A novel oxybis cresol verticilatin with highly varying degrees of biological activities from the insect pathogenic fungus Paecilomycesverticillatus

Abstract

A novel oxybis cresol compound named verticilatin (1), together with two known compounds, 5-methylresorcinol (2) and 2,4-dihydroxy-3,6-dimethylbenzaldehyde (3), was isolated from cultures of the insect pathogenic fungi Paecilomyces verticillatus. The structures of compounds were determined by extensive spectroscopic analysis of HR-ESI-MS and 1D and 2D NMR including HSQC, HMBC, COSY, and ROESY. Fortunately, compound 1 exhibited significant inhibitory activities against CDC25B, cathepsin B, MEG2, and SHP2 enzyme, with IC50 values of 11.5, 3.5, 7.8, and 15 μg/ml, respectively.

New Phenol Derivatives from the Haima Cold Seep-Derived Fungus Aspergillus subversicolor CYH-17

“…Compound 6 was purified as a yellow oil with the molecular formula of C 19 H 20 O 5 according to the molecular ion peak at m / z 329.1393 [M + H] + (calculated for C 19 H 21 O 5 , 329.1384), indicating 10 degrees of unsaturation. The NMR data of 6 were close to those of the known compound verticilatin [ 28 ] and the changes were the presence of a carboxyl ( δ C 175.62) and the absence of one methyl group in 6 . This suggested that the carboxyl group might replace the methyl group in 6 .…”

Ferroptosis Inhibitory Compounds from the Deep-Sea-Derived Fungus Penicillium sp. MCCC 3A00126

“…By comparison of the NMR and MS data with those published in the literature, 34 known compounds were identified as 13 xanthones: (7R,8R)-α-diversonolic ester (3) [23,24], aspergillusone B (4) [22], 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (5) [25], yicathin B (6) [26], pinselin (7) [27], sydowinins A (8) and B (9) [28], huperxanthone C (10) [14], 13-O-acetylsydowinin B (11) [29], 8-(methoxycarbonyl)-1-hydroxy-9-oxo-9Hxanthene-3-carboxylic acid (12) [25], huperxanthone A (13) [14], sterigmatocystin (14) [30], 5-methoxysterigmatocystin (15) [31]; six anthraquinones: versicolorin B ( 16) [32], 8-Omethylversicolorin B (17) [33], anthraquinone aversin (18) [34], averufin (19) [35], 6-Omethylaverufin (20) [36], questin (21) [37]; five sesquiteroenoids: (S)-(+)-sydonic acid (22) [38], (S)-(+)-11-dehydrosydonic acid (23) [38], (−)-12-acetoxy-1-deoxysydonic acid (24) [39], (7S,11S)-(+)-12-acetoxysydonic acid (25) [38], (−)-(7R,10R)-iso-10-hydroxysydowic acid (26) [39]; four diphenyl ethers: diorcinol (27) [40], verticilatin (28) [41], (R)-3-((2-(2hydroxypropan-2-yl)-6-methyl-2,3-dihydrobenzofuran-4-yl)oxy)-5-methylphenol (29) [42], (3S)-3,4-dihydro-5-(3-hydroxy-5-methylphenoxy)-2,2,7-trimethyl-2H-chromen-3-ol (30) [43]; one polyketone: 3-hydroxy-5-methylphenyl-2,4-dihydroxy-6-methylbenzoate (31) [44]; four indole alkaloids: brevianamide F (32) [45], notoamide I (33) [46], notoamide C (34) …”

“…[41], (R)-3-((2-(2hydroxypropan-2-yl)-6-methyl-2,3-dihydrobenzofuran-4-yl)oxy)-5-methylphenol (29)[42], (3S)-3,4-dihydro-5-(3-hydroxy-5-methylphenoxy)-2,2,7-trimethyl-2H-chromen-3-ol (30)[43]; one polyketone: 3-hydroxy-5-methylphenyl-2,4-dihydroxy-6-methylbenzoate…”

Molecular Insight into Gene Response of Diorcinol- and Rubrolide-Treated Biofilms of the Emerging Pathogen Stenotrophomonas maltophilia

“…S2 in the supplemental material). Verticilatin was not isolated from natural sources so far, since the structural analysis was incorrect and recently revised ( 36 , 57 ). However, we decided to adhere to the given name “verticilatin” of the structure in this study to avoid confusion.…”