Metabolic conversion of 24-methyl-Δ25-cholesterol to 24-methylcholesterol in higher plants

Kyoko Takahashi; Kozue Nasu; Tadahiko Mashino; Masuo Morisaki; Noriyuki Hara; Yoshinori Fujimoto

doi:10.1016/j.bmc.2005.08.061

Metabolic conversion of 24-methyl-Δ²⁵-cholesterol to 24-methylcholesterol in higher plants

Kyoko Takahashi, Kozue Nasu, Tadahiko Mashino, Masuo Morisaki, Noriyuki Hara, Yoshinori Fujimoto

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

Feeding of chemically synthesized [27-¹³C]codisterol ([27- ¹³C]2), [27-¹³C]24-epicodisterol ([27-¹³C]3), [23,24-²H₂]codisterol ([23,24-²H ₂]2), and [26,27-²H₆]24-methyldesmosterol ([26,27-²H₆]8) to Oryza sativa cell cultures, followed by MS and NMR analysis of the biosynthesized dihydrobrassicasterol (9)/campesterol (10), revealed that both (24R)- and (24S)-epimers of 24-methyl- Δ²⁵-cholesterol (2/3) were converted to 9 and 10 via the common intermediate 24-methyldesmosterol (8).

Original language	English
Pages (from-to)	732-738
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	14
Issue number	3
DOIs	https://doi.org/10.1016/j.bmc.2005.08.061
Publication status	Published - 2006 Feb 1

Keywords

Biosynthesis
Campesterol
Codisterol
Dihydrobrassicasterol
Oryza sativa
Steroids and sterols

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Access to Document

10.1016/j.bmc.2005.08.061

Cite this

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title = "Metabolic conversion of 24-methyl-Δ25-cholesterol to 24-methylcholesterol in higher plants",

abstract = "Feeding of chemically synthesized [27-13C]codisterol ([27- 13C]2), [27-13C]24-epicodisterol ([27-13C]3), [23,24-2H2]codisterol ([23,24-2H 2]2), and [26,27-2H6]24-methyldesmosterol ([26,27-2H6]8) to Oryza sativa cell cultures, followed by MS and NMR analysis of the biosynthesized dihydrobrassicasterol (9)/campesterol (10), revealed that both (24R)- and (24S)-epimers of 24-methyl- Δ25-cholesterol (2/3) were converted to 9 and 10 via the common intermediate 24-methyldesmosterol (8).",

keywords = "Biosynthesis, Campesterol, Codisterol, Dihydrobrassicasterol, Oryza sativa, Steroids and sterols",

author = "Kyoko Takahashi and Kozue Nasu and Tadahiko Mashino and Masuo Morisaki and Noriyuki Hara and Yoshinori Fujimoto",

year = "2006",

month = feb,

day = "1",

doi = "10.1016/j.bmc.2005.08.061",

language = "English",

volume = "14",

pages = "732--738",

journal = "Bioorganic and Medicinal Chemistry",

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T1 - Metabolic conversion of 24-methyl-Δ25-cholesterol to 24-methylcholesterol in higher plants

AU - Takahashi, Kyoko

AU - Nasu, Kozue

AU - Mashino, Tadahiko

AU - Morisaki, Masuo

AU - Hara, Noriyuki

AU - Fujimoto, Yoshinori

PY - 2006/2/1

Y1 - 2006/2/1

N2 - Feeding of chemically synthesized [27-13C]codisterol ([27- 13C]2), [27-13C]24-epicodisterol ([27-13C]3), [23,24-2H2]codisterol ([23,24-2H 2]2), and [26,27-2H6]24-methyldesmosterol ([26,27-2H6]8) to Oryza sativa cell cultures, followed by MS and NMR analysis of the biosynthesized dihydrobrassicasterol (9)/campesterol (10), revealed that both (24R)- and (24S)-epimers of 24-methyl- Δ25-cholesterol (2/3) were converted to 9 and 10 via the common intermediate 24-methyldesmosterol (8).

AB - Feeding of chemically synthesized [27-13C]codisterol ([27- 13C]2), [27-13C]24-epicodisterol ([27-13C]3), [23,24-2H2]codisterol ([23,24-2H 2]2), and [26,27-2H6]24-methyldesmosterol ([26,27-2H6]8) to Oryza sativa cell cultures, followed by MS and NMR analysis of the biosynthesized dihydrobrassicasterol (9)/campesterol (10), revealed that both (24R)- and (24S)-epimers of 24-methyl- Δ25-cholesterol (2/3) were converted to 9 and 10 via the common intermediate 24-methyldesmosterol (8).

KW - Biosynthesis

KW - Campesterol

KW - Codisterol

KW - Dihydrobrassicasterol

KW - Oryza sativa

KW - Steroids and sterols

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