Identification and electrophysiological activity of a novel hydroxy ketone emitted by male cereal leaf beetles.
Comparisons of collections of volatiles from male and female Oulema melanopus, feeding on host foliage (oats), revealed an electrophysiologically active male-specific compound, (E)-8-hydroxy-6-methyl-6-octen-3-one (7), which is a new natural product. The structure of 7 was elucidated by spectroscopic and microchemical studies and confirmed by chemical synthesis. Antennal electrophysiology showed the sensitive detection of 7 by both sexes, which is consistent with a male-produced aggregation pheromone.
Cossé
Allard A
AA
USDA, Agricultural Research Service, National Center for Agricultural Utilization Research, Crop Bioprotection Research, 1815 N. University Street, Peoria, Illinois 61604, USA. cosseaa@ncaur.usda.gov
Bartelt
Robert J
RJ
Zilkowski
Bruce W
BW
D000818:Animals; D018554:Avena; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D001517:Coleoptera / Q000737:chemistry*; D005260:Female; D006865:Hydrogenation; D007659:Ketones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008297:Male; D015394:Molecular Structure; D009009:Montana; D019906:Nuclear Magnetic Resonance, Biomolecular; D012724:Sex Attractants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology / Q000502:physiology; D013997:Time Factors; D014959:Wyoming
C466359:8-hydroxy-6-methyl-6-octen-3-one; D007659:Ketones; D012724:Sex Attractants