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. 1974 Feb;53(2):244–249. doi: 10.1104/pp.53.2.244

Inhibition of Sterol Biosynthesis in Chlorella sorokiniana by Triparanol 1

Jarvis T Chan a, Glenn W Patterson a, Samson R Dutky b, Charles F Cohen b
PMCID: PMC541372  PMID: 16658684

Abstract

When Chlorella sorokiniana was cultured in the presence of 1 mg/1 triparanol succinate, there was a 42% reduction in total sterol concentration. Algal biomass was reduced by approximately the same amount. In addition to the cycloartenol, cyclolaudenol, 24-methyl-pollinastanol, ergosta-5, 7-dien-3β-ol, and ergosterol that occur in control culture, pollinastanol, 14α-methyl-5α-ergost-8-en-3β-ol, 5α-ergosta-8, 14, 22-trien-3β-ol, 5α-ergosta-8(14), 22-dien-3β-ol, 5α-ergosta-8(9), 22-dien-3β-ol, 5α-ergosta-8, 14-dien-3β-ol, 5α-ergost-8(9)-3n-3β-ol, 5α-ergost-8(14)-en-3β-ol, 5α-ergosta-7, 22-dien-3β-ol, and 5α-ergost-7-en-3β-ol were isolated and identified from triparanol succinate-treated cells. A biosynthetic pathway for sterol biosynthesis in this organism is postulated based on all the sterols that were isolated and identified in triparanol-treated cultures of C. sorokiniana. Cyclolaudenol appears to be the product of the first alkylation at C-24 in this organism rather than the more common 24-methylene cycloartanol. Since 24-methylene sterols are needed for the second alkylation reaction, this would explain the absence of C-29 sterols in C. sorokiniana. Four of the sterols identified in C. sorokiniana are reported for the first time in a living organism. They are: 24-methyl pollinastanol, 5α-ergosta-8, 14, 22-trien-3β-ol, 5α-ergosta-8(14), 22-dien-3β-ol and 5α-ergost-8(14)-en-3β-ol.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. AARONSON S., BENSKY B., SHIFRINE M., BAKER H. Effect of hypocholesteremic agents on protozoa. Proc Soc Exp Biol Med. 1962 Jan;109:130–132. doi: 10.3181/00379727-109-27125. [DOI] [PubMed] [Google Scholar]
  2. AVIGAN J., STEINBERG D., VROMAN H. E., THOMPSON M. J., MOSETTIG E. Studies of cholesterol biosynthesis. I. The identification of desmosterol in serum and tissues of animals and man treated with MER-29. J Biol Chem. 1960 Nov;235:3123–3126. [PubMed] [Google Scholar]
  3. Aaronson S., Roze U., Keane M., Zahalsky A. C. [Inhibition of Ochromonas respiration by hypocholesteremic compounds and its annulment by unsaturated fatty acids]. J Protozool. 1969 Feb;16(1):184–186. doi: 10.1111/j.1550-7408.1969.tb02253.x. [DOI] [PubMed] [Google Scholar]
  4. BLOHM T. R., MACKENZIE R. D. Specific inhibition of cholesterol biosynthesis by a synthetic compound (MER-29). Arch Biochem Biophys. 1959 Nov;85:245–249. doi: 10.1016/0003-9861(59)90467-9. [DOI] [PubMed] [Google Scholar]
  5. Barton D. H., Harrison D. M., Moss G. P., Widdowson D. A. Investigations on the biosynthesis of steroids and terpenoids. II. Role of 24-methylene derivatives in the biosynthesis of steroids and terpenoids. J Chem Soc Perkin 1. 1970;6:773–785. [PubMed] [Google Scholar]
  6. Chan J. T., Patterson G. W. Triparanol Inhibition of Sterol Biosynthesis in Chlorella ellipsoidea. Plant Physiol. 1973 Sep;52(3):246–247. doi: 10.1104/pp.52.3.246. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Fried J., Dudowitz A., Brown J. W. Enzymatic conversion of 32-oxygenated delta-7-lanosterol derivatives and of delta-8(14)-4,4-dimethyl-cholestenol to cholesterol. Biochem Biophys Res Commun. 1968 Aug 13;32(3):568–574. doi: 10.1016/0006-291x(68)90701-8. [DOI] [PubMed] [Google Scholar]
  8. Lee W. H., Kammereck R., Lutsky B. N., McCloskey J. A., Schroepfer G. J. Studies on the mechanism of the enzymatic conversion of delta 8-cholesten-3 beta-ol to delta 7-cholesten-3 beta-ol. J Biol Chem. 1969 Apr 25;244(8):2033–2040. [PubMed] [Google Scholar]
  9. Lutsky B. N., Schroepfer G. J., Jr Isolation of delta-8-(14)-cholesten-3-beta-o1 from rat skin. Biochem Biophys Res Commun. 1969 Apr 29;35(2):288–293. doi: 10.1016/0006-291x(69)90280-0. [DOI] [PubMed] [Google Scholar]
  10. Lutsky B. N., Schroepfer G. J., Jr Studies on the enzymatic conversion of 5 alpha-cholesta-8, 14-dien-3 beta-ol to cholesterol. J Biol Chem. 1970 Dec 10;245(23):6449–6455. [PubMed] [Google Scholar]
  11. Orcutt D. M., Richardson B. Sterols of Oocystis polymorpha, a green alga. Steroids. 1970 Oct;16(4):429–446. doi: 10.1016/s0039-128x(70)80125-8. [DOI] [PubMed] [Google Scholar]
  12. Parks L. W., Bond F. T., Thompson E. D., Starr P. R. 8(9),22 -Ergostadiene-3 -ol, an ergosterol precursor accumulated in wild-type and mutants of yeast. J Lipid Res. 1972 May;13(3):311–316. [PubMed] [Google Scholar]
  13. Patterson G. W. Sterols of Chlorella. II. The Occurrence of an Unusual Sterol Mixture in Chlorella vulgaris. Plant Physiol. 1967 Oct;42(10):1457–1459. doi: 10.1104/pp.42.10.1457. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Schroepfer G. J., Jr, Lutsky B. N., Martin J. A., Huntoon S., Fourcans B., Lee W. H., Vermilion J. Recent investigations on the nature of sterol intermediates in the biosynthesis of cholesterol. Proc R Soc Lond B Biol Sci. 1972 Feb 15;180(1059):125–146. [PubMed] [Google Scholar]
  15. Schroepfer G. J., Jr, Lutsky B. N., Martin J. A., Huntoon S., Fourcans B., Lee W. H., Vermillion J. Recent investigations on the nature of sterol intermediates in the biosynthesis of cholesterol. Proc R Soc Lond B Biol Sci. 1972 Feb 15;180(1059):125–146. [PubMed] [Google Scholar]
  16. Vroman H. E., Cohen C. F. Separation of sterol acetates by column and thin-layer argentation chromatography. J Lipid Res. 1967 Mar;8(2):150–152. [PubMed] [Google Scholar]

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