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.

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 (7β-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-7β 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.

Citation

Xiaobo Huang, Tianze Li, Xijie Shan, Rongfei Lu, Meng Hao, Min Lv, Zhiqiang Sun, Hui Xu. 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. Journal of agricultural and food chemistry. 2020 Nov 04;68(44):12241-12251

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PMID: 33103899

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