New pyrones and their analogs from the marine mangrove-derived Aspergillus sp. DM94 with antibacterial activity against Helicobacter pylori.

Xiaoshuang Gou, Jia Jia, Yaxin Xue, Wenjuan Ding, Zhitong Dong, Danmei Tian, Mei Chen, Hongkai Bi, Kui Hong, Jinshan Tang

Applied microbiology and biotechnology 2020 Sep

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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-ESI-MS, 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.

Citation

Xiaoshuang Gou, Jia Jia, Yaxin Xue, Wenjuan Ding, Zhitong Dong, Danmei Tian, Mei Chen, Hongkai Bi, Kui Hong, Jinshan Tang. New pyrones and their analogs from the marine mangrove-derived Aspergillus sp. DM94 with antibacterial activity against Helicobacter pylori. Applied microbiology and biotechnology. 2020 Sep;104(18):7971-7978