3-Acetoxy-fatty acid isoprenyl esters from androconia of the ithomiine butterfly Ithomia salapia
| Autor: | Marianne Elias, Melanie McClure, Daiane Szczerbowski, Florian Mann, Stefan Schulz, Lisa de Silva |
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| Přispěvatelé: | Laboratoire Ecologie, Evolution, Interactions des Systèmes amazoniens (LEEISA), Centre National de la Recherche Scientifique (CNRS)-Université de Guyane (UG)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER) |
| Rok vydání: | 2020 |
| Předmět: |
0106 biological sciences
Pyrrolizidine alkaloid Stereochemistry [SDV]Life Sciences [q-bio] fatty acid esters Subspecies Sesquiterpene 010603 evolutionary biology 01 natural sciences Nymphalidae lcsh:QD241-441 Lepidoptera genitalia pyrrolizidine alkaloids 03 medical and health sciences chemistry.chemical_compound lcsh:Organic chemistry lcsh:Science Unsaturated fatty acid mass spectrometry 030304 developmental biology chemistry.chemical_classification 0303 health sciences biology Chemistry Organic Chemistry Fatty acid biology.organism_classification Pyrrolizidine lcsh:Q pheromones mimicry |
| Zdroj: | Beilstein Journal Of Organic Chemistry (1860-5397) (Beilstein Institut), 2020-11, Vol. 16, P. 2776-2787 Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Beilstein-Institut, 2020, 16, pp.2776-2787. ⟨10.3762/bjoc.16.228⟩ Beilstein Journal of Organic Chemistry, Vol 16, Iss 1, Pp 2776-2787 (2020) |
| ISSN: | 1860-5397 |
| DOI: | 10.3762/bjoc.16.228 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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