Cyclic glycolipids from glandular trichome exudates of Cerastium glomeratum

Teigo Asai, Yuki Nakamura, Yui Hirayama, Kiyoshi Ohyama, Yoshinori Fujimoto

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Fourteen cyclic glycolipids, named glomerasides A-N, have been isolated from the glandular trichome exudate of Cerastium glomeratum (Caryophyllaceae). Their structures were determined by spectroscopic analysis of the glycolipids, as well as by application of the Ohrui-Akasaka method to the fatty acid methyl esters derived from the glycolipids and GCMS studies of trimethylsilyl ether derivatives of the methyl esters. The various glomerasides have a glycosidic linkage between the anomeric hydroxy group of the glucose and the C-11, C-10 or C-9 positions of the docosanoyl moiety. They also contained an ester linkage between the C-6 hydroxy group of the glucose ring and the carboxyl group of the oxygenated fatty acid to form their macrocyclic structures. The glucose moiety was optionally acetylated and/or malonylated at the C-2 or C-3 hydroxy groups. Among these compounds, the 1,6′-cyclic ester of 11(R)-(2-O-acetyl-β- d-glucopyranosyloxy)docosanoic acid (glomeraside D) was the most abundant (25%).

Original languageEnglish
Pages (from-to)149-157
Number of pages9
JournalPhytochemistry
Volume82
DOIs
Publication statusPublished - 2012 Oct 1
Externally publishedYes

Keywords

  • Caryophyllaceae
  • Cerastium glomeratum
  • Cyclic glycolipid
  • Glandular trichome
  • Ohrui-Akasaka method

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

Fingerprint Dive into the research topics of 'Cyclic glycolipids from glandular trichome exudates of Cerastium glomeratum'. Together they form a unique fingerprint.

  • Cite this