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

Fingerprint

campesterol
sitosterols
isomerization
Cell culture
cultured cells
Oryza sativa
cell culture
Cell Culture Techniques
Isomerization
Cultured Cells
Cells
Experiments
24-methylenecholesterol
gamma-sitosterol
C 27
Oryza

Keywords

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

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery

Cite this

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. / Nasu, Kozue; Takahashi, Kyoko; Morisaki, Masuo; Fujimoto, Yoshinori.

In: Phytochemistry, Vol. 54, No. 4, 01.06.2000, p. 381-385.

Research output: Contribution to journalArticle

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AU - Nasu, Kozue

AU - Takahashi, Kyoko

AU - Morisaki, Masuo

AU - Fujimoto, Yoshinori

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N2 - 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.

AB - 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.

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KW - Sterol

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