O1 Isolation and identification of an antimicrobial and cytotoxic chlorated perylenequinone from the symbiotic fungus Aspergillus fumigatus D

Abstract

Perylenequinones are bioactive natural products characterized by a conjugated aromatic pentacyclic dione found in fungi, plants, insects (aphids), and animals (crinoids). Till now, a total of 24 perylenequinone derivatives had been identified from fungi. Bioassay-guided fractionation of the crude extract of the salty broth of Aspergillus fumigatus D endphytic on Edgeworthia chrysantha Lindl. led to the isolation of a chlorated perylenequinone ( 1 ), which was firstly produced by a halotolerant fungus, Alternaria sp. M6. Its chemical structure was unambiguously determined as 8-chloro-3,6a,7,9,10-pentahydroxy-9,8,7,6a-tetrahydroperylen-4(6aH)-one by a combination of spectroscopic techniques, including 1D- and 2D-NMR, ESI-MS. Biological tests showed that compound 1 had potent antimicrobial effects on Escherichia coli and Canidia albicans with MIC values of 0.78 μM, 1.56 μM, respectively, and exhibited moderate in vitro anti-proliferative activity against human lung cancer cell line A549 with an IC 50 value of 12.79 ± 0. 33 μM. It suggests that compound 1 has potential applications for new antibiotic discovery.