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Isoprenoid


DATA No : IIP0068 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-yl monophosphate

COMMON NAME: Dolichyl-18 monophosphate, a-Dihydrooctadecaprenyl monophosphate
SYMBOL: Dol-18-P
FORMULA: C90H149O4P MOL.WT (average) : 1326.117


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BIOLOGICAL ACTIVITY
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).
PHYSICAL AND CHEMICAL PROPERTIES
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SPECTRAL DATA
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CHROMATOGRAM DATA
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).
SOURCE
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).
CHEMICAL SYNTHESIS

METABOLISM
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).
GENETIC INFORMATION

NOTE
Monoclonal antibody to amphomycin is a tool to study the topography of dolichol monophosphate in the membrane(Ref. 0101).
REFERENCES
[0026]
AUTHOR:Sagami, H., Matsuoka, S., and Ogura, K.
TITLE:Formation of Z,E,E-geranylgeranyl diphosphate by rat liver microsomes PubMed ID:1995610
JOURNAL:J Biol Chem.
VOL:266 PAGE : 3458-3463 (1991)
[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]

[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]

[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)
[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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[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)
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[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]

[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]

[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)
[TOP]

[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)
[TOP]

[0079]
AUTHOR:Van Dessel, G., De Busser, H., and Lagrou, A.
TITLE:Internalisation of short-chain isoprenyl diphosphates by chromaffin cells from bovine adrenal medulla PubMed ID:9299441
JOURNAL:Biochem Biophys Res Commun.
VOL:238 PAGE : 7-11 (1997)
[TOP]

[0094]
AUTHOR:Chaudhary, N., Freeman, D. J., Rip, J. W., and Carroll, K. K.
TITLE:Direct estimation of dolichyl phosphate in rat liver by high pressure liquid chromatography PubMed ID:7132586
JOURNAL:Lipids.
VOL:17 PAGE : 558-560 (1982)
[TOP]

[0095]
AUTHOR:Spiro, M. J., and Spiro, R. G.
TITLE:Control of N-linked carbohydrate unit synthesis in thyroid endoplasmic reticulum by membrane organization and dolichyl phosphate availability PubMed ID:2429959
JOURNAL:J Biol Chem.
VOL:261 PAGE : 14725-14732 (1986)
[TOP]

[0096]
AUTHOR:Behrens, N. H., and Leloir, L. F.
TITLE:Dolichol monophosphate glucose: an intermediate in glucose transfer in liver PubMed ID:5273893
JOURNAL:Proc Natl Acad Sci U S A.
VOL:66 PAGE : 153-159 (1970)
[TOP]

[0097]
AUTHOR:Hemming, F. W.
TITLE:Dolichol: a curriculum cognitionis PubMed ID:1449703
JOURNAL:Biochem Cell Biol.
VOL:70 PAGE : 377-381 (1992)
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[0098]
AUTHOR:Yasugi, E., Yokoyama, Y., Seyama, Y., Kano, K., Hayashi, Y., and Oshima, M.
TITLE:Dolichyl phosphate, a potent inducer of apoptosis in rat glioma C6 cells PubMed ID:7488203
JOURNAL:Biochem Biophys Res Commun.
VOL:216 PAGE : 848-853 (1995)
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[0099]
AUTHOR:Dohi, T., Yasugi, E., and Oshima, M.
TITLE:Activation of mitogen activated protein kinase in dolichyl phosphate-induced apoptosis in U937 cells PubMed ID:8694838
JOURNAL:Biochem Biophys Res Commun.
VOL:224 PAGE : 87-91 (1996)
[TOP]

[0100]
AUTHOR:Yokoyama, Y., Okubo, T., Ozawa, S., Nagai, F., Ushiyama, K., Kano, I., Shioda, M., Kubo, H., Takemura, M., Namiki, H., et al.
TITLE:CPP32 activation during dolichyl phosphate-induced apoptosis in U937 leukemia cells PubMed ID:9257710
JOURNAL:FEBS Lett.
VOL:412 PAGE : 153-156 (1997)
[TOP]

[0101]
AUTHOR:Banerjee, D. K., Diaz, A. M., Campos, T. M., Grande, C., Kozek, W. J., and Baksi, K.
TITLE:Monoclonal antibody to amphomycin. A tool to study the topography of dolichol monophosphate in the membrane PubMed ID:1291054
JOURNAL:Carbohydr Res.
VOL:236 PAGE : 301-313 (1992)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.