Canadine (BioDeep_00000000840)

 

Secondary id: BioDeep_00000017214, BioDeep_00000172059

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(1S)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene

化学式: C20H21NO4 (339.14705060000006)
中文名称: (s)-四氢小檗碱, 四氢小檗碱
谱图信息: 最多检出来源 Viridiplantae(plant) 0.13%

分子结构信息

SMILES: COC1=C(C2=C(CC3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)OC
InChI: InChI=1S/C20H21NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3

描述信息

(S)-canadine is the (S)-enantiomer of canadine. It has a role as a plant metabolite. It is an an (S)-7,8,13,14-tetrahydroprotoberberine and a canadine. It is functionally related to a (S)-nandinine. It is an enantiomer of a (R)-canadine.
(S)-Canadine is a natural product found in Hydrastis canadensis, Corydalis turtschaninovii, and other organisms with data available.
The (S)-enantiomer of canadine.
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.721
D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors
D002317 - Cardiovascular Agents > D002121 - Calcium Channel Blockers
D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents
D000077264 - Calcium-Regulating Hormones and Agents
D049990 - Membrane Transport Modulators
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.718
Tetrahydroberberine is an isoquinoline alkaloid isolated from Corydalis Corydalis, with uM-level affinity for D2 and 5-HT1A receptors.
Tetrahydroberberine is a different kind of living thing that can be extended and divided into parts. Tetrahydroberberine is a kind of effective D2 receptor antagonistic force. Tetrahydroberberine has the ability to strengthen the stomach and relieve the pressure on the stomach[1][2][3].
Tetrahydroberberine is an isoquinoline alkaloid isolated from Corydalis Corydalis, with uM-level affinity for D2 and 5-HT1A receptors.

同义名列表

29 个代谢物同义名

(1S)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene; (13aS)-5, 8, 13, 13a-tetrahydro-9, 10-dimethoxy-6H-benzo[g] -1,3-benzodioxolo[5, 6-a]quinolizine; (13aS)-9,10-dimethoxy-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline; 6H-BENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINE, 5,8,13,13A-TETRAHYDRO-9,10-DIMETHOXY-, (13AS)-; 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (13aS)-; (13aS)-9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline; 6H-Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (S)-; (13aS)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine; 5,6,13,13a-Tetrahydro-9,10-dimethoxy-2,3-(methylenedioxy)-8H-dibenzo(a,g)quinolizine; 9,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-benzo[g][1,3]benzodioxolo[5,6-a]quinolizine; 13a-alpha-BERBINE, 9,10-DIMETHOXY-2,3-(METHYLENEDIOXY)-; Canadine (Tetrahydroberberine); (S)-(-)-Tetrahydroberberine; (-)-Tetrahydroberberine; (S)-Tetrahydroberberine; CANADINE L-FORM [MI]; (S)-(-)-Canadine; .ALPHA.-CANADINE; UNII-Q97V5BUT9D; Canadine l-form; Canadine, (-)-; alpha-canadine; (-)-Canadine; (S)-Canadine; l-Canadine; Q97V5BUT9D; Canadine; Tetrahydroberberine; (13aS)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3- benzodioxolo[5,6-a]quinolizine



数据库引用编号

29 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(1)

代谢反应

13 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(3)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(10)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

37 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

  • Guilan Wei, Ning Huang, Mengyao Li, Fengkun Guan, Liping Chen, Yingyi Liao, Xingyu Xie, Yucui Li, Ziren Su, Jiannan Chen, Yuhong Liu. Tetrahydroberberine alleviates high-fat diet-induced hyperlipidemia in mice via augmenting lipoprotein assembly-induced clearance of low-density lipoprotein and intermediate-density lipoprotein. European journal of pharmacology. 2024 Apr; 968(?):176433. doi: 10.1016/j.ejphar.2024.176433. [PMID: 38369273]
  • Binjun Yan, Zi-Ao Huang, Noorfatimah Yahaya, David Da Yong Chen. Enantioselective analysis in complex matrices using capillary electrophoresis-mass spectrometry: A case study of the botanical drug Corydalis Rhizoma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 Sep; 1152(?):122216. doi: 10.1016/j.jchromb.2020.122216. [PMID: 32531643]
  • Manead Khin, Nadja B Cech, Joshua J Kellogg, Lindsay K Caesar. Chemical Evaluation of the Effects of Storage Conditions on the Botanical Goldenseal using Marker-based and Metabolomics Approaches. The Yale journal of biology and medicine. 2020 06; 93(2):265-275. doi: . [PMID: 32607087]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • 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]
  • Phuong Mai Le, Clément Milande, Estelle Martineau, Patrick Giraudeau, Jonathan Farjon. Quantification of natural products in herbal supplements: A combined NMR approach applied on goldenseal. Journal of pharmaceutical and biomedical analysis. 2019 Feb; 165(?):155-161. doi: 10.1016/j.jpba.2018.11.062. [PMID: 30544050]
  • Bhawani Datt Joshi, Anubha Srivastava, Poonam Tandon, Sudha Jain, A P Ayala. A combined experimental (IR, Raman and UV-Vis) and quantum chemical study of canadine. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2018 Feb; 191(?):249-258. doi: 10.1016/j.saa.2017.10.008. [PMID: 29040931]
  • Dujun Wang, Kai Wang, Danjuan Sui, Zhen Ouyang, Haiyu Xu, Yuan Wei. Effects of tetrahydroberberine and tetrahydropalmatine on hepatic cytochrome P450 expression and their toxicity in mice. Chemico-biological interactions. 2017 Apr; 268(?):47-52. doi: 10.1016/j.cbi.2017.02.019. [PMID: 28257954]
  • Stephanie Galanie, Christina D Smolke. Optimization of yeast-based production of medicinal protoberberine alkaloids. Microbial cell factories. 2015 Sep; 14(?):144. doi: 10.1186/s12934-015-0332-3. [PMID: 26376732]
  • Thu-Thuy T Dang, Xue Chen, Peter J Facchini. Acetylation serves as a protective group in noscapine biosynthesis in opium poppy. Nature chemical biology. 2015 Feb; 11(2):104-6. doi: 10.1038/nchembio.1717. [PMID: 25485687]
  • Ji Won Jung, Yong Sam Kwon, Jin Seok Jeong, Miwon Son, Hee Eun Kang. Pharmacokinetics and brain distribution of tetrahydropalmatine and tetrahydroberberine after oral administration of DA-9701, a new botanical gastroprokinetic agent, in rats. Biological & pharmaceutical bulletin. 2015; 38(2):285-91. doi: 10.1248/bpb.b14-00678. [PMID: 25747988]
  • Jia-jia Yu, Deng-li Cong, Ying Jiang, Yuan Zhou, Yan Wang, Chun-fang Zhao. [Study on alkaloids of Corydalis ochotensis and their antitumor bioactivity]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Oct; 37(10):1795-8. doi: . [PMID: 25895386]
  • Thu-Thuy T Dang, Peter J Facchini. Cloning and characterization of canadine synthase involved in noscapine biosynthesis in opium poppy. FEBS letters. 2014 Jan; 588(1):198-204. doi: 10.1016/j.febslet.2013.11.037. [PMID: 24316226]
  • Hong Liu, Liang Wang, Yan Li, Jiang Liu, Maomao An, Shaolong Zhu, Yongbing Cao, Zhihui Jiang, Mingzhu Zhao, Zhan Cai, Li Dai, Tingjunhong Ni, Wei Liu, Simin Chen, Changqing Wei, Chengxu Zang, Shujuan Tian, Jingyu Yang, Chunfu Wu, Dazhi Zhang, Hua Liu, Yuanying Jiang. Structural optimization of berberine as a synergist to restore antifungal activity of fluconazole against drug-resistant Candida albicans. ChemMedChem. 2014 Jan; 9(1):207-16. doi: 10.1002/cmdc.201300332. [PMID: 24376206]
  • Nadja B Cech, Hiyas A Junio, Laynez W Ackermann, Jeffrey S Kavanaugh, Alexander R Horswill. Quorum quenching and antimicrobial activity of goldenseal (Hydrastis canadensis) against methicillin-resistant Staphylococcus aureus (MRSA). Planta medica. 2012 Sep; 78(14):1556-61. doi: 10.1055/s-0032-1315042. [PMID: 22814821]
  • Yinying Zhang, Kuan Shi, Jun Wen, Guorong Fan, Yifeng Chai, Zhanying Hong. Chiral HPLC determination and stereoselective pharmacokinetics of tetrahydroberberine enantiomers in rats. Chirality. 2012 Mar; 24(3):239-44. doi: 10.1002/chir.21988. [PMID: 22271601]
  • 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]
  • Mingyong Zhang, Jian Le, Jun Wen, Yifeng Chai, Guorong Fan, Zhanying Hong. Simultaneous determination of tetrahydropalmatine and tetrahydroberberine in rat urine using dispersive liquid-liquid microextraction coupled with high-performance liquid chromatography. Journal of separation science. 2011 Nov; 34(22):3279-86. doi: 10.1002/jssc.201100588. [PMID: 22028314]
  • Yingchun Zhang, Haiyu Xu, Xiaomeng Chen, Chang Chen, Haijun Wang, Fanyun Meng, Hongjun Yang, Luqi Huang. Simultaneous quantification of 17 constituents from Yuanhu Zhitong tablet using rapid resolution liquid chromatography coupled with a triple quadrupole electrospray tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2011 Nov; 56(3):497-504. doi: 10.1016/j.jpba.2011.06.008. [PMID: 21733652]
  • Tae Ho Lee, Ki Hyun Kim, Sung Ok Lee, Kang Ro Lee, Miwon Son, Mirim Jin. Tetrahydroberberine, an isoquinoline alkaloid isolated from corydalis tuber, enhances gastrointestinal motor function. The Journal of pharmacology and experimental therapeutics. 2011 Sep; 338(3):917-24. doi: 10.1124/jpet.111.182048. [PMID: 21659472]
  • Yusei Kashima, Hidehiko Yamaki, Takuya Suzuki, Mitsuo Miyazawa. Insecticidal effect and chemical composition of the volatile oil from Bergenia ligulata. Journal of agricultural and food chemistry. 2011 Jul; 59(13):7114-9. doi: 10.1021/jf201401j. [PMID: 21639116]
  • Keivan A Ettefagh, Johnna T Burns, Hiyas A Junio, Glenn W Kaatz, Nadja B Cech. Goldenseal (Hydrastis canadensis L.) extracts synergistically enhance the antibacterial activity of berberine via efflux pump inhibition. Planta medica. 2011 May; 77(8):835-40. doi: 10.1055/s-0030-1250606. [PMID: 21157683]
  • Jaroslaw M Boberek, Jem Stach, Liam Good. Genetic evidence for inhibition of bacterial division protein FtsZ by berberine. PloS one. 2010 Oct; 5(10):e13745. doi: 10.1371/journal.pone.0013745. [PMID: 21060782]
  • Ki Hyun Kim, Il Kyun Lee, Cheng Jie Piao, Sang Un Choi, Jei Hyun Lee, Yeong Shik Kim, Kang Ro Lee. Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity. Bioorganic & medicinal chemistry letters. 2010 Aug; 20(15):4487-90. doi: 10.1016/j.bmcl.2010.06.035. [PMID: 20594848]
  • Fei Cai, Wen Xu, Hua Wei, Lianna Sun, Shouhong Gao, Qi Yang, Jin Feng, Feng Zhang, Wansheng Chen. Simultaneous determination of active xanthone glycosides, timosaponins and alkaloids in rat plasma after oral administration of Zi-Shen Pill extract for the pharmacokinetic study by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Jul; 878(21):1845-54. doi: 10.1016/j.jchromb.2010.05.024. [PMID: 20541984]
  • Andreas Winkler, Martin Puhl, Hansjörg Weber, Toni M Kutchan, Karl Gruber, Peter Macheroux. Berberine bridge enzyme catalyzes the six electron oxidation of (S)-reticuline to dehydroscoulerine. Phytochemistry. 2009 Jun; 70(9):1092-1097. doi: 10.1016/j.phytochem.2009.06.005. [PMID: 19570558]
  • Gregory M Raner, Sean Cornelious, Kamalika Moulick, Yingqing Wang, Ashley Mortenson, Nadja B Cech. Effects of herbal products and their constituents on human cytochrome P450(2E1) activity. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2007 Dec; 45(12):2359-65. doi: 10.1016/j.fct.2007.06.012. [PMID: 17658211]
  • Michael c Tims, Charisma Batista. Effects of root isoquinoline alkaloids from Hydrastis canadensis on Fusarium oxysporum isolated from Hydrastis root tissue. Journal of chemical ecology. 2007 Jul; 33(7):1449-55. doi: 10.1007/s10886-007-9319-9. [PMID: 17549565]
  • David K Liscombe, Peter J Facchini. Molecular cloning and characterization of tetrahydroprotoberberine cis-N-methyltransferase, an enzyme involved in alkaloid biosynthesis in opium poppy. The Journal of biological chemistry. 2007 May; 282(20):14741-51. doi: 10.1074/jbc.m611908200. [PMID: 17389594]
  • Parveen Abidi, Wei Chen, Fredric B Kraemer, Hai Li, Jingwen Liu. The medicinal plant goldenseal is a natural LDL-lowering agent with multiple bioactive components and new action mechanisms. Journal of lipid research. 2006 Oct; 47(10):2134-47. doi: 10.1194/jlr.m600195-jlr200. [PMID: 16885565]
  • Jianhong Tao, Xiaoqi Zhang, Wencai Ye, Shouxun Zhao. [Chemical constituents from Corydalis humosa]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2005 Jul; 28(7):556-7. doi: . [PMID: 16252721]
  • L A D Williams, H Rösner, W Möller, J Conrad, J P Nkurunziza, W Kraus. In vitro anti-proliferation/cytotoxic activity of sixty natural products on the human SH-SY5Y neuroblastoma cells with specific reference to dibenzyl trisulphide. The West Indian medical journal. 2004 Sep; 53(4):208-19. doi: ". [PMID: 15622673]
  • Shin-Ya Saito, Masashi Tanaka, Kimihiro Matsunaga, Yushan Li, Yasushi Ohizumi. The combination of rat mast cell and rabbit aortic smooth muscle is the simple bioassay for the screening of anti-allergic ingredient from methanolic extract of Corydalis tuber. Biological & pharmaceutical bulletin. 2004 Aug; 27(8):1270-4. doi: 10.1248/bpb.27.1270. [PMID: 15305035]
  • Holly A Weber, Maureen Joseph. [Extraction and HPLC analysis of alkaloids in goldenseal]. Sheng wu gong cheng xue bao = Chinese journal of biotechnology. 2004 Mar; 20(2):306-8. doi: . [PMID: 15969129]
  • Holly A Weber, Matthew K Zart, Andrew E Hodges, H Michael Molloy, Brandon M O'Brien, Leslie A Moody, Alice P Clark, Roger K Harris, J Diane Overstreet, Cynthia S Smith. Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers. Journal of agricultural and food chemistry. 2003 Dec; 51(25):7352-8. doi: 10.1021/jf034339r. [PMID: 14640583]
  • Holly A Weber, Matthew K Zart, Andrew E Hodges, Kellie D White, Sarah M Barnes, Leslie A Moody, Alice P Clark, Roger K Harris, J Diane Overstreet, Cynthia S Smith. Method validation for determination of alkaloid content in goldenseal root powder. Journal of AOAC International. 2003 May; 86(3):476-83. doi: . [PMID: 12852562]
  • C de Coupade, M N Ajuebor, F Russo-Marie, M Perretti, E Solito. Cytokine modulation of liver annexin 1 expression during experimental endotoxemia. The American journal of pathology. 2001 Oct; 159(4):1435-43. doi: 10.1016/s0002-9440(10)62530-8. [PMID: 11583971]
  • F Scazzocchio, M F Cometa, L Tomassini, M Palmery. Antibacterial activity of Hydrastis canadensis extract and its major isolated alkaloids. Planta medica. 2001 Aug; 67(6):561-4. doi: 10.1055/s-2001-16493. [PMID: 11509983]
  • C W Lau, X Q Yao, Z Y Chen, W H Ko, Y Huang. Cardiovascular actions of berberine. Cardiovascular drug reviews. 2001; 19(3):234-44. doi: 10.1111/j.1527-3466.2001.tb00068.x. [PMID: 11607041]
  • H Abdel-Haq, M F Cometa, M Palmery, M G Leone, B Silvestrini, L Saso. Relaxant effects of Hydrastis canadensis L. and its major alkaloids on guinea pig isolated trachea. Pharmacology & toxicology. 2000 Nov; 87(5):218-22. doi: 10.1034/j.1600-0773.2000.d01-77.x. [PMID: 11129501]
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