Insight into the Mode of Action of Haedoxan A from Phryma leptostachya

Hu, Zhaonong; Du, Yuzhe; Xinmin, Xiao; Dong, Ke; Wu, Wenjun

doi:10.3390/toxins8020053

Cited by 15 publications

(20 citation statements)

References 45 publications

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“…3B-II and 3C-II). Consistent with the observations reported for cockroach sodium channels expressed in oocytes (Hu et al, 2016), we found that HA did not modify the voltage-dependent activation or recovery from fast and slow inactivation of either the wild-type DmNa v 22 or I265N mutant channels (Fig. 3A-II, 3D-II, and 3E-II).…”

Section: I265n Mutation Abolished the Ha-induced Hyperpolarizing Shif...supporting

confidence: 92%

“…Subsequently, we evaluated the effects of HA on DmNa v 22 channel function, and consistent with the results obtained in previous studies on cockroach sodium channels expressed in oocytes (Hu et al, 2016), we found that at a concentration of 3 μmol/L, HA induced hyperpolarizing shifts in the voltage dependence of both the fast and slow inactivation of DmNa v 22 channels . The voltage dependences of fast and slow inactivation were significantly shifted by 7.2 mV and 2.9 mV, respectively, in the hyperpolarizing direction.…”

Section: I265n Mutation Abolished the Ha-induced Hyperpolarizing Shif...supporting

confidence: 85%

“…Phryma leptostachya L. is an herbaceous perennial plant with a broad worldwide distribution, including the Himalayas, temperate regions of Asia, and northeastern America (Hu et al ., 2016), the active constituents of which have a long history of application as a traditional natural insecticide to control mosquitoes and flies (Lee et al ., 2002; Chen et al ., 2012). Since the 1960s, a series of compounds from P. leptostachya have been isolated, including phrymarolin I and II and haedoxan A (HA), which have shown considerable insecticidal or synergistic activity that merit further research (Taniguchi & Oshima, 1972a, b; Taniguchi et al ., 1989).…”

Section: Introductionmentioning

confidence: 99%

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Negative cross‐resistance of a pyrethroid‐resistant Drosophila mutant to Phryma leptostachya‐derived haedoxan A

Qie

Aioub

et al. 2021

Insect Science

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Voltage‐gated sodium channels are the primary target of pyrethroid insecticides. Mutations in sodium channel confer knockdown resistance (kdr) to pyrethroids in various arthropod pests. Haedoxan A (HA) is the major insecticidal component from Phryma leptostachya. It has been shown that HA alters electrical responses at the Drosophila neuromuscular junction and modifies the gating properties of cockroach sodium channels expressed in Xenopus oocytes. However, whether sodium channel mutations that confer pyrethroid resistance also affect the action of HA is unknown. In this study, we conducted bioassays using HA and permethrin in two Drosophila melanogaster strains: w1118, an insecticide‐susceptible strain, and parats1, a pyrethroid‐resistant strain due to a I265N mutation in the sodium channel, and identified a new case of negative cross‐resistance (NCR) between permethrin and HA. Both parats1 larvae and adults were more resistant to permethrin, as expected. However, both parats1 larvae and adults were more sensitive to HA compared to w1118. We confirmed that the I265N mutation reduced the sensitivity to permethrin of a Drosophila sodium channel variant, DmNav22, expressed in Xenopus oocytes. Interestingly, the I265N mutation also abolished the effect of HA on sodium channels. Further characterization showed that I265 on the sodium channels is critical for the action of both pyrethroids and HA on sodium channels, pointing to an overlapping mode of action between pyrethroids and HA on the sodium channel. Overall, our results suggest an I265N‐independnt mechanism(s) in parats1 flies that is responsible for the NCR between permethrin and HA at the whole insect level.

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Section: I265n Mutation Abolished the Ha-induced Hyperpolarizing Shif...supporting

confidence: 92%

Section: I265n Mutation Abolished the Ha-induced Hyperpolarizing Shif...supporting

confidence: 85%

Section: Introductionmentioning

confidence: 99%

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Negative cross‐resistance of a pyrethroid‐resistant Drosophila mutant to Phryma leptostachya‐derived haedoxan A

Qie

Aioub

et al. 2021

Insect Science

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“…Haedoxans exhibit excellent insecticidal activity against several insects, such as Musca domestica [Culex pipiens pallens (Xiao et al, 2012b)] and Mythimna separata (Xiao et al, 2012a). It is noteworthy that the insecticidal activity of Haedoxan A (1) is comparable to that of the commercial synthetic pyrethroids (Taniguchi et al, 1989;Hu et al, 2016). (+)-Phrymarolins I (4) and II (5) also show considerable synergistic activities with pyrethrin and carbamate pesticides (Park et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

A Synthetic View on Haedoxans and Related Neolignans From Phryma leptostachya

et al. 2020

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Haedoxans are a series of sesquilignan natural products isolated from the traditional insecticidal plant Phryma leptostachya. Given their significant insecticidal activity, haedoxans and related analogs have been considered as potential agents for plant defense. Moreover, these compounds also exhibit promising antifungal, antibacterial, and anticancer activities. The present paper is a review of the structure, biological activity, and chemical synthesis of naturally occurring haedoxan-like molecules.

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“…These lignans from P. leptostachya exhibited highly efficient insecticidal activities against a variety of pests [6,15,16], which aroused our interest. For example, haedoxan A displayed remarkably high insecticidal activity against the housefly, which was approximate with common synthetic pyrethroids [17,18,19,20].…”

Section: Introductionmentioning

confidence: 99%

Insecticidal Activity of Four Lignans Isolated from Phryma leptostachya

Wei

Fang

et al. 2019

Molecules

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A new lignan (T4) and three known lignans (T1, T2, and T3) were isolated from the methanol extract of the roots of Phryma leptostachya using bioassay-guided method, and their structures were identified as phrymarolin I (T1), II (T2), haedoxan A (T3), and methyl 4-((6a-acetoxy-4-(6-methoxybenzo[d][1,3]dioxol-5-yl)tetrahydro-1H,3H-furo[3,4–c]furan-1-yl)oxy)-1-hydroxy-2,2-dimethoxy-5-oxocyclopent-3-ene-1-carboxylate (T4) byNMR and ESI-MS spectral data. Bioassay results revealed that haedoxan A exhibited remarkably high insecticidal activity against Mythimna separata with a stomach toxicity LC50 value of 17.06 mg/L and a topical toxicity LC50 value of 1123.14 mg/L at 24 h, respectively. Phrymarolin I and compound T4 also showed some stomach toxicity against M. separata with KD50 values of 3450.21 mg/L at 4 h and 2807.10 mg/L at 8 h, respectively. In addition, phrymarolin I and haedoxan A exhibited some stomach toxicity against Plutella xylostella with an LC50 value of 1432.05 and 857.28 mg/L at 48 h, respectively. In conclusion, this study demonstrated that lignans from P. leptostachya are promising as a novel class of insecticides or insecticide lead compounds for developing botanical pesticides.

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Insight into the Mode of Action of Haedoxan A from Phryma leptostachya

Cited by 15 publications

References 45 publications

Negative cross‐resistance of a pyrethroid‐resistant Drosophila mutant to Phryma leptostachya‐derived haedoxan A

Negative cross‐resistance of a pyrethroid‐resistant Drosophila mutant to Phryma leptostachya‐derived haedoxan A

A Synthetic View on Haedoxans and Related Neolignans From Phryma leptostachya

Insecticidal Activity of Four Lignans Isolated from Phryma leptostachya

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