Macrolides from the scent glands of the tropical butterflies Heliconius cydno and Heliconius pachinus.
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.
Schulz
Stefan
S
Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30 38106, Braunschweig, Germany. stefan.schulz@tu-bs.de
Yildizhan
Selma
S
Stritzke
Katja
K
Estrada
Catalina
C
Gilbert
Lawrence E
LE
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
D018942:Macrolides