Indole-based alkaloids from deep-sea bacterium Shewanella piezotolerans with antitumor activities.
Chromatographic separation of a crude extract obtained from a fermentation broth of a chemically unknown bacterium Shewanella piezotolerans WP3 collected in deep-sea yielded three new indole alkaloids namely shewanellines A (1a), B (1b) and C (2), together with 12 known indole alkaloids. The structures were unambiguously elucidated on the basis of 1D and 2D NMR ((1)H, (13)C, COSY, HMBC, HSQC and NOESY) in association with MS and CD data. Compounds 1-4, 7, 9 and 11-14 were selected for the evaluation of their cytotoxic activities against human tumor cell lines HL-60 and BEL-7402, whereas compounds 2, 4 and 9 exhibited significant inhibition toward HL-60.
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing, PR China.
Yao
Y
Wang
Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, State Oceanic Administration, Xiamen, PR China.
Xixiang
X
Tang
Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, State Oceanic Administration, Xiamen, PR China.
Zhongzhe
Z
Shao
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing, PR China.
Jinwei
J
Ren
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing, PR China.
Dong
D
Liu
Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, Geb.26.23, Düsseldorf, Germany.
Peter
P
Proksch
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing, PR China.
Wenhan
W
Lin
D000470:Alkaloids / Q000302:isolation & purification* / Q000494:pharmacology*; D000903:Antibiotics, Antineoplastic / Q000302:isolation & purification* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D003470:Culture Media; D004354:Drug Screening Assays, Antitumor; D005285:Fermentation; D006801:Humans; D007211:Indoles / Q000302:isolation & purification* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D020592:Shewanella / Q000737:chemistry* / Q000145:classification; D021241:Spectrometry, Mass, Electrospray Ionization
D000470:Alkaloids; D000903:Antibiotics, Antineoplastic; D003470:Culture Media; D007211:Indoles