New Benzofuranoids and Phenylpropanoids from the Mangrove Endophytic Fungus, Aspergillus sp. ZJ-68

Abstract

Three new benzofuranoids, asperfuranoids A–C (1–3), two new phenylpropanoid derivatives (6 and 7), and nine known analogues (4, 5, and 8–14) were isolated from the liquid substrate fermentation cultures of the mangrove endopytic fungus Aspergillus sp. ZJ-68. The structures of the new compounds were determined by extensive spectroscopic data interpretation. The absolute configurations of 1–3 were assigned via the combination of Mosher’s method, and experimental and calculated electronic circular dichroism (ECD) data. Compounds 4 and 5 were a pair of enantiomers and their absolute configurations were established for the first time on the basis of their ECD spectra aided with ECD calculations. All isolated compounds (1–14) were evaluated for their enzyme inhibitory activity against α-glucosidase and antibacterial activities against four pathogenic bacteria (Staphylococcus aureus, Escherichia coli, Bacillus subtilis, and Pseudomonas aeruginosa). Among them, compound 6 exhibited potent inhibitory activity against α-glucosidase in a standard in vitro assay, with an IC50 value of 12.4 μM, while compounds 8 and 11 showed activities against S. aureus, E. coli, and B. subtilis, with MIC values in the range of 4.15 to 12.5 μg/mL.

Antifungal Agents in Agriculture: Friends and Foes of Public Health

“…Endophytic fungi have been studied as an alternative and sustainable means of converting the natural compounds in host plants to antifungal compounds, which are not only effective against human pathogens but also against phytopathogens [127]. Endophytic microorganisms are found in plant species of extreme importance [124] and can be classified as competent, optional, obligatory, opportunistic, or passive, depending on their effects on plants [128][129][130][131]. Recently, they have gained special attention due to the benefits these microorganisms can confer onto their hosts in the form of pesticides, helping the growth and survival of plants and increasing their tolerance to extreme temperatures and drought as well as removing contaminants from the soil [132].…”

Endophytic Fungi as a Source of Antibacterial Compounds—A Focus on Gram-Negative Bacteria

“…Cai and collaborators [ 60 ] isolated two benzofuranoids with antibacterial activity; 2- (hydroxymethyl) -3-propylphenol (16) and (-)—brassicadiol (17) were isolated from the endophytic fungus Aspergillus sp. ZJ-68 found in the leaves of the mangrove plant Kandelia candel collected from the Zhanjiang Mangrove Nature Reserve in Guangdong Province, China.…”

Secondary metabolites from mangrove-associated fungi: source, chemistry and bioactivities

“…There are 26 compounds within this type from mangrove-associated fungi. The Aspergillus strains were the source of the benzofurans, including asperfuranoids A–C ( 256–258 ), 149 asperisocoumarin G ( 259 ), asperisocoumarin H ( 260 ), (±)-asperisocoumarin I ( 261 and 262 ), 150 and ustusoranes A–F ( 263–268 ), 151 of which 267 showed significant cytotoxicity against HL-60 cells with an IC 50 value of 0.13 μM. Two new benzofurans, xyloester A ( 269 ), and xyloallenolide B ( 270 ), were isolated from the mangrove endophytic fungus Xylaria sp.…”

“…317 The Aspergillus strains yielded four new phenol derivatives, including asperphenone C ( 776 ), 258 aspergifuranone 777 , 68 and two new asperpanoids A ( 778 ) and B ( 779 ) with 778 exhibiting inhibitory activity against α-glucosidase with an IC 50 value of 12.4 μM. 149 Four new aromatic allenic ethers 780–783 were isolated from a fungus Xylaria sp. No.…”