2-(Tetrahydrofuran-2-yl)acetic Acid and Ester Derivatives as Long-Range Pollinator Attractants in the Sexually Deceptive Orchid <i>Cryptostylis ovata</i>

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

doi:10.1021/acs.jnatprod.8b00772

Cited by 11 publications

(11 citation statements)

References 54 publications

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“…To test whether the electrophysiologically active compounds are responsible for the attraction of the different pollinator species, field trials should be undertaken. It is possible that the compounds responsible for pollinator attraction include compounds not detected via GC-EAD or by our compound screening process [22,58]. For example, compounds that are important for pollinator attraction, but are shared between the three ecotypes, would not be identified through our screening for qualitative differences in compounds between ecotypes.…”

Section: Floral Volatile Composition Of the Ecotypesmentioning

confidence: 99%

Three Chemically Distinct Floral Ecotypes in Drakaea livida, an Orchid Pollinated by Sexual Deception of Thynnine Wasps

Weinstein

Bohman

Flematti

et al. 2022

Plants

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Sexually deceptive orchids are unusual among plants in that closely related species typically attract different pollinator species using contrasting blends of floral volatiles. Therefore, intraspecific variation in pollinator attraction may also be underpinned by differences in floral volatiles. Here, we tested for the presence of floral ecotypes in the sexually deceptive orchid Drakaea livida and investigated if the geographic range of floral ecotypes corresponded to variation in pollinator availability. Pollinator choice trials revealed the presence of three floral ecotypes within D. livida that each attracts a different species of thynnine wasp as a pollinator. Surveys of pollinator distribution revealed that the distribution of one of the ecotypes was strongly correlated with that of its pollinator, while another pollinator species was present throughout the range of all three ecotypes, demonstrating that pollinator availability does not always correlate with ecotype distribution. Floral ecotypes differed in chemical volatile composition, with a high degree of separation evident in principal coordinate analysis. Some compounds that differed between ecotypes, including pyrazines and (methylthio)phenols, are known to be electrophysiologically active in thynnine wasp antennae. Based on differences in pollinator response and floral volatile profile, the ecotypes represent distinct entities and should be treated as such in conservation management.

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Section: Floral Volatile Composition Of the Ecotypesmentioning

confidence: 99%

Three Chemically Distinct Floral Ecotypes in Drakaea livida, an Orchid Pollinated by Sexual Deception of Thynnine Wasps

Weinstein

Bohman

Flematti

et al. 2022

Plants

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“…The active compounds include n-alkanes and alkenes,a long with hydroxy-and keto acids in Ophrys, [2] cyclohexane-1,3-diones in Chiloglottis, [3] alkyl-and hydroxymethylpyrazines in Drakaea, [1e] (methylthio)phenols in Caladenia [1h] and tetrahydrofuranyl acids in Cryptostylis. [4] Most systems involve multiple compounds,usually derived from similar biosynthetic origins. Only one example of am ixed pheromone/pollinator attractant system originating from distinct biosynthetic pathways has been reported:t he orchid Caladenia plicata attracts its Zeleboria sp.Cthynnine wasp pollinator with as pecific mixture of the terpene citronellol and al ikely polyketidederived acetophenone.…”

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confidence: 99%

A Specific Blend of Drakolide and Hydroxymethylpyrazines: An Unusual Pollinator Sexual Attractant Used by the Endangered Orchid Drakaea micrantha

et al. 2019

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Bioactive natural products underpin the intriguing pollination strategy used by sexually deceptive orchids. These compounds, which mimic the sex pheromones of the female insect, are emitted in particular blends to lure male insect pollinators of specific species. By combining methods from field biology, analytical chemistry, electrophysiology, crystallography, and organic synthesis, we report that an undescribed β‐hydroxylactone, in combination with two specific hydroxymethylpyrazines, act as pollinator attractants in the rare hammer orchid Drakaea micrantha. This discovery represents an unusual case of chemically unrelated compounds being used together as a sexual attractant. Furthermore, this is the first example of the identification of pollinator attractants in an endangered orchid, enabling the use of chemistry in orchid conservation. Our synthetic blend is now available to be used in pollinator surveys to locate suitable sites for plant conservation translocations.

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“…A custom-made manual fraction collector was used, with samples collected in glass capillaries (100 × 1.55 mm id, Hirschmann Laborgeräte, Eberstadt, Germany) positioned in an aluminium holder submerged in a dry ice/acetone bath. All fractions were eluted with dichloromethane and stored at −20 • C until used for microderivatisation experiments [26].…”

Section: General Experimental Proceduresmentioning

confidence: 99%

“…In Australian sexually deceptive orchids, 1,3-cyclohexanediones (chiloglottones) have been identified as pollinator attractants in Chiloglottis [18], as have hydroxymethylpyrazines and a β-hydroxylactone (drakolide) in Drakaea [19][20][21][22], (methylthio)phenols, acetophenones and monoterpenes in Caladenia [23][24][25], and tetrahydrofuran acid derivatives in Cryptostylis [26].…”

Section: Introductionmentioning

confidence: 99%

Identification of (Z)-8-Heptadecene and n-Pentadecane as Electrophysiologically Active Compounds in Ophrys insectifera and Its Argogorytes Pollinator

Bohman

Weinstein

Mozūraitis

et al. 2020

IJMS

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Sexually deceptive orchids typically depend on specific insect species for pollination, which are lured by sex pheromone mimicry. European Ophrys orchids often exploit specific species of wasps or bees with carboxylic acid derivatives. Here, we identify the specific semiochemicals present in O. insectifera, and in females of one of its pollinator species, Argogorytes fargeii. Headspace volatile samples and solvent extracts were analysed by GC-MS and semiochemicals were structurally elucidated by microderivatisation experiments and synthesis. (Z)-8-Heptadecene and n-pentadecane were confirmed as present in both O. insectifera and A. fargeii female extracts, with both compounds being found to be electrophysiologically active to pollinators. The identified semiochemicals were compared with previously identified Ophrys pollinator attractants, such as (Z)-9 and (Z)-12-C27-C29 alkenes in O. sphegodes and (Z)-9-octadecenal, octadecanal, ethyl linoleate and ethyl oleate in O. speculum, to provide further insights into the biosynthesis of semiochemicals in this genus. We propose that all these currently identified Ophrys semiochemicals can be formed biosynthetically from the same activated carboxylic acid precursors, after a sequence of elongation and decarbonylation reactions in O. sphegodes and O. speculum, while in O. insectifera, possibly by decarbonylation without preceding elongation.

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2-(Tetrahydrofuran-2-yl)acetic Acid and Ester Derivatives as Long-Range Pollinator Attractants in the Sexually Deceptive Orchid Cryptostylis ovata

Cited by 11 publications

References 54 publications

Three Chemically Distinct Floral Ecotypes in Drakaea livida, an Orchid Pollinated by Sexual Deception of Thynnine Wasps

Three Chemically Distinct Floral Ecotypes in Drakaea livida, an Orchid Pollinated by Sexual Deception of Thynnine Wasps

A Specific Blend of Drakolide and Hydroxymethylpyrazines: An Unusual Pollinator Sexual Attractant Used by the Endangered Orchid Drakaea micrantha

Identification of (Z)-8-Heptadecene and n-Pentadecane as Electrophysiologically Active Compounds in Ophrys insectifera and Its Argogorytes Pollinator

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