Stable Axially Chiral Isomers of Arylnaphthalene Lignan Glycosides with Antiviral Potential Discovered from Justicia procumbens
| Autor: | Hongjie Zhang, Nga Yi Tsang, Lijun Rong, Yang Zhao, Chen Liang Zhao, Chuen Fai Ku, Xin Ya Xu, Chuang-Chuang Li, Yu Zhu, Kang Lun Liu |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Lignan
chemistry.chemical_classification Circular dichroism Atropisomer biology 010405 organic chemistry Stereochemistry Organic Chemistry Glycoside Total synthesis 010402 general chemistry biology.organism_classification 01 natural sciences Justicia procumbens 0104 chemical sciences chemistry.chemical_compound chemistry Axial chirality Molecule |
| Zdroj: | The Journal of Organic Chemistry. 86:5568-5583 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.1c00068 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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