Stable Axially Chiral Isomers of Arylnaphthalene Lignan Glycosides with Antiviral Potential Discovered from Justicia procumbens

Yang Zhao, Chuen Fai KU, Xin Ya Xu, Nga Yi Tsang, Yu Zhu, Chen Liang Zhao, Kang Lun Liu, Chuang Chuang Li, Lijun Rong, Hongjie ZHANG*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Arylnaphthalene lignans (ANLs) were known to have axial chirality due to the biphenyl skeleton with hindered rotation at the single bond. However, the stable ANL atropisomers have not been isolated from nature until the present study. Phytochemical separation of the methanol extract of the stems and barks of Justicia procumbens led to the isolation of 11 ANL glycosides including four pairs of new atropisomers with stable confirmations at room temperature. Their structures were deduced from elucidation of the extensive spectral data, and their absolute configurations were determined by the circular dichroism, electronic circular dichroism, and X-ray methods as well as the total synthesis of one pair of the atropisomers. The ANL compounds were evaluated for their antiviral potential, and it was found that they displayed great antiviral activity discrepancy between a pair of atropisomers due to the geometric orientation. The 1′P-oriented atropisomers showed much more significant antiviral potency than their corresponding 1′M-oriented counterparts. The biological activity discrepancy caused by the axial chirality will not only inspire synthetic design of novel ANL atropisomers to enrich the structural diversity, but also provide important hints to direct the synthetic approaches toward the antiviral drug development of ANL compounds.

Original languageEnglish
Pages (from-to)5568-5583
Number of pages16
JournalJournal of Organic Chemistry
Volume86
Issue number8
DOIs
Publication statusAccepted/In press - 2021

Scopus Subject Areas

  • Organic Chemistry

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