GC/FT-IR Analysis of Novel 4,6,9-Triene and 2,4,6,9-Tetraene Occurring in a Female Pheromone Gland of Arctia plantaginis (Erebidae: Arctiinae)
Muraki, Y., Yamakawa, R., Yamamoto, M., Naka, H., Honma, A., Mappes, J., Suisto, K., & Ando, T. (2017). GC/FT-IR Analysis of Novel 4,6,9-Triene and 2,4,6,9-Tetraene Occurring in a Female Pheromone Gland of Arctia plantaginis (Erebidae: Arctiinae). American Journal of Analytical Chemistry, 8(10), Article 79871. https://doi.org/10.4236/ajac.2017.810047
Julkaistu sarjassa
American Journal of Analytical ChemistryTekijät
Päivämäärä
2017Oppiaine
Ekologia ja evoluutiobiologiaEvoluutiotutkimus (huippuyksikkö)Ecology and Evolutionary BiologyCentre of Excellence in Evolutionary ResearchTekijänoikeudet
© 2017 by Authors and Scientific Research Publishing Inc. This work is licensed under the Creative Commons Attribution International License (CC BY 4.0).
Fifteen subspecies of the wood tiger moth, Arctia plantaginis (Lepidoptera:
Erebidae: Arctiinae), have been recorded in the Northern Hemisphere. An
analysis of crude pheromone extracts by GC equipped with an electroantennographic
(EAG) detector showed four EAG-active components (Comps.
I–IV) that were commonly involved in the pheromone glands of two subspecies
inhabiting Japan and Finland. Comp. I is a major component (>75%) and
the others are minor components (3% - 15%). Their mass spectra, measured
by GC/MS, revealed the chemical structures of C21 unsaturated hydrocarbons
as follows: 3,6,9-triene for Comp. I, 4,6,9-triene for Comp. II, 1,3,6,9-tetraene
for Comp. III, and 2,4,6,9-tetraene for Comp. IV. Comps. I and III are known
Type II pheromone compounds, and their retention times coincide with those
of the authentic standards with all Z configurations. As a next step, the extract
was analyzed by GC/FT-IR to determine the configuration of Comps. II and
IV. Their IR spectra showed two characteristic C-H bending absorptions
around 990 and 945 cm−1 due to the conjugated dienyl moieties; thus, Z and E
configurations were assigned to the double bonds at the 2- and 4-positions,
respectively. Their Z double bonds at the 6- and 9-positions are indicated by
no absorptions around 970 cm−1
, due to the isolated double bonds with E configurations.
Finally, the structures of Comps. II and IV were confirmed by
synthesis using a double Wittig reaction. The synthetic (4E,6Z,9Z)-4,6,9-triene
and (2Z,4E,6Z,9Z)-2,4,6,9-tetraene showed strong EAG activity, and their chemical data coincided well with those of the natural Comps. II and IV, indicating
the correctness of the structure determination by GC/FT-IR analysis
and its usefulness for Type II pheromone compounds.
...
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