Abstract
Seven novel compounds, namely peniresorcinosides A–E (1–5), penidifarnesylin A (6), and penipyridinone A (7), together with the 11 known ones 8–17, were isolated from a culture of the marine-associated fungus Penicillium sp. ZZ1750 in rice medium. The structures of the new compounds were established based on their high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, extensive nuclear magnetic resonance (NMR) spectroscopic analyses, chemical degradation, Mosher’s method, 13C-NMR calculations, electronic circular dichroism (ECD) calculations, and single crystal X-ray diffraction. Peniresorcinosides A (1) and B (2) are rare glycosylated alkylresorcinols and exhibited potent antiglioma activity, with IC50 values of 4.0 and 5.6 µM for U87MG cells and 14.1 and 9.8 µM for U251 cells, respectively.
Highlights
Introduction from the MarineSourced FungusGliomas are one of the most common types of primary brain tumors and despite advances in cancer therapy, have remained challenging to treat [1]
The theoretical calculation of electronic circular dichroism (ECD) was conducted in MeOH using Timedependent Density functional theory (TD-density functional theory (DFT)) at the B3LYP/6-311+g (d, p) level
Chemical investigation of the metabolites produced by the marine-sourced fungus
Summary
Gliomas are one of the most common types of primary brain tumors and despite advances in cancer therapy, have remained challenging to treat [1]. Marine fungi are important resources for the discovery of novel bioactive natural products and drug lead compounds [5,6,7,8,9,10,11]. We have carried out research on the discovery of natural products from marine microorganisms with antiproliferative activity against human glioma cells. These studies have resulted in the isolation and identification of a number of novel compounds with potent antiglioma activity, including the polycyclic anthraquinones N-acetyl-Ndemethylmayamycin and streptoanthraquinone A from Streptomyces sp. We report the details of the isolation, structure elucidation and antiglioma activity evaluation of all isolated compounds.
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