Fraxin (BioDeep_00000003801)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


InChI=1/C16H18O10/c1-23-7-4-6-2-3-9(18)25-14(6)15(11(7)20)26-16-13(22)12(21)10(19)8(5-17)24-16/h2-4,8,10,12-13,16-17,19-22H,5H2,1H3/t8-,10-,12+,13-,16+/m1/s

化学式: C16H18O10 (370.09)
中文名称: 秦皮苷, 秦皮甙, 白蜡树苷
谱图信息: 最多检出来源 Viridiplantae(plant) 23.52%

分子结构信息

SMILES: COC1=C(C(=C2C(=C1)C=CC(=O)O2)OC3C(C(C(C(O3)CO)O)O)O)O
InChI: InChI=1S/C16H18O10/c1-23-7-4-6-2-3-9(18)25-14(6)15(11(7)20)26-16-13(22)12(21)10(19)8(5-17)24-16/h2-4,8,10,12-13,16-17,19-22H,5H2,1H3/t8-,10-,12+,13-,16+/m1/s1

描述信息

Fraxin is a beta-D-glucoside that is fraxetin attached to a beta-D-glucopyranosyl group at position 8 via a glycosidic linkage. It is a natural product isolated from the leaves of Fraxinus excelsior and exhibits potent hepatoprotective effects in vitro and in vivo. It has a role as a plant metabolite, an anti-inflammatory agent and a hepatoprotective agent. It is a beta-D-glucoside, a hydroxycoumarin and an aromatic ether. It is functionally related to a fraxetin.
Fraxin is a natural product found in Acer nikoense, Prunus prostrata, and other organisms with data available.
A beta-D-glucoside that is fraxetin attached to a beta-D-glucopyranosyl group at position 8 via a glycosidic linkage. It is a natural product isolated from the leaves of Fraxinus excelsior and exhibits potent hepatoprotective effects in vitro and in vivo.
Origin: Plant, Coumarins
Fraxin isolated from Cortex Fraxini, is a glucoside of fraxetin and reported to exert potent anti-oxidative stress action[1], anti-inflammatory and antimetastatic properties. Fraxin shows its antioxidative effect through inhibition of cyclo AMP phosphodiesterase enzyme[2].
Fraxin isolated from Cortex Fraxini, is a glucoside of fraxetin and reported to exert potent anti-oxidative stress action[1], anti-inflammatory and antimetastatic properties. Fraxin shows its antioxidative effect through inhibition of cyclo AMP phosphodiesterase enzyme[2].

同义名列表

32 个代谢物同义名

InChI=1/C16H18O10/c1-23-7-4-6-2-3-9(18)25-14(6)15(11(7)20)26-16-13(22)12(21)10(19)8(5-17)24-16/h2-4,8,10,12-13,16-17,19-22H,5H2,1H3/t8-,10-,12+,13-,16+/m1/s; 7-Hydroxy-6-methoxy-8-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2H-chromen-2-one; 7-hydroxy-6-methoxy-8-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-2H-chromen-2-one; 7-hydroxy-6-methoxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-2-one; 7-hydroxy-6-methoxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one; 2H-1-Benzopyran-2-one, 8-(.beta.-D-glucopyranosyloxy)-7-hydroxy-6-methoxy-; 2H-1-Benzopyran-2-one, 8-(beta-D-glucopyranosyloxy)-7-hydroxy-6-methoxy-; 8-(beta-D-Glucopyranosyloxy)-7-hydroxy-6-methoxy-2H-1-benzopyran-2-one; 7-hydroxy-6-methoxy-2-oxo-2H-chromen-8-yl beta-D-glucopyranoside; METHYL3,3,3-TRIFLUORO-2-[2,2,2-TRIFLUORO-ACETYLIMINO]PROPIONATE; 7,8-DIHYDROXY-6-METHOXYCOUMARIN 8-.BETA.-D-GLUCOPYRANOSIDE; 8-(beta-d-glucopyranosyloxy)-7-hydroxy-6-methoxycoumarin; 7,8-Dihydroxy-6-methoxycoumarin-8-beta-D-glucoside; FRAXETIN 8-.BETA.-D-GLUCOPYRANOSIDE; fraxetin-8-O-beta-D-glucopyranoside; fraxetin-8-beta-D-glucopyranoside; fraxetin-8-O-beta-D-glucoside; Fraxin, analytical standard; CRSFLLTWRCYNNX-QBNNUVSCSA-N; Fraxetin-8-O-glucoside; FRAXETOL 8-GLUCOSIDE; UNII-V7M270Y072; MEGxp0_000484; ACon1_000325; FRAXIN [MI]; V7M270Y072; Fraxoside; FRAXINE; Fraxin; paviin; 7-hydroxy-6-methoxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one; Fraxin



数据库引用编号

50 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)

137 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。

亚细胞结构定位 关联基因列表
Cytoplasm 12 EGFR, IKBKB, KEAP1, MAPK14, MITF, NLRP3, PPARG, PTGS2, SOD1, SRC, TYR, TYRP1
Peripheral membrane protein 1 PTGS2
Endosome membrane 2 EGFR, TYRP1
Endoplasmic reticulum membrane 3 EGFR, HMOX1, PTGS2
Nucleus 11 EGFR, GABPA, HMOX1, IKBKB, KEAP1, MAPK14, MITF, NLRP3, PPARG, SOD1, SRC
cytosol 11 GPT, HMOX1, IKBKB, KEAP1, MAPK14, MITF, NLRP3, NRK, PPARG, SOD1, SRC
nucleoplasm 8 GABPA, HMOX1, KEAP1, MAPK14, MITF, PPARG, SOD1, SRC
RNA polymerase II transcription regulator complex 1 PPARG
Cell membrane 3 EGFR, SRC, TNF
Lipid-anchor 1 SRC
Cytoplasmic side 1 HMOX1
ruffle membrane 2 EGFR, SRC
Early endosome membrane 1 EGFR
Golgi apparatus membrane 1 NLRP3
cell junction 2 EGFR, SRC
cell surface 2 EGFR, TNF
glutamatergic synapse 3 EGFR, MAPK14, SRC
Golgi membrane 2 EGFR, NLRP3
lysosomal membrane 1 MITF
mitochondrial inner membrane 1 SRC
neuronal cell body 3 SOD1, SRC, TNF
Cytoplasm, cytosol 1 NLRP3
Lysosome 2 SRC, TYR
endosome 1 EGFR
plasma membrane 3 EGFR, SRC, TNF
Membrane 4 EGFR, HMOX1, NLRP3, NRK
apical plasma membrane 1 EGFR
basolateral plasma membrane 1 EGFR
caveola 2 PTGS2, SRC
extracellular exosome 3 GPT, SOD1, SRC
Lysosome membrane 1 MITF
endoplasmic reticulum 4 HMOX1, KEAP1, NLRP3, PTGS2
extracellular space 6 CXCL8, EGFR, HMOX1, IL6, SOD1, TNF
perinuclear region of cytoplasm 5 EGFR, HMOX1, PPARG, SRC, TYR
mitochondrion 4 MAPK14, NLRP3, SOD1, SRC
protein-containing complex 4 EGFR, MITF, PTGS2, SOD1
intracellular membrane-bounded organelle 2 PPARG, TYR
Microsome membrane 1 PTGS2
Single-pass type I membrane protein 3 EGFR, TYR, TYRP1
Secreted 3 CXCL8, IL6, NLRP3
extracellular region 7 CXCL8, DNAH9, IL6, MAPK14, NLRP3, SOD1, TNF
cytoplasmic side of plasma membrane 1 IKBKB
mitochondrial outer membrane 1 HMOX1
mitochondrial matrix 1 SOD1
centriolar satellite 1 KEAP1
motile cilium 1 DNAH9
nuclear membrane 1 EGFR
CD40 receptor complex 1 IKBKB
external side of plasma membrane 1 TNF
cytoplasmic vesicle 1 SOD1
axon cytoplasm 1 SOD1
Melanosome membrane 2 TYR, TYRP1
midbody 1 KEAP1
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cytoplasm, perinuclear region 1 SRC
Mitochondrion inner membrane 1 SRC
Membrane raft 4 EGFR, IKBKB, SRC, TNF
Cell junction, focal adhesion 1 SRC
Cytoplasm, cytoskeleton 1 SRC
focal adhesion 2 EGFR, SRC
microtubule 1 DNAH9
Peroxisome 1 SOD1
intracellular vesicle 2 EGFR, TYRP1
mitochondrial intermembrane space 1 SOD1
axoneme 1 DNAH9
nuclear speck 1 MAPK14
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
dendrite cytoplasm 1 SOD1
Late endosome 1 SRC
receptor complex 2 EGFR, PPARG
neuron projection 1 PTGS2
chromatin 3 GABPA, MITF, PPARG
phagocytic cup 1 TNF
podosome 1 SRC
spindle pole 1 MAPK14
actin filament 2 KEAP1, SRC
Cytoplasm, cytoskeleton, cilium axoneme 1 DNAH9
Cul3-RING ubiquitin ligase complex 1 KEAP1
serine/threonine protein kinase complex 1 IKBKB
Endomembrane system 1 NLRP3
microtubule organizing center 1 NLRP3
Melanosome 2 TYR, TYRP1
dendritic growth cone 1 SRC
basal plasma membrane 1 EGFR
synaptic membrane 2 EGFR, SRC
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
endoplasmic reticulum lumen 2 IL6, PTGS2
9+2 motile cilium 1 DNAH9
dynein complex 1 DNAH9
Single-pass type IV membrane protein 1 HMOX1
IkappaB kinase complex 1 IKBKB
clathrin-coated endocytic vesicle membrane 2 EGFR, TYRP1
postsynaptic specialization, intracellular component 1 SRC
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
inclusion body 1 KEAP1
interleukin-6 receptor complex 1 IL6
dendritic filopodium 1 SRC
outer dynein arm 1 DNAH9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
distal portion of axoneme 1 DNAH9


文献列表

  • Weifeng Li, Wenqi Li, JinJin Yu, Fang Liu, Lulu Zang, Xin Xiao, Jinmeng Zhao, Qing Yao, Xiaofeng Niu. Fraxin inhibits lipopolysaccharide-induced inflammatory cytokines and protects against endotoxic shock in mice. Fundamental & clinical pharmacology. 2020 Feb; 34(1):91-101. doi: 10.1111/fcp.12500. [PMID: 31325387]
  • Ömer Topdağı, Ayhan Tanyeli, Fazile Nur Ekinci Akdemir, Ersen Eraslan, Mustafa Can Güler, Selim Çomaklı. Preventive effects of fraxin on ischemia/reperfusion-induced acute kidney injury in rats. Life sciences. 2020 Feb; 242(?):117217. doi: 10.1016/j.lfs.2019.117217. [PMID: 31884094]
  • Chi-Na Zhao, Zong-Li Yao, Dan Yang, Jian Ke, Qing-Lai Wu, Jun-Kai Li, Xu-Dong Zhou. Chemical Constituents from Fraxinus hupehensis and Their Antifungal and Herbicidal Activities. Biomolecules. 2020 01; 10(1):. doi: 10.3390/biom10010074. [PMID: 31906487]
  • Xiaohong Ma, Xiangyong Liu, Jiali Feng, Dong Zhang, Lina Huang, Dongxiao Li, Liang Yin, Lan Li, Xiao-Zhi Wang. Fraxin Alleviates LPS-Induced ARDS by Downregulating Inflammatory Responses and Oxidative Damages and Reducing Pulmonary Vascular Permeability. Inflammation. 2019 Oct; 42(5):1901-1912. doi: 10.1007/s10753-019-01052-8. [PMID: 31273573]
  • Weifeng Li, Wenqi Li, Lulu Zang, Fang Liu, Qing Yao, Jinmeng Zhao, Wenbing Zhi, Xiaofeng Niu. Fraxin ameliorates lipopolysaccharide-induced acute lung injury in mice by inhibiting the NF-κB and NLRP3 signalling pathways. International immunopharmacology. 2019 Feb; 67(?):1-12. doi: 10.1016/j.intimp.2018.12.003. [PMID: 30530164]
  • Aleksandra Owczarek, Arkadiusz Kłys, Monika A Olszewska. A validated 1H qNMR method for direct and simultaneous quantification of esculin, fraxin and (-)-epicatechin in Hippocastani cortex. Talanta. 2019 Jan; 192(?):263-269. doi: 10.1016/j.talanta.2018.09.036. [PMID: 30348388]
  • Yuanli Zhou, Xuanguo Zhang, Chao Li, Xin Yuan, Lihua Han, Zheng Li, Xiaobin Tan, Jie Song, Gang Wang, Xiaobin Jia, Liang Feng, Xiting Qiao, Jiping Liu. Research on the pharmacodynamics and mechanism of Fraxini Cortex on hyperuricemia based on the regulation of URAT1 and GLUT9. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Oct; 106(?):434-442. doi: 10.1016/j.biopha.2018.06.163. [PMID: 29990831]
  • Zhibin Wang, Wenbo Zhu, Hua Liu, Gaosong Wu, Mengmeng Song, Bingyou Yang, Deqiang Yang, Qiuhong Wang, Haixue Kuang. Simultaneous Determination of Aesculin, Aesculetin, Fraxetin, Fraxin and Polydatin in Beagle Dog Plasma by UPLC-ESI-MS/MS and Its Application in a Pharmacokinetic Study after Oral Administration Extracts of Ledum palustre L. Molecules (Basel, Switzerland). 2018 Sep; 23(9):. doi: 10.3390/molecules23092285. [PMID: 30205426]
  • Xiaofeng Niu, Fang Liu, Weifeng Li, Wenbing Zhi, Qing Yao, Jinmeng Zhao, Guoxiang Yang, Xiumei Wang, Lin Qin, Zehong He. Hepatoprotective effect of fraxin against carbon tetrachloride-induced hepatotoxicity in vitro and in vivo through regulating hepatic antioxidant, inflammation response and the MAPK-NF-κB signaling pathway. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Nov; 95(?):1091-1102. doi: 10.1016/j.biopha.2017.09.029. [PMID: 28922728]
  • Bo Yoon Chang, Young Suk Jung, Chi-Su Yoon, Jun Seok Oh, Jae Heoi Hong, Youn-Chul Kim, Sung Yeon Kim. Fraxin Prevents Chemically Induced Hepatotoxicity by Reducing Oxidative Stress. Molecules (Basel, Switzerland). 2017 Apr; 22(4):. doi: 10.3390/molecules22040587. [PMID: 28383514]
  • Haidong Wang, Bingxin Xiao, Zhiqiang Hao, Zengxian Sun. Simultaneous determination of fraxin and its metabolite, fraxetin, in rat plasma by liquid chromatography-tandem mass spectrometry and its application in a pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 Apr; 1017-1018(?):70-74. doi: 10.1016/j.jchromb.2016.02.030. [PMID: 26945887]
  • Michael Knoblauch, Marc Vendrell, Erica de Leau, Andrea Paterlini, Kirsten Knox, Tim Ross-Elliot, Anke Reinders, Stephen A Brockman, John Ward, Karl Oparka. Multispectral phloem-mobile probes: properties and applications. Plant physiology. 2015 Apr; 167(4):1211-20. doi: 10.1104/pp.114.255414. [PMID: 25653316]
  • Minglan Yu, Ailing Sun, Yongqing Zhang, Renmin Liu. Purification of coumarin compounds from Cortex fraxinus by adsorption chromatography. Journal of chromatographic science. 2014 Oct; 52(9):1033-7. doi: 10.1093/chromsci/bmt153. [PMID: 24114664]
  • Rohan A Davis, Daniela Vullo, Alfonso Maresca, Claudiu T Supuran, Sally-Ann Poulsen. Natural product coumarins that inhibit human carbonic anhydrases. Bioorganic & medicinal chemistry. 2013 Mar; 21(6):1539-43. doi: 10.1016/j.bmc.2012.07.021. [PMID: 22892213]
  • Xian Ding, Bo Yin, Li Qian, Zhirui Zeng, Zeliang Yang, Huixian Li, Yongjun Lu, Shining Zhou. Screening for novel quorum-sensing inhibitors to interfere with the formation of Pseudomonas aeruginosa biofilm. Journal of medical microbiology. 2011 Dec; 60(Pt 12):1827-1834. doi: 10.1099/jmm.0.024166-0. [PMID: 21852522]
  • Weihong Feng, Zhimin Wang, Qiwei Zhang, Limei Liu, Jinyu Wang, Fei Yang. [Quantitative method for simultaneous assay of four coumarins with one marker in Fraxini Cortex]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Jul; 36(13):1782-9. doi: ". [PMID: 22032145]
  • Zhi-jing Ma, Zhi-juan Zhao. [Studies on chemical constituents from stem barks of Fraxinus paxiana]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Aug; 33(16):1990-3. doi: ". [PMID: 19086636]
  • Sheng Lin, Ming-tao Liu, Su-juan Wang, Shuai Li, Yong-chun Yang, Jian-gong Shi. [Coumarins from branch of Fraxinus sieboldiana and their antioxidative activity]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Jul; 33(14):1708-10. doi: ". [PMID: 18841773]
  • Takaaki Yasuda, Mai Fukui, Takahiro Nakazawa, Ayumi Hoshikawa, Keisuke Ohsawa. Metabolic fate of fraxin administered orally to rats. Journal of natural products. 2006 May; 69(5):755-7. doi: 10.1021/np0580412. [PMID: 16724835]
  • Wan Kyunn Whang, Hyung Soon Park, InHye Ham, Mihyun Oh, Hong Namkoong, Hyun Kee Kim, Dong Whi Hwang, Soo Young Hur, Tae Eung Kim, Yong Gyu Park, Jae Ryong Kim, Jin Woo Kim. Natural compounds,fraxin and chemicals structurally related to fraxin protect cells from oxidative stress. Experimental & molecular medicine. 2005 Oct; 37(5):436-46. doi: 10.1038/emm.2005.54. [PMID: 16264268]
  • Sheng-Jun Dai, Ruo-Yun Chen, Pei-Cheng Zhang, De-Quan Yu. A new compound from Rhododendren anthopogonosides maxim. Journal of Asian natural products research. 2005 Aug; 7(4):681-5. doi: 10.1080/1028602032000169541. [PMID: 16087645]
  • Hyoung Ja Kim, Yeon Gyu Yu, Hokoon Park, Yong Sup Lee. HIV gp41 binding phenolic components from Fraxinus sieboldiana var. angustata. Planta medica. 2002 Nov; 68(11):1034-6. doi: 10.1055/s-2002-35665. [PMID: 12451497]
  • P Poukens-Renwart, M Tits, J N Wauters, L Angenot. Reversed-phase HPTLC densitometric evaluation of fraxin in Fraxinus excelsior leaves. Journal of pharmaceutical and biomedical analysis. 1992 Oct; 10(10-12):1089-91. doi: 10.1016/0731-7085(91)80126-t. [PMID: 1298368]