Benzo[c]phenanthridine (BioDeep_00000174670)
human metabolite blood metabolite
代谢物信息卡片
9-azatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-1(10),2,4,6,8,11,13,15,17-nonaene
化学式: C17H11N (229.0891)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 59.3%
分子结构信息
SMILES: C1=CC=C2C(=C1)C=CC3=C2N=CC4=CC=CC=C34
InChI: InChI=1S/C17H11N/c1-4-8-15-12(5-1)9-10-16-14-7-3-2-6-13(14)11-18-17(15)16/h1-11H
数据库引用编号
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)
1 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 |
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文献列表
- Jana Urbanová, Kristýna Pěnčíková, Jana Gregorová, Barbora Hohnová, Lenka Sťavíková, Pavel Karásek, Michal Roth, Eva Táborská. Isolation of quaternary benzo[c]phenanthridine alkaloids from Macleaya microcarpa (MAXIM.) FEDDE: comparison of maceration, Soxhlet extraction and pressurised liquid extraction.
Phytochemical analysis : PCA.
2012 Sep; 23(5):477-82. doi:
10.1002/pca.2344. [PMID: 22371200] - K Pěnčíková, P Kollár, V Müller Závalová, E Táborská, J Urbanová, J Hošek. Investigation of sanguinarine and chelerythrine effects on LPS-induced inflammatory gene expression in THP-1 cell line.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2012 Jul; 19(10):890-5. doi:
10.1016/j.phymed.2012.04.001. [PMID: 22592163] - Jindřiška Hammerová, Stjepan Uldrijan, Eva Táborská, Alena Hyršlová Vaculová, Iva Slaninová. Necroptosis modulated by autophagy is a predominant form of melanoma cell death induced by sanguilutine.
Biological chemistry.
2012 Jul; 393(7):647-58. doi:
10.1515/hsz-2011-0279. [PMID: 22944669] - Jia-Yun Yao, Zhi-Ming Zhou, Xiao-yi Pan, Gui-jie Hao, Xi-Lian Li, Yang Xu, Jin-Yu Shen, Hong-shun Ru, Wen-lin Yin. In vivo anthelmintic activity of chelidonine from Chelidonium majus L. against Dactylogyrus intermedius in Carassius auratus.
Parasitology research.
2011 Nov; 109(5):1465-9. doi:
10.1007/s00436-011-2416-2. [PMID: 21537985] - Xi-Lian Li, Jia-Yun Yao, Zhi-Ming Zhou, Jin-Yu Shen, Hong-Shun Ru, Xiao-Lin Liu. Activity of the chelerythrine, a quaternary benzo[c]phenanthridine alkaloid from Chelidonium majus L. on Dactylogyrus intermedius.
Parasitology research.
2011 Jul; 109(1):247-52. doi:
10.1007/s00436-011-2320-9. [PMID: 21400114] - Xiao-Feng Niu, Ping Zhou, Wei-Feng Li, Hong-Bo Xu. Effects of chelerythrine, a specific inhibitor of cyclooxygenase-2, on acute inflammation in mice.
Fitoterapia.
2011 Jun; 82(4):620-5. doi:
10.1016/j.fitote.2011.01.020. [PMID: 21291962] - Kristýna Pěnčíková, Jana Urbanová, Pavel Musil, Eva Táborská, Jana Gregorová. Seasonal variation of bioactive alkaloid contents in Macleaya microcarpa (Maxim.) Fedde.
Molecules (Basel, Switzerland).
2011 Apr; 16(4):3391-401. doi:
10.3390/molecules16043391. [PMID: 21512447] - J Juskiewicz, R Gruzauskas, Z Zdunczyk, A Semaskaite, J Jankowski, Z Totilas, V Jarule, V Sasyte, P Zdunczyk, A Raceviciute-Stupeliene, G Svirmickas. Effects of dietary addition of Macleaya cordata alkaloid extract on growth performance, caecal indices and breast meat fatty acids profile in male broilers.
Journal of animal physiology and animal nutrition.
2011 Apr; 95(2):171-8. doi:
10.1111/j.1439-0396.2010.01037.x. [PMID: 20666860] - Isabel Desgagné-Penix, Morgan F Khan, David C Schriemer, Dustin Cram, Jacek Nowak, Peter J Facchini. Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures.
BMC plant biology.
2010 Nov; 10(?):252. doi:
10.1186/1471-2229-10-252. [PMID: 21083930] - Alain Deroussent, Micheline Ré, Henri Hoellinger, Thierry Cresteil. Metabolism of sanguinarine in human and in rat: characterization of oxidative metabolites produced by human CYP1A1 and CYP1A2 and rat liver microsomes using liquid chromatography-tandem mass spectrometry.
Journal of pharmaceutical and biomedical analysis.
2010 Jul; 52(3):391-7. doi:
10.1016/j.jpba.2009.09.014. [PMID: 19804952] - Hironori Iwasaki, Takafumi Okabe, Kensaku Takara, Takayoshi Toda, Masayuki Shimatani, Hirosuke Oku. Tumor-selective cytotoxicity of benzo[c]phenanthridine derivatives from Toddalia asiatica Lam.
Cancer chemotherapy and pharmacology.
2010 Mar; 65(4):719-26. doi:
10.1007/s00280-009-1077-7. [PMID: 19629483] - Fanyan Meng, Guoying Zuo, Xiaoyan Hao, Genchun Wang, Haitao Xiao, Jiquan Zhang, Guili Xu. Antifungal activity of the benzo[c]phenanthridine alkaloids from Chelidonium majus Linn against resistant clinical yeast isolates.
Journal of ethnopharmacology.
2009 Sep; 125(3):494-6. doi:
10.1016/j.jep.2009.07.029. [PMID: 19647059] - Andreas Gesell, Megan Rolf, Jörg Ziegler, María Luisa Díaz Chávez, Fong-Chin Huang, Toni M Kutchan. CYP719B1 is salutaridine synthase, the C-C phenol-coupling enzyme of morphine biosynthesis in opium poppy.
The Journal of biological chemistry.
2009 Sep; 284(36):24432-42. doi:
10.1074/jbc.m109.033373. [PMID: 19567876] - Jirí Vrba, Petr Dolezel, Jaroslav Vicar, Jitka Ulrichová. Cytotoxic activity of sanguinarine and dihydrosanguinarine in human promyelocytic leukemia HL-60 cells.
Toxicology in vitro : an international journal published in association with BIBRA.
2009 Jun; 23(4):580-8. doi:
10.1016/j.tiv.2009.01.016. [PMID: 19346183] - Adela Zdarilova, Eva Vrublova, Jitka Vostalova, Borivoj Klejdus, David Stejskal, Jitka Proskova, Pavel Kosina, Alena Svobodova, Rostislav Vecera, Jan Hrbac, Drahomira Cernochova, Jaroslav Vicar, Jitka Ulrichova, Vilim Simanek. Natural feed additive of Macleaya cordata: safety assessment in rats a 90-day feeding experiment.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2008 Dec; 46(12):3721-6. doi:
10.1016/j.fct.2008.09.054. [PMID: 18930108] - Eva Vrublova, Jitka Vostalova, Rostislav Vecera, Borivoj Klejdus, David Stejskal, Pavel Kosina, Adela Zdarilova, Alena Svobodova, Vaclav Lichnovsky, Pavel Anzenbacher, Zdenek Dvorak, Jaroslav Vicar, Vilim Simanek, Jitka Ulrichova. The toxicity and pharmacokinetics of dihydrosanguinarine in rat: a pilot study.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2008 Jul; 46(7):2546-53. doi:
10.1016/j.fct.2008.04.013. [PMID: 18495316] - Borivoj Klejdus, Lea Lojková, Pavel Kosina, Jitka Ulrichová, Vilím Simánek, Vlastimil Kubán. Liquid chromatographic/electrospray mass spectrometric determination (LC/ESI-MS) of chelerythrine and dihydrochelerythrine in near-critical CO(2) extracts from real and spiked plasma samples.
Talanta.
2007 Jun; 72(4):1348-56. doi:
10.1016/j.talanta.2007.01.055. [PMID: 19071768] - Jana Suchomelová, Hana Bochoráková, Hana Paulová, Pavel Musil, Eva Táborská. HPLC quantification of seven quaternary benzo[c]phenanthridine alkaloids in six species of the family Papaveraceae.
Journal of pharmaceutical and biomedical analysis.
2007 May; 44(1):283-7. doi:
10.1016/j.jpba.2007.02.005. [PMID: 17367981] - Min Cai, Yan Zhou, Xiaoling Wang, Rui Li, Xun Liao, Lisheng Ding. Rapid structural characterization of isomeric benzo[c]phenanthridine alkaloids from the roots of Zanthoxylum nitidium by liquid chromatography combined with electrospray ionization tandem mass spectrometry.
Rapid communications in mass spectrometry : RCM.
2007; 21(12):1931-6. doi:
10.1002/rcm.3045. [PMID: 17510939] - Jürgen Schmidt, Chotima Boettcher, Christine Kuhnt, Toni M Kutchan, Meinhart H Zenk. Poppy alkaloid profiling by electrospray tandem mass spectrometry and electrospray FT-ICR mass spectrometry after [ring-13C6]-tyramine feeding.
Phytochemistry.
2007 Jan; 68(2):189-202. doi:
10.1016/j.phytochem.2006.10.003. [PMID: 17113612] - Clynton W Halstead, Paul I Forster, Peter G Waterman. Alkaloids from the stem bark of an Australian population of Zanthoxylum ovalifolium.
Natural product research.
2006 Aug; 20(10):940-5. doi:
10.1080/14786410500462710. [PMID: 16854723] - M T Martin, L H Rasoanaivo, A Raharisololalao. Phenanthridine alkaloids from Zanthoxylum madagascariense.
Fitoterapia.
2005 Sep; 76(6):590-3. doi:
10.1016/j.fitote.2005.04.003. [PMID: 16000237] - Andreas Vogt, Aletheia Tamewitz, John Skoko, Rachel P Sikorski, Kenneth A Giuliano, John S Lazo. The benzo[c]phenanthridine alkaloid, sanguinarine, is a selective, cell-active inhibitor of mitogen-activated protein kinase phosphatase-1.
The Journal of biological chemistry.
2005 May; 280(19):19078-86. doi:
10.1074/jbc.m501467200. [PMID: 15753082] - Susanne Frick, Robert Kramell, Jürgen Schmidt, Anthony J Fist, Toni M Kutchan. Comparative qualitative and quantitative determination of alkaloids in narcotic and condiment Papaver somniferum cultivars.
Journal of natural products.
2005 May; 68(5):666-73. doi:
10.1021/np0496643. [PMID: 15921406] - Maria Minunni, Sara Tombelli, Marco Mascini, Annarita Bilia, M Camilla Bergonzi, F F Vincieri. An optical DNA-based biosensor for the analysis of bioactive constituents with application in drug and herbal drug screening.
Talanta.
2005 Jan; 65(2):578-85. doi:
10.1016/j.talanta.2004.07.020. [PMID: 18969838] - Henri Hoellinger, Micheline Re, Alain Deroussent, Ravindra Pratap Singh, Thierry Cresteil. Quantitative liquid chromatographic determination of sanguinarine in cell culture medium and in rat urine and plasma.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2004 Jan; 799(2):195-200. doi:
10.1016/j.jchromb.2003.10.023. [PMID: 14670737] - Simon Gibbons, Julia Leimkugel, Moyo Oluwatuyi, Michael Heinrich. Activity of Zanthoxylum clava-herculis extracts against multi-drug resistant methicillin-resistant Staphylococcus aureus (mdr-MRSA).
Phytotherapy research : PTR.
2003 Mar; 17(3):274-5. doi:
10.1002/ptr.1112. [PMID: 12672160] - A Sedo, R Malík, J Vicar, V Simánek, J Ulrichová. Quaternary benzo[c]phenanthridine alkaloids as inhibitors of dipeptidyl peptidase IV-like activity baring enzymes in human blood plasma and glioma cell lines.
Physiological research.
2003; 52(3):367-72. doi:
. [PMID: 12790770] - T Belyaeva, E Leontieva, A Shpakov, T Mozhenok, M Faddejeva. Sensitivity of lysosomal enzymes to the plant alkaloid sanguinarine: comparison with other SH-specific agents.
Cell biology international.
2003; 27(11):887-95. doi:
10.1016/s1065-6995(03)00161-6. [PMID: 14585282] - Catherina Caballero-George, Patrick M L Vanderheyden, Sandra Apers, Hilde Van den Heuvel, Pablo N Solis, Mahabir P Gupta, Magda Claeys, Luc Pieters, Georges Vauquelin, Arnold J Vlietinck. Inhibitory activity on binding of specific ligands to the human angiotensin II AT(1) and endothelin 1 ET(A) receptors: bioactive benzo[c]phenanthridine alkaloids from the root of Bocconia frutescens.
Planta medica.
2002 Sep; 68(9):770-5. doi:
10.1055/s-2002-34406. [PMID: 12357384] - Aleksi Sedo, Kvetoslava Vlasicová, Petr Barták, Radim Vespalec, Jaroslav Vicar, Vilim Simánek, Jitka Ulrichová. Quaternary benzo[c]phenanthridine alkaloids as inhibitors of aminopeptidase N and dipeptidyl peptidase IV.
Phytotherapy research : PTR.
2002 Feb; 16(1):84-7. doi:
10.1002/ptr.969. [PMID: 11807974] - J Ulrichová, Z Dvorák, J Vicar, J Lata, J Smrzová, A Sedo, V Simánek. Cytotoxicity of natural compounds in hepatocyte cell culture models. The case of quaternary benzo[c]phenanthridine alkaloids.
Toxicology letters.
2001 Dec; 125(1-3):125-32. doi:
10.1016/s0378-4274(01)00430-1. [PMID: 11701231] - K E Kim, W J Cho, S J Chang, C S Yong, C H Lee, D D Kim. Pharmacokinetics of a new antitumor 3-arylisoquinoline derivative, CWJ-a-5.
International journal of pharmaceutics.
2001 Apr; 217(1-2):101-10. doi:
10.1016/s0378-5173(01)00593-2. [PMID: 11292546] - . .
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