Cimifugin 7-glucoside (BioDeep_00000230296)

 

Secondary id: BioDeep_00000403080

PANOMIX_OTCML-2023


代谢物信息卡片


(S)-2-(2-hydroxypropan-2-yl)-4-methoxy-7-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-2H-furo[3,2-g]chromen-5(3H)-one

化学式: C22H28O11 (468.16315380000003)
中文名称: 升麻素苷, 升麻苷
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 22.41%

分子结构信息

SMILES: CC(C)(C1CC2=C(O1)C=C3C(=C2OC)C(=O)C=C(O3)COC4C(C(C(C(O4)CO)O)O)O)O
InChI: InChI=1S/C22H28O11/c1-22(2,28)15-5-10-12(32-15)6-13-16(20(10)29-3)11(24)4-9(31-13)8-30-21-19(27)18(26)17(25)14(7-23)33-21/h4,6,14-15,17-19,21,23,25-28H,5,7-8H2,1-3H3/t14-,15+,17-,18+,19-,21-/m1/s1

描述信息

PRIM-O-GLUCOSYLCIMIFUGIN is an organic heterotricyclic compound and an oxacycle.
Prim-O-glucosylcimifugin is a natural product found in Ostericum grosseserratum, Saposhnikovia divaricata, and other organisms with data available.
Prim-O-glucosylcimifugin exerts anti-inflammatory effects through the inhibition of iNOS and COX-2 expression by through regulating JAK2/STAT3 signaling.
Prim-O-glucosylcimifugin exerts anti-inflammatory effects through the inhibition of iNOS and COX-2 expression by through regulating JAK2/STAT3 signaling.

同义名列表

12 个代谢物同义名

(S)-2-(2-hydroxypropan-2-yl)-4-methoxy-7-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-2H-furo[3,2-g]chromen-5(3H)-one; (2S)-2-(2-hydroxypropan-2-yl)-4-methoxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydrofuro[3,2-g]chromen-5-one; (2S)-2-(2-hydroxypropan-2-yl)-4-methoxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydrouro[3,2-g]chromen-5-one; 5H-Furo[3,2-g][1]benzopyran-5-one,7-[(b-D-glucopyranosyloxy)methyl]-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-4-methoxy-, (S)-; [(2S)-2-(2-Hydroxypropan-2-yl)-4-methoxy-5-oxo-2,3-dihydro-5H-furo[3,2-g][1]benzopyran-7-yl]methyl beta-D-glucopyranoside; Cimifugin beta-D-glucopyranoside; CIMIFUGINBETA-D-GLUCOPYRANOSIDE; prim-O-b-D-Glucosylcimifugin; prim-O-glucosyl cimifugin; prime-O-glucosylcimifugin; Prim-O-glucosylcimifugin; Cimifugin 7-glucoside



数据库引用编号

7 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)

2 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

  • 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]
  • Yulong Gu, Xianglan Piao, Dan Zhu. Simultaneous determination of calycosin, prim-O-glucosylcimifugin, and paeoniflorin in rat plasma by HPLC-MS/MS: application in the pharmacokinetic analysis of HQCF. The Journal of international medical research. 2020 Nov; 48(11):300060520972902. doi: 10.1177/0300060520972902. [PMID: 33213240]
  • Zolboo Batsukh, Kazufumi Toume, Batkhuu Javzan, Kohei Kazuma, Shao-Qing Cai, Shigeki Hayashi, Nobuo Kawahara, Takuro Maruyama, Katsuko Komatsu. Metabolomic profiling of Saposhnikoviae Radix from Mongolia by LC-IT-TOF-MS/MS and multivariate statistical analysis. Journal of natural medicines. 2020 Jan; 74(1):170-188. doi: 10.1007/s11418-019-01361-0. [PMID: 31578667]
  • Wanfeng Gao, Xiaoyun Zhang, Wendong Yang, Daolei Dou, Heng Zhang, Yuanhao Tang, Weilong Zhong, Jing Meng, Yun Bai, Yanrong Liu, Lan Yang, Shuang Chen, Huijuan Liu, Cheng Yang, Tao Sun. Prim-O-glucosylcimifugin enhances the antitumour effect of PD-1 inhibition by targeting myeloid-derived suppressor cells. Journal for immunotherapy of cancer. 2019 08; 7(1):231. doi: 10.1186/s40425-019-0676-z. [PMID: 31462297]
  • Lu Xu, Jieyi Cai, Aofei Tian, Kai Qian, Renan Qin, Shaoyun Qi, Xupeng Tan, Yuqin Qiu, Mengjuan Gong, Bin Han, Xuguang Hu. The Effect of Prim-O-Glucosylcimifugin on Tryptase-Induced Intestinal Barrier Dysfunction in Caco-2 Cells. Biological & pharmaceutical bulletin. 2018 Sep; 41(9):1355-1361. doi: 10.1248/bpb.b18-00059. [PMID: 29910215]
  • 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]
  • Lu Zhang, Xiaodi Liu, Xiongbin Lu, Cheng Huang. Prim-O-glucosylcimifugin induces cell cycle arrest and apoptosis in acute lymphoblastic leukemia cells. Anti-cancer drugs. 2017 10; 28(9):943-951. doi: 10.1097/cad.0000000000000543. [PMID: 28692435]
  • Jie Zhou, Yuan-Yuan Sun, Meng-Yao Sun, Wei-An Mao, Li Wang, Jian Zhang, Hong Zhang. Prim-O-glucosylcimifugin Attenuates Lipopolysaccharideinduced Inflammatory Response in RAW 264.7 Macrophages. Pharmacognosy magazine. 2017 Jul; 13(51):378-384. doi: 10.4103/pm.pm_323_16. [PMID: 28839360]
  • Tong-Fang Wang, Jian-Ping Wang, Jin-Huo Pan, Zhi-Tao Jiang, Xiao-Feng Chen, Jian-Chun Wang. [Nasal resorption of prim-O-glucosylcimifugin and 5-O-methylvisammioside in rats]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2017 May; 42(9):1772-1776. doi: 10.19540/j.cnki.cjcmm.20170224.001. [PMID: 29082705]
  • 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]
  • Jue Song, Shi-rui Zheng, Yong Jin, Jun Li. Pharmacokinetic Interaction of astragaloside IV with atractylenolide I and prim-O-glucosylcimifugin in male Sprague Dawley rats. Planta medica. 2014 Feb; 80(2-3):187-92. doi: 10.1055/s-0033-1360261. [PMID: 24452462]
  • 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]
  • 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]
  • Yan-Yan Jiang, Bin Liu, Ren-Bing Shi, Guang-Zhong Tu. [Isolation and structure identification of chemical constituents from Saposhnikovia divaricata (Turcz.) Schischk]. Yao xue xue bao = Acta pharmaceutica Sinica. 2007 May; 42(5):505-10. doi: . [PMID: 17703773]
  • Li Li, Yuan-Yan Liu, Li-Dong Geng, Yong-Qing Xiao. [Determination of four components in root of Saposhnikovia divaricata by HPLC gradient elution]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Feb; 31(3):194-6. doi: ". [PMID: 16572995]
  • Xian-Li Wu, Yi Li, Ling-Yi Kong, Zhi-Da Min. Two compounds from Peucedanum dissolutum. Journal of Asian natural products research. 2004 Dec; 6(4):301-5. doi: 10.1080/1028602031000147429. [PMID: 15621591]