2014
DOI: 10.1007/s10886-014-0539-5
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Stereoisomeric Analysis of 6,10,14-Trimethylpentadecan-2-ol and the Corresponding Ketone in Wing Extracts from African Bicyclus Butterfly Species

Abstract: Gas chromatography (GC) and mass spectrometry (MS) were used to determine the stereoisomeric compositions of 6,10,14-trimethylpentadecan-2-ol and 6,10,14-trimethylpentadecan-2-one in wing extracts from 17 Bicyclus butterfly species from different regions of Africa. All samples were purified using solid phase extraction (SPE). Since some species contained both alcohol and ketone, these were separated and the ketone was reduced to the alcohol before analysis as either (R)-trans-chrysanthemoyl or (S)-2-acetoxypro… Show more

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Cited by 11 publications
(17 citation statements)
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“…MSP3 is a phytol-derived compound that originates from chlorophyll-a degradation4041. Similar to MSP1, the reduction in MSP3 production in DS males could be controlled by differential regulation of its biosynthetic enzymes.…”
Section: Discussionmentioning
confidence: 99%
“…MSP3 is a phytol-derived compound that originates from chlorophyll-a degradation4041. Similar to MSP1, the reduction in MSP3 production in DS males could be controlled by differential regulation of its biosynthetic enzymes.…”
Section: Discussionmentioning
confidence: 99%
“…Purification of extracts, derivatization, and analysis. GC/MS has been previously used to determine the stereoisomeric composition of TMPD-ol and TMPD-one in wing extracts of Bicyclus butterfly species 10 , stereoisomeric composition of TMPD-one in Euglossa bees 11 and of 3,7-dimethylpentadecan-2-ol in female extracts of pine sawflies 14 , where the stereoisomers of the chiral alcohols were separated as either (R)-trans-chrysanthemoyl or (S)-2-acetoxypropionyl esters. Here we used (S)-2-acetoxypropionyl derivatization method, because it is robust and more suitable for derivatization of compounds present at low concentrations 10,14 .…”
Section: Resultsmentioning
confidence: 99%
“…The synthetic mixture of eight stereoisomers and pure isomers of (2R,6R,10R)-and (2S,6R,10R)-TMPD-ol were utilized for comparisons on GC/MS. The pure isomers were synthesized by Hedenström 10 while working with Euglossa bees and Bicyclus butterflies 10,11 . The eight-stereoisomers mixture of TMPD-ol was synthesized according to Nieberding (supplemental material) 9 .…”
Section: Resultsmentioning
confidence: 99%
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“…The male aphrodisiac pheromones have been reported to be mainly released from secretory cells on the forewing in some species (Hedenstrom et al, 2015;Nieberding et al, 2008;Omura et al, 2001).…”
Section: Introductionmentioning
confidence: 99%