Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants

Degenhardt, Jörg; Köllner, Tobias G.; Gershenzon, Jonathan

doi:10.1016/j.phytochem.2009.07.030

Cited by 870 publications

(831 citation statements)

References 170 publications

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“…Terpene synthases, for example, frequently produce many different products from a single substrate (e.g., Degenhardt et al, 2009), while methyltransferases and acyltransferases involved in the formation of volatile esters often accept several alcohols as substrates (Effmert et al, 2005;D'Auria, 2006). Thus, using a limited number of different enzymes, plants are able to produce complex volatile blends comprising dozens of compounds.…”

Section: Cyp79d6v3 and Cyp79d7v2 Have Broad Substrate Specificity Andmentioning

confidence: 99%

Two Herbivore-Induced Cytochrome P450 Enzymes CYP79D6 and CYP79D7 Catalyze the Formation of Volatile Aldoximes Involved in Poplar Defense

et al. 2013

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Aldoximes are known as floral and vegetative plant volatiles but also as biosynthetic intermediates for other plant defense compounds. While the cytochrome P450 monooxygenases (CYP) from the CYP79 family forming aldoximes as biosynthetic intermediates have been intensively studied, little is known about the enzymology of volatile aldoxime formation. We characterized two P450 enzymes, CYP79D6v3 and CYP79D7v2, which are involved in herbivore-induced aldoxime formation in western balsam poplar (Populus trichocarpa). Heterologous expression in Saccharomyces cerevisiae revealed that both enzymes produce a mixture of different aldoximes. Knockdown lines of CYP79D6/7 in gray poplar (Populus 3 canescens) exhibited a decreased emission of aldoximes, nitriles, and alcohols, emphasizing that the CYP79s catalyze the first step in the formation of a complex volatile blend. Aldoxime emission was found to be restricted to herbivore-damaged leaves and is closely correlated with CYP79D6 and CYP79D7 gene expression. The semi-volatile phenylacetaldoxime decreased survival and weight gain of gypsy moth (Lymantria dispar) caterpillars, suggesting that aldoximes may be involved in direct defense. The wide distribution of volatile aldoximes throughout the plant kingdom and the presence of CYP79 genes in all sequenced genomes of angiosperms suggest that volatile formation mediated by CYP79s is a general phenomenon in the plant kingdom.

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Section: Cyp79d6v3 and Cyp79d7v2 Have Broad Substrate Specificity Andmentioning

confidence: 99%

Two Herbivore-Induced Cytochrome P450 Enzymes CYP79D6 and CYP79D7 Catalyze the Formation of Volatile Aldoximes Involved in Poplar Defense

et al. 2013

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“…2 Noncovalent interactions, such as cation-π stabilization and steric repulsion, dictate the conformations of intermediates and resulting product distributions. 3,4 Although terpene synthases can be highly selective, product distributions containing multiple species are common. Contingent on the nature of the enzyme's active site, these intermediates may undergo eventual deprotonation or nucleophilic capture (e.g.…”

Section: Introductionmentioning

confidence: 99%

“…While limonene is obtained through a deprotonation route, capture of the α-terpinyl cation with water affords α-terpineol. 4,[5][6][7] Scheme 2. Encapsulation of 2 by host 1; spheres represent a Ga 3+ center and bisbidentate ligands are depicted as lines.…”

Section: Introductionmentioning

confidence: 99%

Selective Monoterpene-like Cyclization Reactions Achieved by Water Exclusion from Reactive Intermediates in a Supramolecular Catalyst

et al. 2012

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A polyanionic supramolecular assembly (1) is shown to catalytically cyclize the monoterpene citronellal and two homologues. In contrast to cyclization in acidic aqueous solution, the hydrophobic interior of 1 prevents the capture of reactive intermediates by water. This effect was also observed in the gold-catalyzed cycloisomerization of an enyne. Due to the steric confinement of the catalyst's interior, Prins cyclizations in 1 proceed cleanly both for substrates containing and lacking gem-dimethyl substitution. Encapsulation in 1 consequently imposes a degree of mechanistic control that, similar to enzyme catalysis, is not observed in bulk aqueous solution.

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“…Terpene synthases were first identified in tobacco (Nicotiana tabacum) [69] and spearmint (Mentha spicata) [70], and subsequently in numerous other plants including Arabidopsis thaliana, Citrus spp., Abies grandis, and Zea mays (for a detailed review, see [71]). To date, only three terpene synthase genes (including limonene, linalool, and bergamotene synthases) have been cloned and biochemically characterized in lavender.…”

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confidence: 99%

Biosynthesis and Therapeutic Properties ofLavandulaEssential Oil Constituents

Woronuk

Demissie²,

Rheault³

et al. 2010

Planta Med

179

122

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Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants

Cited by 870 publications

References 170 publications

Two Herbivore-Induced Cytochrome P450 Enzymes CYP79D6 and CYP79D7 Catalyze the Formation of Volatile Aldoximes Involved in Poplar Defense

Two Herbivore-Induced Cytochrome P450 Enzymes CYP79D6 and CYP79D7 Catalyze the Formation of Volatile Aldoximes Involved in Poplar Defense

Selective Monoterpene-like Cyclization Reactions Achieved by Water Exclusion from Reactive Intermediates in a Supramolecular Catalyst

Biosynthesis and Therapeutic Properties ofLavandulaEssential Oil Constituents

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