Axial Chirality and Antiviral Activity Evaluation of Arylnaphthalene Lignan Glycosides from Justicia procumbens

Yang Zhao; Nga Yi Tsang; Xin-Ya Xu; Chen-Liang Zhao; Chuen-Fai Ku; Wan-Fei Li; Yu Zhu; Kang-Lun Liu; Lijun Rong; Hong-Jie Zhang

doi:10.1002/ajoc.202200267

Axial Chirality and Antiviral Activity Evaluation of Arylnaphthalene Lignan Glycosides from Justicia procumbens

Yang Zhao, Nga Yi Tsang, Xin-Ya Xu, Chen-Liang Zhao, Chuen-Fai Ku, Wan-Fei Li, Yu Zhu, Kang-Lun Liu, Lijun Rong, Hong-Jie Zhang^*

^*Corresponding author for this work

Chinese Medicine - Teaching and Research Division

Research output: Contribution to journal › Journal article › peer-review

4 Citations (Scopus)

Abstract

One of the structural uniqueness of arylnaphthalene lignans (ANLs) is their potential atropoisomerism, which may result in bioactivity discrepancy. However, the stable ANL atropisomers rarely exist in nature. In the course of our phytochemical study of Justicia procumbens, we isolated nine ANL glycosides (1–9) with four of them (1–4) being identified as new stable atropisomers. Their absolute configurations were determined based on the analysis of the circular dichroism (CD) and electronic circular dichroism (ECD) data. The ANL compounds were evaluated for their antiviral potential as entry inhibitors against the infections of H5N1 influenza virus, vesicular stomatitis virus (VSV) and severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) with 5 being the most potent one with IC₅₀ values ranging from 0.0063–1.13 μM. The atropisomers did not display significant antiviral activity, indicating that a free rotation of the biphenyl aryl-aryl bond could play a significant role in the antiviral activity of ANL compounds.

Original language	English
Article number	e202200267
Journal	Asian Journal of Organic Chemistry
Volume	11
Issue number	8
Early online date	17 Jun 2022
DOIs	https://doi.org/10.1002/ajoc.202200267
Publication status	Published - Aug 2022

Scopus Subject Areas

Organic Chemistry

User-Defined Keywords

antiviral activities
arylnaphthalene lignans
atropisomers
Justicia procumbens
medicinal plant

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/ajoc.202200267

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title = "Axial Chirality and Antiviral Activity Evaluation of Arylnaphthalene Lignan Glycosides from Justicia procumbens",

abstract = "One of the structural uniqueness of arylnaphthalene lignans (ANLs) is their potential atropoisomerism, which may result in bioactivity discrepancy. However, the stable ANL atropisomers rarely exist in nature. In the course of our phytochemical study of Justicia procumbens, we isolated nine ANL glycosides (1–9) with four of them (1–4) being identified as new stable atropisomers. Their absolute configurations were determined based on the analysis of the circular dichroism (CD) and electronic circular dichroism (ECD) data. The ANL compounds were evaluated for their antiviral potential as entry inhibitors against the infections of H5N1 influenza virus, vesicular stomatitis virus (VSV) and severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) with 5 being the most potent one with IC50 values ranging from 0.0063–1.13 μM. The atropisomers did not display significant antiviral activity, indicating that a free rotation of the biphenyl aryl-aryl bond could play a significant role in the antiviral activity of ANL compounds.",

keywords = "antiviral activities, arylnaphthalene lignans, atropisomers, Justicia procumbens, medicinal plant",

author = "Yang Zhao and Tsang, {Nga Yi} and Xin-Ya Xu and Chen-Liang Zhao and Chuen-Fai Ku and Wan-Fei Li and Yu Zhu and Kang-Lun Liu and Lijun Rong and Hong-Jie Zhang",

note = "Funding Information: This research was funded by the Research Grants Council of the Hong Kong Special Administrative Region, China (grant numbers HKBU 12103618 and HKBU 12103021), the Innovation and Technology Commission of Hong Kong Special Administrative Region, China (MHP/105/19), the Health and Medical Research Fund (COVID190214) of the Food and Health, the Government of the Hong Kong Special Administrative Region, and the Hong Kong Scholars Program Foundation (NO.XJ2017058). We are grateful to Dr. Liu Kai from Institute of Marine Drugs, Guangxi University of Chinese Medicine, for assistance with the ECD calculations and Professor Pei‐Yuan Yu, Department of Chemistry, Southern University of Science and Technology, for assistance with the calculation of the barriers between the two atropisomers. Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

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AU - Zhao, Yang

AU - Tsang, Nga Yi

AU - Xu, Xin-Ya

AU - Zhao, Chen-Liang

AU - Ku, Chuen-Fai

AU - Li, Wan-Fei

AU - Zhu, Yu

AU - Liu, Kang-Lun

AU - Rong, Lijun

AU - Zhang, Hong-Jie

N1 - Funding Information: This research was funded by the Research Grants Council of the Hong Kong Special Administrative Region, China (grant numbers HKBU 12103618 and HKBU 12103021), the Innovation and Technology Commission of Hong Kong Special Administrative Region, China (MHP/105/19), the Health and Medical Research Fund (COVID190214) of the Food and Health, the Government of the Hong Kong Special Administrative Region, and the Hong Kong Scholars Program Foundation (NO.XJ2017058). We are grateful to Dr. Liu Kai from Institute of Marine Drugs, Guangxi University of Chinese Medicine, for assistance with the ECD calculations and Professor Pei‐Yuan Yu, Department of Chemistry, Southern University of Science and Technology, for assistance with the calculation of the barriers between the two atropisomers. Publisher Copyright: © 2022 Wiley-VCH GmbH.

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N2 - One of the structural uniqueness of arylnaphthalene lignans (ANLs) is their potential atropoisomerism, which may result in bioactivity discrepancy. However, the stable ANL atropisomers rarely exist in nature. In the course of our phytochemical study of Justicia procumbens, we isolated nine ANL glycosides (1–9) with four of them (1–4) being identified as new stable atropisomers. Their absolute configurations were determined based on the analysis of the circular dichroism (CD) and electronic circular dichroism (ECD) data. The ANL compounds were evaluated for their antiviral potential as entry inhibitors against the infections of H5N1 influenza virus, vesicular stomatitis virus (VSV) and severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) with 5 being the most potent one with IC50 values ranging from 0.0063–1.13 μM. The atropisomers did not display significant antiviral activity, indicating that a free rotation of the biphenyl aryl-aryl bond could play a significant role in the antiviral activity of ANL compounds.

AB - One of the structural uniqueness of arylnaphthalene lignans (ANLs) is their potential atropoisomerism, which may result in bioactivity discrepancy. However, the stable ANL atropisomers rarely exist in nature. In the course of our phytochemical study of Justicia procumbens, we isolated nine ANL glycosides (1–9) with four of them (1–4) being identified as new stable atropisomers. Their absolute configurations were determined based on the analysis of the circular dichroism (CD) and electronic circular dichroism (ECD) data. The ANL compounds were evaluated for their antiviral potential as entry inhibitors against the infections of H5N1 influenza virus, vesicular stomatitis virus (VSV) and severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) with 5 being the most potent one with IC50 values ranging from 0.0063–1.13 μM. The atropisomers did not display significant antiviral activity, indicating that a free rotation of the biphenyl aryl-aryl bond could play a significant role in the antiviral activity of ANL compounds.

KW - antiviral activities

KW - arylnaphthalene lignans

KW - atropisomers

KW - Justicia procumbens

KW - medicinal plant

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U2 - 10.1002/ajoc.202200267

DO - 10.1002/ajoc.202200267

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AN - SCOPUS:85133503427

SN - 2193-5807

VL - 11

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 8

M1 - e202200267

ER -

Axial Chirality and Antiviral Activity Evaluation of Arylnaphthalene Lignan Glycosides from Justicia procumbens

Abstract

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