JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2023
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IF 6.1
Zhibo Hu,Yujiao Zhu,Junjie Chen,Jun Chen,Chunyuan Li,Zhizeng Gao,Jing Li,Lan Liu
The emerging outbreak of bacterial diseases is a major challenge for the aquaculture industry. The development of new antibacterial agents from natural resources to curb fish bacterial diseases in aquaculture is becoming increasingly popular. In this study, eight new benzoic acid-containing alkaloids, asperalin A–F (1–6), asperalumazine A (7), and N-(3-acetamidopropyl)-3,4-dihydroxybenzamide (8), along with four known compounds (9–12) were isolated and identified from a seagrass-derived Aspergillus alabamensis. Their chemical structures were established on the basis of extensive spectroscopic analyses (including HRESIMS, 1D and 2D NMR spectroscopy), NMR computational methods, and electronic circular dichroism (ECD) calculations. Compounds 1–6 exhibited moderate or potent inhibitory activities against at least one fish pathogenic bacterium, among Edwardsiella ictalurid, Streptococcus iniae, and Streptococcus parauberis, and these compounds represent the first report of the coupling of dihydroquinolone alkaloids with benzoic acid derivatives. Compounds 3 and 4 showed strong activities against Staphylococcus aureus, S. iniae, and S. parauberis, with an MIC value of 10.1, 5.0, and 10.1 μM, respectively. Compound 5, an N-alkylated product of 4, exhibited the strongest inhibitory effects against S. iniae, with an MIC value of 2.2 μM. Notably, compound 6, as a new natural bactericide, showed moderate to potent inhibitory activity toward all strains tested, including one Gram-negative bacterium E. ictalurid (10.9 μM, MIC) and four Gram-positive bacteria S. iniae (43.6 μM, MIC), S. aureus (21.8 μM, MIC), S. parauberis (87.3 μM, MIC), and Bacillus subtilis (21.8 μM, MIC). Compound 7 represents the first example of a lumazine derivative directly coupled to a benzoic acid moiety by a hydroxymethyl group.
研究领域:
水产养殖
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微生物学
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药物化学
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天然产物
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2022
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IF 5.895
Zhibo Hu,Yujiao Zhu,Jun Chen,Junjie Chen,Chunyuan Li,Zhizeng Gao,Jing Li,Lan Liu
Five new carotane sesquiterpenoids (asperalacids A–E (1–5)), one new tricyclic sesquiterpenoid (4-hydroxy-5(6)-dihydroterrecyclic acid A (6)), and two known analogues (7–8) were obtained from a seagrass-derived fungus Aspergillus alabamensis, which was speculated to be a phytopathogenic fungus, isolated from the necrotic leaves of Enhalus acoroides. The structures of 1–6 were established by a combination of spectroscopic methods, including comprehensive NMR analysis, mass spectrometry, conformational analysis, NMR computational methods, and ECD calculations. Compound 4, with higher inhibitory activity on wheat (Triticum aestivum L.) root and shoot elongation than the positive control terbutryn, a broad-spectrum systemic herbicide, is a new natural plant growth inhibitor. Compound 5, belonging to the rare glycosylated sesquiterpenoid class, represents the first example of glycosylated carotane sesquiterpenoid whose sugar moiety was identified as α-d-glucose. Compounds 1–4 and 6 displayed weak to potent antimicrobial activity against the plant pathogenic fungi Fusarium oxysporum, Fusarium graminearum, and Penicillium italicum and the Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus.
研究领域:
药理学
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化学
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微生物学
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植物科学
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DOI
PubMed
高影响因子
PHYTOCHEMISTRY
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2024
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IF 3.2
Zhibo Hu,Haishan Cui,Qiang Wang,Cheng Li,Senhua Chen,Zhizeng Gao,Lan Liu,Bo Peng,Jing Li
Seven previously undescribed compounds, including four diketomorpholine alkaloids ( 1 ‒ 4 ), one indole diketopiperazine alkaloid ( 9 ), one chromone ( 10 ), and one benzoic acid derivative ( 13 ), and nine known compounds ( 5 – 8 , 11 , 12 , and 14 – 16 ) were isolated from two different fungal sources. Nine of these metabolites ( 1 – 9 ) were obtained from a seagrass-derived Aspergillus alabamensis SYSU-6778, while the others were obtained from a mixed culture of A. alabamensis SYSU-6778 and a co-isolated fungus A . fumigatiaffinis SYSU-6786. The chemical structures of the compounds were deduced via spectroscopic techniques (including HRESIMS, 1D and 2D NMR), chemical reactions, and ECD calculations. It is worth noting that compound 10 was identified as a defensive secondary metabolite of strain SYSU-6786, produced through the induction of compound 8 under co-culture conditions. Compounds 3 and 4 possessed a naturally rare isotryptophan core. Moreover, compounds 1 and 2 exhibited potent inhibitory activities against fish pathogenic bacterium Edwardsiella ictalurid, with minimum inhibitory concentration values of 10.0 μg/mL for both compounds.
研究领域:
微生物学
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植物化学
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生物技术
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药理学
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产品关联
DOI
PubMed
高影响因子
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