Columbamine (BioDeep_00000000502)

   

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


2-Hydroxy-3,9,10-trimethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium

化学式: C20H20NO4+ (338.13922600000006)
中文名称: 非洲防己碱
谱图信息: 最多检出来源 Viridiplantae(plant) 0.11%

分子结构信息

SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)O)OC
InChI: InChI=1S/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-17(22)19(24-2)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1

描述信息

Columbamine is a berberine alkaloid and an organic heterotetracyclic compound.
Columbamine is a natural product found in Thalictrum podocarpum, Berberis thunbergii, and other organisms with data available.

同义名列表

19 个代谢物同义名

2-Hydroxy-3,9,10-trimethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium; 5,6-Dihydro-2-hydroxy-3,9,10-trimethoxydibenzo[a,g]quinolizinium iodide; 3,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2-ol; 3,9,10-trimethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium-2-ol; 2-hydroxy-3,9,10-trimethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium; Dibenzo(a,g)quinolizinium, 5,6-dihydro-2-hydroxy-3,9,10-trimethoxy-; Dibenzo[a,g]quinolizinium, 5,6-dihydro-2-hydroxy-3,9,10-trimethoxy-; 7,8,13,13.ALPHA.-TETRADEHYDRO-2-HYDROXY-3,9,10-TRIMETHOXYBERBINIUM; 5,6-dihydro-2-hydroxy-3,9,10-trimethoxydibenzo[a,g]quinolizinium; 5,6-DIHYDRO-2-HYDROXY-3,9,10-TRIMETHOXYDIBENZO(A,G)QUINOLIZINIUM; Columbamin;Dehydroisocorypalmine; YYFOFDHQVIODOQ-UHFFFAOYSA-O; Dehydroisocorypalmine; COLUMBAMINE [MI]; UNII-7T4808FEJW; Columbamine; Columbamin; 7T4808FEJW; Columbamine



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(2)

代谢反应

4 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(3)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

170 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

  • Tan Quang Tu, Phat Tien Do, Doai Van Nguyen, Nhan Thi Thanh Pham, Tam Thi Nguyen, Mau Hoang Chu. The columbamine O-methyltransferase gene (CoOMT) is capable of increasing alkaloid content in transgenic tobacco plants. Molecular biology reports. 2022 Apr; 49(4):2667-2675. doi: 10.1007/s11033-021-07074-6. [PMID: 35059967]
  • Dong-Jun Fu, Jun Li, Bin Yu. Annual review of LSD1/KDM1A inhibitors in 2020. European journal of medicinal chemistry. 2021 Mar; 214(?):113254. doi: 10.1016/j.ejmech.2021.113254. [PMID: 33581557]
  • Renren Bai, Chuansheng Yao, Zhichao Zhong, Jiamin Ge, Ziqiang Bai, Xiangyang Ye, Tian Xie, Yuanyuan Xie. Discovery of natural anti-inflammatory alkaloids: Potential leads for the drug discovery for the treatment of inflammation. European journal of medicinal chemistry. 2021 Mar; 213(?):113165. doi: 10.1016/j.ejmech.2021.113165. [PMID: 33454546]
  • Cheng Tao, Sheng-Quan Hu, Jian Chen, Yuan-Ji Chen, Ke-Huan Sun, Guo-Zhen Cui, Min Ma, Zheng-Zhi Wu. Highly efficient synthesis and monoamine oxidase B inhibitory profile of demethyleneberberine, columbamine and palmatine. Neurochemistry international. 2020 10; 139(?):104807. doi: 10.1016/j.neuint.2020.104807. [PMID: 32711021]
  • Shumin Jiang, Xueli Wu, Yi Wang, Jingtao Zou, Xiaoping Zhao. The potential DPP-4 inhibitors from Xiao-Ke-An improve the glucolipid metabolism via the activation of AKT/GSK-3β pathway. European journal of pharmacology. 2020 Sep; 882(?):173272. doi: 10.1016/j.ejphar.2020.173272. [PMID: 32535096]
  • Zhong-Min Zhao, Xiao-Fei Shang, Raymond Kobla Lawoe, Ying-Qian Liu, Rui Zhou, Yu Sun, Yin-Fang Yan, Jun-Cai Li, Guan-Zhou Yang, Cheng-Jie Yang. Anti-phytopathogenic activity and the possible mechanisms of action of isoquinoline alkaloid sanguinarine. Pesticide biochemistry and physiology. 2019 Sep; 159(?):51-58. doi: 10.1016/j.pestbp.2019.05.015. [PMID: 31400784]
  • Zhenwen Lin, Sheng Li, Peng Guo, Liyang Wang, Lisheng Zheng, Zixing Yan, Xi Chen, Zhuqin Cheng, Haiyi Yan, Cui Zheng, Congkuai Zhao. Columbamine suppresses hepatocellular carcinoma cells through down-regulation of PI3K/AKT, p38 and ERK1/2 MAPK signaling pathways. Life sciences. 2019 Feb; 218(?):197-204. doi: 10.1016/j.lfs.2018.12.038. [PMID: 30582951]
  • Lvhuan Wang, Yumei Zhao, Yanyan Zhang, Tingting Zhang, Jeroen Kool, Govert W Somsen, Qiqin Wang, Zhengjin Jiang. Online screening of acetylcholinesterase inhibitors in natural products using monolith-based immobilized capillary enzyme reactors combined with liquid chromatography-mass spectrometry. Journal of chromatography. A. 2018 Aug; 1563(?):135-143. doi: 10.1016/j.chroma.2018.05.069. [PMID: 29866504]
  • Tian-Jin Wu, Jun Lu, Hui Ni, Ping Li, Yan Jiang, Hui-Jun Li. Construction of an optimized method for quality evaluation and species discrimination of Coptidis Rhizoma by ion-pair high performance liquid chromatography combined with response surface methodology. Journal of pharmaceutical and biomedical analysis. 2018 May; 153(?):152-157. doi: 10.1016/j.jpba.2018.02.019. [PMID: 29494887]
  • Yue Wang, Yulong Han, Fangni Chai, Hongmei Xiang, Tao Huang, Shuming Kou, Bing Han, Xiaobao Gong, Xiaoli Ye. The antihypercholesterolemic effect of columbamine from Rhizoma Coptidis in HFHC-diet induced hamsters through HNF-4α/FTF-mediated CYP7A1 activation. Fitoterapia. 2016 Dec; 115(?):111-121. doi: 10.1016/j.fitote.2016.09.019. [PMID: 27713083]
  • Wenguang Wang, Xiaoli Ma, Xiaoyu Guo, Mingbo Zhao, Pengfei Tu, Yong Jiang. A series of strategies for solving the shortage of reference standards for multi-components determination of traditional Chinese medicine, Mahoniae Caulis as a case. Journal of chromatography. A. 2015 Sep; 1412(?):100-11. doi: 10.1016/j.chroma.2015.08.015. [PMID: 26298606]
  • Mashitah Yusoff, Hazrulrizawati Hamid, Peter Houghton. Anticholinesterase inhibitory activity of quaternary alkaloids from Tinospora crispa. Molecules (Basel, Switzerland). 2014 Jan; 19(1):1201-11. doi: 10.3390/molecules19011201. [PMID: 24448061]
  • 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]
  • Zhao-Tang Ma, Xiu-Wei Yang, Ying Zhang, Jian-Xun Liu. Pharmacochemistry and integrated pharmacokinetics of six alkaloids after oral administration of huang-lian-jie-du-tang decoction. Journal of Asian natural products research. 2014; 16(5):483-96. doi: 10.1080/10286020.2014.913577. [PMID: 24797560]
  • Meimei Bao, Zhifei Cao, Di Yu, Shilong Fu, Gaochuan Zhang, Ping Yang, Yanyan Pan, Bo Yang, Hongyan Han, Quansheng Zhou. Columbamine suppresses the proliferation and neovascularization of metastatic osteosarcoma U2OS cells with low cytotoxicity. Toxicology letters. 2012 Dec; 215(3):174-80. doi: 10.1016/j.toxlet.2012.10.015. [PMID: 23124089]
  • Gang Fan, Meng Ying Zhang, Xiang Dong Zhou, Xian Rong Lai, Qing Hong Yue, Ce Tang, Wei Zao Luo, Yi Zhang. Quality evaluation and species differentiation of Rhizoma coptidis by using proton nuclear magnetic resonance spectroscopy. Analytica chimica acta. 2012 Oct; 747(?):76-83. doi: 10.1016/j.aca.2012.08.038. [PMID: 22986138]
  • Ling Zhu, Bo Huang, Xiaoquan Ban, Jingsheng He, Yuxin Chen, Li Han, Youwei Wang. Coptis chinensis inflorescence extract protection against ultraviolet-B-induced phototoxicity, and HPLC-MS analysis of its chemical composition. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Jul; 50(7):2584-8. doi: 10.1016/j.fct.2012.04.035. [PMID: 22561681]
  • Gang Fan, Ling-hui Tao, Qing-hong Yue, Ting-ting Kuang, Ce Tang, Yong-dong Yang, Wei-zao Luo, Xiang-dong Zhou, Yi Zhang. Metabolic discrimination of rhizoma coptidis from different species using 1H NMR spectroscopy and principal component analysis. Planta medica. 2012 Apr; 78(6):641-8. doi: 10.1055/s-0031-1298240. [PMID: 22314415]
  • Ziming Lu, Wuxing Sun, Xuhong Duan, Zhiyun Yang, Yadong Liu, Pengfei Tu. [Chemical constituents from Corydalis yanhusuo]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Jan; 37(2):235-7. doi: . [PMID: 22737858]
  • Yihui Yang, Ning Kang, Hongjun Xia, Jun Li, Lixia Chen, Feng Qiu. Metabolites of protoberberine alkaloids in human urine following oral administration of Coptidis Rhizoma decoction. Planta medica. 2010 Nov; 76(16):1859-63. doi: 10.1055/s-0030-1250053. [PMID: 20549593]
  • Céline Gasnier, Nora Benachour, Emilie Clair, Carine Travert, Frédéric Langlois, Claire Laurant, Cécile Decroix-Laporte, Gilles-Eric Séralini. Dig1 protects against cell death provoked by glyphosate-based herbicides in human liver cell lines. Journal of occupational medicine and toxicology (London, England). 2010 Oct; 5(?):29. doi: 10.1186/1745-6673-5-29. [PMID: 20979644]
  • Zhipeng Geng, Haijie Zheng, Yi Zhang, Weizao Luo, Xianyou Qu. [Simultaneous determination of six alkaloids in Coptis chinensis of different regions by RP-HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Oct; 35(19):2576-80. doi: ". [PMID: 21174768]
  • Xiaohua Liu, Zhenlin Hu, Qirong Shi, Huawu Zeng, Yunheng Shen, Huizi Jin, Weidong Zhang. Anti-inflammatory and anti-nociceptive activities of compounds from Tinospora sagittata (Oliv.) Gagnep. Archives of pharmacal research. 2010 Jul; 33(7):981-7. doi: 10.1007/s12272-010-0702-7. [PMID: 20661706]
  • Asmah Alias, Hazrina Hazni, Faridahanim Mohd Jaafar, Khalijah Awang, Nor Hadiani Ismail. Alkaloids from Fissistigma latifolium (Dunal) Merr. Molecules (Basel, Switzerland). 2010 Jun; 15(7):4583-8. doi: 10.3390/molecules15074583. [PMID: 20657378]
  • Tomoya Takemura, Nobuhiro Ikezawa, Kinuko Iwasa, Fumihiko Sato. Metabolic diversification of benzylisoquinoline alkaloid biosynthesis through the introduction of a branch pathway in Eschscholzia californica. Plant & cell physiology. 2010 Jun; 51(6):949-59. doi: 10.1093/pcp/pcq063. [PMID: 20427510]
  • Sarita Singh, Tryambak Deo Singh, Virendra Pratap Singh, Vidya Bhushan Pandey. Quaternary alkaloids of Argemone mexicana. Pharmaceutical biology. 2010 Feb; 48(2):158-60. doi: 10.3109/13880200903062622. [PMID: 20645832]
  • Xing-Ye Cheng, Yue Shi, Shun-Liang Zheng, Hong Sun, Wen Jin. [Studies on chemical constituents in the anti-myocardial ischemia effective fraction of Corydalis yanhusuo]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2008 Nov; 31(11):1656-8. doi: . [PMID: 19260272]
  • Zhong-Ze Ma, Wei Xu, Niels H Jensen, Bryan L Roth, Lee-Yuan Liu-Chen, David Y W Lee. Isoquinoline alkaloids isolated from Corydalis yanhusuo and their binding affinities at the dopamine D1 receptor. Molecules (Basel, Switzerland). 2008 Sep; 13(9):2303-12. doi: 10.3390/molecules13092303. [PMID: 18830156]
  • Ya-Ting Deng, Qiong-Feng Liao, Kai-Shun Bi, Mei-Cun Yao, Xiao-fei Jiang, Zhi-Yong Xie. [Analysis of the main components of coptis-evodia herb couple by HPLC-DAD-MS]. Yao xue xue bao = Acta pharmaceutica Sinica. 2008 Mar; 43(3):299-302. doi: ". [PMID: 18630268]
  • Chung-Ren Su, Yune-Fang Ueng, Nguyen Xuan Dung, M Vijaya Bhaskar Reddy, Tian-Shung Wu. Cytochrome P3A4 inhibitors and other constituents of Fibraurea tinctoria. Journal of natural products. 2007 Dec; 70(12):1930-3. doi: 10.1021/np0704248. [PMID: 17994701]
  • Lucia Rackova, Marek Oblozinsky, Daniela Kostalova, Viktor Kettmann, Lydia Bezakova. Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids. Journal of inflammation (London, England). 2007 Jul; 4(?):15. doi: 10.1186/1476-9255-4-15. [PMID: 17634120]
  • Qirong Shi, Shikai Yan, Mingjin Liang, Yun Yang, Yan Wang, Weidong Zhang. Simultaneous determination of eight components in Radix Tinosporae by high-performance liquid chromatography coupled with diode array detector and electrospray tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2007 Feb; 43(3):994-9. doi: 10.1016/j.jpba.2006.09.028. [PMID: 17084577]
  • Yufeng Zhang, Qirong Shi, Peiying Shi, Weidong Zhang, Yiyu Cheng. Characterization of isoquinoline alkaloids, diterpenoids and steroids in the Chinese herb Jin-Guo-Lan (Tinospora sagittata and Tinospora capillipes) by high-performance liquid chromatography/electrospray ionization with multistage mass spectrometry. Rapid communications in mass spectrometry : RCM. 2006; 20(15):2328-42. doi: 10.1002/rcm.2593. [PMID: 16817243]
  • Marjolaine Bourdat-Deschamps, Christine Herrenknecht, Blandine Akendengue, Alain Laurens, Reynald Hocquemiller. Separation of protoberberine quaternary alkaloids from a crude extract of Enantia chlorantha by centrifugal partition chromatography. Journal of chromatography. A. 2004 Jul; 1041(1-2):143-52. doi: 10.1016/j.chroma.2004.04.035. [PMID: 15281263]
  • Esra Küpeli, Müberra Koşar, Erdem Yeşilada, K Hüsnü, C Başer. A comparative study on the anti-inflammatory, antinociceptive and antipyretic effects of isoquinoline alkaloids from the roots of Turkish Berberis species. Life sciences. 2002 Dec; 72(6):645-57. doi: 10.1016/s0024-3205(02)02200-2. [PMID: 12467905]
  • Takashi Morishige, Emilyn Dubouzet, Kum-Boo Choi, Kazufumi Yazaki, Fumihiko Sato. Molecular cloning of columbamine O-methyltransferase from cultured Coptis japonica cells. European journal of biochemistry. 2002 Nov; 269(22):5659-67. doi: 10.1046/j.1432-1033.2002.03275.x. [PMID: 12423366]
  • G T Tan, J M Pezzuto, A D Kinghorn, S H Hughes. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of natural products. 1991 Jan; 54(1):143-54. doi: 10.1021/np50073a012. [PMID: 1710653]
  • Y Ma, Z Zhang, X Tang, R Zhou. [Chemical constituents of Asteropyrum peltatum (Franch.) Drumm. et Hutch]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1990 Dec; 15(12):733-4, 765. doi: ". [PMID: 2282171]
  • P Virtanen, V Lassila, T Njimi, D E Mengata. Natural protoberberine alkaloids from Enantia chlorantha, palmatine, columbamine and jatrorrhizine for thioacetamide-traumatized rat liver. Acta anatomica. 1988; 131(2):166-70. doi: 10.1159/000146507. [PMID: 3369286]