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A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1

Marine-derived fungi are a promising and untapped reservoir for discovering structurally interesting and pharmacologically active natural products. In our efforts to identify novel bioactive compounds from marine-derived fungi, four breviane spiroditerpenoids, including a new compound, brevione O (1...

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Autores principales: Yang, Beiye, Sun, Weiguang, Wang, Jianping, Lin, Shuang, Li, Xiao-Nian, Zhu, Hucheng, Luo, Zengwei, Xue, Yongbo, Hu, Zhengxi, Zhang, Yonghui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5923397/
https://www.ncbi.nlm.nih.gov/pubmed/29596354
http://dx.doi.org/10.3390/md16040110
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author Yang, Beiye
Sun, Weiguang
Wang, Jianping
Lin, Shuang
Li, Xiao-Nian
Zhu, Hucheng
Luo, Zengwei
Xue, Yongbo
Hu, Zhengxi
Zhang, Yonghui
author_facet Yang, Beiye
Sun, Weiguang
Wang, Jianping
Lin, Shuang
Li, Xiao-Nian
Zhu, Hucheng
Luo, Zengwei
Xue, Yongbo
Hu, Zhengxi
Zhang, Yonghui
author_sort Yang, Beiye
collection PubMed
description Marine-derived fungi are a promising and untapped reservoir for discovering structurally interesting and pharmacologically active natural products. In our efforts to identify novel bioactive compounds from marine-derived fungi, four breviane spiroditerpenoids, including a new compound, brevione O (1), and three known compounds breviones I (2), J (3), and H (4), together with a known diketopiperazine alkaloid brevicompanine G (5), were isolated and identified from an ethyl acetate extract of the fermented rice substrate of the coral-derived fungus Penicillium sp. TJ403-1. The absolute structure of 1 was elucidated by HRESIMS, one- and two-dimensional NMR spectroscopic data, and a comparison of its electronic circular dichroism (ECD) spectrum with the literature. Moreover, we confirmed the absolute configuration of 5 by single-crystal X-ray crystallography. All the isolated compounds were evaluated for isocitrate dehydrogenase 1 (IDH1) inhibitory activity and cytotoxicity, and compound 2 showed significant inhibitory activities against HL-60, A-549, and HEP3B tumor cell lines with IC(50) values of 4.92 ± 0.65, 8.60 ± 1.36, and 5.50 ± 0.67 µM, respectively.
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spelling pubmed-59233972018-05-03 A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1 Yang, Beiye Sun, Weiguang Wang, Jianping Lin, Shuang Li, Xiao-Nian Zhu, Hucheng Luo, Zengwei Xue, Yongbo Hu, Zhengxi Zhang, Yonghui Mar Drugs Communication Marine-derived fungi are a promising and untapped reservoir for discovering structurally interesting and pharmacologically active natural products. In our efforts to identify novel bioactive compounds from marine-derived fungi, four breviane spiroditerpenoids, including a new compound, brevione O (1), and three known compounds breviones I (2), J (3), and H (4), together with a known diketopiperazine alkaloid brevicompanine G (5), were isolated and identified from an ethyl acetate extract of the fermented rice substrate of the coral-derived fungus Penicillium sp. TJ403-1. The absolute structure of 1 was elucidated by HRESIMS, one- and two-dimensional NMR spectroscopic data, and a comparison of its electronic circular dichroism (ECD) spectrum with the literature. Moreover, we confirmed the absolute configuration of 5 by single-crystal X-ray crystallography. All the isolated compounds were evaluated for isocitrate dehydrogenase 1 (IDH1) inhibitory activity and cytotoxicity, and compound 2 showed significant inhibitory activities against HL-60, A-549, and HEP3B tumor cell lines with IC(50) values of 4.92 ± 0.65, 8.60 ± 1.36, and 5.50 ± 0.67 µM, respectively. MDPI 2018-03-29 /pmc/articles/PMC5923397/ /pubmed/29596354 http://dx.doi.org/10.3390/md16040110 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 Communication
Yang, Beiye
Sun, Weiguang
Wang, Jianping
Lin, Shuang
Li, Xiao-Nian
Zhu, Hucheng
Luo, Zengwei
Xue, Yongbo
Hu, Zhengxi
Zhang, Yonghui
A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1
title A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1
title_full A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1
title_fullStr A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1
title_full_unstemmed A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1
title_short A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1
title_sort new breviane spiroditerpenoid from the marine-derived fungus penicillium sp. tj403-1
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5923397/
https://www.ncbi.nlm.nih.gov/pubmed/29596354
http://dx.doi.org/10.3390/md16040110
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