4-O-Methylgallic acid (BioDeep_00000023558)
human metabolite Endogenous blood metabolite
代谢物信息卡片
化学式: C8H8O5 (184.0372)
中文名称: 5-羟基异香草酸
谱图信息:
最多检出来源 Homo sapiens(feces) 65.65%
分子结构信息
SMILES: COC1=C(C=C(C=C1O)C(=O)O)O
InChI: InChI=1S/C8H8O5/c1-13-7-5(9)2-4(8(11)12)3-6(7)10/h2-3,9-10H,1H3,(H,11,12)
描述信息
4-O-Methyl gallic acid (4-OMGA) has first been identified as a major methyl derivative of gallic acid in human plasma and urine. More recently, 4-O-methyl gallic acid (4-OMGA) has been found in urine during regular black tea ingestion and in plasma after moderate red wine consumption. PMID: 15527792. 4-O-methylgallic acid (4-OMGA), a major metabolite of gallic acid abundant in red wine. 4-OMGA inhibited the expression of intercellular adhesion molecule-1(ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1) in human umbilical vein endothelial cells (HUVECs) stimulated with tumor necrosis factor-alpha (TNF-alpha), resulting in the suppression of leukocyte adhesion to HUVECs (PMID: 17027748). 4-O-Methyl gallic acid has been found to be a metabolite of Beauveria and Pantoea (PMID: 17111140) (https://www.researchgate.net/publication/275561863_Microbial_Degradation_of_Bergenin_a_Phenolic_C-Glucoside).
4-O-Methyl gallic acid (4-OMGA) has first been identified as a major methyl derivative of gallic acid in human plasma and urine. More recently, 4-O-methyl gallic acid (4-OMGA) has been found in urine during regular black tea ingestion and in plasma after moderate red wine consumption. PMID: 15527792
同义名列表
13 个代谢物同义名
3,5-Dihydroxy-4-methoxy-benzoic acid; 3,5-Dihydroxy-4-methoxybenzoic acid; 4-Methoxy-3,5-dihydroxybenzoic acid; 3,5-Dihydroxy-4-methoxy-benzoate; 4-Methoxy-3,5-dihydroxybenzoate; 3,5-Dihydroxy-4-methoxybenzoate; 3,5-dihydroxy-p-anisic acid; 5-Hydroxyisovanillic acid; 4-O-Methylgallic acid; 4-Methoxygallic acid; 4-O-Methylgallate; 4-Methoxygallate; 4OMGA CPD
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:88738
- PubChem: 78016
- HMDB: HMDB0013198
- ChEMBL: CHEMBL118992
- foodb: FDB001960
- chemspider: 70398
- CAS: 4319-02-2
- PMhub: MS000111759
- RefMet: 4-O-Methylgallic acid
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
1 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
5 个相关的物种来源信息
- 210348 - Brucea javanica: 10.1248/CPB.55.804
- 1679397 - Calophyllum polyanthum: 10.1021/NP0499158
- 9606 - Homo sapiens: -
- 29780 - Mangifera indica: 10.1016/0031-9422(88)80189-4
- 298662 - Rhus glabra: 10.1016/0378-8741(94)90102-3
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。
亚细胞结构定位 | 关联基因列表 |
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文献列表
- Jae Sik Yu, Minji Park, Changhyun Pang, Luay Rashan, Won Hee Jung, Ki Hyun Kim. Antifungal Phenols from Woodfordia uniflora Collected in Oman.
Journal of natural products.
2020 07; 83(7):2261-2268. doi:
10.1021/acs.jnatprod.0c00395
. [PMID: 32639158] - Ryan C Barnes, Hyemee Kim, Susanne U Mertens-Talcott, Stephen T Talcott. Improved recovery of galloyl metabolites from mango (Mangifera indica L.) in human plasma using protein precipitation with sodium dodecyl sulfate and methanol.
Food research international (Ottawa, Ont.).
2020 03; 129(?):108812. doi:
10.1016/j.foodres.2019.108812
. [PMID: 32036936] - Chun-Ling Zhu. [Chemical constituents of n-BuOH extract from Phyllanthus matsumurae].
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials.
2014 Apr; 37(4):608-10. doi:
. [PMID: 25345134]
- Waranya Lakornwong, Kwanjai Kanokmedhakul, Somdej Kanokmedhakul. Chemical constituents from the roots of Leea thorelii Gagnep.
Natural product research.
2014; 28(13):1015-7. doi:
10.1080/14786419.2014.891117
. [PMID: 24784484] - Xiao-Xia Yan, Zheng-Fen Liang, Mao-Yuan Wang, Jian-Rong Wang, Zhu-Nian Wang. [Study on the chemical constituents in the fruit of Harrisonia perforata].
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials.
2013 Feb; 36(2):223-5. doi:
. [PMID: 23901646]
- Kanti Bhooshan Pandey, Syed Ibrahim Rizvi. Plant polyphenols as dietary antioxidants in human health and disease.
Oxidative medicine and cellular longevity.
2009 Nov; 2(5):270-8. doi:
10.4161/oxim.2.5.9498
. [PMID: 20716914] - Akiko Nozaki, Toshikiro Kimura, Hideyuki Ito, Tsutomu Hatano. Interaction of polyphenolic metabolites with human serum albumin: a circular dichroism study.
Chemical & pharmaceutical bulletin.
2009 Sep; 57(9):1019-23. doi:
10.1248/cpb.57.1019
. [PMID: 19721270] - L I Mennen, D Sapinho, H Ito, P Galan, S Hercberg, A Scalbert. Urinary excretion of 13 dietary flavonoids and phenolic acids in free-living healthy subjects - variability and possible use as biomarkers of polyphenol intake.
European journal of clinical nutrition.
2008 Apr; 62(4):519-25. doi:
10.1038/sj.ejcn.1602744
. [PMID: 17426744] - Xiang-zhong Huang, Li-xiang Tan, Kun Gu, Cong Li. [Studies on chemical constituentsfrom leaves of Acer truncatum].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2007 Aug; 32(15):1544-1546, 1604. doi:
"
. [PMID: 17972585] - Jonathan M Hodgson, Ian B Puddey, Frank M van Bockxmeer, Valerie Burke. Acute effects of tea on fasting and non-fasting plasma total homocysteine concentrations in human subjects.
The British journal of nutrition.
2007 May; 97(5):842-6. doi:
10.1017/s0007114507669190
. [PMID: 17408524] - Louise I Mennen, David Sapinho, Hideyuki Ito, Sandrine Bertrais, Pilar Galan, Serge Hercberg, Augustin Scalbert. Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods.
The British journal of nutrition.
2006 Jul; 96(1):191-8. doi:
10.1079/bjn20061808
. [PMID: 16870009] - Yerra Koteswara Rao, Shih-Hua Fang, Yew-Min Tzeng. Anti-inflammatory activities of constituents isolated from Phyllanthus polyphyllus.
Journal of ethnopharmacology.
2006 Jan; 103(2):181-6. doi:
10.1016/j.jep.2005.07.021
. [PMID: 16169167] - Jonathan M Hodgson, Amanda Devine, Ian B Puddey, John Beilby, Richard L Prince. Drinking tea is associated with lower plasma total homocysteine in older women.
Asia Pacific journal of clinical nutrition.
2006; 15(2):253-8. doi:
NULL
. [PMID: 16672212] - Jonathan M Hodgson, Ian B Puddey, Valerie Burke, Kevin D Croft. Is reversal of endothelial dysfunction by tea related to flavonoid metabolism?.
The British journal of nutrition.
2006 Jan; 95(1):14-7. doi:
10.1079/bjn20051621
. [PMID: 16441912] - Ki Suk Jeon, Hee-Jun Na, Young-Myeong Kim, Ho Jeong Kwon. Antiangiogenic activity of 4-O-methylgallic acid from Canavalia gladiata, a dietary legume.
Biochemical and biophysical research communications.
2005 May; 330(4):1268-74. doi:
10.1016/j.bbrc.2005.03.109
. [PMID: 15823580] - Natalie C Ward, Kevin D Croft, Ian B Puddey, Jonathan M Hodgson. Supplementation with grape seed polyphenols results in increased urinary excretion of 3-hydroxyphenylpropionic Acid, an important metabolite of proanthocyanidins in humans.
Journal of agricultural and food chemistry.
2004 Aug; 52(17):5545-9. doi:
10.1021/jf049404r
. [PMID: 15315398] - 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] - Jonathan M Hodgson, Amanda Devine, Ian B Puddey, Shin Yee Chan, Lawrence J Beilin, Richard L Prince. Tea intake is inversely related to blood pressure in older women.
The Journal of nutrition.
2003 Sep; 133(9):2883-6. doi:
10.1093/jn/133.9.2883
. [PMID: 12949382] - Jonathan M Hodgson, Valerie Burke, Lawrence J Beilin, Kevin D Croft, Ian B Puddey. Can black tea influence plasma total homocysteine concentrations?.
The American journal of clinical nutrition.
2003 Apr; 77(4):907-11. doi:
10.1093/ajcn/77.4.907
. [PMID: 12663290] - Yumiko Nakamura, Sumiko Tsuji, Yasuhide Tonogai. Method for analysis of tannic acid and its metabolites in biological samples: application to tannic acid metabolism in the rat.
Journal of agricultural and food chemistry.
2003 Jan; 51(1):331-9. doi:
10.1021/jf020847+
. [PMID: 12502429] - Jonathan M Hodgson, Ian B Puddey, Valerie Burke, Lawrence J Beilin, Trevor A Mori, Shin-Yee Chan. Acute effects of ingestion of black tea on postprandial platelet aggregation in human subjects.
The British journal of nutrition.
2002 Feb; 87(2):141-5. doi:
10.1079/bjn2001499
. [PMID: 11895166] - Jonathan M Hodgson, Kevin D Croft, Trevor A Mori, Valerie Burke, Lawrence J Beilin, Ian B Puddey. Regular ingestion of tea does not inhibit in vivo lipid peroxidation in humans.
The Journal of nutrition.
2002 Jan; 132(1):55-8. doi:
10.1093/jn/132.1.55
. [PMID: 11773508] - J M Hodgson, I B Puddey, T A Mori, V Burke, R I Baker, L J Beilin. Effects of regular ingestion of black tea on haemostasis and cell adhesion molecules in humans.
European journal of clinical nutrition.
2001 Oct; 55(10):881-6. doi:
10.1038/sj.ejcn.1601231
. [PMID: 11593350] - S Shahrzad, K Aoyagi, A Winter, A Koyama, I Bitsch. Pharmacokinetics of gallic acid and its relative bioavailability from tea in healthy humans.
The Journal of nutrition.
2001 Apr; 131(4):1207-10. doi:
10.1093/jn/131.4.1207
. [PMID: 11285327] - R Abu-Amsha Caccetta, V Burke, T A Mori, L J Beilin, I B Puddey, K D Croft. Red wine polyphenols, in the absence of alcohol, reduce lipid peroxidative stress in smoking subjects.
Free radical biology & medicine.
2001 Mar; 30(6):636-42. doi:
10.1016/s0891-5849(00)00497-4
. [PMID: 11295361] - T Yasuda, A Inaba, M Ohmori, T Endo, S Kubo, K Ohsawa. Urinary metabolites of gallic acid in rats and their radical-scavenging effects on 1,1-diphenyl-2-picrylhydrazyl radical.
Journal of natural products.
2000 Oct; 63(10):1444-6. doi:
10.1021/np0000421
. [PMID: 11076575] - J M Hodgson, I B Puddey, K D Croft, V Burke, T A Mori, R A Caccetta, L J Beilin. Acute effects of ingestion of black and green tea on lipoprotein oxidation.
The American journal of clinical nutrition.
2000 May; 71(5):1103-7. doi:
10.1093/ajcn/71.5.1103
. [PMID: 10799371] - S Shahrzad, I Bitsch. Determination of gallic acid and its metabolites in human plasma and urine by high-performance liquid chromatography.
Journal of chromatography. B, Biomedical sciences and applications.
1998 Jan; 705(1):87-95. doi:
10.1016/s0378-4347(97)00487-8
. [PMID: 9498674] - J Zhu, L J Filippich, J Ng. Rumen involvement in sheep tannic acid metabolism.
Veterinary and human toxicology.
1995 Oct; 37(5):436-40. doi:
. [PMID: 8592830]
- G Saxena, A R McCutcheon, S Farmer, G H Towers, R E Hancock. Antimicrobial constituents of Rhus glabra.
Journal of ethnopharmacology.
1994 Apr; 42(2):95-9. doi:
10.1016/0378-8741(94)90102-3
. [PMID: 8072309] - M M Ames, C D Selassie, L C Woodson, J A Van Loon, C Hansch, R M Weinshilboum. Thiopurine methyltransferase: structure-activity relationships for benzoic acid inhibitors and thiophenol substrates.
Journal of medicinal chemistry.
1986 Mar; 29(3):354-8. doi:
10.1021/jm00153a009
. [PMID: 3950915]