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Discovery of Cymopolyphenols A–F From a Marine Mesophotic Zone Aaptos Sponge-Associated Fungus Cymostachys sp. NBUF082
Mesophotic coral ecosystems (MCEs) have complex but understudied biodiversity, especially for natural products discovery. Untargeted metabolomics research on 80 extracts prepared from marine sponge-associated fungi, half from shallow reefs (<30 m) and half from MCEs (30–150 m), facilitated priori...
Autores principales: | , , , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Frontiers Media S.A.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7937805/ https://www.ncbi.nlm.nih.gov/pubmed/33692772 http://dx.doi.org/10.3389/fmicb.2021.638610 |
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author | Wang, Tingting Zhou, Jing Zou, Jiabin Shi, Yutong Zhou, Wenli Shao, Peng Yu, Tianze Cui, Wei Li, Xiaohui Wu, Xingxin Ye, Jing Yan, Xiaojun Naman, C. Benjamin Lazaro, J. Enrico H. He, Shan |
author_facet | Wang, Tingting Zhou, Jing Zou, Jiabin Shi, Yutong Zhou, Wenli Shao, Peng Yu, Tianze Cui, Wei Li, Xiaohui Wu, Xingxin Ye, Jing Yan, Xiaojun Naman, C. Benjamin Lazaro, J. Enrico H. He, Shan |
author_sort | Wang, Tingting |
collection | PubMed |
description | Mesophotic coral ecosystems (MCEs) have complex but understudied biodiversity, especially for natural products discovery. Untargeted metabolomics research on 80 extracts prepared from marine sponge-associated fungi, half from shallow reefs (<30 m) and half from MCEs (30–150 m), facilitated prioritization for further study a Cymostachys fungus from a 103 m deep Aaptos sponge. LC-MS target-directed isolation yielded a series of new compounds, cymopolyphenols A−F (1–6), and two known phenylspirodrimanes, F1839-I (7) and stachybotrylactone (8). This is the first report of natural products from the recently described genus, Cymostachys. Compounds 1–6 and 8 contain a dihydroisobenzofuran moiety, and 4–6 are low-order polymers of 1 with novel scaffolds. The structures of the compounds were established by spectroscopic and spectrometric data interpretation, with further support from X-ray crystallography studies of 3 and 4. Compound 3 undergoes facile racemization in solution and was found to crystalize as a racemic mixture. Compound 5 was also obtained in racemic form, and after chiral chromatography, both separated enantiomers racemized in solution by a presumed keto-enol tautomerization. Compounds 1 and 3–6 were found to be weakly antimicrobial (MIC 16–64 μg/ml) in vitro against several Gram-positive and Gram-negative human or aquatic pathogens, compound 5 was shown to chelate iron in vitro at 10 μM, and 8 activated plant disease resistance in vivo in a transgenic model organism. |
format | Online Article Text |
id | pubmed-7937805 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-79378052021-03-09 Discovery of Cymopolyphenols A–F From a Marine Mesophotic Zone Aaptos Sponge-Associated Fungus Cymostachys sp. NBUF082 Wang, Tingting Zhou, Jing Zou, Jiabin Shi, Yutong Zhou, Wenli Shao, Peng Yu, Tianze Cui, Wei Li, Xiaohui Wu, Xingxin Ye, Jing Yan, Xiaojun Naman, C. Benjamin Lazaro, J. Enrico H. He, Shan Front Microbiol Microbiology Mesophotic coral ecosystems (MCEs) have complex but understudied biodiversity, especially for natural products discovery. Untargeted metabolomics research on 80 extracts prepared from marine sponge-associated fungi, half from shallow reefs (<30 m) and half from MCEs (30–150 m), facilitated prioritization for further study a Cymostachys fungus from a 103 m deep Aaptos sponge. LC-MS target-directed isolation yielded a series of new compounds, cymopolyphenols A−F (1–6), and two known phenylspirodrimanes, F1839-I (7) and stachybotrylactone (8). This is the first report of natural products from the recently described genus, Cymostachys. Compounds 1–6 and 8 contain a dihydroisobenzofuran moiety, and 4–6 are low-order polymers of 1 with novel scaffolds. The structures of the compounds were established by spectroscopic and spectrometric data interpretation, with further support from X-ray crystallography studies of 3 and 4. Compound 3 undergoes facile racemization in solution and was found to crystalize as a racemic mixture. Compound 5 was also obtained in racemic form, and after chiral chromatography, both separated enantiomers racemized in solution by a presumed keto-enol tautomerization. Compounds 1 and 3–6 were found to be weakly antimicrobial (MIC 16–64 μg/ml) in vitro against several Gram-positive and Gram-negative human or aquatic pathogens, compound 5 was shown to chelate iron in vitro at 10 μM, and 8 activated plant disease resistance in vivo in a transgenic model organism. Frontiers Media S.A. 2021-02-22 /pmc/articles/PMC7937805/ /pubmed/33692772 http://dx.doi.org/10.3389/fmicb.2021.638610 Text en Copyright © 2021 Wang, Zhou, Zou, Shi, Zhou, Shao, Yu, Cui, Li, Wu, Ye, Yan, Naman, Lazaro and He. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Microbiology Wang, Tingting Zhou, Jing Zou, Jiabin Shi, Yutong Zhou, Wenli Shao, Peng Yu, Tianze Cui, Wei Li, Xiaohui Wu, Xingxin Ye, Jing Yan, Xiaojun Naman, C. Benjamin Lazaro, J. Enrico H. He, Shan Discovery of Cymopolyphenols A–F From a Marine Mesophotic Zone Aaptos Sponge-Associated Fungus Cymostachys sp. NBUF082 |
title | Discovery of Cymopolyphenols A–F From a Marine Mesophotic Zone Aaptos Sponge-Associated Fungus Cymostachys sp. NBUF082 |
title_full | Discovery of Cymopolyphenols A–F From a Marine Mesophotic Zone Aaptos Sponge-Associated Fungus Cymostachys sp. NBUF082 |
title_fullStr | Discovery of Cymopolyphenols A–F From a Marine Mesophotic Zone Aaptos Sponge-Associated Fungus Cymostachys sp. NBUF082 |
title_full_unstemmed | Discovery of Cymopolyphenols A–F From a Marine Mesophotic Zone Aaptos Sponge-Associated Fungus Cymostachys sp. NBUF082 |
title_short | Discovery of Cymopolyphenols A–F From a Marine Mesophotic Zone Aaptos Sponge-Associated Fungus Cymostachys sp. NBUF082 |
title_sort | discovery of cymopolyphenols a–f from a marine mesophotic zone aaptos sponge-associated fungus cymostachys sp. nbuf082 |
topic | Microbiology |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7937805/ https://www.ncbi.nlm.nih.gov/pubmed/33692772 http://dx.doi.org/10.3389/fmicb.2021.638610 |
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