Isoprenoid
DATA No : IIP0031
INFORMANT : Yoshichika Yoshioka
NAME : [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
| COMMON NAME | : | Dolichol-19, a-Dihydrononadecaprenol |
| SYMBOL | : | DOL-19 |
| FORMULA | : | C95H156O MOL.WT (average) : 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).
| PHYSICAL AND CHEMICAL PROPERTIES |
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| UV SPECTRA | : | |
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| IR SPECTRA | : | IR spectrum was observed(Ref. 0084). |
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| NMR SPECTRA | : | 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).
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| MASS SPECTRA | : | m/z=1312 (19 isoprene units)(Ref. 0084).
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| OTHER SPECTRA | : |
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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]
| AUTHOR | : | Pennock, J. F., Hemming, F. W., and Morton, R.A. |
| TITLE | : | Dolichol: a naturally occurring isoprenoid alcohol. |
| JOURNAL | : | Nature |
| VOL | : | 186 PAGE : 470 -472 (1960) |
[0021]
| AUTHOR | : | Mankowski, T., Jankowski, W., Chojnacki, T., and Franke, P. |
| TITLE | : | C55-Dolichol: occurrence in pig liver and preparation by hydrogenation of plant undecaprenol PubMed ID:1276128 |
| JOURNAL | : | Biochemistry. |
| VOL | : | 15 PAGE : 2125-2130 (1976) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[0083]
| AUTHOR | : | Singh, H., and Carroll, K. K. |
| TITLE | : | Lipid composition of beef and human pituitary glands PubMed ID:5418196 |
| JOURNAL | : | Lipids. |
| VOL | : | 5 PAGE : 121-127 (1970) |
[0084]
| AUTHOR | : | Carroll, K. K., Vilim, A., and Woods, M. C. |
| TITLE | : | Polyprenols of beef and human pituitary glands PubMed ID:4713373 |
| JOURNAL | : | Lipids. |
| VOL | : | 8 PAGE : 246-248 (1973) |
[0085]
| AUTHOR | : | Knudsen, M. J., and Troy, F. A. |
| TITLE | : | Nuclear magnetic resonance studies of polyisoprenols in model membranes PubMed ID:2611961 |
| JOURNAL | : | Chem Phys Lipids. |
| VOL | : | 51 PAGE : 205-212 (1989) |
Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.
