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KMID : 0043320220450090631
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Archives of Pharmacal Research
2022 Volume.45 No. 9 p.631 ~ p.643
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Structures, biomimetic synthesis, and anti-SARS-CoV-2 activity of two pairs of enantiomeric phenylpropanoid-conjugated protoberberine alkaloids from the rhizomes of Corydalis decumbens
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Lu Jing-Guang
Wang Yingwei
Yang Ming-Rong
Wang Cai-Yun
Meng Jieru
Liu Jiazheng
Yang Zifeng
Wu Kongsong
Bai Li-Ping
Zhu Guo-Yuan
Jiang Zhi-Hong
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Abstract
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(±)-Decumicorine A (1) and (±)-epi-decumicorine A (2), two pairs of enantiomeric isoquinoline alkaloids featuring a novel phenylpropanoid-conjugated protoberberine skeleton, were isolated and purified from the rhizomes of Corydalis decumbens. The separation of (±)-1 and (±)-2 was achieved by chiral HPLC to produce four optically pure enantiomers. The structures and absolute configurations of compounds (?)-1, (+)-1, (?)-2, and (+)-2 were elucidated by spectroscopic analysis, ECD calculations, and X-ray crystallographic analyses. The two racemates were generated from a Diels-Alder [4?+?2] cycloaddition between jatrorrhizine and ferulic acid in the proposed biosynthetic pathways, which were fully verified by a biomimetic synthesis. Moreover, compound (+)-1 exhibited an antiviral entry effect on SARS-CoV-2 pseudovirus by blocking spike binding to the ACE2 receptor on HEK-293T-ACE2h host cells.
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KEYWORD
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Corydalis decumbens, Isoquinoline alkaloid, Biomimetic synthesis, COVID-19, Anti-SARS-CoV-2
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