海洋来源杂色曲霉次级代谢产物及其抗植物病原细菌活性

doi:10.3864/j.issn.0578-1752.2020.19.010

Abstract

Abstract:

【Objective】 Plant bacterial diseases are becoming more and more serious, and lack of control pesticides. The objective of this study is to isolate bioactive compounds from the previously obtained marine-derived fungus Aspergillus versicolor D5 with antibacterial activity and abundant secondary metabolites, identify their chemical structures, evaluate their anti-phytopathogenic bacterial activity, so that to clarify the antibacterial components of the target fungus. This research will provide lead compounds for the discovery of new antibacterial pesticides.【Method】The compounds were isolated by silica gel column chromatography (CC), octadecylsilyl silica gel CC, Sephadex LH-20 CC, and semipreparative HPLC, and were identified by modern spectral analysis methods including NMR and MS spectra. In addition, the actibacterial activity of the isolated compounds towards six phytopathogenic bacteria, including Acidovorax avenae, Erwinia carotovora, Clavibater michiganensis, Pseudomonas syringae, Ralstonia solanacearum and Xanthomonas campestris, was evaluated by double dilution method to obtain the minimum inhibitory concentration (MIC).【Result】Twelve compounds were isolated and identified from the ethyl acetate extract of the marine-derived fungus A. versicolor D5 fermented by potato dextrose water media, including four 4-aryl-quinolin-2-one alkaloids, viridicatin (1), 3-O-methylviridicatin (2), 3,6-O-dimethylviridicatin (3), and 3-O-methylviridicatol (4), two dioxopiperazine alkaloids, (+)-cyclopenol (5) and (-)-cyclopenol (6), three fumiquinazolines alkaloids and their derivatives, versicoloid A (7), chrysopiperazine C (8), and cottoquinazoline A (9), and three anthraquinone derivatives, versiconol (10), averufin (11), and noraverufanin (12). Among them, a 4-aryl-quinolin-2-one alkaloid, 3,6-O-dimethylviridicatin (3) exhibited an obvious antibacterial activity against R. solanacearum and X. campestris with MIC values of 50 and 100 μg·mL^-1, respectively. The structure activity relationship analysis revealed that the methoxy group at C-6 might play an important role in anti-phytopathogenic bacterial activity.【Conclusion】The metabolites of A. versicolor D5 are abundant, which can produce alkaloids and anthraquinones with various structures. Among them, nine alkaloids and three anthraquinones were obtained from cultures of D5. 3,6-O-dimethylviridicatin (3) exhibited clear antibacterial activities towards R. solanacearum and X. campestris.

Key words: marine-derived fungus, Aspergillus versicolor, alkaloid, anthraquinone, structural identification, phytopathogenic bacteria

FU Bing,WANG Mei,LIU JianYang,LIN Wei,ZHANG ChengSheng,ZHAO DongLin. Secondary Metabolites from a Marine-Derived Fungus Aspergillus versicolor and Their Anti-Phytopathogenic Bacterial Activity[J].Scientia Agricultura Sinica, 2020, 53(19): 3964-3974.

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References 36

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化合物浓度 Concentration (μg·mL^-1)	加药Dose青枯雷尔氏菌 R. solanacearum OD₆₀₀值OD₆₀₀value	加药Dose野油菜黄单胞菌 X. campestris OD₆₀₀值OD₆₀₀value
200	0.0917	—
	0.0885	—
	0.0835	—
100	0.0902	0.0891
	0.0947	0.0790
	0.0958	0.0788
50	0.1364	1.0253
	0.1504	1.0450
	0.1448	1.0277
25	0.2496	1.0800
	0.2457	1.0953
	0.2458	1.0898
12.5	0.4333	1.0911
	0.4246	1.0891
	0.4340	1.1001
6.25	—	1.1058
	—	1.0913
	—	1.0943

Secondary Metabolites from a Marine-Derived Fungus Aspergillus versicolor and Their Anti-Phytopathogenic Bacterial Activity

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