Abstract
We identified two aliphatic formates, (Z,Z)-8,11-heptadecadienyl formate and (Z)-8-heptadecenyl formate in the opisthonotal gland secretions of an unidentified acarid species, namely Sancassania sp. Sasagawa. Both compounds were isolated using silica gel column chromatography and the structures were elucidated by 1H-NMR and GC/FT-IR. Further information on the double bond positions was obtained by GC-MS analysis of the corresponding dimethyl disulfide derivatives. Based on the estimated structures of the two formates and using linoleic and oleic acids as the respective starting materials, a simple four-step synthesis was achieved via Barton decarboxylation as the key step. The aliphatic formates identified in acarids thus far are neryl formate ((Z)-3,7-dimethylocta-2,6-dienyl formate) and lardolure (1,3,5,7-tetramethyldecyl formate), and both have been reported to have pheromone functions. The biological function of the two formates isolated in this study is currently being investigated. Although we can speculate that the two compounds were biosynthesized from linoleic and oleic acid, there is a possibility that the synthetic processes featured a novel chain shortening and formic acid esterification mechanism.
Highlights
All hydrocarbons observed in the opisthonotal gland secretions of acarid mites are straight-chain aliphatic compounds, and the chains are characteristically shorter than those of the hydrocarbons found in insects [1]
Wasasthe alarm pheromone discovered in acarids [4]konoi and was understood present aggregation activation intypes otherofacarid mites such(1,3,5,7-tetramethyldecyl as C. lactis, Aleuroglyphus found to to function as an alarm pheromone in many mites [1]
It can be surmised from the double-bond positions that formate 1 is biosynthesized from linoleic acid (LA), while compound 2 comes from oleic acid (OA)
Summary
All hydrocarbons observed in the opisthonotal gland secretions of acarid mites are straight-chain aliphatic compounds, and the chains are characteristically shorter than those of the hydrocarbons found in insects [1]. Neryl formate ((Z)-3,7-dimethylocta-2,6-dienyl formate) and lardolure are aliphatic chain formates labeled compound uptake experiments using Carpoglyphus lactis, the biosynthetic conversion of LA foundtoin acarids. Lactis, Aleuroglyphus ovatus, side chain and is formed through the step-wise coupling of propionyl CoA with four molecules of and Tyrophagus putrescentiae [5,6,7]. Two aliphatic formate compounds have been detected in the secretions of the unidentified methylmalonyl CoA molecules and the subsequent formation of the formate remains unknown. Two formateWhile compounds beenare detected in the to secretions of the unidentified straight-chain acids and OA, as lardolure, carbon-chain shortening. This study reports the structure straight-chain unsaturated fatty acids LA and OA, as with lardolure, the carbon-chain shortening mechanismand andefficient formationsynthetic of the formate ester requirefor confirmation. Determination and efficient synthetic methodologies for preparing these two compounds
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