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Issue 21, 2007
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Macrolides from the scent glands of the tropical butterflies Heliconius cydno and Heliconius pachinus

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Abstract

The four major components present in scent gland extracts of the male Costa Rica longwing butterflies Heliconius cydno and Heliconius pachinus were identified as 12- and 14-membered macrolides containing a C18-carbon skeleton. By use of micro-reactions and spectrometric examinations, structural proposals were made and subsequently proven by synthesis, using ring-closing-metathesis as the key steps. These macrolides, (9Z,11E,13S)-octadeca-9,11-dien-13-olide (5, S-coriolide), (9Z,11E,13S,15Z)-octadeca-9,11,15-trien-13-olide (6), (9Z,13S)-octadec-9-en-13-olide (13), and (9Z,11S)-octadec-9-en-11-olide (25), are biosynthetically obviously derived from oleic, linoleic, and linolenic acids. Their absolute configurations were determined by gas chromatographic investigations on chiral phases, showing all to possess (S)-configuration.

Graphical abstract: Macrolides from the scent glands of the tropical butterflies Heliconius cydno and Heliconius pachinus

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Publication details

The article was received on 05 Jul 2007, accepted on 07 Sep 2007 and first published on 18 Sep 2007


Article type: Paper
DOI: 10.1039/B710284D
Citation: Org. Biomol. Chem., 2007,5, 3434-3441
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    Macrolides from the scent glands of the tropical butterflies Heliconius cydno and Heliconius pachinus

    S. Schulz, S. Yildizhan, K. Stritzke, C. Estrada and L. E. Gilbert, Org. Biomol. Chem., 2007, 5, 3434
    DOI: 10.1039/B710284D

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