2-(Tetrahydrofuran-2-yl)acetic acid and ester derivatives as long-range pollinator attractants in the sexually deceptive orchid Cryptostylis ovata

Björn Bohman, Alyssa M. Weinstein, Ryan D. Phillips, Rod Peakall, Gavin R. Flematti

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)1107-1113
Number of pages7
JournalJournal of Natural Products
Volume82
Issue number5
DOIs
Publication statusPublished - 24 May 2019

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Enantiomers
Bioassay
Biological Assay
Acetates
Deception
Derivatives
Pollination
Ejaculation
Pheromones
Fractionation
Biological Products
Acetic Acid
Insects
Esters
High Pressure Liquid Chromatography
tetrahydrofuran

Cite this

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title = "2-(Tetrahydrofuran-2-yl)acetic acid and ester derivatives as long-range pollinator attractants in the sexually deceptive orchid Cryptostylis ovata",
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.",
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T1 - 2-(Tetrahydrofuran-2-yl)acetic acid and ester derivatives as long-range pollinator attractants in the sexually deceptive orchid Cryptostylis ovata

AU - Bohman, Björn

AU - Weinstein, Alyssa M.

AU - Phillips, Ryan D.

AU - Peakall, Rod

AU - Flematti, Gavin R.

PY - 2019/5/24

Y1 - 2019/5/24

N2 - 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.

AB - 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.

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DO - 10.1021/acs.jnatprod.8b00772

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