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Phytotoxic Compounds Isolated from Leaves of the Invasive Weed Xanthium spinosum

The aim of this study was to identify bioactive compounds from leaves of the invasive plant Xanthium spinosum and assess their phytotoxic activity. Activity-guided fractionation led to the isolation of 6 bioactive compounds: xanthatin (1), 1α,5α-epoxyxanthatin (2), 4-epiisoxanthanol (3), 4-epixantha...

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Autores principales: Yuan, Zhuogeng, Zheng, Xiangwei, Zhao, Yu, Liu, Ying, Zhou, Shixing, Wei, Caixia, Hu, Yunxia, Shao, Hua
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6278460/
https://www.ncbi.nlm.nih.gov/pubmed/30388777
http://dx.doi.org/10.3390/molecules23112840
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author Yuan, Zhuogeng
Zheng, Xiangwei
Zhao, Yu
Liu, Ying
Zhou, Shixing
Wei, Caixia
Hu, Yunxia
Shao, Hua
author_facet Yuan, Zhuogeng
Zheng, Xiangwei
Zhao, Yu
Liu, Ying
Zhou, Shixing
Wei, Caixia
Hu, Yunxia
Shao, Hua
author_sort Yuan, Zhuogeng
collection PubMed
description The aim of this study was to identify bioactive compounds from leaves of the invasive plant Xanthium spinosum and assess their phytotoxic activity. Activity-guided fractionation led to the isolation of 6 bioactive compounds: xanthatin (1), 1α,5α-epoxyxanthatin (2), 4-epiisoxanthanol (3), 4-epixanthanol (4), loliolide (5) and dehydrovomifoliol (6). Of them, compounds 2–6 were isolated from the X. spinosum for the first time. The structures of 1–6 were elucidated on the basis of extensive NMR studies and ESI-MS measurements as well as comparison with literature data. All of compounds were evaluated for their phytotoxic activity. Among them, compounds 1–4 exhibited stronger activity on 2 receiver plants compared with the other 2 compounds, with xanthatin (1) being the most potent compound, which suppressed root growth of the dicot plant Amaranthus retroflexus by 32.5%, 39.4%, 84.7% when treated xanthatin (1) at 5, 20, and 100 µg/mL, while for the monocot plant, root growth was inhibited by 14.7%, 28.0%, and 40.0%, respectively. Seedling growth was nearly completely inhibited when the concentration of xanthanolides increased to 500 µg/mL, whereas there was still some seedling growth when loliolide (5) and dehydrovomifoliol (6) were applied at the same concentration. Dehydrovomifoliol (6) did not negatively affect seedling growth of P. annua at all tested concentrations, and root length was still 42.0% of the control when the highest concentration 500 µg/mL was used. This is the first report of the phytotoxicity of 1α,5α-epoxyxanthatin (2), 4-epiisxanthanol (3) and 4-epixanthanol (4). These compounds have the potential to be utilized as natural herbicides, especially 4-epiisoxanthanol (3), which exhibited significant selective activity between the dicot and monocot plants. On the other hand, whether these bioactive substances serve as allelochemicals to facilitate the invasion success of X. spinosum needs to be further studied.
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spelling pubmed-62784602018-12-13 Phytotoxic Compounds Isolated from Leaves of the Invasive Weed Xanthium spinosum Yuan, Zhuogeng Zheng, Xiangwei Zhao, Yu Liu, Ying Zhou, Shixing Wei, Caixia Hu, Yunxia Shao, Hua Molecules Article The aim of this study was to identify bioactive compounds from leaves of the invasive plant Xanthium spinosum and assess their phytotoxic activity. Activity-guided fractionation led to the isolation of 6 bioactive compounds: xanthatin (1), 1α,5α-epoxyxanthatin (2), 4-epiisoxanthanol (3), 4-epixanthanol (4), loliolide (5) and dehydrovomifoliol (6). Of them, compounds 2–6 were isolated from the X. spinosum for the first time. The structures of 1–6 were elucidated on the basis of extensive NMR studies and ESI-MS measurements as well as comparison with literature data. All of compounds were evaluated for their phytotoxic activity. Among them, compounds 1–4 exhibited stronger activity on 2 receiver plants compared with the other 2 compounds, with xanthatin (1) being the most potent compound, which suppressed root growth of the dicot plant Amaranthus retroflexus by 32.5%, 39.4%, 84.7% when treated xanthatin (1) at 5, 20, and 100 µg/mL, while for the monocot plant, root growth was inhibited by 14.7%, 28.0%, and 40.0%, respectively. Seedling growth was nearly completely inhibited when the concentration of xanthanolides increased to 500 µg/mL, whereas there was still some seedling growth when loliolide (5) and dehydrovomifoliol (6) were applied at the same concentration. Dehydrovomifoliol (6) did not negatively affect seedling growth of P. annua at all tested concentrations, and root length was still 42.0% of the control when the highest concentration 500 µg/mL was used. This is the first report of the phytotoxicity of 1α,5α-epoxyxanthatin (2), 4-epiisxanthanol (3) and 4-epixanthanol (4). These compounds have the potential to be utilized as natural herbicides, especially 4-epiisoxanthanol (3), which exhibited significant selective activity between the dicot and monocot plants. On the other hand, whether these bioactive substances serve as allelochemicals to facilitate the invasion success of X. spinosum needs to be further studied. MDPI 2018-11-01 /pmc/articles/PMC6278460/ /pubmed/30388777 http://dx.doi.org/10.3390/molecules23112840 Text en © 2018 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Yuan, Zhuogeng
Zheng, Xiangwei
Zhao, Yu
Liu, Ying
Zhou, Shixing
Wei, Caixia
Hu, Yunxia
Shao, Hua
Phytotoxic Compounds Isolated from Leaves of the Invasive Weed Xanthium spinosum
title Phytotoxic Compounds Isolated from Leaves of the Invasive Weed Xanthium spinosum
title_full Phytotoxic Compounds Isolated from Leaves of the Invasive Weed Xanthium spinosum
title_fullStr Phytotoxic Compounds Isolated from Leaves of the Invasive Weed Xanthium spinosum
title_full_unstemmed Phytotoxic Compounds Isolated from Leaves of the Invasive Weed Xanthium spinosum
title_short Phytotoxic Compounds Isolated from Leaves of the Invasive Weed Xanthium spinosum
title_sort phytotoxic compounds isolated from leaves of the invasive weed xanthium spinosum
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6278460/
https://www.ncbi.nlm.nih.gov/pubmed/30388777
http://dx.doi.org/10.3390/molecules23112840
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