Naphthohydroquinones, naphthoquinones, anthraquinones, and a naphthohydroquinone dimer isolated from the aerial parts of Morinda parvifolia and their cytotoxic effects through up-regulation of p53.
Five unknown compounds, morindaparvins C-G, consisting of naphthohydroquinones, a naphthoquinone, an anthraquinone, and a naphthohydroquinone dimer, together with three known quinones and seven other known compounds, were isolated from the aerial parts of Morinda parvifolia. The structures of morindaparvins C, D, E, F, and G were elucidated on the basis of spectroscopic or X-ray diffraction analysis as methyl 4-hydroxy-1,6-dimethoxy-naphthalene-2-carboxylate, methyl 4,8-dihydroxy-1-methoxy-naphthalene-2-carboxylate, 3-amino-6-methoxy-2-methoxycarbonyl-1,4-naphthoquinone, 1,4-dihydroxy-7-hydroxymethyl-anthraquinone, and dimethyl 1,1'-dihydroxy-4,4',7,7'-tetramethoxy-2,2'-binaphthalene-3,3'-dicarboxylate, respectively. Naphthoquinones and naphthohydroquinone dimers were previously unknown in the genus Morinda. In addition, the compounds were tested for cytotoxicity against four human cancer cell lines HeLa, A2780, Ketr3 and MCF-7 and their effects on p53-activated transcription. Three naphthoquinones had moderate cytotoxic effects with IC50 values ranging from 1.51 to 9.56 μM, through up-regulation of p53 transcriptional activity.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, No. 1 Xiannongtan Street, Beijing 100050, PR China. Electronic address: jiekang@imm.ac.cn.
Jie
J
Kang
School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 100102, PR China. Electronic address: hori2on@126.com.
Peng
P
Zhang
School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 100102, PR China. Electronic address: gaozengping0812@163.com.
Zengping
Z
Gao
Department of Cell and Molecular Biology, Research Institute of Orthopedics & Traumatology, Foshan Hospital of TCM, Foshan 528000, PR China. Electronic address: jianzhang@hotmail.com.
Jian
J
Zhang
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, No. 1 Xiannongtan Street, Beijing 100050, PR China. Electronic address: yanzheng@imm.ac.cn.
Zheng
Z
Yan
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, No. 1 Xiannongtan Street, Beijing 100050, PR China. Electronic address: wanghongqing@imm.ac.cn.
Hongqing
H
Wang
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, No. 1 Xiannongtan Street, Beijing 100050, PR China. Electronic address: rych@imm.ac.cn.
Ruoyun
R
Chen
D000880:Anthraquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D008297:Male; D008968:Molecular Conformation; D015394:Molecular Structure; D032066:Morinda / Q000737:chemistry*; D009285:Naphthoquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D035261:Plant Components, Aerial / Q000737:chemistry*
D000880:Anthraquinones; D000972:Antineoplastic Agents, Phytogenic; D009285:Naphthoquinones; C042834:9,10-anthraquinone; C035342:1,4-naphthoquinone
Anthraquinone; Cytotoxicity; Morinda parvifolia; Naphthohydroquinone; Naphthohydroquinone dimer; Naphthoquinone; Rubiaceae; p53