FN Archimer Export Format
PT J
TI 3-Acetoxy-fatty acid isoprenyl esters from androconia of the ithomiine butterfly Ithomia salapia
BT 
AF Mann, Florian
   Szczerbowski, Daiane
   De Silva, Lisa
   McClure, Melanie
   Elias, Marianne
   Schulz, Stefan
AS 1:1;2:1;3:2;4:2,3;5:2;6:1;
FF 1:;2:;3:;4:;5:;6:;
C1 Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
   Institut de Systématique Evolution Biodiversité, Centre National de la Recherche Scientifique, MNHN, Sorbonne Université, EPHE, Université des Antilles, 45 rue Buffon, CP 50, 75005 Paris, France
   Laboratoire Écologie, Évolution, Interactions des Systèmes Amazoniens (LEEISA), Université de Guyane, CNRS, IFREMER, 97300 Cayenne, France
C2 UNIV TECH BRAUNSCHWEIG, GERMANY
   CNRS, FRANCE
   UNIV GUYANE, FRANCE
UM LEEISA
IN WOS Cotutelle UMR
   DOAJ
   copubli-france
   copubli-europe
IF 2.883
TC 7
UR https://archimer.ifremer.fr/doc/00643/75512/76363.pdf
   https://archimer.ifremer.fr/doc/00643/75512/80008.pdf
LA English
DT Article
DE ;fatty acid esters;mass spectrometry;mimicry;pheromones;pyrrolizidine alkaloids
AB 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. 
PY 2020
PD NOV
SO Beilstein Journal Of Organic Chemistry
SN 1860-5397
PU Beilstein Institut
VL 16
UT 000591042900001
BP 2776
EP 2787
DI 10.3762/bjoc.16.228
ID 75512
ER

EF