Abstract
A novel sesquiterpene methylcyclopentenedione, penicilliumin B (1), was obtained from a deep sea-derived fungus Penicillium sp. F00120, together with three known sesquiterpene cyclohexenones (2–4). Penicilliumin B (1), presenting the first example with the sesquiterpene cyclopentenedione skeleton as natural products, was structurally determined by analysis of the NMR and MS spectroscopic data, while the absolute configurations were assigned by single-crystal X-ray experiments. The plausible biosynthetic pathway of the unusual cyclopentenone skeleton of 1 was proposed. Penicilliumin B (1), with low toxicity, was showed significant potential to inhibit the kidney fibrogenic action in vitro, by a mechanism dependent on disruption of oxidative stress, presenting a new type of promising renoprotective agent.
Highlights
Sesquiterpene quinones/hydroquinones (SQ/SHQ) are common in marine sponges1, seaweed2, and marine or terrestrial microorganisms as well3, 4
F00120 was fermented on a solid rice substrate culture
The EtOAc extract of its solid culture was subjected to silica gel and Sephadex LH-20 column chromatography (CC)
Summary
Our bioactive assay showed sesquiterpene methylcyclopentenedione 1 has nearly no inhibitory activities against eight cancer cells (Supporting Information, Table S1). 1 was inactive in all of the antibacterial (Escherichia coli, Salmonella enterica, Staphylococcus aureus), antituberculosis (M. tuberculosis H37Ra), antiviral (H1N1, H3N2, EV71), and anti-inflammatory (COX-1, COX-2, NF-κB luciferase) assays (Supporting Information, Tables S2−S4 and Figure S1), much different with SQ or sesquiterpene cyclohexenones derivatives, which are owing broad spectrum of biological activities including those above. Penicilliumin B [1] was inactive in cytotoxic, antibacterial, antituberculosis, antiviral, and anti-inflammatory assays, it was showed to be a promising kidney fibrogenic inhibitor by a mechanism dependent on disruption of oxidative stress in RMC cells, with low toxicity. More investigations are needed, our current studies provide proof that penicilliumin B [1] can play potential roles in the therapy of diabetic nephropathy, especially on renal fibrotic lesions, presenting a new type of natural product as promising renoprotective agent
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