Cladosins L-O, new hybrid polyketides from the endophytic fungus Cladosporium sphaerospermum WBS017

6533b827fe1ef96bd1285da8

RESEARCH PRODUCT

Cladosins L-O, new hybrid polyketides from the endophytic fungus Cladosporium sphaerospermum WBS017

Tibor Kurtán Werner E.g. Müller Rainer Kalscheuer Zhen Liu Peter Proksch Attila Mándi Wei Wu Jungho Lee Feng Pan Dina H. El-kashef Michael Feldbrügge

subject

Acinetobacter baumannii Staphylococcus aureus Antifungal Agents Ustilago Stereochemistry Antineoplastic Agents Microbial Sensitivity Tests Saccharomyces cerevisiae Fungus medicine.disease_cause 01 natural sciences Mice Structure-Activity Relationship 03 medical and health sciences Polyketide Cell Line Tumor Drug Discovery Enterococcus faecalis Ustilago medicine Animals Density Functional Theory Cell Proliferation 030304 developmental biology Pharmacology 0303 health sciences Dose-Response Relationship Drug Molecular Structure biology 010405 organic chemistry Chemistry Organic Chemistry Fritillaria unibracteata Mycobacterium tuberculosis General Medicine biology.organism_classification Antimicrobial Anti-Bacterial Agents 0104 chemical sciences Staphylococcus aureus Polyketides Pseudomonas aeruginosa Fermentation Drug Screening Assays Antitumor Antibacterial activity Cladosporium

description

Abstract The endophytic fungus Cladosporium sphaerospermum WBS017 was obtained from healthy bulbs of Fritillaria unibracteata var. wabuensis. Fermentation of C. sphaerospermum on solid rice medium yielded three new hybrid polyketides, cladosins L−N (1–3), and a known derivative cladodionen (4). Further cultivation of this fungus on white bean medium afforded an additional new hybrid polyketide, cladosin O (5) along with three known analogues (6–8). The structures of the new compounds were elucidated using a combination of NMR and HRESIMS data. The absolute configurations of compounds 2 and 3 were determined by Mosher’s method and TDDFT-ECD calculations. All isolated compounds were evaluated for their cytotoxic and antimicrobial activities. Cladodionen (4) exhibited cytotoxicity against the mouse lymphoma cell line L5178Y with an IC50 value of 3.7 μM, and also exhibited antifungal activity against Ustilago maydis and Saccharomyces cerevisiae, while cladosin L (1) displayed week antibacterial activity against Staphylococcus aureus ATCC 29213 and S. aureus ATCC 700699 with MIC values of 50 and 25 μM, respectively.

year	journal	country	edition	language
2019-11-18	European Journal of Medicinal Chemistry

https://doi.org/10.1016/j.ejmech.2020.112159