Lobeline (BioDeep_00000000751)

 

Secondary id: BioDeep_00000180514, BioDeep_00000410437

natural product PANOMIX_OTCML-2023


代谢物信息卡片


Ethanone, 2-(6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenyl-, (2R-(2alpha,6alpha(S*)))-

化学式: C22H27NO2 (337.2041682)
中文名称: 洛贝林, 洛贝林
谱图信息: 最多检出来源 Viridiplantae(plant) 6.98%

分子结构信息

SMILES: CN1C(CC(=O)c2ccccc2)CCCC1CC(O)c1ccccc1
InChI: InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3

描述信息

(-)-lobeline is an optically active piperidine alkaloid having a 2-oxo-2-phenylethyl substituent at the 2-position and a 2-hydroxy-2-phenylethyl group at the 6-position. It has a role as a nicotinic acetylcholine receptor agonist. It is a piperidine alkaloid, a tertiary amine and an aromatic ketone.
Lobeline is a natural product found in Lobelia sessilifolia, Lobelia inflata, and other organisms with data available.
An alkaloid that has actions similar to NICOTINE on nicotinic cholinergic receptors but is less potent. It has been proposed for a variety of therapeutic uses including in respiratory disorders, peripheral vascular disorders, insomnia, and smoking cessation.
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D005731 - Ganglionic Stimulants
C78272 - Agent Affecting Nervous System > C47796 - Cholinergic Agonist > C73579 - Nicotinic Agonist
D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018679 - Cholinergic Agonists
D019141 - Respiratory System Agents
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.733
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.728

同义名列表

43 个代谢物同义名

Ethanone, 2-(6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenyl-, (2R-(2alpha,6alpha(S*)))-; 2-((2R,6S)-6-((S)-2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethan-1-one; 2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone; 2-{(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl}-1-phenylethanone; 2-((2R,6S)-6-((2S)-2-HYDROXY-2-PHENYLETHYL)-1-METHYL-2-PIPERIDINYL)-1-PHENYLETHANONE; 2-(6-(2-Hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenylethanone; 2-(6-(.BETA.-HYDROXYPHENETHYL)-1-METHYL-2-PIPERIDYL)ACETOPHENONE; 2-(6-(beta-Hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone; 5-21-12-00627 (Beilstein Handbook Reference); 8,10-Diphenyllobelionol; Lobelina [INN-Spanish]; Lobelinum [INN-Latin]; Alpha-Lobeline HCl; Lobeline [INN:BAN]; LOBELINE [WHO-DD]; Prestwick3_000585; Prestwick2_000585; Prestwick0_000585; Sulfate, Lobeline; Prestwick1_000585; Lobeline sulfate; LOBELINUM [HPUS]; .alpha.-Lobeline; UNII-D0P25S3P81; Lobeline (INN); alpha-Lobeline; Lobeline [INN]; Lopac0_000698; BPBio1_000474; LOBELINE [MI]; Tox21_110900; (-)-Lobeline; CAS-90-69-7; D0P25S3P81; Smokeless; Lobelinum; Inflatine; Lobeline; Lobelina; Lobnico; Lobelin; L0B; Lobron



数据库引用编号

30 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)

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

  • Shu-Rong Chen, Yih-Fung Chen, Jue-Jun Lin, Tzu-Yi Ke, Yun-Sheng Lin, Yuan-Bin Cheng. 2,6-Disubstituted Piperidine Alkaloids with Neuroprotective Activity from Hippobroma longiflora. Planta medica. 2023 Mar; 89(3):308-315. doi: 10.1055/a-1903-2663. [PMID: 36482147]
  • Lusheng Chen, Xiumei Ren, Fengxing Li, Haiping Deng, Guanghong Ding, Wei Yao, Ling Zhao, Xueyong Shen. New smokeless moxibustion for knee osteoarthritis: A study protocol for a multicenter, single-blind, randomized controlled trial. Medicine. 2022 Oct; 101(40):e30700. doi: 10.1097/md.0000000000030700. [PMID: 36221329]
  • Huan-Hua Xu, Liang Yang, Ming-Xia Tang, An-Ping Ye, Bo-Dan Tu, Zhen-Hong Jiang, Jian-Feng Yi. From cis-Lobeline to trans-Lobeline: Study on the Pharmacodynamics and Isomerization Factors. Molecules (Basel, Switzerland). 2022 Sep; 27(19):. doi: 10.3390/molecules27196253. [PMID: 36234790]
  • Xin Zhu, Hui Li, Tian-Min Zhu, Lu Li, Shou-Liang Hu. [Acupuncture combined with smokeless or smoky moxibustion for regulating immune function of experimental chronic rhinosinusitis mice]. Zhen ci yan jiu = Acupuncture research. 2021 Sep; 46(9):757-62. doi: 10.13702/j.1000-0607.201021. [PMID: 34558241]
  • Haixing Wang, Yuanyuan Li, Yeqing Huang, Chunyan Zhao, Hon-Yeung Cheung. Chemical Profiling of Lobelia chinensis with High-Performance Liquid Chromatography/Quadrupole Time-of-Flight Mass Spectrometry (HPLC/Q-TOF MS) Reveals Absence of Lobeline in the Herb. Molecules (Basel, Switzerland). 2018 Dec; 23(12):. doi: 10.3390/molecules23123258. [PMID: 30544710]
  • Emily R Hankosky, Shyam R Joolakanti, Justin R Nickell, Venumadhav Janganati, Linda P Dwoskin, Peter A Crooks. Fluoroethoxy-1,4-diphenethylpiperidine and piperazine derivatives: Potent and selective inhibitors of [3H]dopamine uptake at the vesicular monoamine transporter-2. Bioorganic & medicinal chemistry letters. 2017 12; 27(24):5467-5472. doi: 10.1016/j.bmcl.2017.10.039. [PMID: 29153425]
  • Justin R Nickell, Kiran B Siripurapu, David B Horton, Guangrong Zheng, Peter A Crooks, Linda P Dwoskin. GZ-793A inhibits the neurochemical effects of methamphetamine via a selective interaction with the vesicular monoamine transporter-2. European journal of pharmacology. 2017 Jan; 795(?):143-149. doi: 10.1016/j.ejphar.2016.12.016. [PMID: 27986625]
  • Shyamsunder R Joolakanti, Justin R Nickell, Venumadhav Janganati, Guangrong Zheng, Linda P Dwoskin, Peter A Crooks. Lobelane analogues containing 4-hydroxy and 4-(2-fluoroethoxy) aromatic substituents: Potent and selective inhibitors of [(3)H]dopamine uptake at the vesicular monoamine transporter-2. Bioorganic & medicinal chemistry letters. 2016 05; 26(10):2422-2427. doi: 10.1016/j.bmcl.2016.03.119. [PMID: 27080180]
  • László Kursinszki, Éva Szőke. HPLC-ESI-MS/MS of brain neurotransmitter modulator lobeline and related piperidine alkaloids in Lobelia inflata L. Journal of mass spectrometry : JMS. 2015 May; 50(5):727-33. doi: 10.1002/jms.3581. [PMID: 26259655]
  • Martina Kaniakova, Kristyna Skrenkova, Svatopluk Adamek, Frantisek Vyskocil, Jan Krusek. Different effects of lobeline on neuronal and muscle nicotinic receptors. European journal of pharmacology. 2014 Sep; 738(?):352-9. doi: 10.1016/j.ejphar.2014.05.057. [PMID: 24929055]
  • Liana Dantas da Costa E Silva, Laise Carla Lima Verde Rodrigues, Viviane Ramos Dos Santos, Mariangela da Costa Allgayer, Alexandre de Barros Falcão Ferraz, Helena Campos Rolla, Patrícia Pereira, Jaqueline Nascimento Picada. Evaluation of mutagenic and genotoxic activities of lobeline and its modulation on genomic instability induced by ethanol. Life sciences. 2014 May; 103(2):73-8. doi: 10.1016/j.lfs.2014.03.034. [PMID: 24727238]
  • Benedict T Green, Stephen T Lee, Kevin D Welch, James A Pfister, Kip E Panter. Piperidine, pyridine alkaloid inhibition of fetal movement in a day 40 pregnant goat model. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Aug; 58(?):8-13. doi: 10.1016/j.fct.2013.04.009. [PMID: 23603380]
  • Monzurul Amin Roni, Shafiqur Rahman. Antidepressant-like effects of lobeline in mice: behavioral, neurochemical, and neuroendocrine evidence. Progress in neuro-psychopharmacology & biological psychiatry. 2013 Mar; 41(?):44-51. doi: 10.1016/j.pnpbp.2012.11.011. [PMID: 23200829]
  • Abrar M Tamboli, Rukhsana A Rub, Pinaki Ghosh, S L Bodhankar. Antiepileptic activity of lobeline isolated from the leaf of Lobelia nicotianaefolia and its effect on brain GABA level in mice. Asian Pacific journal of tropical biomedicine. 2012 Jul; 2(7):537-42. doi: 10.1016/s2221-1691(12)60092-6. [PMID: 23569966]
  • Paula V Cabrera, Mabel Pang, Jamie L Marshall, Raymond Kung, Stanley F Nelson, Stephanie H Stalnaker, Lance Wells, Rachelle H Crosbie-Watson, Linda G Baum. High throughput screening for compounds that alter muscle cell glycosylation identifies new role for N-glycans in regulating sarcolemmal protein abundance and laminin binding. The Journal of biological chemistry. 2012 Jun; 287(27):22759-70. doi: 10.1074/jbc.m111.334581. [PMID: 22570487]
  • A M Smith, K A Wellmann, T M Lundblad, M L Carter, S Barron, L P Dwoskin. Lobeline attenuates neonatal ethanol-mediated changes in hyperactivity and dopamine transporter function in the prefrontal cortex in rats. Neuroscience. 2012 Mar; 206(?):245-54. doi: 10.1016/j.neuroscience.2011.11.018. [PMID: 22119644]
  • Amy L Parachnowitsch, Christina M Caruso, Stuart A Campbell, André Kessler. Lobelia siphilitica plants that escape herbivory in time also have reduced latex production. PloS one. 2012; 7(5):e37745. doi: 10.1371/journal.pone.0037745. [PMID: 22662205]
  • David B Horton, Kiran B Siripurapu, Guangrong Zheng, Peter A Crooks, Linda P Dwoskin. Novel N-1,2-dihydroxypropyl analogs of lobelane inhibit vesicular monoamine transporter-2 function and methamphetamine-evoked dopamine release. The Journal of pharmacology and experimental therapeutics. 2011 Oct; 339(1):286-97. doi: 10.1124/jpet.111.184770. [PMID: 21778282]
  • Adak Nasiripourdori, Valérie Taly, Thomas Grutter, Antoine Taly. From toxins targeting ligand gated ion channels to therapeutic molecules. Toxins. 2011 03; 3(3):260-93. doi: 10.3390/toxins3030260. [PMID: 22069709]
  • Paraskevi Krashia, Mirko Moroni, Steven Broadbent, Giovanna Hofmann, Sebastian Kracun, Marco Beato, Paul J Groot-Kormelink, Lucia G Sivilotti. Human α3β4 neuronal nicotinic receptors show different stoichiometry if they are expressed in Xenopus oocytes or mammalian HEK293 cells. PloS one. 2010 Oct; 5(10):e13611. doi: 10.1371/journal.pone.0013611. [PMID: 21049012]
  • Imju Jeong, Bok Hee Choi, Sang June Hahn. Effects of lobeline, a nicotinic receptor ligand, on the cloned Kv1.5. Pflugers Archiv : European journal of physiology. 2010 Oct; 460(5):851-62. doi: 10.1007/s00424-010-0868-3. [PMID: 20734202]
  • Justin R Nickell, Sairam Krishnamurthy, Seth Norrholm, Gabriela Deaciuc, Kiran B Siripurapu, Guangrong Zheng, Peter A Crooks, Linda P Dwoskin. Lobelane inhibits methamphetamine-evoked dopamine release via inhibition of the vesicular monoamine transporter-2. The Journal of pharmacology and experimental therapeutics. 2010 Feb; 332(2):612-21. doi: 10.1124/jpet.109.160275. [PMID: 19855096]
  • Rong-Jane Chen, Yuan-Soon Ho, How-Ran Guo, Ying-Jan Wang. Rapid activation of Stat3 and ERK1/2 by nicotine modulates cell proliferation in human bladder cancer cells. Toxicological sciences : an official journal of the Society of Toxicology. 2008 Aug; 104(2):283-93. doi: 10.1093/toxsci/kfn086. [PMID: 18448488]
  • Junichi Kitanaka. [Toxicity of an alkaloid extracted from the plant Lobelia inflata: association with methamphetamine-induced behavioral abnormalities]. Chudoku kenkyu : Chudoku Kenkyukai jun kikanshi = The Japanese journal of toxicology. 2008 Apr; 21(2):189-91. doi: ". [PMID: 18516945]
  • Clare J Wilhelm, Robert A Johnson, Amy J Eshleman, Aaron Janowsky. Lobeline effects on tonic and methamphetamine-induced dopamine release. Biochemical pharmacology. 2008 Mar; 75(6):1411-5. doi: 10.1016/j.bcp.2007.11.019. [PMID: 18191815]
  • Jing-Jing Wang, Shang-Ming Liu, Rong Chen, Li Li, Xiao-Sun Guo, Bing Xue, Wei-Cheng Hu. A novel effect of lobeline on vascular smooth muscle cell: inhibition of proliferation induced by endothelin-1. Die Pharmazie. 2007 Aug; 62(8):620-4. doi: . [PMID: 17867559]
  • Guangrong Zheng, David B Horton, Agripina G Deaciuc, Linda P Dwoskin, Peter A Crooks. Des-keto lobeline analogs with increased potency and selectivity at dopamine and serotonin transporters. Bioorganic & medicinal chemistry letters. 2006 Oct; 16(19):5018-21. doi: 10.1016/j.bmcl.2006.07.070. [PMID: 16905316]
  • Ramón Aguiar, Michael Wink. Do naïve ruminants degrade alkaloids in the rumen?. Journal of chemical ecology. 2005 Apr; 31(4):761-87. doi: 10.1007/s10886-005-3543-y. [PMID: 16124250]
  • Dennis K Miller, Peter A Crooks, Guangrong Zheng, Vladimir P Grinevich, Seth D Norrholm, Linda P Dwoskin. Lobeline analogs with enhanced affinity and selectivity for plasmalemma and vesicular monoamine transporters. The Journal of pharmacology and experimental therapeutics. 2004 Sep; 310(3):1035-45. doi: 10.1124/jpet.104.068098. [PMID: 15121762]
  • Clare J Wilhelm, Robert A Johnson, Paul G Lysko, Amy J Eshleman, Aaron Janowsky. Effects of methamphetamine and lobeline on vesicular monoamine and dopamine transporter-mediated dopamine release in a cotransfected model system. The Journal of pharmacology and experimental therapeutics. 2004 Sep; 310(3):1142-51. doi: 10.1124/jpet.104.067314. [PMID: 15102929]
  • David E Dussourd. Chemical stimulants of leaf-trenching by cabbage loopers: natural products, neurotransmitters, insecticides, and drugs. Journal of chemical ecology. 2003 Sep; 29(9):2023-47. doi: 10.1023/a:1025630301162. [PMID: 14584674]
  • C Reavill, B Walther, I P Stolerman, B Testa. Behavioural and pharmacokinetic studies on nicotine, cytisine and lobeline. Neuropharmacology. 1990 Jul; 29(7):619-24. doi: 10.1016/0028-3908(90)90022-j. [PMID: 2385332]
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  • A Krochmal, L Wilken, M Chien. Lobeline content of four Appalachian lobelias. Lloydia. 1972 Sep; 35(3):303-4. doi: ". [PMID: 5086292]
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