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Naphthohydroquinones, naphthoquinones, anthraquinones, and a naphthohydroquinone dimer isolated from the aerial parts of Morinda parvifolia and their cytotoxic effects through up-regulation of p53.
Phytochemistry. 2016 Oct; 130:144-51.P

Abstract

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.

Authors+Show Affiliations

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.School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 100102, PR China. Electronic address: hori2on@126.com.School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 100102, PR China. Electronic address: gaozengping0812@163.com.Department of Cell and Molecular Biology, Research Institute of Orthopedics & Traumatology, Foshan Hospital of TCM, Foshan 528000, PR China. Electronic address: jianzhang@hotmail.com.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.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.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.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27298278

Citation

Kang, Jie, et al. "Naphthohydroquinones, Naphthoquinones, Anthraquinones, and a Naphthohydroquinone Dimer Isolated From the Aerial Parts of Morinda Parvifolia and Their Cytotoxic Effects Through Up-regulation of P53." Phytochemistry, vol. 130, 2016, pp. 144-51.
Kang J, Zhang P, Gao Z, et al. Naphthohydroquinones, naphthoquinones, anthraquinones, and a naphthohydroquinone dimer isolated from the aerial parts of Morinda parvifolia and their cytotoxic effects through up-regulation of p53. Phytochemistry. 2016;130:144-51.
Kang, J., Zhang, P., Gao, Z., Zhang, J., Yan, Z., Wang, H., & Chen, R. (2016). Naphthohydroquinones, naphthoquinones, anthraquinones, and a naphthohydroquinone dimer isolated from the aerial parts of Morinda parvifolia and their cytotoxic effects through up-regulation of p53. Phytochemistry, 130, 144-51. https://doi.org/10.1016/j.phytochem.2016.04.001
Kang J, et al. Naphthohydroquinones, Naphthoquinones, Anthraquinones, and a Naphthohydroquinone Dimer Isolated From the Aerial Parts of Morinda Parvifolia and Their Cytotoxic Effects Through Up-regulation of P53. Phytochemistry. 2016;130:144-51. PubMed PMID: 27298278.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Naphthohydroquinones, naphthoquinones, anthraquinones, and a naphthohydroquinone dimer isolated from the aerial parts of Morinda parvifolia and their cytotoxic effects through up-regulation of p53. AU - Kang,Jie, AU - Zhang,Peng, AU - Gao,Zengping, AU - Zhang,Jian, AU - Yan,Zheng, AU - Wang,Hongqing, AU - Chen,Ruoyun, Y1 - 2016/06/10/ PY - 2015/12/08/received PY - 2016/03/29/revised PY - 2016/04/06/accepted PY - 2016/6/15/entrez PY - 2016/6/15/pubmed PY - 2017/2/25/medline KW - Anthraquinone KW - Cytotoxicity KW - Morinda parvifolia KW - Naphthohydroquinone KW - Naphthohydroquinone dimer KW - Naphthoquinone KW - Rubiaceae KW - p53 SP - 144 EP - 51 JF - Phytochemistry JO - Phytochemistry VL - 130 N2 - 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. SN - 1873-3700 UR - https://www.unboundmedicine.com/medline/citation/27298278/Naphthohydroquinones_naphthoquinones_anthraquinones_and_a_naphthohydroquinone_dimer_isolated_from_the_aerial_parts_of_Morinda_parvifolia_and_their_cytotoxic_effects_through_up_regulation_of_p53_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(16)30065-6 DB - PRIME DP - Unbound Medicine ER -