ArticleProceedings of the National Academy of Sciences of the United States of America2015
Isolation and determination of absolute configurations of insect-produced methyl-branched hydrocarbons.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers, 1 of them a synthesis that pooled it.
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Who cites it
20 citing papers in PubMed, 1 synthesis or guideline pooled it, 57 citations in OpenAlex.
- Evolution of Cuticular Hydrocarbons in the Hymenoptera: a Meta-Analysis.Journal of chemical ecology · 2015Pooled it
- Independent Evolution of Linear and Branched Cuticular Hydrocarbons in Ants: A Hypothesis.Insects · 2026Article
- Modular Stereoselective Synthesis of Sex Pheromone ofMolecules (Basel, Switzerland) · 2025Article
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- Enantioselective Synthesis of the Active Sex Pheromone Components of the Female Lichen Moth,Molecules (Basel, Switzerland) · 2024Article
- Evolutionarily related host and microbial pathways regulate fat desaturation in C. elegans.Nature communications · 2024Article
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- A Multimethodological Approach for the Chemical Characterization of Edible Insects: The Case Study ofFoods (Basel, Switzerland) · 2023Article
- Indirect exposure to insect growth disruptors affects honey bee (Apis mellifera) reproductive behaviors and ovarian protein expression.PloS one · 2023Article
- Review
- Chemical identification of an active component and putative neural mechanism for repellent effect of a native ant's odor on invasive species.Frontiers in physiology · 2022Article
- The Importance of Methyl-Branched Cuticular Hydrocarbons for Successful Host Recognition by the Larval Ectoparasitoid Holepyris sylvanidis.Journal of chemical ecology · 2020Article
- Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals: Reductive Transposition of Allylic Diazenes.Angewandte Chemie (International ed. in English) · 2017Article
- The evolution of queen control over worker reproduction in the social Hymenoptera.Ecology and evolution · 2017Article
- Specialized odorant receptors in social insects that detect cuticular hydrocarbon cues and candidate pheromones.Nature communications · 2017Article
- Chemosensory sensitivity reflects reproductive status in the ant Harpegnathos saltator.Scientific reports · 2017Article
- Sex and Aggregation-Sex Pheromones of Cerambycid Beetles: Basic Science and Practical Applications.Journal of chemical ecology · 2016Review
- Bromotyrosine-derived metabolites from an Indonesian marine sponge in the family Aplysinellidae (Order Verongiida).Bioorganic & medicinal chemistry letters · 2016Article
- Determination of the Absolute Configuration of Female-Produced Contact Sex Pheromone Components of the Longhorned Beetle, Neoclytus acuminatus acuminatus (F).Journal of chemical ecology · 2015Article
- Wax, sex and the origin of species: Dual roles of insect cuticular hydrocarbons in adaptation and mating.BioEssays : news and reviews in molecular, cellular and developmental biology · 2015Review
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Although the effects of stereochemistry have been studied extensively for volatile insect pheromones, little is known about the effects of chirality in the nonvolatile methyl-branched hydrocarbons (MBCHs) used by many insects as contact pheromones. MBCHs generally contain one or more chiral centers and so two or more stereoisomeric forms are possible for each structure. However, it is not known whether insects biosynthesize these molecules in high stereoisomeric purity, nor is it known whether insects can distinguish the different stereoisomeric forms of MBCHs. This knowledge gap is due in part to the lack of methods for isolating individual MBCHs from the complex cuticular hydrocarbon (CHC) blends of insects, as well as the difficulty in determining the absolute configurations of the isolated MBCHs. To address these deficiencies, we report a straightforward method for the isolation of individual cuticular hydrocarbons from the complex CHC blend. The method was used to isolate 36 pure MBCHs from 20 species in nine insect orders. The absolute stereochemistries of the purified MBCHs then were determined by digital polarimetry. The absolute configurations of all of the isolated MBCHs were determined to be (R) by comparison with a library of synthesized, enantiomerically pure standards, suggesting that the biosynthetic pathways used to construct MBCHs are highly conserved within the Insecta. The development of a straightforward method for isolation of specific CHCs will enable determination of their functional roles by providing pure compounds for bioassays.
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