Alkylated Salicylaldehydes and Prenylated Indole Alkaloids from the Endolichenic Fungus Aspergillus chevalieri and Their Bioactivities
| Autor: | Wen-Bo Han, Li-Bin Lin, Yi-Meng Wang, Rui Han, Jin-Ming Gao, Qiang Zhang, Yi-Jie Zhai, Yu-Qi Gao, Wenli Li, Jian Xiao |
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| Rok vydání: | 2021 |
| Předmět: |
0106 biological sciences
Indole test Antioxidant biology Indole alkaloid Chemistry Stereochemistry medicine.medical_treatment 010401 analytical chemistry Bacillus cereus General Chemistry Fungus biology.organism_classification 01 natural sciences 0104 chemical sciences chemistry.chemical_compound Cereus Salicylaldehyde medicine Pseudomonas syringae General Agricultural and Biological Sciences 010606 plant biology & botany |
| Zdroj: | Journal of Agricultural and Food Chemistry. 69:6524-6534 |
| ISSN: | 1520-5118 0021-8561 |
| DOI: | 10.1021/acs.jafc.1c01148 |
| Popis: | Sixteen metabolites, including seven C7-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 μM; 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 μM, 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. |
| Databáze: | OpenAIRE |
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