Sesquiterpene and Xanthone Derivatives from the Sea Fan-Derived Fungus Aspergillus sydowii PSU-F154

Abstract

Three new sesquiterpenes, named aspergillusenes A and B and (+)-(7S)-7-O-methylsydonic acid, and two new hydrogenated xanthone derivatives, named aspergillusones A and B, were isolated from the sea fan-derived fungus Aspergillus sydowii PSU-F154 together with 10 known compounds. Their structures were identified on the basis of spectroscopic data. The isolated compounds were evaluated for their antioxidant activity.

Antibacterial and anti-phytopathogenic substances from the insect pathogenic fungus Gibellula sp. BCC36964

“…The spectroscopic evidence indicated that the hydroxyl group at C-7 in 5 was replaced by a methoxyl group. Therefore, compound 1 was 7-O-methylsydonic acid, which was earlier found from Aspergillus sydowii PSU-F154 in ''S'' form ([a] D + 2, MeOH) (Trisuwan et al, 2011). Their 1 H and 13 C NMR spectral data were similar to those reported in the literature.…”

“…The double bond configurations of compounds 7 and 8 were assigned as E based on the NOEDIFF experiments, which showed a signal enhancement at H 2 -9 when H 3 -14 was irradiated. Moreover, the chemical shifts at C-14 in compounds 7 and 8 were resonated at higher field (d C 17.9 and 17.5, respectively) (Trisuwan et al, 2011;Wei et al, 2010), compared to that of Z-configuration. Compounds in adequate amount (except compounds 2, 7, and 14) were subjected to biological tests for antibacterial (against B. cereus), anti-phytopathogenic (against A. brassicicola, C. capsici, and C. gloeosporioides), and anti-HSV-1 activities.…”

“…The dibenzo[1,4]dioxin was earlier found from a sponge-associated fungus Aspergillus versicolor HMp-48 and showed cell growthinhibition activity against HL-60 cells at IG 50 3.62 mM (Wang et al, 2014). 1 H and 13 C NMR spectral data of compounds 5-17, including (À)-sydonic acid (5), (À)-hydroxysydonic acid (6), aspergillusene A (7), 7-deoxy-7,8-didehydrosydonic acid (8), (À)-sydowic acid (9), sydowinin A (10), methyl 8-hydoxy-6-methyl-9-oxo-9H-xanthone-1-carboxalate (11), fischexanthone (12), moniliphenone (13), AGI-B4 (14), versimide (15), sydowiol C (16), diorcinol (17), and orcinol, were compared to those reported in the literatures (Brown, 1970;Hamasaki et al, 1975Hamasaki et al, , 1978Itabashi et al, 1993;Kachi and Sassa, 1986;Kim et al, 2002;Kudo et al, 2009;Li et al, 2012;Liu et al, 2013;Lö sgen et al, 2008;Tan et al, 2012;Trisuwan et al, 2011;Wang et al, 2010;Wei et al, 2010). The double bond configurations of compounds 7 and 8 were assigned as E based on the NOEDIFF experiments, which showed a signal enhancement at H 2 -9 when H 3 -14 was irradiated.…”

“…Both forms of sydonic acid showed antibacterial activity against various bacteria such as Staphylococcus spp., Bacillus spp., Vibrio anguillarum, Sarcina lutea, Escherichia coli, Micrococcus tetragenus Wei et al, 2010). Hydroxysydonic acid and aspergillusene A (7) were reported from A. sydowii (Hamasaki et al, 1978) and A. sydowii PSU-F154, respectively (Trisuwan et al, 2011). 7-Deoxy-7,8-didehydrosydonic acid and (+)-sydowic acid were isolated from a marine-derived fungus Aspergillus sp.…”

Oximoaspergillimide, a Fungal Derivative from a Marine Isolate of Aspergillus sp.

“…[11,12] However, they have recently gained prominence since isolates from coral-associated fungus Aspergillus are becoming an increasing source of structurally intriguing compounds. [13][14][15][16] As part of our ongoing investigation into cultivable marine microorganisms, fungi have attracted our attention due gillus. The structure of 1 was determined by interpretation of NMR spectroscopic data, and confirmed by synthesis.…”