Stereochemical fate of C-26 and C-27 during the conversion of isofucosterol to sitosterol and of 24-methylenecholesterol to campesterol and dihydrobrassicasterol in Oryza sativa cell cultures

Kozue Nasu, Kyoko Takahashi, Masuo Morisaki, Yoshinori Fujimoto

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Administration of pro-R-methyl-13C-labeled isofucosterol to cultured cells of Oryza sativa revealed that the pro-R and pro-S methyls at C-25 become the pro-R and pro-S methyls at C-25 of sitosterol, respectively. Similar administration experiments using pro-S-methyl-13C-labeled 24- methylenecholesterol established that the pro-R and pro-S methyls at C-25 of 24-methylenecholesterol become the pro-R and pro-S methyls of campesterol, and the pro-S and pro-R methyls of dihydrobrassicasterol, respectively. These results are compatible with our recently proposed 'syn-S(E)2' mechanism' for double bond isomerization of Δ(24(28)) into Δ(24(25)). (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)381-385
Number of pages5
JournalPhytochemistry
Volume54
Issue number4
DOIs
Publication statusPublished - 2000 Jun 1

Keywords

  • 24- Ethyldesmosterol
  • 24-Methyldesmosterol
  • Biosynthesis
  • Gramineace
  • Isofucosterol
  • Oryza sativa
  • Sitosterol
  • Sterol

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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