| Title: | Head and Tail Oxidized Terpenoid Esters from Androconia of Heliconius erato Butterflies |
| Author(s): | Szczerbowski D; Ehlers S; Darragh K; Jiggins C; Schulz S; |
| Address: | "Institute of Organic Chemistry, Technische Universitat Braunschweig, 38106 Braunschweig Germany. Department of Evolution and Ecology, University of California, Davis, California 95616, United States. Department of Zoology, University of Cambridge, Downing Street, CB2 3EJ, Cambridge, United Kingdom" |
| DOI: | 10.1021/acs.jnatprod.2c00300 |
| ISSN/ISBN: | 1520-6025 (Electronic) 0163-3864 (Linking) |
| Abstract: | "Heliconius erato is a neotropical butterfly species that is part of a complex mimicry ring, with colorful wing patterns. For intraspecific communication, males use pheromones that are released from two different scent-emitting structures. Scent glands located near the abdominal claspers of males, containing antiaphrodisiac pheromones, release a highly complex mixture of compounds that is transferred to females during mating, rendering them unattractive to other males. On the other hand, androconia, scent-emitting scale areas on the wings of male butterflies, release a structurally more restricted set of compounds that likely serves an aphrodisiac role. We report here on two structurally related compounds that are the major androconial constituents, produced in high amounts and are not volatile due to their high molecular mass. Their structures were established by extensive analysis of mass, infrared, and NMR spectra, as well as microderivatization reactions of the natural extract. After establishing synthetic access, the compounds were unequivocally identified as two unusual head and tail oxidized terpenoids, (4E,8E,12E)-4,8,12-trimethyl-16-oxoheptadeca-4,8,12-trien-1-yl oleate (1) and stearate (2). Although behavioral assays are necessary to fully comprehend their role in the chemical communication of the species, hypotheses for their use by the butterflies are also discussed" |
| Keywords: | "Animals *Butterflies/chemistry Esters Female Male Pheromones/chemistry Plant Extracts/analysis Terpenes/analysis Wings, Animal/chemistry;" |
| Notes: | "MedlineSzczerbowski, Daiane Ehlers, Stephanie Darragh, Kathy Jiggins, Chris Schulz, Stefan eng Research Support, Non-U.S. Gov't Review 2022/05/20 J Nat Prod. 2022 May 27; 85(5):1428-1435. doi: 10.1021/acs.jnatprod.2c00300. Epub 2022 May 19" |
