Abstract
Eighteen polyketides (1–18) including six citrinin derivatives, two phenol derivatives, one cyclopentenone, two naphthol derivatives, and seven tetralone derivatives were isolated from the culture broth of a marine-derived fungal strain Xylariaceae sp. SCSGAF0086. Five of these compounds (1, 2, 8, 9, and 10) were new, and their structures were determined by spectroscopic methods. Compounds 4, 6, 7, and 17 showed enzyme-inhibitory activities towards several tested enzymes, and 6 and 7 showed strong antifouling activity against Bugula neritina larvae settlement. This is the first time that the antifouling and enzyme-inhibitory activities of these compounds has been reported.
Highlights
Gorgonian surfaces are frequently colonized by diverse fungi
The 13C NMR and DEPT spectra revealed the presence of 19 carbon signals including five methyls [δC 9.5 (Me-13), 18.2 (Me-11), 19.9 (Me-12), 29.4], two methylenes [δC 49.8 (C-15), 55.5 (C-17)], three methines [δC 35.0 (C-4), 65.3 (C-1), 71.5 (C-3)], one oxyquaternary carbon, one fully substituted phenyl ring [δC 101.7 (s, C-7), 109.4 (s, C-5), 110.6 (s, C-9), 139.5 (s, C-10), 155.7 (s, C-8), 158.4 (s, C-6)], one carboxyl group, and one carbonyl group
DEPT spectra revealed the presence of 19 carbon signals including one methyl, one oxymethyl, a sugar moiety [δC 63.3 (t, C-6′), 69.9 (d, C-4′), 74.0 (d, C-3′), 74.5 (d, C-5′), 75.8 (d, C-2′), 105.1 (d, carbons [δC 101.3 (C-1)′)], ten aromatic carbons [δC 108.5 (d, C-2), 114.7 (d, C-7), 118.4 (s, C-9), 122.1 (d, C-4), 124.2 (d, C-5), 126.4 (d, C-6), 126.5 (d, C-3), 136.2 (s, C-10), 155.0 (s, C-1), 155.6 (s, C-8)], and one carboxyl group [δC 171.6 (COOCH3)]
Summary
Gorgonian surfaces are frequently colonized by diverse fungi. These symbiotic fungi are becoming new sources of various bioactive compounds [1,2,3,4,5]. These polyketides included six citrinin derivatives, two phenol derivatives, one cyclopentenone, two naphthol derivatives, and seven tetralone derivatives, which displayed the diversity of secondary metabolites of the marine-derived fungal strain. Five of these compounds (1, 2, 8, 9, and 10) were new, and the other compounds were identified as 1-acetonyl-7-carboxyl-6,8-dihydroxy-3,4,5-trimethylisochroman (3) [6], dihydrocitrinone (4) [7], stoloniferol B (5) [7], dicitrinin A (Wakana named it penicitrinone A, 6) [8,9], phenol A acid (7) [9], 8-methoxy-1-naphthyl β-glucopyranoside (11) [10], (±)-scytalone (12) [11],. (4R)-(−)-5-O-methylsclerone (13) [12], (4R)-(−)-4,8-dihydroxy-1-tetralone (14) [13,14], (4R)-(−)-regiolone (15) [15], (4R)-(−)-5-hydroxy-4-methoxy-1-tetralone (16) [16], (3R,4S)-(+)-4-hydroxy-6-deoxyscytalone (17) [17], and (3S,4R)-(+)-3,4,5-trihydroxy-1-tetralone (18) [18]
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