration was significantly lower than in control rats. An earlier and more marked reduction of total Dol was observed in the Golgi apparatus(Ref. 0059). Pro-oxidant agents lead to a significant decrease of both freeDol and Dol-P in isolated rat hepatocytes(Ref. 0059). Distribution of radiolabeled Dol-P in rat liver fractions(Ref. 0060). The presence of covalently bound Dol-P in rat liver(Ref. 0060).		Monoclonal antibody to amphomycin is a tool to study the topography of dolichol monophosphate in the membrane(Ref. 0101).	[0039] / [0043] / [0048] / [0050] / [0051] / [0053] / [0055] / [0056] / [0059] / [0060] / [0061] / [0065] / [0066] / [0067] / [0071] / [0072] / [0079] / [0085] / [0094] / [0095] / [0096] / [0097] / [0098] / [0099] / [0100] / [0101]
70		Dolichyl-20 monophosphate, a-Dihydroeicosaprenyl monophosphate	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66Z,70E,74E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79-Eicosamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78-octacontanonadecaen-1-yl monophosphate	IIP0070	Yoshichika Yoshioka	Dol-20-P	C₁₀₀H₁₆₅O₄P	1462.351		Role of Dol-P in regulation of protein glycosylation in 2-acetylaminofluorene-induced carcinogenesis in rat liver(Ref. 0050). Effect of Dol-P concentration on the formation of lipid-saccharides and the N-glycosylation of protein by thyroid ER vesicles(Ref. 0095). The microsomal fraction of liver has been found to catalyze glucose transfer from UDPG to a lipid acceptor to be identical to the compound obtained by chemical phosphorylation of Dol (Ref. 0096). The biological role of Dol (review) (Ref. 0043). Dol-P pathway leading to N-glycosylation of protein(Ref. 0097). Content of Dol and activity of GlcNAc-1-P (UDP-N-acetylglucosamine:Dol-P N-acetylglucosamine 1-phosphate transferase) in fibroblasts from patients with carbohydrate-deficient-glycoprotein (CDG) syndrome were analyzed. The major defect of CDG syndrome is not found in the synthesys of Dol-P or GlcNAc-PP-Dol(Ref. 0061). Dol-P is a potent inducer of apoptosis in rat glioma cells. Apoptotic changes were also observed in HL-60 cells, SIRC cells and HeLa cells(Ref. 0098). Exogenous Dol-P induced apoptosis in the human monoblastic leukemia cell line U937 within 4 hours. Dol-P-induced apoptosis is mediated by mitogen-activated protein kinase (MAP kinase) cascade(Ref. 0099). Treatment of U937 cells with Dol-P led to an increase in the activity of the ICE family protease CPP32, accompanied with cleavage of pre-CPP32 to generate p17. The modulation od cAMP synthesis due to the stimulation of adenylate cyclase by Dol-P plays a critical role in CPP32 activation and apoptosis(Ref. 0100). Dolichyl, dihydroheptaprenyl, and dihydrodecaprenyl phosphates induced apoptosis in U937 cells, while farnesyl phosphate, geranylgeranyl phosphate, dolichol, dolichal, and dolichoic acid did not induce apoptosis. Apoptosis induced by dihydroprenyl phosphate was mediated by caspase-3-like activation but not by caspase-1-like activation(Ref. 0065).												HPLC (with chromatograph)(Ref. 0094/0048/0051). Sequential microanalyses of free dolichol, dolichyl fatty acid ester and dolichyl phosphate in human serum were made fluorometrically by HPLC. The calibration curve of dolichol standard against the internal standard showed linearity at dolichol concentrations of 10ng to 500ng(Ref. 0053).	Direct estimation of dolichyl phosphate in rat liver by high pressure liquid chromatography(Ref. 0094). Human liver and testis(Ref. 0048). Rat liver(Ref. 0048). Contents in human tissues (adrenal, aorta, colon, heart, kidney, liver, lung, muscle, pancreas, pituitary gland, prostate, small intestine, spleen, testis, tyroid grand, and stomach)(Ref. 0055). Rat and human tissues (spleen, liver, kidney, myocardium, lung, pancreas, adrenal)(Ref. 0051). Levels of dolichyl phosphate in neonatal and adult human tissues (liver, heart, kidney, lung, spleen)(Ref. 0056). Content in human serum(Ref. 0053). Distribution of radiolabeled dolichol-P in rat liver fractions (nuclei, debris, mitochondria, lysosomes, microsomes, Golgi, cytosol)(Ref. 0060).	Phosphorylation of dolichol-20.	Incorporation of tritium from tritiated water into Dol-P in the kidneys and liver of mice as a function of age(Ref. 0066). Age-associated changes in Dol-P metabolism in the kidneys and liver of mice(Ref. 0066). Rat liver hyperplastic nodules(Ref. 0048). Human liver cirrosis and hepatocarcinoma(Ref. 0048). The amount was greatly decreased in hyperplastic nodules of rat liver(Ref. 0050). Effect of age on the content in brain, liver, spleen, kidney, and testis of the rat(Ref. 0067). Age-related chnges of Dol-P content in rat and human tissues (spleen, liver, kidney, heart, lung, pancreas, adrenal)(Ref. 0051). The uptake of F-PP and GG-PP was studied using primary cultures of chromaffin cells. Dolichylmonophosphate and isopentenylpyrophosphate promoted the uptake(Ref. 0079). Contents of various organs of mice used as a model for Niemann-Pick's type C disease (liver, spleen, kidney, brain, testis, lung, adipose tissue, heart, intestine, skeletal muscle). Contents in subfractions isolated from the liver of mice used as a model for NPC (mitocondria, lysosomes, microsomes)(Ref. 0071). The effects of TSH on dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells were investigated. TSH slightly increased the amount of Dol-P and acitivated the oligosaccharyltransferase (Ref. 0072). The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capasity were as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and Dol were not inhibitors(Ref. 0039). Modifications in the concentration and distribution of rat liver microsomal Dol and Dol-P after acute ethanol adiministration (6 g/kg body weight) were investigated. Between 3 and 24 hr after ethanol administration, the microsomal Dol-P concentration was significantly lower than in control rats. An earlier and more marked reduction of total Dol was observed in the Golgi apparatus(Ref. 0059). Pro-oxidant agents lead to a significant decrease of both free Dol and Dol-P in isolated rat hepatocytes(Ref. 0059). Distribution of radiolabeled Dol-P in rat liver fractions(Ref. 0060). The presence of covalently bound Dol-P in rat liver(Ref. 0060).		The effect of dolichols, polyprenols, dolichol esterified with fatty acids, and dolichyl phosphate on the structure and fluidity of model membranes was studied using 31P NMR, small-angle x-ray scattering, differential scanning calorimetry, and freeze-fracture electron microscopy. Dolichol and dolichol derivatives destabilize unsaturated phosphatidylethanolamine containing bilayer structures and promote hexagonal II phase formation. Dolichol and dolichyl-P increase the fatty acid fluidity in phosphatidylethanolamine mixtures(Ref. 0044). Monoclonal antibody to amphomycin is a tool to study the topography of dolichol monophosphate in the membrane(Ref. 0101).	[0039] / [0043] / [0044] / [0048] / [0050] / [0051] / [0053] / [0055] / [0056] / [0059] / [0060] / [0061] / [0065] / [0066] / [0067] / [0071] / [0072] / [0079] / [0094] / [0095] / [0096] / [0097] / [0098] / [0099] / [0100] / [0101]
71		Dolichyl-21 monophosphate, a-Dihydroheneicosaprenyl monophosphate	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66Z,70Z,74E,78E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79,83-Henicosamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78,82-tetraoctacontaeicosaen-1-yl monophosphate	IIP0071	Yoshichika Yoshioka	Dol-21-P	C₁₀₅H₁₇₃O₄P	1530.468		Role of Dol-P in regulation of protein glycosylation in 2-acetylaminofluorene-induced carcinogenesis in rat liver(Ref. 0050). Effect of Dol-P concentration on the formation of lipid-saccharides and the N-glycosylation of protein by thyroid ER vesicles(Ref. 0095). The microsomal fraction of liver has been found to catalyze glucose transfer from UDPG to a lipid acceptor to be identical to the compound obtained by chemical phosphorylation of Dol(Ref. 0096). The biological role of Dol (review)(Ref. 0043). Dol-P pathway leading to N-glycosylation of protein(Ref. 0097). Content of Dol and activity of GlcNAc-1-P (UDP-N-acetylglucosamine:Dol-P N-acetylglucosamine 1-phosphate transferase) in fibroblasts from patients with carbohydrate-deficient-glycoprotein (CDG) syndrome were analyzed. The major defect of CDG syndrome is not found in the synthesys of dolichyl phosphate or GlcNAc-PP-Dol(Ref. 0061). Dol-P is a potent inducer of apoptosis in rat glioma cells. Apoptotic changes were also observed in HL-60 cells, SIRC cells and HeLa cells(Ref. 0098). Exogenous Dol-P induced apoptosis in the human monoblastic leukemia cell line U937 within 4 hours. Dol-P-induced apoptosis is mediated by mitogen-activated protein kinase (MAP kinase) cascade(Ref. 0099). Treatment of U937 cells with Dol-P led to an increase in the activity of the ICE family protease CPP32, accompanied with cleavage of pre-CPP32 to generate p17. The modulation od cAMP synthesis due to the stimulation of adenylate cyclase by Dol-P plays a critical role in CPP32 activation and apoptosis(Ref. 0100). Dolichyl, dihydroheptaprenyl, and dihydrodecaprenyl phosphates induced apoptosis in U937 cells, while farnesyl phosphate, geranylgeranyl phosphate, dolichol, dolichal, and dolichoic acid did not induce apoptosis. Apoptosis induced by dihydroprenyl phosphate was mediated by caspase-3-like activation but not by caspase-1-like activation(Ref. 0065).												HPLC (with chromatograph)(Ref. 0094/0048/0051). Sequential microanalyses of free dolichol, dolichyl fatty acid ester and dolichyl phosphate in human serum were made fluorometrically by HPLC. The calibration curve of dolichol standard against the internal standard showed linearity at dolichol concentrations of 10ng to 500ng(Ref. 0053).	Direct estimation of dolichyl phosphate in rat liver by high pressure liquid chromatography(Ref. 0094). Human liver and testis(Ref. 0048). Rat liver(Ref. 0048). Contents in human tissues (adrenal, aorta, colon, heart, kidney, liver, lung, muscle, pancreas, pituitary gland, prostate, small intestine, spleen, testis, tyroid grand, and stomach)(Ref. 0055). Rat and human tissues (spleen, liver, kidney, myocardium, lung, pancreas, adrenal)(Ref. 0051). Levels of dolichyl phosphate in neonatal and adult human tissues (liver, heart, kidney, lung, spleen)(Ref. 0056). Content in human serum(Ref. 0053).		Rat liver hyperplastic nodules(Ref. 0009). Human liver cirrosis and hepatocarcinoma (Ref. 0048). The amount was greatly decreased in hyperplastic nodules of rat liver(Ref. 0050). Effect of age on the content in brain, liver, spleen, kidney, and testis of the rat(Ref. 0067). Age-related chnges of Dol-P content in rat and human tissues (spleen, liver, kidney, heart, lung, pancreas, adrenal)(Ref. 0051). The uptake of F-PP and GG-PP was studied using primary cultures of chromaffin cells. Dolichylmonophosphate and isopentenyl pyrophosphate promoted the uptake (Ref. 0079). Contents of various organs of mice used as a model for Niemann-Pick's type C disease (liver, spleen, kidney, brain, testis, lung, adipose tissue, heart, intestine, skeletal muscle). Contents in subfractions isolated from the liver of mice used as a model for NPC (mitocondria, lysosomes, microsomes)(Ref. 0071). The effects of TSH on Dol-linked sugar pools and oligosaccharyl transferase activity in thyroid cells were investigated. TSH slightly increased the amount of Dol-P and acitivated the oligosaccharyltransferase(Ref. 0072). Modifications in the concentration and distribution of rat liver microsomal dolichol and dolichyl phosphate after acute ethanol adiministration (6 g/kg body weight) were investigated. Between 3 and 24 hr after ethanol administration, the microsomal dolichyl phosphate concentration was significantly lower than in control rats. An earlier and more marked reduction of total Dol was observed in the Golgi apparatus(Ref. 0059). Pro-oxidant agents lead to a significant decrease of both free Dol and Dol-P in isolated rat hepatocytes(Ref. 0059).		Monoclonal antibody to amphomycin is a tool to study the topography of dolichol monophosphate in the membrane(Ref. 0101).	[0009] / [0043] / [0048] / [0050] / [0051] / [0053] / [0055] / [0056] / [0059] / [0061] / [0065] / [0067] / [0071] / [0072] / [0079] / [0094] / [0095] / [0096] / [0097] / [0098] / [0099] / [0100] / [0101]
72		Dolichyl-22 monophosphate, a-Dihydrodocosaprenyl monophosphate	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66Z,70Z,74Z,78E,82E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79,83,87-Docosamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78,82,86-octaoctacontahenicosaen-1-yl monophosphate	IIP0072	Yoshichika Yoshioka	Dol-22-P	C₁₁₀H₁₈₁O₄P	1598.586		The biological role of dolichol (review)(Ref. 0043). Dolichyl phosphate is a potent inducer of apoptosis in rat glioma cells. Apoptotic changes were also observed in HL-60 cells, SIRC cells and HeLa cells(Ref. 0098). Treatment of U937 cells with dolichyl phosphate led to an increase in the activity of the ICE family protease CPP32, accompanied with cleavage of pre-CPP32 to generate p17. The modulation od cAMP synthesis due to the stimulation of adenylate cyclase by dolichyl phosphate plays a critical role in CPP32 activation and apoptosis(Ref. 0100).												HPLC (with chromatograph)(Ref. 0048/0051).	Human liver and testis(Ref. 0048). Rat and human tissues (spleen, liver, kidney, myocardium, lung, pancreas, adrenal)(Ref. 0051).		Rat liver hyperplastic nodules(Ref. 0048). Human liver cirrosis and hepatocarcinoma(Ref. 0048). Age-related chnges of dolichyl phosphate content in rat and human tissues (spleen, liver, kidney, heart, lung, pancreas, adrenal)(Ref. 0051). Contents of various organs of mice used as a model for Niemann-Pick's type C disease (liver, spleen, kidney, brain, testis, lung, adipose tissue, heart, intestine, skeletal muscle). Contents in subfractions isolated from the liver of mice used as a model for NPC (mitocondria, lysosomes, microsomes)(Ref. 0071).			[0043] / [0048] / [0051] / [0071] / [0098] / [0100]
73		Dolichyl-17 diphosphate, a-Dihydroheptadecaprenyl diphosphate	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58E,62E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67-Heptadecamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66-octahexacontahexadecaen-1-yl diphosphate	IIP0073	Yoshichika Yoshioka	Dol-17-PP	C₈₅H₁₄₂O₇P₂	1337.980		Calf brain microsomes catalyze the enzymatic release of P from exogenous Dol-PP by a bacitracin-sensitive reaction(Ref. 0102). Metabolic labeling of rat liver slices with mevalonic acid revealed the accumulation of E,E,E-geranylgeranyl (di)phosphate as well as dolichyl (di)phosphate (C85 and C90) and dehydrodolichol (C85 and C90), but no accumulation of Z,E,E-geranylgeranyl (di)phosphate or E,E-farnesyl (di)phosphate was detected(Ref. 0026).															The effects of TSH on dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells were investigated. TSH slightly increased the amount of dolichol-PP and acitivated the oligosaccharyltransferase(Ref. 0072).			[0026] / [0072] / [0102]
74		Dolichyl-18 diphosphate, a-Dihydrooctadecaprenyl diphosphate	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62E,66E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71-Octadecamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70-doheptacontaheptadecaen-1-yl diphosphate	IIP0074	Yoshichika Yoshioka	Dol-18-PP	C₉₀H₁₅₀O₇P₂	1406.097		Metabolic labeling of rat liver slices with mevalonic acid revealed the accumulation of E,E,E-geranylgeranyl (di)phosphate as well as dolichyl (di)phosphate (C85 and C90) and dehydrodolichol (C85 and C90), but no accumulation of Z,E,E-geranylgeranyl (di)phosphate or E,E-farnesyl (di)phosphate was detected(Ref. 0026).															The effects of TSH on dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells were investigated. TSH slightly increased the amount of dolichol-PP and acitivated the oligosaccharyltransferase(Ref. 0072).			[0026] / [0072]
75		Dolichyl-19 diphosphate, a-Dihydrononadecaprenyl diphosphate	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66E,70E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75-Nonadecamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74-hexaheptacontaoctadecaen-1-yl diphosphate	IIP0075	Yoshichika Yoshioka	Dol-19-PP	C₉₅H₁₅₈O₇P₂	1474.214																	The effects of TSH on dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells were investigated. TSH slightly increased the amount of dolichol-PP and acitivated the oligosaccharyltransferase(Ref. 0072).			[0072]
76		Dolichyl-20 diphosphate, a-Dihydroeicosaprenyl diphosphate	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66Z,70E,74E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79-Eicosamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78-octacontanonadecaen-1-yl diphosphate	IIP0076	Yoshichika Yoshioka	Dol-20-PP	C₁₀₀H₁₆₆O₇P₂	1542.331																	The effects of TSH on dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells were investigated. TSH slightly increased the amount of dolichol-PP and acitivated the oligosaccharyltransferase(Ref. 0072).			[0072]
77		Dolichyl-21 diphosphate, a-Dihydroheneicosaprenyl diphosphate	[6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66Z,70Z,74E,78E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79,83-Henicosamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78,82-tetraoctacontaeicosaen-1-yl diphosphate	IIP0077	Yoshichika Yoshioka	Dol-21-PP	C₁₀₅H₁₇₄O₇P₂	1610.448																	The effects of TSH on dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells were investigated. TSH slightly increased the amount of dolichol-PP and acitivated the oligosaccharyltransferase(Ref. 0072).			[0072]
78		C12 a, w-dibasic prenoic acid	[2E,6E]-3,7-Dimethyl-2,6-decadien-1,10-dioic acid	IIP0078	Hiroshi Sagami		C₁₂H₁₈O₄	226.269																	Isolated embryonic Drosophila cell extracts metabolize farnesyl diphosphate and farnesol to identical products. Two of the major products were identified as trans,trans-3,7,11-trimethyl-2,6,10-dodecatrien-1,12-dioic acid and trans-3,7-dimethyl-2,6-decadien-1,10-dioic acid.(Ref. 0103)			[0103]
79		C15 a, w-dibasic prenoic acid	[2E,6E,10E]-3,7,11-Trimethyl-2,6,10-dodecatrien-1,12-dioic acid	IIP0079	Hiroshi Sagami		C₁₅H₂₂O₄	266.333																	Isolated embryonic Drosophila cell extracts metabolize farnesyl diphosphate and farnesol to identical products. Two of the major products were identified as trans,trans-3,7,11-trimethyl-2,6,10-dodecatrien-1,12-dioic acid and trans-3,7-dimethyl-2,6-decadien-1,10-dioic acid.(Ref. 0103)			[0103]
80		All-trans Farnesyl amine	[2E,6E]-3,7,11-Trimethyl-2,6,10-dodecatrienyl amine	IIP0080	Hiroshi Sagami	F-NH2	C₁₅H₂₇N	221.382		Farnesylamine, an analogue of farnesol, inhibit growth of PAP2 cells in a dose-dependent manner (Ref. 0104).														All-trans farnesylamine can be synthesized from all-trans farnesol by the Gabriel synthesis (Ref. 0104).				[0104]
81		cis,cis-Farnesol	[2Z,6Z]-3,7,11-Trimethyl-2,6,10-dodecatrienic acid	IIP0081	Hiroshi Sagami		C₁₅H₂₄O₂	236.350																	cis,cis-Farnesoic acid , trans,trans-farnesoic acid, trans,trans,trans-geranylgeranoic acid, and an unidentified C20 isoprenoid acid containing at least one cis-double bond was found as mevalonate-derived metabolites with cell-free homogenates of bovine retinas (Ref. 0105)			[0105]
82		Plaunotol	[2E,6Z,10E]-7-Hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol	IIP0082	Hiroshi Sagami		C₂₀H₃₄O₂	306.483															Plaunotol was isolated as a potent antipeptic ulcer substance from a Thai medicinal plant identified with Croton sublyratus Kurz.(Ref. 0107)					[0107]
83		12(S)-hydroxygeranylgeraniol	[2E,6E,10E]-12-Hydroxy-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-ol	IIP0083	Hiroshi Sagami		C₂₀H₃₄O₂	306.483		Cytotoxicity against cultured human tumor cell lines, A549, SK-OV-3, SK-MEL-2, XF498, and HCT15, with ED50 values ranging from 4.1-8.3 micrograms/ml. (Ref. 0108)													12(S)-hydroxygeranylgeraniol and (2E,10E]-1,12-dihydroxy-18-acetoxy-3,7,15-trimethylhexadeca-2,10,14-triene were isolated from the aerical parts of Carpesium divaricatum.(Ref. 0108)					[0108]
84		13(S)-hydroxygeranylgeraniol	[2E,6E,10E]-13-Hydroxy-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-ol	IIP0084	Hiroshi Sagami		C₂₀H₃₄O₂	306.483																	13(S)-Hydroxygeranylgeraniol-derived furanoditerpenes were isolated from a sample of the brown alga Bifurcaria bifurcata collected from Brittany on the Atlanticcoast.(Ref. 0109)			[0109]
85		12-Hydroxyfarnesol	[2E,6E,10E]-12-Hydroxy-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol	IIP0085	Hiroshi Sagami		C₁₅H₂₆O₂	238.366																	12-Hydroxy farnesol is formed from farnesol by the action of a cytochrome P450 terpenoid hydroxylase. (Ref. 0110)			[0110]
86		10-Hydroxygeraniol	[2E,6Z]-7-Hydroxymethyl-3-methyl-2,6-octadiene-1-ol	IIP0086	Hiroshi Sagami		C₁₀H₁₈O₂	170.249																	10-Hydroxygeraniol is formed from geraniol by the action of acyclic monoterpene primary alcohol:NADP+ oxidereductase.(Ref. 0111)			[0111]
87		Glc-phosphoryldolichol (family), Glucosylphosphoryldolichol (family)		IIP0087	Hiroshi Sagami	Glc-P-Dol																			Glc-P-dolichol serves as a glycosyl donor in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol.(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
88		Man-phosphoryldolichol (family), Mannosylphosphoryldolichol (family)		IIP0088	Hiroshi Sagami	Man-P-Dol																			Man-P-dolichol serves as a glycosyl donor in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol and in the biosynthesis of O-linked oligosaccharides and the yeast GPI anchor .(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
89		GlcNAc-pyrophosphoryldolichol (family), N-Acetylglcosaminylpyrophosphoryldolichol (family)		IIP0089	Hiroshi Sagami	GlcNAc-PP-Dol																			The first lipid intermediate in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol.(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
90		(GlcNAc)2-pyrophosphoryldolichol (family)		IIP0090	Hiroshi Sagami	(GlcNAc)2-PP-Dol																			A lipid intermediate in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol.(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
91		Man(GlcNAc)2-pyrophosphoryldolichol (family)		IIP0091	Hiroshi Sagami	Man(GlcNAc)2-PP-Dol																			A lipid intermediate in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol.(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
92		(Man)2(GlcNAc)2-pyrophosphoryldolichol (family)		IIP0092	Hiroshi Sagami	(Man)2(GlcNAc)2-PP-Dol																			A lipid intermediate in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol.(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
93		(Man)3(GlcNAc)2-pyrophosphoryldolichol (family)		IIP0093	Hiroshi Sagami	(Man)3(GlcNAc)2-PP-Dol																			A lipid intermediate in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol.(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
94		(Man)4(GlcNAc)2-pyrophosphoryldolichol (family)		IIP0094	Hiroshi Sagami	(Man)4(GlcNAc)2-PP-Dol																			A lipid intermediate in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol.(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
95		(Man)5(GlcNAc)2-pyrophosphoryldolichol (family)		IIP0095	Hiroshi Sagami	(Man)5(GlcNAc)2-PP-Dol																			A lipid intermediate in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol.(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
96		(Man)6(GlcNAc)2-pyrophosphoryldolichol (family)		IIP0096	Hiroshi Sagami	(Man)6(GlcNAc)2-PP-Dol																			A lipid intermediate in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol.(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
97		(Man)7(GlcNAc)2-pyrophosphoryldolichol (family)		IIP0097	Hiroshi Sagami	(Man)7(GlcNAc)2-PP-Dol																			A lipid intermediate in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol.(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
98		(Man)8(GlcNAc)2-pyrophosphoryldolichol (family)		IIP0098	Hiroshi Sagami	(Man)8(GlcNAc)2-PP-Dol																			A lipid intermediate in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol.(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
99		(Man)9(GlcNAc)2-pyrophosphoryldolichol (family)		IIP0099	Hiroshi Sagami	(Man)9(GlcNAc)2-PP-Dol																			A lipid intermediate in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol.(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
100		Glc(Man)9(GlcNAc)2-pyrophosphoryldolichol (family)		IIP0100	Hiroshi Sagami	Glc(Man)9(GlcNAc)2-PP-Dol																			A lipid intermediate in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol.(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
101		(Glc)2(Man)9(GlcNAc)2-pyrophosphoryldolichol (family)		IIP0101	Hiroshi Sagami	(Glc)2(Man)9(GlcNAc)2-PP-Dol																			A lipid intermediate in the assembly of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol.(Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
102		(Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol (family)		IIP0102	Hiroshi Sagami	(Glc)3(Man)9(GlcNAc)2-PP-Dol																			The oligosaccharide chain of (Glc)3(Man)9(GlcNAc)2-pyrophosphoryldolichol is transferred to the asparagine side chain of proteins with an Asn-X-Ser/Thr motif. (Ref. 0012/0013/0014)			[0012] / [0013] / [0014]
103		Dehydrodolichol (family)		IIP0103	Yoshichika Yoshioka	De-dol				Metabolic labeling of rat liver slices with mevalonic acid revealed the accumulation of E,E,E-geranylgeranyl (di)phosphate as well as dolichyl (di)phosphate (C85 and C90) and dehydrodolichol (C85 and C90), but no accumulation of Z,E,E-geranylgeranyl (di)phosphate or E,E-farnesyl (di)phosphate was detected(Ref. 0026).												Separation of dolichol from dehydrodolichol (C75-C100) by a simple two-plate thin-layer chromatography(Ref. 0052).			Formation of dolichol from dehydrodolichol (C90-C100) is catalyzed by NADPH- dependent reductase localized in microsomes of rat liver(Ref. 0092). Dehydrodolichol (C65-C95) was detected in the nonpolar products formed from isopentenyl diphosphate and farnesyl diphosphate in the reaction with a crude 1000 x g supernatant of yeast homogenates in the presence of NADPH. Dehydrodolichol is a common branch point intermediate in the biosynthetic pathways leading to dolichal and dolichol. Dehydrodolichal is an intermediate in the pathway from dehydrodolichol to dolichal (Ref. 0073).			[0026] / [0052] / [0073] / [0092]
104		Dehydrodolichal (family)		IIP0104	Yoshichika Yoshioka	De-dolichal																		Synthesized by treating dehydrodolichol with MnO2(Ref. 0073).	Dehydrodolichal (C75-C80) was detected in the nonpolar products formed from isopentenyl diphosphate and farnesyl diphosphate in the reaction with a crude 1000 x g supernatant of yeast homogenates in the presence of NADPH. Dehydrodolichol is a common branch point intermediate in the biosynthetic pathways leading to dolichal and dolichol. Dehydrodolichal is an intermediate in the pathway from dehydrodolichol to dolichal (Ref. 0073).			[0073]
105		Dolichol (family)		IIP0105	Hiroshi Sagami	Dol				Review(Ref. 0115)																		[0115]
106		Dolichal (family)		IIP0106	Yoshichika Yoshioka																			Synthesized by treatment of dolichol with pyridinium dichromate(Ref. 0073).				[0073]
107		Dolichoic acid (family)		IIP0107	Yoshichika Yoshioka																				Metabolism of dolichol, dolichoic acid, and nordolichoic acid in MDCK and HepG2 cells were investigated. Dolichoic acid was broken down by alpha-oxidation and also converted to a mixture of polar compounds. No oxidative breakdown of dolichol was found(Ref. 0074).			[0074]
108		trans-polyprenol (family)		IIP0108	Hiroshi Sagami																		Chicle resin contains trans- and cis-polyisoprenes(Ref. 0116).				Review (Structure and biosynthesis mechanism of natural polyisoprene )(Ref. 0116)	[0116]
109		Dehydrodolichyl phosphate (family)		IIP0109	Yoshichika Yoshioka	De-dol-P
110		Dehydrodolichyl diphosphate (family)		IIP0110	Yoshichika Yoshioka	De-dol-PP				Several detergents activated microsomal dehydrodolichyl diphosphate synthase of rat liver, but the chain length of products shifted downward from C90 and C95 with increasing concentration of the detergents(Ref. 0117).																		[0117]
111		Dolichyldolichoate (family)		IIP0111	Hiroshi Sagami																		Dolichyl dolichoate was found in the neutral lipid fraction of bovine thyroid(Ref. 0118).					[0118]
112	No image	Tetrahydroxybacteriohopane/bacteriohopanetetrol	1,2,3,4-Tetrahydroxypentane-29-hopane	IIP0112	Yasutaka Tahara	THBH	C₃₅H₆₂O₄	546.864		THBH may be localized in membranes , playing there the same role as sterols play in eukaryotes , as a result of their similar size , rigidity , and amphiphilic character . (Ref. 0005)	181-182					Solubled in chloroform		3340,2920,2860,1360,1140,1110cm^-¹(Ref. 0001)	¹H-NMR(CDCl₃):d0.683(3H,s,18a-CH₃),0.791(3h,s,4b-CH₃),0.812(3h,s,4a-CH₃),0.846(3h,s,10b-CH₃),0.904(3h,d,J=6,22R-CH₃),0.944(6H,s,8band 14aCH₃),2.055(3H,s,CH₃COO^-),2.076(3h,s,CH₃COO^-),2.083(3H,s,CH₃COO^-)2.088(3H,s,CH₃COO^-),4.15(1H,dd,J₃₅_a,₃₅=12,J₃₅_a,₃₄=6,35H_a),4.39(1H,dd,J₃₅_a,₃₅_b=12,J₃₅_a,₃₄=3,35-H_b), 5.03(1H,dt,J₃₂₃₃=9,J₃₂₃₁=3.5,32-H), 5.24(2H,m,33-H and 34-H)(Ref. 0002)¹³C-NMR(CDCl₃):40.4(C-1),18.7(C-2),42.1(C-3),33.4(C-4),56.2(C-5),18.7(C-6),33.3(C-7),41.8(C-8),50.5(C-9),37.5(C-10),20.9(C-11),24.0(C-12),49.4(C-13),41.8(C-14),33.8(C-15),22.8(C-16),54.5(C-17),44.4(C-18),41.6(C-19),27.5(C-20),46.0(C-21),36.1(C-22),33.4(C-23),21.6(C-24),15.9(C-25),16.6(C-26),16.6(C-27),15.9(C-28),19.8(C-29),30.9(C-30),26.3(C-31),69.6(C-32),71.7(C-33),72.0(C-34),62.1(C-35),20.6(2,20.8,20.9(CH₃CO^-),169.6,169.8,170.2,170.5(CH₃CO^-)(Ref. 0002)	EI-MS as a tetraacetate derivative:714(M⁺),493(M⁺-C₁₆H₂₉),369(C₂₇H₄₅⁺),191(C₁₄H₂₃⁺),137(C₁₀H₁₇⁺),95(C₇H₁₁⁺)(Ref. 0001/0002)		TLC(Rf0.62 on silica gel H by chloroform/methanol/water,60:10:1,v/v)(Ref. 0001)GC(Retention time 28min as anacetylated derivative of 1-hydroxyethyl-29-hopane on a OV1/Gas Chrom Q column (2mm by 180cm) at a tenperature gradient from 180-300C at 4C/min(Ref. 0003)	Cyanobasteria(Anabena variabilis,Calothrix sp.,Fischerella sp.,Nostoc muscorum B,Ascillatoria sp.,Scytonema sp.,Synechocystis sp.),Purple non-sulphur bacteria(Rhodomicrobium vannielii,Rhodoseudomonas acidphila,Rhodoseudomonas palustris,Rhodospirillum rubrum),Methylotrophs(Methylomonas albus,Methlomonas methanica,Methylocystis parvus,Methylosinus sporium,Methylosinus trichosporium,Methylococcus capsulatus),Gram-nagative chomoautotrophs(Nitrsomonas europaea),Gram-nagative chemoheterotrophs(Metylobacterium organophilum,Hyphomicrobiumsp.,Pseudomonas cepacia, Azotobacter chroococcum,Azotobacter vinelandii,Zymomonas mobilis),Acetic acid bacteria(A.aceti,A.liquefaciens,A.xylininum,A.pasteurianus,A.lovaniensis,A.orleanensis,A.pasteurianus,A.peroxydans,Gluconobacter oxydans),Gram-positive bacteria(Bacillus acidocaldarius,Streptomyces chartreusis,Streptomyces sp.)(Ref. 0004)		Tetrahydroxypentane side-chain of THBH could be a D-ribose derivative linked through the C-5 carbon atom to hopane-22(29)-ene , hopane skelton . (Ref. 0006/0007)	Gene of squalene cyclase catalyzing cyclization of squalene to form hopane-22(29)-ene has been cloned and sequenced . (Ref. 0008)		[0001] / [0002] / [0003] / [0004] / [0005] / [0006] / [0007] / [0008]

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AUTHOR	:	Yasugi, E., Nakasuji, M., Dohi, T., and Oshima, M.
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AUTHOR	:	Aberg, F., Jakobsson-Borin, A., Olsson, M., Brunk, U., and Dallner, G.
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[0063]

AUTHOR	:	Hjertman, M., Wejde, J., Dricu, A., Carlberg, M., Griffiths, W. J., Sjovall, J., and Larsson, O.
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