Ajmalicine (BioDeep_00000175795)

   

human metabolite blood metabolite natural product


代谢物信息卡片


Methyl 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-carboxylic acid

化学式: C21H24N2O3 (352.17868339999995)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 3.13%

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

D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents

同义名列表

24 个代谢物同义名

Methyl 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-carboxylic acid; methyl 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 16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0,.0,.0,]henicosa-2(10),4,6,8,18-pentaene-19-carboxylic acid; ajmalicine, (hydrochloride(19beta,20alpha))-isomer; ajmalicine, (3beta,19alpha,20alpha)-isomer; ajmalicine, hydrochloride(19alpha)-isomer; ajmalicine, (19alpha,20alpha)-isomer; ajmalicine, (19beta,20alpha)-isomer; ajmalicine, (3beta,19alpha)-isomer; ajmalicine, (3-beta,19beta)-isomer; ajmalicine, PO4(19alpha)-isomer; ajmalicine, (19beta)-isomer; ajmalicine hydrochloride; raubasine hydrochloride; tetrahydro-alstonine; Tetrahydroalstonine; 19-epiajmalicine; delta-yohimbine; raubasine HCl; akuammigine; ajmalicine; raubasine; rauvasan; Lamuran



数据库引用编号

5 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)

117 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • Weerawat Runguphan, Xudong Qu, Sarah E O'Connor. Integrating carbon-halogen bond formation into medicinal plant metabolism. Nature. 2010 Nov; 468(7322):461-4. doi: 10.1038/nature09524. [PMID: 21048708]
  • N K Srivastava, A K Srivastava. Influence of Some Heavy Metals on Growth, Alkaloid Content and Composition in Catharanthus roseus L. Indian journal of pharmaceutical sciences. 2010 Nov; 72(6):775-8. doi: 10.4103/0250-474x.84592. [PMID: 21969751]
  • 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]
  • David M Pereira, Federico Ferreres, Jorge M A Oliveira, Luís Gaspar, Joana Faria, Patrícia Valentão, Mariana Sottomayor, Paula B Andrade. Pharmacological effects of Catharanthus roseus root alkaloids in acetylcholinesterase inhibition and cholinergic neurotransmission. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2010 Jul; 17(8-9):646-52. doi: 10.1016/j.phymed.2009.10.008. [PMID: 19962870]
  • Joachim Stockigt, Bodo Hammes, Martin Ruppert. Construction and expression of a dual vector for chemo-enzymatic synthesis of plant indole alkaloids in Escherichia coli. Natural product research. 2010 May; 24(8):759-66. doi: 10.1080/14786410903247304. [PMID: 20432158]
  • Jon Anders Stavang, Rolf Inge Pettersen, Micael Wendell, Knut Asbjørn Solhaug, Olavi Junttila, Roar Moe, Jorunn E Olsen. Thermoperiodic growth control by gibberellin does not involve changes in photosynthetic or respiratory capacities in pea. Journal of experimental botany. 2010 Feb; 61(4):1015-29. doi: 10.1093/jxb/erp366. [PMID: 20022920]
  • Federico Ferreres, David M Pereira, Patrícia Valentão, Jorge M A Oliveira, Joana Faria, Luís Gaspar, Mariana Sottomayor, Paula B Andrade. Simple and reproducible HPLC-DAD-ESI-MS/MS analysis of alkaloids in Catharanthus roseus roots. Journal of pharmaceutical and biomedical analysis. 2010 Jan; 51(1):65-9. doi: 10.1016/j.jpba.2009.08.005. [PMID: 19720492]
  • Mohammed Fazil Ahmed, Syed Mohammed Kazim, Syed Safiullah Ghori, Syeda Sughra Mehjabeen, Shaik Rasheed Ahmed, Shaik Mehboob Ali, Mohammed Ibrahim. Antidiabetic Activity of Vinca rosea Extracts in Alloxan-Induced Diabetic Rats. International journal of endocrinology. 2010; 2010(?):841090. doi: 10.1155/2010/841090. [PMID: 20652054]
  • Sheba Goklany, Ralph H Loring, James Glick, Carolyn W T Lee-Parsons. Assessing the limitations to terpenoid indole alkaloid biosynthesis in Catharanthus roseus hairy root cultures through gene expression profiling and precursor feeding. Biotechnology progress. 2009 Sep; 25(5):1289-96. doi: 10.1002/btpr.204. [PMID: 19722248]
  • 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]
  • Francisco León, Eman Habib, Jessica E Adkins, Edward B Furr, Christopher R McCurdy, Stephen J Cutler. Phytochemical characterization of the leaves of Mitragyna speciosa grown in U.S.A. Natural product communications. 2009 Jul; 4(7):907-10. doi: . [PMID: 19731590]
  • Paul Klausmeyer, Qin Zhou, Dominic A Scudiero, Badarch Uranchimeg, Giovanni Melillo, John H Cardellina, Robert H Shoemaker, Ching-Jer Chang, Thomas G McCloud. Cytotoxic and HIF-1alpha inhibitory compounds from Crossosoma bigelovii. Journal of natural products. 2009 May; 72(5):805-12. doi: 10.1021/np8006342. [PMID: 19405508]
  • 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]
  • Felipe Vázquez-Flota, Elizabeta Hernández-Domínguez, Ma de Lourdes Miranda-Ham, Miriam Monforte-González. A differential response to chemical elicitors in Catharanthus roseus in vitro cultures. Biotechnology letters. 2009 Apr; 31(4):591-5. doi: 10.1007/s10529-008-9881-4. [PMID: 19030782]
  • Mei-Liang Zhou, Ji-Rong Shao, Yi-Xiong Tang. Production and metabolic engineering of terpenoid indole alkaloids in cell cultures of the medicinal plant Catharanthus roseus (L.) G. Don (Madagascar periwinkle). Biotechnology and applied biochemistry. 2009 Apr; 52(Pt 4):313-23. doi: 10.1042/ba20080239. [PMID: 19281450]
  • Eliel Ruiz-May, Rosa M Galaz-Avalos, Víctor M Loyola-Vargas. Differential secretion and accumulation of terpene indole alkaloids in hairy roots of Catharanthus roseus treated with methyl jasmonate. Molecular biotechnology. 2009 Mar; 41(3):278-85. doi: 10.1007/s12033-008-9111-2. [PMID: 18841500]
  • Aniça Amini, Gaëlle Glévarec, Françoise Andreu, Marc Rideau, Joël Crèche. Low levels of gibberellic acid control the biosynthesis of ajmalicine in Catharanthus roseus cell suspension cultures. Planta medica. 2009 Feb; 75(2):187-91. doi: 10.1055/s-0028-1112198. [PMID: 19096998]
  • M K Goel, S Mehrotra, A K Kukreja, K Shanker, S P S Khanuja. In vitro propagation of Rauwolfia serpentina using liquid medium, assessment of genetic fidelity of micropropagated plants, and simultaneous quantitation of reserpine, ajmaline, and ajmalicine. Methods in molecular biology (Clifton, N.J.). 2009; 547(?):17-33. doi: 10.1007/978-1-60327-287-2_2. [PMID: 19521832]
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  • Christie A M Peebles, Seung-Beom Hong, Susan I Gibson, Jacqueline V Shanks, Ka-Yiu San. Effects of terpenoid precursor feeding on Catharanthus roseus hairy roots over-expressing the alpha or the alpha and beta subunits of anthranilate synthase. Biotechnology and bioengineering. 2006 Feb; 93(3):534-40. doi: 10.1002/bit.20739. [PMID: 16240438]
  • Carolyn W T Lee-Parsons, Seda Ertürk. Ajmalicine production in methyl jasmonate-induced Catharanthus roseus cell cultures depends on Ca2+ level. Plant cell reports. 2005 Dec; 24(11):677-82. doi: 10.1007/s00299-005-0026-0. [PMID: 16094527]
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  • Zoia Mincheva, Martine Courtois, Françoise Andreu, Marc Rideau, Marie-Claude Viaud-Massuard. Fosmidomycin analogues as inhibitors of monoterpenoid indole alkaloid production in Catharanthus roseus cells. Phytochemistry. 2005 Aug; 66(15):1797-803. doi: 10.1016/j.phytochem.2005.06.002. [PMID: 16054176]
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  • Tepy Usia, Tadashi Watabe, Shigetoshi Kadota, Yasuhiro Tezuka. Cytochrome P450 2D6 (CYP2D6) inhibitory constituents of Catharanthus roseus. Biological & pharmaceutical bulletin. 2005 Jun; 28(6):1021-4. doi: 10.1248/bpb.28.1021. [PMID: 15930738]
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