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. 2023 Dec 26;22(1):15.
doi: 10.3390/md22010015.

Pestalotiopols E-J, Six New Polyketide Derivatives from a Marine Derived Fungus Pestalotiopsis sp. SWMU-WZ04-1

Affiliations

Pestalotiopols E-J, Six New Polyketide Derivatives from a Marine Derived Fungus Pestalotiopsis sp. SWMU-WZ04-1

Liyuan Jiang et al. Mar Drugs. .

Abstract

Chemical epigenetic cultivation of the sponge-derived fungus Pestalotiopsis sp. SWMU-WZ04-1 contributed to the identification of twelve polyketide derivatives, including six new pestalotiopols E-J (1-6) and six known analogues (7-12). Their gross structures were deduced from 1D/2D NMR and HRESIMS spectroscopic data, and their absolute configurations were further established by circular dichroism (CD) Cotton effects and the modified Mosher's method. In the bioassay, the cytotoxic and antibacterial activities of all compounds were evaluated. Chlorinated benzophenone derivatives 7 and 8 exhibited inhibitory effects on Staphylococcus aureus and Bacillus subtilis, with MIC values varying from 3.0 to 50 μg/mL. In addition, these two compounds were cytotoxic to four types of human cancer cells, with IC50 values of 16.2~83.6 μM. The result showed that compound 7 had the probability of being developed into a lead drug with antibacterial ability.

Keywords: Pestalotiopsis sp.; antibacterial activity; cytotoxicity; polyketide; sponge-derived fungus.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of compounds 112.
Figure 2
Figure 2
COSY and key HMBC correlations of 1, 3, 5.
Figure 3
Figure 3
CD spectra of 14 as well as Mo2(AcO)4-induced CD spectra 12.
Scheme 1
Scheme 1
Plausible biosynthetic pathway of compounds 16, 11, 12.
Figure 4
Figure 4
Representative docking poses of compounds 7 and 8 bound to Bcl-2 (PDB ID: 4LVT). The intermolecular interactions between Bcl-2 (PDB ID: 4LVT) and compounds 7 and 8 are as depicted in the maps (a,c) and the maps (b,d).

References

    1. Zhang B., Zhang T., Xu J., Lu J., Qiu P., Wang T., Ding L. Marine sponge-associated fungi as potential novel bioactive natural product sources for drug discovery. Mini Rev. Med. Chem. 2020;20:1966–2010. doi: 10.2174/1389557520666200826123248. - DOI - PubMed
    1. Pan R., Bai X.L., Chen J.W., Zhang H.W., Wang H. Exploring structural diversity of microbe secondary metabolites using OSMAC strategy: A literature review. Front. Microbiol. 2019;10:294. doi: 10.3389/fmicb.2019.00294. - DOI - PMC - PubMed
    1. Zhang X., Hindra, Elliot M.A. Unlocking the trove of metabolic treasures: Activating silent biosynthetic gene clusters in bacteria and fungi. Curr. Opin. Microbiol. 2019;51:9–15. doi: 10.1016/j.mib.2019.03.003. - DOI - PubMed
    1. Jiang P., Fu X.J., Niu H., Chen S.W., Liu F.F., Luo Y., Zhang D., Lei H. Recent advances on Pestalotiopsis genus: Chemistry, biological activities, structure–activity relationship, and biosynthesis. Arch. Pharmacal Res. 2023;46:449–499. doi: 10.1007/s12272-023-01453-2. - DOI - PubMed
    1. Wang X.R., Filho J.G.S., Hoover A.R., King J.B., Ellis T.K., Powell D.R., Cichewicz R.H. Chemical epigenetics alters the secondary metabolite composition of guttate excreted by an atlantic-forest-soil-derived Penicillium citreonigrum. J. Nat. Prod. 2010;73:942–948. doi: 10.1021/np100142h. - DOI - PMC - PubMed

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