Avicularin (BioDeep_00000230219)

 

Secondary id: BioDeep_00000018735

natural product PANOMIX_OTCML-2023


代谢物信息卡片


3-(((2S,3R,4R,5S)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

化学式: C20H18O11 (434.0849078)
中文名称: 扁蓄苷, 蓄苷
谱图信息: 最多检出来源 Viridiplantae(plant) 3.1%

分子结构信息

SMILES: c1(cc(c2c(c1)oc(c(c2=O)O[C@H]1[C@@H]([C@@H]([C@@H](O1)CO)O)O)c1ccc(c(c1)O)O)O)O
InChI: InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2

描述信息

Avicularin is a quercetin O-glycoside in which an alpha-L-arabinofuranosyl residue is attached at position 3 of quercetin via a glycosidic linkage. It is isolated particularly from Juglans regia and Foeniculum vulgare. It has a role as a hepatoprotective agent and a plant metabolite. It is a monosaccharide derivative, an alpha-L-arabinofuranoside, a tetrahydroxyflavone and a quercetin O-glycoside.
Avicularin is a natural product found in Saxifraga tricuspidata, Rhododendron mucronulatum, and other organisms with data available.
A quercetin O-glycoside in which an alpha-L-arabinofuranosyl residue is attached at position 3 of quercetin via a glycosidic linkage. It is isolated particularly from Juglans regia and Foeniculum vulgare.
Avicularin is an orally active flavonoid. Avicularin inhibits NF-κB (p65), COX-2 and PPAR-γ activities. Avicularin has anti-inflammatory, anti-infectious anti-allergic, anti-oxidant, hepatoprotective, and anti-tumor activities[1][3].
Avicularin is an orally active flavonoid. Avicularin inhibits NF-κB (p65), COX-2 and PPAR-γ activities. Avicularin has anti-inflammatory, anti-infectious anti-allergic, anti-oxidant, hepatoprotective, and anti-tumor activities[1][3].
Avicularin is an orally active flavonoid. Avicularin inhibits NF-κB (p65), COX-2 and PPAR-γ activities. Avicularin has anti-inflammatory, anti-infectious anti-allergic, anti-oxidant, hepatoprotective, and anti-tumor activities[1][3].
Avicularin is an orally active flavonoid. Avicularin inhibits NF-κB (p65), COX-2 and PPAR-γ activities. Avicularin has anti-inflammatory, anti-infectious anti-allergic, anti-oxidant, hepatoprotective, and anti-tumor activities[1][3].

同义名列表

27 个代谢物同义名

3-(((2S,3R,4R,5S)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one; 3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one; 3-(.ALPHA.-L-ARABINOFURANOSYLOXY)-2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4H-1-BENZOPYRAN-4-ONE; 4H-1-Benzopyran-4-one, 3-(alpha-L-arabinofuranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl alpha-L-arabinofuranoside; QUERCETIN 3-O-.ALPHA.-L-ARABINOFURANOSIDE; Quercetin 3-O-alpha-L-arabinopyranoside; Quercetin 3-alpha-L-arabinofuranoside; quercetin-3-o-alpha-l-arabinoside; Avicularin, analytical standard; UNII-TN38NQ38BQ; Avicularoside; Avicularine; Fenicularin; TN38NQ38BQ; Guaiaverin; Avicularin; 3-[[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)-2-tetrahydrofuranyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-chromenone; 3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one; 3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one; 3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chromone; 158560-11-3; 572-30-5; Quercetin-3-O-alpha-arabinofuranoside; Quercetin-3-O-arabinofuranoside; 3- (alpha-L-Arabinofuranosyloxy) -2- (3,4-dihydroxyphenyl) -5,7-dihydroxy-4H-1-benzopyran-4-one; Quercetin 3-O-alpha-L-arabinofuranoside



数据库引用编号

41 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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

  • Zhentao Zhang, Guodong Lv, Liang Du. Avicularin Reduces the Expression of Mediators of Inflammation and Oxidative Stress in Bradykinin-Treated MG-63 Human Osteoblastic Osteosarcoma Cells. Medical science monitor : international medical journal of experimental and clinical research. 2020 May; 26(?):e921957. doi: 10.12659/msm.921957. [PMID: 32463805]
  • Xiaoai Zhu, Zhirou Qiu, Wen Ouyang, Jianyin Miao, Ping Xiong, Duobin Mao, Konglong Feng, Minxiong Li, Minna Luo, Hang Xiao, Yong Cao. Hepatic transcriptome and proteome analyses provide new insights into the regulator mechanism of dietary avicularin in diabetic mice. Food research international (Ottawa, Ont.). 2019 11; 125(?):108570. doi: 10.1016/j.foodres.2019.108570. [PMID: 31554135]
  • Zhimin Wang, Fang Li, Yuan Quan, Junye Shen. Avicularin ameliorates human hepatocellular carcinoma via the regulation of NF‑κB/COX‑2/PPAR‑γ activities. Molecular medicine reports. 2019 Jun; 19(6):5417-5423. doi: 10.3892/mmr.2019.10198. [PMID: 31059053]
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  • Sun Haeng Park, Seol Jang, Eunjung Son, Si Woo Lee, Sun Dong Park, Yoon-Young Sung, Ho Kyoung Kim. Polygonum aviculare L. extract reduces fatigue by inhibiting neuroinflammation in restraint-stressed mice. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Mar; 42(?):180-189. doi: 10.1016/j.phymed.2018.03.042. [PMID: 29655685]
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  • Xiao-He Feng, Zi-Hao Wang, Da-Li Meng, Xian Li. Cytotoxic and antioxidant constituents from the leaves of Psidium guajava. Bioorganic & medicinal chemistry letters. 2015; 25(10):2193-8. doi: 10.1016/j.bmcl.2015.03.058. [PMID: 25862199]
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  • Wei-Min Zhang, Rui-Fang Li, Ming Sun, Da-Ming Hu, Jian-Fei Qiu, Yun-Hao Yan. UPLC-MS/MS method for determination of avicularin in rat plasma and its application to a pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Aug; 965(?):107-11. doi: 10.1016/j.jchromb.2014.06.015. [PMID: 25010713]
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  • Ko Fujimori, Makio Shibano. Avicularin, a plant flavonoid, suppresses lipid accumulation through repression of C/EBPα-activated GLUT4-mediated glucose uptake in 3T3-L1 cells. Journal of agricultural and food chemistry. 2013 May; 61(21):5139-47. doi: 10.1021/jf401154c. [PMID: 23647459]
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