Isofraxidin (BioDeep_00000000102)

 

Secondary id: BioDeep_00000017233, BioDeep_00000398493

human metabolite PANOMIX_OTCML-2023 blood metabolite natural product


代谢物信息卡片


7-Hydroxy-6,8-dimethoxy-2H-1-benzopyran-2-one

化学式: C11H10O5 (222.0528)
中文名称: 异嗪皮啶
谱图信息: 最多检出来源 Viridiplantae(plant) 30.07%

分子结构信息

SMILES: COC1=C(C(=C2C(=C1)C=CC(=O)O2)OC)O
InChI: InChI=1S/C11H10O5/c1-14-7-5-6-3-4-8(12)16-10(6)11(15-2)9(7)13/h3-5,13H,1-2H3

描述信息

Isofraxidin, also known as 6,8-dimethoxy-7-hydroxycoumarin or 7-hydroxy-6,8-dimethoxy-2h-1-benzopyran-2-one, is a member of the class of compounds known as 7-hydroxycoumarins. 7-hydroxycoumarins are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Isofraxidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isofraxidin can be found in muskmelon, tarragon, and watermelon, which makes isofraxidin a potential biomarker for the consumption of these food products. Isofraxidin is a chemical compound found in a variety of plants including Eleutherococcus senticosus .
Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits MMP-7 expression and cell invasion of human hepatoma cells. Isofraxidin inhibits the phosphorylation of ERK1/2 in hepatoma cells[1]. Isofraxidin attenuates the expression of iNOS and COX-2, Isofraxidinalso inhibits TLR4/myeloid differentiation protein-2 (MD-2) complex formation[2].
Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits MMP-7 expression and cell invasion of human hepatoma cells. Isofraxidin inhibits the phosphorylation of ERK1/2 in hepatoma cells[1]. Isofraxidin attenuates the expression of iNOS and COX-2, Isofraxidinalso inhibits TLR4/myeloid differentiation protein-2 (MD-2) complex formation[2].

同义名列表

9 个代谢物同义名

7-Hydroxy-6,8-dimethoxy-2H-1-benzopyran-2-one; 7-hydroxy-6,8-dimethoxy-2H-chromen-2-one; 7-hydroxy-6,8-dimethoxychromen-2-one; 6,8-dimethoxy-7-hydroxy-coumarin; 6,8-dimethoxy-7-hydroxycoumarin; 7-hydroxy-6,8-dimethoxycoumarin; iso-fraxidin; Isofraxidin; Isofraxidin



数据库引用编号

17 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)

179 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 15 ANXA5, BCL2, CASP3, CASP8, EGFR, MAPK1, MAPK14, MAPK8, MITF, NLRP3, NOS2, PIK3CA, PTGS2, TLR4, TYR
Peripheral membrane protein 3 ANXA5, GORASP1, PTGS2
Endosome membrane 2 EGFR, TLR4
Endoplasmic reticulum membrane 3 BCL2, EGFR, PTGS2
Nucleus 11 BCL2, CASP3, CASP8, EGFR, JUND, MAPK1, MAPK14, MAPK8, MITF, NLRP3, NOS2
cytosol 11 ANXA5, BCL2, CASP3, CASP8, MAPK1, MAPK14, MAPK8, MITF, NLRP3, NOS2, PIK3CA
centrosome 1 MAPK1
nucleoplasm 8 CASP3, CASP8, JUND, MAPK1, MAPK14, MAPK8, MITF, NOS2
RNA polymerase II transcription regulator complex 1 JUND
Cell membrane 3 EGFR, TLR4, TNF
Cytoplasmic side 1 GORASP1
lamellipodium 2 CASP8, PIK3CA
ruffle membrane 1 EGFR
Early endosome membrane 1 EGFR
Golgi apparatus membrane 2 GORASP1, NLRP3
Synapse 2 MAPK1, MAPK8
cell junction 1 EGFR
cell surface 3 EGFR, TLR4, TNF
glutamatergic synapse 3 CASP3, EGFR, MAPK14
Golgi apparatus 2 GORASP1, MAPK1
Golgi membrane 3 EGFR, GORASP1, NLRP3
lysosomal membrane 1 MITF
neuronal cell body 2 CASP3, TNF
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 NLRP3, NOS2
Lysosome 1 TYR
endosome 1 EGFR
plasma membrane 6 EGFR, MAPK1, NOS2, PIK3CA, TLR4, TNF
Membrane 5 ANXA5, BCL2, EGFR, NLRP3, TLR4
apical plasma membrane 1 EGFR
axon 2 CCK, MAPK8
basolateral plasma membrane 1 EGFR
caveola 2 MAPK1, PTGS2
extracellular exosome 1 ANXA5
Lysosome membrane 1 MITF
endoplasmic reticulum 3 BCL2, NLRP3, PTGS2
extracellular space 4 CCK, EGFR, IL6, TNF
perinuclear region of cytoplasm 5 EGFR, NOS2, PIK3CA, TLR4, TYR
intercalated disc 1 PIK3CA
mitochondrion 5 BCL2, CASP8, MAPK1, MAPK14, NLRP3
protein-containing complex 5 BCL2, CASP8, EGFR, MITF, PTGS2
intracellular membrane-bounded organelle 1 TYR
Microsome membrane 1 PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 3 EGFR, TLR4, TYR
Secreted 3 CCK, IL6, NLRP3
extracellular region 7 ANXA5, CCK, IL6, MAPK1, MAPK14, NLRP3, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, CASP8
transcription regulator complex 1 JUND
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 MAPK1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, EGFR
external side of plasma membrane 3 ANXA5, TLR4, TNF
Melanosome membrane 1 TYR
Cytoplasm, P-body 1 NOS2
P-body 1 NOS2
Early endosome 2 MAPK1, TLR4
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cell projection, lamellipodium 1 CASP8
Cytoplasm, perinuclear region 1 NOS2
Membrane raft 2 EGFR, TNF
pore complex 1 BCL2
Cell junction, focal adhesion 1 MAPK1
Cytoplasm, cytoskeleton, spindle 1 MAPK1
focal adhesion 3 ANXA5, EGFR, MAPK1
spindle 1 MAPK1
cis-Golgi network 1 GORASP1
Peroxisome 1 NOS2
intracellular vesicle 1 EGFR
peroxisomal matrix 1 NOS2
collagen-containing extracellular matrix 1 ANXA5
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
Cell projection, ruffle 1 TLR4
Late endosome 1 MAPK1
ruffle 1 TLR4
receptor complex 2 EGFR, TLR4
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
chromatin 2 JUND, MITF
phagocytic cup 2 TLR4, TNF
mitotic spindle 1 MAPK1
cytoskeleton 2 CASP8, MAPK1
spindle pole 1 MAPK14
Endomembrane system 1 NLRP3
Membrane, caveola 1 MAPK1
microtubule organizing center 1 NLRP3
Melanosome 1 TYR
cell body 1 CASP8
myelin sheath 1 BCL2
pseudopodium 1 MAPK1
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
lipopolysaccharide receptor complex 1 TLR4
ficolin-1-rich granule lumen 2 MAPK1, MAPK14
secretory granule lumen 1 MAPK14
endoplasmic reticulum lumen 3 IL6, MAPK1, PTGS2
transcription repressor complex 1 JUND
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
azurophil granule lumen 1 MAPK1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
vesicle membrane 1 ANXA5
clathrin-coated endocytic vesicle membrane 1 EGFR
basal dendrite 1 MAPK8
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
transcription factor AP-1 complex 1 JUND
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
cortical cytoskeleton 1 NOS2
interleukin-6 receptor complex 1 IL6
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Yisen Huang, Xiangbo Chen, Xiaoqiang Liu, Chanchan Lin, Yubin Wang. The coumarin component isofraxidin targets the G-protein-coupled receptor S1PR1 to modulate IL-17 signaling and alleviate ulcerative colitis. International immunopharmacology. 2024 Apr; 131(?):111814. doi: 10.1016/j.intimp.2024.111814. [PMID: 38479159]
  • Shuang He, Ting Zhang, Yuan-Yi Wang, Wei Yuan, Li Li, Jin Li, Yue-Yan Yang, Dong-Ming Wu, Ying Xu. Isofraxidin attenuates dextran sulfate sodium-induced ulcerative colitis through inhibiting pyroptosis by upregulating Nrf2 and reducing reactive oxidative species. International immunopharmacology. 2024 Jan; 128(?):111570. doi: 10.1016/j.intimp.2024.111570. [PMID: 38280336]
  • Bingliang Lian, Jingwen Gu, Chen Zhang, Zhicong Zou, Meng Yu, Fanghong Li, Xiaoli Wu, Allan Zijian Zhao. Protective effects of isofraxidin against scopolamine-induced cognitive and memory impairments in mice involve modulation of the BDNF-CREB-ERK signaling pathway. Metabolic brain disease. 2022 12; 37(8):2751-2762. doi: 10.1007/s11011-022-00980-z. [PMID: 35921056]
  • Lei Jin, Zhen-Hua Ying, Chen-Huan Yu, Huan-Huan Zhang, Wen-Ying Yu, Xiao-Ning Wu. Isofraxidin ameliorated influenza viral inflammation in rodents via inhibiting platelet aggregation. International immunopharmacology. 2020 Jul; 84(?):106521. doi: 10.1016/j.intimp.2020.106521. [PMID: 32315950]
  • Mohammad Bagher Majnooni, Sajad Fakhri, Yalda Shokoohinia, Mahdi Mojarrab, Sara Kazemi-Afrakoti, Mohammad Hosein Farzaei. Isofraxidin: Synthesis, Biosynthesis, Isolation, Pharmacokinetic and Pharmacological Properties. Molecules (Basel, Switzerland). 2020 Apr; 25(9):. doi: 10.3390/molecules25092040. [PMID: 32349420]
  • Guofan Chen, Xiaozheng Song, Dongming Lin, Peng Xu. Isofraxidin Alleviates Myocardial Infarction Through NLRP3 Inflammasome Inhibition. Inflammation. 2020 Apr; 43(2):712-721. doi: 10.1007/s10753-019-01158-z. [PMID: 31916051]
  • Lu Jin, Michael Schmiech, Menna El Gaafary, Xinlei Zhang, Tatiana Syrovets, Thomas Simmet. A comparative study on root and bark extracts of Eleutherococcus senticosus and their effects on human macrophages. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Mar; 68(?):153181. doi: 10.1016/j.phymed.2020.153181. [PMID: 32065954]
  • Akram Taleghani, Seyed Ahmad Emami, Zahra Tayarani-Najaran. Artemisia: a promising plant for the treatment of cancer. Bioorganic & medicinal chemistry. 2020 01; 28(1):115180. doi: 10.1016/j.bmc.2019.115180. [PMID: 31784199]
  • Xiaoqiang Su, Bo Liu, Futai Gong, Jichao Yin, Qing Sun, Ye Gao, Zeyi Lv, Xiangyang Wang. Isofraxidin attenuates IL-1β-induced inflammatory response in human nucleus pulposus cells. Journal of cellular biochemistry. 2019 08; 120(8):13302-13309. doi: 10.1002/jcb.28604. [PMID: 30891836]
  • Jialei Jin, Xingfang Yu, Zhichao Hu, Shangkun Tang, Xinyang Zhong, Jianchen Xu, Ping Shang, Yixing Huang, Haixiao Liu. Isofraxidin targets the TLR4/MD-2 axis to prevent osteoarthritis development. Food & function. 2018 Nov; 9(11):5641-5652. doi: 10.1039/c8fo01445k. [PMID: 30299441]
  • Jian Lin, Xiaobin Li, Weihui Qi, Yingzhao Yan, Kai Chen, Xinghe Xue, Xinxian Xu, Zhenhua Feng, Xiaoyun Pan. Isofraxidin inhibits interleukin-1β induced inflammatory response in human osteoarthritis chondrocytes. International immunopharmacology. 2018 Nov; 64(?):238-245. doi: 10.1016/j.intimp.2018.09.003. [PMID: 30205322]
  • Jian Li, Xiaofei Li, Zhike Li, Lu Zhang, Yonggang Liu, Hong Ding, Shanye Yin. Isofraxidin, a coumarin component improves high-fat diet induced hepatic lipid homeostasis disorder and macrophage inflammation in mice. Food & function. 2017 Aug; 8(8):2886-2896. doi: 10.1039/c7fo00290d. [PMID: 28737815]
  • Bin Zhang, Jianguo Chen, Qichuan Jiang, Xuefeng Wang, Yan Lu, Liang Gong, Dong Chen. Simultaneous determination of three active components in rat plasma by UPLC-MS/MS: Application to pharmacokinetic study after oral administration of Herba Sarcandrae extract. Biomedical chromatography : BMC. 2017 Apr; 31(4):. doi: 10.1002/bmc.3834. [PMID: 27591379]
  • Fanxing Meng, Yan Li, Guiyuan He, Guangbo Ge, Shumin Liu. Identification of human UDP-glucuronosyltransferase isoforms involved in the isofraxidin glucuronidation and assessment of the species differences of the reaction. Fitoterapia. 2017 Mar; 117(?):118-125. doi: 10.1016/j.fitote.2016.11.017. [PMID: 27915055]
  • Kelly Marie Steinberg, Samon Shrestha, Noura S Dosoky, Lianet Monzote, Abel Piñón, William A Haber, William N Setzer. Cytotoxic and Antileishmanial Components from the Bark Extract of Ruyschiaphylladenia from Monteverde, Costa Rica. Natural product communications. 2017 Jan; 12(1):1-2. doi: ". [PMID: 30549810]
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  • Xiaofeng Niu, Yu Wang, Weifeng Li, Qingli Mu, Huani Li, Huan Yao, Hailin Zhang. Protective effects of Isofraxidin against lipopolysaccharide-induced acute lung injury in mice. International immunopharmacology. 2015 Feb; 24(2):432-439. doi: 10.1016/j.intimp.2014.12.041. [PMID: 25596039]
  • Hui-Xia Fan, Zhi-Peng Deng, Hao Zhong, Xiao-Ting Xu, Qing-Qiang Yao. [Comparative pharmacokinetics of syringin, eleutheroside E and isofraxidin in rat plasma after intravenous administration of each monomer and Ciwujia injection]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 May; 39(10):1921-7. doi: . [PMID: 25282907]
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  • Xiaofeng Niu, Wei Xing, Weifeng Li, Ting Fan, Hua Hu, Yongmei Li. Isofraxidin exhibited anti-inflammatory effects in vivo and inhibited TNF-α production in LPS-induced mouse peritoneal macrophages in vitro via the MAPK pathway. International immunopharmacology. 2012 Oct; 14(2):164-71. doi: 10.1016/j.intimp.2012.06.022. [PMID: 22800929]
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