Scent gland constituents of the Middle American burrowing python, <i>Loxocemus bicolor</i> (Serpentes: Loxocemidae)

Schulze, Thies M.; Weldon, Paul J.; Schulz, Stefan

doi:10.1515/znc-2017-0006

Cited by 6 publications

(3 citation statements)

References 33 publications

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“…The location of the double bonds in the unsaturated esters was determined by dimethyl disulfide (DMDS) addition [25,26]. Because the double bond in the isoprenyl side chain would likely interfere, the esters were first transformed into the respective methyl esters via a microreaction with NaOMe [27].…”

Section: Methodsmentioning

confidence: 99%

3-Acetoxy-fatty acid isoprenyl esters from androconia of the ithomiine butterfly Ithomia salapia

Mann¹,

Szczerbowski²,

Silva³

et al. 2020

Beilstein J. Org. Chem.

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Male ithomiine butterflies (Nymphalidae: Danainae) have hairpencils on the forewings (i.e., androconia) that disseminate semiochemicals during courtship. While most ithomiines are known to contain derivatives of pyrrolizidine alkaloids, dihydropyrrolizines, or γ-lactones in these androconia, here we report on a new class of fatty acid esters identified in two subspecies, Ithomia salapia aquinia and I. s. derasa. The major components were identified as isoprenyl (3-methyl-3-butenyl) (Z)-3-acetoxy-11-octadecenoate, isoprenyl (Z)-3-acetoxy-13-octadecenoate (12) and isoprenyl 3-acetoxyoctadecanoate (11) by GC/MS and GC/IR analyses, microderivatizations, and synthesis of representative compounds. The absolute configuration of 12 was determined to be R. The two subspecies differed not only in the composition of the ester bouquet, but also in the composition of more volatile androconial constituents. While some individuals of I. s. aquinia contained ithomiolide A (3), a pyrrolizidine alkaloid derived γ-lactone, I. s. derasa carried the sesquiterpene α-elemol (8) in the androconia. These differences might be important for the reproductive isolation of the two subspecies, in line with previously reported low gene exchange between the two species in regions where they co-occur. Furthermore, the occurrence of positional isomers of unsaturated fatty acid derivatives indicates activity of two different desaturases within these butterflies, Δ9 and Δ11, which has not been reported before in male Lepidoptera.

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Section: Methodsmentioning

confidence: 99%

3-Acetoxy-fatty acid isoprenyl esters from androconia of the ithomiine butterfly Ithomia salapia

Mann¹,

Szczerbowski²,

Silva³

et al. 2020

Beilstein J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…The location of the double bonds in the unsaturated esters was determined by dimethyl disulfide (DMDS) addition [27,28]. Because the double bond in the isoprenyl side chain would likely interfere, the esters were first transformed into the respective methyl esters via a microreaction with NaOMe [29].…”

Section: Resultsmentioning

confidence: 99%

Novel 3-Acetoxy Fatty Acid Isoprenyl Esters from Androconia of the Ithomiine Butterfly Ithomia salapia

Mann¹,

Szczerbowski²,

Silva³

et al. 2020

Preprint

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Male ithomiine butterflies (Nymphalidae: Danainae) have hairpencils on the forewings (i.e. androconia) that disseminate semiochemicals during courtship. While most ithomiines are known to contain derivatives of pyrrolizidine alkaloids, dihydropyrrolizines or g-lactones in these androconia, here we report on a new class of fatty acid esters identified in two subspecies, Ithomia salapia aquinia and I. s. derasa. The major components were identified as isoprenyl (3-methyl-3-butenyl) (Z)-3-acetyloxy-11-octadecenoate, isoprenyl (Z)-3-acetyloxy-13-octadecenoate (12) and isoprenyl 3-acetyloxyoctadecanoate (11) by GC/MS- and GC/IR-analyses, microderivatizations, and synthesis of representative compounds. The absolute configuration of 12 was determined to be R. The two subspecies differed not only in the composition of the ester bouquet, but also in the composition of more volatile androconial constituents. While some individuals of I. s. aquinia contained ithomiolide A, a PA derived g-lactone, I. s. derasa carried the sesquiterpene a-elemol in the androconia. These differences might be important for the reproductive isolation of the two subspecies, in line with previously reported low gene exchange between the two species in regions where they co-occur. Furthermore, the occurrence of positional isomers of unsaturated fatty acid derivatives indicates activity of two different desaturases within these butterflies, D9 and D11, which has not been reported before in male Lepidoptera.

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“…This type of molecule has been observed before in squamate skins and secretions. However, alkane diversity is seldom so pronounced (Jacob et al 1993;Weldon et al 2008;Schulze et al 2017;Baeckens et al 2018). Compounds that have not before been detected in animals, such as 4,5-diethyl-octane, 5-methyl-nonane or potentially currently unidentified molecules, may be ideal candidates for adder-specific pheromones and, therefore, also good indicators of adder presence towards lizards.…”

Section: Discussionmentioning

confidence: 99%

Cracking the chemical code: European common lizards (Zootoca vivipara) respond to an hexane soluble predator kairomone

Moorleghem

Bauwens

Claus

et al. 2020

Biochemical Systematics and Ecology

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Scent gland constituents of the Middle American burrowing python, Loxocemus bicolor (Serpentes: Loxocemidae)

Cited by 6 publications

References 33 publications

3-Acetoxy-fatty acid isoprenyl esters from androconia of the ithomiine butterfly Ithomia salapia

3-Acetoxy-fatty acid isoprenyl esters from androconia of the ithomiine butterfly Ithomia salapia

Novel 3-Acetoxy Fatty Acid Isoprenyl Esters from Androconia of the Ithomiine Butterfly Ithomia salapia

Cracking the chemical code: European common lizards (Zootoca vivipara) respond to an hexane soluble predator kairomone

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