Isolation and bacterial expression of a sesquiterpene synthase cDNA clone from peppermint (
 Mentha
 x
 piperita
 , L.) that produces the aphid alarm pheromone (
 E
 )-β-farnesene

Crock, John; Wildung, Mark R.; Croteau, Rodney

doi:10.1073/pnas.94.24.12833

Cited by 175 publications

(147 citation statements)

References 56 publications

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“…26 In peppermint, the only by-product (δ-cadinene) produced by (E)-b-farnesene synthase in the presence of Mg 2+ was entirely absent in the presence of Mn 2+ ions. 27 In addition, the formation of sesquiterpenes such as germacrenes D and B and bicyclogermacrene from farnesyl diphosphate by germacrene D synthase in ginger (Zingiber officinale Roscoe; Zingiberaceae) is favored with Mg 2+ as cofactor, but it is inactive in the presence of Cu 2+ ions. 28 Similar negative effects of foliar Mn on δ-cadinene and foliar Cu on germacrenes D and B, and bicyclogermacrene 1676 are in agreement with the negative correlation observed in this study.…”

Section: Resultsmentioning

confidence: 99%

Environmental influence on phenols and essential oils of Myrciaria cauliflora leaves

Duarte¹,

Santos²,

Seraphin³

et al. 2010

J. Braz. Chem. Soc.

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O conteúdo foliar de fenóis totais e de taninos, bem como a composição química dos óleos essenciais em populações de Myrciaria cauliflora cultivadas em seis diferentes sítios de amostragem indicou a presença de quatro grupos de amostras de acordo com as características químicas da folha e do solo de cultivo. O grupo I incluiu as amostras oriundas do solo franco-arenoso (S1), caracterizado pela maior e menor percentagem de g-eudesmol (11,55%) e germacreno D (20,48%), respectivamente, e alto conteúdo de fenóis totais (136,68 mg g -1 ) e taninos (60,72 mg g -1 ). O grupo II, rico em elemol (4,61%), incluiu as amostras cultivadas nos solos franco-arenoso-argilosos (S2, S3 e S6), enquanto que as amostras dos solos argilosos S4 (grupo III) e S5 (grupo IV) apresentaram as mais elevadas percentagens de germacreno D (III: 27,20%; IV: 26,83%) e os mais baixos teores de elemol (2,12-2,55%), fenóis totais (79,69 e 111,77 mg g -1 ) e taninos (34,04 e 44,51 mg g -1 ). A análise de redundância canônica revelou como o balanço de nutrientes do solo e das folhas influenciou a distribuição dos constituintes químicos nos diferentes agrupamentos. A variação química parece ser determinada por fatores ambientais.Foliar contents of total phenols and tannins and the essential oil composition of Myrciaria cauliflora populations cultivated in six sampling sites have shown the presence of four clusters related to soil types and foliar nutrients. Cluster I included samples which originated from sandy loam soil (S1) with the highest and lowest percentages of g-eudesmol (11.55%) and germacrene D (20.48%), respectively, as well as high total phenol (136.68 mg g -1 ) and tannin (60.72 mg g -1 ) contents. Cluster II, rich in elemol (4.61%), included all the samples cultivated from clay sand loam soils (S2, S3, and S6), whereas clay soils S4 (cluster III) and S5 (cluster IV) had the highest amounts of germacrene D (III: 27.20%; IV: 26.83%) and the lowest levels of elemol (2.12-2.55%), total phenols (79.69 and 111.77 mg g -1 ), and tannins (34.04 and 44.51 mg g -1 ). The canonical redundancy analysis revealed the relationship between chemical balances in the soil and leaf nutrients in different clusters. Chemovariations may be environmentally determined.Keywords: Myrciaria cauliflora, essential oil, phenol, chemical variability, environmental influence, multivariate analysis Introduction Jaboticaba, also known as guaperu or sabara, is a small native Brazilian fruit of the cauliflorus Myrtle (Myrtaceae). It is grape-like in appearance and texture, although its skin is thicker and tougher, and its color varies from grown to deep purple or black due to high anthocyanin content. 1 The ripened berries are highly perishable -postharvest decay occurs within 2-3 days -which is a problem for both transport and storage. 2 The plant is distributed in southern and central Brazilian regions and consists of about nine species of trees and shrubs, among which Myrciaria cauliflora (Mart.) O. Berg. and M. jaboticaba (Vell.) O. Berg. are the most widely cultivated ...

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Section: Resultsmentioning

confidence: 99%

Environmental influence on phenols and essential oils of Myrciaria cauliflora leaves

Duarte¹,

Santos²,

Seraphin³

et al. 2010

J. Braz. Chem. Soc.

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“…It has a relatively low level of endogenous terpene biosynthesis, and much is already known about its molecular genetics and terpene emission profile (20)(21)(22)(23)(24). A gene encoding an E␤f synthase has been cloned from Mentha ϫ piperita and functionally expressed in Escherichia coli (25,26). In the latter study (26), we found the in vitro product profile of the synthase to consist of essentially pure E␤f with no other detectable sesquiterpenes, and this gene was therefore considered to be ideal for engineering production of the aphid alarm pheromone into plants.…”

Section: Resultsmentioning

confidence: 99%

Aphid alarm pheromone produced by transgenic plants affects aphid and parasitoid behavior

Beale

Birkett

Bruce

et al. 2006

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

278

221

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The alarm pheromone for many species of aphids, which causes dispersion in response to attack by predators or parasitoids, consists of the sesquiterpene (E)-␤-farnesene (E␤f). We used high levels of expression in Arabidopsis thaliana plants of an E␤f synthase gene cloned from Mentha ؋ piperita to cause emission of pure E␤f. These plants elicited potent effects on behavior of the aphid Myzus persicae (alarm and repellent responses) and its parasitoid Diaeretiella rapae (an arrestant response). Here, we report the transformation of a plant to produce an insect pheromone and demonstrate that the resulting emission affects behavioral responses at two trophic levels.Diaeretiella rapae ͉ Myzus persicae ͉ semiochemical ͉ volatile ͉ farnesene

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“…L. esculentum cv. VFNT Cherry tomato plants (obtained as seed from John Steffens, Cornell University) were propagated from cuttings and grown under conditions as reported (11). L. esculentum cv.…”

Section: Methodsmentioning

confidence: 99%

Germacrene C synthase fromLycopersicon esculentumcv. VFNT Cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase

Colby

Crock

Dowdle-Rizzo

et al. 1998

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

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121

100

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Germacrene C was found by GC-MS and NMR analysis to be the most abundant sesquiterpene in the leaf oil of Lycopersicon esculentum cv. VFNT Cherry, with lesser amounts of germacrene A, guaia-6,9-diene, germacrene B, ␤-caryophyllene, ␣-humulene, and germacrene D. Soluble enzyme preparations from leaves catalyzed the divalent metal ion-dependent cyclization of [1-3 H]farnesyl diphosphate to these same sesquiterpene olefins, as determined by radio-GC. To obtain a germacrene synthase cDNA, a set of degenerate primers was constructed based on conserved amino acid sequences of related terpenoid cyclases. With cDNA prepared from leaf epidermis-enriched mRNA, these primers amplified a 767-bp fragment that was used as a hybridization probe to screen the cDNA library. Thirty-one clones were evaluated for functional expression of terpenoid cyclase activity in Escherichia coli by using labeled geranyl, farnesyl, and geranylgeranyl diphosphates as substrates. Nine cDNA isolates expressed sesquiterpene synthase activity, and GC-MS analysis of the products identified germacrene C with smaller amounts of germacrene A, B, and D. None of the expressed proteins was active with geranylgeranyl diphosphate; however, one truncated protein converted geranyl diphosphate to the monoterpene limonene. The cDNA inserts specify a deduced polypeptide of 548 amino acids (M r ‫؍‬ 64,114), and sequence comparison with other plant sesquiterpene cyclases indicates that germacrene C synthase most closely resembles cotton ␦-cadinene synthase (50% identity).

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Isolation and bacterial expression of a sesquiterpene synthase cDNA clone from peppermint ( Mentha x piperita , L.) that produces the aphid alarm pheromone ( E )-β-farnesene

Cited by 175 publications

References 56 publications

Environmental influence on phenols and essential oils of Myrciaria cauliflora leaves

Environmental influence on phenols and essential oils of Myrciaria cauliflora leaves

Aphid alarm pheromone produced by transgenic plants affects aphid and parasitoid behavior

Germacrene C synthase fromLycopersicon esculentumcv. VFNT Cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase

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