Isochromenones, isobenzofuranone, and tetrahydronaphthalenes produced by Paraphoma radicina, a fungus isolated from a freshwater habitat

Abstract

Six isochromenones (1-6), clearanols F (5) and G (6), one isobenzofuranone (7), and two tetrahydronaphthalene derivatives (8 and radinaphthalenone (9)), were isolated and identified from a culture of the fungus Paraphoma radicina, which was isolated from submerged wood in a freshwater lake. Compounds 5, 6 and 9 were previously unknown. The structures were elucidated using a set of spectroscopic and spectrometric techniques; the absolute configurations of compounds 5 and 6 were determined by comparison of their experimental ECD measurements with values predicted by TDDFT calculations. Compounds 1-9 were evaluated for antimicrobial activity against an array of bacteria and fungi. The inhibitory activity of compound 4 against Staphylococcus aureus biofilm formation was evaluated.

Fungal Identification Using Molecular Tools: A Primer for the Natural Products Research Community

“…The consensus sequence of the ITS region is submitted for a BLAST search using the NCBI GenBank database to obtain species-level information and then utilized in combination with the D1/D2 regions of the LSU for subsequent phylogenetic analyses. 39,172,176 …”

Isochromanone derivatives from the endophytic fungus Fusarium sp. PDB51F5

“…One new isochromenone, fusaraisochromenone (1), and one new isochromanone, fusaraisochromanone (2) (Fig. 1), were isolated from the broth extract (ethyl acetate) together with 11 known compounds; (R)-3,4-dihydro-4,8-dihydroxy-6-methoxy-4,5-dimethyl-3-methyleneisochromen-1-one (3), 4 8-O-methyljavanicin (4), 5 3-acetyl-7-hydroxy-5-methoxyl-3H-isobenzofuran-l-one (5), 6 curvulin (6), 7 fusalanipyrone (7), 8 daidzein (8), 9 formononetin (9), 9 7-O-methyl genistein (10), 10 kakkatin (11), 10 p-hydroxy benzoic acid (12), 11 and tyrosol (13). 12 All of the compounds (1-13) were isolated using chromatographic techniques (see ESI) and their structures elucidated from spectroscopic data (IR, UV, 1D, and 2D NMR and by mass spectrometry).…”

New α-pyrone and phthalide from the Xylariaceae fungus

“…[21], Paraphoma sp. [22], Angelica sinensis [23], and Ligusticum chuanxiong Hort [24]. They exhibit a variety of Journal of Asian Natural Products Research 3 biological activities, for instant, antibacterial [19], antifungal [20], and antioxidant [21].…”