The Biosynthesis of Hexahydrofarnesylacetone in the Butterfly Pieris brassicae

Schulz, Stefan; Yildizhan, Selma; Loon, Joop J. A. van

doi:10.1007/s10886-011-9939-y

Cited by 32 publications

(27 citation statements)

References 10 publications

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“…The third presumptive pheromone component, trimethylpentadecan-2-ol, was not part of the study as it is a phytol-derived compound50 expected to originate from the diet and not related to FA biochemistry.…”

Section: Resultsmentioning

confidence: 99%

Sex pheromone biosynthetic pathways are conserved between moths and the butterfly Bicyclus anynana

et al. 2014

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Although phylogenetically nested within the moths, butterflies have diverged extensively in a number of life history traits. Whereas moths rely greatly on chemical signals, visual advertisement is the hallmark of mate finding in butterflies. In the context of courtship, however, male chemical signals are widespread in both groups although they likely have multiple evolutionary origins. Here, we report that in males of the butterfly Bicyclus anynana, courtship scents are produced de novo via biosynthetic pathways shared with females of many moth species. We show that two of the pheromone components that play a major role in mate choice, namely the (Z)-9-tetradecenol and hexadecanal, are produced through the activity of a fatty acyl Δ11-desaturase and two specialized alcohol-forming fatty acyl reductases. Our study provides the first evidence of conservation and sharing of ancestral genetic modules for the production of FA-derived pheromones over a long evolutionary timeframe thereby reconciling mate communication in moths and butterflies.

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Section: Resultsmentioning

confidence: 99%

Sex pheromone biosynthetic pathways are conserved between moths and the butterfly Bicyclus anynana

et al. 2014

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“…MSP3 is a phytol-derived compound that originates from chlorophyll-a degradation4041. Similar to MSP1, the reduction in MSP3 production in DS males could be controlled by differential regulation of its biosynthetic enzymes.…”

Section: Discussionmentioning

confidence: 99%

Phenotypic plasticity in sex pheromone production in Bicyclus anynana butterflies

Dion

Monteiro

Yew

2016

Sci Rep

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Phenotypic plasticity refers to the environmental control of phenotypes. Cues experienced during development (developmental plasticity) or during adulthood (acclimatization) can both affect adult phenotypes. Phenotypic plasticity has been described in many traits but examples of developmental plasticity in physiological traits, in particular, remain scarce. We examined developmental plasticity and acclimatization in pheromone production in the butterfly Bicyclus anynana in response to rearing temperature. B. anynana lives in the African tropics where warm rearing temperatures of the wet season produce active males that court and females that choose, whereas cooler temperatures of the dry season lead to choosy less active males and courting females. We hypothesized that if male pheromone production is costly, it should be reduced in the dry season form. After describing the ultrastructure of pheromone producing cells, we showed that dry season males produced significantly less sex pheromones than wet season males, partly due to acclimatization and partly due to developmental plasticity. Variation in levels of one of the compounds is associated with differential regulation of a pheromone biosynthetic enzyme gene. This plasticity might be an adaptation to minimize pheromone production costs during the stressful dry season.

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“…Benzyl alcohol, geranyl acetone, and benzyl benzoate trended toward being emitted by more liftoff queens than inhive queens, and benzyl alcohol and benzyl benzoate and were produced at significantly higher quantities in liftoff queens (Table I). Geranyl acetone is likely a biosynthetic derivative of farnesol (Schulz et al 2011), which is a component of worker Nasanov glands (Pickett et al 1980). The five-compound Nasanov pheromone blend is attractive to honey bee swarms (Schmidt 1999).…”

Section: Discussionmentioning

confidence: 99%

Queen-produced volatiles change dynamically during reproductive swarming and are associated with changes in honey bee (Apis mellifera) worker behavior

et al. 2015

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-During colony fission, honey bee workers are exquisitely sensitive to the presence of their queen in airborne swarms and bivouacs and will abandon swarming if she is absent. However, it is not known whether swarming queens produce a chemical bouquet that is distinct from non-swarming queens, containing either unique chemicals or altered proportions of chemicals. We found that queens emitted higher quantities and greater numbers of unique volatiles at liftoff than they did prior to swarming or in clustered bivouacs, and swarming workers tended to be attracted to these liftoff volatile blends. Pentadecane and heptadecane were collected most frequently and emitted in significantly higher quantities by queens at liftoff; these compounds have been described as pheromone components in other social insects, but not yet in honey bees. Our results suggest that volatile emission by queens is more dynamic than previously thought and that changes in their chemical signals may play a role in regulating the behavior of swarming workers.honey bees / chemical ecology / pheromones / worker behavior / swarming

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The Biosynthesis of Hexahydrofarnesylacetone in the Butterfly Pieris brassicae

Cited by 32 publications

References 10 publications

Sex pheromone biosynthetic pathways are conserved between moths and the butterfly Bicyclus anynana

Sex pheromone biosynthetic pathways are conserved between moths and the butterfly Bicyclus anynana

Phenotypic plasticity in sex pheromone production in Bicyclus anynana butterflies

Queen-produced volatiles change dynamically during reproductive swarming and are associated with changes in honey bee (Apis mellifera) worker behavior

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