Cyclic fatty acyl glycosides in the glandular trichome exudate of Silene gallica

Teigo Asai, Yoshinori Fujimoto

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

Chemical investigation of the glandular trichome exudate from Silene gallica L. (Caryophyllaceae) resulted in isolation of 10 cyclic fatty acyl glycosides (gallicasides A-J). The cyclic structures were characterized by a glycosidic linkage of the glucose moiety to either the C-12 or the C-13 position of the octadecanoyl moiety, and by an ester linkage between the C-2 hydroxy group of the glucose moiety and the carboxyl group of the oxygenated octadecanoic acid. The structures of the cyclic fatty acyl glycosides were further distinguished from one another by acetylation and/or malonylation on the glucose moiety. Of these compounds, the 1,2′-cyclic ester of 12(R)-(6-O-acetyl-3-O-malonyl-β-d-glucopyranosyloxy)octadecanoic acid (gallicaside J) was the most abundant (30.7%). These secondary metabolites were found specifically in the glandular trichome exudate rather than in other aerial parts.

Original languageEnglish
Pages (from-to)1410-1417
Number of pages8
JournalPhytochemistry
Volume71
Issue number11-12
DOIs
Publication statusPublished - 2010 Aug 1
Externally publishedYes

Keywords

  • Caryophyllaceae
  • Glandular trichome
  • Glycolipid
  • Glycosylated fatty acid
  • Silene gallica

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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