Anatoliosides: Five Novel Acyclic Monoterpene Glylcosides 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‐(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‐[(2E,6R)‐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‐[(2E,6R)‐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‐Dribo‐hexopyranos‐3‐ulosyl‐(1′‴ → 6‴)‐O‐[(2E,6R)‐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‐[(2E, 6R)‐6‐hydroxy‐2,6‐dimethylocta‐2,7‐dienoyl]‐(1″‴ → 2″″)‐O‐β‐D‐glucopyranosly‐(1″″ → 6‴)‐O‐[(2E,6R)‐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).