Comparative antifeedant activities of polygodial and pyrethrins against whiteflies (<i>Bemisia tabaci</i>) and aphids (<i>Myzus persicae</i>)

Prota, Neli; Bouwmeester, Harro J.; Jongsma, Maarten A.

doi:10.1002/ps.3610

Cited by 22 publications

(18 citation statements)

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“…The 6‐h time point was selected as the most reliable because most insects were actively feeding at that time, and the time for induction of potentially confounding secondary responses resulting from the applied compound was kept to a minimum. The feeding preference was assessed using the antifeedant index (AI) and compared with the published data for polygodial (AI%) (Kutas and Nádasy, ; Prota et al ., ). The AI% of cinnamolide increased with increasing concentration applied, as seen in Figure , meaning that there was a clear dose‐dependent preference for the control discs over the treated ones, similar to what was observed for polygodial.…”

Section: Resultsmentioning

confidence: 97%

“…Cinnamolide has been identified in Cinnamosma fragrans and in the stem bark of Warburgia ugandensis , and was reported to exhibit antifungal activity (Wube et al ., ). Here we demonstrate that cinnamolide can also act as an antifeedant for both the silverleaf whitefly Bemisia tabaci and the green peach aphid Myzus persicae (Figure ), although it is not as strong as polygodial, with ED 50 values of 25 versus 195 μg gFW −1 and 54 vesus 423 μg gFW −1 , respectively (Prota et al ., ).…”

Section: Discussionmentioning

confidence: 97%

“…The best known drimane dialdehyde is polygodial, a compound with a pungent taste to mammals (Kubo and Ganjian, 1981;Escalera et al, 2008). In plants, polygodial has been shown to act as antifeedant against a number of herbivorous insects (Jansen and de Groot, 2004;Prota et al, 2013). The most common plant in which polygodial occurs is water-pepper, Persicaria hydropiper (formerly Polygonum hydropiper) (Starkenmann et al, 2006;Prota et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

“…Effect of increasing concentrations of cinnamolide on the feeding behaviour of Bemisia tabaci and Myzus persicae at 6 h from the start of the experiment compared with published results for polygodial(Prota et al, 2013).Antifeedant index (AI%) = [(C À T)/(C + T)] 9 100. Positive values indicate an antifeedant effect, negative values a phagostimulant effect.…”

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confidence: 99%

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Identification of a drimenol synthase and drimenol oxidase from Persicaria hydropiper, involved in the biosynthesis of insect deterrent drimanes

et al. 2017

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SUMMARYThe sesquiterpenoid polygodial, which belongs to the drimane family, has been shown to be an antifeedant for a number of herbivorous insects. It is presumed to be synthesized from farnesyl diphosphate via drimenol, subsequent C-12 hydroxylation and further oxidations at both C-11 and C-12 to form a dialdehyde. Here, we have identified a drimenol synthase (PhDS) and a cytochrome P450 drimenol oxidase (PhDOX1) from Persicaria hydropiper. Expression of PhDS in yeast and plants resulted in production of drimenol alone. Co-expression of PhDS with PhDOX1 in yeast yielded drimendiol, the 12-hydroxylation product of drimenol, as a major product, and cinnamolide. When PhDS and PhDOX1 were transiently expressed by agro-infiltration in Nicotiana benthamiana leaves, drimenol was almost completely converted into cinnamolide and several additional drimenol derivatives were observed. In vitro assays showed that PhDOX1 only catalyses the conversion from drimenol to drimendiol, and not the further oxidation into an aldehyde. In yeast and heterologous plant hosts, the C-12 position of drimendiol is therefore likely to be further oxidized by endogenous enzymes into an aldehyde and subsequently converted to cinnamolide, presumably by spontaneous hemiacetal formation with the C-11 hydroxyl group followed by oxidation. Purified cinnamolide was confirmed by NMR and shown to be deterrent with an effective deterrent dose (ED 50 ) of about 200-400 lg g À1 fresh weight against both whiteflies and aphids. The putative additional physiological and biochemical requirements for polygodial biosynthesis and stable storage in plant tissues are discussed.

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Section: Resultsmentioning

confidence: 97%

Section: Discussionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

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Identification of a drimenol synthase and drimenol oxidase from Persicaria hydropiper, involved in the biosynthesis of insect deterrent drimanes

et al. 2017

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“…Polygodial was found to be active antifeedant against a variety of aphids ( Aphis craccivora , Myzus persicae , and Rhopalosiphum padi ), African or Egyptian cotton leafworm ( Spodoptera littoralis ), and whiteflies ( Bemisia tabaci ) [67–70]. …”

Section: Pharmacological Propertiesmentioning

confidence: 99%

Ethnobotanical, Phytochemical, Pharmacological, and Toxicological Aspects ofPersicaria hydropiper(L.) Delarbre

Huq

Jamal

Stanslas

2014

Evidence-Based Complementary and Alternative Medicine

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Persicaria hydropiper (L.) Delarbre, belonging to Polygonaceae family, is a common weed found in most of the temperate countries including Bangladesh, China, Malaysia, and Japan. The plant is also referred to as “marsh pepper” or “smart weed.” It appears to be a useful herb with evidence-based medicinal properties. The present work addresses the botanical description, traditional uses, phytochemistry, pharmacology, and toxicology of P. hydropiper. All plant parts have been commonly used in the traditional systems of medicines. Flavonoids are the major group of phytochemical components followed by drimane-type sesquiterpenes and sesquiterpenoids, as well as phenylpropanoids. Different extracts and plant parts showed remarkable pharmacological activities including antioxidant, antibacterial, antifungal, antihelminth, antifeedant, cytotoxicity, anti-inflammatory, antinociceptive, oestrogenicity, antifertility, antiadipogenicity, and neuroprotection. Mutagenicity and acute and subchronic toxicities of the plant were also reported. P. hydropiper has tremendous medicinal properties that could further be investigated for the development of evidence-based herbal products.

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Antifeedant effect of polygodial and drimenol derivatives against Spodoptera frugiperda and Epilachna paenulata and quantitative structure‐activity analysis

Montenegro

Corral

Napal

et al. 2018

Pest Management Science

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The results suggest that drimanic compounds have potential as new agents against S. frugiperda and E. paenulata. A quantitative structure-activity relationship (QSAR) analysis of the whole series, supported by electronic studies, suggested that drimanic compounds have structural features necessary for increasing antifeedant activity, namely a C-9 carbonyl group and an epoxide at C-8 and C-9. © 2018 Society of Chemical Industry.

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Comparative antifeedant activities of polygodial and pyrethrins against whiteflies (Bemisia tabaci) and aphids (Myzus persicae)

Cited by 22 publications

References 57 publications

Identification of a drimenol synthase and drimenol oxidase from Persicaria hydropiper, involved in the biosynthesis of insect deterrent drimanes

Identification of a drimenol synthase and drimenol oxidase from Persicaria hydropiper, involved in the biosynthesis of insect deterrent drimanes

Ethnobotanical, Phytochemical, Pharmacological, and Toxicological Aspects ofPersicaria hydropiper(L.) Delarbre

Antifeedant effect of polygodial and drimenol derivatives against Spodoptera frugiperda and Epilachna paenulata and quantitative structure‐activity analysis

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