Maillard Reaction Products with Anti-Tobacco Mosaic Virus Activities Generated in Processed Thermopsis lanceolata R. Br. Seed Extract

Six novel Maillard reaction products (MRPs) (1–6) were isolated from the processed Thermopsis lanceolata R. Br. seed extract, along with one biogenetically related intermediate (7). Compounds 1–4 possessed three rare dimerization patterns constructed by cytisine, whereas compounds 5 and 6 represente...

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Published in:Journal of organic chemistry 2022-09, Vol.87 (17), p.11309-11318
Main Authors: Hu, Zhan-Xing, Zhang, Peng, Zou, Ji-Bin, An, Qiao, Yi, Ping, Yuan, Chun-Mao, Yang, Jue, Gu, Wei, Huang, Lie-Jun, Zhao, Li-Hua, Hao, Xiao-Jiang
Format: Article
Language:English
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Summary:Six novel Maillard reaction products (MRPs) (1–6) were isolated from the processed Thermopsis lanceolata R. Br. seed extract, along with one biogenetically related intermediate (7). Compounds 1–4 possessed three rare dimerization patterns constructed by cytisine, whereas compounds 5 and 6 represented the first example of the addition products of cytisine and 5,6-dihydroxy-4-hexanolide. Their structures were elucidated by comprehensive spectroscopic data analysis and quantum chemistry calculations including GIAO 13C­{1H} NMR and ECD calculation, combined with single-crystal X-ray diffraction analysis. Biologically, compound 3 displayed significant anti-tobacco mosaic virus activity compared with the positive control ningnanmycin.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00517