A potential lignan botanical insecticide from Phryma leptostachya against Aedes aegypti: laboratory selection, metabolic mechanism, and resistance risk assessment

Qie, Xingtao; Sun, Anqi; Hao, Huanhuan; Lv, Bo; Wu, Wenjun; Hu, Zhaonong

doi:10.1007/s10340-021-01389-w

Cited by 5 publications

(1 citation statement)

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“…Previous investigations have shown that the main insecticidal active ingredients in P. leptostachya are furofuran lignans [ 1 , 6 , 7 ]. For example, haedoxan A (HA) exhibits high insecticidal effectiveness against a wide variety of pests, like Culex pipiens pallens [ 7 ], Mythimna separata [ 4 ], Aedes albopictus , and Aedes aegypti [ 6 , 8 , 9 ]. ( +)-Phrymarolins I and II (( +)-P-I and P-II) have the same furofuran skeleton as HA and there is considerable synergistic activity between them and HA, pyrethrin, or carbamate pesticides [ 6 , 10 ].…”

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confidence: 99%

Identification and functional characterization of the dirigent gene family in Phryma leptostachya and the contribution of PlDIR1 in lignan biosynthesis

Pei

Cao

et al. 2023

BMC Plant Biol

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Background Furofuran lignans, the main insecticidal ingredient in Phryma leptostachya, exhibit excellent controlling efficacy against a variety of pests. During the biosynthesis of furofuran lignans, Dirigent proteins (DIRs) are thought to be dominant in the stereoselective coupling of coniferyl alcohol to form ( ±)-pinoresinol. There are DIR family members in almost every vascular plant, but members of DIRs in P. leptostachya are unknown. To identify the PlDIR genes and elucidate their functions in lignan biosynthesis, this study performed transcriptome-wide analysis and characterized the catalytic activity of the PlDIR1 protein. Results Fifteen full-length unique PlDIR genes were identified in P. leptostachya. A phylogenetic analysis of the PlDIRs classified them into four subfamilies (DIR-a, DIR-b/d, DIR-e, and DIR-g), and 12 conserved motifs were found among them. In tissue-specific expression analysis, except for PlDIR7, which displayed the highest transcript abundance in seeds, the other PlDIRs showed preferential expression in roots, leaves, and stems. Furthermore, the treatments with signaling molecules demonstrated that PlDIRs could be significantly induced by methyl jasmonate (MeJA), salicylic acid (SA), and ethylene (ETH), both in the roots and leaves of P. leptostachya. In examining the tertiary structure of the protein and the critical amino acids, it was found that PlDIR1, one of the DIR-a subfamily members, might be involved in the region- and stereo-selectivity of the phenoxy radical. Accordingly, LC–MS/MS analysis demonstrated the catalytic activity of recombinant PlDIR1 protein from Escherichia coli to direct coniferyl alcohol coupling into ( +)-pinoresinol. The active sites and hydrogen bonds of the interaction between PlDIR1 and bis-quinone methide (bisQM), the intermediate in ( +)-pinoresinol formation, were analyzed by molecular docking. As a result, 18 active sites and 4 hydrogen bonds (Asp-42, Ala-113, Leu-138, Arg-143) were discovered in the PlDIR1-bisQM complex. Moreover, correlation analysis indicated that the expression profile of PlDIR1 was closely connected with lignan accumulations after SA treatment. Conclusions The results of this study will provide useful clues for uncovering P. leptostachya's lignan biosynthesis pathway as well as facilitate further studies on the DIR family.

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