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.

Naturally Occurring Isocoumarins Derivatives from Endophytic Fungi: Sources, Isolation, Structural Characterization, Biosynthesis, and Biological Activities

“…Compounds 51, 146, and 147 possessed antibacterial potential towards B. subtilis (MICs 100, 50, and 25 µg/mL, respectively) and S. aureus (MICs 100, 25, and 25 µg/mL, respectively), compared to ciprofloxacin (MICs 0.25 and 0.13 µg/mL, respectively). However, they were inactive against E. coli, C. albicans, C. parapsilosis, and Cryptococcus neoformans [75]. The new isocoumarins 261-266 which were produced by Aspergillus sp.…”

Cytotoxic Polyketides from the Marine Sponge-Derived Fungus Pestalotiopsis heterocornis XWS03F09

“…Recently, we reported sixteen new compounds including heterocornols A-L [11], pestaloisocoumarins A and B, isopolisin B, and pestalotiol A [12], from the fungus Pestalotiopsis heterocornis (XWS03F09), which have been shown to exhibit cytotoxic and antibacterial activities in vitro. In order to obtain more new bioactive natural products from species of this genus, a strain of Pestalotiopsis heterocornis was refermented in the same culture medium.…”

New Dihydroisocoumarin Root Growth Inhibitors From the Sponge-Derived Fungus Aspergillus sp. NBUF87

“…Almost 400 isocoumarins and dihydroisocoumarins have been reported to date, and these compounds have been found to be of broad interest across many pharmacological applications (Saeed, 2016;Chen M. et al, 2019). For example, isocoumarin derivatives from some marine-derived fungi are found to possess a wide range of biological properties including enzyme inhibitory (Kim et al, 2015;Chen S. et al, 2016;Wiese et al, 2016;Cai et al, 2018), cytotoxic (Wang et al, 2019;Wu et al, 2019), antibacterial (Li S. et al, 2012;Lei et al, 2017;Chen Y. et al, 2018;Wang et al, 2019), antiproliferative (Tsukada et al, 2011), anti-food allergic (Niu et al, 2018), as well as anti-inflammatory (Kim et al, 2015;Chen Y. et al, 2018;Liu et al, 2018) activities.…”