Versixanthones A-F, Cytotoxic Xanthone-Chromanone Dimers from the Marine-Derived Fungus Aspergillus versicolor HDN1009.
Six unusual xanthone-chromanone dimers, versixanthones A-F (1-6), featuring different formal linkages of tetrahydroxanthone and 2,2-disubstituted chroman-4-one monomers, were isolated from a culture of the mangrove-derived fungus Aspergillus versicolor HDN1009. The absolute configurations of 1-6, representing the central and axial chirality elements or preferred helicities, were established by a combination of X-ray diffraction analysis, chemical conversions, and TDDFT-ECD calculations. The interconversion of different biaryl linkages between 1 and 4 and between 2 and 3 in DMSO by a retro-oxa-Michael mechanism provided insight into the formation of the xanthone-chromanone dimers and supported the assignments of their absolute configurations. Compounds 1-6 exhibited cytotoxicities against the seven tested cancer cell lines, with the best IC50 value of 0.7 μM. Compound 5 showed further inhibitory activity against topoisomerase I.
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , 5 Yushan Road, Qingdao, Shandong 266003, People's Republic of China.
Guangwei
G
Wu
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , 5 Yushan Road, Qingdao, Shandong 266003, People's Republic of China.
Guihong
G
Yu
Department of Organic Chemistry, University of Debrecen , POB 20, 4010 Debrecen, Hungary.
Tibor
T
Kurtán
Department of Organic Chemistry, University of Debrecen , POB 20, 4010 Debrecen, Hungary.
Attila
A
Mándi
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , 5 Yushan Road, Qingdao, Shandong 266003, People's Republic of China.
Jixing
J
Peng
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , 5 Yushan Road, Qingdao, Shandong 266003, People's Republic of China.
Xiaomei
X
Mo
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , 5 Yushan Road, Qingdao, Shandong 266003, People's Republic of China.
Ming
M
Liu
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , 5 Yushan Road, Qingdao, Shandong 266003, People's Republic of China.
Hui
H
Li
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , 5 Yushan Road, Qingdao, Shandong 266003, People's Republic of China.
Xinhua
X
Sun
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , 5 Yushan Road, Qingdao, Shandong 266003, People's Republic of China.
Jing
J
Li
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , 5 Yushan Road, Qingdao, Shandong 266003, People's Republic of China.
Tianjiao
T
Zhu
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , 5 Yushan Road, Qingdao, Shandong 266003, People's Republic of China.
Qianqun
Q
Gu
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , 5 Yushan Road, Qingdao, Shandong 266003, People's Republic of China.
Dehai
D
Li
D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001230:Aspergillus / Q000737:chemistry; D002867:Chromones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D008386:Marine Biology; D008968:Molecular Conformation; D015394:Molecular Structure; D043982:Rhizophoraceae / Q000382:microbiology; D059004:Topoisomerase I Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D044004:Xanthones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
D000970:Antineoplastic Agents; D002867:Chromones; D059004:Topoisomerase I Inhibitors; D044004:Xanthones; C000605747:versixanthone E