Cyclic fatty acyl glycosides in the glandular trichome exudate of Silene gallica.
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-beta-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.
Asai
Teigo
T
Department of Chemistry and Materials Science, Tokyo Institute of Technology, Meguro, Tokyo 152-8551, Japan.
Fujimoto
Yoshinori
Y
D005227:Fatty Acids / Q000737:chemistry / Q000302:isolation & purification*; D006017:Glycolipids / Q000737:chemistry / Q000302:isolation & purification*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D053147:Plant Exudates / Q000737:chemistry; D029751:Silene / Q000737:chemistry*
D005227:Fatty Acids; D006017:Glycolipids; D006027:Glycosides; D053147:Plant Exudates