Azaphilone and Diphenyl Ether Derivatives from a Gorgonian-Derived Strain of the Fungus Penicillium pinophilum

Abstract

Three new azaphilone derivatives, pinophilins D-F (1-3), and one new diphenyl ether derivative, hydroxypenicillide (10), together with nine known compounds (4-9, 11-13), were isolated from the gorgonian-derived fungus Penicillium pinophilum XS-20090E18. Their structures including absolute configurations were determined by spectroscopic data, chemical conversions, the ECD exciton chirality method, and ECD calculations. Compounds 10-13 exhibited inhibitory activity against the larval settlement of the barnacle Balanus amphitrite at nontoxic concentrations. Compounds 10 and 11 showed cytotoxicity against Hep-2, RD, and HeLa cell lines.

Recent advances in the chemistry and biology of azaphilones

“…YE3033 26 Colletotrichone A (54) Colletotrichum sp. BS4 37 Antimicrobial (Bacillus subtilis: 0.1 mg mL À1 , Escherichia coli: 1.0 mg mL À1 ) Colletotrichone B (55) Colletotrichum sp. BS4 37 Antimicrobial (Staphylococcus aureus: 5.0 mg mL À1 ) Colletotrichone C (56) Colletotrichum sp.…”

“…52 2.8.2 Mitorubrin derivatives with a 7-benzoyl. The azaphilones with a benzoyl group substituted at C-7 included 12 mitorubrin (107-118), such as 6 00 -hydroxy-(R)-mitorubrinic acid (109), 53 purpurquinone D (110), 53 talarophilones A-B (111-112), 54 pinophilins D-F (113-115), 55 rutilins C-D (116-117) 51 and pinazaphilone A (118). 12 Apart from these, (+)-6 00 -hydroxymitorubrinol acetate (107) and (+)-6 00 -hydroxymitorubrinol (108), were encountered in Hypoxylon rubiginosum, a novel species from northern Thailand.…”

Metabolites from marine invertebrates and their symbiotic microorganisms: molecular diversity discovery, mining, and application

“…Twelve new chromone derivatives, 211-222 (corynechromones A-L) (Fig. 38), were obtained from the spongederived fungus Corynespora cassiicola XS-200900I7 (Zhao et al 2015b). These are the first chromone derivatives reported from the genus Corynespora.…”

“…A possible non-enzymatic cyclization route may be involved to form the epimeric pairs. A Michael reaction can occur with the nucleophile attacking from either face, leading to the formation of the epimeric pairs (Zhao et al 2015b).…”

Bioactive Diphenyl Ethers and Isocoumarin Derivatives from a Gorgonian-Derived Fungus Phoma sp. (TA07-1)

“…has been found to produce many novel and bioactive secondary metabolites such as cytotoxic epoxyphomalin A [5] and phomazine B [6], antifouling (+)-flavipucine [7], and antibacterial phomalevones A–C [8]. During our ongoing investigation for new bioactive compounds from gorgonian-derived fungi in the South China Sea [9,10,11,12,13], the fungal strain Phoma sp. (TA07-1) isolated from gorgonian Dichotella gemmacea attracted our attention, because its EtOAc extract of the fermentation showed significant antibacterial activity towards two Gram-positive bacteria, Staphylococcus albus and S. aureus , and three Gram-negative bacteria Escherichia coli , Vibrio parahaemolyticus , and V. anguillarum.…”