Aribin (BioDeep_00000865256)

Main id: BioDeep_00000000032

 

PANOMIX_OTCML-2023


代谢物信息卡片


InChI=1\C12H10N2\c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12\h2-7,14H,1H

化学式: C12H10N2 (182.0844)
中文名称: 哈尔满碱
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=NC=CC2=C1NC3=C2C=CC=C3
InChI: InChI=1S/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3

描述信息

D009676 - Noxae > D009498 - Neurotoxins
D009676 - Noxae > D009153 - Mutagens
Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].
Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].
Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].

同义名列表

71 个代谢物同义名

InChI=1\C12H10N2\c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12\h2-7,14H,1H; 5-23-08-00261 (Beilstein Handbook Reference); 9H-Pyrido(3,4-b)indole, 1-methyl-; 9H-Pyrido[3,4-b]indole, 1-methyl-; 1-Methyl-9H-pyrido(3,4-b)indole; 1-Methyl-9H-pyrido[3,4-b]indole; 1-Methyl-9H-pyrid[3,4-b]indole; 1-Methyl-9H-beta-carboline; 1-Methyl-.beta.-carboline; 1-methyl-9H-$b-carboline; PYRIDOBINDOLE, L-METHYL-; 2-Methyl-beta-carboline; SDCCGMLS-0066938.P001; 486-84-0 (FREE BASE); WLN: T B656 EN HMJ F; 3-Methyl-4-carboline; Prestwick3_000620; 1-Methylnorharman; Prestwick2_000620; Prestwick1_000620; Prestwick0_000620; EINECS 207-642-2; Spectrum3_000905; 21655-84-5 (HCL); Spectrum4_001003; SpecPlus_000609; NCGC00025022-06; NCGC00025022-03; SPECTRUM1500866; NCGC00025022-01; Spectrum_001126; NCGC00015514-01; NCGC00015514-02; CAS-21655-84-5; 103276_ALDRICH; BSPBio_000560; Lopac0_000605; DivK1c_006705; KBioSS_001606; KBioGR_001465; BPBio1_000616; Oprea1_152883; SPBio_002779; KBio3_001850; KBio2_001606; KBio1_001649; KBio2_004174; ZINC00120172; Lopac-H-7258; KBio2_006742; 51370_FLUKA; AIDS-109048; Passiflorin; BRN 0143898; Tocris-1132; CCRIS 6419; AIDS109048; EU-0100605; Locuturine; NSC 54439; SBB003735; Locuturin; Loturine; NSC54439; 486-84-0; Aribine; Harmane; Aribin; C09209; Harman; Harman



数据库引用编号

14 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)

79 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。

亚细胞结构定位 关联基因列表
Cytoplasm 7 ADIG, CA1, CA3, MAPK14, PRKAA2, SIRT1, SLC6A3
Peripheral membrane protein 2 ACHE, CYP1B1
Endoplasmic reticulum membrane 2 CYP1B1, DRD1
Mitochondrion membrane 1 MAOA
Nucleus 7 ACHE, ADIG, DRD1, MAPK14, MPO, PRKAA2, SIRT1
cytosol 6 CA1, CA3, MAOA, MAPK14, PRKAA2, SIRT1
dendrite 4 DRD2, HTR2A, MAOB, PRKAA2
nucleoplasm 4 MAPK14, MPO, PRKAA2, SIRT1
Cell membrane 5 ACHE, DRD1, DRD2, HTR2A, SLC6A3
Cytoplasmic side 2 MAOA, MAOB
Cell projection, axon 2 HTR2A, SLC6A3
Multi-pass membrane protein 6 CACNA1I, DRD1, DRD2, HTR2A, RYR2, SLC6A3
Golgi apparatus membrane 1 DRD2
Synapse 2 ACHE, DRD2
cell surface 2 ACHE, SLC6A3
dendritic shaft 1 HTR2A
glutamatergic synapse 4 DRD1, DRD2, HTR2A, MAPK14
Golgi apparatus 2 ACHE, PRKAA2
Golgi membrane 2 DRD2, INS
neuromuscular junction 1 ACHE
neuronal cell body 4 HTR2A, MAOB, PRKAA2, SLC6A3
presynaptic membrane 4 DRD1, DRD2, HTR2A, SLC6A3
sarcolemma 1 RYR2
smooth endoplasmic reticulum 1 RYR2
Lysosome 1 MPO
Presynapse 1 HTR2A
acrosomal vesicle 1 DRD2
plasma membrane 9 ACHE, BCHE, CACNA1I, DRD1, DRD2, F2, HTR2A, RYR2, SLC6A3
synaptic vesicle membrane 1 DRD2
Membrane 8 ACHE, ADIG, CACNA1I, CYP1B1, MAOA, PRKAA2, RYR2, SLC6A3
axon 4 DRD2, HTR2A, PRKAA2, SLC6A3
caveola 1 HTR2A
extracellular exosome 3 CA1, F2, MPO
extracellular space 5 ACHE, BCHE, F2, INS, MPO
perinuclear region of cytoplasm 1 ACHE
mitochondrion 5 CYP1B1, MAOA, MAOB, MAPK14, SIRT1
protein-containing complex 1 RYR2
intracellular membrane-bounded organelle 2 CYP1B1, MPO
Microsome membrane 1 CYP1B1
chromatin silencing complex 1 SIRT1
Secreted 5 ACHE, ADIG, BCHE, F2, INS
extracellular region 7 ACHE, ADIG, BCHE, F2, INS, MAPK14, MPO
Mitochondrion outer membrane 2 MAOA, MAOB
Single-pass membrane protein 2 ADIG, MAOA
mitochondrial outer membrane 2 MAOA, MAOB
neuronal cell body membrane 1 SLC6A3
Extracellular side 1 ACHE
ciliary membrane 2 DRD1, DRD2
dendritic spine 2 DRD1, DRD2
perikaryon 1 DRD2
Z disc 1 RYR2
cytoplasmic vesicle 1 HTR2A
nucleolus 1 SIRT1
postsynaptic membrane 4 DRD1, DRD2, HTR2A, SLC6A3
heterochromatin 1 SIRT1
Membrane raft 1 SLC6A3
GABA-ergic synapse 2 DRD1, DRD2
flotillin complex 1 SLC6A3
basement membrane 1 ACHE
sarcoplasmic reticulum 1 RYR2
Cell projection, dendritic spine 1 DRD1
Nucleus, PML body 1 SIRT1
PML body 1 SIRT1
collagen-containing extracellular matrix 1 F2
secretory granule 1 MPO
lateral plasma membrane 1 DRD2
nuclear speck 2 MAPK14, PRKAA2
nuclear inner membrane 1 SIRT1
Cell projection, neuron projection 1 SLC6A3
neuron projection 1 SLC6A3
cilium 2 DRD1, DRD2
chromatin 1 SIRT1
spindle pole 1 MAPK14
blood microparticle 2 BCHE, F2
non-motile cilium 2 DRD1, DRD2
Lipid-anchor, GPI-anchor 1 ACHE
sperm flagellum 1 DRD2
fibrillar center 1 SIRT1
nuclear envelope 1 SIRT1
endosome lumen 1 INS
Lipid droplet 1 ADIG
Membrane, caveola 1 HTR2A
cell body fiber 1 HTR2A
Cell projection, dendrite 2 DRD1, HTR2A
cytoplasmic stress granule 1 PRKAA2
euchromatin 1 SIRT1
side of membrane 1 ACHE
azurophil granule 1 MPO
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 2 INS, MAPK14
Golgi lumen 2 F2, INS
endoplasmic reticulum lumen 3 BCHE, F2, INS
axon terminus 2 DRD2, SLC6A3
voltage-gated calcium channel complex 1 CACNA1I
endocytic vesicle 1 DRD2
transport vesicle 1 INS
azurophil granule lumen 1 MPO
Sarcoplasmic reticulum membrane 1 RYR2
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
mitochondrial envelope 1 MAOB
Single-pass type IV membrane protein 2 MAOA, MAOB
nuclear envelope lumen 1 BCHE
neurofilament 1 HTR2A
calcium channel complex 1 RYR2
junctional sarcoplasmic reticulum membrane 1 RYR2
phagocytic vesicle lumen 1 MPO
synaptic cleft 1 ACHE
eNoSc complex 1 SIRT1
rDNA heterochromatin 1 SIRT1
dopaminergic synapse 2 DRD2, SLC6A3
nucleotide-activated protein kinase complex 1 PRKAA2
Cell projection, cilium membrane 1 DRD1
G protein-coupled receptor complex 2 DRD1, DRD2
[Isoform H]: Cell membrane 1 ACHE
G protein-coupled serotonin receptor complex 1 HTR2A
[SirtT1 75 kDa fragment]: Cytoplasm 1 SIRT1


文献列表

  • Bao Tan Nguyen, Nguyen Thi Hai Yen, Ninh Khac Thanh Tung, Gil-Saeng Jeong, Jong Seong Kang, Nguyen Phuoc Long, Hyung Min Kim. Lipid class-dependent alterations of Caenorhabditis elegans under harmane exposure. Journal of pharmaceutical and biomedical analysis. 2023 Jul; 231(?):115401. doi: 10.1016/j.jpba.2023.115401. [PMID: 37105045]
  • Soching Luikham, Mavani A, Jhimli Bhattacharyya. Deciphering binding affinity, energetics, and base specificity of plant alkaloid Harmane with AT and GC hairpin duplex DNA. Luminescence : the journal of biological and chemical luminescence. 2022 May; 37(5):691-701. doi: 10.1002/bio.4210. [PMID: 35156295]
  • 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]
  • 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]
  • Vivek Lawana, Se Young Um, Rachel M Foguth, Jason R Cannon. Neuromelanin formation exacerbates HAA-induced mitochondrial toxicity and mitophagy impairments. Neurotoxicology. 2020 12; 81(?):147-160. doi: 10.1016/j.neuro.2020.10.005. [PMID: 33058929]
  • 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]
  • 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]
  • 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]
  • Haroon Khan, Seema Patel, Mohammad A Kamal. Pharmacological and Toxicological Profile of Harmane-β-Carboline Alkaloid: Friend or Foe. Current drug metabolism. 2017; 18(9):853-857. doi: 10.2174/1389200218666170607100947. [PMID: 28595532]
  • Shuping Li, Liang Teng, Wei Liu, Xuemei Cheng, Bo Jiang, Zhengtao Wang, Chang-Hong Wang. Pharmacokinetic study of harmane and its 10 metabolites in rat after intravenous and oral administration by UPLC-ESI-MS/MS. Pharmaceutical biology. 2016 Sep; 54(9):1768-81. doi: 10.3109/13880209.2015.1127978. [PMID: 26730489]
  • 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]
  • 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]
  • Shuping Li, Wei Liu, Liang Teng, Xuemei Cheng, Zhengtao Wang, Changhong Wang. Metabolites identification of harmane in vitro/in vivo in rats by ultra-performance liquid chromatography combined with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2014 Apr; 92(?):53-62. doi: 10.1016/j.jpba.2014.01.003. [PMID: 24486683]
  • 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]
  • Karen L Smith, Gemma K Ford, David S Jessop, David P Finn. Behavioural, neurochemical and neuroendocrine effects of the endogenous β-carboline harmane in fear-conditioned rats. Journal of psychopharmacology (Oxford, England). 2013 Feb; 27(2):162-70. doi: 10.1177/0269881112460108. [PMID: 23015542]
  • Mohammad Nasehi, Morteza Piri, Mojgan Abdollahian, Mohammad Reza Zarrindast. Involvement of nitrergic system of CA1in harmane induced learning and memory deficits. Physiology & behavior. 2013 Jan; 109(?):23-32. doi: 10.1016/j.physbeh.2012.10.006. [PMID: 23103833]
  • G- B Zhang, B Zhang, X- X Zhang, F- H Bing. Homonojirimycin, an alkaloid from dayflower inhibits the growth of influenza A virus in vitro. Acta virologica. 2013; 57(1):85-6. doi: 10.4149/av_2013_01_85. [PMID: 23530829]
  • Arkadiusz Szterk, Marek Roszko, Krystian Małek, Marcin Kurek, Monika Zbieć, Bożena Waszkiewicz-Robak. Profiles and concentrations of heterocyclic aromatic amines formed in beef during various heat treatments depend on the time of ripening and muscle type. Meat science. 2012 Dec; 92(4):587-95. doi: 10.1016/j.meatsci.2012.06.004. [PMID: 22762996]
  • 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]
  • 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]
  • Mohammad Nasehi, Shahrbano Sharifi, Mohammad Reza Zarrindast. Involvement of the cholinergic system of CA1 on harmane-induced amnesia in the step-down passive avoidance test. Journal of psychopharmacology (Oxford, England). 2012 Aug; 26(8):1151-61. doi: 10.1177/0269881111421972. [PMID: 21965190]
  • Bijan Kumar Paul, Nikhil Guchhait. Differential interactions of a biological photosensitizer with liposome membranes having varying surface charges. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology. 2012 Apr; 11(4):661-73. doi: 10.1039/c2pp05346b. [PMID: 22266915]
  • Eric G Mworia, Takashi Yoshikawa, Nadiah Salikon, Chisato Oda, William O Asiche, Naoki Yokotani, Daigo Abe, Koichiro Ushijima, Ryohei Nakano, Yasutaka Kubo. Low-temperature-modulated fruit ripening is independent of ethylene in 'Sanuki Gold' kiwifruit. Journal of experimental botany. 2012 Jan; 63(2):963-71. doi: 10.1093/jxb/err324. [PMID: 22058408]
  • Jian-Hui Xiao, Dai-Min Xiao, Dai-Xiong Chen, Yu Xiao, Zong-Qi Liang, Jian-Jiang Zhong. Polysaccharides from the Medicinal Mushroom Cordyceps taii Show Antioxidant and Immunoenhancing Activities in a D-Galactose-Induced Aging Mouse Model. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):273435. doi: 10.1155/2012/273435. [PMID: 22536281]
  • Xing-Tai Li, Ya-Kui Zhang, Hai-Xue Kuang, Feng-Xin Jin, De-Wen Liu, Ming-Bo Gao, Ze Liu, Xiao-Juan Xin. Mitochondrial protection and anti-aging activity of Astragalus polysaccharides and their potential mechanism. International journal of molecular sciences. 2012; 13(2):1747-1761. doi: 10.3390/ijms13021747. [PMID: 22408421]
  • Nicole Shangming Hou, Stefan Taubert. Function and Regulation of Lipid Biology in Caenorhabditis elegans Aging. Frontiers in physiology. 2012; 3(?):143. doi: 10.3389/fphys.2012.00143. [PMID: 22629250]
  • Janick Mathys, Kaat De Cremer, Pieter Timmermans, Stefan Van Kerckhove, Bart Lievens, Mieke Vanhaecke, Bruno P A Cammue, Barbara De Coninck. Genome-Wide Characterization of ISR Induced in Arabidopsis thaliana by Trichoderma hamatum T382 Against Botrytis cinerea Infection. Frontiers in plant science. 2012; 3(?):108. doi: 10.3389/fpls.2012.00108. [PMID: 22661981]
  • Steven Maranz. An alternative paradigm for the role of antimalarial plants in Africa. TheScientificWorldJournal. 2012; 2012(?):978913. doi: 10.1100/2012/978913. [PMID: 22593717]
  • Mat Ropi Muktar, Norfaizah Osman, Khalijah Awang, Hazrina Hazni, Ahmad Kaleem Qureshi, A Hamid A Hadi, Kazuma Zaima, Hiroshi Morita, Marc Litaudon. Neonaucline, a new indole alkaloid from the leaves of Ochreinauclea maingayii (Hook. f.) Ridsd. (Rubiaceae). Molecules (Basel, Switzerland). 2011 Dec; 17(1):267-74. doi: 10.3390/molecules17010267. [PMID: 22205092]
  • Ting Zhao, Yu-qi He, Jun Wang, Ke-min Ding, Chang-hong Wang, Zheng-tao Wang. Inhibition of human cytochrome P450 enzymes 3A4 and 2D6 by β-carboline alkaloids, harmine derivatives. Phytotherapy research : PTR. 2011 Nov; 25(11):1671-7. doi: 10.1002/ptr.3458. [PMID: 21433154]
  • Emily B Merewitz, Thomas Gianfagna, Bingru Huang. Protein accumulation in leaves and roots associated with improved drought tolerance in creeping bentgrass expressing an ipt gene for cytokinin synthesis. Journal of experimental botany. 2011 Nov; 62(15):5311-33. doi: 10.1093/jxb/err166. [PMID: 21831843]
  • Marcelo F de Araújo, Ivo J Curcino Vieira, Raimundo Braz-Filho, Mário G de Carvalho. Simiranes A and B: erythroxylanes diterpenes and other compounds from Simira eliezeriana (Rubiaceae). Natural product research. 2011 Oct; 25(18):1713-9. doi: 10.1080/14786419.2011.560575. [PMID: 21936665]
  • Bijan Kumar Paul, Nikhil Guchhait. Modulation of prototropic activity and rotational relaxation dynamics of a cationic biological photosensitizer within the motionally constrained bio-environment of a protein. The journal of physical chemistry. B. 2011 Sep; 115(34):10322-34. doi: 10.1021/jp2015275. [PMID: 21790166]
  • Hedi Ben Mansour, Sonia Yatouji, Sihem Mbarek, Ikram Houas, Afef Delai, Dorra Dridi. Correlation between antibutyrylcholinesterasic and antioxidant activities of three aqueous extracts from Tunisian Rhus pentaphyllum. Annals of clinical microbiology and antimicrobials. 2011 Aug; 10(?):32. doi: 10.1186/1476-0711-10-32. [PMID: 21880140]
  • 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]
  • Ingrid Bacher, Sylvain Houle, Xin Xu, Laurie Zawertailo, Alexandra Soliman, Alan A Wilson, Peter Selby, Tony P George, Julia Sacher, Laura Miler, Stephen J Kish, Pablo Rusjan, Jeffrey H Meyer. Monoamine oxidase A binding in the prefrontal and anterior cingulate cortices during acute withdrawal from heavy cigarette smoking. Archives of general psychiatry. 2011 Aug; 68(8):817-26. doi: 10.1001/archgenpsychiatry.2011.82. [PMID: 21810646]
  • Lidia Błaszczyk, Delfina Popiel, Jerzy Chełkowski, Grzegorz Koczyk, Gary J Samuels, Krzysztof Sobieralski, Marek Siwulski. Species diversity of Trichoderma in Poland. Journal of applied genetics. 2011 May; 52(2):233-43. doi: 10.1007/s13353-011-0039-z. [PMID: 21465156]
  • Nady Braidy, Gilles J Guillemin, Hussein Mansour, Tailoi Chan-Ling, Anne Poljak, Ross Grant. Age related changes in NAD+ metabolism oxidative stress and Sirt1 activity in wistar rats. PloS one. 2011 Apr; 6(4):e19194. doi: 10.1371/journal.pone.0019194. [PMID: 21541336]
  • 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]
  • 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]
  • A Daniel Martin, Barbara K Smith, Paul D Davenport, Eloise Harman, Ricardo J Gonzalez-Rothi, Maher Baz, A Joseph Layon, Michael J Banner, Lawrence J Caruso, Harsha Deoghare, Tseng-Tien Huang, Andrea Gabrielli. Inspiratory muscle strength training improves weaning outcome in failure to wean patients: a randomized trial. Critical care (London, England). 2011; 15(2):R84. doi: 10.1186/cc10081. [PMID: 21385346]
  • Stephen S Leonard, Bean T Chen, Samuel G Stone, Diane Schwegler-Berry, Allison J Kenyon, David Frazer, James M Antonini. Comparison of stainless and mild steel welding fumes in generation of reactive oxygen species. Particle and fibre toxicology. 2010 Nov; 7(?):32. doi: 10.1186/1743-8977-7-32. [PMID: 21047424]
  • Andrés R Schwember, Kent J Bradford. Quantitative trait loci associated with longevity of lettuce seeds under conventional and controlled deterioration storage conditions. Journal of experimental botany. 2010 Oct; 61(15):4423-36. doi: 10.1093/jxb/erq248. [PMID: 20693410]
  • 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]
  • Monika Gibis, Jochen Weiss. Inhibitory effect of marinades with hibiscus extract on formation of heterocyclic aromatic amines and sensory quality of fried beef patties. Meat science. 2010 Aug; 85(4):735-42. doi: 10.1016/j.meatsci.2010.03.034. [PMID: 20418021]
  • Kim Ekroos, Minna Jänis, Kirill Tarasov, Reini Hurme, Reijo Laaksonen. Lipidomics: a tool for studies of atherosclerosis. Current atherosclerosis reports. 2010 Jul; 12(4):273-81. doi: 10.1007/s11883-010-0110-y. [PMID: 20425241]
  • Toru Sasaki, Keiko Unno, Shoichi Tahara, Takao Kaneko. Age-related increase of reactive oxygen generation in the brains of mammals and birds: is reactive oxygen a signaling molecule to determine the aging process and life span?. Geriatrics & gerontology international. 2010 Jul; 10 Suppl 1(?):S10-24. doi: 10.1111/j.1447-0594.2010.00601.x. [PMID: 20590825]
  • Michal Shoresh, Gary E Harman. Differential expression of maize chitinases in the presence or absence of Trichoderma harzianum strain T22 and indications of a novel exo- endo-heterodimeric chitinase activity. BMC plant biology. 2010 Jul; 10(?):136. doi: 10.1186/1471-2229-10-136. [PMID: 20594307]
  • Mohammad Nasehi, Morteza Piri, Maryam Nouri, Davood Farzin, Touraj Nayer-Nouri, Mohammad Reza Zarrindast. Involvement of dopamine D1/D2 receptors on harmane-induced amnesia in the step-down passive avoidance test. European journal of pharmacology. 2010 May; 634(1-3):77-83. doi: 10.1016/j.ejphar.2010.02.027. [PMID: 20188725]
  • Makoto Suzuki, D Craig Willcox, Matthew W Rosenbaum, Bradley J Willcox. Oxidative stress and longevity in okinawa: an investigation of blood lipid peroxidation and tocopherol in okinawan centenarians. Current gerontology and geriatrics research. 2010; 2010(?):380460. doi: 10.1155/2010/380460. [PMID: 21490698]
  • Kanti Bhooshan Pandey, Syed Ibrahim Rizvi. Markers of oxidative stress in erythrocytes and plasma during aging in humans. Oxidative medicine and cellular longevity. 2010 Jan; 3(1):2-12. doi: 10.4161/oxim.3.1.10476. [PMID: 20716923]
  • Michela Guglielmotto, Luca Giliberto, Elena Tamagno, Massimo Tabaton. Oxidative stress mediates the pathogenic effect of different Alzheimer's disease risk factors. Frontiers in aging neuroscience. 2010; 2(?):3. doi: 10.3389/neuro.24.003.2010. [PMID: 20552043]
  • Toru Sasaki. [Analysis of aging-related oxidative stress status in normal aging animals and development of anti-aging interventions]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2010 Jan; 130(1):29-42. doi: 10.1248/yakushi.130.29. [PMID: 20046062]
  • Ana Navarro, Alberto Boveris. Brain mitochondrial dysfunction in aging, neurodegeneration, and Parkinson's disease. Frontiers in aging neuroscience. 2010; 2(?):. doi: 10.3389/fnagi.2010.00034. [PMID: 20890446]
  • Saveetha Kandasamy, Karthiba Loganathan, Raveendran Muthuraj, Saravanakumar Duraisamy, Suresh Seetharaman, Raguchander Thiruvengadam, Balasubramanian Ponnusamy, Samiyappan Ramasamy. Understanding the molecular basis of plant growth promotional effect of Pseudomonas fluorescens on rice through protein profiling. Proteome science. 2009 Dec; 7(?):47. doi: 10.1186/1477-5956-7-47. [PMID: 20034395]
  • Thore C Brink, Christian Regenbrecht, Lloyd Demetrius, Hans Lehrach, James Adjaye. Activation of the immune response is a key feature of aging in mice. Biogerontology. 2009 Dec; 10(6):721-34. doi: 10.1007/s10522-009-9219-1. [PMID: 19255868]
  • Ahmet Korkmaz, Sukru Oter, Melik Seyrek, Turgut Topal. Molecular, genetic and epigenetic pathways of peroxynitrite-induced cellular toxicity. Interdisciplinary toxicology. 2009 Dec; 2(4):219-28. doi: 10.2478/v10102-009-0020-4. [PMID: 21217858]
  • 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]
  • Liaoyuan A Hu, Tian Zhou, Jinwoo Ahn, Shuli Wang, Julia Zhou, Yi Hu, Qingyun Liu. Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands. The Biochemical journal. 2009 Oct; 424(1):39-45. doi: 10.1042/bj20090998. [PMID: 19725810]
  • Thore C Brink, Lloyd Demetrius, Hans Lehrach, James Adjaye. Age-related transcriptional changes in gene expression in different organs of mice support the metabolic stability theory of aging. Biogerontology. 2009 Oct; 10(5):549-64. doi: 10.1007/s10522-008-9197-8. [PMID: 19031007]
  • Xi-yuan Zheng, Zi-jia Zhang, Gui-xin Chou, Tao Wu, Xue-mei Cheng, Chang-hong Wang, Zheng-tao Wang. Acetylcholinesterase inhibitive activity-guided isolation of two new alkaloids from seeds of Peganum nigellastrum Bunge by an in vitro TLC- bioautographic assay. Archives of pharmacal research. 2009 Sep; 32(9):1245-51. doi: 10.1007/s12272-009-1910-x. [PMID: 19784581]
  • 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]
  • Noriko Sakano, Da-Hong Wang, Noriko Takahashi, Bingling Wang, Rani Sauriasari, Sakiko Kanbara, Yoshie Sato, Tomoko Takigawa, Jiro Takaki, Keiki Ogino. Oxidative stress biomarkers and lifestyles in Japanese healthy people. Journal of clinical biochemistry and nutrition. 2009 Mar; 44(2):185-95. doi: 10.3164/jcbn.08-252. [PMID: 19308273]
  • 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]
  • Wen-bo Xin, Ping Gu, Gui-xin Chou, Zheng-tao Wang. [Studies on alkalodial constituents in leaves of Uncaria hirsuta]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Sep; 33(17):2124-8. doi: . [PMID: 19066056]
  • Keiichi Enjyoji, Ko Kotani, Chandrashekar Thukral, Benjamin Blumel, Xiaofeng Sun, Yan Wu, Masato Imai, David Friedman, Eva Csizmadia, Wissam Bleibel, Barbara B Kahn, Simon C Robson. Deletion of cd39/entpd1 results in hepatic insulin resistance. Diabetes. 2008 Sep; 57(9):2311-20. doi: 10.2337/db07-1265. [PMID: 18567823]
  • 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]
  • Songlin Li, Quanbin Han, Chunfeng Qiao, Jingzheng Song, Chuen Lung Cheng, Hongxi Xu. Chemical markers for the quality control of herbal medicines: an overview. Chinese medicine. 2008 Jun; 3(?):7. doi: 10.1186/1749-8546-3-7. [PMID: 18588699]
  • Udo Bonnet, Norbert Scherbaum, Martin Wiemann. The endogenous alkaloid harmane: acidifying and activity-reducing effects on hippocampal neurons in vitro. Progress in neuro-psychopharmacology & biological psychiatry. 2008 Feb; 32(2):362-7. doi: 10.1016/j.pnpbp.2007.08.043. [PMID: 17904720]
  • Lesley Rees. What parathyroid hormone levels should we aim for in children with stage 5 chronic kidney disease; what is the evidence?. Pediatric nephrology (Berlin, Germany). 2008 Feb; 23(2):179-84. doi: 10.1007/s00467-007-0684-y. [PMID: 18043947]
  • Xue-ren Yin, Kun-song Chen, Andrew C Allan, Rong-mei Wu, Bo Zhang, Nagin Lallu, Ian B Ferguson. Ethylene-induced modulation of genes associated with the ethylene signalling pathway in ripening kiwifruit. Journal of experimental botany. 2008; 59(8):2097-108. doi: 10.1093/jxb/ern067. [PMID: 18535296]
  • 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]
  • Li Li, Susanne N Boehn, Xiaolei Yu, Qingqin Zhang, Marc Kenzelmann, Dieter Techel, Salah A Mohamed, Petra Jakob, Bettina Kraenzlin, Sigrid Hoffmann, Norbert Gretz. Faster rates of post-puberty kidney deterioration in males is correlated with elevated oxidative stress in males vs females at early puberty. BMC genomics. 2007 Jul; 8(?):221. doi: 10.1186/1471-2164-8-221. [PMID: 17620128]
  • 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]
  • Neil J Anderson, Isabelle Seif, David J Nutt, Alan L Hudson, Emma S J Robinson. Autoradiographical distribution of imidazoline binding sites in monoamine oxidase A deficient mice. Journal of neurochemistry. 2006 Mar; 96(6):1551-9. doi: 10.1111/j.1471-4159.2006.03662.x. [PMID: 16476082]
  • Robert Barouki. [Ageing free radicals and cellular stress]. Medecine sciences : M/S. 2006 Mar; 22(3):266-72. doi: 10.1051/medsci/2006223266. [PMID: 16527207]
  • Yuko Fukuyama, Adriana A Kolender, Masae Nishioka, Hiroshi Nonami, María C Matulewicz, Rosa Erra-Balsells, Alberto S Cerezo. Matrix-assisted ultraviolet laser desorption/ionization time-of-flight mass spectrometry of beta-(1 --> 3), beta-(1 --> 4)-xylans from Nothogenia fastigiata using nor-harmane as matrix. Rapid communications in mass spectrometry : RCM. 2005; 19(3):349-58. doi: 10.1002/rcm.1783. [PMID: 15645484]
  • W Pfau, K Skog. Exposure to beta-carbolines norharman and harman. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Mar; 802(1):115-26. doi: 10.1016/j.jchromb.2003.10.044. [PMID: 15036003]
  • Y Totsuka, T Takamura-Enya, R Nishigaki, T Sugimura, K Wakabayashi. Mutagens formed from beta-carbolines with aromatic amines. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Mar; 802(1):135-41. doi: 10.1016/j.jchromb.2003.10.041. [PMID: 15036005]
  • E Persson, G Graziani, R Ferracane, V Fogliano, K Skog. Influence of antioxidants in virgin olive oil on the formation of heterocyclic amines in fried beefburgers. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2003 Nov; 41(11):1587-97. doi: 10.1016/s0278-6915(03)00190-x. [PMID: 12963012]
  • Wulf Dröge. Oxidative stress and aging. Advances in experimental medicine and biology. 2003; 543(?):191-200. doi: 10.1007/978-1-4419-8997-0_14. [PMID: 14713123]
  • C Ancolio, N Azas, V Mahiou, E Ollivier, C Di Giorgio, A Keita, P Timon-David, G Balansard. Antimalarial activity of extracts and alkaloids isolated from six plants used in traditional medicine in Mali and Sao Tome. Phytotherapy research : PTR. 2002 Nov; 16(7):646-9. doi: 10.1002/ptr.1025. [PMID: 12410545]
  • Lucia Pötsch, Gisela Skopp. [Serum norharman and harman analysis using high pressure liquid chromatography/mass spectrometry and value of beta-carbolines as blood alcohol markers]. Archiv fur Kriminologie. 2002 Nov; 210(5-6):146-57. doi: NULL. [PMID: 12532677]
  • Jianchun Xie, Lili Zhu, Xiaojie Xu. Affinitive separation and on-line identification of antitumor components from Peganum nigellastrum by coupling a chromatographic column of target analogue imprinted polymer with mass spectrometry. Analytical chemistry. 2002 May; 74(10):2352-60. doi: 10.1021/ac015755i. [PMID: 12038761]
  • Hans Rommelspacher, Mignon Meier-Henco, Michael Smolka, Charlotte Kloft. The levels of norharman are high enough after smoking to affect monoamineoxidase B in platelets. European journal of pharmacology. 2002 Apr; 441(1-2):115-25. doi: 10.1016/s0014-2999(02)01452-8. [PMID: 12007928]
  • Homer S Black. Pro-oxidant and anti-oxidant mechanism(s) of BHT and beta-carotene in photocarcinogenesis. Frontiers in bioscience : a journal and virtual library. 2002 Apr; 7(?):d1044-55. doi: 10.2741/a830. [PMID: 11897548]
  • N Azas, N Laurencin, F Delmas, Giorgio C Di, M Gasquet, M Laget, P Timon-David. Synergistic in vitro antimalarial activity of plant extracts used as traditional herbal remedies in Mali. Parasitology research. 2002 Feb; 88(2):165-71. doi: 10.1007/s004360100454. [PMID: 11936507]
  • Armin Madadkar Sobhani, Sultan-Ahmad Ebrahimi, Massoud Mahmoudian. An in vitro evaluation of human DNA topoisomerase I inhibition by Peganum harmala L. seeds extract and its beta-carboline alkaloids. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2002 Jan; 5(1):19-23. doi: . [PMID: 12042115]
  • H Fukazawa, H Matsushita, Y Terao. Identification of co-mutagenic chlorinated harmans in final effluent from a sewage treatment plant. Mutation research. 2001 Apr; 491(1-2):65-70. doi: 10.1016/s1383-5718(01)00132-2. [PMID: 11287299]
  • K Kitani, C Minami, T Yamamoto, W Maruyama, S Kanai, G O Ivy, M C Carrillo. Do antioxidant strategies work against aging and age-associated disorders? Propargylamines: a possible antioxidant strategy. Annals of the New York Academy of Sciences. 2001 Apr; 928(?):248-60. doi: 10.1111/j.1749-6632.2001.tb05654.x. [PMID: 11795516]
  • H Nonami, F Wu, R P Thummel, Y Fukuyama, H Yamaoka, R Erra-Balsells. Evaluation of pyridoindoles, pyridylindoles and pyridylpyridoindoles as matrices for ultraviolet matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Rapid communications in mass spectrometry : RCM. 2001; 15(23):2354-73. doi: 10.1002/rcm.514. [PMID: 11746903]
  • K Nakano, K Suyama, H Fukazawa, M Uchida, K Wakabayashi, T Shiozawa, Y Terao. Chlorination of harman and norharman with sodium hypochlorite and co-mutagenicity of the chlorinated products. Mutation research. 2000 Oct; 470(2):141-6. doi: 10.1016/s1383-5718(00)00095-4. [PMID: 11027968]
  • W Zheng, S Wang, L F Barnes, Y Guan, E D Louis. Determination of harmane and harmine in human blood using reversed-phased high-performance liquid chromatography and fluorescence detection. Analytical biochemistry. 2000 Mar; 279(2):125-9. doi: 10.1006/abio.1999.4456. [PMID: 10706780]
  • H Tsuchiya, M Sato, I Watanabe. Antiplatelet activity of soy sauce as functional seasoning. Journal of agricultural and food chemistry. 1999 Oct; 47(10):4167-74. doi: 10.1021/jf990147d. [PMID: 10552785]
  • H Rommelspacher, M Wiest, R Neuhaus, W Platzgummer, L G Schmidt, P Neuhaus. Long-term changes of markers of alcoholism after orthotopic liver transplantation (OLT). Transplantation. 1996 Nov; 62(10):1451-5. doi: 10.1097/00007890-199611270-00012. [PMID: 8958271]
  • N Wodarz, G A Wiesbeck, H Rommelspacher, P Riederer, J Böning. Excretion of beta-carbolines harman and norharman in 24-hour urine of chronic alcoholics during withdrawal and controlled abstinence. Alcoholism, clinical and experimental research. 1996 Jun; 20(4):706-10. doi: 10.1111/j.1530-0277.1996.tb01675.x. [PMID: 8800388]
  • C D Spies, H Rommelspacher, C Schnapper, C Müller, C Marks, G Berger, C Conrad, S Blum, M Specht, L Hannemann. Beta-carbolines in chronic alcoholics undergoing elective tumor resection. Alcoholism, clinical and experimental research. 1995 Aug; 19(4):969-76. doi: 10.1111/j.1530-0277.1995.tb00976.x. [PMID: 7485848]