乔松素临床应用和作用机制的研究进展
详细信息    查看全文 | 推荐本文 |
  • 英文篇名:Research Progress on Pinocembrin:Potential Therapeutic Applications and Action Mechanisms
  • 作者:张海威 ; 张力
  • 英文作者:Zhang Hai-wei;Zhang Li;Department of Pharmacy,Hebei North University;
  • 关键词:乔松素 ; 药物代谢动力学 ; 治疗应用 ; 作用机制 ; 研究进展
  • 英文关键词:pinocembrin;;pharmacokinetics;;therapeutic applications;;mechanisms of action;;research progress
  • 中文刊名:ZJKB
  • 英文刊名:Acta Neuropharmacologica
  • 机构:河北北方学院药学系;
  • 出版日期:2016-10-26
  • 出版单位:神经药理学报
  • 年:2016
  • 期:v.6;No.35
  • 基金:国家自然科学基金项目(No.81274005);; 河北省研究生创新资助项目(No.CXZZSS2017146)
  • 语种:中文;
  • 页:ZJKB201605007
  • 页数:8
  • CN:05
  • ISSN:13-1404/R
  • 分类号:47-54
摘要
乔松素是一种天然的黄酮类化合物,在蜂胶、姜科植物、牛至属植物等植物中有较高的含量。在临床前期研究中,乔松素表现出良好的抗炎、抗肿瘤、抗氧化、降低血脂和神经保护作用等。近年来国内外对乔松素神经保护方面的研究发现,其可以通过减少活性氧产生、保护血脑屏障完整性、调节线粒体功能和调控细胞凋亡等发挥作用。该文对乔松素的药物代谢动力学和潜在的治疗应用及其作用机制等方面进行综述,为乔松素的后续研究提供参考。
        Pinocembrin is a natural flavonoid compound extracted from propolis,ginger plants,wild marjoram,and other plants which have a higher content. In the preclinical studies,it has shown anti-inflammatory,anti-tumor,antioxidant,decrease blood lipids,neuroprotective effects and other pharmacological effects. In recent domestic and foreign studies focused on pinocembrin neuroprotective effects as well as the ability to attenuate reactive oxygen species,protect the blood-brain barrier,modulate mitochondrial function,and regulate apoptosis. Pinocembrin is a potential drug to treat ischemic stroke and other clinical conditions. In this review,we summarize its pharmacokinetics,mechanisms of action and potential therapeutic applications,in order to provide a reference for pinocembrin mechanisms research and therapeutic applications.
引文
[1]C Flavia Massaro Inoz,M Katouli,Tanja Grkovic,et al.Anti-staphylococcal activity of C-methyl flavanones from propolis of Australian stinglessbees(Tetragonula carbonari-a)and fruit resins of Corymbia torelliana(Myrtaceae)[J].Fitoterapia,2014,3:24.
    [2]Carolina F Danert,Catiana Zampini,Roxana Ordonez,et al.Nutritional and functional properties of aqueous and hydroalcoholic extracts from argentinean propolis[J].Nat Prod Commun,2014,9(2):167-170.
    [3]R.D.Vargas-Sánchez,A.M.Mendoza-Wilson,R.R.Balandran-Quintana,et al.Study of the molecular structure and chemical reactivity of pinocembrin by DFTcalculations[J].Comput Theor Chem,2015,1057:21-27.
    [4]Wu Jun-jun,Zhang Xia,Dong Ming-sheng,et al.Stepwise modular pathway engineering of Escherichia colifor efficient one-step production of(2S)-pinocembrin[J].JBiothchnol,2016,231:183-192.
    [5]Wu Jun-jun,Zhang Xia,Dong Ming-sheng,et al.Efficient biosynthesis of(2S)-pinocembrin from d-glucose by integrating engineering central metabolic pathways with a pH-shift control strategy[J].Bioresource Technol,2016,218:999-1007.
    [6]Georgina N Diaz Napal,Sara M Palacios.Phytotoxicity of secondary metabolites isolated from Flourensia oolepis S.F.Blake[J].Chem Biodivers,2013,10(7):1295-1304.
    [7]Yuan Yue,Yang Qing-yun,Tong Yuan-feng,et al.Synthesis and enantiomeric resolution of(+/-)-pinocembrin[J].JAsian Nat Prod Res,2008,10(9-10):999-1002.
    [8]Muhammed A Saad,Rania Abdel Salam R M,Kenawy S A,et al.Pinocembrin attenuates hippocampal inflammation,oxidative perturbations and apoptosis in a rat model of global cerebral ischemia reperfusion[J].Pharmacological reports:PR,2015,67:115-122.
    [9]Yang Zhi-hong,Sun Xiao,Yun Qi,e t a l.Uptake characteristics of pinocembrin and its effect on p-glycoprotein at the blood-brain barrier in vitro cell experiments[J].J Asian Nat Prod Res,2012,14(1):14-21.
    [10]Yan Bei,Cao Guo-ying,Sun Tao-hua,et al.Determination of pinocembrin in human plasmaby solidphase extraction and LC/MS/MS:application to pharmacokinetic studies[J].Biomed Chromatogr,2014,Doi:10.1002/bmc.3186.
    [11]Wang Y J.National Institutes of Health Phase II study of pinocembrin injection to treat ischemic stroke[J/OL].ClinicalTrials.gov,2014.http://www.clinicaltrials.gov/ct2/show/NCT02059785?term=pinocembrin&rank=1.
    [12]Yang Zhi-hong,Liu Rui,Li Xiao-xiu,et al.Development and validation of ahigh-performance liquid chromatographic method for determination of pinocembrin in rat plasma:application to pharmacokinetic study[J].Pharm Biomed Anal,2009,49(5):1277-1281.
    [13]Chiral L Sayre,Jody K Takemoto,Stephanie E Martinez,et al.Chiral analytical method development and application to preclinical pharmacokinetics of pinocembrin[J].Biomed Chromatogr,2013,27(6):681-684.
    [14]Liu Y L,Ho David K,John M Cassady,et al.Isolation of potential cancer chemopreventive agents from Eriodictyon californicum[J].J Nat Prod,1992,55(3):357-363.
    [15]Bernd Weisshaar,Gareth I Jenkins.Phenylpropanoid biosynthesis and its regulation[J].Curr Opin Plant Biol,1998,1(3):251-257.
    [16]Masafumi Kaneko,Eui ILHwang,Yasuo Ohnishi,et al.Heterologous production of flavanones in Escherichia coli:potential for combinatorial biosynthesis of flavonoids in bacteria[J].J Ind Microbiol Biotechnol,2003,30(8):456-461.
    [17]Yan Ya-jun,Abhijeet Kohli,Mattheos A G Koffas.Biosynthesis of natural flavanones in Saccharomyces cerevisiae[J].Appl Environ Microbiol,2005,71(9):5610-5613.
    [18]Bong-Gyu Kim,Lee Hyejin,Joong-Hoon Ahn.Biosynthesis of pinocembrin from glucose using engineered Escherichia coli[J].J Microbiol Biotechnol,2014,24(11):1536-1541.
    [19]Dariush Mozaffarian,Emelia J Benjamin,Alan S Go,et al.Executive summary:heart disease and stroke statistics2015 update:a report from the American Heart Association[J].Circulation,2015,131(4):434-441.
    [20]Shi Li-li,Chen Bai-nian,Gao Mei,et al.The characteristics of therapeutic effect of pinocembrin in transient global brain ischemia/reperfusion rats[J].Life Sci,2011,88(11-12):521-528.
    [21]Gao Mei,Zhang We n-c u i,Liu Qing-shan,e t a l.Pinocembrin prevents glutamate-induced apoptosis in SHSY5Yneuronal cells via decrease of bax/bcl-2 ratio[J].Eur J P-harmacol,2008,591(1-3):73-79.
    [22]Hiroshi Izuta,Masamitsu Shimazawa,Shigemi Tazawa,et al.Protective effects of Chinese propolis and its component,chrysin,against neuronal cell death via inhibition of mitochondrial apoptosis pathway in SH-SY5Ycells[J].J Agric Food Chem,2008,56(19):8944-8953.
    [23]Liu R,Gao M,Yang Z H,et al.Pinocembrin protects rat brain against oxidation and apoptosis induced by ischemiareperfusion both in vivo and in vitro[J].Brain Res,2008,1216:104-115.
    [24]Gao Mei,Zhu Shen-yin,Tan Chu-bing,et al.Pinocembrin protects the neurovascular unit by reducing inflammation and extracellular proteolysis in MCAO rats[J].J Asian Nat Prod Res,2010,12(5):407-418.
    [25]Gao Mei,Liu Rui,Zhu Shen-yin,et al.Acute neurovascular unit protective action of pi-nocembrin against permanent cerebral ischemia in rats[J].J Asian Nat Prod Res,2008,10(5-6):551-558.
    [26]Wang Shou-bao,P a n g Xiao-bin,Gao Mei,e t a l.Pinocembrin protects rats against cerebral ischemic damage through soluble epoxide hydrolase and epoxyeicosatrienoic acids[J].Chin J Nat Med,2013,11(3):207-213.
    [27]Jeffrey J Iliff,Nabil J Alkayed.Soluble epoxide hydrolase inhibition:targeting multiple mechanisms of ischemic brain injury with a single agent[J].Future Neurol,2009,4(2):179-199.
    [28]Koichi Node,Huo Yu-qing,Ruan Xiu-lu,et al.Antiinflammatory properties of cytochrome P450 epoxygenasederived eicosanoids[J].Science,1999,285(5431):1276-1279.
    [29]Jorge H Capdevila,John R Falck.The CYP P450arachidonic acid monooxygenases:from cell signaling to blood pressure regulation[J].Biochem Biophys Res Commun,2001,285(3):571-576.
    [30]John D Imig,Alexis N Simpkins,Marija Renic.Cytochrome P450 eicosanoids and cerebral vascular function[J].Expert Rev Mol Med,2011,13:e7.
    [31]Jeremy Bellien,Robinson Joannides.Epoxyeicosatrienoic acid pathway in human health and diseases[J].JCardiovasc Pharmacol,2013,61(3):188-196.
    [32]Priyanka Sura,Radhakrishna Sura,Ahmed E Enayetallah,et al.Distribution and expression of soluble epoxide hydrolase in human brain[J].J Histochem Cytochem,2008,56(6):551-559.
    [33]Sari A Jouihan,Kristen L Zuloaga,Zhang Wen-ri,et al.Role of soluble epoxide hydrolase in exacerbation of stroke by streptozotocin-induced type 1 diabetes mellitus[J].JCereb Blood Flow Metab,2013,33(10):1650-1656.
    [34]Zhang Wen-ri,Ines P Koerner,Ruediger Noppens,et al.Soluble epoxide hydrolase:a novel therapeutic target in stroke[J].J Cereb Blood Flow Metab,2007,27(12):1931-1940.
    [35]Zhang Wen-ri,Takashi Otsuka,Nobuo Sugo,et al.Soluble epoxide hydrolase gene deletion is protective against experimental cerebral ischemia[J].Stroke,2008,39(7):2073-2078.
    [36]Jafar Sadik Shaik,Muzamil Ahmad,Li Wen-jin,et al.Soluble epoxide hydrolase inhibitor trans-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid is neuroprotective in rat model of ischemic stroke[J].Am JPhysiol Heart Circ Physiol,2013,305(11):H1605-H1613.
    [37]Christian Brenneis,Marco Sisignano,Ovidiu Coste,et al.Soluble epoxide hydrolase limits mechanical hyperalgesia during inflammation[J].Mol Pain,2011,7:78.
    [38]Wu Cai-xia,Liu Rui,Gao Mei,et al.Pinocembrin protects brain against ischemia/reperfusion injury by attenuating endoplasmic reticulum stress induced apoptosis[J].Neurosci Lett,2013,546:57-62.
    [39]Meng Fan-rui,Liu Rui,Gao Mei,et al.Pinocembrin attenuates blood-brain barrier injury induced by global cerebral ischemia-reperfusion in rats[J].Brain Res,2011,1391:93-101.
    [40]Muhammed A Saad,Rania M Abdel Salam,Sanaa AKenawy,et al.Pinocembrin attenuates hippoca-mpal inflammation,oxidative perturbations and apoptosis in a rat model of global cerebral ischemia reperfusion[J].Pharmacol Rep,2015,67(1):115-122.
    [41]Shi Li-li,Chen Bai-nian,Gao Mei,et al.The characteristics of therapeutic effect of pinocembrin in transient global brain ischemia/reperfusion rats[J].Life Sci,2011,88(11-12):521-528.
    [42]Denise M Boudreau,Gregory F Guzauskas,Chen Er,et al.Cost-effectiveness of recombinant tissuetype plasminogen activator within 3 hours of acute ischemic stroke:current evidence[J].Stroke,2014,45(10):3032-3039.
    [43]Liu Rui,Wu Cai-xia,Zhou Dan,et al.Pinocembrin protects against beta-amyloid-induced toxicity in neurons through inhibiting receptor for advanced glycation end products(RAGE)-independent signaling pathways and regulating mitochondrion-mediated apoptosis[J].BMC Med,2012,10:105.
    [44]Liu Rui,Li Jin-ze,Song Jun-ke,et al.Pinocembrin improves cognition and protects the neurovascular unit in Alzheimer related deficits[J].Neurobiol Aging,2014,35(6):1275-1285.
    [45]Wang Yu-min,Miao Ying-chun,Aamina Zia Mir,et al.Inhibition of beta-amyloid-induced neurotoxicity by pinocembrin through Nrf2/HO-1pathway in SH-SY5Y cells[J].J Neurol Sci,2016,368:223-230.
    [46]Wang Yu-min,Gao Jun-hong,Miao Ying-chun,et al.Pinocembrin protects SH-SY5Y cells against MPP(+)-induced neurotoxicity through the mitochondrial apoptotic pathway[J].J Mol Neurosci,2014,53(4):537-545.
    [47]Wang H Q,Wang Y M,Zhao L N,et al.Pinocembrin attenuates MPP+-induced neurotoxicity by the induction of heme oxygenase-1 through ERK1/2 pathway[J].Neurosci Lett,2016,612:104-109.
    [48]Jin Xiao-hua,Liu Qian,Jia Li-li,et al.Pinocembrin attenuates 6-OHDA-induced neuronal cell death through Nrf2/ARE pathway in SH-SY5Y cells[J].Cell Mol Neurobiol,2014,35:323-333..
    [49]Li Li,Yang Hai-guang,Yuan Tian-yi,et al.Rho kinase inhibition activity of pinocembrin in rat aortic rings contracted by angiotensin II[J].Chin J Nat Med,2013,11(3):258-263.
    [50]Sang Hui,Yuan Na,Yao Shu-tong,et al.Inhibitory effect of the combination therapy of simvastatin and pinocembrin on atherosclerosis in ApoE-deficient mice[J].Lipids Health Dis,2012,11:166.
    [51]袁娜.乔松素对ApoE-/-小鼠动脉粥样硬化影响的实验研究[D].泰山:泰山医学院,2010.
    [52]Yang Nana,Qin Shu-cun,Wang Meng-zan,e t a l.Pinocembrin,a major flavonoid in propolis,improves the biological functions of EPCs derived from rat bone marrow through the PI3K-eNOS-NO signaling pathway[J].Cytotechnology,2013,65(4):541-551.
    [53]李伟,李冬娟,杨艳.乔松素对脂多糖诱导的人脐静脉内皮细胞凋亡的影响[J].中国动脉粥样硬化杂志,2010,18(5):351-354.
    [54]Lamiaa A Ahmed,Sherine M Rizk,Shohda A ELMaraghy.Pinocembrin ex vivo preconditioni-ng improves the therapeutic efficacy of endothelial progenitor cells in monocrotaline-induced pulmonary hypertension in rats[J].Biochem Pharmacol,2017,138:193-204.
    [55]Lanan Wassy Soromou,Chu Xiao,Jiang Lan-xiang,et al.In vitro and in vivo protection providedby pinocembrin against lipopolysaccharide-induced inflammatory responses[J].Int Immunopharmacol,2012,14(1):66-74.
    [56]Zhou Lu-ting,Wang Ke-jia,Li Ling,et al.Pinocembrin inhibits lipopolysaccharide-induced inflammatory mediators production in BV2 microglial cells through suppression of PI3K/Akt/NF-κB pathway[J].Eur.J.Pharmacol,2015,761:211-216.
    [57]Soromou L W,Jiang L,Wei M,et al.Protection of mice against lipopolysaccha-ride-induced endotoxic shock by pinocembrin is correlated with regulation of cytokine secretion[J].J Immunotoxicol,2014,11(1):56-61.
    [58]兰那.乔松素抗金黄色葡萄球菌感染和抗炎作用及机制的研究[D].长春:吉林大学,2013.
    [59]Sib S G,Shib S S,Venkatachalam S,et al.Pinocembrin attenuates lipopolysacc-haride-induced inflammatory responses in Labeorohita macrophages via the suppression of the NF-κB signalling pathway[J].Fish Shellfishi Immun,2016,56:459-466.
    [60]Metzner J,Schneidewind E M,Friedrich E.Effect of propolis and pinocembrin on fungi[J].Pharmazie,1977,32(11):730.
    [61]Araceli Sala,M Carmen Recio,Guillermo R Schinella,et al.Assessment of the anti-inflammatory activity and free radical scavenger activity of tiliroside[J].Eur JPharmacol,2003,461(1):53-61.
    [62]Metzner J,Schneidewind E M.Effect of pinocembrin on the course of experimental candida infections in mice[J].Mykosen,1978,21(8):257-262.
    [63]Atac Uzel,Kadri Sorkun,Ozant Oncag,et al.Chemical compositions and antimicrobial activities of four different Anatolian propolis samples[J].Microbiol Res,2005,160(2):189-195.
    [64]David R Katerere,Alexander I Gray,Robert J Nash,et al.Phytochemical and antimicrobial investigations of stilbenoids and flavonoids isolated from three species of Combretaceae[J].Fitoterapia,2012,83(5):932-940.
    [65]Leticia M Estevinho,Ana Paula Pereira,Leandro Moreira,et al.Antioxidant and antimicrobial effects of phenolic compounds extracts of Northeast Portugal honey[J].Food Chem Toxicol,2008,46(12):3774-3779.
    [66]Mariana Peralta,Maximiliano Calise,M Cecilia Fornari,et al.A prenylated flavanone from Dalea elegans inhibits rhodamine 6 G efflux and reverses fluconazole-resistance inCandida albicans[J].Planta Med,2012,78(10):981-987.
    [67]Ahmed G Hegazi,Faten K Abd EI Hady,Fayrouz A M Abd Allah.Chemical composition and anti-microbial activity of European propolis[J].Z Naturforsch C,2000,55(1-2):70-75.
    [68]Yong K Park,Michel H Koo,Jose A S Abreu,et al.Antimicrobial activity of propolis on oral-microorganisms[J].Curr Microbiol,1998,36(1):24-28.
    [69]Leticia Barrientos,Christian L Herrera,Gloria Montenegro,et al.Chemical and botanical characterization of Chilean propolis and biological activity on cariogenic bacteria Streptococcus mutans and Streptococcus sobrinus[J].Braz J Microbiol,2013,44(2):577-585.
    [70]Patrick Ruddock,Marijo Charland,Sandra Ramirez,et al.Antimicrobial activity of flavonoids from Piper lanceaefolium and other Colombian medicinal plants against antibiotic susceptible and resistant strains of Neisseria gonorrhoeae[J].Sex Transm Dis,2011,38(2):82-88.
    [71]Soromou Lanan Wassy,Zhang Yu,Cui Yi-wen,et al.Subinhibitory concentrations of pinocembrin exert antiStaphylococcus aureus activity by reducing alphatoxinBexpression[J].J Appl Microbiol,2013,115(1):41-49.

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700