Implication of HMGR in homeostasis of sequestered and de novo produced precursors of the iridoid biosynthesis in leaf beetle larvae

Burse, Antje; Frick, Stephanie; Schmidt, Axel; Buechler, Rita; Kunert, Maritta; Gershenzon, Jonathan; Brandt, Wolfgang; Boland, Wilhelm

doi:10.1016/j.ibmb.2007.09.006

Cited by 20 publications

(22 citation statements)

References 82 publications

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“…In insects, for example, it is known that HMGR transcription is affected by juvenile hormones [67,68]. From Chrysomelina beetles, we reported that HMGR is negatively regulated by 8-hydroxygeraniol, another intermediate of iridoid biosynthesis [69]. Purification of the catalytic HMGR domain revealed that inhibition by 8-hydroxygeraniol is subject to the catalytic domain, which was corroborated by docking analyses on the modeled HMGR catalytic portion.…”

Section: Iridoid De Novo Synthesis: Early Stepssupporting

confidence: 56%

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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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Section: Iridoid De Novo Synthesis: Early Stepssupporting

confidence: 56%

“…In P. cochleariae, the iridoid biosynthesis proceeds not entirely in the glands but it is most likely compartmented within the larval body [69]. After translocation of 8-hydroxygeraniol-O-β-d-glucoside into the defensive glands, its final transformation into iridoids occurs in the secretions.…”

Section: Iridoid De Novo Synthesis: Late 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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“…We assume variants of de novo biosynthesis or sequestration from food, as this has already been described for other insect species. [25,26] However, species-specific composition of pheromonal blends found in specimens from different localities, as well as comparison of wild and laboratory colonies, strongly supports the de novo hypothesis. For de novo biosynthesis of terpenes, 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase would be the key putative enzyme.…”

Section: Introductionmentioning

confidence: 56%

De Novo Biosynthesis of Sexual Pheromone in the Labial Gland of Bumblebee Males

et al. 2013

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De novo biosynthesis of male sex pheromone from two bumblebee species (Bombus terrestris and Bombus lucorum) was studied by using in vitro incubations of labial glands (LGs) with radioactive [1,2-(14)C]acetate and deuterated [D(3)]acetate. The labeled substrate was incorporated into several types of compounds, such as terpenic alcohols, fatty acids, esters, and hydrocarbons. A similar incubation of [1,2-(14)C]acetate with fat bodies (FB) led to the formation of fatty acids, triacylglycerols (TAG), and hydrocarbons. To support the results from in vitro incubations, PCR analysis of fatty acid synthase (FAS) transcripts in LG and FB was performed. Relative quantification of FAS transcription levels revealed that the abundance of mRNA from the FAS gene is a function of the age of B. terrestris males. A comparison of the relative FAS mRNA gene transcription level in FB and LGs of B. terrestris and B. lucorum males proved that high biosynthetic activity takes place in the LGs of both species. Together, these results indicate that pheromone components are synthesized de novo in the LG.

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“…The early steps leading to the formation of the intermediate 8-hydroxygeraniol-glucoside are most likely localized in the fat body tissue. The glucoside is then transferred from there via the hemolymph into the defense glands, where the later steps in formation of chrysomelidial are located (25) (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Metal ions control product specificity of isoprenyl diphosphate synthases in the insect terpenoid pathway

Frick¹,

Nagel

Schmidt

et al. 2013

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

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Isoprenyl diphosphate synthases (IDSs) produce the ubiquitous branched-chain diphosphates of different lengths that are precursors of all major classes of terpenes. Typically, individual shortchain IDSs (scIDSs) make the C 10 , C 15 , and C 20 isoprenyl diphosphates separately. Here, we report that the product length synthesized by a single scIDS shifts depending on the divalent metal cofactor present. This previously undescribed mechanism of carbon chainlength determination was discovered for a scIDS from juvenile horseradish leaf beetles, Phaedon cochleariae. The recombinant enzyme P. cochleariae isoprenyl diphosphate synthase 1 (PcIDS1) yields 96% C 10 -geranyl diphosphate (GDP) and only 4% C 15 -farnesyl diphosphate (FDP) in the presence of Co 2+ or Mn 2+ as a cofactor, whereas it yields only 18% C 10 GDP but 82% C 15 FDP in the presence of Mg 2+. In reaction with Co 2+ , PcIDS1 has a K m of 11.6 μM for dimethylallyl diphosphate as a cosubstrate and 24.3 μM for GDP. However, with Mg 2+ , PcIDS1 has a K m of 1.18 μM for GDP, suggesting that this substrate is favored by the enzyme under such conditions. RNAi targeting PcIDS1 revealed the participation of this enzyme in the de novo synthesis of defensive monoterpenoids in the beetle larvae. As an FDP synthase, PcIDS1 could be associated with the formation of sesquiterpenes, such as juvenile hormones. Detection of Co , or Mg 2+ in the beetle larvae suggests flux control into C 10 vs. C 15 isoprenoids could be accomplished by these ions in vivo. The dependence of product chain length of scIDSs on metal cofactor identity introduces an additional regulation for these branch point enzymes of terpene metabolism.cobalt | kinetic | prenyltransferase | secretions | silencing

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Implication of HMGR in homeostasis of sequestered and de novo produced precursors of the iridoid biosynthesis in leaf beetle larvae

Cited by 20 publications

References 82 publications

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

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

De Novo Biosynthesis of Sexual Pheromone in the Labial Gland of Bumblebee Males

Metal ions control product specificity of isoprenyl diphosphate synthases in the insect terpenoid pathway

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