Dehydroevodiamine (BioDeep_00000178030)

   

human metabolite PANOMIX_OTCML-2023 blood metabolite natural product


代谢物信息卡片


21-methyl-3,13,21-triazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-1,3,5,7,9,15,17,19-octaen-14-one

化学式: C19H15N3O (301.121506)
中文名称: 去氢吴茱萸碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 21.35%

分子结构信息

SMILES: CN1C2=C3N=c4ccccc4=C3CCN2C(=O)c2ccccc21
InChI: InChI=1S/C19H15N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9H,10-11H2,1H3

描述信息

同义名列表

3 个代谢物同义名

21-methyl-3,13,21-triazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-1,3,5,7,9,15,17,19-octaen-14-one; dehydroevodiamine chloride; Dehydroevodiamine



数据库引用编号

4 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)

5 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

  • Min Xu, Yalin Zhao, Mingjie Gong, Ziyang He, Wenhua Wang, Yunjuan Li, Weiwei Zhai, Zhengquan Yu. Dehydroevodiamine ameliorates neurological dysfunction after traumatic brain injury in mice via regulating the SIRT1/FOXO3a/Bim pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 Mar; 125(?):155321. doi: 10.1016/j.phymed.2023.155321. [PMID: 38237514]
  • Xin Wang, Lei Chang, Lisheng Chen, Yong He, Tingting He, Ruilin Wang, Shizhang Wei, Manyi Jing, Xuelin Zhou, Haotian Li, Yanling Zhao. Integrated network pharmacology and metabolomics to investigate the effects and possible mechanisms of Dehydroevodiamine against ethanol-induced gastric ulcers. Journal of ethnopharmacology. 2024 Jan; 319(Pt 3):117340. doi: 10.1016/j.jep.2023.117340. [PMID: 37879508]
  • Yufang Dai, Jiaoe Sheng, Sanshan He, Qingchao Wu, Yunlong Wang, Linchong Su. Dehydroevodiamine suppresses inflammatory responses in adjuvant-induced arthritis rats and human fibroblast-like synoviocytes. Bioengineered. 2022 01; 13(1):268-279. doi: 10.1080/21655979.2021.1999554. [PMID: 34719315]
  • Ying Wei, Sichen Ren, Jian Wang, Yanling Wang, Yanfei Cui, Miao Tian, Ruilin Wang, Honghong Liu, Yanling Zhao. Dehydroevodiamine ameliorates indomethacin-induced gastric injury via inhibition of ERK and p38 signaling pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Dec; 93(?):153764. doi: 10.1016/j.phymed.2021.153764. [PMID: 34628242]
  • Jian-Xia Wen, Yu-Ling Tong, Xiao Ma, Rui-Lin Wang, Rui-Sheng Li, Hong-Tao Song, Yan-Ling Zhao. Therapeutic effects and potential mechanism of dehydroevodiamine on N-methyl-N'-nitro-N-nitrosoguanidine-induced chronic atrophic gastritis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Oct; 91(?):153619. doi: 10.1016/j.phymed.2021.153619. [PMID: 34320422]
  • Kun-Ming Tian, Jing-Jie Li, Suo-Wen Xu. Rutaecarpine: A promising cardiovascular protective alkaloid from Evodia rutaecarpa (Wu Zhu Yu). Pharmacological research. 2019 03; 141(?):541-550. doi: 10.1016/j.phrs.2018.12.019. [PMID: 30616017]
  • Youbo Zhang, Tingting Yan, Dongxue Sun, Cen Xie, Yiran Zheng, Lei Zhang, Tomoki Yagai, Kristopher W Krausz, William H Bisson, Xiuwei Yang, Frank J Gonzalez. Structure-Activity Relationships of the Main Bioactive Constituents of Euodia rutaecarpa on Aryl Hydrocarbon Receptor Activation and Associated Bile Acid Homeostasis. Drug metabolism and disposition: the biological fate of chemicals. 2018 07; 46(7):1030-1040. doi: 10.1124/dmd.117.080176. [PMID: 29691238]
  • Igor Baburin, Rosanne Varkevisser, Anja Schramm, Priyanka Saxena, Stanislav Beyl, Phillip Szkokan, Tobias Linder, Anna Stary-Weinzinger, Marcel A G van der Heyden, Marien Houtman, Hiroki Takanari, Malin Jonsson, Jet H D Beekman, Matthias Hamburger, Marc A Vos, Steffen Hering. Dehydroevodiamine and hortiamine, alkaloids from the traditional Chinese herbal drug Evodia rutaecarpa, are IKr blockers with proarrhythmic effects in vitro and in vivo. Pharmacological research. 2018 05; 131(?):150-163. doi: 10.1016/j.phrs.2018.02.024. [PMID: 29477480]
  • Shih-Hurng Loh, Yi-Ting Tsai, Chung-Yi Lee, Chung-Yi Chang, Chien-Sung Tsai, Tzu-Hurng Cheng, Cheng-I Lin. Antiarrhythmic effects of dehydroevodiamine in isolated human myocardium and cardiomyocytes. Journal of ethnopharmacology. 2014 May; 153(3):753-62. doi: 10.1016/j.jep.2014.03.043. [PMID: 24680993]
  • Rui Yan, Yin Wang, Wenjin Shen, Xin Zhao, Xuzhe Zhang. Relative determination of dehydroevodiamine in rat plasma by LC-MS and study on its pharmacokinetics. Journal of chromatographic science. 2012 Aug; 50(7):582-5. doi: 10.1093/chromsci/bms050. [PMID: 22525878]
  • Lie-Chwen Lin, Shang-Hua Li, Yu-Tse Wu, Kuan-Liang Kuo, Tung-Hu Tsai. Pharmacokinetics and urine metabolite identification of dehydroevodiamine in the rat. Journal of agricultural and food chemistry. 2012 Feb; 60(7):1595-604. doi: 10.1021/jf204365m. [PMID: 22283510]
  • Chuan-Qin Hu, Fei Li, Xiu-Wei Yang. Simultaneous determination and pharmacokinetic analysis of seven alkaloids and two flavonoids from rat plasma by HPLC-DAD after oral administration of Wuzhuyu decoction. Journal of Asian natural products research. 2012; 14(4):370-81. doi: 10.1080/10286020.2012.656093. [PMID: 22375876]
  • Chuan-Qin Hu, Ke-Ke Li, Xiu-Wei Yang. New glycosidic alkaloid from the nearly ripe fruits of Euodia rutaecarpa. Journal of Asian natural products research. 2012; 14(7):634-9. doi: 10.1080/10286020.2012.682154. [PMID: 22582827]
  • Rui Yan, Yin Wang, Wenjin Shen, Youping Liu, Xin Di. Comparative pharmacokinetics of dehydroevodiamine and coptisine in rat plasma after oral administration of single herbs and Zuojinwan prescription. Fitoterapia. 2011 Dec; 82(8):1152-9. doi: 10.1016/j.fitote.2011.07.012. [PMID: 21816210]
  • Juanjuan Zhao, Xiao Han, Xu Zhao, Chao Wang, Qing Li, Xiaohui Chen, Kaishun Bi. A sensitive liquid chromatographic-mass spectrometric method for simultaneous determination of dehydroevodiamine and limonin from Evodia rutaecarpa in rat plasma. Analytical and bioanalytical chemistry. 2011 Jul; 401(1):289-96. doi: 10.1007/s00216-011-5072-6. [PMID: 21573727]
  • Yang Zhao, Xin Zhou, Hua-Guo Chen, Xiao-Jian Gong, Zong-Wei Cai, Chan-Yuan Zhou. Determination of dehydroevodiamine in Evodia rutaecarpa (Juss.) Benth by high performance liquid chromatography and classification of the samples by using hierarchical clustering analysis. Fitoterapia. 2009 Oct; 80(7):415-20. doi: 10.1016/j.fitote.2009.05.017. [PMID: 19486930]
  • Xiu-Wei Yang, Jie Teng, Ying Wang, Wei Xu. The permeability and the efflux of alkaloids of the Evodiae fructus in the Caco-2 model. Phytotherapy research : PTR. 2009 Jan; 23(1):56-60. doi: 10.1002/ptr.2555. [PMID: 18683848]
  • Han-Chieh Ko, Yea-Hwey Wang, Kuo-Tong Liou, Chi-Ming Chen, Chih-Hsiang Chen, Wen-Yen Wang, Shiou Chang, Yu-Chang Hou, Kuo-Tung Chen, Chieh-Fu Chen, Yuh-Chiang Shen. Anti-inflammatory effects and mechanisms of the ethanol extract of Evodia rutaecarpa and its bioactive components on neutrophils and microglial cells. European journal of pharmacology. 2007 Jan; 555(2-3):211-7. doi: 10.1016/j.ejphar.2006.10.002. [PMID: 17109845]
  • Han Chieh Ko, Kuo Tung Chen, Chieh Fu Chen, Jin Ping Su, Chi Ming Chen, Guei Jane Wang. Chemical and biological comparisons on Evodia with two related species of different locations and conditions. Journal of ethnopharmacology. 2006 Nov; 108(2):257-63. doi: 10.1016/j.jep.2006.05.020. [PMID: 16824714]
  • Daniel B Yarosh, Jason W Galvin, Stephanie L Nay, Arely V Peña, Matthew T Canning, David A Brown. Anti-inflammatory activity in skin by biomimetic of Evodia rutaecarpa extract from traditional Chinese medicine. Journal of dermatological science. 2006 Apr; 42(1):13-21. doi: 10.1016/j.jdermsci.2005.12.009. [PMID: 16423507]
  • Sung-Hoon Ahn, Seng-Ho Jeon, Takashi Tsuruo, Chang-Koo Shim, Suk-Jae Chung. Pharmacokinetic characterization of dehydroevodiamine in the rat brain. Journal of pharmaceutical sciences. 2004 Feb; 93(2):283-92. doi: 10.1002/jps.10546. [PMID: 14705186]
  • Yune-Fang Ueng, Han-Chieh Ko, Chieh-Fu Chen, Jong-Jing Wang, Kuo-Tung Chen. Modulation of drug-metabolizing enzymes by extracts of a herbal medicine Evodia rutaecarpa in C57BL/6J mice. Life sciences. 2002 Aug; 71(11):1267-77. doi: 10.1016/s0024-3205(02)01854-4. [PMID: 12106592]
  • Yune-Fang Ueng, Woan-Ching Jan, Lie-Chwen Lin, Ta-Liang Chen, F Peter Guengerich, Chieh-Fu Chen. The alkaloid rutaecarpine is a selective inhibitor of cytochrome P450 1A in mouse and human liver microsomes. Drug metabolism and disposition: the biological fate of chemicals. 2002 Mar; 30(3):349-53. doi: 10.1124/dmd.30.3.349. [PMID: 11854157]
  • W F Chiou, Y J Sung, J F Liao, A Y Shum, C F Chen. Inhibitory effect of dehydroevodiamine and evodiamine on nitric oxide production in cultured murine macrophages. Journal of natural products. 1997 Jul; 60(7):708-11. doi: 10.1021/np960495z. [PMID: 9249975]
  • C H Park, S H Kim, W Choi, Y J Lee, J S Kim, S S Kang, Y H Suh. Novel anticholinesterase and antiamnesic activities of dehydroevodiamine, a constituent of Evodia rutaecarpa. Planta medica. 1996 Oct; 62(5):405-9. doi: 10.1055/s-2006-957926. [PMID: 8923803]
  • W F Chiou, J F Liao, A Y Shum, C F Chen. Mechanisms of vasorelaxant effect of dehydroevodiamine: a bioactive isoquinazolinocarboline alkaloid of plant origin. Journal of cardiovascular pharmacology. 1996 Jun; 27(6):845-53. doi: 10.1097/00005344-199606000-00012. [PMID: 8761852]
  • W F Chiou, J F Liao, C F Chen. Comparative study of the vasodilatory effects of three quinazoline alkaloids isolated from Evodia rutaecarpa. Journal of natural products. 1996 Apr; 59(4):374-8. doi: 10.1021/np960161+. [PMID: 8699182]
  • T H Tsai, T F Lee, C F Chen, L C Wang. Thermoregulatory effects of alkaloids isolated from Wu-chu-yu in afebrile and febrile rats. Pharmacology, biochemistry, and behavior. 1995 Feb; 50(2):293-8. doi: 10.1016/0091-3057(94)00317-c. [PMID: 7740070]
  • Y T Peng, A Y Shum, T H Tasi, L C Lin, C F Chen. High-performance liquid chromatography of the quinazolinocarboline alkaloid dehydroevodiamine. Journal of chromatography. 1993 Jul; 617(1):87-93. doi: 10.1016/0378-4347(93)80425-4. [PMID: 8376542]
  • M C Yang, S L Wu, J S Kuo, C F Chen. The hypotensive and negative chronotropic effects of dehydroevodiamine. European journal of pharmacology. 1990 Jul; 182(3):537-42. doi: 10.1016/0014-2999(90)90052-8. [PMID: 2226622]
  • S B Xu, Y M Huang, C N Lau, C K Wat, Y C Kong. Hypotensive effect of dehydroevodiamine from Evodiae Fructus. The American journal of Chinese medicine. 1982; 10(1-4):75-85. doi: 10.1142/s0192415x82000130. [PMID: 7183211]
  • T NAKASATO, S ASADA, K MARUI. [Dehydroevodiamine, main alkaloid from the leaves of Evodia rutaecarpa Hooker fil. et Thomson]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1962 Apr; 82(?):619-26. doi: 10.1248/yakushi1947.82.4_619. [PMID: 14478214]