Alkylated Salicylaldehydes and Prenylated Indole Alkaloids from the Endolichenic Fungus Aspergillus chevalieri and Their Bioactivities
Alkylated Salicylaldehydes and Prenylated Indole Alkaloids from the Endolichenic Fungus Aspergillus chevalieri and Their Bioactivities
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DOI：
10.1021/acs.jafc.1c01148
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发表时间：
2021-06-07
影响因子：
6.1
通讯作者：
Gao, Jin-Ming
中科院分区：
文献类型：
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作者：
Lin, Li-Bin;Gao, Yu-Qi;Gao, Jin-Ming
从地衣内生真菌Aspergillus chevalieri SQ-8中分离得到16种代谢产物，包括7种C-7-烷基化水杨醛衍生物（1-7）和9种异戊二烯化吲哚生物碱（8-16），其中3种为新的，即曲霉蓝蛋白A和B（1和2）以及新棘球蛋白F（8）。银灰素A（1）是一种不寻常的苯并[c]噻吩-1（3 H）-酮骨架的苯酞样衍生物。所有化合物进行了体外抗菌，抗神经炎，抗氧化活性进行了评估。其中曲霉蓝素A和B对两种植物病原菌Pseudomonaslingae pv actinidae（Psa）和Bacilluscereus表现出较强的抗菌活性，MIC值为6.25 μ M;进一步的SEM分析表明，化合物1和2的抑菌机理可能是改变了B的外部结构。结果表明，化合物1和2可作为农药杀菌剂先导化合物的潜在候选化合物。此外，化合物6和10显著抑制一氧化氮的产生，IC 50值为约1.05。12 μ M，并通过分子对接研究了可能的抗炎机制。最后，测试的酚3-5表现出显着的抗氧化效果。因此，菌株SQ-8代表了待利用的这些生物活性代谢物的新资源。
Sixteen metabolites, including seven C-7-alkylated salicylaldehyde derivatives (1-7) and nine prenylated indole alkaloids (8-16), three of which are new, namely, asperglaucins A and B (1 and 2) and neoechinulin F (8), were separated from the endolichenic fungus Aspergillus chevalieri SQ-8. Asperglaucin A (1) represents an unusual phthalide-like derivative with a benzo[c]thiophen-1(3H)-one scaffold. All compounds were assessed in vitro for antibacterial, antineuroinflammatory, and antioxidant activities. Notably, asperglaucins A and B exhibited potent antibacterial activities against two plant pathogens Pseudomonas syringae pv actinidae (Psa) and Bacillus cereus, with an MIC value of 6.25 mu M; further SEM analyses illustrated that the possible bacteriostatic mechanisms for compounds 1 and 2 were to alter the external structure of B. cereus and Psa, and to cause the rupture or deformation of the cell membranes, respectively, and the results suggest that compounds 1 and 2 may serve as potential promising candidates for lead compounds of agrochemical bactericides. Furthermore, compounds 6 and 10 significantly inhibited nitric oxide production with an IC50 value of ca. 12 mu M, and the possible anti-inflammatory mechanisms involved were also studied by molecular docking. Finally, the tested phenolics 3-5 showed significant antioxidative effects. Thus, strain SQ-8 represents a novel resource of these bioactive metabolites to be utilized.