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Isoprenoid


DATA No : IIP0055 INFORMANT : Yoshichika Yoshioka

NAME : [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

COMMON NAME: Dolichol-18, a-Dihydrooctadecaprenol
SYMBOL: Dol-18
FORMULA: C90H148O MOL.WT (average) : 1246.138


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BIOLOGICAL ACTIVITY
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).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA: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).

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA
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).
SOURCE
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).
CHEMICAL SYNTHESIS

METABOLISM
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).
GENETIC INFORMATION

NOTE
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).
REFERENCES
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VOL:38 PAGE : 2216-2223 (1997)
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[0043]
AUTHOR:Chojnacki, T., and Dallner, G.
TITLE:The biological role of dolichol PubMed ID:3291859
JOURNAL:Biochem J.
VOL:251 PAGE : 1-9 (1988)
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[0045]
AUTHOR:Tanaka, Y., Sato, H., Kageyu, A., and Tomita, T.
TITLE:Determination of arrangement of isoprene units in pig liver dolichol by 13C-n.m.r. spectroscopy PubMed ID:3632632
JOURNAL:Biochem J.
VOL:243 PAGE : 481-485 (1987)
[TOP]

[0046]
AUTHOR:James, M. J., and Kandutsch, A. A.
TITLE:Elevated dolichol synthesis in mouse testes during spermatogenesis PubMed ID:7350150
JOURNAL:J Biol Chem.
VOL:255 PAGE : 16-19 (1980)
[TOP]

[0047]
AUTHOR:Kin, N. M., and Wolfe, L. S.
TITLE:Presence of abnormal amounts of dolichols in the urinary sediment of Batten disease patients PubMed ID:7110772
JOURNAL:Pediatr Res.
VOL:16 PAGE : 530-532 (1982)
[TOP]

[0048]
AUTHOR:Eggens, I., Chojnacki, T., Kenne, L., and Dallner, G.
TITLE:Separation, quantitation and distribution of dolichol and dolichyl phosphate in rat and human tissues PubMed ID:6849949
JOURNAL:Biochim Biophys Acta.
VOL:751 PAGE : 355-368 (1983)
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[0049]
AUTHOR:Ng Ying Kin, N. M., Palo, J., Haltia, M., and Wolfe, L. S.
TITLE:High levels of brain dolichols in neuronal ceroid-lipofuscinosis and senescence PubMed ID:6834069
JOURNAL:J Neurochem.
VOL:40 PAGE : 1465-1473 (1983)
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[0050]
AUTHOR:Eggens, I., Eriksson, L. C., Chojnacki, T., and Dallner, G.
TITLE:Role of dolichyl phosphate in regulation of protein glycosylation in 2-acetylaminofluorene-induced carcinogenesis in rat liver PubMed ID:6318977
JOURNAL:Cancer Res.
VOL:44 PAGE : 799-805 (1984)
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[0051]
AUTHOR:Kalen, A., Appelkvist, E. L., and Dallner, G.
TITLE:Age-related changes in the lipid compositions of rat and human tissues PubMed ID:2779364
JOURNAL:Lipids.
VOL:24 PAGE : 579-584 (1989)
[TOP]

[0052]
AUTHOR:Sagami, H., Kurisaki, A., Ogura, K., and Chojnacki, T.
TITLE:Separation of dolichol from dehydrodolichol by a simple two-plate thin-layer chromatography PubMed ID:1479294
JOURNAL:J Lipid Res.
VOL:33 PAGE : 1857-1861 (1992)
[TOP]

[0053]
AUTHOR:Yasugi, E., and Oshima, M.
TITLE:Sequential microanalyses of free dolichol, dolichyl fatty acid ester and dolichyl phosphate levels in human serum PubMed ID:8123674
JOURNAL:Biochim Biophys Acta.
VOL:1211 PAGE : 107-113 (1994)
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[0054]
AUTHOR:Rupar, C. A., and Carroll, K. K.
TITLE:Occurrence of dolichol in human tissues PubMed ID:661513
JOURNAL:Lipids.
VOL:13 PAGE : 291-293 (1978)
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[0055]
AUTHOR:Tollbom, O., and Dallner, G.
TITLE:Dolichol and dolichyl phosphate in human tissues PubMed ID:3641633
JOURNAL:Br J Exp Pathol.
VOL:67 PAGE : 757-764 (1986)
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[0056]
AUTHOR:Carroll, K. K., Guthrie, N., and Ravi, K.
TITLE:Dolichol: function, metabolism, and accumulation in human tissues PubMed ID:1449704
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VOL:70 PAGE : 382-384 (1992)
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[0057]
AUTHOR:Ishinaga, M.
TITLE:Effects of aging and diet on the accumulation of dolichol in rat tissues PubMed ID:9213436
JOURNAL:Biochem Cell Biol.
VOL:74 PAGE : 265-270 (1996)
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[0058]
AUTHOR:Zhang, Y., Appelkvist, E. L., Kristensson, K., and Dallner, G.
TITLE:The lipid compositions of different regions of rat brain during development and aging PubMed ID:9363798
JOURNAL:Neurobiol Aging.
VOL:17 PAGE : 869-875 (1996)
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[0059]
AUTHOR:Cottalasso, D., Bellocchio, A., Pronzato, M. A., Domenicotti, C., Traverso, N., Gianelli, M. V., Marinari, U. M., and Nanni, G.
TITLE:Effect of ethanol administration on the level of dolichol in rat liver microsomes and Golgi apparatus PubMed ID:9622457
JOURNAL:Alcohol Clin Exp Res.
VOL:22 PAGE : 730-737 (1998)
[TOP]

[0060]
AUTHOR:Thelin, A., Low, P., Chojnacki, T., and Dallner, G.
TITLE:Covalent binding of dolichyl phosphate to proteins in rat liver PubMed ID:1999193
JOURNAL:Eur J Biochem.
VOL:195 PAGE : 755-761 (1991)
[TOP]

[0061]
AUTHOR:Yasugi, E., Nakasuji, M., Dohi, T., and Oshima, M.
TITLE:Major defect of carbohydrate-deficient-glycoprotein syndrome is not found in the synthesis of dolichyl phosphate or N-acetylglucosaminyl-pyrophosphoryl-dolichol PubMed ID:8179616
JOURNAL:Biochem Biophys Res Commun.
VOL:200 PAGE : 816-820 (1994)
[TOP]

[0062]
AUTHOR:Aberg, F., Jakobsson-Borin, A., Olsson, M., Brunk, U., and Dallner, G.
TITLE:Influence of dolichol on microsomal membrane functions PubMed ID:8832099
JOURNAL:Cell Mol Biol (Noisy-le-grand).
VOL:42 PAGE : 683-690 (1996)
[TOP]

[0063]
AUTHOR:Hjertman, M., Wejde, J., Dricu, A., Carlberg, M., Griffiths, W. J., Sjovall, J., and Larsson, O.
TITLE:Evidence for protein dolichylation PubMed ID:9373159
JOURNAL:FEBS Lett.
VOL:416 PAGE : 235-238 (1997)
[TOP]

[0065]
AUTHOR:Yasugi, E., Nakata, K., Yokoyama, Y., Kano, K., Dohi, T., and Oshima, M.
TITLE:Dihydroheptaprenyl and dihydrodecaprenyl monophosphates induce apoptosis mediated by activation of caspase-3-like protease PubMed ID:9461254
JOURNAL:Biochim Biophys Acta.
VOL:1389 PAGE : 132-140 (1998)
[TOP]

[0066]
AUTHOR:Crick, D. C., and Rip, J. W.
TITLE:Age-associated changes in dolichol and dolichyl phosphate metabolism in the kidneys and liver of mice PubMed ID:2752016
JOURNAL:Biochim Biophys Acta.
VOL:1004 PAGE : 180-186 (1989)
[TOP]

[0067]
AUTHOR:Keller, R. K., and Nellis, S. W.
TITLE:Quantitation of dolichyl phosphate and dolichol in major organs of the rat as a function of age PubMed ID:3724371
JOURNAL:Lipids.
VOL:21 PAGE : 353-355 (1986)
[TOP]

[0068]
AUTHOR:Monma, N., Satodate, R., Suzuki, H., and Ujiie, T.
TITLE:Ceroid-lipofuscinosis. Report of two autopsy cases PubMed ID:2468263
JOURNAL:Acta Pathol Jpn.
VOL:38 PAGE : 1191-1203 (1988)
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[0069]
AUTHOR:Henry, A., Stacpoole, P. W., and Allen, C. M.
TITLE:Dolichol biosynthesis in human malignant cells PubMed ID:1654890
JOURNAL:Biochem J.
VOL:278 (Pt 3) PAGE : 741-747 (1991)
[TOP]

[0070]
AUTHOR:Sagami, H., Korenaga, T., and Ogura, K.
TITLE:Geranylgeranyl diphosphate synthase catalyzing the single condensation between isopentenyl diphosphate and farnesyl diphosphate PubMed ID:8407863
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VOL:114 PAGE : 118-121 (1993)
[TOP]

[0071]
AUTHOR:Schedin, S., Pentchev, P. G., Brunk, U., and Dallner, G.
TITLE:Changes in the levels of dolichol and dolichyl phosphate in a murine model of Niemann-Pick's type C disease PubMed ID:7616223
JOURNAL:J Neurochem.
VOL:65 PAGE : 670-676 (1995)
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[0072]
AUTHOR:Desruisseau, S., Valette, A., Franc, J. L., and Chabaud, O.
TITLE:Thyrotropin controls dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells PubMed ID:8902853
JOURNAL:Mol Cell Endocrinol.
VOL:122 PAGE : 223-228 (1996)
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[0073]
AUTHOR:Sagami, H., Igarashi, Y., Tateyama, S., Ogura, K., Roos, J., and Lennarz, W. J.
TITLE:Enzymatic formation of dehydrodolichal and dolichal, new products related to yeast dolichol biosynthesis PubMed ID:8621629
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VOL:271 PAGE : 9560-9566 (1996)
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[0074]
AUTHOR:Van Houte, H. A., Van Veldhoven, P. P., Mannaerts, G. P., Baes, M. I., and Declercq, P. E.
TITLE:Metabolism of dolichol, dolichoic acid and nordolichoic acid in cultured cells PubMed ID:9233691
JOURNAL:Biochim Biophys Acta.
VOL:1347 PAGE : 93-100 (1997)
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[0075]
AUTHOR:Marino, M., Dolfi, C., Paradiso, C., Cavallini, G., Gori, Z., Innocenti, B., Maccheroni, M., Masini, M., Pollera, M., Trentalance, A., et al.
TITLE:Accumulation of dolichol and impaired signal transduction in aging PubMed ID:9553626
JOURNAL:Aging (Milano).
VOL:9 PAGE : 433-434 (1997)
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[0076]
AUTHOR:Marino, M., Dolfi, C., Paradiso, C., Cavallini, G., Masini, M., Gori, Z., Pollera, M., Trentalance, A., and Bergamini, E.
TITLE:Age-dependent accumulation of dolichol in rat liver: is tissue dolichol a biomarker of aging? PubMed ID:9520903
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VOL:53 PAGE : B87-93 (1998)
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[0077]
AUTHOR:Humaloja, K., Salaspuro, M., and Roine, R. P.
TITLE:Biliary excretion of dolichols and beta-hexosaminidase--effect of ethanol and glucagon PubMed ID:9397402
JOURNAL:Lipids.
VOL:32 PAGE : 1169-1172 (1997)
[TOP]

[0091]
AUTHOR:Crick, D. C., and Carroll, K. K.
TITLE:Absorption and distribution of [1-14C]dolichol intubated into rats PubMed ID:3606856
JOURNAL:Biochem Cell Biol.
VOL:65 PAGE : 317-320 (1987)
[TOP]

[0092]
AUTHOR:Sagami, H., Kurisaki, A., and Ogura, K.
TITLE:Formation of dolichol from dehydrodolichol is catalyzed by NADPH-dependent reductase localized in microsomes of rat liver PubMed ID:8486680
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VOL:268 PAGE : 10109-10113 (1993)
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[0106]
AUTHOR:Nanni, G., Canepa, C., Majorani, F., and Casu, A.
TITLE:Content of dolichol and retinol in isolated rat non-parenchymal liver cells PubMed ID:9747512
JOURNAL:Cell Biochem Funct.
VOL:16 PAGE : 203-209 (1998)
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