Tetrahydroalstonine (BioDeep_00000014345)

Main id: BioDeep_00000230026

 

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


Tetrahydroalstonine

化学式: C21H24N2O3 (352.17868339999995)
中文名称: 四氢鸭脚木碱
谱图信息: 最多检出来源 Viridiplantae(plant) 97.06%

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

Annotation level-1
D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents
CASMI2013 Challenge_14 MS2 data

同义名列表

2 个代谢物同义名

Tetrahydroalstonine; Tetrahydroalstonine



数据库引用编号

40 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)

90 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • Vincent Courdavault, Vincent Burlat, Benoit St-Pierre, Nathalie Giglioli-Guivarc'h. Proteins prenylated by type I protein geranylgeranyltransferase act positively on the jasmonate signalling pathway triggering the biosynthesis of monoterpene indole alkaloids in Catharanthus roseus. Plant cell reports. 2009 Jan; 28(1):83-93. doi: 10.1007/s00299-008-0610-1. [PMID: 18813931]
  • C Abdul Jaleel, B Sankar, P V Murali, M Gomathinayagam, G M A Lakshmanan, R Panneerselvam. Water deficit stress effects on reactive oxygen metabolism in Catharanthus roseus; impacts on ajmalicine accumulation. Colloids and surfaces. B, Biointerfaces. 2008 Mar; 62(1):105-11. doi: 10.1016/j.colsurfb.2007.09.026. [PMID: 17996429]
  • C Abdul Jaleel, P Manivannan, B Sankar, A Kishorekumar, R Gopi, R Somasundaram, R Panneerselvam. Induction of drought stress tolerance by ketoconazole in Catharanthus roseus is mediated by enhanced antioxidant potentials and secondary metabolite accumulation. Colloids and surfaces. B, Biointerfaces. 2007 Nov; 60(2):201-6. doi: 10.1016/j.colsurfb.2007.06.010. [PMID: 17643970]
  • C Abdul Jaleel, P Manivannan, B Sankar, A Kishorekumar, R Gopi, R Somasundaram, R Panneerselvam. Pseudomonas fluorescens enhances biomass yield and ajmalicine production in Catharanthus roseus under water deficit stress. Colloids and surfaces. B, Biointerfaces. 2007 Oct; 60(1):7-11. doi: 10.1016/j.colsurfb.2007.05.012. [PMID: 17681765]
  • Carolyn W T Lee-Parsons, Amber J Royce. Precursor limitations in methyl jasmonate-induced Catharanthus roseus cell cultures. Plant cell reports. 2006 Jun; 25(6):607-12. doi: 10.1007/s00299-005-0109-y. [PMID: 16432630]
  • 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]
  • Akira Iwase, Hideki Aoyagi, Masaru Ohme-Takagi, Hideo Tanaka. Development of a novel system for producing ajmalicine and serpentine using direct culture of leaves in Catharanthus roseus intact plant. Journal of bioscience and bioengineering. 2005 Mar; 99(3):208-15. doi: 10.1263/jbb.99.208. [PMID: 16233779]
  • Martine Courtois, Zoia Mincheva, Françoise Andreu, Marc Rideau, Marie-Claude Viaud-Massuard. Synthesis and biological evaluation with plant cells of new fosmidomycin analogues containing a benzoxazolone or oxazolopyridinone ring. Journal of enzyme inhibition and medicinal chemistry. 2004 Dec; 19(6):559-65. doi: 10.1080/14756360400004615. [PMID: 15662959]
  • Jyoti Batra, Ajaswrata Dutta, Digvijay Singh, Sushil Kumar, Jayanti Sen. Growth and terpenoid indole alkaloid production in Catharanthus roseus hairy root clones in relation to left- and right-termini-linked Ri T-DNA gene integration. Plant cell reports. 2004 Sep; 23(3):148-54. doi: 10.1007/s00299-004-0815-x. [PMID: 15221274]
  • Felipe Vázquez-Flota, Mildred Carrillo-Pech, Yereni Minero-García, María De Lourdes Miranda-Ham. Alkaloid metabolism in wounded Catharanthus roseus seedlings. Plant physiology and biochemistry : PPB. 2004 Jul; 42(7-8):623-8. doi: 10.1016/j.plaphy.2004.06.010. [PMID: 15331091]
  • M A Favali, R Musetti, S Benvenuti, A Bianchi, L Pressacco. Catharanthus roseus L. plants and explants infected with phytoplasmas: alkaloid production and structural observations. Protoplasma. 2004 Mar; 223(1):45-51. doi: 10.1007/s00709-003-0024-4. [PMID: 15004742]
  • Ramesh K Satdive, Devanand P Fulzele, Susan Eapen. Studies on production of ajmalicine in shake flasks by multiple shoot cultures of Catharanthus roseus. Biotechnology progress. 2003 May; 19(3):1071-5. doi: 10.1021/bp020138g. [PMID: 12790683]
  • C G Sudha, B Obul Reddy, G A Ravishankar, S Seeni. Production of ajmalicine and ajmaline in hairy root cultures of Rauvolfia micrantha Hook f., a rare and endemic medicinal plant. Biotechnology letters. 2003 Apr; 25(8):631-6. doi: 10.1023/a:1023012114628. [PMID: 12882157]
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  • C W Lee, M L Shuler. The effect of inoculum density and conditioned medium on the production of ajmalicine and catharanthine from immobilized Catharanthus roseus cells. Biotechnology and bioengineering. 2000 Jan; 67(1):61-71. doi: 10.1002/(sici)1097-0290(20000105)67:1<61::aid-bit7>3.0.co;2-j. [PMID: 10581436]
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  • R Bhadra, J A Morgan, J V Shanks. Transient studies of light-adapted cultures of hairy roots of Catharanthus roseus: growth and indole alkaloid accumulation. Biotechnology and bioengineering. 1998 Dec; 60(6):670-8. doi: 10.1002/(sici)1097-0290(19981220)60:6<670::aid-bit4>3.0.co;2-j. [PMID: 10099477]
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