| 1. |
- Anderbrant, O., et al.
(author)
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Electrophysiological and morphological characteristics of pheromone receptors in male pine sawflies, Diprion pini (Hymenoptera : Diprionidae), and behavioural response to some compounds
- 1995
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In: Journal of Insect Physiology. - : Elsevier BV. - 0022-1910. ; 41:5, s. 395-401
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Journal article (peer-reviewed)abstract
- The morphology and physiology of pheromone receptors on the antennae of male pine sawflies, Diprion pini L., were investigated. Using scanning electron microscopy, five sensillar types were recognized. The type shown to be pheromone sensitive has a long (50-70 μm) cuticular hair, is single-walled, and is innervated by 8 or 9 sensory cells as revealed by transmission electron microscopy. Electroantennography (EAG) showed similar activity of the acetate and propionate of (2S,3R,7R)-3,7-dimethyl-2-tridecanol, precursor of the main constituent of the female-produced sex pheromone. No other isomer induced any significant response. Single-sensillum recordings confirmed the results of the EAG, and also showed that several neurons were excited by the active compound. EAG recordings and combined gas chromatographic-electroantennographic detection indicated that esters of three 3,7-dimethyl-2-pentadecanol (diprionol) isomers were active, but field tests could not demonstrate any behavioural effect. Diprionol esters are used as sex pheromones by all other pine sawflies investigated so far, and D. pini is thus the first diprionid species shown to use a different sex pheromone.
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| 3. |
- Högberg, Hans-Erik, et al.
(author)
-
Biocatalysis as a useful tool in pheromone synthesis. Enantiomerically pure building blocks from baker's yeast reductions and enzyme catalysed resoluti
- 1994
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In: Catalysis Today. - : Elsevier BV. - 0920-5861. ; 22:3, s. 591-606
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Journal article (peer-reviewed)abstract
- Biocatalytical methods are presented which provide useful building blocks for pheromone synthesis. Examples of the utility of this approach are the preparation of building blocks for the synthesis of stereochemically pure isomers of pine sawfly pheromones and some other pheromones. Enantiom- erically pure ( 98% ee) 2-methyl-1-alkanols 2 were obtained via baker's yeast reduction of suitable α,β-unsaturated aldehydes, and by using lipases from Pseudomonas to effect resolution by transesterification of suitable racemic precursors to 2-methyl-1-alkanols 2 which gave high enantiomeric ratios E > 100. The resolution by esterification mediated by lipase from Candida rugosa of racemic 2-methylalkanoic acids also gave high enantiomeric ratios E> 100 after having improved the reaction conditions by regulating water activity, by choice of the appropriate complimentary substrate alcohol and by adjusting the initial equivalents of the latter present at the start. Also discussed is the separation of diastereomers of diprionol 1, which is naturally occurring in the pine sawfly Neodiprion sertifer, where it is the direct precursor of its pheromone.
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