Anthraquinones, Diphenyl Ethers, and Their Derivatives from the Culture of the Marine Sponge-Associated Fungus Neosartorya spinosa KUFA 1047

Abstract

Previously unreported anthraquinone, acetylpenipurdin A (4), biphenyl ether, neospinosic acid (6), dibenzodioxepinone, and spinolactone (7) were isolated, together with (R)-6-hydroxymellein (1), penipurdin A (2), acetylquestinol (3), tenellic acid C (5), and vermixocin A (8) from the culture of a marine sponge-associated fungus Neosartorya spinosa KUFA1047. The structures of the previously unreported compounds were established based on an extensive analysis of 1D and 2D NMR spectra as well as HRMS data. The absolute configurations of the stereogenic centers of 5 and 7 were established unambiguously by comparing their calculated and experimental electronic circular dichroism (ECD) spectra. Compounds 2 and 5–8 were tested for their in vitro acetylcholinesterase and tyrosinase inhibitory activities as well as their antibacterial activity against Gram-positive and Gram-negative reference, and multidrug-resistant strains isolated from the environment. The tested compounds were also evaluated for their capacity to inhibit biofilm formation in the reference strains.

Polyketide Derivatives from the Endophytic Fungus Phaeosphaeria sp. LF5 Isolated from Huperzia serrata and Their Acetylcholinesterase Inhibitory Activities

“…21 (1H, s, H-5), 6.20 (1H, s, H-7), 4.63–4.67 (1H, m, H-3), 2.92 (1H, dd, J = 16.4, 3.6 Hz, H-4a), 2.82 (H, dd, J = 16.4, 11.2 Hz, H-4b), and 1.45 (3H, d, J = 6.3 Hz, H-9); and 13 C-NMR (CD 3 OD, 100 MHz) δ C 170.30 (C-1), 164.99 (C-8), 164.23 (C-6), 142.08 (C-4a), 106.53 (C-5), 100.82 (C-8a), 100.0 (C-7), 75.77 (C-3), 34.13 (C-4), and 19.44 (C-9). Compound 8 was identified as ( R )-6-hydroxymellein [ 32 ].…”

Bioactive Compounds from Terrestrial and Marine-Derived Fungi of the Genus Neosartorya †

“…The previously reported anthraquinones, chrysophanol ( 170 ) and emodin ( 171 ) ( Figure 22 ), were isolated from a culture extract of the marine-derived N. fischeri 1008F1 [ 55 ]. The previously reported acetylquestinol ( 172 ) was isolated as a 1:3 mixture with the undescribed acetylpenipurdin A (173 ), together with the previously reported penipurdin A (174 ) ( Figure 22 ), from a culture extract of the marine sponge-associated N. spinosa KUFA1047 [ 58 ].…”

“…Isochromanones have been reported from both terrestrial and marine-derived Neosartorya species. ( R )-6-Hydroxymellein ( 163 ) ( Figure 21 ) was reported from a culture extract of the algicolous fungus N. takakii KUFC 7898 [ 29 ], as well as from a solid rice culture extract of the marine sponge-associated N. spinosa KUFA 1047 [ 58 ]. The undescribed quadricinctone C ( 164 ) ( Figure 21 ) was isolated from a culture extract of the marine sponge-associated fungus N. quadricincta KUFA0081.…”

“…The previously described diorcinol ( 181 ) ( Figure 24 ) was isolated from a culture extract of the soil-derived N. hiratsukae [ 39 ]. The previously reported tenellic acid ( 182 ), the undescribed neospinosic acid ( 183 ) and spinolactone ( 184 ), and the previously reported vermixocin A ( 185 ) ( Figure 24 ) were isolated from a culture extract of the marine sponge-associated N. spinosa KUFA 1047 [ 58 ]. Since the absolute configuration at C-8 in 182 had not been established, de Sá et al [ 58 ] determined the absolute configuration of C-8 in 182 as 8 S by the comparison of its calculated and experimental ECD spectra.…”

The Discovery of Actinospene, a New Polyene Macrolide with Broad Activity against Plant Fungal Pathogens and Pathogenic Yeasts

“…Thus, the 2S, 3R, 4S, 5R, 7S, 10S, 11R, 12R, 13S, 15S, 24S, and 25S were assigned to 1. A similar approach has been applied for stereo configuration determination of several recently published compounds [37][38][39].…”