Evodiamine (BioDeep_00000000125)

 

Secondary id: BioDeep_00000178957, BioDeep_00000395782

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(1S)-21-METHYL-3,13,21-TRIAZAPENTACYCLO[11.8.0.0(2),(1)?.0?,?.0(1)?,(2)?]HENICOSA-2(10),4,6,8,15,17,19-HEPTAEN-14-ONE

化学式: C19H17N3O (303.1371552)
中文名称: (±)-吴茱萸碱, 吴茱萸碱, 吴茱萸胺
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 0.98%

分子结构信息

SMILES: CN1C2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3
InChI: InChI=1S/C19H17N3O/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/h2-9,18,20H,10-11H2,1H3

描述信息

Evodiamine is a member of beta-carbolines.
Evodiamine is a natural product found in Vepris soyauxii, Cryptocarya, and other organisms with data available.
Origin: Plant; Formula(Parent): C19H17N3O; Bottle Name:Evodiamine; PRIME Parent Name:Evodiamine; PRIME in-house No.:V0296; SubCategory_DNP: Monoterpenoid indole alkaloids, Indoloquinolizidine alkaloids, Indole alkaloids
Formula(Parent): C19H17N3O; Bottle Name:Evodiamine; Origin: Plant; PRIME Parent Name:Evodiamine; PRIME in-house No.:V0296; SubCategory_DNP: Monoterpenoid indole alkaloids, Indoloquinolizidine alkaloids, Indole alkaloids
Annotation level-1
(±)-Evodiamine, a quinazolinocarboline alkaloid, is a Top1 inhibitor. Evodiamine exhibits anti-inflammatory, antiobesity, and antitumor effects. (±)-Evodiamine inhibits the proliferation of a wide variety of tumor cells by inducing their apoptosis[1].
Evodiamine is an alkaloid isolated from the fruit of Evodia rutaecarpa Bentham with diverse biological activities including anti-inflammatory, anti-obesity, and antitumor.
Evodiamine is an alkaloid isolated from the fruit of Evodia rutaecarpa Bentham with diverse biological activities including anti-inflammatory, anti-obesity, and antitumor.

同义名列表

20 个代谢物同义名

(+/-)-Evodiamine; Evodiamine; (1S)-21-METHYL-3,13,21-TRIAZAPENTACYCLO[11.8.0.0(2),(1)?.0?,?.0(1)?,(2)?]HENICOSA-2(10),4,6,8,15,17,19-HEPTAEN-14-ONE; (1S)-21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one; INDOLO(2,3:3,4)PYRIDO(2,1-B)QUINAZOLIN-5(7H)-ONE, 8,13,13B,14-TETRAHYDRO-14-METHYL-, (13BS)-; Indol(2,3:3,4)pyrido(2,1-b)quinazolin-5(7H)-one, 8,13,13b,14-tetrahydro-14-methyl-, (13bS)-; Indol(2,3:3,4)pyrido(2,1-b)quinazolin-5(7H)-one, 8,13,13b,14-tetrahydro-14-methyl-, (S)-; (S)-14-methyl-7,8,13b,14-tetrahydroindolo[2,3:3,4]pyrido[2,1-b]quinazolin-5(13H)-one; (S)-14-methyl-8,13,13b,14-tetrahydroindolo[2,3:3,4]pyrido[2,1-b]quinazolin-5(7H)-one; Evodiamine, European Pharmacopoeia (EP) Reference Standard; evodiamine, (S)-isomer; EVODIAMINE [WHO-DD]; Evodiamine, (+)-; EVODIAMINE [MI]; (+)-Evodiamine; Evodiamine,(S); isoevodiamine; d-Evodiamine; C19H17N3O; (±)-Evodiamine



数据库引用编号

55 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)

16 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

  • Hao-Chun Hu, Szu-Yin Yu, Yi-Hong Tsai, Pei-Wen Hsieh, Hui-Chun Wang, Yan-Ning Chen, Ya-Ting Chuang, Min-Yu Lee, Hsueh-Wei Chang, Hao-Chun Hu, Yang-Chang Wu, Fang-Rong Chang, István Szatmári, Ferenc Fülöp. Synthesis of bioactive evodiamine and rutaecarpine analogues under ball milling conditions. Organic & biomolecular chemistry. 2024 03; 22(13):2620-2629. doi: 10.1039/d4ob00056k. [PMID: 38451121]
  • Xingxian Guo, Shiying Huang, Yonghong Zhang, Hong Wang, Lisha Li, Jianhua Ran, Dilong Chen, Xiaopeng Li, Jing Li. Evodiamine inhibits growth of vemurafenib drug-resistant melanoma via suppressing IRS4/PI3K/AKT signaling pathway. Journal of natural medicines. 2024 Mar; 78(2):342-354. doi: 10.1007/s11418-023-01769-9. [PMID: 38324123]
  • Jingbo Liu, Bingyan Guo, Siying Zhong, Yabing Shi, Zhengping Li, Zhenwu Yu, Zesheng Hao, Li Zhang, Fengyun Li, Yuanhong Wang, Yuxin Li. Novel Evodiamine-Based Sulfonamide Derivatives as Potent Insecticide Candidates Targeting Insect Ryanodine Receptors. Journal of agricultural and food chemistry. 2024 Jan; 72(2):1292-1301. doi: 10.1021/acs.jafc.3c05680. [PMID: 38178001]
  • Yunlong Tang, Weiying Gu, Lingling Cheng. Evodiamine attenuates oxidative stress and ferroptosis by inhibiting the MAPK signaling to improve bortezomib-induced peripheral neurotoxicity. Environmental toxicology. 2023 Nov; ?(?):. doi: 10.1002/tox.24035. [PMID: 38010754]
  • Ying Yu, Xing Huang, Chaoqi Liang, Peng Zhang. Evodiamine impairs HIF1A histone lactylation to inhibit Sema3A-mediated angiogenesis and PD-L1 by inducing ferroptosis in prostate cancer. European journal of pharmacology. 2023 Aug; 957(?):176007. doi: 10.1016/j.ejphar.2023.176007. [PMID: 37611839]
  • Yuan Cheng, XiaoPeng Huang, Yi Tang, Juan Li, Yimin Tan, Qianghua Yuan. Effects of evodiamine on ROS/TXNIP/NLRP3 pathway against gouty arthritis. Naunyn-Schmiedeberg's archives of pharmacology. 2023 Aug; ?(?):. doi: 10.1007/s00210-023-02654-8. [PMID: 37555854]
  • Ting Peng, Jinqiu Rao, Tingting Zhang, Yuan Wang, Na Li, Qing Gao, Xinchi Feng, Zhaohui Song, Kai Wang, Feng Qiu. Elucidation of the relationship between evodiamine-induced liver injury and CYP3A4-mediated metabolic activation by UPLC-MS/MS analysis. Analytical and bioanalytical chemistry. 2023 Jul; ?(?):. doi: 10.1007/s00216-023-04831-3. [PMID: 37433953]
  • Raghu Solanki, Ashok Kumar Jangid, Mahima Jadav, Hitesh Kulhari, Sunita Patel. Folate Functionalized and Evodiamine-Loaded Pluronic Nanomicelles for Augmented Cervical Cancer Cell Killing. Macromolecular bioscience. 2023 May; ?(?):e2300077. doi: 10.1002/mabi.202300077. [PMID: 37163974]
  • Yiwen Zha, Yongqi Yang, Yue Zhou, Bingqian Ye, Hongliang Li, Jingyan Liang. Dietary Evodiamine Inhibits Atherosclerosis-Associated Changes in Vascular Smooth Muscle Cells. International journal of molecular sciences. 2023 Apr; 24(7):. doi: 10.3390/ijms24076653. [PMID: 37047626]
  • Che-Yuan Hu, Hung-Tsung Wu, Yan-Shen Shan, Chung-Teng Wang, Gia-Shing Shieh, Chao-Liang Wu, Horng-Yih Ou. Evodiamine Exhibits Anti-Bladder Cancer Activity by Suppression of Glutathione Peroxidase 4 and Induction of Ferroptosis. International journal of molecular sciences. 2023 Mar; 24(7):. doi: 10.3390/ijms24076021. [PMID: 37046995]
  • Li Zhang, Lihui Li, Xihui Chen, Shuying Yuan, Tong Xu, Weili Zhao, Meng Li, Fengying Wang, Robert M Hoffman, Lijun Jia. Evodiamine inhibits ESCC by inducing M-phase cell-cycle arrest via CUL4A/p53/p21 axis and activating noxa-dependent intrinsic and DR4-dependent extrinsic apoptosis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Jan; 108(?):154493. doi: 10.1016/j.phymed.2022.154493. [PMID: 36265256]
  • Fazile Nur Ekinci Akdemir, Serkan Yıldırım, Fatih Mehmet Kandemir. The possible beneficial impacts of evodiamine on hepatotoxicity induced by cisplatin. Environmental science and pollution research international. 2022 Dec; 29(59):89522-89529. doi: 10.1007/s11356-022-22007-x. [PMID: 35854071]
  • Ruifeng Liang, Wenjing Ge, Bingjie Li, Weifeng Cui, Xiaofan Ma, Yuying Pan, Gengsheng Li. Evodiamine decreased the systemic exposure of pravastatin in non-alcoholic steatohepatitis rats due to the up-regulation of hepatic OATPs. Pharmaceutical biology. 2022 Dec; 60(1):359-373. doi: 10.1080/13880209.2022.2036767. [PMID: 35171063]
  • Yan Liang, Honghua Zhang, Xi Zhang, Ying Peng, Jiedan Deng, Yuqing Wang, Ranhui Li, Linyi Liu, Zhen Wang. Discovery of evodiamine derivatives as potential lead antifungal agents for the treatment of superficial fungal infections. Bioorganic chemistry. 2022 10; 127(?):105981. doi: 10.1016/j.bioorg.2022.105981. [PMID: 35785554]
  • Jingli Liu, Hui Guo, Jing Zhou, Yuwei Wang, Hao Yan, Ruyi Jin, Yuping Tang. Evodiamine and Rutaecarpine as Potential Anticancer Compounds: A Combined Computational Study. International journal of molecular sciences. 2022 Sep; 23(19):. doi: 10.3390/ijms231911513. [PMID: 36232809]
  • Munmun Panda, Surya Kant Tripathi, Gokhan Zengin, Bijesh K Biswal. Evodiamine as an anticancer agent: a comprehensive review on its therapeutic application, pharmacokinetic, toxicity, and metabolism in various cancers. Cell biology and toxicology. 2022 Sep; ?(?):. doi: 10.1007/s10565-022-09772-8. [PMID: 36138312]
  • Min Xu, Wenhua Wang, Wei Lu, Xiaoyang Ling, Qin Rui, Haibo Ni. Evodiamine prevents traumatic brain injury through inhibiting oxidative stress via PGK1/NRF2 pathway. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Sep; 153(?):113435. doi: 10.1016/j.biopha.2022.113435. [PMID: 36076551]
  • Yuejie Yu, Qinyan Lu, Feng Chen, Shangli Wang, Chunxiang Niu, Jiabao Liao, Hongwu Wang, Fengjuan Chen. Serum untargeted metabolomics analysis of the mechanisms of evodiamine on type 2 diabetes mellitus model rats. Food & function. 2022 Jun; 13(12):6623-6635. doi: 10.1039/d1fo04396j. [PMID: 35635367]
  • Jingbo Liu, Yabing Shi, Shuting Chen, Fengyun Li, Wen Wen, Yuanhong Wang. Discovery of evodiamine derivatives as potent insecticide candidates. Bioorganic & medicinal chemistry. 2022 05; 62(?):116727. doi: 10.1016/j.bmc.2022.116727. [PMID: 35366437]
  • Yongfeng Zhang, Yaqin Zhang, Yang Zhao, Wanyue Wu, Weiqi Meng, Yulin Zhou, Ye Qiu, Chenliang Li. Protection against ulcerative colitis and colorectal cancer by evodiamine via anti‑inflammatory effects. Molecular medicine reports. 2022 05; 25(5):. doi: 10.3892/mmr.2022.12704. [PMID: 35362542]
  • Jingbo Liu, Yabing Shi, Zhicheng Tian, Fengyun Li, Zesheng Hao, Wen Wen, Li Zhang, Yuanhong Wang, Yuxin Li, Zhijin Fan. Bioactivity-Guided Synthesis Accelerates the Discovery of Evodiamine Derivatives as Potent Insecticide Candidates. Journal of agricultural and food chemistry. 2022 Apr; 70(16):5197-5206. doi: 10.1021/acs.jafc.1c08297. [PMID: 35435667]
  • Weihang Guo, Xianheng Wang, Jidong Zhang, Tingting Zhang, Hongfeng Lv, Changkuo Zhao. Synthesis of ring opening of evodiamine derivatives and evaluation on their biological activity. Chemical biology & drug design. 2022 04; 99(4):535-546. doi: 10.1111/cbdd.13996. [PMID: 34923753]
  • Ziyi Liang, Fang Lei, Jiedan Deng, Honghua Zhang, Yuqing Wang, Junfang Li, Tao Shi, Xiaoyan Yang, Zhen Wang. Design, synthesis and bioactivity evaluation of novel evodiamine derivatives with excellent potency against gastric cancer. European journal of medicinal chemistry. 2022 Jan; 228(?):113960. doi: 10.1016/j.ejmech.2021.113960. [PMID: 34774339]
  • Cheng-Jie Yang, Hai-Xin Li, Jing-Ru Wang, Zhi-Jun Zhang, Tian-Lin Wu, Ying-Qian Liu, Chen Tang, Qing-Ru Chu, Sha-Sha Du, Ying-Hui He. Design, synthesis and biological evaluation of novel evodiamine and rutaecarpine derivatives against phytopathogenic fungi. European journal of medicinal chemistry. 2022 Jan; 227(?):113937. doi: 10.1016/j.ejmech.2021.113937. [PMID: 34710744]
  • Meixia Fan, Lei Yao. The Synthesis, Structural Modification and Mode of Anticancer Action of Evodiamine: A Review. Recent patents on anti-cancer drug discovery. 2022; 17(3):284-296. doi: 10.2174/1574892817666211221165739. [PMID: 34939550]
  • Yuting Li, Yuming Wang, Xiaoqun Wang, Lulu Jin, Lu Yang, Jinli Zhu, Hongwu Wang, Fang Zheng, Huantian Cui, Xiaojiang Li, Yingjie Jia. Evodiamine suppresses the progression of non-small cell lung carcinoma via endoplasmic reticulum stress-mediated apoptosis pathway in vivo and in vitro. International journal of immunopathology and pharmacology. 2022 Jan; 36(?):3946320221086079. doi: 10.1177/03946320221086079. [PMID: 35388733]
  • Yufan Dai, Wenyu Zhu, Jiaxuan Zhou, Tao Shen. The combination of berberine and evodiamine ameliorates high-fat diet-induced non-alcoholic fatty liver disease associated with modulation of gut microbiota in rats. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 2022; 55(?):e12096. doi: 10.1590/1414-431x2022e12096. [PMID: 35584453]
  • Yuhe Lei, Meiching Chan, Haiyan Liu, Wenyu Lyu, Lei Chen, Yinqin Zhong, Hua Gan, Mei Wang, Ming Qi, Yu Guo, Junshan Liu, Enxin Zhang. Evodiamine as the Active Compound of Evodiae fructus to Inhibit Proliferation and Migration of Prostate Cancer through PI3K/AKT/NF-κB Signaling Pathway. Disease markers. 2022; 2022(?):4399334. doi: 10.1155/2022/4399334. [PMID: 35899176]
  • Xingming Hou, Clemens Malainer, Atanas G Atanasov, Elke H Heiß, Verena M Dirsch, Limei Wang, KeWei Wang. Evodiamine Lowers Blood Lipids by Up-Regulating the PPARγ/ABCG1 Pathway in High-Fat-Diet-Fed Mice. Journal of natural products. 2021 12; 84(12):3110-3116. doi: 10.1021/acs.jnatprod.1c00881. [PMID: 34902249]
  • Y D Gao, A Zhu, L D Li, T Zhang, S Wang, D P Shan, Y Z Li, Q Wang. [Cytotoxicity and underlying mechanism of evodiamine in HepG2 cells]. Beijing da xue xue bao. Yi xue ban = Journal of Peking University. Health sciences. 2021 Dec; 53(6):1107-1114. doi: . [PMID: 34916690]
  • Qiong Wang, Yubao Cui, Xufeng Wu, Junfang Wang. Evodiamine protects against airway remodelling and inflammation in asthmatic rats by modulating the HMGB1/NF-κB/TLR-4 signalling pathway. Pharmaceutical biology. 2021 Dec; 59(1):192-199. doi: 10.1080/13880209.2020.1871374. [PMID: 33577738]
  • Zhijun Zhao, Yurun Xue, Gaohua Zhang, Jie Jia, Ruilian Xiu, Yugai Jia, Yuanyuan Wang, Xiangchong Wang, Honglin Li, Pingping Chen, Xuan Zhang. Identification of evodiamine and rutecarpine as novel TMEM16A inhibitors and their inhibitory effects on peristalsis in isolated Guinea-pig ileum. European journal of pharmacology. 2021 Oct; 908(?):174340. doi: 10.1016/j.ejphar.2021.174340. [PMID: 34265294]
  • Chun-Qi Yang, Wen-Yu Lian, Yu-Guang Wang, Yue Gao. [Research progress in pharmacology and toxicology of evodiamine]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2021 Oct; 46(20):5218-5225. doi: 10.19540/j.cnki.cjcmm.20210518.602. [PMID: 34738422]
  • Xiaqing Liu, Xiaofang Peng, Zhengfang Lin. Evodiamine Enhanced the Anti-Inflammation Effect of Clindamycin in the BEAS-2B Cells Infected with H5N1 and Pneumoniae D39 Through CREB-C/EBPβ Signaling Pathway. Viral immunology. 2021 Jul; 34(6):410-415. doi: 10.1089/vim.2020.0319. [PMID: 33945347]
  • J Miao, H T Cui, L Wang, L Y Guo, J Wang, P Li, J Y Lei, J W Jia. [Effects of evodiamine on carbon tetrachloride-induced liver fibrosis mice based on modulating gut microbiota]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2021 Jun; 39(6):401-406. doi: 10.3760/cma.j.cn121094-20201204-00666. [PMID: 34218553]
  • Dong Xu, Chao Qiu, Yue Wang, Tao Qiao, Yuan-Lu Cui. Intranasal co-delivery of berberine and evodiamine by self-assembled thermosensitive in-situ hydrogels for improving depressive disorder. International journal of pharmaceutics. 2021 Jun; 603(?):120667. doi: 10.1016/j.ijpharm.2021.120667. [PMID: 33933642]
  • Cui Ye, Nan Zhang, Qian Zhao, Xin Xie, Xiang Li, Hong-Ping Zhu, Cheng Peng, Wei Huang, Bo Han. Evodiamine alleviates lipopolysaccharide-induced pulmonary inflammation and fibrosis by activating apelin pathway. Phytotherapy research : PTR. 2021 Jun; 35(6):3406-3417. doi: 10.1002/ptr.7062. [PMID: 33657655]
  • Li-Qing Zhu, Li Zhang, Jia Zhang, Guo-Lin Chang, Gang Liu, Dan-Dan Yu, Xiao-Min Yu, Mi-Sheng Zhao, Bin Ye. Evodiamine inhibits high-fat diet-induced colitis-associated cancer in mice through regulating the gut microbiota. Journal of integrative medicine. 2021 Jan; 19(1):56-65. doi: 10.1016/j.joim.2020.11.001. [PMID: 33277208]
  • Ze-Bo Jiang, Ju-Min Huang, Ya-Jia Xie, Yi- Zhong Zhang, Chan Chang, Huan-Ling Lai, Wenjun Wang, Xiao-Jun Yao, Xing-Xing Fan, Qi-Biao Wu, Chun Xie, Mei-Fang Wang, Elaine Lai-Han Leung. Evodiamine suppresses non-small cell lung cancer by elevating CD8+ T cells and downregulating the MUC1-C/PD-L1 axis. Journal of experimental & clinical cancer research : CR. 2020 Nov; 39(1):249. doi: 10.1186/s13046-020-01741-5. [PMID: 33208183]
  • Qiang Sun, Long Xie, Jiawen Song, Xiaofang Li. Evodiamine: A review of its pharmacology, toxicity, pharmacokinetics and preparation researches. Journal of ethnopharmacology. 2020 Nov; 262(?):113164. doi: 10.1016/j.jep.2020.113164. [PMID: 32738391]
  • Xuechun Chen, Dejin Xun, Ruzhang Zheng, Lu Zhao, Yuqing Lu, Jun Huang, Rui Wang, Yi Wang. Deep-Learning-Assisted Assessment of DNA Damage Based on Foci Images and Its Application in High-Content Screening of Lead Compounds. Analytical chemistry. 2020 10; 92(20):14267-14277. doi: 10.1021/acs.analchem.0c03741. [PMID: 32986405]
  • Chao Huang, Ke Ming Xiang, Bing Jun Liang, Wei Xuan Huang, Fan Jun Zhang, Yu Wan Shao, Xiu Lian Wang, Hao Sheng Liu, Wei Zeng Shen. Combination of Evodiamine with Berberine Reveals a Regulatory Effect on the Phenotypic Transition of Colon Epithelial Cells Induced by CCD-18Co. Chinese medical sciences journal = Chung-kuo i hsueh k'o hsueh tsa chih. 2020 Sep; 35(3):195-206. doi: 10.24920/003670. [PMID: 32972497]
  • Meng-Xia Wang, Li Lin, Yong-Da Chen, Yu-Ping Zhong, Yi-Xuan Lin, Pei Li, Xing Tian, Bo Han, Zhi-Yong Xie, Qiong-Feng Liao. Evodiamine has therapeutic efficacy in ulcerative colitis by increasing Lactobacillus acidophilus levels and acetate production. Pharmacological research. 2020 09; 159(?):104978. doi: 10.1016/j.phrs.2020.104978. [PMID: 32485282]
  • Shuang Zhao, Ke Xu, Rong Jiang, Dan-Yang Li, Xing-Xian Guo, Peng Zhou, Jia-Feng Tang, Li-Sha Li, Di Zeng, Ling Hu, Jian-Hua Ran, Jing Li, Di-Long Chen. Evodiamine inhibits proliferation and promotes apoptosis of hepatocellular carcinoma cells via the Hippo-Yes-Associated Protein signaling pathway. Life sciences. 2020 Jun; 251(?):117424. doi: 10.1016/j.lfs.2020.117424. [PMID: 32057900]
  • Jiacheng Lin, Xu Zhang, Chaotong Li, Yingyan Zhang, Hanzhi Lu, Jiwei Chen, Zeyu Li, Xuejun Yang, Zhongping Wu. Evodiamine via targeting nNOS and AMPA receptor GluA1 inhibits nitroglycerin-induced migraine-like response. Journal of ethnopharmacology. 2020 May; 254(?):112727. doi: 10.1016/j.jep.2020.112727. [PMID: 32147481]
  • Xiaoyong Guan, Xiaoting Zheng, Chi Teng Vong, Jinyao Zhao, Jianbo Xiao, Yitao Wang, Zhangfeng Zhong. Combined effects of berberine and evodiamine on colorectal cancer cells and cardiomyocytes in vitro. European journal of pharmacology. 2020 May; 875(?):173031. doi: 10.1016/j.ejphar.2020.173031. [PMID: 32109457]
  • Hongmei Lin, Longfei Lin, Yoonsun Choi, Bozena Michniak-Kohn. Development and in-vitro evaluation of co-loaded berberine chloride and evodiamine ethosomes for treatment of melanoma. International journal of pharmaceutics. 2020 May; 581(?):119278. doi: 10.1016/j.ijpharm.2020.119278. [PMID: 32229284]
  • Xiaojiaoyang Li, Junde Ge, Qi Zheng, Jiaxiang Zhang, Rong Sun, Runping Liu. Evodiamine and rutaecarpine from Tetradium ruticarpum in the treatment of liver diseases. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Mar; 68(?):153180. doi: 10.1016/j.phymed.2020.153180. [PMID: 32092638]
  • Fu-Shu Li, Jun Huang, Mao-Zhi Cui, Jin-Ru Zeng, Pei-Pei Li, Ling Li, Yan Deng, Ying Hu, Bai-Cheng He, De-Zhong Shu. BMP9 mediates the anticancer activity of evodiamine through HIF‑1α/p53 in human colon cancer cells. Oncology reports. 2020 02; 43(2):415-426. doi: 10.3892/or.2019.7427. [PMID: 31894286]
  • Lei Wang, Kun Fang, Junfei Cheng, Yu Li, Yahui Huang, Shuqiang Chen, Guoqiang Dong, Shanchao Wu, Chunquan Sheng. Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer. Journal of medicinal chemistry. 2020 01; 63(2):696-713. doi: 10.1021/acs.jmedchem.9b01626. [PMID: 31880942]
  • Li-Fei Nie, Si-Si Wang, Jian-Guo Cao, Fei-Ze Liu, Hainimu Xiamuxi, Haji Akber Aisa, Guo-Zheng Huang. Straightforward synthesis, characterization, and cytotoxicity evaluation of hybrids of natural alkaloid evodiamine/rutaecarpine and thieno[2,3-d]pyrimidinones. Journal of Asian natural products research. 2020 Jan; 22(1):69-82. doi: 10.1080/10286020.2018.1540599. [PMID: 30588834]
  • Yan Wang, Weiping Yang, Fang Peng, Tianqi Chen, Yunyan Fu, Min Tian. [Evodiamine inhibits injury of HUVECs induced by lipopolysaccharide through TLR4/NF-κB signaling pathway]. Xi bao yu fen zi mian yi xue za zhi = Chinese journal of cellular and molecular immunology. 2019 Dec; 35(12):1088-1093. doi: . [PMID: 31894007]
  • Baofang Zhang, Zilin Chen. Screening of cathepsin B inhibitors in traditional Chinese medicine by capillary electrophoresis with immobilized enzyme microreactor. Journal of pharmaceutical and biomedical analysis. 2019 Nov; 176(?):112811. doi: 10.1016/j.jpba.2019.112811. [PMID: 31437748]
  • Ersen Eraslan, Ayhan Tanyeli, Elif Polat, Zeliha Yetim. Evodiamine alleviates kidney ischemia reperfusion injury in rats: A biochemical and histopathological study. Journal of cellular biochemistry. 2019 10; 120(10):17159-17166. doi: 10.1002/jcb.28976. [PMID: 31099131]
  • Wanbin Yang, Xiuli Gong, Xiulian Wang, Chao Huang. A mediator of phosphorylated Smad2/3, evodiamine, in the reversion of TAF-induced EMT in normal colonic epithelial cells. Investigational new drugs. 2019 10; 37(5):865-875. doi: 10.1007/s10637-018-0702-x. [PMID: 30488243]
  • Yikun Liu, Wei Zhou, Zhenkun Mao, Zilin Chen. Analysis of Evodiae Fructus by capillary electrochromatography-mass spectrometry with methyl-vinylimidazole functionalized organic polymer monolilth as stationary phases. Journal of chromatography. A. 2019 Sep; 1602(?):474-480. doi: 10.1016/j.chroma.2019.06.011. [PMID: 31202495]
  • Chunpu Li, Gang Cai, Daqian Song, Ruixuan Gao, Peng Teng, LiHong Zhou, Qing Ji, Hua Sui, Jianfeng Cai, Qi Li, Yan Wang. Development of EGFR-targeted evodiamine nanoparticles for the treatment of colorectal cancer. Biomaterials science. 2019 Aug; 7(9):3627-3639. doi: 10.1039/c9bm00613c. [PMID: 31328737]
  • Biqiang Zhu, Lei Zhao, Yang Liu, Ye Jin, Jing Feng, Fuya Zhao, Jiayu Sun, Rui Geng, Yunwei Wei. Induction of phosphatase shatterproof 2 by evodiamine suppresses the proliferation and invasion of human cholangiocarcinoma. The international journal of biochemistry & cell biology. 2019 03; 108(?):98-110. doi: 10.1016/j.biocel.2019.01.012. [PMID: 30682488]
  • 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]
  • Peng Shen, Zecai Zhang, Kunpeng Zhu, Hongyang Cao, Jiuxi Liu, Xiaojie Lu, Yanxin Li, Yue Jing, Xin Yuan, Yunhe Fu, Yongguo Cao, Naisheng Zhang. Evodiamine prevents dextran sulfate sodium-induced murine experimental colitis via the regulation of NF-κB and NLRP3 inflammasome. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2019 Feb; 110(?):786-795. doi: 10.1016/j.biopha.2018.12.033. [PMID: 30554117]
  • Yi Feng, Ning-Xi Li, Huan-Li Yin, Tian-Yu Chen, Qian Yang, Min Wu. Thermo- and pH-responsive, Lipid-coated, Mesoporous Silica Nanoparticle-based Dual Drug Delivery System To Improve the Antitumor Effect of Hydrophobic Drugs. Molecular pharmaceutics. 2019 01; 16(1):422-436. doi: 10.1021/acs.molpharmaceut.8b01073. [PMID: 30525641]
  • Yong-Tai Zhang, Zhi Wang, Li-Na Shen, Yan-Yan Li, Ze-Hui He, Qing Xia, Nian-Ping Feng. A novel microemulsion-based isotonic perfusate modulated by Ringer's solution for improved microdialysis recovery of liposoluble substances. Journal of nanobiotechnology. 2018 Nov; 16(1):91. doi: 10.1186/s12951-018-0418-2. [PMID: 30428875]
  • Jing Zhao, Shan Liu, Xueyuan Hu, Yunmei Zhang, Shenglei Yan, Hua Zhao, Mei Zeng, Yao Li, Lan Yang, Jingqing Zhang. Improved delivery of natural alkaloids into lung cancer through woody oil-based emulsive nanosystems. Drug delivery. 2018 Nov; 25(1):1426-1437. doi: 10.1080/10717544.2018.1474970. [PMID: 29890855]
  • Xu Hu, Dahong Li, Chun Chu, Xu Li, Xianhua Wang, Ying Jia, Huiming Hua, Fanxing Xu. Antiproliferative Effects of Alkaloid Evodiamine and Its Derivatives. International journal of molecular sciences. 2018 Oct; 19(11):. doi: 10.3390/ijms19113403. [PMID: 30380774]
  • H X Ren, Q C Tang, L Yan, H Xia, H S Luo. Evodiamine inhibits gastrointestinal motility via CCK and CCK1 receptor in water-avoidence stress rat model. Life sciences. 2018 Sep; 209(?):210-216. doi: 10.1016/j.lfs.2018.08.003. [PMID: 30086275]
  • Yuelai Zhou, Jinlong Hu. Evodiamine Induces Apoptosis, G2/M Cell Cycle Arrest, and Inhibition of Cell Migration and Invasion in Human Osteosarcoma Cells via Raf/MEK/ERK Signalling Pathway. Medical science monitor : international medical journal of experimental and clinical research. 2018 08; 24(?):5874-5880. doi: 10.12659/msm.909682. [PMID: 30135419]
  • Limei Wang, Pierre Eftekhari, Daniel Schachner, Irena D Ignatova, Veronika Palme, Nicole Schilcher, Angela Ladurner, Elke H Heiss, Herbert Stangl, Verena M Dirsch, Atanas G Atanasov. Novel interactomics approach identifies ABCA1 as direct target of evodiamine, which increases macrophage cholesterol efflux. Scientific reports. 2018 07; 8(1):11061. doi: 10.1038/s41598-018-29281-1. [PMID: 30038271]
  • 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]
  • Cuiyun Wang, Fang Yue, Guangfeng Ai, Jie Yang. Simultaneous determination of evodiamine and its four metabolites in rat plasma by LC-MS/MS and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2018 Jul; 32(7):e4219. doi: 10.1002/bmc.4219. [PMID: 29470848]
  • Yongfeng Zhang, Jiaqi Wang, Chunyue Wang, Zhiping Li, Xin Liu, Jun Zhang, Jiahui Lu, Di Wang. Pharmacological Basis for the Use of Evodiamine in Alzheimer's Disease: Antioxidation and Antiapoptosis. International journal of molecular sciences. 2018 May; 19(5):. doi: 10.3390/ijms19051527. [PMID: 29883380]
  • Yun Xue, Ting Guo, Lifang Zou, Yingxin Gong, Bing Wu, Zhihua Yi, Tianyu Jia, Shanhong Zhao, Liran Shi, Lin Li, Huilong Yuan, Hui Liu, Yun Gao, Guilin Li, Shuangmei Liu, Hong Xu, Chunping Zhang, Shangdong Liang, Guodong Li. Evodiamine Attenuates P2X7-Mediated Inflammatory Injury of Human Umbilical Vein Endothelial Cells Exposed to High Free Fatty Acids. Oxidative medicine and cellular longevity. 2018; 2018(?):5082817. doi: 10.1155/2018/5082817. [PMID: 30210654]
  • Xin Zhou, Fengying Ren, Hong Wei, Liyun Liu, Tao Shen, Shijun Xu, Jiangping Wei, Jiayue Ren, Hengfan Ni. Combination of berberine and evodiamine inhibits intestinal cholesterol absorption in high fat diet induced hyperlipidemic rats. Lipids in health and disease. 2017 Dec; 16(1):239. doi: 10.1186/s12944-017-0628-x. [PMID: 29228954]
  • Jia Du, Yang Sun, Yi-Yu Lu, Eric Lau, Ming Zhao, Qian-Mei Zhou, Shi-Bing Su. Berberine and Evodiamine Act Synergistically Against Human Breast Cancer MCF-7 Cells by Inducing Cell Cycle Arrest and Apoptosis. Anticancer research. 2017 11; 37(11):6141-6151. doi: 10.21873/anticanres.12063. [PMID: 29061795]
  • Yong-Tai Zhang, Zhe Li, Kai Zhang, Hong-Yu Zhang, Ze-Hui He, Qing Xia, Ji-Hui Zhao, Nian-Ping Feng. Co-delivery of evodiamine and rutaecarpine in a microemulsion-based hyaluronic acid hydrogel for enhanced analgesic effects on mouse pain models. International journal of pharmaceutics. 2017 Aug; 528(1-2):100-106. doi: 10.1016/j.ijpharm.2017.05.064. [PMID: 28571904]
  • Che-Yuan Hu, Hung-Tsung Wu, Yu-Chu Su, Ching-Han Lin, Chih-Jen Chang, Chao-Liang Wu. Evodiamine Exerts an Anti-Hepatocellular Carcinoma Activity through a WWOX-Dependent Pathway. Molecules (Basel, Switzerland). 2017 Jul; 22(7):. doi: 10.3390/molecules22071175. [PMID: 28708106]
  • Weifeng Yang, Lina Ma, Sidi Li, Kaiyu Cui, Lei Lei, Zuguang Ye. Evaluation of the Cardiotoxicity of Evodiamine In Vitro and In Vivo. Molecules (Basel, Switzerland). 2017 Jun; 22(6):. doi: 10.3390/molecules22060943. [PMID: 28598372]
  • Xiao-Han Jiang, Qing-Qing Wu, Yang Xiao, Yuan Yuan, Zheng Yang, Zhou-Yan Bian, Wei Chang, Qi-Zhu Tang. Evodiamine Prevents Isoproterenol-Induced Cardiac Fibrosis by Regulating Endothelial-to-Mesenchymal Transition. Planta medica. 2017 Jun; 83(9):761-769. doi: 10.1055/s-0042-124044. [PMID: 28010025]
  • Xia Fan, Jun-Yu Zhu, Yu Sun, Li Luo, Jun Yan, Xue Yang, Jing Yu, Wan-Qi Tang, Wei Ma, Hua-Ping Liang. Evodiamine Inhibits Zymosan-Induced Inflammation In Vitro and In Vivo: Inactivation of NF-κB by Inhibiting IκBα Phosphorylation. Inflammation. 2017 Jun; 40(3):1012-1027. doi: 10.1007/s10753-017-0546-0. [PMID: 28337636]
  • Chao Huang, Hong Liu, Xiu-Li Gong, Li-Yun Wu, Bin Wen. Effect of evodiamine and berberine on the interaction between DNMTs and target microRNAs during malignant transformation of the colon by TGF-β1. Oncology reports. 2017 Mar; 37(3):1637-1645. doi: 10.3892/or.2017.5379. [PMID: 28098901]
  • Chung-Sheng Shi, Jhy-Ming Li, Chih-Chien Chin, Yi-Hung Kuo, Ying-Ray Lee, Yun-Ching Huang. Evodiamine Induces Cell Growth Arrest, Apoptosis and Suppresses Tumorigenesis in Human Urothelial Cell Carcinoma Cells. Anticancer research. 2017 03; 37(3):1149-1159. doi: 10.21873/anticanres.11428. [PMID: 28314276]
  • Shun-Ting Chou, Chien-Yun Hsiang, Hsin-Yi Lo, Hui-Fen Huang, Ming-Tsung Lai, Ching-Liang Hsieh, Su-Yin Chiang, Tin-Yun Ho. Exploration of anti-cancer effects and mechanisms of Zuo-Jin-Wan and its alkaloid components in vitro and in orthotopic HepG2 xenograft immunocompetent mice. BMC complementary and alternative medicine. 2017 Feb; 17(1):121. doi: 10.1186/s12906-017-1586-6. [PMID: 28219365]
  • Wen-Shin Wu, Chih-Chiang Chien, Kao-Hui Liu, Yen-Chou Chen, Wen-Ta Chiu. Evodiamine Prevents Glioma Growth, Induces Glioblastoma Cell Apoptosis and Cell Cycle Arrest through JNK Activation. The American journal of Chinese medicine. 2017; 45(4):879-899. doi: 10.1142/s0192415x17500471. [PMID: 28514905]
  • Xie Ge, Si-Yu Chen, Mei Liu, Ting-Ming Liang, Chang Liu. Evodiamine inhibits PDGF‑BB‑induced proliferation of rat vascular smooth muscle cells through the suppression of cell cycle progression and oxidative stress. Molecular medicine reports. 2016 Nov; 14(5):4551-4558. doi: 10.3892/mmr.2016.5798. [PMID: 27748810]
  • Vijay Mohan, Rajesh Agarwal, Rana P Singh. A novel alkaloid, evodiamine causes nuclear localization of cytochrome-c and induces apoptosis independent of p53 in human lung cancer cells. Biochemical and biophysical research communications. 2016 09; 477(4):1065-1071. doi: 10.1016/j.bbrc.2016.07.037. [PMID: 27402273]
  • Li Lin, Li Ren, Liujing Wen, Yu Wang, Jin Qi. Effect of evodiamine on the proliferation and apoptosis of A549 human lung cancer cells. Molecular medicine reports. 2016 Sep; 14(3):2832-8. doi: 10.3892/mmr.2016.5575. [PMID: 27485202]
  • Le Shi, Fan Yang, Fei Luo, Yi Liu, Feng Zhang, Meijuan Zou, Qizhan Liu. Evodiamine exerts anti-tumor effects against hepatocellular carcinoma through inhibiting β-catenin-mediated angiogenesis. Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine. 2016 Sep; 37(9):12791-12803. doi: 10.1007/s13277-016-5251-3. [PMID: 27449032]
  • Hui Guo, Dongmei Liu, Bin Gao, Xiaohui Zhang, Minli You, Hui Ren, Hongbo Zhang, Hélder A Santos, Feng Xu. Antiproliferative Activity and Cellular Uptake of Evodiamine and Rutaecarpine Based on 3D Tumor Models. Molecules (Basel, Switzerland). 2016 Jul; 21(7):. doi: 10.3390/molecules21070954. [PMID: 27455219]
  • Hui Feng, Baorui Guo, Xiangmei Kong, Biao Wu. [Evodiamine enhances the radiosensitivity of esophageal squamous cell cancer Eca-109 cells]. Xi bao yu fen zi mian yi xue za zhi = Chinese journal of cellular and molecular immunology. 2016 Jul; 32(7):940-4. doi: ". [PMID: 27363277]
  • Hua Sui, Li-Hong Zhou, Ya-Li Zhang, Jian-Ping Huang, Xuan Liu, Qing Ji, Xiao-Ling Fu, Hao-Tian Wen, Zhe-Sheng Chen, Wan-Li Deng, Hui-Rong Zhu, Qi Li. Evodiamine Suppresses ABCG2 Mediated Drug Resistance by Inhibiting p50/p65 NF-κB Pathway in Colorectal Cancer. Journal of cellular biochemistry. 2016 Jun; 117(6):1471-81. doi: 10.1002/jcb.25451. [PMID: 26590365]
  • Lijuan Wei, Xiaoying Jin, Zipei Cao, Wenlu Li. [Evodiamine induces extrinsic and intrinsic apoptosis of ovarian cancer cells via the mitogen-activated protein kinase/phosphatidylinositol-3-kinase/protein kinase B signaling pathways]. Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan. 2016 Jun; 36(3):353-9. doi: 10.1016/s0254-6272(16)30049-8. [PMID: 27468551]
  • Shenglan Wang, Satoshi Yamamoto, Yoko Kogure, Wensheng Zhang, Koichi Noguchi, Yi Dai. Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa. Journal of natural products. 2016 05; 79(5):1225-30. doi: 10.1021/acs.jnatprod.5b00599. [PMID: 27159637]
  • Xue Zhang, Hong-Ming Liu, Ting-Ting Lei, Jiao Feng, Jing-Qing Zhang. [A preliminary study of pharmacokinetics of evodiamine hydroxypropyl-β-cyclodextrin inclusion complex]. Nan fang yi ke da xue xue bao = Journal of Southern Medical University. 2016 Apr; 36(4):548-51. doi: NULL. [PMID: 27113185]
  • Yanchuan Wu, Xueqiang Pan, Yongsong Xu, Xuran Lu, Shida He, Rui He, Muxin Gong. Optimization of combinations of ginsenoside-Rg1, ginsenoside-Rb1, evodiamine and rutaecarpine for effective therapy of mouse migraine. Journal of natural medicines. 2016 Apr; 70(2):207-16. doi: 10.1007/s11418-015-0960-2. [PMID: 26711833]
  • Seula Han, Jong Kyu Woo, Yuchae Jung, Dawoon Jeong, Minsook Kang, Young-Ji Yoo, Hani Lee, Seung Hyun Oh, Jae-Ha Ryu, Woo-Young Kim. Evodiamine selectively targets cancer stem-like cells through the p53-p21-Rb pathway. Biochemical and biophysical research communications. 2016 Jan; 469(4):1153-8. doi: 10.1016/j.bbrc.2015.12.066. [PMID: 26713361]
  • Zhi-Yong Wang, Jian-Gang Liu, Hao Li, Hui-Ming Yang. Pharmacological Effects of Active Components of Chinese Herbal Medicine in the Treatment of Alzheimer's Disease: A Review. The American journal of Chinese medicine. 2016; 44(8):1525-1541. doi: 10.1142/s0192415x16500853. [PMID: 27848250]
  • Wen-Shin Wu, Chih-Chiang Chien, Yen-Chou Chen, Wen-Ta Chiu. Protein Kinase RNA-Like Endoplasmic Reticulum Kinase-Mediated Bcl-2 Protein Phosphorylation Contributes to Evodiamine-Induced Apoptosis of Human Renal Cell Carcinoma Cells. PloS one. 2016; 11(8):e0160484. doi: 10.1371/journal.pone.0160484. [PMID: 27483435]
  • Lidi Zou, Fengqian Chen, Jiaolin Bao, Shengpeng Wang, Lu Wang, Meiwan Chen, Chengwei He, Yitao Wang. Preparation, characterization, and anticancer efficacy of evodiamine-loaded PLGA nanoparticles. Drug delivery. 2016; 23(3):908-16. doi: 10.3109/10717544.2014.920936. [PMID: 24904975]
  • Emiko Iwaoka, Shenglan Wang, Nobuyuki Matsuyoshi, Yoko Kogure, Shunji Aoki, Satoshi Yamamoto, Koichi Noguchi, Yi Dai. Evodiamine suppresses capsaicin-induced thermal hyperalgesia through activation and subsequent desensitization of the transient receptor potential V1 channels. Journal of natural medicines. 2016 Jan; 70(1):1-7. doi: 10.1007/s11418-015-0929-1. [PMID: 26188960]
  • Rui-fang Li, Jun-min Fu, Xing-zhi Lv, Dong-tao Zhang, Yong-yang Pan, Da-pang Rao, Kai-yuan Yu. Effects of Evodiamine on the Pharmacokinetics of Dapoxetine and Its Metabolite Desmethyl Dapoxetine in Rats. Pharmacology. 2016; 97(1-2):43-7. doi: 10.1159/000441568. [PMID: 26588583]