Pulchinenoside A_qt (BioDeep_00000860961)
Main id: BioDeep_00000230308
PANOMIX_OTCML-2023 Antitumor activity
代谢物信息卡片
化学式: C30H48O4 (472.3552408)
中文名称: 23-羟基白桦酸
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)CO)O)C)C(=O)O
InChI: InChI=1S/C30H48O4/c1-18(2)19-9-14-30(25(33)34)16-15-28(5)20(24(19)30)7-8-22-26(3)12-11-23(32)27(4,17-31)21(26)10-13-29(22,28)6/h19-24,31-32H,1,7-17H2,2-6H3,(H,33,34)/t19-,20+,21+,22+,23-,24+,26-,27-,28+,29+,30-/m0/s1
描述信息
23-hydroxybetulinic acid is one of the bioactive components responsible for its anticancer activity. In vitro: 23-hydroxybetulinic acid also shows different proliferation inhibitory activity against B16, HeLa, and HUVEC, with the IC50 value of 78.5, 80, and 94.8 uM, respectively. 23-hydroxybetulinic acid can promote cell cycle arrest at S phase and induce apoptosis via intrinsic pathway. 23-hydroxybetulinic acid disrupts mitochondrial membrane potential significantly (p<0.01) and selectively downregulates the levels of Bcl-2, survivin and upregulates Bax, cytochrome C, cleaved caspase-9 23-hydroxybetulinic acid can induce apoptosis in K562 cells. [1] 23-hydroxybetulinic acid enhances sensitivity of doxorubicin (DOX, ADR) on MCF-7/ADR cell lines, indicating its potential to be developed as a novel MDR modulator.[2] 23-HBA significantly improve the sensitivity of the tumor to doxorubicin. [3]
23-hydroxybetulinic acid is one of the bioactive components responsible for its anticancer activity. In vitro: 23-hydroxybetulinic acid also shows different proliferation inhibitory activity against B16, HeLa, and HUVEC, with the IC50 value of 78.5, 80, and 94.8 uM, respectively. 23-hydroxybetulinic acid can promote cell cycle arrest at S phase and induce apoptosis via intrinsic pathway. 23-hydroxybetulinic acid disrupts mitochondrial membrane potential significantly (p<0.01) and selectively downregulates the levels of Bcl-2, survivin and upregulates Bax, cytochrome C, cleaved caspase-9 23-hydroxybetulinic acid can induce apoptosis in K562 cells. [1] 23-hydroxybetulinic acid enhances sensitivity of doxorubicin (DOX, ADR) on MCF-7/ADR cell lines, indicating its potential to be developed as a novel MDR modulator.[2] 23-HBA significantly improve the sensitivity of the tumor to doxorubicin. [3]
同义名列表
数据库引用编号
5 个数据库交叉引用编号
- ChEBI: CHEBI:69580
- PubChem: 21672692
- ChEMBL: CHEMBL251308
- CAS: 85999-40-2
- medchemexpress: HY-N0566
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
4 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Mingzhen Xue, Cheng Yang, Wensi Huang, Yifei He, Chen Yang, Yaru Xue, Yuandong Zheng, Xingxing Diao, Xiachang Wang. Pharmacokinetics and metabolite identification of 23-hydroxybetulinic acid in rats by using liquid chromatography-mass spectrometry method.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2024 Feb; 1234(?):124016. doi:
10.1016/j.jchromb.2024.124016. [PMID: 38266610] - Ying Zhou, Jinhua Wen, Guangji Wang. Identification of cytochrome P450 isoenzymes involved in the metabolism of 23-hydroxybetulinic acid in human liver microsomes.
Pharmaceutical biology.
2020 Dec; 58(1):60-63. doi:
10.1080/13880209.2019.1701500. [PMID: 31868554] - Jing-Fang Zhang, Wan-Chao Zhong, Yan-Cheng Li, Yun-Qing Song, Gui-Yang Xia, Gui-Hua Tian, Guang-Bo Ge, Sheng Lin. Bioactivity-Guided Discovery of Human Carboxylesterase Inhibitors from the Roots of Paeonia lactiflora.
Journal of natural products.
2020 10; 83(10):2940-2949. doi:
10.1021/acs.jnatprod.0c00464. [PMID: 32951423] - Nan Yao, Chen-Ran Wang, Ming-Qun Liu, Ying-Jie Li, Wei-Min Chen, Zheng-Qiu Li, Qi Qi, Jin-Jian Lu, Chun-Lin Fan, Min-Feng Chen, Ming Qi, Xiao-Bo Li, Jian Hong, Dong-Mei Zhang, Wen-Cai Ye. Discovery of a novel EGFR ligand DPBA that degrades EGFR and suppresses EGFR-positive NSCLC growth.
Signal transduction and targeted therapy.
2020 10; 5(1):214. doi:
10.1038/s41392-020-00251-2. [PMID: 33033232] - Xiaozhen Guo, Yang Xie, Shan Lian, Zhixiong Li, Yu Gao, Zhou Xu, Pei Hu, Mingcang Chen, Zhaolin Sun, Xiaoting Tian, Chenggang Huang. A sensitive HPLC-MS/MS method for the simultaneous determination of anemoside B4, anemoside A3 and 23-hydroxybetulinic acid: Application to the pharmacokinetics and liver distribution of Pulsatilla chinensis saponins.
Biomedical chromatography : BMC.
2018 Mar; 32(3):. doi:
10.1002/bmc.4124. [PMID: 29078255] - Nan Yao, Ying-Jie Li, Yu-He Lei, Nan Hu, Wei-Min Chen, Zhe Yao, Miao Yu, Jun-Shan Liu, Wen-Cai Ye, Dong-Mei Zhang. A piperazidine derivative of 23-hydroxy betulinic acid induces a mitochondria-derived ROS burst to trigger apoptotic cell death in hepatocellular carcinoma cells.
Journal of experimental & clinical cancer research : CR.
2016 12; 35(1):192. doi:
10.1186/s13046-016-0457-1. [PMID: 27931237] - Fang Zhou, Gang Hao, Jingwei Zhang, Yuanting Zheng, Xiaolan Wu, Kun Hao, Fang Niu, Dan Luo, Yuan Sun, Liang Wu, Wencai Ye, Guangji Wang. Protective effect of 23-hydroxybetulinic acid on doxorubicin-induced cardiotoxicity: a correlation with the inhibition of carbonyl reductase-mediated metabolism.
British journal of pharmacology.
2015 Dec; 172(23):5690-703. doi:
10.1111/bph.12995. [PMID: 25363561] - Ming Liu, Xingzeng Zhao, Lin Xiao, Ge Liu, Haizhou Liu, Xiangyun Wang, Xu Feng, Xiukun Lin. Cytotoxicity of the compounds isolated from Pulsatilla chinensis saponins and apoptosis induced by 23-hydroxybetulinic acid.
Pharmaceutical biology.
2015 Jan; 53(1):1-9. doi:
10.3109/13880209.2014.907323. [PMID: 25026337] - Nan Yao, Ying-Jie Li, Dong-Mei Zhang, Dao-Lu Liu, Ming-Kuen Tang, Anita Yiu, Yong Li, Wei-Min Chen, Ping Lan, Zhe Yao, Zhe-Sheng Chen, Wen-Cai Ye. B4G2 induces mitochondrial apoptosis by the ROS-mediated opening of Ca(2+)-dependent permeability transition pores.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology.
2015; 37(3):838-52. doi:
10.1159/000430212. [PMID: 26382946] - Zhiwen Zhou, Cong Ma, Hengyuan Zhang, Yi Bi, Xia Chen, Hua Tian, Xiaoni Xie, Qingguo Meng, Peter John Lewis, Jinyi Xu. Synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents.
European journal of medicinal chemistry.
2013 Oct; 68(?):444-53. doi:
10.1016/j.ejmech.2013.07.041. [PMID: 23994872] - Dong-Mei Zhang, Ying-Jie Li, Chang Shu, Zhi-Xiong Ruan, Wei-Min Chen, Anita Yiu, Ying-Hui Peng, Jiao Wang, Ping Lan, Zhe Yao, Kwok-Pui Fung, Li-Wu Fu, Zhe-Sheng Chen, Wen-Cai Ye. Bipiperidinyl derivatives of 23-hydroxybetulinic acid reverse resistance of HepG2/ADM and MCF-7/ADR cells.
Anti-cancer drugs.
2013 Jun; 24(5):441-54. doi:
10.1097/cad.0b013e32835fcc77. [PMID: 23466650] - Teresa Mencherini, Patrizia Picerno, Michela Festa, Paola Russo, Anna Capasso, Rita Aquino. Triterpenoid constituents from the roots of Paeonia rockii ssp. rockii.
Journal of natural products.
2011 Oct; 74(10):2116-21. doi:
10.1021/np200359v. [PMID: 21954959] - Ping Lan, Dong-Mei Zhang, Wei-Min Chen, Wen-Cai Ye. [Advances in the study of structural modifications and biological activities of betulinic acids].
Yao xue xue bao = Acta pharmaceutica Sinica.
2010 Nov; 45(11):1339-45. doi:
". [PMID: 21361032] - Yuanting Zheng, Fang Zhou, Xiaolan Wu, Xiaozhou Wen, Yannan Li, Bei Yan, Jingwei Zhang, Gang Hao, Wencai Ye, Guangji Wang. 23-Hydroxybetulinic acid from Pulsatilla chinensis (Bunge) Regel synergizes the antitumor activities of doxorubicin in vitro and in vivo.
Journal of ethnopharmacology.
2010 Apr; 128(3):615-22. doi:
10.1016/j.jep.2010.02.004. [PMID: 20176097] - Hui-nan Zhao, Yong Wang, Wen-kui Su, Xiao-qi Zhang, Wen-cai Ye. [Preparation of 23-hydroxybetulinic acid from the roots of Pulsatilla chinensis].
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials.
2007 Feb; 30(2):170-2. doi:
". [PMID: 17571765] - Min Yang, Guang Ji Wang, Su Jun Wang, Xiao Tian Li, Yu Ping Xu, Song Pei Wang, Jing De Xiang, Shang Ren Pan, Guo Xian Cao, Wen Cai Ye. Quantitative analysis of 23-hydroxybetulinic acid in mouse plasma using electrospray liquid chromatography/mass spectrometry.
Rapid communications in mass spectrometry : RCM.
2005; 19(12):1619-23. doi:
10.1002/rcm.1961. [PMID: 15915449] - Wing-Keung Liu, Joyce C K Ho, Florence W K Cheung, Bonnie P L Liu, Wen-Cai Ye, Chun-Tao Che. Apoptotic activity of betulinic acid derivatives on murine melanoma B16 cell line.
European journal of pharmacology.
2004 Sep; 498(1-3):71-8. doi:
10.1016/j.ejphar.2004.07.103. [PMID: 15363977]