Avenanthramide C (BioDeep_00000021091)

 

Secondary id: BioDeep_00000622019

human metabolite blood metabolite


代谢物信息卡片


2-{[(2E)-3-(3,4-dihydroxyphenyl)-1-hydroxyprop-2-en-1-ylidene]amino}-5-hydroxybenzoate

化学式: C16H13NO6 (315.0742838)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(lipidsearch) 16%

分子结构信息

SMILES: C1=CC(=C(C=C1C=CC(=O)NC2=C(C=C(C=C2)O)C(=O)O)O)O
InChI: InChI=1S/C16H13NO6/c18-10-3-4-12(11(8-10)16(22)23)17-15(21)6-2-9-1-5-13(19)14(20)7-9/h1-8,18-20H,(H,17,21)(H,22,23)/b6-2+

描述信息

Avenanthramide c is a member of the class of compounds known as avenanthramides. Avenanthramides are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferulic, caffeic, or p-coumaric acid) and anthranilic acid. Avenanthramide c is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Avenanthramide c can be found in cereals and cereal products, which makes avenanthramide c a potential biomarker for the consumption of this food product.
N-(3,4-Dihydroxycinnamoyl)-2-amino-5-hydroxybenzoic acid is found in cereals and cereal products. N-(3,4-Dihydroxycinnamoyl)-2-amino-5-hydroxybenzoic acid is isolated from oats (Avena sativa).

同义名列表

9 个代谢物同义名

2-{[(2E)-3-(3,4-dihydroxyphenyl)-1-hydroxyprop-2-en-1-ylidene]amino}-5-hydroxybenzoate; 2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid; N-(3,4-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid; N-(3,4-dihydroxycinnamoyl)-5-hydroxyanthranilic acid; Avenanthramide 2C; Avenanthramide-2C; Avenanthramide C; Avenanthramide-c; Avenanthramide



数据库引用编号

9 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)

3 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

  • Xi Xie, Miaoyan Lin, Gengsheng Xiao, Huifan Liu, Feng Wang, Dongjie Liu, Lukai Ma, Qin Wang, Zhiyong Li. Phenolic amides (avenanthramides) in oats - an update review. Bioengineered. 2024 12; 15(1):2305029. doi: 10.1080/21655979.2024.2305029. [PMID: 38258524]
  • Michal Jágr, Andreas Hofinger-Horvath, Peter Ergang, Petra Hlásná Čepková, Regine Schönlechner, Eleonora Charlotte Pichler, Stefano D Amico, Heinrich Grausgruber, Karla Vagnerová, Václav Dvořáček. Comprehensive study of the effect of oat grain germination on the content of avenanthramides. Food chemistry. 2024 Mar; 437(Pt 1):137807. doi: 10.1016/j.foodchem.2023.137807. [PMID: 37871428]
  • Lorenza Trabalzini, Jasmine Ercoli, Alfonso Trezza, Irene Schiavo, Giulia Macrì, Andrea Moglia, Ottavia Spiga, Federica Finetti. Pharmacological and In Silico Analysis of Oat Avenanthramides as EGFR Inhibitors: Effects on EGF-Induced Lung Cancer Cell Growth and Migration. International journal of molecular sciences. 2022 Aug; 23(15):. doi: 10.3390/ijms23158534. [PMID: 35955669]
  • Alphonse Umugire, Youngmi Choi, Sungsu Lee, Hyong-Ho Cho. Efficiency of antioxidant Avenanthramide-C on high-dose methotrexate-induced ototoxicity in mice. PloS one. 2022; 17(3):e0266108. doi: 10.1371/journal.pone.0266108. [PMID: 35353852]
  • Yu-Young Lee, Ming Wang, Yurim Son, Eun-Ju Yang, Moon-Seok Kang, Hyun-Joo Kim, Hyung-Seok Kim, Jihoon Jo. Oat Extract Avenanthramide-C Reverses Hippocampal Long-Term Potentiation Decline in Tg2576 Mice. Molecules (Basel, Switzerland). 2021 Oct; 26(20):. doi: 10.3390/molecules26206105. [PMID: 34684684]
  • Thanh-Tam Tran, Won-Hyun Song, Gyuseok Lee, Hyung Seok Kim, Daeho Park, Yun Hyun Huh, Je-Hwang Ryu. Avenanthramide C as a novel candidate to alleviate osteoarthritic pathogenesis. BMB reports. 2021 Oct; 54(10):528-533. doi: ". [PMID: 34488936]
  • Yanan Hou, Shoujiao Peng, Zilong Song, Feifei Bai, Xinming Li, Jianguo Fang. Oat polyphenol avenanthramide-2c confers protection from oxidative stress by regulating the Nrf2-ARE signaling pathway in PC12 cells. Archives of biochemistry and biophysics. 2021 07; 706(?):108857. doi: 10.1016/j.abb.2021.108857. [PMID: 33781769]
  • Aparicio-Fernández Xochitl, Reynoso-Camacho Rosalía, Ramos-Gómez Minerva, Magdalena Mendoza-Sánchez, Ofelia Mora, Iza F Pérez-Ramírez. Polyphenols and avenanthramides extracted from oat (Avena sativa L.) grains and sprouts modulate genes involved in glucose and lipid metabolisms in 3T3 L1 adipocytes. Journal of food biochemistry. 2021 06; 45(6):e13738. doi: 10.1111/jfbc.13738. [PMID: 33899247]
  • Sara C Campbell. Faecalibacterium prausnitzii Abundance in Mouse and Human Gut Can Predict Metabolism of Oat Avenanthramides. The Journal of nutrition. 2021 Jun; 151(6):1369-1370. doi: 10.1093/jn/nxab086. [PMID: 33847340]
  • Soyoung Kim, Tae Hee Kim, Yu Jeong Jeong, Su Hyun Park, Sung Chul Park, Jiyoung Lee, Kwang Yeol Yang, Jae Cheol Jeong, Cha Young Kim. Synergistic Effect of Methyl Jasmonate and Abscisic Acid Co-Treatment on Avenanthramide Production in Germinating Oats. International journal of molecular sciences. 2021 Apr; 22(9):. doi: 10.3390/ijms22094779. [PMID: 33946373]
  • Keshun Liu, Mitchell L Wise. Distributions of nutrients and avenanthramides within oat grain and effects on pearled kernel composition. Food chemistry. 2021 Jan; 336(?):127668. doi: 10.1016/j.foodchem.2020.127668. [PMID: 32758805]
  • Maria Guadalupe Quiroz Vazquez, Dvorak Montiel Condado, Brenda Gonzalez Hernandez, Azucena Gonzalez-Horta. Avenanthramide-C prevents amyloid formation of bovine serum albumin. Biophysical chemistry. 2020 08; 263(?):106391. doi: 10.1016/j.bpc.2020.106391. [PMID: 32413599]
  • Tianou Zhang, Tong Zhao, Yuzi Zhang, Tao Liu, Gilles Gagnon, Jacqueline Ebrahim, Jodee Johnson, Yi-Fang Chu, Li Li Ji. Avenanthramide supplementation reduces eccentric exercise-induced inflammation in young men and women. Journal of the International Society of Sports Nutrition. 2020 Jul; 17(1):41. doi: 10.1186/s12970-020-00368-3. [PMID: 32711519]
  • Michal Jágr, Václav Dvořáček, Petra Hlásná Čepková, Jana Doležalová. Comprehensive analysis of oat avenanthramides using hybrid quadrupole-Orbitrap mass spectrometry: Possible detection of new compounds. Rapid communications in mass spectrometry : RCM. 2020 May; 34(10):e8718. doi: 10.1002/rcm.8718. [PMID: 31896159]
  • Chao Chen, Ting Li, Zhengxing Chen, Li Wang, Xiaohu Luo. Absorption Rates and Mechanisms of Avenanthramides in a Caco-2 Cell Model and Their Antioxidant Activity during Absorption. Journal of agricultural and food chemistry. 2020 Feb; 68(8):2347-2356. doi: 10.1021/acs.jafc.9b06576. [PMID: 32026690]
  • Hima Dhakal, Eun-Ju Yang, Soyoung Lee, Min-Jong Kim, Moon-Chang Baek, Byungheon Lee, Pil-Hoon Park, Taeg Kyu Kwon, Dongwoo Khang, Kyung-Sik Song, Sang-Hyun Kim. Avenanthramide C from germinated oats exhibits anti-allergic inflammatory effects in mast cells. Scientific reports. 2019 05; 9(1):6884. doi: 10.1038/s41598-019-43412-2. [PMID: 31053741]
  • Ji Hae Lee, Byoung-Kyu Lee, Hyoung-Ho Park, Byong Won Lee, Koan Sik Woo, Hyun-Joo Kim, Sang-Ik Han, Yu Young Lee. Oat germination and ultrafiltration process improves the polyphenol and avenanthramide contents with protective effect in oxidative-damaged HepG2 cells. Journal of food biochemistry. 2019 04; 43(4):e12799. doi: 10.1111/jfbc.12799. [PMID: 31353574]
  • Wouter J C de Bruijn, Sarah van Dinteren, Harry Gruppen, Jean-Paul Vincken. Mass spectrometric characterisation of avenanthramides and enhancing their production by germination of oat (Avena sativa). Food chemistry. 2019 Mar; 277(?):682-690. doi: 10.1016/j.foodchem.2018.11.013. [PMID: 30502203]
  • Maha A Aldubayan, Rehab M Elgharabawy, Amira S Ahmed, Ehab Tousson. Antineoplastic Activity and Curative Role of Avenanthramides against the Growth of Ehrlich Solid Tumors in Mice. Oxidative medicine and cellular longevity. 2019; 2019(?):5162687. doi: 10.1155/2019/5162687. [PMID: 30755785]
  • Wenbin Wu, Yao Tang, Junli Yang, Emmanuel Idehen, Shengmin Sang. Avenanthramide Aglycones and Glucosides in Oat Bran: Chemical Profile, Levels in Commercial Oat Products, and Cytotoxicity to Human Colon Cancer Cells. Journal of agricultural and food chemistry. 2018 Aug; 66(30):8005-8014. doi: 10.1021/acs.jafc.8b02767. [PMID: 29985603]
  • E S Scarpa, M Mari, E Antonini, F Palma, P Ninfali. Natural and synthetic avenanthramides activate caspases 2, 8, 3 and downregulate hTERT, MDR1 and COX-2 genes in CaCo-2 and Hep3B cancer cells. Food & function. 2018 May; 9(5):2913-2921. doi: 10.1039/c7fo01804e. [PMID: 29726862]
  • Jason Walsh, Jordan Haddock, Jeffrey B Blumberg, Diane L McKay, Xiaoyong Wei, Gregory Dolnikowski, C-Y Oliver Chen. Identification of methylated metabolites of oat avenanthramides in human plasma using UHPLC QToF-MS. International journal of food sciences and nutrition. 2018 May; 69(3):377-383. doi: 10.1080/09637486.2017.1371116. [PMID: 28889763]
  • Michael Thomas, Sharon Kim, Weimin Guo, F William Collins, Mitchell L Wise, Mohsen Meydani. High Levels of Avenanthramides in Oat-Based Diet Further Suppress High Fat Diet-Induced Atherosclerosis in Ldlr-/- Mice. Journal of agricultural and food chemistry. 2018 Jan; 66(2):498-504. doi: 10.1021/acs.jafc.7b04860. [PMID: 29298067]
  • Manuel Y Schär, Giulia Corona, Gulten Soycan, Clemence Dine, Angelika Kristek, Sarah N S Alsharif, Volker Behrends, Alison Lovegrove, Peter R Shewry, Jeremy P E Spencer. Excretion of Avenanthramides, Phenolic Acids and their Major Metabolites Following Intake of Oat Bran. Molecular nutrition & food research. 2018 01; 62(2):. doi: 10.1002/mnfr.201700499. [PMID: 29024323]
  • Andrea Perrelli, Luca Goitre, Anna Maria Salzano, Andrea Moglia, Andrea Scaloni, Saverio Francesco Retta. Biological Activities, Health Benefits, and Therapeutic Properties of Avenanthramides: From Skin Protection to Prevention and Treatment of Cerebrovascular Diseases. Oxidative medicine and cellular longevity. 2018; 2018(?):6015351. doi: 10.1155/2018/6015351. [PMID: 30245775]
  • Gracia Montilla-Bascón, Corey D Broeckling, Owen A Hoekenga, Elena Prats, Mark Sorrells, Julio Isidro-Sánchez. Chromatographic Methods to Evaluate Nutritional Quality in Oat. Methods in molecular biology (Clifton, N.J.). 2017; 1536(?):115-125. doi: 10.1007/978-1-4939-6682-0_8. [PMID: 28132146]
  • Khaled M A Hassanein, Yasmin O El-Amir. Protective effects of thymoquinone and avenanthramides on titanium dioxide nanoparticles induced toxicity in Sprague-Dawley rats. Pathology, research and practice. 2017 Jan; 213(1):13-22. doi: 10.1016/j.prp.2016.08.002. [PMID: 27916297]
  • Tianou Zhang, Jing Shao, Yike Gao, Chi Chen, Dan Yao, Yi Fang Chu, Jodee Johnson, Chounghun Kang, Dongwook Yeo, Li Li Ji. Absorption and Elimination of Oat Avenanthramides in Humans after Acute Consumption of Oat Cookies. Oxidative medicine and cellular longevity. 2017; 2017(?):2056705. doi: 10.1155/2017/2056705. [PMID: 29430278]
  • Ryan T Koenig, Jonathan R Dickman, Choung-Hun Kang, Tianou Zhang, Yi-Fang Chu, Li Li Ji. Avenanthramide supplementation attenuates eccentric exercise-inflicted blood inflammatory markers in women. European journal of applied physiology. 2016 Jan; 116(1):67-76. doi: 10.1007/s00421-015-3244-3. [PMID: 26289619]
  • Junsheng Fu, Yingdong Zhu, Aaron Yerke, Mitchell L Wise, Jodee Johnson, YiFang Chu, Shengmin Sang. Oat avenanthramides induce heme oxygenase-1 expression via Nrf2-mediated signaling in HK-2 cells. Molecular nutrition & food research. 2015 Dec; 59(12):2471-9. doi: 10.1002/mnfr.201500250. [PMID: 26331632]
  • Chenfei Gao, Zhanguo Gao, Frank L Greenway, Jeffrey H Burton, William D Johnson, Michael J Keenan, Frederick M Enright, Roy J Martin, YiFang Chu, Jolene Zheng. Oat consumption reduced intestinal fat deposition and improved health span in Caenorhabditis elegans model. Nutrition research (New York, N.Y.). 2015 Sep; 35(9):834-43. doi: 10.1016/j.nutres.2015.06.007. [PMID: 26253816]
  • Pei Wang, Huadong Chen, Yingdong Zhu, Jennifer McBride, Junsheng Fu, Shengmin Sang. Oat avenanthramide-C (2c) is biotransformed by mice and the human microbiota into bioactive metabolites. The Journal of nutrition. 2015 Feb; 145(2):239-45. doi: 10.3945/jn.114.206508. [PMID: 25644343]
  • Andrea Moglia, Luca Goitre, Silvia Gianoglio, Eva Baldini, Eliana Trapani, Andrea Genre, Antonella Scattina, Giancarlo Dondo, Lorenza Trabalzini, Jules Beekwilder, Saverio Francesco Retta. Evaluation of the bioactive properties of avenanthramide analogs produced in recombinant yeast. BioFactors (Oxford, England). 2015 Jan; 41(1):15-27. doi: 10.1002/biof.1197. [PMID: 25639351]
  • Jun Yang, Boxin Ou, Mitchell L Wise, YiFang Chu. In vitro total antioxidant capacity and anti-inflammatory activity of three common oat-derived avenanthramides. Food chemistry. 2014 Oct; 160(?):338-45. doi: 10.1016/j.foodchem.2014.03.059. [PMID: 24799247]
  • D Pin, M Bekrich, O Fantini, G Noel, E Vidémont. An emulsion restores the skin barrier by decreasing the skin pH and inflammation in a canine experimental model. Journal of comparative pathology. 2014 Aug; 151(2-3):244-54. doi: 10.1016/j.jcpa.2014.04.009. [PMID: 24975893]
  • Ryan Koenig, Jonathan R Dickman, Chounghun Kang, Tianou Zhang, Yi-Fang Chu, Li Li Ji. Avenanthramide supplementation attenuates exercise-induced inflammation in postmenopausal women. Nutrition journal. 2014 Mar; 13(?):21. doi: 10.1186/1475-2891-13-21. [PMID: 24645793]
  • Mitchell L Wise. Effect of chemical systemic acquired resistance elicitors on avenanthramide biosynthesis in oat (Avena sativa). Journal of agricultural and food chemistry. 2011 Jul; 59(13):7028-38. doi: 10.1021/jf2008869. [PMID: 21598950]
  • Ryan T Koenig, Jonathan R Dickman, Mitchell L Wise, Li Li Ji. Avenanthramides are bioavailable and accumulate in hepatic, cardiac, and skeletal muscle tissue following oral gavage in rats. Journal of agricultural and food chemistry. 2011 Jun; 59(12):6438-43. doi: 10.1021/jf2002427. [PMID: 21417395]
  • Yi Ren, Xiushi Yang, Xiwu Niu, Sen Liu, Guixing Ren. Chemical characterization of the avenanthramide-rich extract from oat and its effect on D-galactose-induced oxidative stress in mice. Journal of agricultural and food chemistry. 2011 Jan; 59(1):206-11. doi: 10.1021/jf103938e. [PMID: 21141964]
  • Weimin Guo, Lin Nie, Dayong Wu, Mitchell L Wise, F William Collins, Simin Nikbin Meydani, Mohsen Meydani. Avenanthramides inhibit proliferation of human colon cancer cell lines in vitro. Nutrition and cancer. 2010; 62(8):1007-16. doi: 10.1080/01635581.2010.492090. [PMID: 21058188]
  • D C Doehlert, S Simsek, M L Wise. The green oat story: possible mechanisms of green color formation in oat products during cooking. Journal of food science. 2009 Aug; 74(6):S226-31. doi: 10.1111/j.1750-3841.2009.01190.x. [PMID: 19723227]
  • Yoshihiro Izumi, Shin'ichiro Kajiyama, Ryosuke Nakamura, Atsushi Ishihara, Atsushi Okazawa, Eiichiro Fukusaki, Yasuo Kanematsu, Akio Kobayashi. High-resolution spatial and temporal analysis of phytoalexin production in oats. Planta. 2009 Mar; 229(4):931-43. doi: 10.1007/s00425-008-0887-x. [PMID: 19148672]
  • C-Y Oliver Chen, Paul E Milbury, F William Collins, Jeffrey B Blumberg. Avenanthramides are bioavailable and have antioxidant activity in humans after acute consumption of an enriched mixture from oats. The Journal of nutrition. 2007 Jun; 137(6):1375-82. doi: 10.1093/jn/137.6.1375. [PMID: 17513394]
  • Lin Nie, Mitchell L Wise, David M Peterson, Mohsen Meydani. Avenanthramide, a polyphenol from oats, inhibits vascular smooth muscle cell proliferation and enhances nitric oxide production. Atherosclerosis. 2006 Jun; 186(2):260-6. doi: 10.1016/j.atherosclerosis.2005.07.027. [PMID: 16139284]