We provide a synthesis of the literature describing biochemical interactions between microorganisms and insects by way of microbial volatile organic compound (MVOC) production. We evaluated the functionality and ecological context of MVOC signals, and explored important metabolic pathways involved in MVOC production. The cosmopolitan distribution of microorganisms creates a context for frequent, and frequently overlooked, insect responses to microbial emissions. There are numerous instances of MVOCs being closely associated with insect feeding behaviors, but some MVOCs are also powerful repellants. Emissions from microorganisms in situ may signal aspects of habitat suitability or potential exposure to entomopathogens. In some ecosystems, bacterial or fungal volatiles can also incite insect aggregations, or MVOCs can resemble sexual pheromones that elicit mating and oviposition behaviors from responding insects. A single microorganism or MVOC can have different effects on insect behaviors, especially across species, ontogenies, and habitats. There appears to be a multipartite basis for insect responses to MVOCs, and complex tritrophic interactions can result from the production of MVOCs. Many biochemical pathways for behaviorally active volatile production by microbial species are conserved across large taxonomic groupings of microorganisms. In addition, there is substantial functional redundancy in MVOCs: fungal tissues commonly produce polyketides and short-chain alcohols, whereas bacterial tissues tend to be more commonly associated with amines and pyrazines. We hypothesize that insect olfactory responses to emissions from microorganisms inhabiting their sensory environment are much more common than currently recognized, and that these signals represent evolutionarily reliable infochemicals. Insect chemoreception of microbial volatiles may contribute to the formation of neutral, beneficial, or even harmful symbioses and provide considerable insight into the evolution of insect behavioral responses to volatile compounds.

Microbial volatile emissions as insect semiochemicals.

Plants have evolved a range of strategies to manipulate the behaviour of their insect partners. One powerful strategy is to produce signals that already have a role in the animals' own communication systems. To investigate to what extent the evolution of floral scents is correlated with chemical communication in insects, I analyse the occurrence, commonness, and evolutionary patterns of the 71 most common 'floral' volatile organic compounds (VOCs) in 96 plant families and 87 insect families. I found an overlap of 87% in VOCs produced by plants and insects. 'Floral' monoterpenes showed strong positive correlation in commonness between plants (both gymnosperms and angiosperms) and herbivores, whereas the commonness of 'floral' aromatics was positively correlated between angiosperms and both pollinators and herbivores. According to a multivariate regression analysis the commonness of 'floral' aromatics was best explained by their commonness in pollinators, whereas monoterpenes were best explained by herbivores. Among pollinator orders, aromatics were significantly more common in Lepidoptera than in Hymenoptera, whereas monoterpenes showed no difference among the two orders. Collectively, these patterns suggest that plants and insects converge in overall patterns of volatile production, both for attraction and defence. Monoterpenes seem to have evolved primarily for defence under selection by herbivores, whereas aromatics evolved signalling functions in angiosperms, primarily for pollinator attraction.

https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1461-0248.2010.01451.x

The evolution of floral scent and insect chemical communication.

/pdf/are-alkyne-reductions-chemo-regio-and-stereoselective-enough-2k025fyx4w.pdf

Are alkyne reductions chemo-, regio-, and stereoselective enough to provide pure (Z)-olefins in polyfunctionalized bioactive molecules?

Sex pheromone communication in moths is a well investigated case of mate-finding by chemical signals, but the evolutionary causes of the great complexity and diversity of these signals are still not generally agreed on. In the present paper, I argue that there is no reason to dismiss species recognition as a possible cause of evolutionary change in moth sex pheromones. Admittedly, selection for species recognition cannot explain all of the diversity in sex pheromones and the data supporting this contention are weak, but the alternative causes suggested, invoking mate choice between conspecifics as the mechanism of sexual selection, has so far no empirical support. Finding and analysing genes responsible for mate choice is important to corroborate any theory of sexual selection and speciation. In this respect genetic dissection of moth pheromone communication has provided important progress. Mendelian genes controlling differences in mate choice and in the production of mate recognition signals have been found. Polymorphic pheromone systems give the population biologists unique possibilities to study mate choice and selection at the genotype level in nature.

Moth Pheromone Genetics and Evolution

Selected topics of the wittig reaction in the synthesis of natural products

Pheromone-XLII. 1,3,6,9-nonadecatetraen, das sexualpheromon des frostspanners operophtera brumata (geometridae).

(Z)-5-Decenylacetat, ein Sexuallockstoff für Männchen der SaateuleAgrotis segetum (Lepidoptera)

(3Z,6Z,9Z)-3,6,9-nonadecatriene - a component of the sex pheromonal system of the giant looper, schiffermüller (Lepidoptera: Geometridae)

By gaschromatographic-mass spectrometric methods 2-phenylethyl alcohol, benzylalcohol, phenylacetaldehyde and benzaldehyde were identified from scent brushes of male Noctuidae species (Lepidoptera).

[Male sex pheromones of noctuides (author's transl)].

(3z,6z,9z)-3,6,9-nonadecatriene - a component of the sex pheromonal system of the giant looper, boarmia (ascotis) selenaria schiffermueller (lepidoptera:geometridae)

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