Phytochemistry p. 1057 - 1064 (1996)
Update date:2022-08-29
Topics:
Yagi, Tomoko
Morisaki, Masuo
Kushiro, Tetsuo
Yoshida, Hiroko
Fujimoto, Yoshinori
A hairy root culture of Ajuga reptans var. atropurpurea contains clerosterol, 22-dehydroclerosterol and cholesterol as its sterol constituents. Feeding of [26-, 27-13C2]desmosterol to this culture and 13C NMR analysis of the resulting biosynthesized sterols showed that the substrate was efficiently incorporated into clerosterol and codisterol. Feeding of [26-13C] and [27-13C]desmosterols revealed that the C-24 alkylation takes place in a highly specific manner wherein the 26- and 27-methyl groups of the substrate becomes C-26 (vinyl methyl) and C-27 (exomethylene carbon), respectively, of the two Δ25-sterols. Further, feeding of [24-2H]desmosterol and 2H NMR analysis of the products showed that H-24 of clerosterol and codisterol is derived from H-24 of desmosterol. Finally, [28-13C]ergosta-5,24(28)-dien-3β-ol was shown to be converted into clerosterol and 22-dehydroclerosterol, but not into codisterol. On the basis of these data, possible biosynthetic mechanism of 24β-alkyl-Δ25-sterols in this plant is proposed. Copyright
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