Identification and biosynthesis of an aggregation pheromone of the storage mite Chortoglyphus arcuatus.
In an effort to identify new pheromones from mites, the headspace of undisturbed colonies of the storage mite Chortoglyphus arcuatus was analyzed by GC-MS by use of a closed-loop stripping apparatus (CLSA) or solid-phase microextraction (SPME). The major compound emitted from the mites is (4R,6R,8R)-4,6,8-trimethyldecan-2-one (4R,6R,8R-8). The structure was elucidated by analysis of the mass spectrum, synthesis of authentic samples, and gas chromatography on a chiral phase. Bioassays show that this compound, for which we propose the trivial name chortolure, is an aggregation pheromone for both sexes of this species. Several related compounds are released in smaller amounts by the mites. The alarm pheromones of these mites, neral and geranial, can only be found in total extracts of the mites, in which 8 occurs only in minute amounts. The method of sampling is therefore crucial for pheromone identification. Feeding experiments with deuterated propionate showed that chortolure is a polyketide, formed by successive addition of four propionate units to an acetate starter.
Schulz
Stefan
S
Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany. stefan.schulz@tu-bs.de
Fuhlendorff
Jens
J
Steidle
Johannes L M
JL
Collatz
Jana
J
Franz
Jörg-Thomas
JT
D040041:Acaridae / Q000737:chemistry*; D000473:Alkanes / Q000737:chemistry / Q000302:isolation & purification; D000818:Animals; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D007659:Ketones / Q000737:chemistry / Q000302:isolation & purification; D008968:Molecular Conformation; D010675:Pheromones / Q000096:biosynthesis* / Q000138:chemical synthesis / Q000737:chemistry*; D013045:Species Specificity
C499504:(4R,6R,8R)-4,6,8-trimethyldecan-2-one; D000473:Alkanes; D007659:Ketones; D010675:Pheromones