Methyl_caffeate (BioDeep_00000396764)

 

Secondary id: BioDeep_00000002651, BioDeep_00000174042

PANOMIX_OTCML-2023 Antitumor activity Volatile Flavor Compounds


代谢物信息卡片


2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, methyl ester, (E)-

化学式: C10H10O4 (194.057906)
中文名称: 咖啡酸甲酯
谱图信息: 最多检出来源 Astragalus membranaceus(otcml) 28.21%

分子结构信息

SMILES: c1(c(ccc(c1)/C=C/C(=O)OC)O)O
InChI: InChI=1S/C10H10O4/c1-14-10(13)5-3-7-2-4-8(11)9(12)6-7/h2-6,11-12H,1H3/b5-3+

描述信息

Methyl caffeate is an alkyl caffeate ester formed by the formal condensation of caffeic acid with methyl alcohol. It is an alkyl caffeate ester and a methyl ester.
Methyl caffeate is a natural product found in Smilax bracteata, Fumaria capreolata, and other organisms with data available.
See also: Black Cohosh (part of).
An ester formed by the formal condensation of caffeic acid with methyl alcohol.
Methyl caffeate, an antimicrobial agent, shows moderate antimicrobial and prominent antimycobacterial activities. Methyl caffeate also exhibits α-glucosidase inhibition activity, oxidative stress inhibiting activity, anti-platelet activity, antiproliferative activity in cervix adenocarcinoma and anticancer activity in lung and leukmia cell lines[1].
Methyl caffeate, an antimicrobial agent, shows moderate antimicrobial and prominent antimycobacterial activities. Methyl caffeate also exhibits α-glucosidase inhibition activity, oxidative stress inhibiting activity, anti-platelet activity, antiproliferative activity in cervix adenocarcinoma and anticancer activity in lung and leukmia cell lines[1].

同义名列表

29 个代谢物同义名

2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, methyl ester, (E)-; (E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid methyl ester; 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, methyl ester; (E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid methyl ester; methyl (E)-3-[3,4-bis(oxidanyl)phenyl]prop-2-enoate; 3-(3,4-Dihydroxy-phenyl)-acrylic acid methyl ester; methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate; methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate; Cinnamic acid, 3,4-dihydroxy-, methyl ester; methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate; (E)-3,4-Dihydroxycinnamic Acid Methyl Ester; methyl (2E)-3-(3,4-dihydroxyphenyl)acrylate; methyl (E)-3-(3,4-dihydroxyphenyl)acrylate; (E)-methyl 3-(3,4-dihydroxyphenyl)acrylate; (E)-Methyl3-(3,4-dihydroxyphenyl)acrylate; Methyl 1-(3,4-dihydroxyphenyl)propenate; Methyl 1-(3,4-Dihydroxyphenyl)Propenate; methyl 3-(3,4-dihydroxyphenyl)acrylate; methyl-3,4-dihydroxy cinnamate; Methyl 3,4-dihydroxycinnamate; (E)-Caffeic acid methyl ester; E-Caffeic acid methyl ester; Caffeic acid, methyl ester; Caffeic acid methyl ester; Methyl caffeate acid; Methyl caffeate; METHYLCAFFEATE; Methyl caffeate; Methyl caffeate



数据库引用编号

19 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)

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

  • Dahae Lee, Ji-Young Kim, Yutong Qi, Sangsu Park, Hye Lim Lee, Noriko Yamabe, Hocheol Kim, Dae Sik Jang, Ki Sung Kang. Phytochemicals from the flowers of Prunus persica (L.) Batsch: Anti-adipogenic effect of mandelamide on 3T3-L1 preadipocytes. Bioorganic & medicinal chemistry letters. 2021 10; 49(?):128326. doi: 10.1016/j.bmcl.2021.128326. [PMID: 34403725]
  • Haowen Zhang, Boting Wen, Yusi Liu, Guoming Du, Xue Wei, Khandaker Md Sharif Uddin Imam, Huan Zhou, Shilong Fan, Fengzhong Wang, Yulu Wang, Fengjiao Xin. A reverse catalytic triad Asp containing loop shaping a wide substrate binding pocket of a feruloyl esterase from Lactobacillus plantarum. International journal of biological macromolecules. 2021 Aug; 184(?):92-100. doi: 10.1016/j.ijbiomac.2021.06.033. [PMID: 34116094]
  • Laura Fási, Ahmed Dhahir Latif, István Zupkó, Sándor Lévai, Miklós Dékány, Zoltán Béni, Árpád Könczöl, György Tibor Balogh, Attila Hunyadi. AAPH or Peroxynitrite-Induced Biorelevant Oxidation of Methyl Caffeate Yields a Potent Antitumor Metabolite. Biomolecules. 2020 11; 10(11):. doi: 10.3390/biom10111537. [PMID: 33187226]
  • Young H Seo, Shin-Young Kang, Ji-Sun Shin, Seung M Ryu, A Y Lee, Goya Choi, Byeong C Moon, Dae-Sik Jang, Sang H Shim, Dongho Lee, Kyung-Tae Lee, Jun Lee. Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E2 Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages. Journal of natural products. 2019 12; 82(12):3379-3385. doi: 10.1021/acs.jnatprod.9b00697. [PMID: 31747281]
  • Sirinapa Chaipon, Prapaipit Suwitchayanon, Arihiro Iwasaki, Kiyotake Suenaga, Hisashi Kato-Noguchi. Isolation and identification of a growth inhibitory substance from Heliotropium indicum L. Acta biologica Hungarica. 2018 Sep; 69(3):259-269. doi: 10.1556/018.68.2018.3.3. [PMID: 30257579]
  • Janggyoo Choi, Kee Dong Yoon, Jinwoong Kim. Chemical constituents from Taraxacum officinale and their α-glucosidase inhibitory activities. Bioorganic & medicinal chemistry letters. 2018 02; 28(3):476-481. doi: 10.1016/j.bmcl.2017.12.014. [PMID: 29254644]
  • Young-Ran Song, Sang-Ho Baik. Molecular cloning, purification, and characterization of a novel thermostable cinnamoyl esterase from Lactobacillus helveticus KCCM 11223. Preparative biochemistry & biotechnology. 2017 May; 47(5):496-504. doi: 10.1080/10826068.2016.1275011. [PMID: 28045590]
  • Hyun Lim, Byung Kyu Park, Sook Young Shin, Yong Soo Kwon, Hyun Pyo Kim. Methyl caffeate and some plant constituents inhibit age-related inflammation: effects on senescence-associated secretory phenotype (SASP) formation. Archives of pharmacal research. 2017 Apr; 40(4):524-535. doi: 10.1007/s12272-017-0909-y. [PMID: 28299617]
  • Zheng-yi Qu, Yu-wei Zhang, Si-Wen Zheng, Chun-lin Yao, Yin-ping Jin, Pei-he Zheng, Cheng-he Sun, Ying-ping Wang. A new phenylethanoid glycoside from Orobanche cernua Loefling. Natural product research. 2016; 30(8):948-53. doi: 10.1080/14786419.2015.1084305. [PMID: 26358786]
  • Chun-Hsu Pan, Wen-Hsin Lin, Yi-Chung Chien, Fon-Chang Liu, Ming-Jyh Sheu, Yueh-Hsiung Kuo, Chieh-Hsi Wu. K20E, an oxidative-coupling compound of methyl caffeate, exhibits anti-angiogenic activities through down-regulations of VEGF and VEGF receptor-2. Toxicology and applied pharmacology. 2015 Jan; 282(2):215-26. doi: 10.1016/j.taap.2014.11.009. [PMID: 25481497]
  • Rukaiyya Sirajuddin Khan, Mahibalan Senthi, Poorna Chandra Rao, Ameer Basha, Mallika Alvala, Dinesh Tummuri, Hironori Masubuti, Yoshinori Fujimoto, Ahil Sajeli Begum. Cytotoxic constituents of Abutilon indicum leaves against U87MG human glioblastoma cells. Natural product research. 2015; 29(11):1069-73. doi: 10.1080/14786419.2014.976643. [PMID: 25422029]
  • Takeshi Yokoyama, Yuto Kosaka, Mineyuki Mizuguchi. Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin. Journal of medicinal chemistry. 2014 Nov; 57(21):8928-35. doi: 10.1021/jm500997m. [PMID: 25314129]
  • Mansour Znati, Hichem Ben Jannet, Sylvie Cazaux, Jean Pierre Souchard, Féthia Harzallah Skhiri, Jalloul Bouajila. Antioxidant, 5-lipoxygenase inhibitory and cytotoxic activities of compounds isolated from the Ferula lutea flowers. Molecules (Basel, Switzerland). 2014 Oct; 19(10):16959-75. doi: 10.3390/molecules191016959. [PMID: 25340301]
  • María Esteban-Torres, Inés Reverón, José Miguel Mancheño, Blanca de Las Rivas, Rosario Muñoz. Characterization of a feruloyl esterase from Lactobacillus plantarum. Applied and environmental microbiology. 2013 Sep; 79(17):5130-6. doi: 10.1128/aem.01523-13. [PMID: 23793626]
  • Aya Fujimoto, Miyuki Inai, Toshiya Masuda. Chemical evidence for the synergistic effect of a cysteinyl thiol on the antioxidant activity of caffeic and dihydrocaffeic esters. Food chemistry. 2013 Jun; 138(2-3):1483-92. doi: 10.1016/j.foodchem.2012.11.073. [PMID: 23411271]
  • Jonathan Negrel, Francine Javelle, Dominique Morandi. Detection of a plant enzyme exhibiting chlorogenate-dependant caffeoyltransferase activity in methanolic extracts of arbuscular mycorrhizal tomato roots. Plant physiology and biochemistry : PPB. 2013 May; 66(?):77-83. doi: 10.1016/j.plaphy.2013.02.009. [PMID: 23500709]
  • Agnieszka Kicel, Maria Wolbiś. Study on the phenolic constituents of the flowers and leaves of Trifolium repens L. Natural product research. 2012 Nov; 26(21):2050-4. doi: 10.1080/14786419.2011.637217. [PMID: 22117193]
  • Gopalsamy Rajiv Gandhi, Savarimuthu Ignacimuthu, Michael Gabriel Paulraj, Ponnusamy Sasikumar. Antihyperglycemic activity and antidiabetic effect of methyl caffeate isolated from Solanum torvum Swartz. fruit in streptozotocin induced diabetic rats. European journal of pharmacology. 2011 Nov; 670(2-3):623-31. doi: 10.1016/j.ejphar.2011.09.159. [PMID: 21963451]
  • Armin Wagner, Yuki Tobimatsu, Lorelle Phillips, Heather Flint, Kirk Torr, Lloyd Donaldson, Lana Pears, John Ralph. CCoAOMT suppression modifies lignin composition in Pinus radiata. The Plant journal : for cell and molecular biology. 2011 Jul; 67(1):119-29. doi: 10.1111/j.1365-313x.2011.04580.x. [PMID: 21426426]
  • John H Grabber, Paul F Schatz, Hoon Kim, Fachuang Lu, John Ralph. Identifying new lignin bioengineering targets: 1. Monolignol-substitute impacts on lignin formation and cell wall fermentability. BMC plant biology. 2010 Jun; 10(?):114. doi: 10.1186/1471-2229-10-114. [PMID: 20565789]
  • Yu Fu, Yang Bai, Zhuoma Dawa, Bingru Bai, Lisheng Ding. [Chemical constituents of Incarvillea younghusbandii]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Jan; 35(1):58-62. doi: 10.4268/cjcmm20100112. [PMID: 20349717]
  • Shuang Liang, Yun-Heng Shen, Jun-Mian Tian, Zhi-Jun Wu, Hui-Zi Jin, Wei-Dong Zhang, Shi-Kai Yan. Phenylpropanoids from Daphne feddei and their inhibitory activities against NO production. Journal of natural products. 2008 Nov; 71(11):1902-5. doi: 10.1021/np8004166. [PMID: 18986199]
  • Toshiya Masuda, Kazuki Yamada, Jun Akiyama, Tatsushi Someya, Yuka Odaka, Yoshio Takeda, Motoo Tori, Katsuyuki Nakashima, Tomomi Maekawa, Yoshiaki Sone. Antioxidation mechanism studies of caffeic acid: identification of antioxidation products of methyl caffeate from lipid oxidation. Journal of agricultural and food chemistry. 2008 Jul; 56(14):5947-52. doi: 10.1021/jf800781b. [PMID: 18558705]
  • Stefano Dall'Acqua, Giampietro Viola, Sonia Piacente, Elsa Mariella Cappelletti, Gabbriella Innocenti. Cytotoxic constituents of roots of Chaerophyllum hirsutum. Journal of natural products. 2004 Sep; 67(9):1588-90. doi: 10.1021/np040046w. [PMID: 15387667]