5B8915UELW (BioDeep_00000229807)

 

Secondary id: BioDeep_00000230854, BioDeep_00000239241, BioDeep_00000863018

PANOMIX_OTCML-2023


代谢物信息卡片


ethyl (E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoate;Ferulic acid ethyl ester

化学式: C12H14O4 (222.0892044)
中文名称: 阿魏酸乙酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 33%

分子结构信息

SMILES: CCOC(=O)C=CC1=CC(=C(C=C1)O)OC
InChI: InChI=1S/C12H14O4/c1-3-16-12(14)7-5-9-4-6-10(13)11(8-9)15-2/h4-8,13H,3H2,1-2H3/b7-5+

描述信息

Ethyl ferulate is a natural product found in Tocoyena formosa, Coptis japonica, and other organisms with data available.
C26170 - Protective Agent > C275 - Antioxidant
Ethyl ferulate, a naturally lipophilic derivative of ferulic acid originally derived from Rhizoma Chuanxiong, induces heme oxygenase-1 (HO-1) and protects rat neurons against oxidative stress[1]. Ethyl ferulate also protects neurons against amyloid β peptide (1-42)-induced oxidative stress and neurotoxicity[2].
Ethyl ferulate, a naturally lipophilic derivative of ferulic acid originally derived from Rhizoma Chuanxiong, induces heme oxygenase-1 (HO-1) and protects rat neurons against oxidative stress[1]. Ethyl ferulate also protects neurons against amyloid β peptide (1-42)-induced oxidative stress and neurotoxicity[2].

同义名列表

29 个代谢物同义名

ethyl (E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoate;Ferulic acid ethyl ester; 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, ethyl ester, (2E)-; 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, ethyl ester; (E)-3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid ethyl ester; Ethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate; Ethyl (2e)-3-(4-Hydroxy-3-Methoxyphenyl)prop-2-Enoate; ethyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate; ethyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate; (E)-Ethyl 3-(4-hydroxy-3-methoxyphenyl)acrylate; ethyl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate; (E)-Ethyl3-(4-hydroxy-3-methoxyphenyl)acrylate; ethyl 3-(4-hydroxy-3-methoxyphenyl)acrylate; Ethyl 4-hydroxy-3-methoxycinnamate, 98\\%; ethyl (E)-4-hydroxy-3-methoxycinnamate; (E)-3-(4-Hydroxy-3-methoxy-phenyl)-; ethyl 4-hydroxy-3-methoxycinnamate; Ethyl 4-hydroxy-3-methoxycinnamate; ETHYL 4-HYDROXY-3-METHOXYCINNAMAT; Ethyl ferulate - Natural grade; ferulic acid, ethyl ester; Ferulic acid ethyl ester; ETHYL FERULATE [INCI]; Ethyl (E)-ferulate; UNII-5B8915UELW; Ethyl ferulate; ORISTRACT EF; NOMCORT EF; 5B8915UELW; AI3-23714



数据库引用编号

8 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)

1 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

  • Chang Shu, Xiuxiu Sun, Jiankang Cao, Samir Droby, Weibo Jiang. Antifungal efficiency and mechanisms of ethyl ferulate against postharvest pathogens. International journal of food microbiology. 2024 Jun; 417(?):110710. doi: 10.1016/j.ijfoodmicro.2024.110710. [PMID: 38643598]
  • Ke-Feng Zeng, Hui-Juan Wang, Bo Deng, Ting-Fang Chen, Jun-Bang Chen, Wen-Jun Ding, Si Chen, Jun-di Xie, Si-Min Lu, Guang-Hong Chen, Ying Zhang, Zhang-Bin Tan, Hong-Bin Ou, Yong-Zhen Tan, Shuang-Wei Zhang, Ying-Chun Zhou, Jing-Zhi Zhang, Bin Liu. Ethyl ferulate suppresses post-myocardial infarction myocardial fibrosis by inhibiting transforming growth factor receptor 1. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Sep; 121(?):155118. doi: 10.1016/j.phymed.2023.155118. [PMID: 37801895]
  • Sangeun Jeon, Jisub Hwang, Hackwon Do, Ly Thi Huong Luu Le, Chang Woo Lee, Wanki Yoo, Min Ju Lee, Seung Chul Shin, Kyeong Kyu Kim, Han-Woo Kim, Jun Hyuck Lee. Feruloyl Esterase (LaFae) from Lactobacillus acidophilus: Structural Insights and Functional Characterization for Application in Ferulic Acid Production. International journal of molecular sciences. 2023 Jul; 24(13):. doi: 10.3390/ijms241311170. [PMID: 37446348]
  • Aakruti Arun Kaikini, Suraj Muke, Vaibhavi Peshattiwar, Sneha Bagle, Vikas Dighe, Sadhana Sathaye. Ethyl ferulate, a lipophilic phenylpropanoid, prevents diabetes-associated renal injury in rats by amelioration of hyperglycemia-induced oxidative stress via activation of nuclear factor erythroid 2-related factor 2. Journal of food biochemistry. 2021 04; 45(4):e13607. doi: 10.1111/jfbc.13607. [PMID: 33587296]
  • Piraporn Sombutsuwan, Apiwat Jirattisakul, Akkaradech Nakornsadet, Saengchai Akepratumchai, Salisa Chumsantea, Siriluck Pojjanapornpun, Supathra Lilitchan, Kanit Krisnangkura, Kornkanok Aryusuk. A Simple and Efficient Method for Synthesis and Extraction of Ethyl Ferulate from γ-Oryzanol. Journal of oleo science. 2021; 70(6):757-767. doi: 10.5650/jos.ess20180. [PMID: 34078757]
  • Guangxin Sun, Michael Strebl, Maximilian Merz, Robert Blamberg, Fong-Chin Huang, Kate McGraphery, Thomas Hoffmann, Wilfried Schwab. Glucosylation of the phytoalexin N-feruloyl tyramine modulates the levels of pathogen-responsive metabolites in Nicotiana benthamiana. The Plant journal : for cell and molecular biology. 2019 10; 100(1):20-37. doi: 10.1111/tpj.14420. [PMID: 31124249]
  • Yuan Jia, Ying He, Fachuang Lu. The structure-antioxidant activity relationship of dehydrodiferulates. Food chemistry. 2018 Dec; 269(?):480-485. doi: 10.1016/j.foodchem.2018.07.038. [PMID: 30100463]
  • Haiping Zhang, Mingming Zheng, Jie Shi, Hu Tang, Qianchun Deng, Fenghong Huang, Dan Luo. Enzymatic preparation of 'functional oil' rich in feruloylated structured lipids with solvent-free ultrasound pretreatment. Food chemistry. 2018 May; 248(?):272-278. doi: 10.1016/j.foodchem.2017.12.069. [PMID: 29329854]
  • Xujian Qiu, Charlotte Jacobsen, Pierre Villeneuve, Erwann Durand, Ann-Dorit Moltke Sørensen. Effects of Different Lipophilized Ferulate Esters in Fish Oil-Enriched Milk: Partitioning, Interaction, Protein, and Lipid Oxidation. Journal of agricultural and food chemistry. 2017 Nov; 65(43):9496-9505. doi: 10.1021/acs.jafc.7b02994. [PMID: 29048172]
  • David L Compton, Kervin O Evans, Michael Appell. Experimental and theoretical study of the influence of water on hydrolyzed product formation during the feruloylation of vegetable oil. Journal of the science of food and agriculture. 2017 Jul; 97(9):3022-3029. doi: 10.1002/jsfa.8145. [PMID: 27859298]
  • Vijay P Sonar, Angela Corona, Simona Distinto, Elias Maccioni, Rita Meleddu, Benedetta Fois, Costantino Floris, Nilesh V Malpure, Stefano Alcaro, Enzo Tramontano, Filippo Cottiglia. Natural product-inspired esters and amides of ferulic and caffeic acid as dual inhibitors of HIV-1 reverse transcriptase. European journal of medicinal chemistry. 2017 Apr; 130(?):248-260. doi: 10.1016/j.ejmech.2017.02.054. [PMID: 28254698]
  • Magdalena Karamać, Lidiya Koleva, Vessela D Kancheva, Ryszard Amarowicz. The Structure-Antioxidant Activity Relationship of Ferulates. Molecules (Basel, Switzerland). 2017 Mar; 22(4):. doi: 10.3390/molecules22040527. [PMID: 28346342]
  • Martin Waterstraat, Diana Bunzel, Mirko Bunzel. Identification of 8-O-4/8-5(Cyclic)- and 8-8(Cyclic)/5-5-Coupled Dehydrotriferulic Acids, Naturally Occurring in Cell Walls of Mono- and Dicotyledonous Plants. Journal of agricultural and food chemistry. 2016 Sep; 64(38):7244-50. doi: 10.1021/acs.jafc.6b02720. [PMID: 27540862]
  • Cheng Jiang, Pan Luo, Yu Zhao, Jialing Hong, Susan L Morris-Natschke, Jun Xu, Chin-Ho Chen, Kuo-Hsiung Lee, Qiong Gu. Carolignans from the Aerial Parts of Euphorbia sikkimensis and Their Anti-HIV Activity. Journal of natural products. 2016 Mar; 79(3):578-83. doi: 10.1021/acs.jnatprod.5b01012. [PMID: 26756779]
  • Dan Zhu, Antoni Sánchez-Ferrer, Laura Nyström. Antioxidant Activity of Individual Steryl Ferulates from Various Cereal Grain Sources. Journal of natural products. 2016 Feb; 79(2):308-16. doi: 10.1021/acs.jnatprod.5b00880. [PMID: 26790041]
  • Shangde Sun, Sha Zhu, Yanlan Bi. Solvent-free enzymatic synthesis of feruloylated structured lipids by the transesterification of ethyl ferulate with castor oil. Food chemistry. 2014 Sep; 158(?):292-5. doi: 10.1016/j.foodchem.2014.02.146. [PMID: 24731344]
  • Shangde Sun, Wenya Zhou. Enhanced enzymatic preparation of lipophilic feruloylated lipids using distearin as feruloyl acceptors: optimization by response surface methodology. Journal of oleo science. 2014; 63(10):1011-8. doi: 10.5650/jos.ess14095. [PMID: 25213445]
  • Shangde Sun, Fei Qin, Yanlan Bi, Jingnan Chen, Guolong Yang, Wei Liu. Enhanced transesterification of ethyl ferulate with glycerol for preparing glyceryl diferulate using a lipase in ionic liquids as reaction medium. Biotechnology letters. 2013 Sep; 35(9):1449-54. doi: 10.1007/s10529-013-1222-6. [PMID: 23690034]
  • Fachuang Lu, Liping Wei, Ali Azarpira, John Ralph. Rapid syntheses of dehydrodiferulates via biomimetic radical coupling reactions of ethyl ferulate. Journal of agricultural and food chemistry. 2012 Aug; 60(34):8272-7. doi: 10.1021/jf302140k. [PMID: 22846085]
  • Kin Kwan Lai, Graciela L Lorca, Claudio F Gonzalez. Biochemical properties of two cinnamoyl esterases purified from a Lactobacillus johnsonii strain isolated from stool samples of diabetes-resistant rats. Applied and environmental microbiology. 2009 Aug; 75(15):5018-24. doi: 10.1128/aem.02837-08. [PMID: 19502437]
  • David L Compton, Joseph A Laszlo. 1,3-Diferuloyl-sn-glycerol from the biocatalytic transesterification of ethyl 4-hydroxy-3-methoxy cinnamic acid (ethyl ferulate) and soybean oil. Biotechnology letters. 2009 Jun; 31(6):889-96. doi: 10.1007/s10529-009-9952-1. [PMID: 19238329]
  • Aiping Zhang, Fachuang Lu, Runcang Sun, John Ralph. Ferulate-coniferyl alcohol cross-coupled products formed by radical coupling reactions. Planta. 2009 Apr; 229(5):1099-108. doi: 10.1007/s00425-009-0894-6. [PMID: 19234718]
  • Vittorio Calabrese, Stella Calafato, Eduardo Puleo, Carolin Cornelius, Maria Sapienza, Pierfrancesco Morganti, Cesare Mancuso. Redox regulation of cellular stress response by ferulic acid ethyl ester in human dermal fibroblasts: role of vitagenes. Clinics in dermatology. 2008 Jul; 26(4):358-63. doi: 10.1016/j.clindermatol.2008.01.005. [PMID: 18691515]
  • Liang Kong, Zhiyuan Yu, Yongming Bao, Xingye Su, Hanfa Zou, Xin Li. Screening and analysis of an antineoplastic compound in Rhizoma Chuanxiong by means of in vitro metabolism and HPLC-MS. Analytical and bioanalytical chemistry. 2006 Sep; 386(2):264-74. doi: 10.1007/s00216-006-0621-0. [PMID: 16868728]
  • Marzia Perluigi, Gururaj Joshi, Rukhsana Sultana, Vittorio Calabrese, Carlo De Marco, Raffaella Coccia, Chiara Cini, D Allan Butterfield. In vivo protective effects of ferulic acid ethyl ester against amyloid-beta peptide 1-42-induced oxidative stress. Journal of neuroscience research. 2006 Aug; 84(2):418-26. doi: 10.1002/jnr.20879. [PMID: 16634068]
  • Gururaj Joshi, Marzia Perluigi, Rukhsana Sultana, Ravagna Agrippino, Vittorio Calabrese, D Allan Butterfield. In vivo protection of synaptosomes by ferulic acid ethyl ester (FAEE) from oxidative stress mediated by 2,2-azobis(2-amidino-propane)dihydrochloride (AAPH) or Fe(2+)/H(2)O(2): insight into mechanisms of neuroprotection and relevance to oxidative stress-related neurodegenerative disorders. Neurochemistry international. 2006 Mar; 48(4):318-27. doi: 10.1016/j.neuint.2005.11.006. [PMID: 16386335]
  • Rukhsana Sultana, Agrippino Ravagna, Hafiz Mohmmad-Abdul, Vittorio Calabrese, D Allan Butterfield. Ferulic acid ethyl ester protects neurons against amyloid beta- peptide(1-42)-induced oxidative stress and neurotoxicity: relationship to antioxidant activity. Journal of neurochemistry. 2005 Feb; 92(4):749-58. doi: 10.1111/j.1471-4159.2004.02899.x. [PMID: 15686476]
  • Giovanni Scapagnini, D Allan Butterfield, Claudia Colombrita, Rukhsana Sultana, Alessia Pascale, Vittorio Calabrese. Ethyl ferulate, a lipophilic polyphenol, induces HO-1 and protects rat neurons against oxidative stress. Antioxidants & redox signaling. 2004 Oct; 6(5):811-8. doi: 10.1089/ars.2004.6.811. [PMID: 15345140]
  • M A Edeas, C Claise, L Vergnes, Y Khalfoun, S Barthelemy, S Labidalle, A Lindenbaum. Protective effects of the lipophilic redox conjugate tocopheryl succinyl-ethyl ferulate on HIV replication. FEBS letters. 1997 Nov; 418(1-2):15-8. doi: 10.1016/s0014-5793(97)01335-5. [PMID: 9414085]
  • S Tawata, S Taira, N Kobamoto, J Zhu, M Ishihara, S Toyama. Synthesis and antifungal activity of cinnamic acid esters. Bioscience, biotechnology, and biochemistry. 1996 May; 60(5):909-10. doi: 10.1271/bbb.60.909. [PMID: 8704323]