Chileninone (BioDeep_00000230038)
Secondary id: BioDeep_00000395617
PANOMIX_OTCML-2023
代谢物信息卡片
17-methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-ol;chloride
化学式: C19H16NO4.Cl (357.07678060000006)
中文名称: 小檗红碱, 小檗红碱
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 1.06%
分子结构信息
SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)O.[Cl-]
InChI: 1H
描述信息
Berberrubine is an alkaloid.
Berberrubine chloride is an active metabolite of berberine, attenuates ulcerative colitis in mice model[1].
Berberrubine chloride is an active metabolite of berberine, attenuates ulcerative colitis in mice model[1].
同义名列表
20 个代谢物同义名
17-methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-ol;chloride; 9-Hydroxy-10-methoxy-5,6-dihydro-[1,3]dioxolo-[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride; 9-hydroxy-10-methoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride; Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9-hydroxy-10-methoxy-, chloride; Berbinium, 7,8,13,13a-tetradehydro-9-hydroxy-10-methoxy-2,3-(methylenedioxy)-, chloride; 5,6-dihydro-9-hydroxy-10-methoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride; Berbinium,8,13,13a-tetradehydro-9-hydroxy-10-methoxy-2,3-(methylenedioxy)-, chloride; Benzo[g]-1,6-a]quinolizium, 5,6-dihydro-9-hydroxy-10-methoxy-, chloride,; Berberrubine chloride pound>>Beroline chloride; doi:10.14272/GYFSYEVKFOOLFZ-UHFFFAOYSA-N.1; 10.14272/GYFSYEVKFOOLFZ-UHFFFAOYSA-N.1; Berberrubine hydrochloride; BERBERRUBINE, DIHYDRATE; Berberrubine (chloride); 9-berberoline chloride; Berberrubine chloride; Beberrubine Chloride; Beroline chloride; Berberrubine; Chileninone
数据库引用编号
7 个数据库交叉引用编号
- ChEBI: CHEBI:175111
- PubChem: 72703
- ChEMBL: CHEMBL1223099
- MeSH: berberrubine
- ChemIDplus: 0015401691
- CAS: 15401-69-1
- medchemexpress: HY-125850
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)
1 个相关的物种来源信息
- 33090 Plants: -
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
- Jinqiu Rao, Qing Gao, Na Li, Yuan Wang, Tianwang Wang, Kai Wang, Feng Qiu. Unraveling the enigma: Molecular mechanisms of berberrubine-induced nephrotoxicity reversed by its parent form berberine.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2024 Jul; 129(?):155648. doi:
10.1016/j.phymed.2024.155648. [PMID: 38669970] - Xiangli He, Jiayan Cui, Hui Ma, Naijipu Abuduaini, Ying Huang, Lu Tang, Wanyan Wang, Yuanyuan Zhang, Yang Wang, Weiqiang Lu, Bo Feng, Jin Huang. Berberrubine is a novel and selective IMPDH2 inhibitor that impairs the growth of colorectal cancer.
Biochemical pharmacology.
2023 Oct; 218(?):115868. doi:
10.1016/j.bcp.2023.115868. [PMID: 37871880] - Lei Yu, Luyao Sun, Qian Yu, Fang Xiong, Daibo Wang, Lin Pu, Fu Peng, Xiaofang Xie, Cheng Peng. Bioactive compounds and mechanism of Xianglian pill in the treatment of gastric cancer: Network pharmacology analysis and experimental validation.
Journal of ethnopharmacology.
2023 May; ?(?):116573. doi:
10.1016/j.jep.2023.116573. [PMID: 37142148] - Guoshu Lin, Qiuxia Yu, Lieqiang Xu, Ziwei Huang, Liting Mai, Linyun Jiang, Ziren Su, Jianhui Xie, Yucui Li, Yuhong Liu, Zhixiu Lin, Jiannan Chen. Berberrubine attenuates potassium oxonate- and hypoxanthine-induced hyperuricemia by regulating urate transporters and JAK2/STAT3 signaling pathway.
European journal of pharmacology.
2021 Dec; 912(?):174592. doi:
10.1016/j.ejphar.2021.174592. [PMID: 34699754] - Xiao-Wei Hu, Mei-Hui Zhang, Jia-Yi Cheng, Ruo-Jun Man, Dong-Dong Li. A berberrubine-derived fluorescent probe for hydrazine and its practical application in water and food samples.
Analytica chimica acta.
2021 Aug; 1172(?):338504. doi:
10.1016/j.aca.2021.338504. [PMID: 34119017] - Runbin Sun, Bo Kong, Na Yang, Bei Cao, Dong Feng, Xiaoyi Yu, Chun Ge, Siqi Feng, Fei Fei, Jingqiu Huang, Zhenyao Lu, Yuan Xie, Chung S Yang, Grace L Guo, Guangji Wang, Jiye Aa. The Hypoglycemic Effect of Berberine and Berberrubine Involves Modulation of Intestinal Farnesoid X Receptor Signaling Pathway and Inhibition of Hepatic Gluconeogenesis.
Drug metabolism and disposition: the biological fate of chemicals.
2021 03; 49(3):276-286. doi:
10.1124/dmd.120.000215. [PMID: 33376148] - Hongmei Lin, Longfei Lin, Yoonsun Choi, Bozena Michniak-Kohn. Development and in-vitro evaluation of co-loaded berberine chloride and evodiamine ethosomes for treatment of melanoma.
International journal of pharmaceutics.
2020 May; 581(?):119278. doi:
10.1016/j.ijpharm.2020.119278. [PMID: 32229284] - Xiufang Liang, Yunan Xiang, Yanling Li, Ping Feng, Yongping Qin, Xianrong Lai. A rapid method for simultaneous quantification of berberine, berbamine, magnoflorine and berberrubine in mouse serum using UPLC-MS/MS.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2020 Apr; 1142(?):122040. doi:
10.1016/j.jchromb.2020.122040. [PMID: 32145638] - Kai Wang, Jinqiu Rao, Tingting Zhang, Qing Gao, Jichao Zhang, Chenxi Guang, Liqin Ding, Feng Qiu. Metabolic Activation and Covalent Protein Binding of Berberrubine: Insight into the Underlying Mechanism Related to Its Hepatotoxicity.
Drug design, development and therapy.
2020; 14(?):4423-4438. doi:
10.2147/dddt.s274627. [PMID: 33122887] - Emanuele Porru, Placido Franco, Donato Calabria, Silvia Spinozzi, Marinella Roberti, Cristiana Caliceti, Aldo Roda. Combined analytical approaches to define biodistribution and biological activity of semi-synthetic berberrubine, the active metabolite of natural berberine.
Analytical and bioanalytical chemistry.
2018 Jun; 410(15):3533-3545. doi:
10.1007/s00216-018-0884-2. [PMID: 29411090] - Na Yang, Sijia Li, Caixia Yan, Runbin Sun, Jun He, Yuan Xie, Ying Peng, Guangji Wang, Jiye Aa. Inhibitory Effects of Endogenous Linoleic Acid and Glutaric Acid on the Renal Glucuronidation of Berberrubine in Mice and on Recombinant Human UGT1A7, 1A8, and 1A9.
Molecular pharmacology.
2018 03; 93(3):216-227. doi:
10.1124/mol.117.110668. [PMID: 29351921] - Xiu-Ting Yu, Yi-Fei Xu, Yan-Feng Huang, Chang Qu, Lie-Qiang Xu, Zi-Ren Su, Hui-Fang Zeng, Lin Zheng, Tie-Gang Yi, Hui-Lin Li, Jian-Ping Chen, Xiao-Jun Zhang. Berberrubine attenuates mucosal lesions and inflammation in dextran sodium sulfate-induced colitis in mice.
PloS one.
2018; 13(3):e0194069. doi:
10.1371/journal.pone.0194069. [PMID: 29538417] - Kun Wang, Miao Qiao, Liwei Chai, Shijie Cao, Xinchi Feng, Liqin Ding, Feng Qiu. Identification of berberrubine metabolites in rats by using ultra-high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry.
Fitoterapia.
2018 Jan; 124(?):23-33. doi:
10.1016/j.fitote.2017.10.005. [PMID: 28993283] - Govindasami Chandirasegaran, Chakkaravarthy Elanchezhiyan, Kavisa Ghosh, Subramaniam Sethupathy. Berberine chloride ameliorates oxidative stress, inflammation and apoptosis in the pancreas of Streptozotocin induced diabetic rats.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2017 Nov; 95(?):175-185. doi:
10.1016/j.biopha.2017.08.040. [PMID: 28843149] - Na Yang, Run-Bin Sun, Xing-Long Chen, Le Zhen, Chun Ge, Yu-Qing Zhao, Jun He, Jian-Liang Geng, Jia-Hua Guo, Xiao-Yi Yu, Fei Fei, Si-Qi Feng, Xuan-Xuan Zhu, Hong-Bo Wang, Feng-Hua Fu, Ji-Ye Aa, Guang-Ji Wang. In vitro assessment of the glucose-lowering effects of berberrubine-9-O-β-D-glucuronide, an active metabolite of berberrubine.
Acta pharmacologica Sinica.
2017 Mar; 38(3):351-361. doi:
10.1038/aps.2016.120. [PMID: 28042874] - Na Yang, Runbin Sun, Yuqing Zhao, Jun He, Le Zhen, Jiahua Guo, Jianliang Geng, Yuan Xie, Jiankun Wang, Siqi Feng, Fei Fei, Xiaoying Liao, Xuanxuan Zhu, Hongbo Wang, Fenghua Fu, Jiye Aa, Guangji Wang. High fat diet aggravates the nephrotoxicity of berberrubine by influencing on its pharmacokinetic profile.
Environmental toxicology and pharmacology.
2016 Sep; 46(?):319-327. doi:
10.1016/j.etap.2016.08.003. [PMID: 27525563] - Liping Li, Siyuan Sun, Yayun Weng, Feifeng Song, Sisi Zhou, Mengru Bai, Hui Zhou, Su Zeng, Huidi Jiang. Interaction of six protoberberine alkaloids with human organic cation transporters 1, 2 and 3.
Xenobiotica; the fate of foreign compounds in biological systems.
2016; 46(2):175-83. doi:
10.3109/00498254.2015.1056283. [PMID: 26134304] - Xianqin Wang, Shuanghu Wang, Jianshe Ma, Tao Ye, Mengrou Lu, Miao Fan, Mingjie Deng, Lufeng Hu, Zhimou Gao. Pharmacokinetics in rats and tissue distribution in mouse of berberrubine by UPLC-MS/MS.
Journal of pharmaceutical and biomedical analysis.
2015 Nov; 115(?):368-74. doi:
10.1016/j.jpba.2015.07.031. [PMID: 26279368] - Shi-Tang Ma, Cheng-Tao Feng, Guo-Liang Dai, Yue Song, Guo-Liang Zhou, Xiao-Lin Zhang, Cheng-Gui Miao, Hao Yu, Wen-Zheng Ju. In silico target fishing for the potential bioactive components contained in Huanglian Jiedu Tang (HLJDD) and elucidating molecular mechanisms for the treatment of sepsis.
Chinese journal of natural medicines.
2015 Jan; 13(1):30-40. doi:
10.1016/s1875-5364(15)60004-8. [PMID: 25660286] - Veerachai Pongkittiphan, Warinthorn Chavasiri, Roongtawan Supabphol. Antioxidant Effect of Berberine and its Phenolic Derivatives Against Human Fibrosarcoma Cells.
Asian Pacific journal of cancer prevention : APJCP.
2015; 16(13):5371-6. doi:
10.7314/apjcp.2015.16.13.5371. [PMID: 26225680] - Silvia Spinozzi, Carolina Colliva, Cecilia Camborata, Marinella Roberti, Cristina Ianni, Flavia Neri, Claudio Calvarese, Andrea Lisotti, Giuseppe Mazzella, Aldo Roda. Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
Journal of natural products.
2014 Apr; 77(4):766-72. doi:
10.1021/np400607k. [PMID: 24593257] - Yan Zhou, Shijie Cao, Ying Wang, Peixiang Xu, Jiankun Yan, Wen Bin, Feng Qiu, Ning Kang. Berberine metabolites could induce low density lipoprotein receptor up-regulation to exert lipid-lowering effects in human hepatoma cells.
Fitoterapia.
2014 Jan; 92(?):230-7. doi:
10.1016/j.fitote.2013.11.010. [PMID: 24321576] - Mei Zhong, Yu-Xi Ma, Jun-Xi Liu, Duo-Long Di. A new quaternary protoberberine alkaloid isolated from Dicranostigma leptopodum (Maxim) Fedde.
Natural product research.
2014; 28(8):507-10. doi:
10.1080/14786419.2013.879586. [PMID: 24499388] - Jing-Yi Ma, Ru Feng, Xiang-Shan Tan, Chao Ma, Jia-Wen Shou, Jie Fu, Min Huang, Chi-Yu He, Shuo-Nan Chen, Zhen-Xiong Zhao, Wen-Yi He, Yan Wang, Jian-Dong Jiang. Excretion of berberine and its metabolites in oral administration in rats.
Journal of pharmaceutical sciences.
2013 Nov; 102(11):4181-92. doi:
10.1002/jps.23718. [PMID: 24006193] - Xiang-Shan Tan, Jing-Yi Ma, Ru Feng, Chao Ma, Wen-Jing Chen, Yu-Peng Sun, Jie Fu, Min Huang, Chi-Yu He, Jia-Wen Shou, Wen-Yi He, Yan Wang, Jian-Dong Jiang. Tissue distribution of berberine and its metabolites after oral administration in rats.
PloS one.
2013; 8(10):e77969. doi:
10.1371/journal.pone.0077969. [PMID: 24205048] - June K Dunnick, Bhanu Singh, Abraham Nyska, John Peckham, Grace E Kissling, J Michael Sanders. Investigating the potential for toxicity from long-term use of the herbal products, goldenseal and milk thistle.
Toxicologic pathology.
2011 Feb; 39(2):398-409. doi:
10.1177/0192623310394211. [PMID: 21300790] - Ying-Hong Li, Yi Li, Peng Yang, Wei-Jia Kong, Xue-Fu You, Gang Ren, Hong-Bin Deng, Yue-Ming Wang, Yan-Xiang Wang, Jian-Dong Jiang, Dan-Qing Song. Design, synthesis, and cholesterol-lowering efficacy for prodrugs of berberrubine.
Bioorganic & medicinal chemistry.
2010 Sep; 18(17):6422-8. doi:
10.1016/j.bmc.2010.06.106. [PMID: 20673726] - R N Jha, M B Pandey, A K Singh, S Singh, V P Singh. New alkaloids from Corydalis species.
Natural product research.
2009; 23(3):250-5. doi:
10.1080/14786410801996390. [PMID: 19235025] - Feng Zuo, Norio Nakamura, Teruaki Akao, Masao Hattori. Pharmacokinetics of berberine and its main metabolites in conventional and pseudo germ-free rats determined by liquid chromatography/ion trap mass spectrometry.
Drug metabolism and disposition: the biological fate of chemicals.
2006 Dec; 34(12):2064-72. doi:
10.1124/dmd.106.011361. [PMID: 16956957] - Sung Han Kim, Sang Jun Lee, Joo Hyoung Lee, Won Suck Sun, Jung Han Kim. Antimicrobial activity of 9-O-acyl- and 9-O-alkylberberrubine derivatives.
Planta medica.
2002 Mar; 68(3):277-81. doi:
10.1055/s-2002-23128. [PMID: 11914971]