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Diversity‐Oriented Synthesis of Natural‐Product‐like Libraries Containing a 3‐Methylbenzofuran Moiety for the Discovery of New Chemical Elicitors
Natural products are a major source of biological molecules. The 3‐methylfuran scaffold is found in a variety of plant secondary metabolite chemical elicitors that confer host‐plant resistance against insect pests. Herein, the diversity‐oriented synthesis of a natural‐product‐like library is reporte...
Autores principales: | , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5288756/ https://www.ncbi.nlm.nih.gov/pubmed/28168155 http://dx.doi.org/10.1002/open.201600118 |
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author | He, Xingrui Chen, Xia Lin, Songbo Mo, Xiaochang Zhou, Pengyong Zhang, Zhihao Lu, Yaoyao Yang, Yu Gu, Haining Shang, Zhicai Lou, Yonggen Wu, Jun |
author_facet | He, Xingrui Chen, Xia Lin, Songbo Mo, Xiaochang Zhou, Pengyong Zhang, Zhihao Lu, Yaoyao Yang, Yu Gu, Haining Shang, Zhicai Lou, Yonggen Wu, Jun |
author_sort | He, Xingrui |
collection | PubMed |
description | Natural products are a major source of biological molecules. The 3‐methylfuran scaffold is found in a variety of plant secondary metabolite chemical elicitors that confer host‐plant resistance against insect pests. Herein, the diversity‐oriented synthesis of a natural‐product‐like library is reported, in which the 3‐methylfuran core is fused in an angular attachment to six common natural product scaffolds—coumarin, chalcone, flavone, flavonol, isoflavone and isoquinolinone. The structural diversity of this library is assessed computationally using cheminformatic analysis. Phenotypic high‐throughput screening of β‐glucuronidase activity uncovers several hits. Further in vivo screening confirms that these hits can induce resistance in rice to nymphs of the brown planthopper Nilaparvata lugens. This work validates the combination of diversity‐oriented synthesis and high‐throughput screening of β‐glucuronidase activity as a strategy for discovering new chemical elicitors. |
format | Online Article Text |
id | pubmed-5288756 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-52887562017-02-06 Diversity‐Oriented Synthesis of Natural‐Product‐like Libraries Containing a 3‐Methylbenzofuran Moiety for the Discovery of New Chemical Elicitors He, Xingrui Chen, Xia Lin, Songbo Mo, Xiaochang Zhou, Pengyong Zhang, Zhihao Lu, Yaoyao Yang, Yu Gu, Haining Shang, Zhicai Lou, Yonggen Wu, Jun ChemistryOpen Full Papers Natural products are a major source of biological molecules. The 3‐methylfuran scaffold is found in a variety of plant secondary metabolite chemical elicitors that confer host‐plant resistance against insect pests. Herein, the diversity‐oriented synthesis of a natural‐product‐like library is reported, in which the 3‐methylfuran core is fused in an angular attachment to six common natural product scaffolds—coumarin, chalcone, flavone, flavonol, isoflavone and isoquinolinone. The structural diversity of this library is assessed computationally using cheminformatic analysis. Phenotypic high‐throughput screening of β‐glucuronidase activity uncovers several hits. Further in vivo screening confirms that these hits can induce resistance in rice to nymphs of the brown planthopper Nilaparvata lugens. This work validates the combination of diversity‐oriented synthesis and high‐throughput screening of β‐glucuronidase activity as a strategy for discovering new chemical elicitors. John Wiley and Sons Inc. 2016-12-09 /pmc/articles/PMC5288756/ /pubmed/28168155 http://dx.doi.org/10.1002/open.201600118 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Full Papers He, Xingrui Chen, Xia Lin, Songbo Mo, Xiaochang Zhou, Pengyong Zhang, Zhihao Lu, Yaoyao Yang, Yu Gu, Haining Shang, Zhicai Lou, Yonggen Wu, Jun Diversity‐Oriented Synthesis of Natural‐Product‐like Libraries Containing a 3‐Methylbenzofuran Moiety for the Discovery of New Chemical Elicitors |
title | Diversity‐Oriented Synthesis of Natural‐Product‐like Libraries Containing a 3‐Methylbenzofuran Moiety for the Discovery of New Chemical Elicitors |
title_full | Diversity‐Oriented Synthesis of Natural‐Product‐like Libraries Containing a 3‐Methylbenzofuran Moiety for the Discovery of New Chemical Elicitors |
title_fullStr | Diversity‐Oriented Synthesis of Natural‐Product‐like Libraries Containing a 3‐Methylbenzofuran Moiety for the Discovery of New Chemical Elicitors |
title_full_unstemmed | Diversity‐Oriented Synthesis of Natural‐Product‐like Libraries Containing a 3‐Methylbenzofuran Moiety for the Discovery of New Chemical Elicitors |
title_short | Diversity‐Oriented Synthesis of Natural‐Product‐like Libraries Containing a 3‐Methylbenzofuran Moiety for the Discovery of New Chemical Elicitors |
title_sort | diversity‐oriented synthesis of natural‐product‐like libraries containing a 3‐methylbenzofuran moiety for the discovery of new chemical elicitors |
topic | Full Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5288756/ https://www.ncbi.nlm.nih.gov/pubmed/28168155 http://dx.doi.org/10.1002/open.201600118 |
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