beta-Carboline (BioDeep_00000002136)

 

Secondary id: BioDeep_00000397990, BioDeep_00000407563

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


Norharman hydrochloride

化学式: C11H8N2 (168.0687448)
中文名称: 9H-吡啶[3,4-b]吲哚
谱图信息: 最多检出来源 Viridiplantae(plant) 16.14%

分子结构信息

SMILES: C1=CC=C2C(=C1)C3=C(N2)C=NC=C3
InChI: InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H

描述信息

beta-Carboline, also known as norharmane, is an organic amine and is the prototype of a class of compounds known as beta-carbolines. beta-Carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. beta-Carboline is a very strong basic compound (based on its pKa). beta-Carboline alkaloids are widely distributed in plants and animals and many are inverse agonists of the GABA-A receptor complex (PMID: 17334612). Other biological activities demonstrated by these compounds include intercalation; inhibition of CDK, topoisomerase, and monoamine oxidase; and interaction with 5-hydroxy serotonin receptors. These compounds have also exhibited sedative, anxiolytic, hypnotic, anticonvulsant, antitumor, antiviral, antiparasitic, and antimicrobial activities (PMID: 17305548).
b-Carboline (9H-pyrido[3,4-b]indole) is an organic amine that is the prototype of a class of compounds known as b-carbolines. [HMDB]. Norharman is found in chicory.
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 75
CONFIDENCE standard compound; INTERNAL_ID 2883
D009676 - Noxae > D009498 - Neurotoxins
D009676 - Noxae > D009153 - Mutagens
Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC50 values of 6.5 and 4.7 μM for MAO-A and MAO-B, respectively. Norharmane causes antidepressant responses. Norharmane is also a prospective anti-cancer photosensitizer. Norharmane alters polar auxin transport (PAT) by inhibiting PIN2, PIN3 and PIN7 transport proteins, thus causing a significant inhibitory effect on the growth of Arabidopsis thaliana seedlings[1][2][3][4][5][6].
Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC50 values of 6.5 and 4.7 μM for MAO-A and MAO-B, respectively. Norharmane causes antidepressant responses. Norharmane is also a prospective anti-cancer photosensitizer. Norharmane alters polar auxin transport (PAT) by inhibiting PIN2, PIN3 and PIN7 transport proteins, thus causing a significant inhibitory effect on the growth of Arabidopsis thaliana seedlings[1][2][3][4][5][6].

同义名列表

15 个代谢物同义名

Norharman hydrochloride; 9H-Pyrido(3,4-b)indole; 9H-Pyrido[3,4-B]indole; 2,9-Diazafluorene; 9H-beta-Carboline; beta-Carboline; 9H-b-Carboline; 2-Azacarbazole; 9H-Β-carboline; Β-carboline; Carbazoline; b-Carboline; Norharmane; Norhormane; Norharman



数据库引用编号

24 个数据库交叉引用编号

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)

51 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

  • Phumudzo P Tshikhudo, Tafadzwanashe Mabhaudhi, Neil A Koorbanally, Fhatuwani N Mudau, Edgardo Oscar Avendaño Caceres, Dragos Popa, Daniela Calina, Javad Sharifi-Rad. Anticancer Potential of β-Carboline Alkaloids: An Updated Mechanistic Overview. Chemistry & biodiversity. 2023 Dec; ?(?):e202301263. doi: 10.1002/cbdv.202301263. [PMID: 38108650]
  • Qi Zhou, Xufeng Tao, Fangyue Guo, Yu Wu, Dawei Deng, Linlin Lv, Deshi Dong, Dong Shang, Hong Xiang. Tryptophan metabolite norharman secreted by cultivated Lactobacillus attenuates acute pancreatitis as an antagonist of histone deacetylases. BMC medicine. 2023 Aug; 21(1):329. doi: 10.1186/s12916-023-02997-2. [PMID: 37635214]
  • Tao Sheng, Chenjie Yu, Yujie Wang, Shengkun Li, Huijun Wu, Qin Gu, Guangrong Meng, Alastair N Herron, Xuewen Gao. Chromatography-Free Synthesis of β-Carboline 1-Hydrazides and an Investigation of the Mechanism of Their Bioactivity: The Discovery of β-Carbolines as Promising Antifungal and Antibacterial Candidates. Journal of medicinal chemistry. 2023 07; 66(13):9040-9056. doi: 10.1021/acs.jmedchem.3c00650. [PMID: 37314697]
  • Tomás Herraiz. β-Carboline Alkaloids in Soy Sauce and Inhibition of Monoamine Oxidase (MAO). Molecules (Basel, Switzerland). 2023 Mar; 28(6):. doi: 10.3390/molecules28062723. [PMID: 36985694]
  • Yuanyuan Wang, Maofeng Dong, Limin Guo, Yamin Zhu, Qingqing Jiang, Jianbo Xiao, Mingfu Wang, Yueliang Zhao. Effect of acrolein on the formation of harman and norharman in chemical models and roast beef patties. Food research international (Ottawa, Ont.). 2023 02; 164(?):112465. doi: 10.1016/j.foodres.2023.112465. [PMID: 36738015]
  • Huiya Ma, Hongzhi Yu, Zhengyang Li, Zhi Cao, Youwei Du, Jiangkun Dai, Dongming Zhi, Yujie Xu, Na Li, Junru Wang. β-Carboline dimers inhibit the tumor proliferation by the cell cycle arrest of sarcoma through intercalating to Cyclin-A2. Frontiers in immunology. 2022; 13(?):922183. doi: 10.3389/fimmu.2022.922183. [PMID: 36325324]
  • Wei Liu, Zhaoyu Yang, Lili Shi, Ziyu Cui, Yun Li. Degradation of β-Carbolines Harman and Norharman in Edible Oils during Heating. Molecules (Basel, Switzerland). 2021 Nov; 26(22):. doi: 10.3390/molecules26227018. [PMID: 34834111]
  • Bo Luo, Xinqiang Song. A comprehensive overview of β-carbolines and its derivatives as anticancer agents. European journal of medicinal chemistry. 2021 Nov; 224(?):113688. doi: 10.1016/j.ejmech.2021.113688. [PMID: 34332400]
  • Cheng-Peng Sun, Jing Yi, Fan Wei, Xia Lv, Sa Deng, Bao-Jing Zhang, Wen-Yu Zhao, Xiao-Chi Ma. UV-light-driven photooxidation of harmaline catalyzed by riboflavin: Product characterization and mechanisms. Fitoterapia. 2021 Nov; 155(?):105054. doi: 10.1016/j.fitote.2021.105054. [PMID: 34626737]
  • Andrew B Hawkey, Julia Hoeng, Manuel C Peitsch, Edward D Levin, Kyoko Koshibu. Subchronic effects of plant alkaloids on anxiety-like behavior in zebrafish. Pharmacology, biochemistry, and behavior. 2021 08; 207(?):173223. doi: 10.1016/j.pbb.2021.173223. [PMID: 34197843]
  • Yuxiang Fan, Fanye Zeng, Lili Ma, Hongliang Zhang. Effects of β-carboline alkaloids from Peganum harmala on the FAK/PI3K/AKT/Mtor pathway in human gastric cancer cell line SGC-7901 and tumor-bearing mice. Pakistan journal of pharmaceutical sciences. 2021 May; 34(3):891-898. doi: . [PMID: 34602411]
  • Walaa Alharbi, Iftekhar Hassan, Rais Ahmad Khan, Shazia Parveen, Khadijah H Alharbi, Ibtisam I Bin Sharfan, Ibrahim M Alhazza, Hossam Ebaid, Ali Alsalme. Bioactive Tryptophan-Based Copper Complex with Auxiliary β-Carboline Spectacle Potential on Human Breast Cancer Cells: In Vitro and In Vivo Studies. Molecules (Basel, Switzerland). 2021 Mar; 26(6):. doi: 10.3390/molecules26061606. [PMID: 33799355]
  • Hyojik Yang, Shelley N Jackson, Amina S Woods, David R Goodlett, Robert K Ernst, Alison J Scott. Streamlined Analysis of Cardiolipins in Prokaryotic and Eukaryotic Samples Using a Norharmane Matrix by MALDI-MSI. Journal of the American Society for Mass Spectrometry. 2020 Dec; 31(12):2495-2502. doi: 10.1021/jasms.0c00201. [PMID: 32924474]
  • Sheng-Ge Li, Yue-Tong Wang, Qin Zhang, Kai-Bo Wang, Jing-Jing Xue, Da-Hong Li, Yong-Kui Jing, Bin Lin, Hui-Ming Hua. Pegaharmols A-B, Axially Chiral β-Carboline-quinazoline Dimers from the Roots of Peganum harmala. Organic letters. 2020 10; 22(19):7522-7525. doi: 10.1021/acs.orglett.0c02709. [PMID: 32936652]
  • Zhong-Nan Wu, Neng-Hua Chen, Qing Tang, Si Chen, Zhao-Chun Zhan, Yu-Bo Zhang, Guo-Cai Wang, Yao-Lan Li, Wen-Cai Ye. β-Carboline Alkaloids from the Seeds of Peganum harmala and Their Anti-HSV-2 Virus Activities. Organic letters. 2020 09; 22(18):7310-7314. doi: 10.1021/acs.orglett.0c02650. [PMID: 32896126]
  • Chen-Xia Zhang, Jun Xi, Tian-Pei Zhao, Yu-Xiang Ma, Xue-De Wang. β-carbolines norharman and harman in vegetable oils in China. Food additives & contaminants. Part B, Surveillance. 2020 Sep; 13(3):193-199. doi: 10.1080/19393210.2020.1759701. [PMID: 32364007]
  • Renata Zawirska-Wojtasiak, Agnieszka Fedoruk-Wyszomirska, Paulina Piechowska, Sylwia Mildner-Szkudlarz, Joanna Bajerska, Elżbieta Wojtowicz, Krzysztof Przygoński, Dorota Gurda, Wiktoria Kubicka, Eliza Wyszko. β-Carbolines in Experiments on Laboratory Animals. International journal of molecular sciences. 2020 Jul; 21(15):. doi: 10.3390/ijms21155245. [PMID: 32722000]
  • David López-González, Aitana Costas-Gil, Manuel J Reigosa, Fabrizio Araniti, Adela M Sánchez-Moreiras. A natural indole alkaloid, norharmane, affects PIN expression patterns and compromises root growth in Arabidopsis thaliana. Plant physiology and biochemistry : PPB. 2020 Jun; 151(?):378-390. doi: 10.1016/j.plaphy.2020.03.047. [PMID: 32278957]
  • Tapas Ghosh, Sarita Sarkar, Paromita Bhattacharjee, Gopal Chandra Jana, Maidul Hossain, Prateek Pandya, Kakali Bhadra. In vitro relationship between serum protein binding to beta-carboline alkaloids: a comparative cytotoxic, spectroscopic and calorimetric assays. Journal of biomolecular structure & dynamics. 2020 03; 38(4):1103-1118. doi: 10.1080/07391102.2019.1595727. [PMID: 30909826]
  • Yukari Totsuka, Keiji Wakabayashi. Biological significance of aminophenyl-β-carboline derivatives formed from co-mutagenic action of β-carbolines and aniline and o-toluidine and its effect on tumorigenesis in humans: A review. Mutation research. Genetic toxicology and environmental mutagenesis. 2020 Feb; 850-851(?):503148. doi: 10.1016/j.mrgentox.2020.503148. [PMID: 32247557]
  • Bo Jiang, Liyuan Meng, Nan Zou, Hanxue Wang, Shuping Li, Lifeng Huang, Xuemei Cheng, Zhengtao Wang, Wansheng Chen, Changhong Wang. Mechanism-based pharmacokinetics-pharmacodynamics studies of harmine and harmaline on neurotransmitters regulatory effects in healthy rats: Challenge on monoamine oxidase and acetylcholinesterase inhibition. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Sep; 62(?):152967. doi: 10.1016/j.phymed.2019.152967. [PMID: 31154274]
  • Falco Beer, Felix Urbat, Charles M A P Franz, Melanie Huch, Sabine E Kulling, Mirko Bunzel, Diana Bunzel. The Human Fecal Microbiota Metabolizes Foodborne Heterocyclic Aromatic Amines by Reuterin Conjugation and Further Transformations. Molecular nutrition & food research. 2019 05; 63(10):e1801177. doi: 10.1002/mnfr.201801177. [PMID: 30815965]
  • Paulina Piechowska, Renata Zawirska-Wojtasiak, Sylwia Mildner-Szkudlarz. Bioactive β-Carbolines in Food: A Review. Nutrients. 2019 Apr; 11(4):. doi: 10.3390/nu11040814. [PMID: 30978920]
  • Yannick Hövelmann, Lea Lewin, Florian Hübner, Hans-Ulrich Humpf. Large-Scale Screening of Foods for Glucose-Derived β-Carboline Alkaloids by Stable Isotope Dilution LC-MS/MS. Journal of agricultural and food chemistry. 2019 Apr; 67(14):3890-3899. doi: 10.1021/acs.jafc.8b07150. [PMID: 30875225]
  • Ivano Vigliante, Giuseppe Mannino, Massimo E Maffei. Chemical Characterization and DNA Fingerprinting of Griffonia simplicifolia Baill. Molecules (Basel, Switzerland). 2019 Mar; 24(6):. doi: 10.3390/molecules24061032. [PMID: 30875930]
  • Wen-Yu Zhao, Wei-Yu Zhou, Jing-Jie Chen, Guo-Dong Yao, Bin Lin, Xiao-Bo Wang, Xiao-Xiao Huang, Shao-Jiang Song. Enantiomeric β-carboline dimers from Picrasma quassioides and their anti-hepatoma potential. Phytochemistry. 2019 Mar; 159(?):39-45. doi: 10.1016/j.phytochem.2018.12.002. [PMID: 30577000]
  • Junmin Xi, Zhijun Zhang, Qi Zhu, Guohua Zhong. Evolution from Natural β-Carboline Alkaloids to Obtain 1,2,4,9-tetrahydro-3-thia-9-aza-fluorene Derivatives as Potent Fungicidal Agents against Rhizoctonia solani. International journal of molecular sciences. 2018 Dec; 19(12):. doi: 10.3390/ijms19124044. [PMID: 30558145]
  • Ram B Jain. Concentrations of selected heterocyclic aromatic amines among US population aged ≥ 6 years: data from NHANES 2013-2014. Environmental science and pollution research international. 2018 Jul; 25(20):19859-19874. doi: 10.1007/s11356-018-2210-0. [PMID: 29737487]
  • Usama W Hawas, Lamia T Abou El-Kassem, Mohamed S Abdelfattah, Mohammed I Y Elmallah, Mennat Allah G Eid, Marwa Monier, N Marimuthu. Cytotoxic activity of alkyl benzoate and fatty acids from the red sea sponge Hyrtios erectus. Natural product research. 2018 Jun; 32(12):1369-1374. doi: 10.1080/14786419.2017.1344662. [PMID: 28669229]
  • Hyun Sook Kwon, Hanna Lee, Jin Su Lee, Kijun Lee, Jung-Hye Choi, Dae Sik Jang. Two new β-carboline alkaloids from the stems of Picrasma quassioides. Archives of pharmacal research. 2018 May; 41(5):513-518. doi: 10.1007/s12272-018-1034-2. [PMID: 29725985]
  • T Toyoda, Y Totsuka, K Matsushita, T Morikawa, N Miyoshi, K Wakabayashi, K Ogawa. γ-H2AX formation in the urinary bladder of rats treated with two norharman derivatives obtained from o-toluidine and aniline. Journal of applied toxicology : JAT. 2018 04; 38(4):537-543. doi: 10.1002/jat.3560. [PMID: 29143974]
  • Xinke Zhang, Peng Li, Shaohua Guo, Shuqi Wang, Dasheng Liu. Quantitation of β-carboline and quercetin in alligator weed (Alternanthera philoxeroides (Mart.) Griseb.) by LC-MS/MS and evaluation of cardioprotective effects of the methanol extracts. Drug discoveries & therapeutics. 2018 ; 12(6):341-346. doi: 10.5582/ddt.2018.01070. [PMID: 30674768]
  • Jin-Hyung Lee, Yong-Guy Kim, Sang Hee Shim, Jintae Lee. Antibiofilm activities of norharmane and its derivatives against Escherichia coli O157:H7 and other bacteria. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2017 Dec; 36(?):254-261. doi: 10.1016/j.phymed.2017.10.013. [PMID: 29157822]
  • Jincan Chen, Fa Peng, Yao Zhang, Baojun Li, Ji She, Xinming Jie, Zhilin Zou, Man Chen, Lanmei Chen. Synthesis, characterization, cellular uptake and apoptosis-inducing properties of two highly cytotoxic cyclometalated ruthenium(II) β-carboline complexes. European journal of medicinal chemistry. 2017 Nov; 140(?):104-117. doi: 10.1016/j.ejmech.2017.09.007. [PMID: 28923379]
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  • Shuai Zhao, Yuichiro Kanno, Wei Li, Tatsunori Sasaki, Xiangyu Zhang, Jian Wang, Maosheng Cheng, Kazuo Koike, Kiyomitsu Nemoto, Huicheng Li. Identification of Picrasidine C as a Subtype-Selective PPARα Agonist. Journal of natural products. 2016 Dec; 79(12):3127-3133. doi: 10.1021/acs.jnatprod.6b00883. [PMID: 27958735]
  • Tekalign Kejela, Vasudev R Thakkar, Parth Thakor. Bacillus species (BT42) isolated from Coffea arabica L. rhizosphere antagonizes Colletotrichum gloeosporioides and Fusarium oxysporum and also exhibits multiple plant growth promoting activity. BMC microbiology. 2016 Nov; 16(1):277. doi: 10.1186/s12866-016-0897-y. [PMID: 27863465]
  • Hyun Woo Lee, Hyung Won Ryu, Myung-Gyun Kang, Daeui Park, Sei-Ryang Oh, Hoon Kim. Potent selective monoamine oxidase B inhibition by maackiain, a pterocarpan from the roots of Sophora flavescens. Bioorganic & medicinal chemistry letters. 2016 10; 26(19):4714-4719. doi: 10.1016/j.bmcl.2016.08.044. [PMID: 27575476]
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