Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2017 Mar 13;15(3):69.
doi: 10.3390/md15030069.

New Metabolites and Bioactive Chlorinated Benzophenone Derivatives Produced by a Marine-Derived Fungus Pestalotiopsis heterocornis

Affiliations

New Metabolites and Bioactive Chlorinated Benzophenone Derivatives Produced by a Marine-Derived Fungus Pestalotiopsis heterocornis

Hui Lei et al. Mar Drugs. .

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.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
Structures of Compounds 18.
Figure 2
Figure 2
Single crystal X-ray structure of 1.
Figure 3
Figure 3
Electronic circular dichroism (ECD) spectra of 1 and 2.
Figure 4
Figure 4
1H-1H COSY (correlation spectroscopy) HMBC (heteronuclear multiple-bond correlation spectroscopy) correlations of 5 and NOE (nuclear overhauser effect) correlations of 4 and 5. Fragment I: -CH-CH=CH-CH3; Fragment II: -CH(OH)CHCH2CH2CH3; Fragment III: The moiety in the blue dotted line box.

Similar articles

Cited by

References

    1. Yang X.Y., Zhang J.Z., Luo D.Q. The taxonomy, biology and chemistry of the fungal Pestalotiopsis genus. Nat. Prod. Rep. 2012;29:622–641. doi: 10.1039/c2np00073c. - DOI - PubMed
    1. 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
    1. 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
    1. Li J., Xie J., Yang Y.H., Li X.L., Zeng Y., Zhao P.J. Pestalpolyols A-D, cytotoxic polyketides from Pestalotiopsis sp. cr013. Planta Med. 2015;81:1285–1289. doi: 10.1055/s-0035-1546257. - DOI - PubMed
    1. Hwang I.H., Swenson D.C., Gloer J.B., Wicklow D.T. Disseminins and spiciferone analogues: Polyketide-derived metabolites from a fungicolous isolate of Pestalotiopsis disseminate. J. Nat. Prod. 2016;79:523–530. doi: 10.1021/acs.jnatprod.5b00907. - DOI - PubMed

MeSH terms