Pleosporalone A, the first azaphilone characterized with aromatic A-ring from a marine-derived Pleosporales sp. fungus

Abstract

A fungal strain, Pleosporales sp. CF09-1, was isolated from marine sediment collected from the Bohai Sea. A novel azaphilone derivative, named pleosporalone A (1), along with two known analogues, cohaerins A and B (2 and 3), were obtained and identified from the culture extract of Pleosporales sp. CF09-1. Their planar structures were elucidated by detailed analysis of spectroscopic data and by comparison with related known compounds. Pleosporalone A (1) represents the first azaphilone derivative characterised with A-ring aromatisation. Compound 1 showed strong antifungal activity against three plant pathogenic fungi Botrytis cinerea, Rhizopus oryzae and Phytophthora capsici with the MIC values of 0.39, 0.78 and 0.78 μM, respectively.

Molecular Networking-Based Metabolome and Bioactivity Analyses of Marine-Adapted Fungi Co-cultivated With Phytopathogens

“…and M. oryzae ( Figure 4A and Supplementary Figure 7 ). Azaphilones exhibit antifungal activity against devastating phytopathogens, e.g., B. cinerea , Rhizopus oryzae , and Phytophthora capsici ( Osmanova et al, 2010 ; Cao et al, 2015 ). Mitorubrin was a major compound in the mono-culture of Hypoxylon sp.…”

Metabolites of Marine Sediment-Derived Fungi: Actual Trends of Biological Activity Studies

“…Pleosporalone B (70) exhibited potent activities against the fungi Alternaria brassicicola and Fusarium oxysporum. Additionally, pleosporalone C (71) displayed significant activity against the fungus Botryosphaeria dothidea [49,50]. Fusarium oxysporum.…”

Natural Products Research in China From 2015 to 2016

“…CF09-01 (Bohai Sea, China). Compound 38 showed antifungal activity to three plant pathogenic fungi, Rhizopus oryzae, Botrytis cinerea , and Phytophthora capsici , with minimal inhibitory concentration (MIC) values of 0.78, 0.39, and 0.78 μM, more potent than carbendazim (MIC 1.56, 0.78, and 1.56 μM), respectively (Cao et al, 2016a ). Deep sea sediment-derived Penicillium aculeatum SD-321 (South China sea) produced three novel phenolic bisabolane sesquiterpenes, peniciaculins A ( 39 ) and B, and 1-hydroxyboivinianin A. Peniciaculin A ( 39 ) displayed antibacteria activity to Micrococcus luteus and Vibrio alginolyticus with MIC values of 1.0 and 2.0 μg/mL, respectively, comparable to chloramphenicol (8.0 and 0.5 μg/mL).…”