Abstract
Nine new secondary metabolites, including six isocoumarin analogues, 7-hydroxyoospolactone (1), 7-methoxyoospolactone (2), 7-methoxy-9-hydroxyoospolactone (3), 10-acetoxy-9-hydroxyoospolactone (4), 6-dehydroxysescandelin (5), parapholactone (6), and three compounds with a rare skeleton of isocoumarin coupled with phenylethylamine, namely paraphamide A (12), paraphamide B (13), and paraphamide C (14), together with five known compounds, oospolactone (7), 8-O-methyloospolactone (8), 10-hydroxyoospolactone (9), 9,10-dihydroxyoospolactone (10), and oospoglycol (11), were isolated and identified from the marine-derived fungus Paraphoma sp. CUGBMF180003. Their chemical structures were determined using spectroscopic data, including HRESIMS and 1D and 2D NMR techniques. Furthermore, the stereogenic carbons in 5 and 14 were determined by comparing the experimental and calculated electronic circular dichroism (ECD) spectra. The carbon skeleton of 12–14 was identified as the first example of isocoumarin coupled with phenylethylamine derivatives. All of these compounds were examined for antimicrobial activities against Candida albicans and Staphylococcus aureus. Both 1 and 6 showed antibacterial activity against S. aureus with MIC values of 12.5 μg/mL.
Highlights
The Paraphoma fungi are commonly isolated from soil samples or plants and recognized as soil-borne pathogens [1,2]
Our present chemical investigation on the marine-derived fungus Paraphoma sp. strain CUGBMF180003, isolated from a mud sample collected from Shenzhen, China, led to the identification of nine new secondary metabolites, including six isocoumarin analogues, namely, 7hydroxyoospolactone (1), 7-methoxyoospolactone (2), 7-methoxy-9-hydroxyoospolactone
(6), three compounds with a rare skeleton of isocoumarin coupled with phenylethylamine, namely, paraphamide A (12), paraphamide B (13), and paraphamide C (14), as well
Summary
The Paraphoma fungi are commonly isolated from soil samples or plants and recognized as soil-borne pathogens [1,2]. Strains belonging to this genus have been proven to degrade plastic films such as poly(butylene succinate-co-butylene adipate) and poly(butylene succinate) [3,4]. Some secondary metabolites, such as polyketides [5], phenol, latam [6], and isochromenones [7] have been identified in fungi of this genus. Drugs 2021, 19, 313 as five known compounds, oospolactone (7) [8], 8-O-methoxyoospolactone (8) [9], 10-hyas five known compounds, oospolactone (7) [8], 8-O-methoxyoospolactone (8) [9],(11)
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