Praeruptorin A (BioDeep_00000230106)

 

Secondary id: BioDeep_00000230953, BioDeep_00000715363

PANOMIX_OTCML-2023


代谢物信息卡片


2-Butenoic acid, 2-methyl-,(9S,10S)-10-(acetyloxy)-9,10-dihydro-8,8-dimethyl-2-oxo-2H,8H-benzo[1,2-b:3,4-b]dipyran-9-yl ester, (2Z)-

化学式: C21H22O7 (386.1365462)
中文名称: 白花前胡甲素, (±)-白花前胡甲素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C/C=C(C)\C(O[C@H]1[C@@H](OC(C)=O)C2=C3C(C=CC(O3)=O)=CC=C2OC1(C)C)=O
InChI: InChI=1S/C21H22O7/c1-6-11(2)20(24)27-19-18(25-12(3)22)16-14(28-21(19,4)5)9-7-13-8-10-15(23)26-17(13)16/h6-10,18-19H,1-5H3/b11-6-/t18-,19-/m0/s1

描述信息

(+)-Praeruptorin A is a natural product found in Ligusticum lucidum, Peucedanum japonicum, and Prionosciadium thapsoides with data available.
(±)-Praeruptorin A is the di-esterified product of cis-khellactone (CKL) and the major active ingredient in Peucedani Radix which consists of the dried roots of Peucedanum praeruptorumDunn (Apiaceae). (±)-Praeruptorin A has been widely employed as one of the famous traditional Chinese medicines (TCMs) for the treatment of cough with thick sputum and dyspnea, nonproductive cough and upper respiratory infections for centuries in China. (±)-Praeruptorin A has dramatically therapeutic effects on hypertension mainly through acting as a Ca2+-influx blocker[1].
(±)-Praeruptorin A is the di-esterified product of cis-khellactone (CKL) and the major active ingredient in Peucedani Radix which consists of the dried roots of Peucedanum praeruptorumDunn (Apiaceae). (±)-Praeruptorin A has been widely employed as one of the famous traditional Chinese medicines (TCMs) for the treatment of cough with thick sputum and dyspnea, nonproductive cough and upper respiratory infections for centuries in China. (±)-Praeruptorin A has dramatically therapeutic effects on hypertension mainly through acting as a Ca2+-influx blocker[1].
Praeruptorin A is a main bioactive constituent of Peucedanum praeruptorum (also known as Bai-Hua Qian Hu). Praeruptorin A exerts anti-inflammatory effects in vitro through inhibition of NF-κB activation[1].
Praeruptorin A is a main bioactive constituent of Peucedanum praeruptorum (also known as Bai-Hua Qian Hu). Praeruptorin A exerts anti-inflammatory effects in vitro through inhibition of NF-κB activation[1].

同义名列表

10 个代谢物同义名

2-Butenoic acid, 2-methyl-,(9S,10S)-10-(acetyloxy)-9,10-dihydro-8,8-dimethyl-2-oxo-2H,8H-benzo[1,2-b:3,4-b]dipyran-9-yl ester, (2Z)-; (9S,10S)-10-(Acetyloxy)-8,8-dimethyl-2-oxo-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b]dipyran-9-yl (2Z)-2-methylbut-2-enoate; [(9S,10S)-10-acetyloxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-9-yl] (Z)-2-methylbut-2-enoate; ( inverted exclamation markA)-Praeruptorin A; (+-)-Praeruptorin A; (+)-Praeruptorin A; (-)-pareruptorin A; (-)-Praeruptorin A; Praeruptorin A; (±)-Praeruptorin A



数据库引用编号

9 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)

1 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

  • Zhenkun Li, Fengrong Zhang, Shicong Wang, Honghe Xiao, Jingyi Wang, Xianyu Li, Hongjun Yang. Endothelium-dependent vasorelaxant effects of praeruptorin a in isolated rat thoracic aorta. Bioengineered. 2022 04; 13(4):10038-10046. doi: 10.1080/21655979.2022.2062979. [PMID: 35416124]
  • Yijuan Hu, Hongjian Zhang, Weiqing Liang, Pan Xu, Kelang Lou, Jinbao Pu. Rapid and Simultaneous Measurement of Praeruptorin A, Praeruptorin B, Praeruptorin E, and Moisture Contents in Peucedani Radix Using Near-Infrared Spectroscopy and Chemometrics. Journal of AOAC International. 2020 Apr; 103(2):504-512. doi: 10.5740/jaoacint.19-0126. [PMID: 31561752]
  • Anna Lewinska, Lakshman Sodagam, Dominika Bloniarz, Karsten Siems, Maciej Wnuk, Suresh I S Rattan. Plant-Derived Molecules α-Boswellic Acid Acetate, Praeruptorin-A, and Salvianolic Acid-B Have Age-Related Differential Effects in Young and Senescent Human Fibroblasts In Vitro. Molecules (Basel, Switzerland). 2019 Dec; 25(1):. doi: 10.3390/molecules25010141. [PMID: 31905790]
  • Meng Chen, Ruimiao Chang, Liying Xu, Yayun Huang, Hongfen Zhang, Anjia Chen. Simultaneous separation and determination of praeruptorin A, B and C by micellar electrokinetic chromatography using sodium dodecyl sulphate and sodium cholate as mixed micelles. Phytochemical analysis : PCA. 2018 Sep; 29(5):425-431. doi: 10.1002/pca.2746. [PMID: 29392793]
  • Cong Xu, Mengyue Luo, Huidi Jiang, Lushan Yu, Su Zeng. Involvement of CAR and PXR in the transcriptional regulation of CYP2B6 gene expression by ingredients from herbal medicines. Xenobiotica; the fate of foreign compounds in biological systems. 2015; 45(9):773-81. doi: 10.3109/00498254.2015.1020076. [PMID: 25869249]
  • Xianhua Zhang, Yueping Wu, Ying Hong, Xuan Zhu, Liang Lin, Qingjiang Lin. Preparation and evaluation of dl-praeruptorin A microemulsion based hydrogel for dermal delivery. Drug delivery. 2015; 22(6):757-64. doi: 10.3109/10717544.2014.898713. [PMID: 24724963]
  • Xueqin Ding, Li Li, Yuzhi Wang, Jing Chen, Yanhua Huang, Kaijia Xu. Design of guanidinium ionic liquid based microwave-assisted extraction for the efficient extraction of Praeruptorin A from Radix peucedani. Journal of separation science. 2014 Dec; 37(23):3539-47. doi: 10.1002/jssc.201400828. [PMID: 25243924]
  • Yue-Lin Song, Wang-Hui Jing, Yan-Gan Chen, Yun-Fei Yuan, Ru Yan, Yi-Tao Wang. ¹H nuclear magnetic resonance based-metabolomic characterization of Peucedani Radix and simultaneous determination of praeruptorin A and praeruptorin B. Journal of pharmaceutical and biomedical analysis. 2014 May; 93(?):86-94. doi: 10.1016/j.jpba.2013.08.021. [PMID: 24041522]
  • Yue-Lin Song, Wang-Hui Jing, Ru Yan, Yi-Tao Wang. Metabolic characterization of (±)-praeruptorin A in vitro and in vivo by high performance liquid chromatography coupled with hybrid triple quadrupole-linear ion trap mass spectrometry and time-of-flight mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2014 Mar; 90(?):98-110. doi: 10.1016/j.jpba.2013.10.010. [PMID: 24342524]
  • Yuelin Song, Wanghui Jing, Fengqing Yang, Zhan Shi, Meicun Yao, Ru Yan, Yitao Wang. Simultaneously enantiospecific determination of (+)-trans-khellactone, (+/-)-praeruptorin A, (+/-)-praeruptorin B, (+)-praeruptorin E, and their metabolites, (+/-)-cis-khellactone, in rat plasma using online solid phase extraction-chiral LC-MS/MS. Journal of pharmaceutical and biomedical analysis. 2014 Jan; 88(?):269-77. doi: 10.1016/j.jpba.2013.08.042. [PMID: 24095802]
  • Ling Huang, Hui-chang Bi, Yu-Hua Li, Jun-Qing Zhang, Shao-Yi Kuang, Li Zhang, Yi-Tao Wang, Min Huang. Regulation of human pregnane X receptor and its target gene cytochrome P450 3A by praeruptorin A isolated from the herbal medicine Peucedanum praeruptorum. Planta medica. 2013 Nov; 79(16):1509-15. doi: 10.1055/s-0033-1350795. [PMID: 24037590]
  • Pravin O Patil, Sanjay B Bari, Sandip D Firke, Prashant K Deshmukh, Shailesh T Donda, Dilip A Patil. A comprehensive review on synthesis and designing aspects of coumarin derivatives as monoamine oxidase inhibitors for depression and Alzheimer's disease. Bioorganic & medicinal chemistry. 2013 May; 21(9):2434-50. doi: 10.1016/j.bmc.2013.02.017. [PMID: 23517722]
  • Xu-Nian Zhou, Hui-Chang Bi, Jing Jin, Rong-Rong Deng, Meng-Jia Ying, Yong-Tao Wang, Min Huang. [Induction of UGT1A1 expression by praeruptorin A and praeruptorin C through hCAR pathway]. Yao xue xue bao = Acta pharmaceutica Sinica. 2013 May; 48(5):794-8. doi: ". [PMID: 23888707]
  • Parisa Sarkhail, Abbas Shafiee, Pantea Sarkheil. Biological activities and pharmacokinetics of praeruptorins from Peucedanum species: a systematic review. BioMed research international. 2013; 2013(?):343808. doi: 10.1155/2013/343808. [PMID: 24371820]
  • You-yi Xiong, Jun-song Wang, Fei-hua Wu, Juan Li, Ling-yi Kong. The effects of (±)-Praeruptorin A on airway inflammation, remodeling and transforming growth factor-β1/Smad signaling pathway in a murine model of allergic asthma. International immunopharmacology. 2012 Dec; 14(4):392-400. doi: 10.1016/j.intimp.2012.08.019. [PMID: 22974581]
  • Youyi Xiong, Junsong Wang, Feihua Wu, Juan Li, Linfu Zhou, Lingyi Kong. Effects of (±)-praeruptorin A on airway inflammation, airway hyperresponsiveness and NF-κB signaling pathway in a mouse model of allergic airway disease. European journal of pharmacology. 2012 May; 683(1-3):316-24. doi: 10.1016/j.ejphar.2012.03.004. [PMID: 22449378]
  • Y L Song, W H Jing, H Y Zhao, R Yan, P T Li, Y T Wang. Stereoselective metabolism of (±)-praeruptorin A, a calcium channel blocker from Peucedani Radix, in pooled liver microsomes of rats and humans. Xenobiotica; the fate of foreign compounds in biological systems. 2012 Mar; 42(3):231-7. doi: 10.3109/00498254.2011.609250. [PMID: 21957884]
  • Hang Ruan, Zhen Zhang, Xin-fang Liang, Yan Fu, Mei-qin Su, Qi-lin Liu, Xiu-min Wang, Xuan Zhu. Metabolism of dl-praeruptorin A in rat liver microsomes using HPLC-electrospray ionization tandem mass spectrometry. Archives of pharmacal research. 2011 Aug; 34(8):1311-21. doi: 10.1007/s12272-011-0811-y. [PMID: 21910053]
  • Z Zhang, Y Y Liu, M Q Su, X F Liang, W F Wang, X Zhu. Pharmacokinetics, tissue distribution and excretion study of dl-praeruptorin A of Peucedanum praeruptorum in rats by liquid chromatography tandem mass spectrometry. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2011 Apr; 18(6):527-32. doi: 10.1016/j.phymed.2010.09.009. [PMID: 21036581]
  • Ling Huang, Hui-Chang Bi, Ya-He Liu, Yi-Tao Wang, Xin-Ping Xue, Min Huang. CAR-mediated up-regulation of CYP3A4 expression in LS174T cells by Chinese herbal compounds. Drug metabolism and pharmacokinetics. 2011; 26(4):331-40. doi: 10.2133/dmpk.dmpk-10-rg-115. [PMID: 21422673]
  • Taigang Liang, Wenyan Yue, Qingshan Li. Chemopreventive effects of Peucedanum praeruptorum DUNN and its major constituents on SGC7901 gastric cancer cells. Molecules (Basel, Switzerland). 2010 Nov; 15(11):8060-71. doi: 10.3390/molecules15118060. [PMID: 21063269]
  • Hang Ruan, Zhen Zhang, Xuan Zhu. Liquid chromatography tandem mass spectrometry pharmacokinetic study of DL-praeruptorin A in rat plasma. Biomedical chromatography : BMC. 2010 Nov; 24(11):1193-8. doi: 10.1002/bmc.1426. [PMID: 20954210]
  • Zhao Xu, Xiaobing Wang, Yue Dai, Lingyi Kong, Fengyun Wang, Huan Xu, Dan Lu, Jie Song, Zhiguo Hou. (+/-)-Praeruptorin A enantiomers exert distinct relaxant effects on isolated rat aorta rings dependent on endothelium and nitric oxide synthesis. Chemico-biological interactions. 2010 Jul; 186(2):239-46. doi: 10.1016/j.cbi.2010.04.024. [PMID: 20433815]
  • Ai-dong Liu, Wei Hou, Xue-song Chen, Zhi-dong Qiu. [Extraction of praeruptorin A from Radix Peucedani by supercritical fluid extraction-CO2]. Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine. 2008 Dec; 6(12):1286-9. doi: 10.3736/jcim20081215. [PMID: 19063845]
  • He Chang, Xiao-yu Chu, Jun Zou, Tian-hui Chang. Effect of dl-praeruptorin A on desmin and vimentin content in rat ischemia/reperfusion myocardiocytes. Chinese medical journal. 2007 Dec; 120(24):2256-9. doi: ". [PMID: 18167213]
  • Cun Zhang, Li Li, Li-dong Geng, Yuan-yan Liu, Na Lin, Yong-qing Xiao. [Studies on quality standard of Peucedanum praeruptorum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Feb; 30(3):177-9. doi: ". [PMID: 15719631]
  • Tian-Hui Chang, Xiao-Yang Liu, Xin-Hua Zhang, Huai-Liang Wang. Effects of dl-praeruptorin A on interleukin-6 level and Fas, bax, bcl-2 protein expression in ischemia-reperfusion myocardium. Acta pharmacologica Sinica. 2002 Sep; 23(9):769-74. doi: NULL. [PMID: 12230942]
  • M Lu, M Nicoletti, L Battinelli, G Mazzanti. Isolation of praeruptorins A and B from Peucedanum praeruptorum Dunn. and their general pharmacological evaluation in comparison with extracts of the drug. Farmaco (Societa chimica italiana : 1989). 2001 May; 56(5-7):417-20. doi: 10.1016/s0014-827x(01)01053-9. [PMID: 11482769]