Monoterpenyl esters in juvenile mountain pine beetle and sex-specific release of the aggregation pheromone
            <i>trans</i>
            -verbenol

Chiu, Catherine; Keeling, Christopher I.; Bohlmann, Jöerg

doi:10.1073/pnas.1722380115

Cited by 47 publications

(45 citation statements)

References 47 publications

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“…One of the oxidised monoterpenes produced by a MPB P450 is the aggregation pheromone (−)‐ trans ‐verbenol. (−)‐ trans ‐Verbenol is derived from the pine oleoresin monoterpene (−)‐α‐pinene and accumulates in the phloem‐feeding MPB larvae in the form of monoterpenyl ester (Chiu et al ., 2018, 2019c2018, 2019b). These esters then serve as reservoir for the release of aggregation pheromone in the adult MPB.…”

Section: The Mountain Pine Beetle System: Example For Co‐evolution Ofmentioning

confidence: 99%

Oleoresin defenses in conifers: chemical diversity, terpene synthases and limitations of oleoresin defense under climate change

2019

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Summary Conifers have evolved complex oleoresin terpene defenses against herbivores and pathogens. In co‐evolved bark beetles, conifer terpenes also serve chemo‐ecological functions as pheromone precursors, chemical barcodes for host identification, or nutrients for insect‐associated microbiomes. We highlight the genomic, molecular and biochemical underpinnings of the large chemical space of conifer oleoresin terpenes and volatiles. Conifer terpenes are predominantly the products of the conifer terpene synthase (TPS) gene family. Terpene diversity is increased by cytochromes P450 of the CYP720B class. Many conifer TPS are multiproduct enzymes. Multisubstrate CYP720B enzymes catalyse multistep oxidations. We summarise known terpenoid gene functions in various different conifer species with reference to the annotated terpenoid gene space in a spruce genome. Overall, biosynthesis of terpene diversity in conifers is achieved through a system of biochemical radiation and metabolic grids. Expression of TPS and CYP720B genes can be specific to individual cell types of constitutive or traumatic resin duct systems. Induced terpenoid transcriptomes in resin duct cells lead to dynamic changes of terpene composition and quantity to fend off herbivores and pathogens. While terpenoid defenses have contributed much to the evolutionary success of conifers, under new conditions of climate change, these defences may become inconsequential against range‐expanding forest pests.

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Section: The Mountain Pine Beetle System: Example For Co‐evolution Ofmentioning

confidence: 99%

Oleoresin defenses in conifers: chemical diversity, terpene synthases and limitations of oleoresin defense under climate change

2019

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“…Chen et al, 2016;Qiu et al, 2012;Reed et al, 1994). Specific CYPs function in the midgut and fat body of bark beetles, converting plant monoterpenes into aggregation pheromones (Chiu et al, 2018(Chiu et al, , 2019Huber et al, 2007;Nadeau et al, 2017;Sandstrom et al, 2008Sandstrom et al, , 2006. In locusts, a tissue-specific CYP transforms phenylalanine into a precursor for cyanide production (Wei et al, 2019), and in the fall webworm, Hyphantria cunea, another pheromone gland-specific CYP catalyzes the epoxidation of open chain precursors of cis-9,10-epoxy-(3Z,6Z )-3,6-henicosadiene and cis-9,10-epoxy-(3Z,6Z )-1,3,6-henicosatriene to their final cyclic forms (Rong et al, 2014).…”

Section: Biosynthetic Pathway Assembly In Gland Cell Type Evolutionmentioning

confidence: 99%

Molecular evolution of gland cell types and chemical interactions in animals

Brückner

Parker

2020

Journal of Experimental Biology

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Across the Metazoa, the emergence of new ecological interactions has been enabled by the repeated evolution of exocrine glands. Specialized glands have arisen recurrently and with great frequency, even in single genera or species, transforming how animals interact with their environment through trophic resource exploitation, pheromonal communication, chemical defense and parental care. The widespread convergent evolution of animal glands implies that exocrine secretory cells are a hotspot of metazoan cell type innovation. Each evolutionary origin of a novel gland involves a process of 'gland cell type assembly': the stitching together of unique biosynthesis pathways; coordinated changes in secretory systems to enable efficient chemical release; and transcriptional deployment of these machineries into cells constituting the gland. This molecular evolutionary process influences what types of compound a given species is capable of secreting, and, consequently, the kinds of ecological interactions that species can display. Here, we discuss what is known about the evolutionary assembly of gland cell types and propose a framework for how it may happen. We posit the existence of 'terminal selector' transcription factors that program gland function via regulatory recruitment of biosynthetic enzymes and secretory proteins. We suggest ancestral enzymes are initially co-opted into the novel gland, fostering pleiotropic conflict that drives enzyme duplication. This process has yielded the observed pattern of modular, gland-specific biosynthesis pathways optimized for manufacturing specific secretions. We anticipate that single-cell technologies and gene editing methods applicable in diverse species will transform the study of animal chemical interactions, revealing how gland cell types are assembled and functionally configured at a molecular level.

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“…It was previously thought that only female MPB produce, and immediately release, trans -verbenol by oxidation of α-pinene upon landing on a new host tree 11,19 . However, we recently showed that both male and female MPB accumulate verbenol as fatty acid esters during their juvenile life stages, suggesting that formation of verbenol and verbenyl esters occurs in both sexes possibly as part of monoterpene detoxification in the feeding larvae 20 . While both sexes accumulate verbenyl esters as larvae, only females retain these metabolites when they emerge as adults from the brood tree and may use them as a source for sex-specific pheromone release 20 .…”

Section: Introductionmentioning

confidence: 98%

The cytochrome P450 CYP6DE1 catalyzes the conversion of α-pinene into the mountain pine beetle aggregation pheromone trans-verbenol

Chiu

Keeling

Bohlmann

2019

Sci Rep

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The recent outbreak of the mountain pine beetle (Dendroctonus ponderosae; MPB) has affected over 20 M hectares of pine forests in western North America. During the colonization of host trees, female MPB release the aggregation pheromone (−)-trans-verbenol. (−)-trans-Verbenol is thought to be produced from the pine defense compound (−)-α-pinene by cytochrome P450 (P450) dependent hydroxylation. MPB may also use P450s for the detoxification of other monoterpenes of the pine defense system. Here we describe the functional characterization of MPB CYP6DE1. CYP6DE1, but not the closely related CYP6DE2, used the bicyclic monoterpenes (−)-α-pinene, (+)-α-pinene, (−)-β-pinene, (+)-β-pinene and (+)-3-carene as substrates. CYP6DE1 was not active with other monoterpenes or diterpene resin acids that were tested as substrates. trans-Verbenol is the major product of CYP6DE1 activity with (−)-α-pinene or (+)-α-pinene as substrates. When tested with blends of different ratios of (−)-α-pinene and (+)-α-pinene, CYP6DE1 produced trans-verbenol with an enantiomeric profile that was similar to that produced by female MPB exposed to the α-pinene enantiomers.

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Monoterpenyl esters in juvenile mountain pine beetle and sex-specific release of the aggregation pheromone trans -verbenol

Cited by 47 publications

References 47 publications

Oleoresin defenses in conifers: chemical diversity, terpene synthases and limitations of oleoresin defense under climate change

Oleoresin defenses in conifers: chemical diversity, terpene synthases and limitations of oleoresin defense under climate change

Molecular evolution of gland cell types and chemical interactions in animals

The cytochrome P450 CYP6DE1 catalyzes the conversion of α-pinene into the mountain pine beetle aggregation pheromone trans-verbenol

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