Harmaline (BioDeep_00000000129)

 

Secondary id: BioDeep_00000276200

natural product human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds


代谢物信息卡片


3H-Pyrido[3,4-b]indole, 4,9-dihydro-7-methoxy-1-methyl-

化学式: C13H14N2O (214.1106074)
中文名称: 骆驼蓬碱, 骆驼蓬灵
谱图信息: 最多检出来源 Viridiplantae(plant) 2.05%

分子结构信息

SMILES: CC1=C2C(=C3C=CC(=CC3=N2)OC)CCN1
InChI: InChI=1/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,14H,5-6H2,1-2H3

描述信息

Harmaline is a harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7 and has been reduced across the 3,4 bond. It has a role as a oneirogen. It derives from a hydride of a harman.
Harmaline is a natural product found in Passiflora pilosicorona, Passiflora boenderi, and other organisms with data available.
A beta-carboline alkaloid isolated from seeds of PEGANUM.
A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7 and has been reduced across the 3,4 bond.
Harmaline is found in fruits. Harmaline is an alkaloid from Passiflora incarnata (maypops
D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants
D004791 - Enzyme Inhibitors > D008996 - Monoamine Oxidase Inhibitors
Acquisition and generation of the data is financially supported in part by CREST/JST.
KEIO_ID H027; [MS2] KO008994
KEIO_ID H027

同义名列表

68 个代谢物同义名

3H-Pyrido[3,4-b]indole, 4,9-dihydro-7-methoxy-1-methyl-; 3H-Pyrido(3,4-b)indole, 4,9-dihydro-7-methoxy-1-methyl-; 7-METHOXY-1-METHYL-4,9-DIHYDRO-3H-PYRIDO(3,4-B)INDOLE; 4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido(3,4-b)indole; 3,4-Dihydro-7-methoxy-1-methyl-9H-pyrido[3,4-b]indole; 7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole; 4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole; 7-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole; 3,4-Dihydro-7-methoxy-1-methyl-9H-pyrid[3,4-b]indole; 3,4-Dihydro-7-methoxy-1-methyl-9-pyrido(3,4-b)indole; 3,4-Dihydro-7-methoxy-1-methyl-9-pyrid(3,4-b)indole; 3,4-Dihydro-7-methoxy-1-methyl-9-pyrid[3,4-b]indole; 7-Methoxy-1-methyl-4,9-dihydro-3H-beta-carboline #; 7-methoxy-1-methyl-3,4-dihydro-2h-beta-carboline; 7-Methoxy-1-methyl-4,9-dihydro-3H-beta-carboline; 7-Methoxy-1-methyl-2,9-dihydro-1H-beta-carboline; 1-Methyl-7-methoxy-3,4-dihydro-.beta.-carboline; 7-methoxy-1-methyl-3H,4H,9H-pyrido[3,4-b]indole; 1-Methyl-7-methoxy-3, 4-dihydro-beta -carboline; 1-Methyl-7-methoxy-3,4-dihydro- beta-carboline; 1-Methyl-7-methoxy-3,4-dihydro-beta -carboline; 7-methoxy-1-methyl-4,9-dihydro-3H-b-carboline; 1-Methyl-7-methoxy-3,4-dihydro-beta-carboline; 3,4-Dihydro-7-methoxy-1-methyl-beta-carboline; 7-Methoxy-1-methyl-4,9-dihydro-3H-?-carboline; 7-Methoxy-1-methyl-4,9-dihydro-3H-β-carboline; 7-methoxy-1-methyl-3,4-dihydrobeta-carboline; 3H-Pyrido[3, 4,9-dihydro-7-methoxy-1-methyl-; 3,4-Dihydro-7-methoxy-1-methyl-b-carboline; Harmalol methyl ether; 3, 4-Dihydroharmine; 3,4-Dihydroharmine; Prestwick1_000610; Prestwick2_000610; Prestwick0_000610; Harmine, dihydro-; HARMALINE [MART.]; Prestwick3_000610; Spectrum5_001452; HARMALINE [HSDB]; O-Methylharmalol; Spectrum3_000720; Spectrum4_000824; Spectrum2_000411; UNII-CN58I4TOET; Dihydro-Harmine; Dihydroharmine; HARMALINE [MI]; BPBio1_000572; Oprea1_112644; MEGxp0_001874; DivK1c_000950; KBio1_000950; ACon1_000019; 3,4-b]indole; KBio2_005917; KBio2_003349; KBio2_000781; KBio3_001759; IDI1_000950; CN58I4TOET; Harmidine; Harmaline; A1-00783; harmalin; Armalin; HARMALINE HYDROCHLORIDE DIHYDRATE; Harmaline



数据库引用编号

47 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(1)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

109 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

  • Eleanor White, Tom Kennedy, Simon Ruffell, Daniel Perkins, Jerome Sarris. Ayahuasca and Dimethyltryptamine Adverse Events and Toxicity Analysis: A Systematic Thematic Review. International journal of toxicology. 2024 May; 43(3):327-339. doi: 10.1177/10915818241230916. [PMID: 38363085]
  • Ayesha Khanum, Yamin Bibi, Ilham Khan, Ghazala Mustafa, Kotb A Attia, Arif Ahmed Mohammed, Seung Hwan Yang, Abdul Qayyum. Molecular docking of bioactive compounds extracted and purified from selected medicinal plant species against covid-19 proteins and in vitro evaluation. Scientific reports. 2024 02; 14(1):3736. doi: 10.1038/s41598-024-54470-6. [PMID: 38355953]
  • 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]
  • Ahmed H Abdelazim, Majed A Algarni, Atiah H Almalki. Innovative spectrofluorometric method for determination of harmaline and harmine in different matrices. Scientific reports. 2023 11; 13(1):19951. doi: 10.1038/s41598-023-46041-y. [PMID: 37968310]
  • Akram Hegazy, Sara H Mahmoud, Yaseen A M M Elshaier, Noura M Abo Shama, Nasr Fawzy Nasr, M A Ali, Assem Mohamed El-Shazly, Islam Mostafa, Ahmed Mostafa. Antiviral activities of plant-derived indole and β-carboline alkaloids against human and avian influenza viruses. Scientific reports. 2023 Jan; 13(1):1612. doi: 10.1038/s41598-023-27954-0. [PMID: 36709362]
  • Sakineh Alijanpour, Zahra Ghasemzadeh, Mohaddeseh Ebrahimi-Ghiri, Mohammad-Reza Zarrindast. Basolateral amygdala cannabinoid CB1 receptors mediate the antinociceptive activity of harmaline in adolescent male mice. Physiology & behavior. 2022 10; 254(?):113886. doi: 10.1016/j.physbeh.2022.113886. [PMID: 35718215]
  • Mohsen Rashidi, Elham Mahmoudian, Sepideh Mirzaei, Seyadeh Narges Mazloomi, Ali Bazi, Hossein Azadeh, Mobina Mozaffari. Harmaline downregulates angiogenesis markers and suppresses the growth of 4T1 breast cancer cells in vivo and in vitro. Chemico-biological interactions. 2022 Sep; 365(?):110087. doi: 10.1016/j.cbi.2022.110087. [PMID: 35963316]
  • Sara Álvarez-Rodríguez, David López-González, Manuel J Reigosa, Fabrizio Araniti, Adela M Sánchez-Moreiras. Ultrastructural and hormonal changes related to harmaline-induced treatment in Arabidopsis thaliana (L.) Heynh. root meristem. Plant physiology and biochemistry : PPB. 2022 May; 179(?):78-89. doi: 10.1016/j.plaphy.2022.03.022. [PMID: 35325658]
  • Mohammad Shabani, Reyhaneh Naderi. Phytohormone abscisic acid elicits positive effects on harmaline-induced cognitive and motor disturbances in a rat model of essential tremor. Brain and behavior. 2022 05; 12(5):e2564. doi: 10.1002/brb3.2564. [PMID: 35591769]
  • Beatriz Werneck Lopes Santos, Daniel Carneiro Moreira, Tatiana Karla Dos Santos Borges, Eloisa Dutra Caldas. Components of Banisteriopsis caapi, a Plant Used in the Preparation of the Psychoactive Ayahuasca, Induce Anti-Inflammatory Effects in Microglial Cells. Molecules (Basel, Switzerland). 2022 Apr; 27(8):. doi: 10.3390/molecules27082500. [PMID: 35458698]
  • You-Xu Wang, Ning Cao, Hui-Da Guan, Xue-Mei Cheng, Chang-Hong Wang. Heme peroxidases are responsible for the dehydrogenation and oxidation metabolism of harmaline into harmine. Chinese journal of natural medicines. 2022 Mar; 20(3):194-201. doi: 10.1016/s1875-5364(22)60151-1. [PMID: 35369963]
  • 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]
  • Rofida A Saleh, Tarek F Eissa, Dalaal M Abdallah, Muhammed A Saad, Hanan S El-Abhar. Peganum harmala enhanced GLP-1 and restored insulin signaling to alleviate AlCl3-induced Alzheimer-like pathology model. Scientific reports. 2021 06; 11(1):12040. doi: 10.1038/s41598-021-90545-4. [PMID: 34103557]
  • Negar Sadegh, Arash Asfaram, Hamedreza Javadian, Hedayat Haddadi, Ebrahim Sharifpour. Ultrasound-assisted solid phase microextraction-HPLC method based on Fe3O4@SiO2-NH2-molecularly imprinted polymer magnetic nano-sorbent for rapid and efficient extraction of harmaline from Peganum harmala extract. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2021 May; 1171(?):122640. doi: 10.1016/j.jchromb.2021.122640. [PMID: 33743514]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
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  • Laura Lewerenz, Tahani Hijazin, Sara Abouzeid, Robert Hänsch, Dirk Selmar. Pilot study on the uptake and modification of harmaline in acceptor plants: An innovative approach to visualize the interspecific transfer of natural products. Phytochemistry. 2020 Jun; 174(?):112362. doi: 10.1016/j.phytochem.2020.112362. [PMID: 32229335]
  • Silvia Biggi, Michael Pancher, Claudia Stincardini, Silvia Luotti, Tania Massignan, Andrea Dalle Vedove, Andrea Astolfi, Pamela Gatto, Graziano Lolli, Maria Letizia Barreca, Valentina Bonetto, Valentina Adami, Emiliano Biasini. Identification of compounds inhibiting prion replication and toxicity by removing PrPC from the cell surface. Journal of neurochemistry. 2020 01; 152(1):136-150. doi: 10.1111/jnc.14805. [PMID: 31264722]
  • 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]
  • Rita C Z Souza, Flávia S Zandonadi, Donizete P Freitas, Luís F F Tófoli, Alessandra Sussulini. Validation of an analytical method for the determination of the main ayahuasca active compounds and application to real ayahuasca samples from Brazil. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2019 Aug; 1124(?):197-203. doi: 10.1016/j.jchromb.2019.06.014. [PMID: 31220748]
  • Yan Zhang, Futao Liu, Hao Xiao, Xinyue Yao, Genxun Li, Seok Rye Choi, Karl Ploessl, Zhihao Zha, Lin Zhu, Hank F Kung. Fluorine-18 labeled diphenyl sulfide derivatives for imaging serotonin transporter (SERT) in the brain. Nuclear medicine and biology. 2018 11; 66(?):1-9. doi: 10.1016/j.nucmedbio.2018.06.008. [PMID: 30096380]
  • Paromita Bhattacharjee, Tapas Ghosh, Sarita Sarkar, Prateek Pandya, Kakali Bhadra. Binding affinity and in vitro cytotoxicity of harmaline targeting different motifs of nucleic acids: An ultimate drug designing approach. Journal of molecular recognition : JMR. 2018 04; 31(4):. doi: 10.1002/jmr.2687. [PMID: 29243872]
  • Sarita Sarkar, Kakali Bhadra. Therapeutic Role of Harmalol Targeting Nucleic Acids: Biophysical Perspective and in vitro Cytotoxicity. Mini reviews in medicinal chemistry. 2018; 18(19):1624-1639. doi: 10.2174/1389557518666171211164830. [PMID: 29231137]
  • Jose A Morales-García, Mario de la Fuente Revenga, Sandra Alonso-Gil, María Isabel Rodríguez-Franco, Amanda Feilding, Ana Perez-Castillo, Jordi Riba. The alkaloids of Banisteriopsis caapi, the plant source of the Amazonian hallucinogen Ayahuasca, stimulate adult neurogenesis in vitro. Scientific reports. 2017 07; 7(1):5309. doi: 10.1038/s41598-017-05407-9. [PMID: 28706205]
  • M A Tabari, M R Youssefi, A A Moghadamnia. Antitrichomonal activity of Peganum harmala alkaloid extract against trichomoniasis in pigeon (Columba livia domestica). British poultry science. 2017 Jun; 58(3):236-241. doi: 10.1080/00071668.2017.1280725. [PMID: 28084792]
  • Shuping Li, Liang Teng, Wei Liu, Xuemei Cheng, Bo Jiang, Zhengtao Wang, Changhong Wang. Interspecies metabolic diversity of harmaline and harmine in in vitro 11 mammalian liver microsomes. Drug testing and analysis. 2017 May; 9(5):754-768. doi: 10.1002/dta.2028. [PMID: 27377954]
  • 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]
  • Hina Siddiqui, Sehar Tasneem, Saba Farooq, Amtul Sami, Atta-Ur Rahman, Muhammad I Choudhary. Harmaline and its Derivatives Against the Infectious Multi-Drug Resistant Escherichia coli. Medicinal chemistry (Shariqah (United Arab Emirates)). 2017; 13(5):465-476. doi: 10.2174/1573406413666170125113832. [PMID: 28124613]
  • Xiaofei Shang, Xiao Guo, Bing Li, Hu Pan, Jiyu Zhang, Yu Zhang, Xiaolou Miao. Microwave-assisted extraction of three bioactive alkaloids from Peganum harmala L. and their acaricidal activity against Psoroptes cuniculi in vitro. Journal of ethnopharmacology. 2016 Nov; 192(?):350-361. doi: 10.1016/j.jep.2016.07.057. [PMID: 27452655]
  • Elzalina R Soares, Felipe M A da Silva, Richardson A de Almeida, Bruna R de Lima, Francinaldo A da Silva Filho, Andersson Barison, Hector H F Koolen, Maria Lúcia B Pinheiro, Afonso D L de Souza. Direct infusion ESI-IT-MSn alkaloid profile and isolation of tetrahydroharman and other alkaloids from Bocageopsis pleiosperma maas (Annonaceae). Phytochemical analysis : PCA. 2015 Sep; 26(5):339-45. doi: 10.1002/pca.2568. [PMID: 26108161]
  • Fabienne Gourand, Nahid Amini, Zhisheng Jia, Sharon Stone-Elander, Denis Guilloteau, Louisa Barré, Christer Halldin. [11C]MADAM Used as a Model for Understanding the Radiometabolism of Diphenyl Sulfide Radioligands for Positron Emission Tomography (PET). PloS one. 2015; 10(9):e0137160. doi: 10.1371/journal.pone.0137160. [PMID: 26367261]
  • Chunnuan Deng, Hua Shao, Xiangliang Pan, Shuzhi Wang, Daoyong Zhang. Herbicidal effects of harmaline from Peganum harmala on photosynthesis of Chlorella pyrenoidosa: probed by chlorophyll fluorescence and thermoluminescence. Pesticide biochemistry and physiology. 2014 Oct; 115(?):23-31. doi: 10.1016/j.pestbp.2014.08.002. [PMID: 25307462]
  • Sudhakar Manda, Shabana I Khan, Surendra K Jain, Shabber Mohammed, Babu L Tekwani, Ikhlas A Khan, Ram A Vishwakarma, Sandip B Bharate. Synthesis, antileishmanial and antitrypanosomal activities of N-substituted tetrahydro-β-carbolines. Bioorganic & medicinal chemistry letters. 2014 Aug; 24(15):3247-50. doi: 10.1016/j.bmcl.2014.06.030. [PMID: 24980054]
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  • Lei Zhang, Liang Teng, Can Gong, Wei Liu, Xuemei Cheng, Shenghua Gu, Zhongping Deng, Zhengtao Wang, Changhong Wang. Simultaneous determination of harmine, harmaline and their metabolites harmol and harmalol in beagle dog plasma by UPLC-ESI-MS/MS and its application to a pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2013 Nov; 85(?):162-8. doi: 10.1016/j.jpba.2013.07.019. [PMID: 23948761]
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  • Nashwa Jarkas. Fluorinated diaryl sulfides. Current topics in medicinal chemistry. 2013; 13(8):936-43. doi: 10.2174/1568026611313080006. [PMID: 23590166]
  • Ting Zhao, Shan-Song Zheng, Bin-Feng Zhang, Yuan-Yuan Li, S W Annie Bligh, Chang-Hong Wang, Zheng-Tao Wang. Metabolic pathways of the psychotropic-carboline alkaloids, harmaline and harmine, by liquid chromatography/mass spectrometry and NMR spectroscopy. Food chemistry. 2012 Sep; 134(2):1096-105. doi: 10.1016/j.foodchem.2012.03.024. [PMID: 23107733]
  • Bharathi Avula, Yan-Hong Wang, Chidananda Swamy Rumalla, Troy J Smillie, Ikhlas A Khan. Simultaneous determination of alkaloids and flavonoids from aerial parts of Passiflora species and dietary supplements using UPLC-UV-MS and HPTLC. Natural product communications. 2012 Sep; 7(9):1177-80. doi: . [PMID: 23074901]
  • Bahram Hemmateenejad, Mojtaba Shamsipur, Fayezeh Samari, Taghi Khayamian, Malihe Ebrahimi, Zahra Rezaei. Combined fluorescence spectroscopy and molecular modeling studies on the interaction between harmalol and human serum albumin. Journal of pharmaceutical and biomedical analysis. 2012 Aug; 67-68(?):201-8. doi: 10.1016/j.jpba.2012.04.012. [PMID: 22560122]
  • Jordi Riba, Ethan H McIlhenny, Marta Valle, José Carlos Bouso, Steven A Barker. Metabolism and disposition of N,N-dimethyltryptamine and harmala alkaloids after oral administration of ayahuasca. Drug testing and analysis. 2012 Jul; 4(7-8):610-6. doi: 10.1002/dta.1344. [PMID: 22514127]
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  • Muhammad Rizwan-ul-Haq, Liang Gong, Meiying Hu, Jianjun Luo. Apolipophorin III and transmission electron microscopy as toxicity indicators for harmaline and tea saponin in Spodoptera exigua (Noctuidae: Lepidoptera). Chemosphere. 2011 Oct; 85(6):995-1001. doi: 10.1016/j.chemosphere.2011.06.089. [PMID: 21783224]
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