Isolation and Absolute Stereochemistry of Optically Active Sydonic Acid fromGloniumsp. (Hysteriales, Ascomycota)

Abstract

Optically active sydonic acid (1) was isolated for the first time from a culture broth of Glonium sp. The absolute stereochemistry was established to be (S) by comparing the circular dichroism (CD) spectrum with that of (+)-curcutetraol after conversion into (+)-sydonol (2).

Antibacterial Bisabolane-Type Sesquiterpenoids from the Sponge-Derived Fungus Aspergillus sp.

“…Sydonic acid was isolated from the fungus A. sydowi in 1978 as a racemate [16], while (+)-sydonic acid ([α] 25 D +2.73 ( c 2.30, MeOH)) was isolated from Glonium sp. in 2009 [17]. However, in our case, the optical rotation values of 2 and 3 were [α] 25 D −3.6 ( c 3.70, CHCl 3 ) and [α] 25 D −2.0 ( c 1.03, CHCl 3 ), respectively.…”

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

“…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.…”

“…(+)-Sydonic acid was isolated from several fungus including Glonium sp. (Kudo et al, 2009), Aspergillus sp. (Wei et al, 2010), and Penicillium expansum (Lu et al, 2010), whilst (À)-sydonic acid (5) was recently isolated from the sponge-derived Aspergillus sp.…”

Five Sesquiterpenoids from a Marine-Derived Fungus Aspergillus sp. Isolated from a Gorgonian Dichotella gemmacea

“…The NMR data of 2 closely resembled those of sydonic acid ( 5 ) previously isolated from a terrestrial strain of A. sydowi [11] and a marine fungus Glonium sp. [12]. The only significant differences in the 1 H-NMR spectrum of 2 in comparison with 5 were two signals for H 2 -14 which were shifted downfield to δ H 5.45 and 5.19 (instead of a methyl group at δ H 1.68).…”

“…attracted our attention because of the fact that a crude EtOAc extract of the fungal culture showed pronounced in vitro cytotoxicity against the A-549 human lung carcinoma cell line. Bioassay-guided fractionation of the extract led to the isolation of three new phenolic bisabolane-type sesquiterpenoids: (+)-methyl sydowate ( 1 ), 7-deoxy-7,14-didehydrosydonic acid ( 2 ), and 7-deoxy-7,8-didehydrosydonic acid ( 3 ), together with two known fungal metabolites: (+)-sydowic acid ( 4 ) [9,10], and (+)-sydonic acid ( 5 ) [11,12] (Figure 1). To date, this is the first report of natural products from a marine-derived fungus isolated from the fresh tissues of a gorgonian coral.…”