New Metabolites and Bioactive Chlorinated Benzophenone Derivatives Produced by a Marine-Derived Fungus Pestalotiopsis heterocornis
- PMID: 28335391
- PMCID: PMC5367026
- DOI: 10.3390/md15030069
New Metabolites and Bioactive Chlorinated Benzophenone Derivatives Produced by a Marine-Derived Fungus Pestalotiopsis heterocornis
Abstract
Four new compounds, including two isocoumarins, pestaloisocoumarins A and B (1, 2), one sesquiterpenoid degradation, isopolisin B (4), and one furan derivative, pestalotiol A (5), together with one known isocoumarin, gamahorin (3), and three chlorinated benzophenone derivatives, pestalachloride B (6), pestalachloride E (7) and a mixture of pestalalactone atropisomers (8a/8b), were isolated from a culture of the fungus Pestalotiopsis heterocornis associated with sponge Phakellia fusca. These new chemical structures were established using NMR and MS spectroscopic data, as well as single-crystal X-ray crystallographic analysis and CD Cotton effects. All of the isolated compounds were evaluated for their antimicrobial and cytotoxic activities. Isocoumarins 1-3, showed antibacterial activities against Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis with MIC values ranging from 25 to 100 μg/mL and weak antifungal activities. Chlorinated benzophenone derivatives 6-8 exhibited antibacterial activities against S. aureus and B. subtilis with MIC values ranging from 3.0 to 50 μg/mL and cytotoxicities against four human cancer cell lines with IC50 values of 6.8-87.8 μM.
Keywords: Pestalotiopsis heterocornis; antibacterial activity; antifungal activity; cytotoxicity; isocoumarin.
Conflict of interest statement
The authors declare no conflicts of interest.
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References
-
- Akone S.H., Amrani M.E., Lin W.H., Lai D.W., Proksch P. Cytosporins F-K, new epoxyquinols from the endophytic fungus Pestalotiopsis theae. Tetrahedron Lett. 2013;54:6751–6754. doi: 10.1016/j.tetlet.2013.10.005. - DOI
-
- Wang J.F., Wei X.Y., Lu X., Xu F.Q., Wan J.T., Lin X.P., Zhou X.F., Liao S.R., Yang B., Tu Z.C., et al. Eight new polyketide metabolites from the fungus Pestalotiopsis vaccinii endogenous with the mangrove plant Kandelia candel (L.) Druce. Tetrahedron. 2014;70:9695–9701. doi: 10.1016/j.tet.2014.10.056. - DOI
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