Isolation, Structure elucidation, and antimycobacterial properties of dimeric naphtho-gamma-pyrones from the marine-derived fungus Aspergillus carbonarius.
Two new dimeric naphtho-gamma-pyrones, compounds 1 and 2, were isolated from the AcOEt extract of the fungal strain WZ-4-11 of Aspergillus carbonarius, together with eight known analogues, including 10,10'-bifonsecin B (3), 6'-O-demethylnigerone (4), nigerone (5), isonigerone (6), fonsecin (7), rubrofusarin B (8), TMC 256A1 (9), and flavasperone (10). Their structures were elucidated by means of UV, CD, IR, and 1D- and 2D-NMR spectroscopy, in combination with HR-MS analysis. The fully assigned (1)H- and (13)C-NMR data of 3, and the (13)C-NMR data of 6 are reported for the first time. Compounds 1 and 2 showed weak antimycobacterial activities against Mycobacterium tuberculosis H37Rv, with MIC values of 43.0 and 21.5 microM, resp.
Zhang
Yapeng
Y
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China.
Ling
Sun
S
Fang
Yuchun
Y
Zhu
Tianjiao
T
Gu
Qianqun
Q
Zhu
Wei-Ming
WM
D000995:Antitubercular Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001230:Aspergillus / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D009281:Naphthalenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D011753:Pyrones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D012015:Reference Standards; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D013237:Stereoisomerism
C527652:8'-O-demethylisonigerone; C527651:8'-O-demethylnigerone; D000995:Antitubercular Agents; D009281:Naphthalenes; D011753:Pyrones