| Title: | Absolute Configurations of Zingiberenols Isolated from Ginger (Zingiber officinale) Rhizomes |
| Author(s): | Khrimian A; Shirali S; Guzman F; |
| Address: | "Invasive Insect Biocontrol and Behavior Laboratory, U.S. Department of Agriculture, Agricultural Research Service , Northeast Area, Bldg 007, Rm 301, BARC-West, 10300 Baltimore Avenue, Beltsville, Maryland 20705, United States" |
| DOI: | 10.1021/acs.jnatprod.5b00638 |
| ISSN/ISBN: | 1520-6025 (Electronic) 0163-3864 (Linking) |
| 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-beta-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" |
| Keywords: | "Animals Gas Chromatography-Mass Spectrometry Ginger/*chemistry Heteroptera/drug effects/metabolism Male Molecular Structure Monocyclic Sesquiterpenes Oils, Volatile Pheromones/chemistry/*isolation & purification/pharmacology Rhizome/*chemistry Sesquiterpe;" |
| Notes: | "MedlineKhrimian, Ashot Shirali, Shyam Guzman, Filadelfo eng Research Support, U.S. Gov't, Non-P.H.S. 2015/11/26 J Nat Prod. 2015 Dec 24; 78(12):3071-4. doi: 10.1021/acs.jnatprod.5b00638. Epub 2015 Nov 25" |
