Isoferulic acid (BioDeep_00000230832)

Main id: BioDeep_00000400555

Secondary id: BioDeep_00000001210, BioDeep_00000229793, BioDeep_00000864435

human metabolite PANOMIX_OTCML-2023 blood metabolite Volatile Flavor Compounds natural product


代谢物信息卡片


3-Hydroxy-4-methoxycinnamic acid, predominantly trans, 97\\%

化学式: C10H10O4 (194.057906)
中文名称: 异阿魏酸, 反式异阿魏酸, 3-羟基-4-甲氧基肉桂酸
谱图信息: 最多检出来源 Viridiplantae(plant) 23.65%

分子结构信息

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

描述信息

Isoferulic acid (CAS: 537-73-5) is a chlorogenic acid (CGA). CGAs are formed by the esterification of hydroxycinnamic acids (e.g. caffeic acid, ferulic acid, and p-coumaric acid) with quinic acid. CGAs are abundant phenolic compounds in coffee, with caffeoylquinic (CQA), feruloylquinic (FQA), and dicaffeoylquinic (diCQA) acids being the major subclasses, and coffee is the most consumed food product in the world. Isoferulic acid is present in normal human urine in concentrations of 0.05-2.07 umol/mmol creatinine at baseline, and reaches 0.2-9.6 umol/mmol creatinine in four hours after a cup of coffee, with a large inter-individual variation (PMID:17884997).
Isoferulic acid is a ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring. It has a role as a metabolite, a biomarker and an antioxidant.
Isoferulic acid is a natural product found in Sibiraea angustata, Astragalus onobrychis, and other organisms with data available.
See also: Black Cohosh (part of); Ipomoea aquatica leaf (part of).
A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring.
It is used as a food additive; listed in the EAFUS Food Additive Database (Jan 2001)
Isoferulic acid (3-Hydroxy-4-methoxycinnamic acid) is a cinnamic acid derivative that has antidiabetic activity. Isoferulic acid binds to and activates α1-adrenergic receptors (IC50=1.4 μM) to enhance secretion of β-endorphin (EC50=52.2 nM) and increase glucose use. Isoferulic acid also has anti-influenza virus activities.
Isoferulic acid (3-Hydroxy-4-methoxycinnamic acid) is a cinnamic acid derivative that has antidiabetic activity. Isoferulic acid binds to and activates α1-adrenergic receptors (IC50=1.4 μM) to enhance secretion of β-endorphin (EC50=52.2 nM) and increase glucose use. Isoferulic acid also has anti-influenza virus activities.
Isoferulic acid (3-Hydroxy-4-methoxycinnamic acid) is a cinnamic acid derivative that has antidiabetic activity. Isoferulic acid binds to and activates α1-adrenergic receptors (IC50=1.4 μM) to enhance secretion of β-endorphin (EC50=52.2 nM) and increase glucose use. Isoferulic acid also has anti-influenza virus activities.
trans-Isoferulic acid (trans-3-Hydroxy-4-methoxycinnamic acid) is an aromatic acid isolated from the roots of Clematis florida var. plena. trans-Isoferulic acid exhibits anti-inflammatory activity[1].trans-isoferulic acid suppresses NO and PGE2 production through the induction of Nrf2-dependent heme oxygenase-1 (HO-1)[2].
trans-Isoferulic acid (trans-3-Hydroxy-4-methoxycinnamic acid) is an aromatic acid isolated from the roots of Clematis florida var. plena. trans-Isoferulic acid exhibits anti-inflammatory activity[1].trans-isoferulic acid suppresses NO and PGE2 production through the induction of Nrf2-dependent heme oxygenase-1 (HO-1)[2].

同义名列表

57 个代谢物同义名

3-Hydroxy-4-methoxycinnamic acid, predominantly trans, 97\\%; (E)-4-Hydroxy-4-(6-methoxynaphthalen-2-yl)but-3-en-2-one; (2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid #; 3-Hydroxy-4-methoxycinnamic acid, predominantly trans; (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid; 3-[3-Hydroxy-4-(methoxy-d3)phenyl]-2-propenoic Acid; ISOFERULIC ACID (CONSTITUENT OF BLACK COHOSH) [DSC]; (2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid; (e)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid; (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid; 3-Hydroxy-4-methoxycinnamic acid (isoferulic acid); 2-Propenoic acid, 3-(3-hydroxy-4-methoxyphenyl)-; (2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoate; (E)-3-(3-hydroxy-4-methoxy-phenyl)-acrylic acid; (2E)-3-(3-HYDROXY-4-METHOXYPHENYL)ACRYLIC ACID; 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid; 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid; ISOFERULIC ACID (CONSTITUENT OF BLACK COHOSH); (E)-3-(3-hydroxy-4-methoxyphenyl)acrylic acid; 4-10-00-01777 (Beilstein Handbook Reference); (E)-3-(3-hydroxy-4-methoxyphenyl)acrylicacid; trans-Isoferulic acid, analytical standard; 3-(3-hydroxy-4-methoxyphenyl)-2-Propenoate; 3-(3-Hydroxy-4-methoxyphenyl)acrylic acid; trans-3-Hydroxy-4-methoxycinnamic acid; (E)-3-Hydroxy-4-methoxycinnamic acid; (e)-3-Hydroxy-4-methoxycinnamic acid; Cinnamic acid, 3-hydroxy-4-methoxy-; 3-hydroxy-4-methoxy-cinnamic acid; 3-hydroxy-4-methoxycinnamic acid; 3-Hydroxy-4-methoxycinnamic acid; 3-Hydroxy-4-methoxycinnamic-acid; 3-hydroxy-4-methoxy-Cinnamate; 3-Hydroxy-4-methoxycinnamate; trans-4-O-Methylcaffeic acid; trans-4-Methoxycaffeic acid; (e)-4-O-Methylcaffeic acid; (e)-4-Methoxycaffeic acid; 4-O-METHYLCAFFEIC ACID; trans-Isoferulic acid; trans-Hesperetic acid; 4-Methoxycaffeic acid; Isoferulic Acid ,(S); cis-Isoferulic acid; (e)-Hesperetic acid; (e)-Isoferulic acid; Hesperetinic acid; Hesperetic acid; Isoferulic acid; UNII-XSQ2K2G7MC; Isoferulasaure; Isoferulate; Hesperetate; XSQ2K2G7MC; Isoferulic; 4FE; Isoferulic acid



数据库引用编号

26 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)

243 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

  • Vera A Kostikova, Natalia V Petrova, Alexander A Chernonosov, Vladimir V Koval, Evgeniia R Kovaleva, Wei Wang, Andrey S Erst. Chemical Composition of Methanol Extracts from Leaves and Flowers of Anemonopsis macrophylla (Ranunculaceae). International journal of molecular sciences. 2024 Jan; 25(2):. doi: 10.3390/ijms25020989. [PMID: 38256067]
  • Julia Wohl, Maike Petersen. Phenolic metabolism in the hornwort Anthoceros agrestis: 4-coumarate CoA ligase and 4-hydroxybenzoate CoA ligase. Plant cell reports. 2020 Sep; 39(9):1129-1141. doi: 10.1007/s00299-020-02552-w. [PMID: 32405654]
  • Sadaf Arfin, Gufran Ahmed Siddiqui, Aabgeena Naeem, Shagufta Moin. Inhibition of advanced glycation end products by isoferulic acid and its free radical scavenging capacity: An in vitro and molecular docking study. International journal of biological macromolecules. 2018 Oct; 118(Pt B):1479-1487. doi: 10.1016/j.ijbiomac.2018.06.182. [PMID: 29969636]
  • Evelien Van Rymenant, Bouke Salden, Stefan Voorspoels, Griet Jacobs, Bart Noten, Judit Pitart, Sam Possemiers, Guy Smagghe, Charlotte Grootaert, John Van Camp. A Critical Evaluation of In Vitro Hesperidin 2S Bioavailability in a Model Combining Luminal (Microbial) Digestion and Caco-2 Cell Absorption in Comparison to a Randomized Controlled Human Trial. Molecular nutrition & food research. 2018 04; 62(8):e1700881. doi: 10.1002/mnfr.201700881. [PMID: 29451355]
  • D S Jairajpuri, Z S Jairajpuri. Isoferulic Acid Action against Glycation-Induced Changes in Structural and Functional Attributes of Human High-Density Lipoprotein. Biochemistry. Biokhimiia. 2016 Mar; 81(3):289-95. doi: 10.1134/s0006297916030123. [PMID: 27262199]
  • Aramsri Meeprom, Weerachat Sompong, Tanyawan Suantawee, Thavaree Thilavech, Catherine B Chan, Sirichai Adisakwattana. Isoferulic acid prevents methylglyoxal-induced protein glycation and DNA damage by free radical scavenging activity. BMC complementary and alternative medicine. 2015 Oct; 15(?):346. doi: 10.1186/s12906-015-0874-2. [PMID: 26438049]
  • Grażyna Szymczak, Magdalena Wójciak-Kosior, Ireneusz Sowa, Karolina Zapała, Anna Bogucka-Kocka. Comparison of phenolic content and antioxidant activity of Actaea racemosa L. and Actaea cordifolia DC. Natural product research. 2015; 29(12):1149-52. doi: 10.1080/14786419.2014.980254. [PMID: 25427941]
  • Matharage Gayani Dilshara, Kyoung-Tae Lee, Rajapaksha Gedara Prasad Tharanga Jayasooriya, Chang-Hee Kang, Sang Rul Park, Yung Hyun Choi, Il-Whan Choi, Jin-Won Hyun, Weon-Young Chang, Yeon-Su Kim, Hak-Ju Lee, Gi-Young Kim. Downregulation of NO and PGE2 in LPS-stimulated BV2 microglial cells by trans-isoferulic acid via suppression of PI3K/Akt-dependent NF-κB and activation of Nrf2-mediated HO-1. International immunopharmacology. 2014 Jan; 18(1):203-11. doi: 10.1016/j.intimp.2013.11.020. [PMID: 24291391]
  • Fei Wang, Shancang Zhao, Feng Li, Bo Zhang, Yi Qu, Tianlei Sun, Ting Luo, Dapeng Li. Investigation of antioxidant interactions between Radix Astragali and Cimicifuga foetida and identification of synergistic antioxidant compounds. PloS one. 2014; 9(1):e87221. doi: 10.1371/journal.pone.0087221. [PMID: 24498048]
  • Aramsri Meeprom, Weerachat Sompong, Catherine B Chan, Sirichai Adisakwattana. Isoferulic acid, a new anti-glycation agent, inhibits fructose- and glucose-mediated protein glycation in vitro. Molecules (Basel, Switzerland). 2013 May; 18(6):6439-54. doi: 10.3390/molecules18066439. [PMID: 23722732]
  • Jan Heinrich, Kateřina Valentová, Jan Vacek, Irena Palíková, Martina Zatloukalová, Pavel Kosina, Jitka Ulrichová, Jana Vrbková, Vilím Šimánek. Metabolic profiling of phenolic acids and oxidative stress markers after consumption of Lonicera caerulea L. fruit. Journal of agricultural and food chemistry. 2013 May; 61(19):4526-32. doi: 10.1021/jf304150b. [PMID: 23581742]
  • Ji Sang Hwang, Seon A Lee, Seong Su Hong, Xiang Hua Han, Chul Lee, Dongho Lee, Chong-Kil Lee, Jin Tae Hong, Youngsoo Kim, Mi Kyeong Lee, Bang Yeon Hwang. Inhibitory constituents of Nardostachys chinensis on nitric oxide production in RAW 264.7 macrophages. Bioorganic & medicinal chemistry letters. 2012 Jan; 22(1):706-8. doi: 10.1016/j.bmcl.2011.10.043. [PMID: 22079762]
  • Li Liu, Hongyue Ma, Yuping Tang, Wenxing Chen, Yin Lu, Jianming Guo, Jin-Ao Duan. Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells. Bioorganic & medicinal chemistry letters. 2012 Jan; 22(1):154-63. doi: 10.1016/j.bmcl.2011.11.041. [PMID: 22137340]
  • Xiaozhen Wang, Xican Li, Dongfeng Chen. Evaluation of antioxidant activity of isoferulic acid in vitro. Natural product communications. 2011 Sep; 6(9):1285-8. doi: . [PMID: 21941899]
  • Ying Zhang, Yi Yuan, Baosong Cui, Shuai Li. [Study on chemical constituents from ethyl acetate extract of Myricaria bracteata]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Apr; 36(8):1019-23. doi: . [PMID: 21809576]
  • Chi Chun Wong, Walter Meinl, Hans-Rudolf Glatt, Denis Barron, Angélique Stalmach, Heike Steiling, Alan Crozier, Gary Williamson. In vitro and in vivo conjugation of dietary hydroxycinnamic acids by UDP-glucuronosyltransferases and sulfotransferases in humans. The Journal of nutritional biochemistry. 2010 Nov; 21(11):1060-8. doi: 10.1016/j.jnutbio.2009.09.001. [PMID: 19954949]
  • Mathieu Renouf, Cynthia Marmet, Philippe Guy, Anne-Lise Fraering, Karin Longet, Julie Moulin, Marc Enslen, Denis Barron, Christophe Cavin, Fabiola Dionisi, Serge Rezzi, Sunil Kochhar, Heike Steiling, Gary Williamson. Nondairy creamer, but not milk, delays the appearance of coffee phenolic acid equivalents in human plasma. The Journal of nutrition. 2010 Feb; 140(2):259-63. doi: 10.3945/jn.109.113027. [PMID: 20007338]
  • Philippe A Guy, Mathieu Renouf, Denis Barron, Christophe Cavin, Fabiola Dionisi, Sunil Kochhar, Serge Rezzi, Gary Williamson, Heike Steiling. Quantitative analysis of plasma caffeic and ferulic acid equivalents by liquid chromatography tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Dec; 877(31):3965-74. doi: 10.1016/j.jchromb.2009.10.006. [PMID: 19879819]
  • M A M Nawwar, S A M Hussein, N A Ayoub, K Hofmann, M Linscheid, M Harms, K Wende, U Lindequist. Aphyllin, the first isoferulic acid glycoside and other phenolics from Tamarix aphylla flowers. Die Pharmazie. 2009 May; 64(5):342-7. doi: 10.1002/chin.200937206. [PMID: 19530447]
  • Na Sha, Shu-Hong Guan, Zhi-Qiang Lu, Guang-Tong Chen, Hui-Lian Huang, Fu-Bo Xie, Qing-Xi Yue, Xuan Liu, De-An Guo. Cytotoxic constituents of chinese propolis. Journal of natural products. 2009 Apr; 72(4):799-801. doi: 10.1021/np900118z. [PMID: 19278239]
  • Adriana Farah, Mariana Monteiro, Carmen M Donangelo, Sophie Lafay. Chlorogenic acids from green coffee extract are highly bioavailable in humans. The Journal of nutrition. 2008 Dec; 138(12):2309-15. doi: 10.3945/jn.108.095554. [PMID: 19022950]
  • Zi-Chuan Zhang, Man Xu, Shi-Feng Sun, Xue Qiao, Bao-Rong Wang, Jian Han, De-An Guo. Metabolic analysis of four phenolic acids in rat by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Aug; 871(1):7-14. doi: 10.1016/j.jchromb.2008.06.019. [PMID: 18603488]
  • Dandan Si, Xiaohong Sun, Dandan Qi, Xiaohui Chen, Kaishun Bi. Determination and pharmacokinetics of isoferulic acid in rat plasma by high-performance liquid chromatography after oral administration of isoferulic acid and Rhizoma Cimicifugae extract. Journal of pharmaceutical and biomedical analysis. 2008 May; 47(1):140-5. doi: 10.1016/j.jpba.2007.12.044. [PMID: 18314290]
  • Anastasia Karioti, Anastasia Protopappa, Nikolaos Megoulas, Helen Skaltsa. Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum. Bioorganic & medicinal chemistry. 2007 Apr; 15(7):2708-14. doi: 10.1016/j.bmc.2007.01.035. [PMID: 17287127]
  • Shuai Li, Ruo-Yun Chen, De-Quan Yu. [Study on chemical constituents of Myricaria paniculata I]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Mar; 32(5):403-6. doi: ". [PMID: 17511145]
  • Jinlan Zhang, Yun He, Ming Cui, Lie Li, Hailan Yu, Guifeng Zhang, Dean Guo. Metabolic studies on the total phenolic acids from the roots of Salvia miltiorrhiza in rats. Biomedical chromatography : BMC. 2005 Jan; 19(1):51-9. doi: 10.1002/bmc.415. [PMID: 15558684]
  • Jonathan M Hodgson, Shin Yee Chan, Ian B Puddey, Amanda Devine, Naiyana Wattanapenpaiboon, Mark L Wahlqvist, Widjaja Lukito, Valerie Burke, Natalie C Ward, Richard L Prince, Kevin D Croft. Phenolic acid metabolites as biomarkers for tea- and coffee-derived polyphenol exposure in human subjects. The British journal of nutrition. 2004 Feb; 91(2):301-6. doi: 10.1079/bjn20031046. [PMID: 14756917]
  • I-Min Liu, Wang-Chuan Chen, Juei-Tang Cheng. Mediation of beta-endorphin by isoferulic acid to lower plasma glucose in streptozotocin-induced diabetic rats. The Journal of pharmacology and experimental therapeutics. 2003 Dec; 307(3):1196-204. doi: 10.1124/jpet.103.053900. [PMID: 12975496]
  • So Ra Kim, So Young Kang, Ki Yong Lee, Seung Hyun Kim, George J Markelonis, Tae H Oh, Young Choong Kim. Anti-amnestic activity of E-p-methoxycinnamic acid from Scrophularia buergeriana. Brain research. Cognitive brain research. 2003 Jul; 17(2):454-61. doi: 10.1016/s0926-6410(03)00161-7. [PMID: 12880915]
  • Eun Ju Lee, So Ra Kim, Jinwoong Kim, Young Choong Kim. Hepatoprotective phenylpropanoids from Scrophularia buergeriana roots against CCl(4)-induced toxicity: action mechanism and structure-activity relationship. Planta medica. 2002 May; 68(5):407-11. doi: 10.1055/s-2002-32081. [PMID: 12058315]
  • A R Rechner, J P Spencer, G Kuhnle, U Hahn, C A Rice-Evans. Novel biomarkers of the metabolism of caffeic acid derivatives in vivo. Free radical biology & medicine. 2001 Jun; 30(11):1213-22. doi: 10.1016/s0891-5849(01)00506-8. [PMID: 11368919]
  • I M Liu, F L Hsu, C F Chen, J T Cheng. Antihyperglycemic action of isoferulic acid in streptozotocin-induced diabetic rats. British journal of pharmacology. 2000 Feb; 129(4):631-6. doi: 10.1038/sj.bjp.0703082. [PMID: 10683186]
  • I M Liu, T C Chi, F L Hsu, C F Chen, J T Cheng. Isoferulic acid as active principle from the rhizoma of Cimicifuga dahurica to lower plasma glucose in diabetic rats. Planta medica. 1999 Dec; 65(8):712-4. doi: 10.1055/s-1999-14048. [PMID: 10630111]
  • S Watanabe, S Sato, S Nagase, K Shimosato, T Saito. Polyamine levels in various tissues of rats treated with 3-hydroxy-4-methoxycinnamic acid and 3,4-dimethoxycinnamic acid. Anti-cancer drugs. 1996 Nov; 7(8):866-72. doi: 10.1097/00001813-199611000-00008. [PMID: 8991191]