Ajmalicine (BioDeep_00000000513)

 

Secondary id: BioDeep_00000408335

PANOMIX_OTCML-2023


代谢物信息卡片


methyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7,18-pentaene-19-carboxylate

化学式: C21H24N2O3 (352.17868339999995)
中文名称: 阿吗里新, 萝巴新, 萝巴新
谱图信息: 最多检出来源 Viridiplantae(plant) 0.51%

分子结构信息

SMILES: CC1C2CN3CCC4=C(C3CC2C(=CO1)C(=O)OC)NC5=CC=CC=C45
InChI: InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3

描述信息

Ajmalicine is a monoterpenoid indole alkaloid with formula C21H24N2O3, isolated from several Rauvolfia and Catharanthus species. It is a selective alpha1-adrenoceptor antagonist used for the treatment of high blood pressure. It has a role as an antihypertensive agent, an alpha-adrenergic antagonist and a vasodilator agent. It is a monoterpenoid indole alkaloid, a methyl ester and an organic heteropentacyclic compound. It is a conjugate base of an ajmalicine(1+).
Ajmalicine is a natural product found in Crossosoma bigelovii, Rauvolfia yunnanensis, and other organisms with data available.
A monoterpenoid indole alkaloid with formula C21H24N2O3, isolated from several Rauvolfia and Catharanthus species. It is a selective alpha1-adrenoceptor antagonist used for the treatment of high blood pressure.
D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents
INTERNAL_ID 2326; CONFIDENCE Reference Standard (Level 1)
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2326
[Raw Data] CB001_Ajmalicine_pos_40eV_CB000004.txt
[Raw Data] CB001_Ajmalicine_pos_10eV_CB000004.txt
[Raw Data] CB001_Ajmalicine_pos_50eV_CB000004.txt
[Raw Data] CB001_Ajmalicine_pos_20eV_CB000004.txt
[Raw Data] CB001_Ajmalicine_pos_30eV_CB000004.txt
Ajmalicine (Raubasine) is a potent adrenolytic agent which preferentially blocks α1-adrenoceptor. Ajmalicine is an reversible but non-competitive nicotine receptor full inhibitor, with an IC50 of 72.3 μM. Ajmalicine also can be used as anti-hypertensive, and serpentine, with sedative activity[1][2].
Ajmalicine (Raubasine) is a potent adrenolytic agent which preferentially blocks α1-adrenoceptor. Ajmalicine is an reversible but non-competitive nicotine receptor full inhibitor, with an IC50 of 72.3 μM. Ajmalicine also can be used as anti-hypertensive, and serpentine, with sedative activity[1][2].
Ajmalicine (Raubasine) is a potent adrenolytic agent which preferentially blocks α1-adrenoceptor. Ajmalicine is an reversible but non-competitive nicotine receptor full inhibitor, with an IC50 of 72.3 μM. Ajmalicine also can be used as anti-hypertensive, and serpentine, with sedative activity[1][2].

同义名列表

79 个代谢物同义名

methyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7,18-pentaene-19-carboxylate; methyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate; (7aR,8S,11aS,12aS)-8-Methyl-5,6,7a,8,11a,12,12a,13-octahydro-7H-9-oxa-6a,13-diaza-indeno[2,1-a]anthracene-11-carboxylic acid methyl ester; methyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate; methyl (4S,4aR,13bS,14aS)-4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylate; (4S,4aR,13bS,14aS)-methyl 4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylate; Methyl (19-methyl-16,17-dehydro-18-oxa-3alpha,15alpha,19beta,20beta-yohimban-16-carboxylat); Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (19-.alpha).-; Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (19-alpha)-; (19.ALPHA.)-16,17-DIDEHYDRO-19-METHYLOXAYOHIMBAN-16-CARBOXYLIC ACID METHYL ESTER; (19alpha)-16,17-Didehydro-19-methyl-oxayohimban-16-carboxylic acid methyl ester; Oxayohimban-16-carboxylicacid, 16,17-didehydro-19-methyl-, methyl ester, (19a)-; Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methylester, (19a)-; methyl (19alpha)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate; Methyl (19alpha)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate; 16,17-Didehydro-19-methyloxayohimban-16-carboxylic acid methyl ester; methyl (19alpha)-19-methyl-16,17-didehydrooxayohimban-16-carboxylate; Methyl 16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylat; 19b-methyl-16-methoxycarbonyl-16,17-didehydro-oxayohimbane; ajmalicine, (hydrochloride(19beta,20alpha))-isomer; [2,3-a]pyrano[3,4-g]quinolizine-1-carboxylate; 4-27-00-07927 (Beilstein Handbook Reference); ajmalicine, (3beta,19alpha,20alpha)-isomer; 4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo; ajmalicine, hydrochloride(19alpha)-isomer; ajmalicine, (19alpha,20alpha)-isomer; ajmalicine, (19beta,20alpha)-isomer; (4S,4aR,13bS,14aS)-methyl 4-methyl-; ajmalicine, (3beta,19alpha)-isomer; ajmalicine, (3-beta,19beta)-isomer; ajmalicine, PO4(19alpha)-isomer; ajmalicine, (19beta)-isomer; GRTOGORTSDXSFK-XJTZBENFSA-N; ajmalicine hydrochloride; raubasine hydrochloride; Ajmalicine(-Yohimbine); PYTETRAHYDROSERPENTINE; Tetrahydroserpentine; tetrahydro-alstonine; Tetrahydroalstonine; RAUBASINE [WHO-DD]; rauwolfia alkaloid; Prestwick3_000592; RAUBASINE [MART.]; .delta.-Yohimbine; Prestwick1_000592; Prestwick0_000592; Prestwick2_000592; 19-epiajmalicine; delta-yohimbine; Raubasine (DCF); UNII-4QJL8OX71Z; RAUBASINE [MI]; DivK1c_006521; BPBio1_000512; Raubasine,(S); raubasine HCl; MEGxp0_001818; KBio2_001255; KBio2_006391; ACon1_001630; Substance II; Lamuran (TN); KBio2_003823; KBio1_001465; Hydrosarpan; akuammigine; 4QJL8OX71Z; ajmalicine; Isoarteril; Cristanyl; Ajmalicin; raubasine; Circolene; rauvasan; Lamuran; Sarpan; AJN; Mayumbine



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(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)

41 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

  • Kang Chen, Guran Yu. Tetrahydroalstonine possesses protective potentials on palmitic acid stimulated SK-N-MC cells by suppression of Aβ1-42 and tau through regulation of PI3K/Akt signaling pathway. European journal of pharmacology. 2024 Jan; 962(?):176251. doi: 10.1016/j.ejphar.2023.176251. [PMID: 38061471]
  • Sachin Kumar Verma, Danswrang Goyary, Amit Kumar Singh, Sivalingam Anandhan, Soom Nath Raina, Sadanand Pandey, Shailesh Kumar, Neeraj Khare. Modulation of terpenoid indole alkaloid pathway via elicitation with phytosynthesized silver nanoparticles for the enhancement of ajmalicine, a pharmaceutically important alkaloid. Planta. 2023 Dec; 259(2):30. doi: 10.1007/s00425-023-04311-z. [PMID: 38150044]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Tengfei Liu, Yuanwei Gou, Bei Zhang, Rui Gao, Chang Dong, Mingming Qi, Lihong Jiang, Xuanwei Ding, Chun Li, Jiazhang Lian. Construction of ajmalicine and sanguinarine de novo biosynthetic pathways using stable integration sites in yeast. Biotechnology and bioengineering. 2022 05; 119(5):1314-1326. doi: 10.1002/bit.28040. [PMID: 35060115]
  • Shyam H Kamble, Erin C Berthold, Tamara I King, Siva Rama Raju Kanumuri, Raluca Popa, Julius R Herting, Francisco León, Abhisheak Sharma, Lance R McMahon, Bonnie A Avery, Christopher R McCurdy. Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats. Journal of natural products. 2021 04; 84(4):1104-1112. doi: 10.1021/acs.jnatprod.0c01163. [PMID: 33620222]
  • Priya Kashyap, Vivekanandan Kalaiselvan, Robin Kumar, Suresh Kumar. Ajmalicine and Reserpine: Indole Alkaloids as Multi-Target Directed Ligands Towards Factors Implicated in Alzheimer's Disease. Molecules (Basel, Switzerland). 2020 Apr; 25(7):. doi: 10.3390/molecules25071609. [PMID: 32244635]
  • S Singh, S S Pandey, K Shanker, A Kalra. Endophytes enhance the production of root alkaloids ajmalicine and serpentine by modulating the terpenoid indole alkaloid pathway in Catharanthus roseus roots. Journal of applied microbiology. 2020 Apr; 128(4):1128-1142. doi: 10.1111/jam.14546. [PMID: 31821696]
  • Thomas J Flynn, Sanah N Vohra. Simultaneous determination of intestinal permeability and potential drug interactions of complex mixtures using Caco-2 cells and high-resolution mass spectrometry: Studies with Rauwolfia serpentina extract. Chemico-biological interactions. 2018 Jun; 290(?):37-43. doi: 10.1016/j.cbi.2018.05.006. [PMID: 29782822]
  • Yang Qu, Antje M K Thamm, Matthew Czerwinski, Sayaka Masada, Kyung Hee Kim, Graham Jones, Ping Liang, Vincenzo De Luca. Geissoschizine synthase controls flux in the formation of monoterpenoid indole alkaloids in a Catharanthus roseus mutant. Planta. 2018 Mar; 247(3):625-634. doi: 10.1007/s00425-017-2812-7. [PMID: 29147812]
  • Xiao-Ning Zhang, Jia Liu, Yang Liu, Yu Wang, Ann Abozeid, Zhi-Guo Yu, Zhong-Hua Tang. Metabolomics Analysis Reveals that Ethylene and Methyl Jasmonate Regulate Different Branch Pathways to Promote the Accumulation of Terpenoid Indole Alkaloids in Catharanthus roseus. Journal of natural products. 2018 02; 81(2):335-342. doi: 10.1021/acs.jnatprod.7b00782. [PMID: 29406718]
  • Roukia Benyammi, Cédric Paris, Majda Khelifi-Slaoui, Djamila Zaoui, Ouarda Belabbassi, Nouara Bakiri, Myassa Meriem Aci, Boualem Harfi, Sonia Malik, Abdullah Makhzoum, Stéphane Desobry, Lakhdar Khelifi. Screening and kinetic studies of catharanthine and ajmalicine accumulation and their correlation with growth biomass in Catharanthus roseus hairy roots. Pharmaceutical biology. 2016 Oct; 54(10):2033-43. doi: 10.3109/13880209.2016.1140213. [PMID: 26983347]
  • Gui-Guang Cheng, Dan Li, Bo Hou, Xiao-Nian Li, Lu Liu, Ying-Ying Chen, Paul-Keilah Lunga, Afsar Khan, Ya-Ping Liu, Zhi-Li Zuo, Xiao-Dong Luo. Melokhanines A-J, Bioactive Monoterpenoid Indole Alkaloids with Diverse Skeletons from Melodinus khasianus. Journal of natural products. 2016 09; 79(9):2158-66. doi: 10.1021/acs.jnatprod.6b00011. [PMID: 27584856]
  • Kotaro Yamamoto, Katsutoshi Takahashi, Hajime Mizuno, Aya Anegawa, Kimitsune Ishizaki, Hidehiro Fukaki, Miwa Ohnishi, Mami Yamazaki, Tsutomu Masujima, Tetsuro Mimura. Cell-specific localization of alkaloids in Catharanthus roseus stem tissue measured with Imaging MS and Single-cell MS. Proceedings of the National Academy of Sciences of the United States of America. 2016 Apr; 113(14):3891-6. doi: 10.1073/pnas.1521959113. [PMID: 27001858]
  • Pengfei Zhou, Jiazeng Yang, Jianhua Zhu, Shuijie He, Wenjin Zhang, Rongmin Yu, Jiachen Zi, Liyan Song, Xuesong Huang. Effects of β-cyclodextrin and methyl jasmonate on the production of vindoline, catharanthine, and ajmalicine in Catharanthus roseus cambial meristematic cell cultures. Applied microbiology and biotechnology. 2015 Sep; 99(17):7035-45. doi: 10.1007/s00253-015-6651-9. [PMID: 25981997]
  • Anna Stavrinides, Evangelos C Tatsis, Emilien Foureau, Lorenzo Caputi, Franziska Kellner, Vincent Courdavault, Sarah E O'Connor. Unlocking the diversity of alkaloids in Catharanthus roseus: nuclear localization suggests metabolic channeling in secondary metabolism. Chemistry & biology. 2015 Mar; 22(3):336-41. doi: 10.1016/j.chembiol.2015.02.006. [PMID: 25772467]
  • Yanan Gai, Han Chen, Wenyuan Liu, Feng Feng, Ning Xie. The metabolism of YiGan San and subsequent pharmacokinetic evaluation of four metabolites in rat based on liquid chromatography with tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Dec; 972(?):22-8. doi: 10.1016/j.jchromb.2014.09.033. [PMID: 25306115]
  • Francisco Fernández-Pérez, Lorena Almagro, Maria A Pedreño, Laura V Gómez Ros. Synergistic and cytotoxic action of indole alkaloids produced from elicited cell cultures of Catharanthus roseus. Pharmaceutical biology. 2013 Mar; 51(3):304-10. doi: 10.3109/13880209.2012.722646. [PMID: 23137274]
  • Wanhong Liu, Rong Chen, Min Chen, Haoxing Zhang, Meifang Peng, Chunxian Yang, Xingjia Ming, Xiaozhong Lan, Zhihua Liao. Tryptophan decarboxylase plays an important role in ajmalicine biosynthesis in Rauvolfia verticillata. Planta. 2012 Jul; 236(1):239-50. doi: 10.1007/s00425-012-1608-z. [PMID: 22331368]
  • Bo Hong, Wen-Jing Li, Chun-Jie Zhao. [Chemical constituents of Rauvolfia verticillata]. Yao xue xue bao = Acta pharmaceutica Sinica. 2012 Jun; 47(6):764-8. doi: . [PMID: 22919724]
  • Vishakha Sharma, Swati Chaudhary, Suchi Srivastava, Richa Pandey, Sushil Kumar. Characterization of variation and quantitative trait loci related to terpenoid indole alkaloid yield in a recombinant inbred line mapping population of Catharanthus roseus. Journal of genetics. 2012; 91(1):49-69. doi: . [PMID: 22546825]
  • Qifang Pan, Quan Wang, Fang Yuan, Shihai Xing, Jingya Zhao, Young Hae Choi, Robert Verpoorte, Yuesheng Tian, Guofeng Wang, Kexuan Tang. Overexpression of ORCA3 and G10H in Catharanthus roseus plants regulated alkaloid biosynthesis and metabolism revealed by NMR-metabolomics. PloS one. 2012; 7(8):e43038. doi: 10.1371/journal.pone.0043038. [PMID: 22916202]
  • Guilherme Guimarães, Luísa Cardoso, Helena Oliveira, Conceição Santos, Patrícia Duarte, Mariana Sottomayor. Cytogenetic characterization and genome size of the medicinal plant Catharanthus roseus (L.) G. Don. AoB PLANTS. 2012; 2012(?):pls002. doi: 10.1093/aobpla/pls002. [PMID: 22479673]
  • Mai Li, Christie A M Peebles, Jacqueline V Shanks, Ka-Yiu San. Effect of sodium nitroprusside on growth and terpenoid indole alkaloid production in Catharanthus roseus hairy root cultures. Biotechnology progress. 2011 May; 27(3):625-30. doi: 10.1002/btpr.605. [PMID: 21567990]
  • J S Thakur, R K Agarwal, M D Kharya. Enhancing hepatoprotective bioactives of phyllanthus amarus through immobilization by growth promoters and media changes. Indian journal of pharmaceutical sciences. 2011 May; 73(3):271-5. doi: 10.4103/0250-474x.93510. [PMID: 22457549]
  • Monika Jaggi, Santosh Kumar, Alok Krishna Sinha. Overexpression of an apoplastic peroxidase gene CrPrx in transgenic hairy root lines of Catharanthus roseus. Applied microbiology and biotechnology. 2011 May; 90(3):1005-16. doi: 10.1007/s00253-011-3131-8. [PMID: 21318361]
  • Mohammad Jamshed Ahmad Siddiqui, Zhari Ismail, Noor Hafizoh Saidan. Simultaneous determination of secondary metabolites from Vinca rosea plant extractives by reverse phase high performance liquid chromatography. Pharmacognosy magazine. 2011 Apr; 7(26):92-6. doi: 10.4103/0973-1296.80662. [PMID: 21716929]
  • Christie A M Peebles, Guy W Sander, Erik H Hughes, Ryan Peacock, Jacqueline V Shanks, Ka-Yiu San. The expression of 1-deoxy-D-xylulose synthase and geraniol-10-hydroxylase or anthranilate synthase increases terpenoid indole alkaloid accumulation in Catharanthus roseus hairy roots. Metabolic engineering. 2011 Mar; 13(2):234-40. doi: 10.1016/j.ymben.2010.11.005. [PMID: 21144909]
  • L Almagro, A J López Perez, M A Pedreño. New method to enhance ajmalicine production in Catharanthus roseus cell cultures based on the use of cyclodextrins. Biotechnology letters. 2011 Feb; 33(2):381-5. doi: 10.1007/s10529-010-0430-6. [PMID: 20953668]
  • Lihong He, Li Yang, Aizhen Xiong, Shujuan Zhao, Zhengtao Wang, Zhibi Hu. Simultaneous quantification of four indole alkaloids in Catharanthus roseus cell line C20hi by UPLC-MS. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2011; 27(4):433. doi: 10.2116/analsci.27.433. [PMID: 21478621]
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  • Barbora Pomahacová, Jaroslav Dusek, Jirina Dusková, Kazufumi Yazaki, Sittiruk Roytrakul, Robert Verpoorte. Improved accumulation of ajmalicine and tetrahydroalstonine in Catharanthus cells expressing an ABC transporter. Journal of plant physiology. 2009 Sep; 166(13):1405-12. doi: 10.1016/j.jplph.2009.02.015. [PMID: 19403195]
  • Shijun Lu, Buu N Tran, Jamie L Nelsen, Kenneth M Aldous. Quantitative analysis of mitragynine in human urine by high performance liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Aug; 877(24):2499-505. doi: 10.1016/j.jchromb.2009.06.024. [PMID: 19577523]
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  • Bernard Y K Binder, Christie A M Peebles, Jacqueline V Shanks, Ka-Yiu San. The effects of UV-B stress on the production of terpenoid indole alkaloids in Catharanthus roseus hairy roots. Biotechnology progress. 2009 May; 25(3):861-5. doi: 10.1002/btpr.97. [PMID: 19479674]
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