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J Nat Prod

Title:		2-(Tetrahydrofuran-2-yl)acetic Acid and Ester Derivatives as Long-Range Pollinator Attractants in the Sexually Deceptive Orchid Cryptostylis ovata
Author(s):		Bohman B; Weinstein AM; Phillips RD; Peakall R; Flematti GR;
Address:		"School of Molecular Sciences , The University of Western Australia , Crawley , WA 6009 , Australia. Ecology and Evolution, Research School of Biology , The Australian National University , Canberra , ACT 2600 , Australia. Department of Ecology, Environment and Evolution , La Trobe University , Melbourne , Victoria 3086 , Australia. Department of Biodiversity Conservation and Attractions , Kings Park Science , 1 Kattidj Close , West Perth , WA , Australia"
Journal Title:		J Nat Prod
Year:		2019
Volume:		20190328
Issue:		5
Page Number:		1107 - 1113
DOI:		10.1021/acs.jnatprod.8b00772
ISSN/ISBN:		1520-6025 (Electronic) 0163-3864 (Linking)
Abstract:		"Sexually deceptive orchids achieve pollination by luring male insects to flowers through chemical and sometimes visual mimicry of females. An extreme example of this deception occurs in Cryptostylis, one of only two genera where sexual deception is known to induce pollinator ejaculation. In the present study, bioassay-guided fractionations of Cryptostylis solvent extracts in combination with field bioassays were implemented to isolate and identify floral volatiles attractive to the pollinator Lissopimpla excelsa. ( S)-2-(Tetrahydrofuran-2-yl)acetic acid [( S)-1] and the ester derivatives methyl ( S)-2-(tetrahydrofuran-2-yl)acetate [( S)-2] and ethyl ( S)-2-(tetrahydrofuran-2-yl)acetate [( S)-3], all previously unknown semiochemicals, were confirmed to attract L. excelsa males in field bioassays. Chiral-phase GC and HPLC showed that the natural product 1 comprised a single enantiomer, its S-configuration being confirmed by synthesis of the two enantiomers from known enantiomers of tetrahydrofuran-2-carboxylic acid"
Keywords:		Animals Furans/chemistry/*isolation & purification/pharmacology Hymenoptera Male Orchidaceae/*chemistry *Pollination Stereoisomerism;
Notes:		"MedlineBohman, Bjorn Weinstein, Alyssa M Phillips, Ryan D Peakall, Rod Flematti, Gavin R eng Research Support, Non-U.S. Gov't 2019/03/29 J Nat Prod. 2019 May 24; 82(5):1107-1113. doi: 10.1021/acs.jnatprod.8b00772. Epub 2019 Mar 28"