Ophiocerol, a novel macrocylic neolignan from the aquatic fungus Ophioceras dolichostomum YMF1.00988

Abstract

From cultural filtrates of the freshwater fungus Ophioceras dolichostomum YMF1.00988 a novel neolignan with an unprecedented dibenzo-1,6-dioxacyclodecane carbon skeleton, ophiocerol (1), was isolated, and the known compounds isoamericanoic acid A (2) and caffeic acid (3) were identified. The structure of the novel compound was determined by interpretation of its spectroscopic data, including 1D and 2D, (1)H and (13)C NMR (COSY, HMQC, HMBC, NOESY), and MS. Compounds 1-3 were assayed for their nematicidal activity against Bursaphelenchus xylophilus as well as their antifungal activity against several plant pathogen fungi.

Natural nematicidal metabolites and advances in their biocontrol capacity on plant parasitic nematodes

“…In addition, isoamericanoic acid A 303 isolated from this fungus exhibited activity against B. xylophilus , with an LC 50 value of 133.7 μg mL −1 . 125 Nematicidal compounds 4-hydroxybenzoic acid 296 , methyl 4-hydroxybenzoate 304 , and methyl 2-(4-hydroxyphenyl) acetate 305 were produced by F. oxysporum 162 . They exhibited activity against M. incognita with LC 50 values of 104.84, 253.24, and 149.22 μg mL −1 respectively, after 72 h. 57 4-Hydroxyphenylacetic acid (4-HPA) 306 was isolated from Oidiodendron species, and exhibited nematicidal activity against Pratylenchus penetrans and B. xylophilus .…”

Freshwater Fungi as a Source of Chemical Diversity: A Review

“…From an antifungal extract of the fungus Ophioceras dolichostomum (strain YMF1.00988), the unprecedented new neolignan ophiocerol ( 134 ), along with the known compounds isoamericanoic acid A ( 135 ) and caffeic acid ( 136 ) were isolated. This fungus was obtained from a submerged woody substrate collected from a freshwater habitat in Yunnan Province, China . Compounds 134 – 136 were tested against eight plant pathogens, Exserohilum turcicum , Fusarium sp., Paecilomyces lilacinus , Phyllosticta sp., Alternaria sp., Aspergillus niger , Coleosporium sp., and Colletotrichum sp.…”

“…using a dose-dependent paper-disc diffusion assay. From these, 134 – 136 showed moderate antifungal activity, with compound 136 being the most potent with the inhibition zones ranging from 7 to 17 mm at 50 μg in 50% aqueous DMSO per disc …”