Abstract
Chondrostereum sp., a marine fungus isolated from a soft coral Sarcophyton tortuosum, can yield hirsutane framework sesquiterpenoids. However, the metabolites profiles vary dramatically with the composition change of the culture media. This fungus was cultured in a liquid medium containing glycerol as the carbon source, and two new metabolites, chondrosterins I and J (1 and 2), were obtained. Their structures were elucidated primarily based on MS, NMR and X-ray single-crystal diffraction data. By comparison with the known hirsutane sesquiterpenoids, chondrosterins I and J have unique structural features, including a methyl was migrated from C-2 to C-6, and the methyl at C-3 was carboxylated. Compound 2 exhibited potent cytotoxic activities against the cancer cell lines CNE-1 and CNE-2 with the IC50 values of 1.32 and 0.56 μM.
Highlights
The previous works on the metabolites of marine fungus Chondrostereum sp. afforded a series of new hirsutane sesquiterpenoids, including chondrosterins A (3)–F and hirsutanol E, together with the known compounds hirsutanols A (4), C, F, arthrosporone and incarnal (5) [1,2,3]
In the IR spectrum, the prominent bands at 1736 and 1673 cm−1 indicated the presence of ketone carbonyl and carboxyl groups
The UV maximum absorption at 244 nm indicated the tetrasubstituted double bond connected to the carboxyl group and formed a conjugated system
Summary
The previous works on the metabolites of marine fungus Chondrostereum sp. afforded a series of new hirsutane sesquiterpenoids, including chondrosterins A (3)–F and hirsutanol E, together with the known compounds hirsutanols A (4), C, F, arthrosporone and incarnal (5) [1,2,3]. The metabolite profiles were analyzed by HPLC, and the result showed that the constituent and content of the metabolites extract of glycerol-containing culture were distinct different from those previous glucose containing media (Supplementary Figure S1). The ethyl acetate extract of the culture broth showed significant cytotoxic activity. These preliminary findings suggest that fungus Chondrostereum sp. The metabolite isolation of the marine fungus cultured in glycerol-containing media afforded two new sesquiterpenoids chondrosterins I and J (1 and 2, Figure 1). We report their isolation, structure elucidation, and cytotoxic activities evaluation
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