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Isoprenoid


DATA No : IIP0041 INFORMANT : Yoshichika Yoshioka

NAME : [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

COMMON NAME: Dolichol-17, a-Dihydroheptadecaprenol
SYMBOL: Dol-17
FORMULA: C85H140O MOL.WT (average) : 1178.020


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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 (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
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SPECTRAL DATA
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CHROMATOGRAM DATA
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).
SOURCE
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).
CHEMICAL SYNTHESIS

METABOLISM
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).
GENETIC INFORMATION

NOTE
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).
REFERENCES
[0028]
AUTHOR:Quellhorst, G. J., Jr., Piotrowski, J. S., Steffen, S. E., and Krag, S. S.
TITLE:Identification of Schizosaccharomyces pombe prenol as dolichol-16,17 PubMed ID:9514857
JOURNAL:Biochem Biophys Res Commun.
VOL:244 PAGE : 546-550 (1998)
[TOP]

[0039]
AUTHOR:Hinson, D. D., Chambliss, K. L., Toth, M. J., Tanaka, R. D., and Gibson, K. M.
TITLE:Post-translational regulation of mevalonate kinase by intermediates of the cholesterol and nonsterol isoprene biosynthetic pathways PubMed ID:9392419
JOURNAL:J Lipid Res.
VOL:38 PAGE : 2216-2223 (1997)
[TOP]

[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)
[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)
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[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)
[TOP]

[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)
[TOP]

[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)
[TOP]

[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
JOURNAL:Biochem Cell Biol.
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)
[TOP]

[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)
[TOP]

[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)
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[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)
[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
JOURNAL:J Biochem (Tokyo).
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
JOURNAL:J Biol Chem.
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
JOURNAL:J Gerontol A Biol Sci Med Sci.
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)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.