New pyrones and their analogs from the marine mangrove-derived Aspergillus sp. DM94 with antibacterial activity against
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APPLIED MICROBIAL AND CELL PHYSIOLOGY
New pyrones and their analogs from the marine mangrove-derived Aspergillus sp. DM94 with antibacterial activity against Helicobacter pylori Xiaoshuang Gou 1 & Jia Jia 2 & Yaxin Xue 3 & Wenjuan Ding 1 & Zhitong Dong 3 & Danmei Tian 1 & Mei Chen 1 & Hongkai Bi 2 & Kui Hong 3 & Jinshan Tang 1 Received: 24 April 2020 / Revised: 23 June 2020 / Accepted: 19 July 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract Marine fungi are well known for their ability to produce a multitude of natural products and have been proved to be a particularly rich source of drug leads. Here, 20 pyrones and their analogs (1–20), including two new compounds (1 and 6), were obtained from a marine-derived fungus strain of Aspergillus sp. DM94. Their structures were determined by analyses of UV, IR, HR-ESIMS, and NMR data. The ability to inhibit Helicobacter pylori in vitro was assessed for these isolated compounds. Results showed that the bis-naphtho-γ-pyrones exhibited potent antibacterial activity against both the standard and multidrug-resistant H. pylori strains. Structure-activity relationship (SAR) analysis suggested that the bis-naphtho[2,3-b]pyrones showed better anti-H. pylori activity than a hybrid of naphtho[2,3-b]pyrone and naphtho[1,2-b]pyrone. In addition, the free hydroxyl group of the C-8 position in the lower unit is vital for its anti-H. pylori activity. Importantly, compound 18 showed a synergistic effect in combination with amoxicillin, clarithromycin, or metronidazole, suggesting its potential use to overcome antibiotic resistance of H. pylori. This study shed light on the discovery of new anti-H. pylori agents. Key points • New pyrones discovered from a marine-derived fungus Aspergillus sp. DM94. • Bis-naphtho-γ-pyrones showed potent anti-H. pylori activity. • The anti-H. pylori SAR analysis of bis-naphtho-γ-pyrones was discussed. • Bis-naphtho-γ-pyrone 18 showed synergistic effect with clinical antibiotics. Keywords Aspergillus sp. . Chemical constituent . Pyrone . Anti-Helicobacter pylori . Structure-activity relationship (SAR)
Xiaoshuang Gou and Jia Jia contributed equally to this work. Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00253-020-10792-9) contains supplementary material, which is available to authorized users. * Hongkai Bi [email protected]
1
Institute of Traditional Chinese Medicine and Natural Products, International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education (MOE), College of Pharmacy, Jinan University, Guangzhou 510632, China
2
Department of Pathogen Biology, Jiangsu Key Laboratory of Pathogen Biology, Nanjing Medical University, Nanjing 211166, China
3
Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, China
* Kui Hong [email protected] * Jinshan Tang [email protected]
Appl Microbiol
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