1,2,3,4-Tetrahydro-beta-carboline (BioDeep_00000017936)

   

human metabolite Endogenous


代谢物信息卡片


9H-1,2,3,4-tetrahydropyrido(3,4-b)Indole

化学式: C11H12N2 (172.1000432)
中文名称: 1,2,3,4-四氢-β-咔啉
谱图信息: 最多检出来源 Bos taurus(endogenous) 75%

分子结构信息

SMILES: C1(NC2=C3CCNC2)=C3C=CC=C1
InChI: InChI=1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2

描述信息

Tetrahydro-b-carbolines (THbCs)are potential neuroactive alkaloids found in chocolate and cocoa. The formation of 1,2,3,4-tetrahydro-/3-carbolines (THBCs), via the Pictet-Spengler condensation of tryptamines with formaldehyde, has been demonstrated repeatedly in incubations of various mammalian tissues containing added indolethylamine substrate and the methyl donors .5-methyltetrahydrofolate (5-MTHF) or S-adenosylmethionine(SAM). It is concluded that the formation of these THBCs is an artifact produced by the enzymatic liberation of formaldehyde from the methyl donors and the subsequent non-enzymatic condensation of this formaldehyde with the indole substrates. The formation of THBCs in vivo has thus remained a point of contention. (PMID: 7213417). 1,2,3,4-Tetrahydro-beta-carboline is a biomarker for the consumption of beer
Tetrahydro-b-carbolines (THbCs)are potential neuroactive alkaloids found in chocolate and cocoa.
D009676 - Noxae > D009498 - Neurotoxins
Tetrahydro-β-carboline (Tryptoline) is a metabolite of tryptamine, also is a competitive serotonin reuptake inhibitor with an Ki value of 6.1 μM[1].

同义名列表

16 个代谢物同义名

9H-1,2,3,4-tetrahydropyrido(3,4-b)Indole; 1H,2H,3H,4H,9H-pyrido[3,4-b]indole; 1,2,3,4-Tetrahydro-beta-carboline; 1,2,3,4-Tetrahydro-b-carboline; 1,2,3,4-Tetrahydro-β-carboline; 1,2,3,4-Tetrahydronorharmane; Tryptoline monohydrochloride; tetrahydro-beta-Carboline; Tryptoline hydrochloride; Tetrahydronorharmane; Noreleagnine; Tryptoline; Triptoline; THbetaC; THBC; Tetrahydro-β-carboline



数据库引用编号

10 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

3 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

  • Hong-Wu Liu, Shan-Shan Su, Si-Yue Ma, Ting Li, Wang Fang, Yue Ding, Shi-Tao Liu, Jun-Rong Zhang, Hong-Mei Xiang, Xiang Zhou, Song Yang. Discovery and Structural Optimization of 1,2,3,4-Tetrahydro-β-carbolines as Novel Reactive Oxygen Species Inducers for Controlling Intractable Plant Bacterial Diseases. Journal of agricultural and food chemistry. 2023 Jul; 71(29):11035-11047. doi: 10.1021/acs.jafc.3c02615. [PMID: 37450840]
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  • Bei Zhou, Zheng-Fen Liu, Guo-Gang Deng, Wen Chen, Min-Yan Li, Li-Juan Yang, Yan Li, Xiao-Dong Yang, Hong-Bin Zhang. Synthesis and antitumor activity of novel N-substituted tetrahydro-β-carboline-imidazolium salt derivatives. Organic & biomolecular chemistry. 2016 Oct; 14(39):9423-9430. doi: 10.1039/c6ob01495j. [PMID: 27714171]
  • Bing-Huo Zhang, Zhang-Gui Ding, Han-Quan Li, Xiao-Zhen Mou, Yu-Qin Zhang, Jian-Yuan Yang, En-Min Zhou, Wen-Jun Li. Algicidal Activity of Streptomyces eurocidicus JXJ-0089 Metabolites and Their Effects on Microcystis Physiology. Applied and environmental microbiology. 2016 09; 82(17):5132-43. doi: 10.1128/aem.01198-16. [PMID: 27316950]
  • Xiaomin Wang, Rui Liu, Yukun Yang, Min Zhang. Isolation, purification and identification of antioxidants in an aqueous aged garlic extract. Food chemistry. 2015 Nov; 187(?):37-43. doi: 10.1016/j.foodchem.2015.03.109. [PMID: 25976995]
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  • Yongxian Liu, Hongjian Song, Yuanqiong Huang, Jiarui Li, Sheng Zhao, Yuchuan Song, Peiwen Yang, Zhixin Xiao, Yuxiu Liu, Yongqiang Li, Hui Shang, Qingmin Wang. Design, synthesis, and antiviral, fungicidal, and insecticidal activities of tetrahydro-β-carboline-3-carbohydrazide derivatives. Journal of agricultural and food chemistry. 2014 Oct; 62(41):9987-99. doi: 10.1021/jf503794g. [PMID: 25280351]
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  • Claudia A do Nascimento, Luciano M Lião, Lucília Kato, Cleuza C da Silva, Clara M A Tanaka, Ivânia T A Schuquel, Cecília M A de Oliveira. A tetrahydro beta-carboline trisaccharide from Palicourea coriacea (Cham.) K. Schum. Carbohydrate research. 2008 May; 343(6):1104-7. doi: 10.1016/j.carres.2008.01.032. [PMID: 18329636]
  • A Storch, Y-I Hwang, G Bringmann, D Feineis, S Ott, R Brückner, J Schwarz. Cytotoxicity of chloral-derived beta-carbolines is not specific towards neuronal nor dopaminergic cells. Journal of neural transmission (Vienna, Austria : 1996). 2006 Dec; 113(12):1895-901. doi: 10.1007/s00702-006-0495-5. [PMID: 16868795]
  • Emiko Sato, Masahiro Kohno, Yoshimi Niwano. Increased level of tetrahydro-beta-carboline derivatives in short-term fermented garlic. Plant foods for human nutrition (Dordrecht, Netherlands). 2006 Dec; 61(4):175-8. doi: 10.1007/s11130-006-0028-2. [PMID: 17039401]
  • Makoto Ichikawa, Jiro Yoshida, Nagatoshi Ide, Takashi Sasaoka, Hiroyuki Yamaguchi, Kazuhisa Ono. Tetrahydro-beta-carboline derivatives in aged garlic extract show antioxidant properties. The Journal of nutrition. 2006 03; 136(3 Suppl):726S-731S. doi: 10.1093/jn/136.3.726s. [PMID: 16484551]
  • Makoto Ichikawa, Kenjiro Ryu, Jiro Yoshida, Nagatoshi Ide, Susumu Yoshida, Takashi Sasaoka, Shin-Ichiro Sumi. Antioxidant effects of tetrahydro-beta-carboline derivatives identified in aged garlic extract. BioFactors (Oxford, England). 2002; 16(3-4):57-72. doi: 10.1002/biof.5520160302. [PMID: 14530594]
  • J J García, E Martínez-Ballarín, M Robinson, J L Allué, R J Reiter, C Osuna, D Acuña-Castroviejo. Protective effect of beta-carbolines and other antioxidants on lipid peroxidation due to hydrogen peroxide in rat brain homogenates. Neuroscience letters. 2000 Nov; 294(1):1-4. doi: 10.1016/s0304-3940(00)01520-2. [PMID: 11044572]
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  • H Tsuchiya, K Yamada, K Tajima, T Hayashi. Urinary excretion of tetrahydro-beta-carbolines relating to ingestion of alcoholic beverages. Alcohol and alcoholism (Oxford, Oxfordshire). 1996 Mar; 31(2):197-203. doi: 10.1093/oxfordjournals.alcalc.a008132. [PMID: 8737016]
  • H Tsuchiya, S Ohtani, K Yamada, N Takagi, T Hayashi. Determination of tetrahydro-beta-carbolines in urine by high-performance liquid chromatography with suppression of artefact formation. Journal of pharmaceutical and biomedical analysis. 1994 Dec; 12(12):1547-53. doi: 10.1016/0731-7085(94)00097-2. [PMID: 7696379]
  • H Tsuchiya, S Ohtani, K Yamada, N Takagi, H Todoriki, T Hayashi. Quantitation of urinary 1,2,3,4-tetrahydro-beta-carboline and 1-methyl-1,2,3,4-tetrahydro-beta-carboline by high-performance liquid chromatography. Journal of pharmaceutical sciences. 1994 Mar; 83(3):415-8. doi: 10.1002/jps.2600830330. [PMID: 8207693]
  • K Horiuchi, O Yonekawa, K Iwahara, T Kanno, T Kurihara, Y Fujise. A hydrophilic tetrahydro-beta-carboline in human urine. Journal of biochemistry. 1994 Feb; 115(2):362-6. doi: 10.1093/oxfordjournals.jbchem.a124343. [PMID: 8206887]
  • F Musshoff, T Daldrup, W Bonte. Gas chromatographic-mass spectrometric screening procedure for the identification of formaldehyde-derived tetrahydro-beta-carbolines in human urine. Journal of chromatography. 1993 Apr; 614(1):1-6. doi: 10.1016/0378-4347(93)80217-r. [PMID: 8496268]
  • K Matsubara, M A Collins, E J Neafsey. Mono-N-methylation of 1,2,3,4-tetrahydro-beta-carbolines in brain cytosol: absence of indole methylation. Journal of neurochemistry. 1992 Aug; 59(2):505-10. doi: 10.1111/j.1471-4159.1992.tb09399.x. [PMID: 1629723]
  • NULL. Tetrahydro-beta-carbolines in foodstuffs, urine, and milk: physiological implications. Nutrition reviews. 1991 Dec; 49(12):367-8. doi: 10.1111/j.1753-4887.1991.tb02988.x. [PMID: 1800917]
  • J Adachi, Y Mizoi, T Naito, Y Ogawa, Y Uetani, I Ninomiya. Identification of tetrahydro-beta-carboline-3-carboxylic acid in foodstuffs, human urine and human milk. The Journal of nutrition. 1991 May; 121(5):646-52. doi: 10.1093/jn/121.5.646. [PMID: 2019874]
  • J Adachi, K Yamamoto, Y Ogawa, Y Ueno, Y Mizoi, Y Tatsuno. Endogenous formation of 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3- carboxylic acid in man as the possible causative substance of eosinophilia-myalgia syndrome associated with ingestion of L-tryptophan. Archives of toxicology. 1991; 65(6):505-9. doi: 10.1007/bf01977365. [PMID: 1929872]
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  • K Matsubara, S Fukushima, A Akane, K Hama, Y Fukui. Tetrahydro-beta-carbolines in human urine and rat brain--no evidence of formation by alcohol drinking. Alcohol and alcoholism (Oxford, Oxfordshire). 1986; 21(4):339-45. doi: . [PMID: 3814252]
  • A C Rovescalli, N Brunello, C Franzetti, G Racagni. Interaction of putative endogenous tryptolines with the hypothalamic serotonergic system and prolactin secretion in adult male rats. Neuroendocrinology. 1986; 43(5):603-10. doi: 10.1159/000124588. [PMID: 2427964]
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