Frontalin pheromone biosynthesis in the mountain pine beetle,
            <i>Dendroctonus ponderosae</i>
            , and the role of isoprenyl diphosphate synthases

Keeling, Christopher I.; Chiu, Catherine; Aw, Tidiane; Li, Maria; Henderson, Hannah; Tittiger, Claus; Weng, Huan-Xin; Blomquist, Gary J.; Bohlmann, Jöerg

doi:10.1073/pnas.1316498110

Cited by 40 publications

(32 citation statements)

References 35 publications

(53 reference statements)

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“…It was previously shown that product chain length or activity of plant and insect IDSs can be influenced by heterooligomerization, which may also play a role in (E)-GPP and (Z,E)-FPP synthesis in P. striolata (9,(39)(40)(41). Moreover, IDS product chain length may also be influenced by the IPP/DMAPP ratio (8), and different metal ion cofactors as recently demonstrated in the mustard leaf beetle, Phaedon cochleariae (5). The putative role of PsIDS and PsIDS-like enzymes in the biosynthesis of (Z,E)-FPP are subjects of ongoing research.…”

Section: P Striolata Possesses An Evolutionarily Novel Class Of Tps mentioning

confidence: 93%

“…The number of introns per gene ranged from three introns present in genes of P. striolata and T. castaneum to seven introns in the GPPS/FPPS gene of D. ponderosae (8) (Fig. S7).…”

Section: Significancementioning

confidence: 99%

“…Sesquiterpenes are biosynthesized from three C 5 isopentenoid units supplied by the mevalonate pathway, which are then joined sequentially via the action of enzymes known as trans-isoprenyl diphosphate synthases (trans-IDS) to produce the linear C 15 intermediate (E,E)-farnesyl diphosphate (FPP). Trans-IDS enzymes have been identified and characterized in a number of insect species (4)(5)(6)(7)(8)(9)(10). The huge diversity of sesquiterpene carbon skeletons are formed from FPP in the next step by the catalysis of terpene synthases (TPSs).…”

mentioning

confidence: 99%

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Novel family of terpene synthases evolved from trans -isoprenyl diphosphate synthases in a flea beetle

Beran

Rahfeld

Luck

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

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Sesquiterpenes play important roles in insect communication, for example as pheromones. However, no sesquiterpene synthases, the enzymes involved in construction of the basic carbon skeleton, have been identified in insects to date. We investigated the biosynthesis of the sesquiterpene (6R,7S)-himachala-9,11-diene in the crucifer flea beetle Phyllotreta striolata, a compound previously identified as a male-produced aggregation pheromone in several Phyllotreta species. A (6R,7S)-himachala-9,11-diene–producing sesquiterpene synthase activity was detected in crude beetle protein extracts, but only when (Z,E)-farnesyl diphosphate [(Z,E)-FPP] was offered as a substrate. No sequences resembling sesquiterpene synthases from plants, fungi, or bacteria were found in the P. striolata transcriptome, but we identified nine divergent putative trans-isoprenyl diphosphate synthase (trans-IDS) transcripts. Four of these putative trans-IDSs exhibited terpene synthase (TPS) activity when heterologously expressed. Recombinant PsTPS1 converted (Z,E)-FPP to (6R,7S)-himachala-9,11-diene and other sesquiterpenes observed in beetle extracts. RNAi-mediated knockdown of PsTPS1 mRNA in P. striolata males led to reduced emission of aggregation pheromone, confirming a significant role of PsTPS1 in pheromone biosynthesis. Two expressed enzymes showed genuine IDS activity, with PsIDS1 synthesizing (E,E)-FPP, whereas PsIDS3 produced neryl diphosphate, (Z,Z)-FPP, and (Z,E)-FPP. In a phylogenetic analysis, the PsTPS enzymes and PsIDS3 were clearly separated from a clade of known coleopteran trans-IDS enzymes including PsIDS1 and PsIDS2. However, the exon–intron structures of IDS and TPS genes in P. striolata are conserved, suggesting that this TPS gene family evolved from trans-IDS ancestors.

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Section: P Striolata Possesses An Evolutionarily Novel Class Of Tps mentioning

confidence: 93%

“…The number of introns per gene ranged from three introns present in genes of P. striolata and T. castaneum to seven introns in the GPPS/FPPS gene of D. ponderosae (8) (Fig. S7).…”

Section: Significancementioning

confidence: 99%

mentioning

confidence: 99%

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Novel family of terpene synthases evolved from trans -isoprenyl diphosphate synthases in a flea beetle

Beran

Rahfeld

Luck

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

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“…Another scIDS from Dendroctonus spp. bark beetles produced C 10 -GDP and C 15 -farnesyl diphosphate (C 15 -FDP) depending on the C 5 -IDP/C 5 -DMADP substrate ratio [79][80][81]. Bifunctionality was also observed from the scIDSs characterized from different aphid species [83][84][85][86][87].…”

Section: Iridoid De Novo Synthesis: Early Stepsmentioning

confidence: 99%

“…Strikingly, most of them have the ability to form multiple products. For example, an enzyme studied from the bark beetle, Ips pini, displayed prenyltransferase and terpene synthase activity [79][80][81], resulting in the formation of precursors for the de novo synthesis of monoterpenoid aggregation pheromones such as ipsdienol, which coordinates the colonization of coniferous trees [82]. Another scIDS from Dendroctonus spp.…”

Section: Iridoid De Novo Synthesis: Early Stepsmentioning

confidence: 99%

Deciphering the route to cyclic monoterpenes in Chrysomelina leaf beetles: source of new biocatalysts for industrial application?

Burse

Boland

2017

Zeitschrift Für Naturforschung C

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Abstract:The drastic growth of the population on our planet requires the efficient and sustainable use of our natural resources. Enzymes are indispensable tools for a wide range of industries producing food, pharmaceuticals, pesticides, or biofuels. Because insects constitute one of the most species-rich classes of organisms colonizing almost every ecological niche on earth, they have developed extraordinary metabolic abilities to survive in various and sometimes extreme habitats. Despite this metabolic diversity, insect enzymes have only recently generated interest in industrial applications because only a few metabolic pathways have been sufficiently characterized. Here, we address the biosynthetic route to iridoids (cyclic monoterpenes), a group of secondary metabolites used by some members of the leaf beetle subtribe Chrysomelina as defensive compounds against their enemies. The ability to produce iridoids de novo has also convergently evolved in plants. From plant sources, numerous pharmacologically relevant structures have already been described. In addition, in plants, iridoids serve as building blocks for monoterpenoid indole alkaloids with broad therapeutic applications. As the commercial synthesis of iridoidbased drugs often relies on a semisynthetic approach involving biocatalysts, the discovery of enzymes from the insect iridoid route can account for a valuable resource and economic alternative to the previously used enzymes from the metabolism of plants. Hence, this review illustrates the recent discoveries made on the steps of the iridoid pathway in Chrysomelina leaf beetles. The findings are also placed in the context of the studied counterparts in plants and are further discussed regarding their use in technological approaches.

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Function of mevalonate pathway genes in the synthesis of frontalin in Chinese white pine beetle,Dendroctonus armandi(curculionidae: Scolytinae)

Sun

Kang

et al. 2021

Arch Insect Biochem Physiol

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The Chinese white pine beetle (Dendroctonus armandi Tsai and Li) is a significant pest of pine forests in the Qinling and Bashan Mountains of China. Adult males commonly produce frontalin using precursors synthesized through the mevalonate pathway, which is regulated by juvenile hormone III (JHIII). In this study, the expression levels of mevalonate pathway genes were quantified after phloem feeding and topical application of the JHIII solution. The frontalin was quantified by gas chromatography-mass spectrometry. Both the phloem feeding and JHIII treatments produced an evident upregulation in the male gut, mainly in 3-hydroxy-3methylglutaryl-CoA synthase (HMGS) and 3-hydroxy-3methylglutaryl-CoA reductase (HMGR). Moreover, HMGS, HMGR, isopentenyl diphosphate isomerase, and geranyl diphosphate synthase/farnesyl diphosphate synthase were upregulated in fed and JHIII-stimulated males of D. armandi under both conditions (solitary and paired). The expression levels were higher in paired compared to solitary males.Males had higher expression levels compared with females. Correspondingly, the phloem-feeding males produced more frontalin than JHIII-treated males, and the production of frontalin was higher in paired males than in solitary males. The knockdown of mevalonate pathway genes using RNAi in vivo effectively reduced the messenger RNA level of these genes and inhibited the production of frontalin. Among them, the silencing of HMGR or HMGS genes reduced the synthesis of frontalin most significantly.

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Frontalin pheromone biosynthesis in the mountain pine beetle, Dendroctonus ponderosae , and the role of isoprenyl diphosphate synthases

Cited by 40 publications

References 35 publications

Novel family of terpene synthases evolved from trans -isoprenyl diphosphate synthases in a flea beetle

Novel family of terpene synthases evolved from trans -isoprenyl diphosphate synthases in a flea beetle

Deciphering the route to cyclic monoterpenes in Chrysomelina leaf beetles: source of new biocatalysts for industrial application?

Function of mevalonate pathway genes in the synthesis of frontalin in Chinese white pine beetle,Dendroctonus armandi(curculionidae: Scolytinae)

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