title: Macrolides from the scent glands of the tropical butterflies Heliconius cydno and Heliconius pachinus.
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.
authors.affiliation: Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30 38106, Braunschweig, Germany. stefan.schulz@tu-bs.de
authors.forename: Stefan
authors.initials: S
authors.lastname: Schulz
authors.forename: Selma
authors.initials: S
authors.lastname: Yildizhan
authors.forename: Katja
authors.initials: K
authors.lastname: Stritzke
authors.forename: Catalina
authors.initials: C
authors.lastname: Estrada
authors.forename: Lawrence E
authors.initials: LE
authors.lastname: Gilbert
mesh_terms: D000818:Animals; D002080:Butterflies / Q000737:chemistry*; D002849:Chromatography, Gas; D003364:Costa Rica; D018942:Macrolides / Q000737:chemistry*; D008297:Male; D013058:Mass Spectrometry; D015394:Molecular Structure; D012543:Scent Glands / Q000737:chemistry*; D013237:Stereoisomerism; D014329:Tropical Climate
chemical_list: D018942:Macrolides