Dominance of Δ7-sterols in the family caryophyllaceaein the family caryophyllaceae

Abstract

The predominant 4-desmethylsterols from the leaves of 12 species in 11 genera of the family Caryophyllaceae are 24-ethyl-Δ7-sterols. In eight species, Scleranthus annus L., Paronychia virginica Spreng., Lychnis alba Mill., Silene cucubalus Wibel, Dianthus armeria L., Gypsophilia paniculata L., Saponaria officinales L. and Myosoton aquaticum (L.) Moench, the major sterols are spinasterol (24α-ethylcholesta-7,22E-dien-3β-ol) and 22-dihydrospinasterol (24α-ethylcholest-7-en-3β-ol), with spinasterol at more than 60% of the desmethylsterol in the latter six species. Both 24α-and 24β-ethyl-Δ7-sterols are present in two species, Minuartia caroliniana Walt. and Spergula arvensis L., which possess 24β-ethylcholesta-7,25(27)-dien-3β-ol and 24β-ethylcholesta-7,22E,25(27)-trien-3β-ol as well as spinasterol and 22-dihydrospinasterol. Cerastium arvense L., C. vulgatum L. and Arenaria serpyllifolia L. possess 24-alkyl-Δ5 and Δ7-sterols. These three species synthesize sitosterol (24α-ethylcholest-5-en-3β-ol), 24ζ-methylcholest-5-en-3β-ol, spinasterol, 22-dihydrospinasterol and the stanols, sitostanol (24α-ethyl-5α-cholestan-3β-ol) and 24ζ-methyl-5α-cholestan-3β-ol. Avenasterol (24-ethylcholesta-7,24(28)Z-dien-3β-ol) was also isolated from five species. Sterol biosynthetic capability may be a useful characteristic in examining the taxonomic relatedness of plants in the Caryophyllaceae. © 1986 American Oil Chemists' Society.