Macrolides from the scent glands of the tropical butterflies Heliconius cydno and Heliconius pachinus |
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Authors: | Schulz Stefan Yildizhan Selma Stritzke Katja Estrada Catalina Gilbert Lawrence E |
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Institution: | Institut für Organische Chemie, Technische Universit?t Braunschweig, Hagenring 30 38106, Braunschweig, Germany. stefan.schulz@tu-bs.de |
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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 C(18)-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. |
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