Unknown

Dataset Information

0

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

ABSTRACT: 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.

SUBMITTER: Yang XJ 

PROVIDER: S-EPMC7179169 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

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

Yang Xiao-Jun XJ   Dong Qing-Miao QM   Wang Min-Ran MR   Tang Jiang-Jiang JJ  

Molecules (Basel, Switzerland) 20200302 5

Fraxinellone (<b>1</b>) 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  ...[more]

Similar Datasets

Unknown Furan-Site Bromination and Transformations of Fraxinellone as Insecticidal Agents Against Mythimna separata Walker.
| S-EPMC5976728 | biostudies-literature
Unknown Functional Analysis of MsepOR13 in the Oriental Armyworm <i>Mythimna separata</i> (Walker).
| S-EPMC6465334 | biostudies-literature
Unknown The Rapid Evolution of Resistance to Vip3Aa Insecticidal Protein in <i>Mythimna separata</i> (Walker) Is Not Related to Altered Binding to Midgut Receptors.
| S-EPMC8190635 | biostudies-literature
Unknown Transcriptome analysis of molecular mechanisms responsible for light-stress response in Mythimna separata (Walker).
| S-EPMC5367045 | biostudies-literature
Unknown Identification of 35 C-Type Lectins in the Oriental Armyworm, <i>Mythimna separata</i> (Walker).
| S-EPMC8235521 | biostudies-literature
Unknown New Insecticidal Agents from Halogenation/Acylation of the Furyl-Ring of Fraxinellone.
| S-EPMC5075773 | biostudies-literature
Unknown Functional Characterization of Sex Pheromone Neurons and Receptors in the Armyworm, <i>Mythimna separata</i> (Walker).
| S-EPMC8113758 | biostudies-literature
Unknown A Semi-Synthetic Diet and the Potential Important Chemicals for Mythimna separata (Lepidoptera: Noctuidae).
| S-EPMC6855139 | biostudies-literature
Unknown Cloning, expression and purification of subunit H of vacuolar H⁺-ATPase from Mythimna separata Walker (Lepidoptera: Noctuidae).
| S-EPMC4200773 | biostudies-literature
Unknown Characterization and expression analysis of genes encoding three small heat shock proteins in the oriental armyworm, Mythimna separata (Walker).
| S-EPMC7417081 | biostudies-literature