ANATOLIOSIDES - 5 NOVEL ACYCLIC MONOTERPENE GLYCOSIDES FROM VIBURNUM-ORIENTALE

Five new acyclic monoterpene glycosides 1-5 were isolated from the leaves of Viburnum orientale (Caprifoliaceae). Anatolioside (1) is a monoterpene diglycoside and its structure was elucidated as linalo-6-yl 2'-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside (arbitrary numbering of linalool moiety). Compounds 2-5 are all derivatives of 1, containing additional monoterpene and sugar units, connected by ester and glycoside bonds. Their structures were established as linalo-6-yl O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1'''-->4'')-O-alpha-L-rhamnopyranosyl-(1''-->2')-beta-D-glucopyranoside (= anatolioside A; 2), linalo-6-yl O-beta-D-glucopyranosyl-(1''''-->6''')-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1'''-->4'')-O-alpha-L-rhamnopyranosyl-(1''-->2')-beta-D-glucopyranoside (= anatolioside B; 3), linalo-6-yl O-beta-D-ribo-hexopyranos-3-ulosyl-(1''''-->6''')-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1'''-->4'')-O-alpha-L-rhamnopyranosyl-(1''-->2')-beta-D-glucopyranoside (=anatolioside C; 4) and linalo-6-yl O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1''''-->2'''')-O-beta-D-glucopyra-nosyl-(1''''-->6''')-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1'''-->4'')-O-alpha-L-rhamnopyranosyl-(1''-->2')-beta-D-glucopyranoside ( = anatolioside D; 5). The structure determinations were based on spectroscopic and chemical methods (acid and alkaline hydrolysis, acetylation, and methylation).