TY - JOUR
T1 - Banksialactones and banksiamarins
T2 - isochromanones and isocoumarins from an Australian fungus, Aspergillus banksianus
AU - Chaudhary, Nirmal K.
AU - Pitt, John I.
AU - Lacey, Ernest
AU - Crombie, Andrew
AU - Vuong, Daniel
AU - Piggott, Andrew M.
AU - Karuso, Peter
N1 - Copyright the Publisher 2018. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.
PY - 2018/7/27
Y1 - 2018/7/27
N2 - Chemical investigation of an Australian fungus, Aspergillus banksianus, led to the isolation of the major metabolite banksialactone A (1), eight new isochromanones, banksialactones B-I (2-9), two new isocoumarins, banksiamarins A and B (10 and 11), and the reported compounds, clearanol I (12), dothideomynone A (13), questin (14), and endocrocin (15). The structures of 1-11 were established by NMR spectroscopic data analysis, and the absolute configurations were determined from optical rotations and ECD spectra in conjunction with TD-DFT calculations. The secondary metabolite profile of A. banksianus is unusual, with the 11 most abundant metabolites belonging to a single isochromanone class. Conjugation of 1 with endocrocin, 5-methylorsellinic acid, 3,5-dimethylorsellinic acid, mercaptolactic acid, and an unknown methylthio source gave rise to five unprecedented biosynthetic hybrids, 5-9. The isolated compounds were tested for cytotoxicity, antibacterial, and antifungal activities, with hybrid metabolites 7-9 displaying weak cytotoxic and antibiotic activities.
AB - Chemical investigation of an Australian fungus, Aspergillus banksianus, led to the isolation of the major metabolite banksialactone A (1), eight new isochromanones, banksialactones B-I (2-9), two new isocoumarins, banksiamarins A and B (10 and 11), and the reported compounds, clearanol I (12), dothideomynone A (13), questin (14), and endocrocin (15). The structures of 1-11 were established by NMR spectroscopic data analysis, and the absolute configurations were determined from optical rotations and ECD spectra in conjunction with TD-DFT calculations. The secondary metabolite profile of A. banksianus is unusual, with the 11 most abundant metabolites belonging to a single isochromanone class. Conjugation of 1 with endocrocin, 5-methylorsellinic acid, 3,5-dimethylorsellinic acid, mercaptolactic acid, and an unknown methylthio source gave rise to five unprecedented biosynthetic hybrids, 5-9. The isolated compounds were tested for cytotoxicity, antibacterial, and antifungal activities, with hybrid metabolites 7-9 displaying weak cytotoxic and antibiotic activities.
UR - http://www.scopus.com/inward/record.url?scp=85050748242&partnerID=8YFLogxK
UR - http://purl.org/au-research/grants/arc/DP130103281
UR - http://purl.org/au-research/grants/arc/FT130100142
U2 - 10.1021/acs.jnatprod.7b00816
DO - 10.1021/acs.jnatprod.7b00816
M3 - Article
C2 - 29920099
AN - SCOPUS:85050748242
SN - 0163-3864
VL - 81
SP - 1517
EP - 1526
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 7
ER -