ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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).
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19930760125
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