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Indole Alkaloids and Chromones from the Stem Bark of Cassia alata and Their Antiviral Activities

The Cassia (Leguminosae) genus has attracted a lot of attention as a prolific source of alkaloids and chromones with diverse structures and biological properties. The aim of this study is to screen the antiviral compounds from Cassia alata. The extract of the stem bark of this plant was separated us...

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Autores principales: Yang, Pei-Song, Dai, Jia-Meng, Gu, Xue-Jiao, Xiong, Wen, Huang, De-Quan, Qiu, Shi-Yu, Zheng, Jun-Na, Li, Yong, Yang, Feng-Xian, Zhou, Min
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9144915/
https://www.ncbi.nlm.nih.gov/pubmed/35630603
http://dx.doi.org/10.3390/molecules27103129
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author Yang, Pei-Song
Dai, Jia-Meng
Gu, Xue-Jiao
Xiong, Wen
Huang, De-Quan
Qiu, Shi-Yu
Zheng, Jun-Na
Li, Yong
Yang, Feng-Xian
Zhou, Min
author_facet Yang, Pei-Song
Dai, Jia-Meng
Gu, Xue-Jiao
Xiong, Wen
Huang, De-Quan
Qiu, Shi-Yu
Zheng, Jun-Na
Li, Yong
Yang, Feng-Xian
Zhou, Min
author_sort Yang, Pei-Song
collection PubMed
description The Cassia (Leguminosae) genus has attracted a lot of attention as a prolific source of alkaloids and chromones with diverse structures and biological properties. The aim of this study is to screen the antiviral compounds from Cassia alata. The extract of the stem bark of this plant was separated using silica gel, MCI, ODS C18, and Sephadex LH-20 column chromatography, as well as semi-preparative HPLC. As a result, three new indole alkaloids, alataindoleins A–C (1–3); one new chromone, alatachromone A (4); and a new dimeric chromone-indole alkaloid, alataindolein D (5) were isolated. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. Interestingly, alataindolein D (5) represents a new type of dimeric alkaloid with an unusual N-2−C-16’ linkage, which is biogenetically derived from a chromone and an indole alkaloid via an intermolecular nucleophilic substitution reaction. Compounds 1–5 were tested for their anti-tobacco mosaic virus (TMV) and anti-rotavirus activities, and the results showed that compounds 2–4 showed high anti-TMV activities with inhibition rates of 44.4%, 66.5%, and 52.3%, respectively. These rates were higher than those of the positive control (with inhibition rate of 32.8%). Compounds 1 and 5 also showed potential anti-TMV activities with inhibition rates of 26.5% and 31.8%, respectively. In addition, compounds 1–5 exhibited potential anti-rotavirus activities with therapeutic index (TI) values in the range of 9.75~15.3. The successful isolation and structure identification of the above new compounds provided materials for the screening of antivirus drugs, and contributed to the development and utilization of C. alata.
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spelling pubmed-91449152022-05-29 Indole Alkaloids and Chromones from the Stem Bark of Cassia alata and Their Antiviral Activities Yang, Pei-Song Dai, Jia-Meng Gu, Xue-Jiao Xiong, Wen Huang, De-Quan Qiu, Shi-Yu Zheng, Jun-Na Li, Yong Yang, Feng-Xian Zhou, Min Molecules Article The Cassia (Leguminosae) genus has attracted a lot of attention as a prolific source of alkaloids and chromones with diverse structures and biological properties. The aim of this study is to screen the antiviral compounds from Cassia alata. The extract of the stem bark of this plant was separated using silica gel, MCI, ODS C18, and Sephadex LH-20 column chromatography, as well as semi-preparative HPLC. As a result, three new indole alkaloids, alataindoleins A–C (1–3); one new chromone, alatachromone A (4); and a new dimeric chromone-indole alkaloid, alataindolein D (5) were isolated. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. Interestingly, alataindolein D (5) represents a new type of dimeric alkaloid with an unusual N-2−C-16’ linkage, which is biogenetically derived from a chromone and an indole alkaloid via an intermolecular nucleophilic substitution reaction. Compounds 1–5 were tested for their anti-tobacco mosaic virus (TMV) and anti-rotavirus activities, and the results showed that compounds 2–4 showed high anti-TMV activities with inhibition rates of 44.4%, 66.5%, and 52.3%, respectively. These rates were higher than those of the positive control (with inhibition rate of 32.8%). Compounds 1 and 5 also showed potential anti-TMV activities with inhibition rates of 26.5% and 31.8%, respectively. In addition, compounds 1–5 exhibited potential anti-rotavirus activities with therapeutic index (TI) values in the range of 9.75~15.3. The successful isolation and structure identification of the above new compounds provided materials for the screening of antivirus drugs, and contributed to the development and utilization of C. alata. MDPI 2022-05-13 /pmc/articles/PMC9144915/ /pubmed/35630603 http://dx.doi.org/10.3390/molecules27103129 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Yang, Pei-Song
Dai, Jia-Meng
Gu, Xue-Jiao
Xiong, Wen
Huang, De-Quan
Qiu, Shi-Yu
Zheng, Jun-Na
Li, Yong
Yang, Feng-Xian
Zhou, Min
Indole Alkaloids and Chromones from the Stem Bark of Cassia alata and Their Antiviral Activities
title Indole Alkaloids and Chromones from the Stem Bark of Cassia alata and Their Antiviral Activities
title_full Indole Alkaloids and Chromones from the Stem Bark of Cassia alata and Their Antiviral Activities
title_fullStr Indole Alkaloids and Chromones from the Stem Bark of Cassia alata and Their Antiviral Activities
title_full_unstemmed Indole Alkaloids and Chromones from the Stem Bark of Cassia alata and Their Antiviral Activities
title_short Indole Alkaloids and Chromones from the Stem Bark of Cassia alata and Their Antiviral Activities
title_sort indole alkaloids and chromones from the stem bark of cassia alata and their antiviral activities
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9144915/
https://www.ncbi.nlm.nih.gov/pubmed/35630603
http://dx.doi.org/10.3390/molecules27103129
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