Comparison of the chemical composition of three species of smartweed (genus Persicaria) with a focus on drimane sesquiterpenoids

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

doi:10.1016/j.phytochem.2014.10.001

Cited by 25 publications

(16 citation statements)

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“…In a previous study we analysed the chemical profile of three Persicaria species, P. hydropiper, Persicaria maculosa and Persicaria minor (Prota et al, 2014). Persicaria hydropiper was shown to produce by far the highest amounts of polygodial [6.2 mg g À1 fresh weight (FW) in flowers], while in P. maculosa only traces of polygodial were detected.…”

Section: Identification Of the Drimenol Synthase Gene Phdsmentioning

confidence: 99%

“…The most common plant in which polygodial occurs is water‐pepper, Persicaria hydropiper (formerly Polygonum hydropiper ) (Starkenmann et al ., ; Prota et al ., ). It was reported that P. hydropiper produces and stores polygodial in the leaves and flowerheads in specialized epidermal cavities called valvate or irritant glands (Hagendoorn et al ., ; Derita et al ., ; Prota et al ., ).…”

Section: Introductionmentioning

confidence: 99%

“…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). It was reported that P. hydropiper produces and stores polygodial in the leaves and flowerheads in specialized epidermal cavities called valvate or irritant glands (Hagendoorn et al, 1994;Derita et al, 2008;Prota et al, 2014).…”

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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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: Identification Of the Drimenol Synthase Gene Phdsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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“…Purified polygodial has been shown to have many different biological activities, including (but not limited to) fungitoxic, antibacterial, antiviral, piscicidal, molluscicidal, cytotoxic, antiallergic, anti‐inflammatory and antifeedant activity . This compound occurs in three plant families, the Polygonaceae, Cannellaceae and Winteraceae, and it has also been discovered in sponges and sea molluscs, where it most likely has a function as a feeding deterrent to natural enemies. In plants it is thought to act as a semiochemical, meaning that it acts by influencing insect behaviour rather than as a toxin .…”

Section: Introductionmentioning

confidence: 99%

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

Prota¹,

Bouwmeester²,

Jongsma³

2013

Pest Management Science

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“…Although some aphids produce oviparae under stressed conditions in summer (Hardie, 1985), it seems unlikely that these oviparae are a reliable or abundant enough source to sustain Chrysopa male pheromone production. Therefore, we further hypothesize the raison d'être that Asian Chrysopa eat fruit and foliage of silver leaf (A. polygama) is to obtain iridoid precursors necessary to make their pheromone; we believe that other iridoid-producing plants (e.g., Hilgraf et al, 2012;Prota et al, 2014) elsewhere in the world must be similarly usurped by male Chrysopa species to sequester iridoid pheromone precursors.…”

Section: Nomentioning

confidence: 91%

Pharmacophagy in green lacewings (Neuroptera: Chrysopidae:Chrysopaspp.)?

Aldrich¹

2016

2016 International Congress of Entomology

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Green lacewings (Neuroptera: Chrysopidae) are voracious predators of aphids and other small, soft-bodied insects and mites. Earlier, we identified (1R,2S,5R,8R)-iridodial from wild males of the goldeneyed lacewing, Chrysopa oculata Say, which is released from thousands of microscopic dermal glands on the abdominal sterna. Iridodial-baited traps attract C. oculata and other Chrysopa spp. males into traps, while females come to the vicinity of, but do not usually enter traps. Despite their healthy appearance and normal fertility, laboratory-reared C. oculata males do not produce iridodial. Surprisingly, goldeneyed lacewing males caught alive in iridodial-baited traps attempt to eat the lure and, in Asia, males of other Chrysopa species reportedly eat the native plant, Actinidia polygama (Siebold & Zucc.) Maxim. (Actinidiaceae) to obtain the monoterpenoid, neomatatabiol. These observations suggest that Chrysopa males must sequester exogenous natural iridoids in order to produce iridodial; we investigated this phenomenon in laboratory feeding studies. Lacewing adult males fed various monoterpenes reduced carbonyls to alcohols and saturated double bonds, but did not convert these compounds to iridodial. Only males fed the common aphid sex pheromone component, (1R,4aS,7S,7aR)-nepetalactol, produced (1R,2S,5R,8R)-iridodial. Furthermore, although C. oculata males fed the second common aphid sex pheromone component, (4aS,7S,7aR)-nepetalactone, did not produce iridodial, they did convert ∼75% of this compound to the corresponding dihydronepetalactone, and wild C. oculata males collected in early spring contained traces of this dihydronepetalactone. These findings are consistent with the hypothesis that Chrysopa males feed on oviparae (the late-season pheromone producing stage of aphids) to obtain nepetalactol as a precursor to iridodial. In the spring, however, wild C. oculata males produce less iridodial than do males collected later in the season. Therefore, we further hypothesize that Asian Chrysopa eat A. polygama to obtain iridoid precursors in order to make their pheromone, and that other iridoid-producing plants elsewhere in the world must be similarly usurped by male Chrysopa species to sequester pheromone precursors.

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Comparison of the chemical composition of three species of smartweed (genus Persicaria) with a focus on drimane sesquiterpenoids

Cited by 25 publications

References 29 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

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

Pharmacophagy in green lacewings (Neuroptera: Chrysopidae:Chrysopaspp.)?

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