The discovery of 2,5-dialkylcyclohexan-1,3-diones as a new class of natural products

Date

2009

Authors

Franke, Stephan
Ibarra, Fernando
Schulz, Claudia
Twele, R.
Poldy, Jacqueline
Barrow, Russell
Peakall, Rodney
Schiestl, F P
Francke, Wittko

Journal Title

Journal ISSN

Volume Title

Publisher

National Academy of Sciences (USA)

Abstract

Orchids employing sexual deceit attract males of their pollinator species through specific volatile signals that mimic female-released sex pheromones. One of these signals proved to be 2-ethyl-5-propylcyclohexan-1,3-dione (chiloglottone1), a new natural product that was shown to be most important in the relations between orchids of the genus Chiloglottis, native to Australia, and corresponding pollinator species. Systematic investigations on the mass spectrometric fragmentation pattern of 2,5-dialkylcyclohexan-1,3-diones identified key ions providing information about the structures of the substituents at positions 2 and 5. Results enabled us to identify 2-ethyl-5-pentylcyclohexan-1,3-dione (chiloglottone2) and 2-butyl-5- methylcyclohexan-1,3-dione (chiloglottone3) as new natural products that play a decisive role in the pollination syndrome of some Chiloglottis species. During field bioassays, pure synthetic samples of chiloglottone1-3 or mixtures thereof proved to be attractive to the corresponding orchid pollinators. Because of their likely biogenesis from ubiquitous fatty acid precursors, 2,5-dialkylcyclohexan-1,3-diones may represent a hitherto overlooked, widespread class of natural products.

Description

Keywords

Keywords: cyclohexane derivative; natural product; article; bioassay; chemical analysis; chemical structure; mass spectrometry; Orchidaceae; pollination; pollinator; priority journal; Biological Products; Cyclohexanones; Magnetic Resonance Spectroscopy; Orchidaceae 2-butyl-5-methylcyclohexan-1,3-dione; 2-ethyl-5-pentylcyclohexan-1,3-dione; Chiloglottis; Mass spectrometry; Semiochemical

Citation

Source

PNAS - Proceedings of the National Academy of Sciences of the United States of America

Type

Journal article

Book Title

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2037-12-31