Sterols of cucurbitaceae: The configurations at C-24 of 24-Alkyl-Δ(5)-,Δ(7)- and Δ(8)-sterols.

Abstract:

:The major sterols of the seeds ofBenincasa cerifera, Cucumis sativus, Cucurbita maxima, C. pepo andTrichosanthes japonica and of the mature plant tissues (leaves and stems) ofCitrullus battich, Cucumis sativus andGynostemma pentaphyllum of the family Cucurbitaceae were 24-ethyl-Δ(7)-sterols which were accompanied by small amounts of saturated and Δ(5)-and Δ(8)-sterols. The 24-ethyl-Δ(7,22),Δ(7,25(27)) and Δ(7,22,25(27))-sterols constituted the predominant sterols for the seed materials, whereas the 24-ethyl-Δ(7) and Δ(7,22)-sterols were the major ones for the mature plant tissues. The configurations of C-24 of the alkylsterols were examined by high resolution(1)H NMR and(13)C NMR spectroscopy. Most of the 24-methyl- and 24-ethylsterols examined which lack a Δ(25(27))-bond (i.e., 24-methyl-, 24-methyl-Δ(22)-, 24-ethyl- and 24-ethyl-Δ(22) sterols) were shown to occur as the C-24 epimeric mixtures in which the 24α-epimers predominated in most cases. The 24-ethylsterols which possess a Δ(25(27)) (i.e., 24-ethyl-Δ(25(27))-and 24-ethyl-Δ(7,22,25(27))-sterols) were, on the other hand, composed of only 24β-epimers. The Δ(8)-sterols identified and characterized were four 24-ethyl-sterols: 24α-and 24β-ethyl-5α-cholesta-8,22-dien-3β-ol, 24β-ethyl-5α-cholesta-8,25(27)-dien-3β-ol and 24β-ethyl-5α-cholesta-8,22,25(27)-trien-3β-ol. This seems to be the first case of the detection of Δ(8)-sterols lacking a 4-methyl group in higher plants, and among the four Δ(8)-sterols the latter two are considered to be new sterols. The probable biogenetic role of the Δ(8)-sterols and the possible biosynthetic pathways leading to the 24α- and 24β-alkylsterols in Cucurbitaceae are discussed.

journal_name

Lipids

journal_title

Lipids

authors

Akihisa T,Thakur S,Rosenstein FU,Matsumoto T

doi

10.1007/BF02534301

subject

Has Abstract

pub_date

1986-01-01 00:00:00

pages

39-47

issue

1

eissn

0024-4201

issn

1558-9307

pii

10.1007/BF02534301

journal_volume

21

pub_type

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