Cimifugin (BioDeep_00000403078)

Main id: BioDeep_00000000295

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(2S)-7-(hydroxymethyl)-2-(1-hydroxy-1-methyl-ethyl)-4-methoxy-2,3-dihydrofuro[3,2-g]chromen-5-one

化学式: C16H18O6 (306.1103)
中文名称: 升麻素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(C)(C1CC2=C(O1)C=C3C(=C2OC)C(=O)C=C(O3)CO)O
InChI: InChI=1S/C16H18O6/c1-16(2,19)13-5-9-11(22-13)6-12-14(15(9)20-3)10(18)4-8(7-17)21-12/h4,6,13,17,19H,5,7H2,1-3H3/t13-/m0/s1

描述信息

Cimifugin (Cimitin) is a bioactive component of Cimicifuga racemosa, a Chinese herb. Cimifugin suppresses allergic inflammation by reducing epithelial derived initiative key factors via regulating tight junctions[1]. Cimifugin reduces the migration and chemotaxis of RAW264.7 cells and inhibits the release of inflammatory factors and activation of MAPKs and NF-κB signaling pathways induced by LPS[2].
Cimifugin (Cimitin) is a bioactive component of Cimicifuga racemosa, a Chinese herb. Cimifugin suppresses allergic inflammation by reducing epithelial derived initiative key factors via regulating tight junctions[1]. Cimifugin reduces the migration and chemotaxis of RAW264.7 cells and inhibits the release of inflammatory factors and activation of MAPKs and NF-κB signaling pathways induced by LPS[2].

同义名列表

10 个代谢物同义名

(2S)-7-(hydroxymethyl)-2-(1-hydroxy-1-methyl-ethyl)-4-methoxy-2,3-dihydrofuro[3,2-g]chromen-5-one; (2S)-7-(hydroxymethyl)-2-(1-hydroxy-1-methylethyl)-4-methoxy-2,3-dihydrofuro[3,2-g]chromen-5-one; (2S)-7-(hydroxymethyl)-2-(2-hydroxypropan-2-yl)-4-methoxy-2,3-dihydrofuro[3,2-g]chromen-5-one; (2S)-2-(1-hydroxy-1-methyl-ethyl)-4-methoxy-7-methylol-2,3-dihydrofuro[3,2-g]chromen-5-one; 37921-38-3; Cimifugin; C09000; Cimitin; Cimifugin; Cimifugin



数据库引用编号

12 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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Plant Reactome(0)

INOH(0)

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43 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 9 AIMP2, MAPK8, MARVELD1, PRKAA2, SIRT1, SPR, TLR4, TNFSF11, TYR
Peripheral membrane protein 2 ACHE, GORASP1
Endosome membrane 1 TLR4
Nucleus 6 ACHE, AIMP2, MAPK8, MARVELD1, PRKAA2, SIRT1
cytosol 5 AIMP2, MAPK8, PRKAA2, SIRT1, SPR
dendrite 1 PRKAA2
nucleoplasm 4 MAPK8, PRKAA2, SIRT1, SPR
Cell membrane 6 ACHE, MARVELD1, TLR4, TNF, TNFSF11, TRPV4
Cytoplasmic side 1 GORASP1
lamellipodium 1 TRPV4
ruffle membrane 1 TRPV4
Multi-pass membrane protein 3 CLDND1, MARVELD1, TRPV4
Golgi apparatus membrane 1 GORASP1
Synapse 2 ACHE, MAPK8
cell surface 6 ACHE, ADIPOQ, CLDND1, TLR4, TNF, TRPV4
Golgi apparatus 3 ACHE, GORASP1, PRKAA2
Golgi membrane 2 GORASP1, INS
growth cone 1 TRPV4
neuromuscular junction 1 ACHE
neuronal cell body 2 PRKAA2, TNF
Cytoplasm, cytosol 1 AIMP2
Lysosome 1 TYR
plasma membrane 7 ACHE, BCHE, MARVELD1, TLR4, TNF, TNFSF11, TRPV4
Membrane 8 ACHE, AIMP2, CLDND1, MARVELD1, PRKAA2, TLR4, TNFSF11, TRPV4
apical plasma membrane 2 CLDND1, TRPV4
axon 2 MAPK8, PRKAA2
extracellular exosome 1 SPR
endoplasmic reticulum 2 ADIPOQ, TRPV4
extracellular space 9 ACHE, ADIPOQ, BCHE, IL17A, IL22, INS, TNF, TNFSF11, TSLP
perinuclear region of cytoplasm 3 ACHE, TLR4, TYR
adherens junction 1 TRPV4
mitochondrion 2 SIRT1, SPR
intracellular membrane-bounded organelle 1 TYR
filopodium 1 TRPV4
chromatin silencing complex 1 SIRT1
Single-pass type I membrane protein 2 TLR4, TYR
Secreted 8 ACHE, ADIPOQ, BCHE, IL17A, IL22, INS, TNFSF11, TSLP
extracellular region 9 ACHE, ADIPOQ, BCHE, IL17A, IL22, INS, TNF, TNFSF11, TSLP
Extracellular side 1 ACHE
Cell projection, cilium 1 TRPV4
external side of plasma membrane 3 IL17A, TLR4, TNF
nucleolus 1 SIRT1
Melanosome membrane 1 TYR
Early endosome 1 TLR4
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 2 TNF, TNFSF11
Apical cell membrane 1 TRPV4
heterochromatin 1 SIRT1
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 MARVELD1
focal adhesion 1 TRPV4
cis-Golgi network 1 GORASP1
Cell junction, adherens junction 1 TRPV4
basement membrane 1 ACHE
collagen trimer 1 ADIPOQ
Nucleus, PML body 1 SIRT1
PML body 1 SIRT1
collagen-containing extracellular matrix 1 ADIPOQ
nuclear speck 1 PRKAA2
nuclear inner membrane 1 SIRT1
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
receptor complex 1 TLR4
cilium 1 TRPV4
chromatin 1 SIRT1
phagocytic cup 2 TLR4, TNF
cytoskeleton 1 MARVELD1
blood microparticle 1 BCHE
Lipid-anchor, GPI-anchor 1 ACHE
fibrillar center 1 SIRT1
nuclear envelope 1 SIRT1
endosome lumen 1 INS
Melanosome 1 TYR
cytoplasmic stress granule 1 PRKAA2
euchromatin 1 SIRT1
side of membrane 1 ACHE
lipopolysaccharide receptor complex 1 TLR4
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 BCHE, INS
cortical actin cytoskeleton 1 TRPV4
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GORASP1, INS
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
nuclear envelope lumen 1 BCHE
[Isoform 2]: Cytoplasm 1 TNFSF11
[Tumor necrosis factor ligand superfamily member 11, soluble form]: Secreted 1 TNFSF11
cytoplasmic microtubule 1 TRPV4
synaptic cleft 1 ACHE
basal dendrite 1 MAPK8
[Isoform 1]: Cell membrane 1 TRPV4
eNoSc complex 1 SIRT1
rDNA heterochromatin 1 SIRT1
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
nucleotide-activated protein kinase complex 1 PRKAA2
[Isoform 2]: Endoplasmic reticulum 1 TRPV4
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[Isoform 5]: Cell membrane 1 TRPV4
[Isoform H]: Cell membrane 1 ACHE
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[Isoform 4]: Endoplasmic reticulum 1 TRPV4
[SirtT1 75 kDa fragment]: Cytoplasm 1 SIRT1
[Isoform 6]: Endoplasmic reticulum 1 TRPV4


文献列表

  • Xiaoqun Gu, Yanyan Chen, Peiyao Qian, Ting He, Yameng Wu, Wei Lin, Jie Zheng, Min Hong. Cimifugin suppresses type 2 airway inflammation by binding to SPR and regulating its protein expression in a non-enzymatic manner. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Mar; 111(?):154657. doi: 10.1016/j.phymed.2023.154657. [PMID: 36701995]
  • Wenwen Yang, Linwensi Zhu, Shanglei Lai, Qinchao Ding, Tiantian Xu, Rui Guo, Xiaobing Dou, Hui Chai, Zhiling Yu, Songtao Li. Cimifugin Ameliorates Lipotoxicity-Induced Hepatocyte Damage and Steatosis through TLR4/p38 MAPK- and SIRT1-Involved Pathways. Oxidative medicine and cellular longevity. 2022; 2022(?):4557532. doi: 10.1155/2022/4557532. [PMID: 35355867]
  • Jiajia Sun, Xiangyi Su, Zhe Zhang, Dexiang Hu, Guige Hou, Feng Zhao, Jufeng Sun, Wei Cong, Chunhua Wang, Hongjuan Li. Separation of three chromones from Saposhnikovia divaricata using macroporous resins followed by preparative high-performance liquid chromatography. Journal of separation science. 2021 Sep; 44(17):3287-3294. doi: 10.1002/jssc.202100345. [PMID: 34240798]
  • Hiroyuki Fuchino, Sayaka Murase, Atsuyuki Hishida, Nobuo Kawahara. Simultaneous UHPLC/MS quantitative analysis and comparison of Saposhnikoviae radix constituents in cultivated, wild and commercial products. Journal of natural medicines. 2021 Jun; 75(3):499-519. doi: 10.1007/s11418-021-01486-1. [PMID: 33575969]
  • Jinjin Yan, Fan Ye, Ying Ju, Dijun Wang, Jiao Chen, Xinyu Zhang, Zhi Yin, Changming Wang, Yan Yang, Chan Zhu, Yuan Zhou, Peng Cao, Yang Xu, Guang Yu, Zongxiang Tang. Cimifugin relieves pruritus in psoriasis by inhibiting TRPV4. Cell calcium. 2021 May; 97(?):102429. doi: 10.1016/j.ceca.2021.102429. [PMID: 34087722]
  • Aimin Liu, Wei Zhao, Buxin Zhang, Yuanhui Tu, Qingxing Wang, Jing Li. Cimifugin ameliorates imiquimod-induced psoriasis by inhibiting oxidative stress and inflammation via NF-κB/MAPK pathway. Bioscience reports. 2020 06; 40(6):. doi: 10.1042/bsr20200471. [PMID: 32515468]
  • Lu Yao, Siqi Wang, Pan Wei, Kaifan Bao, Weiyuan Yuan, Xiaotong Wang, Jie Zheng, Min Hong. Huangqi-Fangfeng protects against allergic airway remodeling through inhibiting epithelial-mesenchymal transition process in mice via regulating epithelial derived TGF-β1. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Nov; 64(?):153076. doi: 10.1016/j.phymed.2019.153076. [PMID: 31473579]
  • Jie Zheng, Xiaoyu Wang, Yu Tao, Yan Wang, Xi Yu, Hailiang Liu, Lv Ji, Kaifan Bao, Can Wang, Zhirong Jia, Min Hong. Yu-Ping-Feng-San ameliorates recurrent allergic inflammation of atopic dermatitis by repairing tight junction defects of the epithelial barrier. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Feb; 54(?):214-223. doi: 10.1016/j.phymed.2018.09.190. [PMID: 30668371]
  • Bin Han, Yuan Dai, Haiyan Wu, Yuanyuan Zhang, Lihong Wan, Jianlei Zhao, Yuanqi Liu, Shijun Xu, Liming Zhou. Cimifugin Inhibits Inflammatory Responses of RAW264.7 Cells Induced by Lipopolysaccharide. Medical science monitor : international medical journal of experimental and clinical research. 2019 Jan; 25(?):409-417. doi: 10.12659/msm.912042. [PMID: 30638197]
  • Masakazu Nishihara, Keiji Nukui, Yuko Osumi, Hironori Shiota. [Quality Evaluation of Saposhnikoviae Radix (Differences between Wild-type and Cultivated Products)]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2018 Apr; 138(4):571-579. doi: 10.1248/yakushi.17-00208. [PMID: 29386422]
  • Xiaoyu Wang, Xiaoyan Jiang, Xi Yu, Hailiang Liu, Yu Tao, Guorong Jiang, Min Hong. Cimifugin suppresses allergic inflammation by reducing epithelial derived initiative key factors via regulating tight junctions. Journal of cellular and molecular medicine. 2017 Nov; 21(11):2926-2936. doi: 10.1111/jcmm.13204. [PMID: 28597545]
  • Xiao-Li Zhao, Ling Liu, Liu-Qing Di, Jun-Song Li, An Kang. [Studies on effects of calycosin-7-O-β-D-glucoside on prim-O-glucosylcimifugin and cimifugin in vivo pharmacokinetics]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 Dec; 39(23):4669-74. doi: . [PMID: 25911821]
  • Yu Yang, Yang Zhang, Feng-Xia Ren, Neng-Jiang Yu, Rui Xu, Yi-Min Zhao. [Chemical constituents from the roots of Angelica polymorpha Maxim]. Yao xue xue bao = Acta pharmaceutica Sinica. 2013 May; 48(5):718-22. doi: . [PMID: 23888695]
  • Tao Li, Yiwei Wang, Yanli Wang, Rixin Liang, Dong Zhang, Huihui Zhang, Li Chen, Weipeng Yang. Development of an SPE-HPLC-MS method for simultaneous determination and pharmacokinetic study of bioactive constituents of Yu Ping Feng San in rat plasma after oral administration. Journal of ethnopharmacology. 2013 Feb; 145(3):784-92. doi: 10.1016/j.jep.2012.12.010. [PMID: 23261488]
  • Yue-Yue Li, Xin-Xia Wang, Liang Zhao, Hai Zhang, Lei Lv, Gui-chen Zhou, Yi-Feng Chai, Guo-Qing Zhang. High-performance liquid chromatography-electrospray ionization time-of-flight mass spectrometry analysis of Radix Saposhnikoviae for metabolomic research. Journal of chromatographic science. 2013 Feb; 51(2):99-106. doi: 10.1093/chromsci/bms111. [PMID: 22824330]
  • Yueyue Li, Liang Zhao, Hai Zhang, Jing Jia, Lei Lv, Guichen Zhou, Yifeng Chai, Guoqing Zhang. Comparative pharmacokinetics of prim-O-glucosylcimifugin and cimifugin by liquid chromatography-mass spectrometry after oral administration of Radix Saposhnikoviae extract, cimifugin monomer solution and prim-O-glucosylcimifugin monomer solution to rats. Biomedical chromatography : BMC. 2012 Oct; 26(10):1234-40. doi: 10.1002/bmc.2684. [PMID: 22253022]
  • Bo Zhao, Xin-Bao Yang, Xiu-Wei Yang, Jian-Xun Liu. Biotransformation of prim-O-glucosylcimifugin by human intestinal flora and its inhibition on NO production and DPPH free radical. Journal of Asian natural products research. 2012; 14(9):886-96. doi: 10.1080/10286020.2012.702756. [PMID: 22917273]
  • Bei Jiang, Chunhui Ma, Timothy Motley, Fredi Kronenberg, Edward J Kennelly. Phytochemical fingerprinting to thwart black cohosh adulteration: a 15 Actaea species analysis. Phytochemical analysis : PCA. 2011 Jul; 22(4):339-51. doi: 10.1002/pca.1285. [PMID: 21337649]
  • Wei Li, Zi Wang, Yin-shi Sun, Li Chen, Li-kun Han, Yi-nan Zheng. Application of response surface methodology to optimise ultrasonic-assisted extraction of four chromones in Radix Saposhnikoviae. Phytochemical analysis : PCA. 2011 Jul; 22(4):313-21. doi: 10.1002/pca.1282. [PMID: 21438050]
  • Zhao-Guang Zheng, Ru-Shang Wang, Hui-Quan Cheng, Ting-Ting Duan, Bao He, Dan Tang, Fei Gu, Quan Zhu. Isolated perfused lung extraction and HPLC-ESI-MS(n) analysis for predicting bioactive components of Saposhnikoviae Radix. Journal of pharmaceutical and biomedical analysis. 2011 Feb; 54(3):614-8. doi: 10.1016/j.jpba.2010.09.034. [PMID: 20970279]
  • Xijun Wang, Zenghui Wang, Hui Sun, Haitao Lv, Hongying Guan, Xiangcai Meng, Haifeng Sun, Guangmei Zhang, Hongxin Cao. Pharmacokinetics of cimifugin in rat plasma after oral administration of the extract of Saposhnikovia divaricatae root. Determination of cimifugin by high performance liquid chromatography coupled with solid phase extraction. Arzneimittel-Forschung. 2008; 58(9):445-50. doi: 10.1055/s-0031-1296537. [PMID: 18972874]