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Furan-Site Bromination and Transformations of Fraxinellone as Insecticidal Agents Against Mythimna separata Walker.

ABSTRACT: Furan ring of limoninoids is critical in exhibiting insecticidal activity. Herein, fraxinellone (1) was used as a template of furan-containing natural products and a series of its derivatives was synthesized by selective bromination in good yields on gram-scale and following Suzuki-Miyaura or Sonogashira coupling reactions in moderate to good yields. Bromination of limonin (9) was also accomplished without altering other functional groups in high yield. Furthermore, an evaluation of insecticidal activity against the instar larvae of Mythimna separata showed that derivatives 2, 3b, 3g, 5a, 5d and 5h displayed more potent insecticidal activity than 1 and toosendanin.

SUBMITTER: Dong QM

PROVIDER: S-EPMC5976728 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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Furan-Site Bromination and Transformations of Fraxinellone as Insecticidal Agents Against Mythimna separata Walker.

Dong Qing-Miao QM Dong Shuai S Shen Cheng C Cao Qing-Hao QH Song Ming-Yu MY He Qiu-Rui QR Wang Xiao-Ling XL Yang Xiao-Jun XJ Tang Jiang-Jiang JJ Gao Jin-Ming JM

Scientific reports 20180530 1

Furan ring of limoninoids is critical in exhibiting insecticidal activity. Herein, fraxinellone (1) was used as a template of furan-containing natural products and a series of its derivatives was synthesized by selective bromination in good yields on gram-scale and following Suzuki-Miyaura or Sonogashira coupling reactions in moderate to good yields. Bromination of limonin (9) was also accomplished without altering other functional groups in high yield. Furthermore, an evaluation of insecticidal ...[more]

PMID: 29849138

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Semi-Synthesis of C-Ring Cyclopropyl Analogues of Fraxinellone and Their Insecticidal Activity Against Mythimna separata Walker.

Project description:Fraxinellone (1) is a naturally occurring degraded limonoid isolated from Meliaceae and Rutaceae plants. As a potential natural-product-based insecticidal agent, fraxinellone has been structurally modified to improve its activity. Furan ring of fraxinellone is critical in exhibiting its insecticidal activity, but with few modifications. Herein, C-ring-modified cyclopropyl analogues were semi-synthesized by Rh(II)-catalyzed cyclopropanation. The structures of the target compounds were well characterized by NMR and HRMS. The precise three-dimensional structural information of 3a was established by X-ray crystallography. Their insecticidal activity was evaluated against Mythimna separata Walker by a leaf-dipping method. Compound 3c exhibited stronger insecticidal activity than 1 and toosendanin against M. separata with teratogenic symptoms during the different periods, implying that cyclopropanation of the furan ring could strengthen the insecticidal activity of fraxinellone.

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Furan-site transformations of obacunone as potent insecticidal agents.

Project description:Furan ring is a key pharmacophore for insecticidal activity of limoninoids. To develop natural-product-based insecticidal agents, a series of furan-site transformations (2, 3 and 3a–j) of obacunone were synthesized by selective bromination and following coupling reactions without altering other functional groups. Bioassays indicated that derivatives 3e, 3f and 3j displayed more potent insecticidal activity than obacunone and toosendanin against the instar larvae of Mythimna separate Walker. Besides, their structure–activity relationships were discussed.

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Functional Analysis of MsepOR13 in the Oriental Armyworm Mythimna separata (Walker).

Project description:Olfaction in insects has a critical role in recognizing the host, finding food, and choosing mating partners, as well as avoiding predators. Odorant receptors (ORs), which are housed in the dendritic membrane of sensory neurons and extended into the lymph of sensilla on insect antennae, are participating in the detection of volatile compounds in insects. In the present study, we identified an OR gene, named MsepOR13, in the oriental armyworm Mythimna separata (Walker). Quantitative real-time polymerase chain reaction revealed that MsepOR13 was expressed mainly in the antennae of male and female moths. In in vitro heterologous expression experiments, MsepOR13 was widely tuned to 32 of the 67 different compounds tested. Furthermore, MsepOR13 responded to eugenol at a low concentration of 10-9 M, with an EC50 value of 3.91 × 10-6 M. The high sensitivity suggests an important role for the OR13 gene in the moth olfactory system.

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The insecticidal effect of the botanical insecticide chlorogenic acid on Mythimna separata (Walker) is related to changes in MsCYP450 gene expression.

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The Rapid Evolution of Resistance to Vip3Aa Insecticidal Protein in Mythimna separata (Walker) Is Not Related to Altered Binding to Midgut Receptors.

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Transcriptome analysis of molecular mechanisms responsible for light-stress response in Mythimna separata (Walker).

Project description:Light is an important environmental signal for most insects. The Oriental Armyworm, Mythimna separata, is a serious pest of cereal crops worldwide, and is highly sensitive to light signals during its developmental and reproductive stages. However, molecular biological studies of its response to light stress are scarce, and related genomic information is not available. In this study, we sequenced and de novo assembled the transcriptomes of M. separata exposed to four different light conditions: dark, white light (WL), UV light (UVL) and yellow light (YL). A total of 46,327 unigenes with an average size of 571 base pairs (bp) were obtained, among which 24,344 (52.55%) matched to public databases. The numbers of genes differentially expressed between dark vs WL, dark vs UVL, dark vs YL, and UVL vs YL were 12,012, 12,950, 14,855, and 13,504, respectively. These results suggest that light exposure altered gene expression patterns in M. separata. Putative genes involved in phototransduction-fly, phototransduction, circadian rhythm-fly, olfactory transduction, and taste transduction were identified. This study thus identified a series of candidate genes and pathways potentially related to light stress in M. separata.

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Identification of 35 C-Type Lectins in the Oriental Armyworm, Mythimna separata (Walker).

Project description:Insect C-type lectins (CTLs) play vital roles in modulating humoral and cellular immune responses. The oriental armyworm, Mythimna separata (Walker) (Lepidoptera: Noctuidae) is a migratory pest that causes significant economic loss in agriculture. CTLs have not yet been systematically identified in M. separata. In this study, we first constructed a transcriptome of M. separata larvae, generating a total of 45,888 unigenes with an average length of 910 bp. Unigenes were functionally annotated in six databases: NR, GO, KEGG, Pfam, eggNOG, and Swiss-Prot. Unigenes were enriched in functional pathways, such as those of signal transduction, endocrine system, cellular community, and immune system. Thirty-five unigenes encoding C-type lectins were identified, including CTL-S1~CTL-S6 (single CRD) and IML-1~IML-29 (dual CRD). Phylogenetic analyses showed dramatic lineage-specific expansions of IMLs. Sequence alignment and structural modeling identified potential ligand-interacting residues. Real-time qPCR revealed that CTL-Ss mainly express in eggs and early stage larvae, while IMLs mainly express in mid-late-stage larvae, pupae, and adults. In naïve larvae, hemocytes, fat body, and epidermis are the major tissues that express CTLs. In larvae challenged by Escherichia coli, Staphylococcus aureus, or Beauveria bassiana, the expression of different CTLs was stimulated in hemocytes, fat body and midgut. The present study will help further explore functions of M. separata CTLs.

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Functional Characterization of Sex Pheromone Neurons and Receptors in the Armyworm, Mythimna separata (Walker).

Project description:Pheromone receptors (PRs) of moths are expressed on the dendritic membrane of odorant receptor neurons (ORNs) housed in the long trichoid sensilla (TS) of antennae and are essential to sex pheromone reception. The function of peripheral neurons of Mythimna separata in recognizing sex pheromones is still unclear. In this study, electroantennogram recordings were performed from male and female antennae of M. separata, and showed that the major component of sex pheromones, (Z)-11-hexadecenal (Z11-16:Ald), evoked the strongest response of male antennae with significant differences between sexes. Single sensillum recording was used to record responses of neurons housed in TS of male M. separata. The results revealed four types of TS with three neurons housed in each type, based on profiles of responses to sex pheromone components and pheromone analogs. ORN-B of type-I TS was specifically tuned to the major sex pheromone component Z11-16:Ald; ORN-Bs in type-III and type-IV TSs were, respectively, activated by minor components (Z)-11-hexadecen-1-yl acetate (Z11-16:OAc) and hexadecenal (16:Ald); and ORNs in type-II TS were mainly activated by the sex pheromone analogs. We further cloned full-length sequences of six putative PR genes and an Orco gene. Functional characterization of PRs in the Xenopus oocyte system demonstrated that male antennae-biased MsepPR1 responded strongly to (Z)-9-tetradecenal (Z9-14:Ald), suggesting that MsepPR1 may be expressed in type-II TS. MsepPR6 was exclusively tuned to (Z)-9-tetradecen-1-yl acetate (Z9-14:OAc). MsepPR2 and MsepPR4 showed no responses to any tested components. Female antennae-biased MespPR5 was broadly tuned to Z9-14:Ald, Z9-14:OAc, Z11-16:Ald, and (Z)-11-hexadecen-1-ol (Z11-16:OH). Our results further enriched the sex pheromone recognition mechanism in the peripheral nervous system of moth M. separata.

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Cloning, expression and purification of subunit H of vacuolar H⁺-ATPase from Mythimna separata Walker (Lepidoptera: Noctuidae).

Project description:The vacuolar (H+)-ATPase (V-ATPase) of insect, which is composed of membrane-bound V0 complex and peripheral V1 complex, participates in lots of important physiological process. Subunit H, as a subunit of V1 complex, plays a vital role in bridging the communication between V1 and V0 complexes and interaction with other proteins. Yeast subunit H has been successfully crystallized through expression in E. coli, but little is known about the structure of insect subunit H. In this study, we cloned, expressed and purified the subunit H from midgut of Mythimna separata Walker. Through RACE (rapidly amplification of cDNA ends) technique, we got 1807 bp full length of subunit H, and to keep the nature structure of subunit H, we constructed Baculovirus expression vector with His-tag in the C-terminal and expressed the recombinant protein in insect sf9 cells, thereafter, purified the recombinant protein by Ni-NTA columns. Results of SDS-PAGE, western blotting and mass spectrometry showed that the recombinant protein was successfully expressed. The method of expressing and purifying M. separata subunit H will provide a foundation for obtaining the crystal of subunit H and further study of the design of novel insecticides based on its structure and function.

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New Insecticidal Agents from Halogenation/Acylation of the Furyl-Ring of Fraxinellone.

Project description:Introduction of the halogen atom or the acyl group at the C-ring of fraxinellone was investigated. Some unexpected halogenation products were obtained with the different chlorination/bromination reagents, and their possible reaction mechanisms were also proposed. Seven key steric structures of 2a', 2b, 2b', 2c', 3a, 3b, and one isomer (5'?-Cl) of 2a were further confirmed by single-crystal X-ray diffraction. Especially compounds 2a, 2a', 3a and 3c exhibited more potent insecticidal activity than toosendanin. Some structure-activity relationships of tested compounds were also described.

| S-EPMC5075773 | biostudies-literature

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