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High Value-Added Use of Citrus Industrial Wastes in Agriculture: Semisynthesis and Anti-Tobacco Mosaic Virus/Insecticidal Activities of Ester Derivatives of Limonin Modified in the B Ring.
Huang, Xiaobo; Li, Tianze; Shan, Xijie; Lu, Rongfei; Hao, Meng; Lv, Min; Sun, Zhiqiang; Xu, Hui.
Afiliación
  • Huang X; College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
  • Li T; College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
  • Shan X; College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
  • Lu R; College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
  • Hao M; College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
  • Lv M; College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
  • Sun Z; College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
  • Xu H; College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
J Agric Food Chem ; 68(44): 12241-12251, 2020 Nov 04.
Article en En | MEDLINE | ID: mdl-33103899
Globally, the citrus industry produces various wastes, which contain a great deal of limonoids. In order for the sustainable development of the citrus industry, and considering the diverse bioactivities of limonoids, a series of ester derivatives were constructed by structural modification of limonin in the B ring. Furthermore, two seven-membered lactone derivatives of limonin and obacunone with a novel skeleton in the B ring were obtained by the Baeyer-Villiger oxidation rearrangement. The steric structures of six key compounds 3a, 3b, 4m, 4n, 6, and 7 were determined by X-ray crystallography. It demonstrated that the molar ratio of 3a (7α-isomer) and 3b (7ß-isomer) depended on the mixed solvents in the reduction system. The anti-tobacco mosaic virus (TMV) activities under three different modes of action for most of the tested compounds were as the following sequence: inactivation effect > protection effect > curative effect. It was noteworthy that compound 4aa displayed the most potent anti-TMV/insect growth inhibitory activities, which indicated that the introduction of the phenylacryloyloxy group at the C-7ß position of limonin could significantly improve its agricultural biological activities. This study will pave the way for future value-added application of citrus industrial wastes and provide strong evidence for the discovery of sustainable biopesticides based on limonoids.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Antivirales / Virus del Mosaico del Tabaco / Citrus / Insecticidas Límite: Animals Idioma: En Revista: J Agric Food Chem Año: 2020 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Antivirales / Virus del Mosaico del Tabaco / Citrus / Insecticidas Límite: Animals Idioma: En Revista: J Agric Food Chem Año: 2020 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos