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
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cited_by cdi_FETCH-LOGICAL-a310t-cc152cfab04bf0fbd2fa0b555a42e01d93b6f0755e1009ca61c667fa4e34d05c3
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container_end_page 11318
container_issue 17
container_start_page 11309
container_title Journal of organic chemistry
container_volume 87
creator Hu, Zhan-Xing
Zhang, Peng
Zou, Ji-Bin
An, Qiao
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Yang, Jue
Gu, Wei
Huang, Lie-Jun
Zhao, Li-Hua
Hao, Xiao-Jiang
description 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.
doi_str_mv 10.1021/acs.joc.2c00517
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title Maillard Reaction Products with Anti-Tobacco Mosaic Virus Activities Generated in Processed Thermopsis lanceolata R. Br. Seed Extract
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