Anatoliosides: Five Novel Acyclic Monoterpene Glylcosides from <i>Viburnum orientale</i>

Abstract

Abstract 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 ‐(α‐ L ‐rhamnopyranosyl)β‐ 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 ‐[(2 E ,6 R )‐6‐hydroxy‐2, 6‐dimethylocta‐2,7‐dienoyl]‐(1‴ → 4″)‐ O ‐α‐ L ‐rhamnopyranosyl‐(1″‴ → 2″″)‐β‐ D ‐glucopyranoside ( = anatolioside A; 2 ), linalo‐6‐yl O ‐β‐ D ‐glucopyranosyl‐(1‴ → 6‴)‐ O ‐[(2 E ,6 R )‐6‐hydroxy‐2,6‐dimethylocta‐2,7‐dienoyl]‐(1‴ → 4″)‐ O ‐α‐ L ‐rhamnopyranosyl‐(1″ → 2′)–β‐ D ‐glucopyranoside ( = anatolioside B; 3 ), linalo‐6‐yl O ‐β‐ D ribo ‐hexopyranos‐3‐ulosyl‐(1′‴ → 6‴)‐ O ‐[(2 E ,6 R )‐6‐hydroxy‐2,6‐dimethylocta‐2,7‐dienoyl]‐(1‴ → 4″)‐ O ‐α‐ L ‐rhamnopyranosyl‐(1″ → 2′)‐β‐ D ‐glucopyranoside ( = anatolioside C; 4 ) and linalo‐6‐yl O ‐[(2 E , 6 R )‐6‐hydroxy‐2,6‐dimethylocta‐2,7‐dienoyl]‐(1″‴ → 2″″)‐ O ‐β‐ D ‐glucopyranosly‐(1″″ → 6‴)‐ O ‐[(2 E ,6 R )‐6‐hydroxy‐2,6‐dimethylocta‐2,7‐dienoyl]‐(1‴ → 4″)‐ O ‐α‐ L ‐rhamnopyranosyl(1″ → 2′)‐β‐ D ‐glucopyranoside ( = anatolioside D ; 5 ). The structure determinations were based on spectroscopic and chemical methods (acid and alkaline hydrolysis, acetylation and methylation).