Diversity of sterol composition in the family chenopodiaceae
Department of Biological Sciences
The predominant 4-desmethylsterols from the leaves of 13 species in eight genera of the family Chenopodiaceae are 24α-ethylsterols. In four species, Chenopodium ambrosioides L., C. rubrum L., Salicornia europaea L. and S. bigelovii Torr., the C-22(23) double bond is introduced into more than 70% of the 24α-ethylsterols producing spinasterol (24α-ethylcholesta-7,22E-dien-3β-ol) in the first two species and mixtures of spinasterol and stigmasterol (24α-ethylcholesta-5,22E-dien-3β-ol) in the latter species. The saturated side chain analogues predominate with more than 70% of the 24α-ethylsterols in eight species. Salsola kali L., Suaeda linearis (Ell.) Moq., Kochia scoparia (L.) Roth., and Bassia hirsute (L.) Aschers. synthesize sitosterol (24α-ethylcholest-5-en-3β-ol), and Atriplex arenaria Nutt., C. album L., C. urbicum L. and C. leptophyllum Nutt. possess mixtures of sitosterol and 22-dihydrospinasterol (24α-ethylcholest-7-en-3β-ol). Sitostanol (24α-ethyl-5α-cholestan-3β-ol) was isolated from Suaeda linearis as an 18% component of the total 4-desmethylsterol and in lesser amounts from four other species. In all species synthesizing 24-ethyl-Δ5-sterols, a 24ξ-methylcholest-5-en-3β-ol was also present at 1.0-20% of the total 4-desmethylsterol. Avenasterol [24-ethylcholesta-7,24(28)Z-dien-3β-ol], isofucosterol [24-ethylcholesta-5,24(28)Z-dien-3β-ol), cholesterol (cholest-5-en-3β-ol) and 24ξ-methyl-5α-cholestan-3β-ol also were isolated from several species. Species in the family Chenopodiaceae and the type genus Chenopodium may be categorized into one of three groups based on sterol biosynthesis: the Δ7-sterol producers; the Δ5-sterol producers, and those producing mixtures of both Δ7- and Δ5-sterols in relatively fixed percentage compositions.
Diversity of sterol composition in the family chenopodiaceae.
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