title: Absolute Configurations of Zingiberenols Isolated from Ginger (Zingiber officinale) Rhizomes.
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.
authors.affiliation: 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.
authors.forename: Ashot
authors.initials: A
authors.lastname: Khrimian
authors.affiliation: 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.
authors.forename: Shyam
authors.initials: S
authors.lastname: Shirali
authors.affiliation: 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.
authors.forename: Filadelfo
authors.initials: F
authors.lastname: Guzman
mesh_terms: D000818:Animals; D008401:Gas Chromatography-Mass Spectrometry; D020939:Zingiber officinale / Q000737:chemistry*; D020062:Heteroptera / Q000187:drug effects / Q000378:metabolism; D008297:Male; D015394:Molecular Structure; D000081222:Monocyclic Sesquiterpenes; D009822:Oils, Volatile; D010675:Pheromones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D027343:Rhizome / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification*; D013237:Stereoisomerism
chemical_list: D000081222:Monocyclic Sesquiterpenes; D009822:Oils, Volatile; D010675:Pheromones; D012717:Sesquiterpenes; C477983:zingiberene