Antifeedant Activity of Some Polygodial Derivatives

Moreno‐Osorio, Luis; Cortés, Manuel; Armstrong, Verónica; Bailén, María; González-Coloma⊥, Azucena

doi:10.1515/znc-2008-3-410

Cited by 27 publications

(28 citation statements)

References 23 publications

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“…The fluorinated 12-nordrimane 11 and the non-fluorinated drimane 22 (see Scheme 3) showed sufficient antifeedant activity against S. littoralis to carry out dose-response experiments [percent feeding reduction (%FR) Ͼ 65], whereas 19 and 51 (the epoxidation product of methyl albicanate) had significant moderate effects, with activity levels similar to polygodial (6). [62] The effective antifeedant doses calculated for the four compounds were quite similar (EC 50 values between 3.6 and 4.0 µg/cm 2 ). Most of the compounds tested had significant effects (p Ͻ 0.05, Wilcoxon signed rank test) on the settling behaviour of both aphid species.…”

Section: Evaluation Of Antifeedant Activitymentioning

confidence: 99%

“…These three fluorinated compounds had similar or better antisettling activity towards R. Padi than polygodial, but with significantly narrower confidence levels. [62] Furthermore, none of these compounds exhibited phytotoxic effects when applied to the leaf surface.…”

Section: Evaluation Of Antifeedant Activitymentioning

confidence: 99%

“…[62] Family-and/or species-related differences in the drimane molecular target have been suggested. [63] Several structure-activity trends can be deduced from the antifeedant effect of the test compounds on R. Padi.…”

Section: Evaluation Of Antifeedant Activitymentioning

confidence: 99%

“…Similarly, previous results have shown the importance of the C-9 substituents on the antifeedant effects of drimanes. [62,63] Oral cannulation of S. littoralis L6 larvae showed that the non-fluorinated derivatives 19 and 51 were moderate post-ingestive antifeedants whereas the fluorinated derivative of 19 (i.e., 11) was toxic (pANCOVA2 Ͻ 0.05, see the Supporting Information). Post-ingestive effects against this insect have been reported for 3β-hydroxycinnamolide and 3β-acetoxydrimenin [64] and suggested for synthetic analogues (lactones) of polygodial (6) and warburganal (7) on Pieris brassicae and L. decemlineata larvae.…”

Section: Evaluation Of Antifeedant Activitymentioning

confidence: 99%

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Preparation of 9α‐Fluorinated Sesquiterpenic Drimanes and Evaluation of Their Antifeedant Activities

Abad¹,

Agulló²,

Cuñat³

et al. 2010

Eur J Org Chem

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The preparation of 9α‐fluoro analogues of both natural and unnatural drimane‐type sesquiterpenes is described. Their synthesis began with the initial preparation of methyl 8‐keto‐12‐nordriman‐11‐oate from β‐ionone and entailed the electrophilic fluorination of C‐9 for the stereoselective introduction of the fluorine atom. The drimane skeleton was completed from the intermediate 9α‐fluoro‐8‐keto‐12‐nordrimane system by means of different reactions at the C‐8 ketone carbonyl group, essentially Wittig methylenation, cyanohydrin formation or palladium‐catalysed carbonylation of the corresponding enol triflate. Further manipulation of the functionalization derived from these key reactions allowed the preparation, among others, of 9α‐fluorodrimanes, which are structurally and functionally related to albicanic acid, drimenin and olepupuane. Also described are the reactivities of some of the fluorine‐containing systems prepared and a comparative study of the antifeedant activities of a selection of 9α‐fluorodrimanes and the corresponding hydrogen analogues against several insect species with different feeding ecologies (Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi), which revealed a significant increase in the antifeedant activities of some of the fluorinated drimane analogues.

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Section: Evaluation Of Antifeedant Activitymentioning

confidence: 99%

Section: Evaluation Of Antifeedant Activitymentioning

confidence: 99%

Section: Evaluation Of Antifeedant Activitymentioning

confidence: 99%

Section: Evaluation Of Antifeedant Activitymentioning

confidence: 99%

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Preparation of 9α‐Fluorinated Sesquiterpenic Drimanes and Evaluation of Their Antifeedant Activities

Abad¹,

Agulló²,

Cuñat³

et al. 2010

Eur J Org Chem

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“…Additionally, the biological activities of the crude oils were compared to that evaluated to sesquiterpene polygodial, which is the main constituent from the stem bark of Drimys species and responsible from the pharmacological effects for the extracts prepared from these plants. 3,7,16,17 However, the potential observed to the analyzed oils could contribute to explain the popular use of bark infusion of D. brasiliensis to the pain treatment, since the components of the essential oils also showed anti-inflammatory effects. …”

mentioning

confidence: 99%

Chemical composition and anti-inflammatory evaluation of essential oils from leaves and stem barks from Drimys brasiliensis Miers (Winteraceae)

Lago¹,

Carvalho²,

Silva³

et al. 2010

J. Braz. Chem. Soc.

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Os óleos essenciais das folhas e das cascas do tronco de Drimys brasiliensis Miers (Winteraceae) foram obtidos individualmente por hidrodestilação e suas composições químicas foram determinadas através de análise por CG/DIC e CG/EM. Os principais constituintes identificados foram monoterpenos (folhas 4,31% e cascas do tronco 90,02%) e sesquiterpenos (folhas 52,31% e cascas do tronco 6,35%). Adicionalmente, o sesquiterpeno poligodial foi isolado do extrato em hexano das cascas do tronco de D. brasiliensis após fracionamento cromatográfico e caracterizado por métodos espectroscópicos. Visando a avaliação do potencial anti-inflamatório, os óleos essenciais brutos e o sesquiterpeno poligodial foram submetidos à bioensaios para avaliação da toxicidade aguda destes compostos bem como das atividades anti-inflamatória e antinociceptiva induzidas por carragenina e formalina em ratos. Nossos resultados mostraram que o óleo essencial bruto obtido das cascas do tronco reduziu significativamente o edema induzido por carragenina. O efeito anti-inflamatório induzido pelo óleo das cascas do tronco (a 200 mg kg -1 ) foi similar ao observado para indometacina (a 10 mg kg -1 ) e superior ao poligodial (a 200 mg kg -1 ) em 30 e em 60 min após administração. A resposta inflamatória induzida pela formalina foi efetiva para o óleo das cascas do tronco (62,5%) em comparação ao poligodial (50,0%).The essential oils from leaves and stem barks from Drimys brasiliensis Miers (Winteraceae) were individually obtained by hydrodistillation and their compounds characterized by use of GC/FID and GC/MS. The main identified derivatives were monoterpenes (leaves 4.31% and stem barks 90.02%) and sesquiterpenes (leaves 52.31% and stem barks 6.35%). Additionally, the sesquiterpene polygodial was isolated from hexane extract from stem barks of D. brasiliensis after chromatographic steps and characterized by spectroscopic means, mainly NMR. Aiming the evaluation of anti-inflammatory potential, the crude essential oils and the sesquiterpene polygodial were subjected to bioassays to evaluate the acute toxicity of these compounds as well as the anti-inflammatory and antinociceptive activities induced by carrageenan and formalin in mices. Ours results showed that essential oil obtained from the stem barks significantly reduced the oedema induced by carrageenan. The anti-inflammatory effect induced by stem barks oil (at 200 mg kg -1 ) was similar to observed for indomethacin (at 10 mg kg -1 ) and superior for polygodial (at 200 mg kg -1 ) in 30 and 60 min after the administration of essential oils. The inflammatory response induced by formalin was effective to the stem barks oil (62.5%) in comparison to polygodial (50.0%).Keywords: Drimys brasiliensis Miers, essential oil composition, antinociceptive, antiinflammatory, acute toxicity IntroductionDrimys brasiliensis Miers belongs to Winteraceae family, whose occurrence is restrict to South America. This species is known in Brazil with a vernacular name "cascad'anta" and has been used in folk medicine as analg...

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Biochemistry of Terpenoids: Monoterpenes, Sesquiterpenes and Diterpenes

Ashour¹,

Wink²,

Gershenzon³

et al. 2018

Annual Plant Reviews Online

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Terpenoids represent the largest class of secondary metabolites and usually do not contain nitrogen or sulfur in their structures. Many terpenoids serve as defence compounds against microbes and herbivores and/or are signal molecules to attract pollinating insects, fruit‐dispersing animals or predators which can destroy insect herbivores. As a consequence, many terpenoids have pronounced pharmacological activities and are therefore interesting for medicine and biotechnology. The first part of the biosynthesis is the generation of a C5 unit, such as isopentenyl diphosphate (IPP) or dimethylallyl diphosphate (DMAPP). Two independent pathways have been discovered that can produce the C5 unit: the mevalonate and the methylerythritol phosphate (MEP) pathway. Depending on the number of C5 units, we distinguish hemiterpenes C5, monoterpenes including iridoids (C10), sesquiterpenes (C15), diterpenes (C20), sesterterpenes (C25), triterpenes (including steroids) (C30), tetraterpenes (C40) and polyterpenes (>C40). The biosynthesis (including enzymes, genes and their regulation) of mevalonate and the methylerythritol phosphate pathway and the consecutive pathways leading to mono‐, sesqui‐ and diterpenes are discussed in this chapter in detail.

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Antifeedant Activity of Some Polygodial Derivatives

Cited by 27 publications

References 23 publications

Preparation of 9α‐Fluorinated Sesquiterpenic Drimanes and Evaluation of Their Antifeedant Activities

Preparation of 9α‐Fluorinated Sesquiterpenic Drimanes and Evaluation of Their Antifeedant Activities

Chemical composition and anti-inflammatory evaluation of essential oils from leaves and stem barks from Drimys brasiliensis Miers (Winteraceae)

Biochemistry of Terpenoids: Monoterpenes, Sesquiterpenes and Diterpenes

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