Chemical Constituents of the Deep-Sea-Derived <i>Penicillium citreonigrum</i> MCCC 3A00169 and Their Antiproliferative Effects
Zheng-Biao Zou,
Gang Zhang,
Yu-Qi Zhou,
Chun-Lan Xie,
Ming-Min Xie,
Lin Xu,
You-Jia Hao,
Lian-Zhong Luo,
Xiao-Kun Zhang,
Xian-Wen Yang,
Jun-Song Wang
Affiliations
Zheng-Biao Zou
Center for Molecular Metabolism, School of Environmental and Biological Engineering, Nanjing University of Science and Technology, 200 Xiaolingwei Street, Nanjing 210094, China
Gang Zhang
Xiamen Key Laboratory of Marine Medicinal Natural Products Resources, Xiamen Medica College, 1999 Guankouzhong Road, Xiamen 361023, China
Yu-Qi Zhou
School of Pharmaceutical Sciences, Xiamen University, South Xiangan Road, Xiamen 361102, China
Chun-Lan Xie
Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
Ming-Min Xie
Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
Lin Xu
Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
You-Jia Hao
Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
Lian-Zhong Luo
Xiamen Key Laboratory of Marine Medicinal Natural Products Resources, Xiamen Medica College, 1999 Guankouzhong Road, Xiamen 361023, China
Xiao-Kun Zhang
School of Pharmaceutical Sciences, Xiamen University, South Xiangan Road, Xiamen 361102, China
Xian-Wen Yang
Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
Jun-Song Wang
Center for Molecular Metabolism, School of Environmental and Biological Engineering, Nanjing University of Science and Technology, 200 Xiaolingwei Street, Nanjing 210094, China
Six new citreoviridins (citreoviridins J–O, 1–6) and twenty-two known compounds (7–28) were isolated from the deep-sea-derived Penicillium citreonigrum MCCC 3A00169. The structures of the new compounds were determined by spectroscopic methods, including the HRESIMS, NMR, ECD calculations, and dimolybdenum tetraacetate-induced CD (ICD) experiments. Citreoviridins J−O (1–6) are diastereomers of 6,7-epoxycitreoviridin with different chiral centers at C-2–C-7. Pyrenocine A (7), terrein (14), and citreoviridin (20) significantly induced apoptosis for HeLa cells with IC50 values of 5.4 μM, 11.3 μM, and 0.7 μM, respectively. To be specific, pyrenocine A could induce S phase arrest, while terrein and citreoviridin could obviously induce G0-G1 phase arrest. Citreoviridin could inhibit mTOR activity in HeLa cells.
