Journal
JOURNAL OF NATURAL PRODUCTS
Volume 82, Issue 7, Pages 1971-1978Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.9b00366
Keywords
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [163446]
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Seven new cyclic depsipeptides, clavariopsins C I (3-9), together with two known congeners, clavariopsins A and B (1 and 2), were isolated from the aquatic hyphomycete Clavariopsis aquatica. Their planar structures, which consist of nine amino acids and one alpha-hydroxy acid, were elucidated by NMR spectroscopy and HRESIMS. The absolute configurations were established by the advanced Marfey's method and chiral-phase HPLC analysis. Their antifungal and cytotoxic activities were evaluated against six plant pathogenic fungi (Botrytis cinerea, Magnaporthe oryzae, Colletotrichum orbiculare, Fusarium oxysporum, Alternaria alternata, and Aspergillus niger) and a cancer cell line (HeLa-S3), respectively. The majority of the compounds exhibited potent antifungal activity against the fungi tested (minimum inhibition dose = 0.01-10 mu g/disk) and induced hyphal swelling in A. niger (minimum effective dose = 0.3-3 mu g/disk), whereas the compounds exhibited no cytotoxicity toward the cancer cell line. The results suggest that the clavariopsins could be a promising class of antifungal agents.
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