Natural sesquiterpenoids

Fraga, Braulio M.

doi:10.1039/b407376m

Cited by 44 publications

(16 citation statements)

References 255 publications

(273 reference statements)

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“…Plant species belonging to the family Asteraceae are known for their content of sesquiterpenes which have been reported to serve as toxic or feeding deterrents to insect herbivores. 46 In the present studies, two sesquiterpene lactones, alantolactone and isoalantolactone isolated from I. racemosa, exerted a growth-inhibiting effect on S. litura. Ingestion of 500-2000 ppm of alantolactone and 2000 ppm of isoalantolactone significantly prolonged the larval development.…”

Section: Discussionmentioning

confidence: 54%

Impact of sesquiterpenes from Inula racemosa (Asteraceae) on growth, development and nutrition of Spodoptera litura (Lepidoptera: Noctuidae)

Kaur

Kumar

Upendrabhai

et al. 2016

Pest Management Science

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Section: Discussionmentioning

confidence: 54%

Impact of sesquiterpenes from Inula racemosa (Asteraceae) on growth, development and nutrition of Spodoptera litura (Lepidoptera: Noctuidae)

Kaur

Kumar

Upendrabhai

et al. 2016

Pest Management Science

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“…Plant species belonging to the Asteraceae family are known for their content of sesquiterpenes, which have been reported to serve as toxic or feeding deterrents to herbivore insects (Fraga, 2004, Prasifka et al, 2015, Kaur et al, 2017). Botanical insecticides affect insect physiology in many different ways and at various receptor sites.…”

Section: Discussionmentioning

confidence: 99%

Insecticidal effects of Vernonanthura nebularum against two economically important pest insects

Sosa

Díaz

Salvatore

et al. 2019

Saudi Journal of Biological Sciences

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Vernonanthura nebularum (Cabrera) H. Rob. (Asteraceae), an endemic species from the north of Argentina, is a rich source of elephantopus-type sesquiterpene lactones. These compounds have proved to be promising antiparasitic agents, but there is no report about their action against pest insects. In this work we studied for the first time the antifeedant and toxic effects of V. nebularum natural products against the fall army warm Spodoptera frugiperda Smith and the oviposition deterrent activity against the fruit fly Ceratitis capitata Wiedemann. As a result, we found that extracts, fractions composed of sesquiterpene lactones and pure sesquiterpene lactones altered larval feeding behavior in the food choice test. Nutritional parameters of S . frugiperda larvae were also affected. Fraction II (300 μg/g of diet.), containing compounds 1 , 2 and 3 , was the most toxic substance with 80% pupal mortality and wing malformations in adults. In oviposition deterrent experiments against Ceratitis capitata , we observed a moderate effect at 30 μg/cm 2 of the test compound. The most active substances were the methanolic extract, dichloromethane subextract and lactone 2 . According to our results, V. nebularum natural products could be used for maximizing the effectiveness and specificity in future insecticide design with specific or multiple target sites, while ensuring the economic and ecological sustainability, in addition to combat the increasing resistance rates developed by synthetic pesticides.

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“…Many sesquiterpenes and their alcohol, aldehyde and ketone derivatives, are biologically active or precursors to metabolites with biological functions, while others have desirable fragrance, flavouring and medicinal properties. 1 For example the phytoalexin capsidiol is derived from the sesquiterpene 5epi-aristolochene, 2 and amorpha-4,11-diene is the precursor to the potent antimalarial compound artemisinin (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450BM-3

et al. 2005

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The sesquiterpenoids are a large class of naturally occurring compounds with biological functions and desirable properties. Oxidation of the sesquiterpene (+)-valencene by wild type and mutants of P450cam from Pseudomonas putida, and of P450BM-3 from Bacillus megaterium, have been investigated as a potential route to (+)-nootkatone, a fine fragrance. Wild type P450cam did not oxidise (+)-valencene but the mutants showed activities up to 9.8 nmol (nmol P450)(-1) min(-1), with (+)-trans-nootkatol and (+)-nootkatone constituting >85% of the products. Wild type P450BM-3 and mutants had higher activities (up to 43 min(-1)) than P450cam but were much less selective. Of the many products, cis- and trans-(+)-nootkatol, (+)-nootkatone, cis-(+)-valencene-1,10-epoxide, trans-(+)-nootkaton-9-ol, and (+)-nootkatone-13S,14-epoxide were isolated from whole-cell reactions and characterised. The selectivity patterns suggest that (+)-valencene has one binding orientation in P450cam but multiple orientations in P450BM-3.

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Natural sesquiterpenoids

Abstract: This review covers the isolation, structural determination, synthesis and chemical and microbiological transformations of natural sesquiterpenoids. The literature from January to December 2003 is reviewed, and 389 references are cited.

Cited by 44 publications

References 255 publications

Impact of sesquiterpenes from Inula racemosa (Asteraceae) on growth, development and nutrition of Spodoptera litura (Lepidoptera: Noctuidae)

Impact of sesquiterpenes from Inula racemosa (Asteraceae) on growth, development and nutrition of Spodoptera litura (Lepidoptera: Noctuidae)

Insecticidal effects of Vernonanthura nebularum against two economically important pest insects

Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450BM-3

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