Isofraxidin (BioDeep_00000000102)

 

Secondary id: BioDeep_00000017233, BioDeep_00000398493

human metabolite PANOMIX_OTCML-2023 blood metabolite Volatile Flavor Compounds natural product


代谢物信息卡片


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

化学式: C11H10O5 (222.052821)
中文名称: 异嗪皮啶
谱图信息: 最多检出来源 Viridiplantae(plant) 11.92%

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。



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]
  • B Zhou, S-Z Liu, M-J Li, Z-H Chen, P Wang, D Cheng. Study on quality standards for Chimonanthus nitens. Genetics and molecular research : GMR. 2016 Aug; 15(3):. doi: 10.4238/gmr.15038984. [PMID: 27706658]
  • Ting Li, Kelsey Ferns, Zi-Qiao Yan, Si-Yuan Yin, Jun-Jie Kou, Dongsheng Li, Zheng Zeng, Lin Yin, Xiaoyu Wang, Hong-Xia Bao, Yu-Jie Zhou, Qing-Hai Li, Zhan-Yi Zhao, Huidi Liu, Shu-Lin Liu. Acanthopanax senticosus: Photochemistry and Anticancer Potential. The American journal of Chinese medicine. 2016; 44(8):1543-1558. doi: 10.1142/s0192415x16500865. [PMID: 27852123]
  • Hye Mi Kim, Su Jung Kim, Ha-Yeong Kim, Byeol Ryu, Hokwang Kwak, Jonghyun Hur, Jung-Hye Choi, Dae Sik Jang. Constituents of the stem barks of Ailanthus altissima and their potential to inhibit LPS-induced nitric oxide production. Bioorganic & medicinal chemistry letters. 2015 Mar; 25(5):1017-20. doi: 10.1016/j.bmcl.2015.01.034. [PMID: 25666824]
  • 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]
  • Weifeng Li, Wei Xing, Sicen Wang, Ting Fan, Huimin Huang, Xiaofeng Niu, Langchong He. An online coupled peritoneal macrophage/cell membrane chromatography and high-performance liquid chromatography/mass spectrometry method to screen for anti-inflammatory components from the Chinese traditional medicine Chloranthus multistachys Pei. Biomedical chromatography : BMC. 2013 Nov; 27(11):1580-6. doi: 10.1002/bmc.2963. [PMID: 23760986]
  • Rui-zhi Zhao, Ying Zhao, Li-qing Zhang, Chuan-jian Lu. Determination of isofraxidin and astilbin by HPLC in rat plasma and its application after orally administration the extract of Sarcandra glabra. Pakistan journal of pharmaceutical sciences. 2013 Jan; 26(1):1-6. doi: . [PMID: 23261720]
  • 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]
  • Shi-Ping Liu, Jing-Tao An, Rui Wang, Qiang Li. Simultaneous quantification of five bioactive components of Acanthopanax senticosus and its extract by ultra performance liquid chromatography with electrospray ionization time-of-flight mass spectrometry. Molecules (Basel, Switzerland). 2012 Jun; 17(7):7903-13. doi: 10.3390/molecules17077903. [PMID: 22751226]
  • Shumin Liu, Qiang Sun, Yun Bai, Fang Lu, Guangli Yan, Shunru Bao. [Analysis on isofraxidin contained in Acanthopanax senticosus extracts and its metabolites by UPLC-Q-TOF-MS and automatic data processing technique]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Jun; 37(12):1840-4. doi: 10.4268/cjcmm20121231. [PMID: 22997836]
  • Yanjing Bai, Chihiro Tohda, Shu Zhu, Masao Hattori, Katsuko Komatsu. Active components from Siberian ginseng (Eleutherococcus senticosus) for protection of amyloid β(25-35)-induced neuritic atrophy in cultured rat cortical neurons. Journal of natural medicines. 2011 Jul; 65(3-4):417-23. doi: 10.1007/s11418-011-0509-y. [PMID: 21301979]
  • Taisuke Yamazaki, Takayoshi Tokiwa. Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits matrix metalloproteinase-7 expression and cell invasion of human hepatoma cells. Biological & pharmaceutical bulletin. 2010; 33(10):1716-22. doi: 10.1248/bpb.33.1716. [PMID: 20930381]
  • Fang Min, Jin-ping Si, Wen-hua Huang, Hua-hong Huang, Shao-qing Lou, Guan-quan Zhu. [Studies on furmaric acid and isofraxidin content in Sarcandra glabra of different provenances]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Aug; 33(15):1849-53. doi: ". [PMID: 19007014]
  • Takuro Maruyama, Hiroyuki Kamakura, Miho Miyai, Katsuko Komatsu, Takeshi Kawasaki, Masao Fujita, Hiroshi Shimada, Yutaka Yamamoto, Toshiro Shibata, Yukihiro Goda. Authentication of the traditional medicinal plant Eleutherococcus senticosus by DNA and chemical analyses. Planta medica. 2008 Jun; 74(7):787-9. doi: 10.1055/s-2008-1074537. [PMID: 18500683]
  • Hui Sun, Haitao Lv, Yanmei Zhang, Xijun Wang, Kaishun Bi, Hongxin Cao. A rapid and sensitive UPLC-ESI MS method for analysis of isofraxidin, a natural antistress compound, and its metabolites in rat plasma. Journal of separation science. 2007 Dec; 30(18):3202-6. doi: 10.1002/jssc.200700251. [PMID: 17973275]
  • Hui Sun, Haitao Lv, Yanmei Zhang, Xiangcai Meng, Jinting Sui, Xijun Wang, Kaishun Bi. HPLC method for preliminary analysis of constituents in rat blood after oral administration of the extract of Acanthopanax senticosus. Journal of separation science. 2007 Dec; 30(18):3120-6. doi: 10.1002/jssc.200700265. [PMID: 18008282]
  • Hui Sun, Haitao Lv, Yanmei Zhang, Xijun Wang, Kaishun Bi, Hongxin Cao. Pharmacokinetics of isofraxidin in rat plasma after oral administration of the extract of Acanthopanax senticosus using HPLC with solid phase extraction method. Chemical & pharmaceutical bulletin. 2007 Sep; 55(9):1291-5. doi: 10.1248/cpb.55.1291. [PMID: 17827750]
  • Xiaoguang Zhou, Chunying Zheng, Jianshe Huang, Tianyan You. Identification of herb Acanthopanax senticosus (Rupr. Et Maxim.) harms by capillary electrophoresis with electrochemical detection. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2007 Jun; 23(6):705-11. doi: 10.2116/analsci.23.705. [PMID: 17575355]
  • Jiaqin Liu, Jianniao Tian, Zhide Hu, Xingguo Chen. Binding of isofraxidin to bovine serum albumin. Biopolymers. 2004 Mar; 73(4):443-50. doi: 10.1002/bip.20000. [PMID: 14991661]
  • Xinrong Yuan, Kaishun Bi, Qiang Li. [Study on the extraction process for free isofraxidin and hydrolytic condition of combined isofraxidin in Ciwujia with orthogonal design]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2004 Mar; 27(3):209-11. doi: ". [PMID: 15272788]
  • Jiaqin Liu, Jianniao Tian, Xuan Tian, Zhide Hu, Xingguo Chen. Interaction of isofraxidin with human serum albumin. Bioorganic & medicinal chemistry. 2004 Jan; 12(2):469-74. doi: 10.1016/j.bmc.2003.10.030. [PMID: 14723965]
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