Norharman (BioDeep_00000407563)

Main id: BioDeep_00000002136

Secondary id: BioDeep_00000397990

natural product PANOMIX_OTCML-2023


代谢物信息卡片


InChI=1\C11H8N2\c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10\h1-7,13

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 Homo sapiens(natural_products) 0.67%

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

D009676 - Noxae > D009498 - Neurotoxins
D009676 - Noxae > D009153 - Mutagens
Annotation level-1
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

46 个代谢物同义名

InChI=1\C11H8N2\c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10\h1-7,13; 5-23-08-00220 (Beilstein Handbook Reference); 9H-Pyrido[3,4-B]indole; SDCCGMLS-0003278.P003; WLN: T B656 EN HMJ; Carbazoline (VAN); 2,9-Diazafluorene; 9H-beta-Carboline; Spectrum4_001915; Spectrum5_000630; Spectrum2_000588; Spectrum3_000741; .beta.-Carboline; EINECS 205-959-0; Spectrum_001132; 9H-$b-carboline; AG-670\31510009; NCGC00021302-03; NCIOpen2_001217; 2-Azacarbazole; Prestwick_363; KBioSS_001612; KBioGR_002537; BSPBio_002322; SMR000058207; SPBio_000436; MLS000069651; KBio3_001542; KBio2_004180; KBio2_001612; KBio2_006748; ZINC00066039; AIDS-109050; SMP2_000349; N6252_SIGMA; Carbazoline; BRN 0128414; CCRIS 6915; Norharmane; AIDS109050; NSC 84417; Norharman; ST5307983; NSC84417; 244-63-3; β-Carboline



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)

58 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]
  • Marcos Tascón, Fernando Benavente, Nora M Vizioli, Leonardo G Gagliardi. A rapid and simple method for the determination of psychoactive alkaloids by CE-UV: application to Peganum Harmala seed infusions. Drug testing and analysis. 2017 Apr; 9(4):596-602. doi: 10.1002/dta.1989. [PMID: 27377797]
  • 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]
  • K P C Kuypers, J Riba, M de la Fuente Revenga, S Barker, E L Theunissen, J G Ramaekers. Ayahuasca enhances creative divergent thinking while decreasing conventional convergent thinking. Psychopharmacology. 2016 Sep; 233(18):3395-403. doi: 10.1007/s00213-016-4377-8. [PMID: 27435062]
  • Kai-Bo Wang, Da-Hong Li, Ping Hu, Wen-Jing Wang, Clement Lin, Jian Wang, Bin Lin, Jiao Bai, Yue-Hu Pei, Yong-Kui Jing, Zhan-Lin Li, Danzhou Yang, Hui-Ming Hua. A Series of β-Carboline Alkaloids from the Seeds of Peganum harmala Show G-Quadruplex Interactions. Organic letters. 2016 07; 18(14):3398-401. doi: 10.1021/acs.orglett.6b01560. [PMID: 27340903]
  • Simon Beaudoin, Jeffrey V Leyton. Development of a Novel Covalent Folate-Albumin-Photosensitizer Conjugate. Photochemistry and photobiology. 2016 07; 92(4):512-4. doi: 10.1111/php.12603. [PMID: 27221219]
  • Martin G Thomas, Roxanne M Marwood, Anna E Parsons, Richard B Parsons. The effect of foetal bovine serum supplementation upon the lactate dehydrogenase cytotoxicity assay: Important considerations for in vitro toxicity analysis. Toxicology in vitro : an international journal published in association with BIBRA. 2015 Dec; 30(1 Pt B):300-8. doi: 10.1016/j.tiv.2015.10.007. [PMID: 26498060]
  • Saptarshi Ghosh, Satrajit Chakrabarty, Debipreeta Bhowmik, Gopinatha Suresh Kumar, Nitin Chattopadhyay. Stepwise unfolding of bovine and human serum albumin by an anionic surfactant: an investigation using the proton transfer probe norharmane. The journal of physical chemistry. B. 2015 Feb; 119(6):2090-102. doi: 10.1021/jp501150p. [PMID: 24673409]
  • Tomás Herraiz, Juan Galisteo. Naturally-occurring tetrahydro-β-carboline alkaloids derived from tryptophan are oxidized to bioactive β-carboline alkaloids by heme peroxidases. Biochemical and biophysical research communications. 2014 Aug; 451(1):42-7. doi: 10.1016/j.bbrc.2014.07.047. [PMID: 25035927]
  • Celesztina Domonkos, Ilona Fitos, Júlia Visy, Ferenc Zsila. Fatty acid modulated human serum albumin binding of the β-carboline alkaloids norharmane and harmane. Molecular pharmaceutics. 2013 Dec; 10(12):4706-16. doi: 10.1021/mp400531n. [PMID: 24171410]
  • Keisuke Eguchi, Yukio Fujiwara, Akinori Hayashida, Hasita Horlad, Hikaru Kato, Henki Rotinsulu, Fitje Losung, Remy E P Mangindaan, Nicole J de Voogd, Motohiro Takeya, Sachiko Tsukamoto. Manzamine A, a marine-derived alkaloid, inhibits accumulation of cholesterol ester in macrophages and suppresses hyperlipidemia and atherosclerosis in vivo. Bioorganic & medicinal chemistry. 2013 Jul; 21(13):3831-8. doi: 10.1016/j.bmc.2013.04.025. [PMID: 23665143]
  • Monika Gibis, Jochen Weiss. Antioxidant capacity and inhibitory effect of grape seed and rosemary extract in marinades on the formation of heterocyclic amines in fried beef patties. Food chemistry. 2012 Sep; 134(2):766-74. doi: 10.1016/j.foodchem.2012.02.179. [PMID: 23107689]
  • Akpanabiatu Monday Isaiah, Otitoju Olawale, Edet Emmanuel Effiong, Ndem Jessie Idongesit, Uwah Anthony Fidelis, Ufot Usenobong Friday. Vitamin e supplementation with rauwolfia vomitoria root bark extract improves hematological indices. North American journal of medical sciences. 2012 Feb; 4(2):86-9. doi: 10.4103/1947-2714.93383. [PMID: 22408754]
  • Way K W Lau, Moira M W Chan-Yeung, Benjamin H K Yip, Amy H K Cheung, Mary S M Ip, Judith C W Mak. The role of circulating serotonin in the development of chronic obstructive pulmonary disease. PloS one. 2012; 7(2):e31617. doi: 10.1371/journal.pone.0031617. [PMID: 22319639]
  • Horace T B Ho, Yongmei Pan, Zhiyi Cui, Haichuan Duan, Peter W Swaan, Joanne Wang. Molecular analysis and structure-activity relationship modeling of the substrate/inhibitor interaction site of plasma membrane monoamine transporter. The Journal of pharmacology and experimental therapeutics. 2011 Nov; 339(2):376-85. doi: 10.1124/jpet.111.184036. [PMID: 21816955]
  • David P Dixon, Jonathan D Sellars, Robert Edwards. The Arabidopsis phi class glutathione transferase AtGSTF2: binding and regulation by biologically active heterocyclic ligands. The Biochemical journal. 2011 Aug; 438(1):63-70. doi: 10.1042/bj20101884. [PMID: 21631432]
  • Zhengquan Lai, Yuyang Yi, Huijun Liao, Jiyan Su, Zhuyuan Liao, Ji Lin, Ziren Su. [Fingerprint research and multi-component quantitative analysis of Kumu injection by HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Jul; 36(13):1739-43. doi: ". [PMID: 22032136]
  • Yamin Bibi, Sobia Nisa, Fayyaz M Chaudhary, Muhammad Zia. Antibacterial activity of some selected medicinal plants of Pakistan. BMC complementary and alternative medicine. 2011 Jun; 11(?):52. doi: 10.1186/1472-6882-11-52. [PMID: 21718504]
  • Yun Li, Rita Sattler, Eun Ju Yang, Alice Nunes, Yoko Ayukawa, Sadia Akhtar, Grace Ji, Ping-Wu Zhang, Jeffrey D Rothstein. Harmine, a natural beta-carboline alkaloid, upregulates astroglial glutamate transporter expression. Neuropharmacology. 2011 Jun; 60(7-8):1168-75. doi: 10.1016/j.neuropharm.2010.10.016. [PMID: 21034752]
  • Víctor González-Ruiz, Ana I Olives, M Antonia Martín. SPE/RP-HPLC using C1 columns: an environmentally friendly alternative to conventional reverse-phase separations for quantitation of beta-carboline alkaloids in human serum samples. Analytical and bioanalytical chemistry. 2011 Apr; 400(2):395-401. doi: 10.1007/s00216-010-4562-2. [PMID: 21193904]
  • Thayele Purayil Hamsa, Girija Kuttan. Harmine activates intrinsic and extrinsic pathways of apoptosis in B16F-10 melanoma. Chinese medicine. 2011 Mar; 6(1):11. doi: 10.1186/1749-8546-6-11. [PMID: 21429205]
  • Eric Deharo, Hagai Ginsburg. Analysis of additivity and synergism in the anti-plasmodial effect of purified compounds from plant extracts. Malaria journal. 2011 Mar; 10 Suppl 1(?):S5. doi: 10.1186/1475-2875-10-s1-s5. [PMID: 21411016]
  • Fernando De Andrés, Mohammed Zougagh, Gregorio Castañeda, José Luis Sánchez-Rojas, Angel Ríos. Screening of non-polar heterocyclic amines in urine by microextraction in packed sorbent-fluorimetric detection and confirmation by capillary liquid chromatography. Talanta. 2011 Feb; 83(5):1562-7. doi: 10.1016/j.talanta.2010.11.060. [PMID: 21238752]
  • Elizabeth A Mazzio, Fran Close, Karam F A Soliman. The biochemical and cellular basis for nutraceutical strategies to attenuate neurodegeneration in Parkinson's disease. International journal of molecular sciences. 2011 Jan; 12(1):506-69. doi: 10.3390/ijms12010506. [PMID: 21340000]
  • Hironori Tsuchiya. Comparative Effects of α-, β-, and γ-Carbolines on Platelet Aggregation and Lipid Membranes. Journal of toxicology. 2011; 2011(?):151596. doi: 10.1155/2011/151596. [PMID: 21876689]
  • T Hamsa, Girija Kuttan. Studies on anti-metastatic and anti-invasive effects of harmine using highly metastatic murine B16F-10 melanoma cells. Journal of environmental pathology, toxicology and oncology : official organ of the International Society for Environmental Toxicology and Cancer. 2011; 30(2):123-37. doi: 10.1615/jenvironpatholtoxicoloncol.v30.i2.40. [PMID: 21967457]
  • T P Hamsa, Girija Kuttan. Harmine inhibits tumour specific neo-vessel formation by regulating VEGF, MMP, TIMP and pro-inflammatory mediators both in vivo and in vitro. European journal of pharmacology. 2010 Dec; 649(1-3):64-73. doi: 10.1016/j.ejphar.2010.09.010. [PMID: 20858484]
  • Sun Young Park, Young Hun Kim, Young Hee Kim, Geuntae Park, Sang-Joon Lee. Beta-carboline alkaloids harmaline and harmalol induce melanogenesis through p38 mitogen-activated protein kinase in B16F10 mouse melanoma cells. BMB reports. 2010 Dec; 43(12):824-9. doi: 10.5483/bmbrep.2010.43.12.824. [PMID: 21189160]
  • Young Sun Lee, Jae Ha Yang, Man Jong Bae, Wang Keun Yoo, Shen Ye, Charlie C L Xue, Chun Guang Li. Anti-oxidant and Anti-hypercholesterolemic Activities of Wasabia japonica. Evidence-based complementary and alternative medicine : eCAM. 2010 Dec; 7(4):459-64. doi: 10.1093/ecam/nen038. [PMID: 18955343]
  • Gomah Nenaah. Antibacterial and antifungal activities of (beta)-carboline alkaloids of Peganum harmala (L) seeds and their combination effects. Fitoterapia. 2010 Oct; 81(7):779-82. doi: 10.1016/j.fitote.2010.04.004. [PMID: 20398742]
  • Gislaine Z Réus, Roberto B Stringari, Bruna de Souza, Fabrícia Petronilho, Felipe Dal-Pizzol, Jaime E Hallak, Antônio W Zuardi, José A Crippa, João Quevedo. Harmine and imipramine promote antioxidant activities in prefrontal cortex and hippocampus. Oxidative medicine and cellular longevity. 2010 Sep; 3(5):325-31. doi: 10.4161/oxim.3.5.13109. [PMID: 21150338]
  • Thomas Haarmann-Stemmann, Jandirk Sendker, Christine Götz, Nathalie Krug, Hanno Bothe, Ellen Fritsche, Peter Proksch, Josef Abel. Regulation of dioxin receptor function by different beta-carboline alkaloids. Archives of toxicology. 2010 Aug; 84(8):619-29. doi: 10.1007/s00204-010-0548-2. [PMID: 20449727]
  • Wei-Hua Jiao, Hao Gao, Chen-Yang Li, Guang-Xiong Zhou, Susumu Kitanaka, Atsuko Ohmura, Xin-Sheng Yao. Beta-carboline alkaloids from the stems of Picrasma quassioides. Magnetic resonance in chemistry : MRC. 2010 Jun; 48(6):490-5. doi: 10.1002/mrc.2602. [PMID: 20474029]
  • T Herraiz, D González, C Ancín-Azpilicueta, V J Arán, H Guillén. beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO). Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2010 Mar; 48(3):839-45. doi: 10.1016/j.fct.2009.12.019. [PMID: 20036304]
  • Norhazlina Abdul Wahab, Norfilza M Mokhtar, Wan Nurul Heriza A Halim, Srijit Das. The effect of eurycoma longifolia Jack on spermatogenesis in estrogen-treated rats. Clinics (Sao Paulo, Brazil). 2010; 65(1):93-8. doi: 10.1590/s1807-59322010000100014. [PMID: 20126351]
  • Rosa Busquets, Jan Ake Jönsson, Henrik Frandsen, Lluís Puignou, Maria Teresa Galceran, Kerstin Skog. Hollow fibre-supported liquid membrane extraction and LC-MS/MS detection for the analysis of heterocyclic amines in urine samples. Molecular nutrition & food research. 2009 Dec; 53(12):1496-504. doi: 10.1002/mnfr.200800577. [PMID: 19810020]
  • Jean-Marie Launay, Muriel Del Pino, Gilles Chironi, Jacques Callebert, Katell Peoc'h, Jean-Louis Mégnien, Jacques Mallet, Alain Simon, Francine Rendu. Smoking induces long-lasting effects through a monoamine-oxidase epigenetic regulation. PloS one. 2009 Nov; 4(11):e7959. doi: 10.1371/journal.pone.0007959. [PMID: 19956754]
  • Gustavo F Gonzales, Cynthia Gonzales-Castañeda. The Methyltetrahydro-{beta}-Carbolines in Maca (Lepidium meyenii). Evidence-based complementary and alternative medicine : eCAM. 2009 Sep; 6(3):315-6. doi: 10.1093/ecam/nen041. [PMID: 18955346]
  • Jia Chen, Xiao-Hui Yan, Jia-Hong Dong, Peng Sang, Xin Fang, Ying-Tong Di, Zhong-Kai Zhang, Xiao-Jiang Hao. Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn. Journal of agricultural and food chemistry. 2009 Aug; 57(15):6590-5. doi: 10.1021/jf901632j. [PMID: 19586051]
  • Xu-Jia Hu, Ying-Tong Di, Yue-Hu Wang, Ling-Yi Kong, Suo Gao, Chun-Shun Li, Hai-Yang Liu, Hong-Ping He, Jian Ding, Hua Xie, Xiao-Jiang Hao. Carboline alkaloids from Trigonostemon lii. Planta medica. 2009 Aug; 75(10):1157-61. doi: 10.1055/s-0029-1185505. [PMID: 19326327]
  • Akihisa Abe, Hiroyuki Yamada. Harmol induces apoptosis by caspase-8 activation independently of Fas/Fas ligand interaction in human lung carcinoma H596 cells. Anti-cancer drugs. 2009 Jun; 20(5):373-81. doi: 10.1097/cad.0b013e32832a2dd9. [PMID: 19318910]
  • Tayyab A Mansoor, Cátia Ramalhete, Joseph Molnár, Silva Mulhovo, Maria José U Ferreira. Tabernines A-C, beta-carbolines from the leaves of Tabernaemontana elegans. Journal of natural products. 2009 Jun; 72(6):1147-50. doi: 10.1021/np9001477. [PMID: 19473031]
  • Ji-Hyun Im, Yong-Ri Jin, Jung-Jin Lee, Ji-Yeon Yu, Xiang-Hua Han, Se-Hyuk Im, Jin Tae Hong, Hwan-Soo Yoo, Myoung-Yun Pyo, Yeo-Pyo Yun. Antiplatelet activity of beta-carboline alkaloids from Perganum harmala: a possible mechanism through inhibiting PLCgamma2 phosphorylation. Vascular pharmacology. 2009 May; 50(5-6):147-52. doi: 10.1016/j.vph.2008.11.008. [PMID: 19073282]
  • Ana Paula Salum Pires, Carolina Dizioli Rodrigues De Oliveira, Sidnei Moura, Felipe Augusto Dörr, Wagner Abreu E Silva, Mauricio Yonamine. Gas chromatographic analysis of dimethyltryptamine and beta-carboline alkaloids in ayahuasca, an Amazonian psychoactive plant beverage. Phytochemical analysis : PCA. 2009 Mar; 20(2):149-53. doi: 10.1002/pca.1110. [PMID: 19140116]
  • A Movafeghi, M Abedini, F Fathiazad, M Aliasgharpour, Y Omidi. Floral nectar composition of Peganum harmala L. Natural product research. 2009; 23(3):301-8. doi: 10.1080/14786410802076291. [PMID: 19235031]
  • Debra L Bemis, Jillian L Capodice, Manisha Desai, Aaron E Katz, Ralph Buttyan. beta-carboline alkaloid-enriched extract from the amazonian rain forest tree pao pereira suppresses prostate cancer cells. Journal of the Society for Integrative Oncology. 2009; 7(2):59-65. doi: ". [PMID: 19476740]
  • Najma Arshad, Karin Zitterl-Eglseer, Shahida Hasnain, Michael Hess. Effect of Peganum harmala or its beta-carboline alkaloids on certain antibiotic resistant strains of bacteria and protozoa from poultry. Phytotherapy research : PTR. 2008 Nov; 22(11):1533-8. doi: 10.1002/ptr.2528. [PMID: 18814210]
  • Cristiana Gambelunghe, Kyriaki Aroni, Riccardo Rossi, Luca Moretti, Mauro Bacci. Identification of N,N-dimethyltryptamine and beta-carbolines in psychotropic ayahuasca beverage. Biomedical chromatography : BMC. 2008 Oct; 22(10):1056-9. doi: 10.1002/bmc.1023. [PMID: 18506697]
  • Giampietro Frison, Donata Favretto, Flavio Zancanaro, Giorgio Fazzin, Santo Davide Ferrara. A case of beta-carboline alkaloid intoxication following ingestion of Peganum harmala seed extract. Forensic science international. 2008 Aug; 179(2-3):e37-43. doi: 10.1016/j.forsciint.2008.05.003. [PMID: 18603389]
  • Paramita Das, Deboleena Sarkar, Nitin Chattopadhyay. Photophysics of a beta-carboline based non-ionic probe in anionic and zwitterionic liposome membranes. Chemistry and physics of lipids. 2008 Jul; 154(1):38-45. doi: 10.1016/j.chemphyslip.2008.03.003. [PMID: 18381069]
  • Axel Teichert, Tilo Lübken, Jürgen Schmidt, Christine Kuhnt, Manfred Huth, Andrea Porzel, Ludger Wessjohann, Norbert Arnold. Determination of beta-carboline alkaloids in fruiting bodies of Hygrophorus spp. by liquid chromatography/electrospray ionisation tandem mass spectrometry. Phytochemical analysis : PCA. 2008 Jul; 19(4):335-41. doi: 10.1002/pca.1057. [PMID: 18401852]
  • Manel J Barbanoj, Jordi Riba, S Clos, S Giménez, E Grasa, S Romero. Daytime Ayahuasca administration modulates REM and slow-wave sleep in healthy volunteers. Psychopharmacology. 2008 Feb; 196(2):315-26. doi: 10.1007/s00213-007-0963-0. [PMID: 18030450]
  • Justin J Maresh, Lesley-Ann Giddings, Anne Friedrich, Elke A Loris, Santosh Panjikar, Bernhardt L Trout, Joachim Stöckigt, Baron Peters, Sarah E O'Connor. Strictosidine synthase: mechanism of a Pictet-Spengler catalyzing enzyme. Journal of the American Chemical Society. 2008 Jan; 130(2):710-23. doi: 10.1021/ja077190z. [PMID: 18081287]
  • G Randel, M Balzer, S Grupe, S Drusch, B Kaina, K-L Platt, K Schwarz. Degradation of heterocyclic aromatic amines in oil under storage and frying conditions and reduction of their mutagenic potential. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2007 Nov; 45(11):2245-53. doi: 10.1016/j.fct.2007.05.020. [PMID: 17619072]
  • Hiroyuki Kohno, Yukari Totsuka, Yumiko Yasui, Rikako Suzuki, Shigeyuki Sugie, Keiji Wakabayashi, Takuji Tanaka. Tumor-initiating potency of a novel heterocyclic amine, aminophenylnorharman in mouse colonic carcinogenesis model. International journal of cancer. 2007 Oct; 121(8):1659-64. doi: 10.1002/ijc.22864. [PMID: 17557291]
  • Axel Teichert, Jürgen Schmidt, Andrea Porzel, Norbert Arnold, Ludger Wessjohann. Brunneins A-C, beta-carboline alkaloids from Cortinarius brunneus. Journal of natural products. 2007 Sep; 70(9):1529-31. doi: 10.1021/np070259w. [PMID: 17854153]
  • Peter Bernhardt, Elizabeth McCoy, Sarah E O'Connor. Rapid identification of enzyme variants for reengineered alkaloid biosynthesis in periwinkle. Chemistry & biology. 2007 Aug; 14(8):888-97. doi: 10.1016/j.chembiol.2007.07.008. [PMID: 17719488]
  • A G Eshimbetov, T S Tulyaganov. Theoretical and UV spectral study of isomeric 1-(quinolinyl)-beta-carbolines conformations. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2007 Jul; 67(3-4):1139-43. doi: 10.1016/j.saa.2006.07.054. [PMID: 17010662]
  • Alexandros S Botsaris. Plants used traditionally to treat malaria in Brazil: the archives of Flora Medicinal. Journal of ethnobiology and ethnomedicine. 2007 May; 3(?):18. doi: 10.1186/1746-4269-3-18. [PMID: 17472740]
  • Alok Chakrabarty, Arabinda Mallick, Basudeb Haldar, Paramita Das, Nitin Chattopadhyay. Binding interaction of a biological photosensitizer with serum albumins: a biophysical study. Biomacromolecules. 2007 Mar; 8(3):920-7. doi: 10.1021/bm061084s. [PMID: 17315924]
  • Rena Nishigaki, Yukari Totsuka, Hiroyuki Kataoka, Hirohumi Ushiyama, Sumio Goto, Takayuki Akasu, Tetsushi Watanabe, Takashi Sugimura, Keiji Wakabayashi. Detection of aminophenylnorharman, a possible endogenous mutagenic and carcinogenic compound, in human urine samples. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2007 Jan; 16(1):151-6. doi: 10.1158/1055-9965.epi-06-0052. [PMID: 17220344]
  • Lili Zhou, Andrew A Hopkins, David V Huhman, Lloyd W Sumner. Efficient and sensitive method for quantitative analysis of alkaloids in hardinggrass (Phalaris aquatica L.). Journal of agricultural and food chemistry. 2006 Dec; 54(25):9287-91. doi: 10.1021/jf061819k. [PMID: 17147408]
  • D L Bemis, J L Capodice, P Gorroochurn, A E Katz, R Buttyan. Anti-prostate cancer activity of a beta-carboline alkaloid enriched extract from Rauwolfia vomitoria. International journal of oncology. 2006 Nov; 29(5):1065-73. doi: . [PMID: 17016636]
  • Julien Fiot, Souleymane Sanon, Nadine Azas, Valérie Mahiou, Olivia Jansen, Luc Angenot, Guy Balansard, Evelyne Ollivier. Phytochemical and pharmacological study of roots and leaves of Guiera senegalensis J.F. Gmel (Combretaceae). Journal of ethnopharmacology. 2006 Jun; 106(2):173-8. doi: 10.1016/j.jep.2005.12.030. [PMID: 16443341]