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Absolute Configurations of Zingiberenols Isolated from Ginger (Zingiber officinale) Rhizomes

Author:
Khrimian, Ashot, Shirali, Shyam, Guzman, Filadelfo
Source:
Journal of natural products 2015 v.78 no.12 pp. 3071-3074
ISSN:
1520-6025
Subject:
Oebalus poecilus, Oebalus pugnax, Zingiber officinale, gas chromatography, ginger, rhizomes, sex pheromones, stereoisomers
Abstract:
Two stereoisomeric zingiberenols in ginger were identified as (3R,6R,7S)-1,10-bisaboladien-3-ol (2) and (3S,6R,7S)-1,10-bisaboladien-3-ol (5). Absolute configurations were assigned by utilizing 1,10-bisaboladien-3-ol stereoisomers and two gas-chromatography columns: a 25 m Hydrodex-β-6TBDM and 60 m DB-5MS. The C-6 and C-7 absolute configurations in both zingiberenols match those of zingiberene present abundantly in ginger rhizomes. Interestingly, zingiberenol 2 has recently been identified as a male-produced sex pheromone of the rice stink bug, Oebalus poecilus, thus indicating that ginger plants may be a potential source of the sex pheromone of this bug.
Agid:
5494623