title: Cyclic glycolipids from glandular trichome exudates of Cerastium glomeratum.
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%).
authors.affiliation: Department of Chemistry and Materials Science, Tokyo Institute of Technology, Meguro, Tokyo, Japan.
authors.forename: Teigo
authors.initials: T
authors.lastname: Asai
authors.forename: Yuki
authors.initials: Y
authors.lastname: Nakamura
authors.forename: Yui
authors.initials: Y
authors.lastname: Hirayama
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Ohyama
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Fujimoto
mesh_terms: D029748:Caryophyllaceae / Q000737:chemistry* / Q000378:metabolism; D006017:Glycolipids / Q000737:chemistry* / Q000302:isolation & purification* / Q000378:metabolism; D007850:Lauric Acids / Q000737:chemistry
chemical_list: D006017:Glycolipids; D007850:Lauric Acids; C030358:lauric acid