1. Clavariopsins C–I, Antifungal Cyclic Depsipeptides from the Aquatic Hyphomycete Clavariopsis aquatica
- Author
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Ryosuke Fudou, Makoto Ojika, Tomohiko Tomura, Kenichi Kaida, Yuki Sawaki, Chunguang Han, and Thin Wut Soe
- Subjects
Hypha ,Pharmaceutical Science ,01 natural sciences ,Alternaria alternata ,Analytical Chemistry ,Microbiology ,Drug Discovery ,Fusarium oxysporum ,Botrytis cinerea ,Pharmacology ,chemistry.chemical_classification ,Depsipeptide ,biology ,010405 organic chemistry ,Chemistry ,fungi ,Organic Chemistry ,Aspergillus niger ,Colletotrichum orbiculare ,food and beverages ,biology.organism_classification ,0104 chemical sciences ,Amino acid ,010404 medicinal & biomolecular chemistry ,Complementary and alternative medicine ,Molecular Medicine - Abstract
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 α-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 μg/disk) and induced hyphal swelling in A. niger (minimum effective dose = 0.3-3 μg/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.
- Published
- 2019
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