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

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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.

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Characterization and expression analysis of genes encoding three small heat shock proteins in the oriental armyworm, Mythimna separata (Walker).

Project description:Small heat shock proteins (sHsps) function in the response of insects to abiotic stress; however, their role in response to biotic stress has been under-investigated. Mythimna separata, the oriental armyworm, is polyphenetic and exhibits gregarious and solitary phases in response to high and low population density, respectively. In this study, three genes were identified encoding sHsps, namely MsHsp19.7, MsHsp19.8 and MsHsp21.4, and expression levels in solitary and gregarious M. separata were compared. The deduced protein sequences of the three MsHsps had molecular weights of 19.7, 19.8 and 21.4 kDa, respectively, and contained a conserved ?-crystalline domain. Real-time PCR analyses revealed that the three sHsps were transcribed in all developmental stages and were dramatically up-regulated at the 6th larval stage in gregarious individuals. Expression of the three MsHsps was variable in different tissues of 6th instar larvae, but exhibited consistent up- and down-regulation in the hindgut and Malpighian tubules of gregarious individuals, respectively. In addition, MsHsp19.7 and MsHsp19.8 were significantly induced when solitary forms were subjected to crowding for 36 h, but all three MsHsps were down-regulated when gregarious forms were isolated. Our findings suggest that population density functions as a stress factor and impacts MsHsps expression in M. separata.

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