Ajmaline (BioDeep_00000001881)

Main id: BioDeep_00000395750

 

human metabolite PANOMIX_OTCML-2023 blood metabolite Chemicals and Drugs natural product


代谢物信息卡片


(1R,9R,10S,12R,13S,14R,16S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-14,18-diol

化学式: C20H26N2O2 (326.1994)
中文名称: 阿吗灵
谱图信息: 最多检出来源 Viridiplantae(plant) 100%

分子结构信息

SMILES: CCC1C2CC3C4C5(CC(C2C5O)N3C1O)C6=CC=CC=C6N4C
InChI: InChI=1S/C20H26N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-19,23-24H,3,8-9H2,1-2H3

描述信息

Ajmaline, also known as (+)-ajmaline, is a member of the class of compounds known as ajmaline-sarpagine alkaloids. Ajmaline-sarpagine alkaloids are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether. Ajmaline is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Ajmaline can be synthesized from ajmalan. Ajmaline is also a parent compound for other transformation products, including but not limited to, vinorine, norajmaline, and 17-O-acetylajmaline. Ajmaline can be found in a number of food items such as soursop, jews ear, small-leaf linden, and soft-necked garlic, which makes ajmaline a potential biomarker for the consumption of these food products. Ajmaline can be found primarily in blood and urine. Ajmaline is a drug which is used for use as an antiarrhythmic agent. The compound was first isolated by Salimuzzaman Siddiqui in 1931 from the roots of Rauvolfia serpentina. He named it ajmaline, after Hakim Ajmal Khan, one of the most illustrious practitioners of Unani medicine in South Asia. Ajmaline can be found in most species of the Rauvolfia genus as well as Catharanthus roseus. In addition to Southeast Asia, Rauvolfia species have also been found in tropical regions of India, Africa, South America, and some oceanic islands. Other indole alkaloids found in Rauvolfia include reserpine, ajmalicine, serpentine, corynanthine, and yohimbine. While 86 alkaloids have been discovered throughout Rauvolfia vomitoria, ajmaline is mainly isolated from the stem bark and roots of the plant . The class I antiarrhythmic agents interfere with the sodium channel. A class IA agent lengthens the action potential (right shift) which brings about improvement in abnormal heart rhythms. This drug in particular has a high affinity for the Nav 1.5 sodium channel (DrugBank).
An alkaloid found in the root of Rauwolfia serpentina, among other plant sources. It is a class Ia antiarrhythmic agent that apparently acts by changing the shape and threshold of cardiac action potentials. Ajmaline produces potent sodium channel blocking effects and a very short half-life which makes it a very useful drug for acute intravenous treatments. The drug has been very popular in some countries for the treatment of atrial fibrillation in patients with the Wolff Parkinson White syndrome and in well tolerated monomorphic ventricular tachycardias. It has also been used for many years as a drug to challenge the conduction system of the heart in cases of bundle branch block and syncope. In these cases, abnormal prolongation of the HV interval has been taken as a proof for infrahisian conduction defects tributary for permanent pacemaker implantation.
D002317 - Cardiovascular Agents > D026941 - Sodium Channel Blockers > D061567 - Voltage-Gated Sodium Channel Blockers
D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents
D049990 - Membrane Transport Modulators
Ajmaline (Cardiorythmine) is a sodium channel blocking, class 1A anti-arrhythmic agent. Ajmaline blocks HERG currents with an IC50 of 1 μM in HEK cells and 42.3 μM in Xenopus oocytes. Ajmaline can be used for the research of the ventricular tachyarrhythmia[1][2].
Ajmaline (Cardiorythmine) is a sodium channel blocking, class 1A anti-arrhythmic agent. Ajmaline blocks HERG currents with an IC50 of 1 μM in HEK cells and 42.3 μM in Xenopus oocytes. Ajmaline can be used for the research of the ventricular tachyarrhythmia[1][2].

同义名列表

11 个代谢物同义名

(1R,9R,10S,12R,13S,14R,16S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-14,18-diol; (5AR,6S,8S,10S,11S,11as,12ar,13R)-5-methyl-5a,6,8,9,10,11,11a,12-octahydro-5H-6,10:11,12a-dimethanoindolo[3,2-b]quinolizine-8,13-diol; CID 44891335; (+)-Ajmaline; Ajmaline; Aritmina; Ajimalin; Ajmalin; Cardiorythmine; Isoajmaline; Ajmaline



数据库引用编号

31 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(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(3)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

35 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


文献列表

  • Enzo Lezin, Inês Carqueijeiro, Clément Cuello, Mickael Durand, Hans J Jansen, Valentin Vergès, Caroline Birer Williams, Audrey Oudin, Thomas Dugé de Bernonville, Julien Petrignet, Noémie Celton, Benoit St-Pierre, Nicolas Papon, Chao Sun, Ron P Dirks, Sarah Ellen O'Connor, Michael Krogh Jensen, Sébastien Besseau, Vincent Courdavault. A chromosome-scale genome assembly of Rauvolfia tetraphylla facilitates identification of the complete ajmaline biosynthetic pathway. Plant communications. 2024 Apr; 5(4):100784. doi: 10.1016/j.xplc.2023.100784. [PMID: 38155576]
  • Jun Guo, Di Gao, Jiazhang Lian, Yang Qu. De novo biosynthesis of antiarrhythmic alkaloid ajmaline. Nature communications. 2024 Jan; 15(1):457. doi: 10.1038/s41467-024-44797-z. [PMID: 38212296]
  • Michelle M Monasky, Emanuele Micaglio, Giuseppe Ciconte, Ilaria Rivolta, Valeria Borrelli, Andrea Ghiroldi, Sara D'Imperio, Anna Binda, Dario Melgari, Sara Benedetti, Predrag Mitrovic, Luigi Anastasia, Valerio Mecarocci, Žarko Ćalović, Giorgio Casari, Carlo Pappone. Novel SCN5A p.Val1667Asp Missense Variant Segregation and Characterization in a Family with Severe Brugada Syndrome and Multiple Sudden Deaths. International journal of molecular sciences. 2021 Apr; 22(9):. doi: 10.3390/ijms22094700. [PMID: 33946750]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Xinye Li, Hongcai Shang, Yanwei Xing. New risk stratification on SCN5A mutation in Brugada syndrome. International journal of cardiology. 2018 11; 271(?):123. doi: 10.1016/j.ijcard.2018.05.122. [PMID: 30223345]
  • Thitima Rukachaisirikul, Suwadee Chokchaisiri, Parichat Suebsakwong, Apichart Suksamrarn, Chainarong Tocharus. A New Ajmaline-type Alkaloid from the Roots of Rauvolfia serpentina. Natural product communications. 2017 Apr; 12(4):495-498. doi: . [PMID: 30520580]
  • Paulo Cázares-Flores, Dylan Levac, Vincenzo De Luca. Rauvolfia serpentina N-methyltransferases involved in ajmaline and Nβ -methylajmaline biosynthesis belong to a gene family derived from γ-tocopherol C-methyltransferase. The Plant journal : for cell and molecular biology. 2016 08; 87(4):335-42. doi: 10.1111/tpj.13186. [PMID: 27122470]
  • Fangrui Wu, Petra Kerčmar, Chenggui Zhang, Joachim Stöckigt. Sarpagan-Ajmalan-Type Indoles: Biosynthesis, Structural Biology, and Chemo-Enzymatic Significance. The Alkaloids. Chemistry and biology. 2016; 76(?):1-61. doi: 10.1016/bs.alkal.2015.10.001. [PMID: 26827882]
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  • Siew-Huah Lim, Yun-Yee Low, Saravana Kumar Sinniah, Kien-Thai Yong, Kae-Shin Sim, Toh-Seok Kam. Macroline, akuammiline, sarpagine, and ajmaline alkaloids from Alstonia macrophylla. Phytochemistry. 2014 Feb; 98(?):204-15. doi: 10.1016/j.phytochem.2013.11.014. [PMID: 24342109]
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  • Eugenia Gallo, Elisa Giocaliere, Silvia Benemei, Anna Rita Bilia, Anastasia Karioti, Alessandra Pugi, Marina di Pirro, Francesca Menniti-Ippolito, Giuseppe Pieraccini, Luigi Gori, Alessandro Mugelli, Fabio Firenzuoli, Alfredo Vannacci. Anything to declare? Possible risks for patients' health resulting from undeclared plants in herbal supplements. British journal of clinical pharmacology. 2012 Mar; 73(3):482-3. doi: 10.1111/j.1365-2125.2011.04115.x. [PMID: 21988365]
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  • Grégory Guirimand, Vincent Courdavault, Arnaud Lanoue, Samira Mahroug, Anthony Guihur, Nathalie Blanc, Nathalie Giglioli-Guivarc'h, Benoit St-Pierre, Vincent Burlat. Strictosidine activation in Apocynaceae: towards a "nuclear time bomb"?. BMC plant biology. 2010 Aug; 10(?):182. doi: 10.1186/1471-2229-10-182. [PMID: 20723215]
  • Rolf W Sparidans, Pim Langendijk, Eric Boers, Erik van Kan, Hanno L Tan, Jos H Beijnen. Liquid chromatographic assay with fluorescence detection to determine ajmaline in serum from patients with suspected Brugada syndrome. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Aug; 878(23):2168-72. doi: 10.1016/j.jchromb.2010.06.017. [PMID: 20620121]
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  • Lianli Sun, Martin Ruppert, Yuri Sheludko, Heribert Warzecha, Yu Zhao, Joachim Stöckigt. Purification, cloning, functional expression and characterization of perakine reductase: the first example from the AKR enzyme family, extending the alkaloidal network of the plant Rauvolfia. Plant molecular biology. 2008 Jul; 67(5):455-67. doi: 10.1007/s11103-008-9331-7. [PMID: 18409028]
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  • Joachim Stöckigt, Santosh Panjikar. Structural biology in plant natural product biosynthesis--architecture of enzymes from monoterpenoid indole and tropane alkaloid biosynthesis. Natural product reports. 2007 Dec; 24(6):1382-400. doi: 10.1039/b711935f. [PMID: 18033585]
  • Leif Barleben, Santosh Panjikar, Martin Ruppert, Juergen Koepke, Joachim Stöckigt. Molecular architecture of strictosidine glucosidase: the gateway to the biosynthesis of the monoterpenoid indole alkaloid family. The Plant cell. 2007 Sep; 19(9):2886-97. doi: 10.1105/tpc.106.045682. [PMID: 17890378]
  • Mikhail V Sogonov, Lisa A Castlebury, Amy Y Rossman, James F White. The type species of Apiognomonia, A. veneta, with its Discula anamorph is distinct from A. errabunda. Mycological research. 2007 Jun; 111(Pt 6):693-709. doi: 10.1016/j.mycres.2007.03.013. [PMID: 17604146]
  • Xueyan Ma, Santosh Panjikar, Juergen Koepke, Elke Loris, Joachim Stöckigt. The structure of Rauvolfia serpentina strictosidine synthase is a novel six-bladed beta-propeller fold in plant proteins. The Plant cell. 2006 Apr; 18(4):907-20. doi: 10.1105/tpc.105.038018. [PMID: 16531499]
  • Xueyan Ma, Juergen Koepke, Anja Bayer, Günter Fritzsch, Hartmut Michel, Joachim Stöckigt. Crystallization and preliminary X-ray analysis of native and selenomethionyl vinorine synthase from Rauvolfia serpentina. Acta crystallographica. Section D, Biological crystallography. 2005 Jun; 61(Pt 6):694-6. doi: 10.1107/s0907444904028756. [PMID: 15930622]
  • Xueyan Ma, Juergen Koepke, Santosh Panjikar, Günter Fritzsch, Joachim Stöckigt. Crystal structure of vinorine synthase, the first representative of the BAHD superfamily. The Journal of biological chemistry. 2005 Apr; 280(14):13576-83. doi: 10.1074/jbc.m414508200. [PMID: 15665331]
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