The role of desaturases in the biosynthesis of marking pheromones in bumblebee males

Buček, Aleš; Vogel, Heiko; Matoušková, Petra; Prchalová, Darina; Žáček, Petr; Vrkoslav, Vladimír; Šebesta, Petr; Svatoš, Aleš; Jahn, Ullrich; Valterová, Irena; Pichová, Iva

doi:10.1016/j.ibmb.2013.05.003

Cited by 25 publications

(38 citation statements)

References 43 publications

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“…Yeast cells were harvested and total cellular lipids were extracted as described by Buček et al [34], and fatty acid methyl esters (FAMEs) were prepared according to Matoušková et al [35]. The resulting FAMEs were extracted with hexane (600 μl), and the extracts were analyzed by gas chromatography coupled to mass spectrometry (GC/MS) using the conditions described below.…”

Section: Methodsmentioning

confidence: 99%

Δ12-Fatty Acid Desaturase from Candida parapsilosis Is a Multifunctional Desaturase Producing a Range of Polyunsaturated and Hydroxylated Fatty Acids

et al. 2014

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Numerous Δ12-, Δ15- and multifunctional membrane fatty acid desaturases (FADs) have been identified in fungi, revealing great variability in the enzymatic specificities of FADs involved in biosynthesis of polyunsaturated fatty acids (PUFAs). Here, we report gene isolation and characterization of novel Δ12/Δ15- and Δ15-FADs named CpFad2 and CpFad3, respectively, from the opportunistic pathogenic yeast Candida parapsilosis. Overexpression of CpFad3 in Saccharomyces cerevisiae strains supplemented with linoleic acid (Δ9,Δ12-18:2) and hexadecadienoic acid (Δ9,Δ12-16:2) leads to accumulation of Δ15-PUFAs, i.e., α-linolenic acid (Δ9,Δ12,Δ15-18:3) and hexadecatrienoic acid with an unusual terminal double bond (Δ9,Δ12,Δ15-16:3). CpFad2 produces a range of Δ12- and Δ15-PUFAs. The major products of CpFad2 are linoleic and hexadecadienoic acid (Δ9,Δ12-16:2), accompanied by α-linolenic acid and hexadecatrienoic acid (Δ9,Δ12,Δ15-16:3). Using GC/MS analysis of trimethylsilyl derivatives, we identified ricinoleic acid (12-hydroxy-9-octadecenoic acid) as an additional product of CpFad2. These results demonstrate that CpFAD2 is a multifunctional FAD and indicate that detailed analysis of fatty acid derivatives might uncover a range of enzymatic selectivities in other Δ12-FADs from budding yeasts (Ascomycota: Saccharomycotina).

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Section: Methodsmentioning

confidence: 99%

Δ12-Fatty Acid Desaturase from Candida parapsilosis Is a Multifunctional Desaturase Producing a Range of Polyunsaturated and Hydroxylated Fatty Acids

et al. 2014

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“…In insects, Δ9-desaturases serve in biosynthetic pathways towards cuticular hydrocarbons in the fruit fly Drosophila melanogaster 2324, scent-marking pheromones in male bumblebees25 and long-range sex pheromones in some female moths2627. However, in the latter group, molecular reconstructions of biosynthetic pathways revealed that the majority of chemical structures derive from the evolution of novel desaturase multigene families absent from other insect orders2728.…”

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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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“…In insects, desaturases have been extensively studied based on their role in chemical communication and potential to contribute to speciation. To date, a number of desaturase genes have been shown to be involved in pheromone biosynthesis in many insects including moths (Roelofs & Rooney, ; Buček et al ., ) and flies (Knipple et al ., ; Buček et al ., ). In these systems, the introduction of carbon–carbon double bonds at specific positions in pheromone precursors to generate pheromone components that vary in chain length, double‐bond number, double‐bond position and double‐bond orientation contributes to the structural diversity in pheromone structures that drive species specificity (Knipple et al ., ; Roelofs & Rooney, ).…”

Section: Discussionmentioning

confidence: 99%

Knockdown of a metathoracic scent gland desaturase enhances the production of (E)‐4‐oxo‐2‐hexenal and suppresses female sexual attractiveness in the plant bug Adelphocoris suturalis

Luo

et al. 2017

Insect Molecular Biology

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Insect sex pheromones (SPs) are central to mate-finding behaviour, and play an essential role in the survival and reproduction of organisms. Understanding the roles, biosynthetic pathways and evolution of insect chemical communication systems has been an exciting challenge for biologists. Compared with Lepidoptera, little is known about the mechanisms underlying pheromone biosynthesis in Hemiptera. In this study, we isolated and characterized two new desaturase-like genes, termed Asutdes1 and Asutdes2, from Adelphocoris suturalis, an important agricultural pest in China. Although the two genes encode an identical protein, Southern blot analysis revealed that they are duplicated genes. The Asutdes2 transcript is more abundant than Asutdes1 in the tissues tested, in particular the metathoracic scent gland and fat body. Silencing Asutdes expression in females by injecting double-stranded RNA (dsAsutdes) against a portion of the coding sequence shared by the two genes enhanced the production of (E)-4-oxo-2-hexenal, a component of the A. suturalis SP blend, and dramatically suppressed the sexual attractiveness of A. suturalis females. We conclude that dsAsutdes is associated with the SP biosynthetic pathway in A. suturalis.

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The role of desaturases in the biosynthesis of marking pheromones in bumblebee males

Cited by 25 publications

References 43 publications

Δ12-Fatty Acid Desaturase from Candida parapsilosis Is a Multifunctional Desaturase Producing a Range of Polyunsaturated and Hydroxylated Fatty Acids

Δ12-Fatty Acid Desaturase from Candida parapsilosis Is a Multifunctional Desaturase Producing a Range of Polyunsaturated and Hydroxylated Fatty Acids

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

Knockdown of a metathoracic scent gland desaturase enhances the production of (E)‐4‐oxo‐2‐hexenal and suppresses female sexual attractiveness in the plant bug Adelphocoris suturalis

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