Elsevier

Steroids

Volume 53, Issues 3–5, March–May 1989, Pages 625-638
Steroids

Sterols of some Clerodendrum species (verbenaceae): Occurrence of the 24α- and 24β-epimers of 24-ethylsterols lacking a Δ25-bond

https://doi.org/10.1016/0039-128X(89)90036-6Get rights and content

Abstract

The configurations at C-24 of 24-alkylsterols of six samples of Clerodendrum species (Verbenaceae) — the aerial parts of C.fragrans,C. inerme, C. infortunatum, C. scandens, and C. sipho-nanthus, and the seeds of C. infortunatum — were examined by NMR. All samples contained 24β-ethylsterols possessing a Δ25 -bond, clerosterol and 22-dehydroclerosterol, as the dominant sterol components. The other 24-ethylsterols lacking a Δ25 -bond, 24-ethyl-22-dehydrocholestanol, 24-ethylcholesterol, and 24-ethyl-22-dehydrocholesterol, which were present as minor components, were shown to be mixtures of the 24α- and 24β-epimers, with the 24α-epimers predominating in all cases. Four minor 24-methyl-sterols, 24-methylcholestanol, 24-methylcholesterol, 24-methyl-22-dehydrocholesterol, and 24-methyllathosterol, were shown to be C-24 epimeric mixtures, whereas two others, 24-methyl-22, 25-bis-dehydrocholesterol and 24-methyl-22-dehydrolathosterol, were found to be present only as the 24β-epimers. This is the first report of the occurrence of 24β-ethyl-22-dehydrocholestanol in higher plants.

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