从蝉花虫草提取的N~6-(2-羟乙基)腺苷的降压活性及其与人血清白蛋白的相互作用
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摘要
从蝉花虫草中提取分离了N~6-(2-羟乙基)腺苷[N~6-(2-hydroxyethyl)-adenosine,HEA],对其降压机制及其与人血清白蛋白的相互作用进行了研究,揭示了降压机制以及在体内的传输机制。研究结果表明使用水沉醇提法提取HEA,HEA的纯度达到95%以上。HEA低(2.5mg/kg)、中(5mg/kg)、高(7.5mg/kg)浓度组腹腔注射高血压大鼠体内,HEA具有显著降压效果,中浓度组表现出较稳定的降压作用,其机制可能是激活腺苷A1受体。在HEA与人血清白蛋白结合过程中,范德华力、氢键和疏水作用力是结合过程中的主要作用力,HEA在位点I与人血清白蛋白进行结合,结合过程轻微地改变人血清白蛋白的结构和微环境。分子对接结果表明,Ser-192、Lys-195、Arg-257、Ser-287和Arg-291是HEA与人血清白蛋白结合过程中重要的氨基酸残基。
Antihypertensive effect and intravascular transport mechanism of N~6-(2-hydroxyethyl)adenosine(HEA)isolated from Ophiocordyceps sobolifera,and interaction between HEA and human serum albumin(HSA)were studied.HEA with purity over 95%was obtained by using water-sinking extraction.Intraperitoneal injection of HEA at low(2.5mg/kg),medium(5mg/kg),and high(7.5mg/kg)concentration showed significant antihypertensive effect on the rats suffered from hypertension,and medium concentration particularly showed more effectiveness.The antihypertensive mechanism of HEA might be activation of adenosine A1receptor.Van der Waals force,hydrogen bonding and hydrophobic force were the main forces in the binding of HEA to human serum albumin.HEA bound to human serum albumin at site I.The structure and microenvironment of the human serum albumin was slightly changed during the binding process.Molecular docking results indicated that Ser-192,Lys-195,Arg-257,Ser-287 and Arg-291 were important amino acid residues for the interaction between HEA and human serum albumin.
Antihypertensive effect and intravascular transport mechanism of N~6-(2-hydroxyethyl)adenosine(HEA)isolated from Ophiocordyceps sobolifera,and interaction between HEA and human serum albumin(HSA)were studied.HEA with purity over 95%was obtained by using water-sinking extraction.Intraperitoneal injection of HEA at low(2.5mg/kg),medium(5mg/kg),and high(7.5mg/kg)concentration showed significant antihypertensive effect on the rats suffered from hypertension,and medium concentration particularly showed more effectiveness.The antihypertensive mechanism of HEA might be activation of adenosine A1receptor.Van der Waals force,hydrogen bonding and hydrophobic force were the main forces in the binding of HEA to human serum albumin.HEA bound to human serum albumin at site I.The structure and microenvironment of the human serum albumin was slightly changed during the binding process.Molecular docking results indicated that Ser-192,Lys-195,Arg-257,Ser-287 and Arg-291 were important amino acid residues for the interaction between HEA and human serum albumin.
引文
Chai YQ,Jin YW,Zhu BC,Li XL,Chen GJ,Liu YG,2013.Method for rapidly preparing high purity N6-(2-hydroxyethyl)adenosine:China,CN 103242402 A,2013-08-14(in Chinese)
Fang M,Chai YQ,Chen GJ,Wang HD,Huang B,2016.N6-(2-hydroxyethyl)-adenosine exhibits insecticidal activity against Plutella xylostellavia adenosine receptors.PLoS One,11(9):1-13
Feroz SR,Saharuddin BM,Noraini B,Sri NAM,Saad T,2012.Multispectroscopic and molecular modeling approach to investigate the interaction of flavokawain B with human serum albumin.Journal of Agricultural and Food Chemistry,60(23):5899-5908
Fleckenstein A,2003.Specific pharmacology of calcium in myocardium,cardiac pacemakers,and vascular smooth muscle.Annual Review of Pharmacology Toxicology,17(17):149-166
Frisch MJ,2006.Optimizing large molecules with Gaussian 03.Chemicke Listy,100(4):A9-A9
Furuya T,Hirotani M,Matsuzawa M,1983.N6-(2-hydroxyethyl)adenosine,a biologically active compound from cultured mycelia of Cordyceps and Isaria species.Phytochemistry,22(11):2509-2512
Gao H,Lei LD,Liu JQ,Kong Q,Chen XG,Hu ZD,2004.The study on the interaction between human serum albumin and a new reagent with antitumour activity by spectrophotometric methods.Journal of Photochemistry and Photobiology A:Chemistry,167(2004):213-221
Goddard TD,Huang CC,Feerin TE,2007.Visualizing density maps with UCSF chimera.Journal of Structural Biology,157(1):281-287
Hwangseo P,Lee J,Lee S,2006.Critical assessment of the automated AutoDock as a new docking tool for virtual screening.Proteins-Structure Function and Bioinformatics,65(3):549-554
Ibrahim N,Ibrahim H,Kim S,Nallet JP,Nepveu F,2010.Interactions between antimalarial indolone-N-oxide derivatives and human serum albumin.Biomacromolecules,11(12):3341-3351
Liu ZM,2013.Protective effect of calcium ion antagonist on cardiovascular organs in patients with essential hypertension.Practical Journal of Cardiac Cerebral Pneumal and Vascular Disease,21(8):60-61(in Chinese)
Makarska BM,2017.Interactions of hemin with bovine serum albumin and human hemoglobin:a fluorescence quenching study.Spectrochimica Acta Part A Molecular&Biomolecular Spectroscopy,193(5):23-32
Makarska BM,2018.Comparative study of binding interactions between porphyrin systems and aromatic compounds of biological importance by multiple spectroscopic techniques:a review.Spectrochimica Acta Part AMolecular&Biomolecular Spectroscopy,200(5):263-274
Mandal P,Ganguly T,2009.Fluorescence spectroscopic characterization of the interaction of human adult hemoglobin and two isatins,1-methylisatin and1-phenylisatin:a comparative study.Journal of Physical Chemistry B,113(45):14904-14913
Ni YN,Liu QH,Serge K,2011.Spectrophotometric study of the interaction between chlorotetracycline and bovine serum albumin using eosin Y as site marker with the aid of chemometrics.Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy,78(1):443-448
Olsson Tjelvar SG,Mark AW,William RP,John EL,2008.The thermodynamics of protein-ligand interaction and solvation:insights for ligand design.Journal of Molecular Biology,384(4):1002-1017
Peng XX,Chai YQ,Zhu BC,Jin YW,Li XL,Yu LS,2015.The protective effects of N6-(2-hydroxyethyl)-adenosine extracted from Ophiocordyceps sobolifera on renal ischemia reperfusion injury(IRI)in mice.Mycosystema,34(2):311-320(in Chinese)
Peters TJ,1996.All about albumin:biochemistry,genetics,and medical applications.Academic Press,San Diego,CA.432-450
Ross PD,Subramanian S,1981.Thermodynamics of protein association reactions-forces contributing to stability.Biochemistry,20(11):3096-3102
Shaw AK,Samir KP,2008.Resonance energy transfer and ligand binding studies on pH-induced folded states of human serum albumin.Journal of Photochemistry and Photobiology B-Biology,90(3):187-197
Sudlow G,Birkett DJ,Wade DN,1976.Further characterization of specific drug binding sites on human serum albumin.Molecular Pharmacology,12(6):1052-1061
Sugio S,Kashima A,Mochizuki S,Noda M,Kobayashi K,1999.Crystal structure of human serum albumin at 2.5angstrom resolution.Protein Engineering,12(6):439-446
Sung GH,Hywel JNL,Sung JM,Luangsa AJJ,Shrestha B,Spatafora JW,2007.Phylogenetic classification of Cordyceps and the clavicipitaceous fungi.Studies in Mycology,57:5-59
Suryawanshi VD,Anbhule PV,Gore AH,Patil SR,Kolekar GB,2012.Spectroscopic investigation on the interaction of pyrimidine derivative,2-amino-6-hydroxy-4-(3,4-dimethoxyphenyl)-pyrimidine-5-carbonitrile with human serum albumin:mechanistic and conformational study.Industrial&Engineering Chemistry Research,51(1):95-102
Tian FF,Jiang FL,Han XL,Chen X,Ge YS,Li JH,Zhang Y,Li R,Ding XL,Liu Y,2010.Synthesis of a novel hydrazone derivative and biophysical studies of its interactions with bovine serum albumin by spectroscopic,electrochemical,and molecular docking methods.Journal of Physical Chemistry B,114(46):14842-14853
Wang YQ,Wang XY,Wang J,Zhao YM,He WJ,Guo ZJ,2011.Noncovalent interactions between a trinuclear monofunctional platinum complex and human serum albumin.Inorganic Chemistry,50(24):12661-12668
Xiao JH,Qi Y,Xiong Q,2013.Nucleosides,a valuable chemical marker for quality control in traditional Chinese medicine Cordyceps.Recent Patents on Biotechnology,7(2):153-166
Yue YY,Liu JM,Fan J,Yao XJ,2011.Binding studies of phloridzin with human serum albumin and its effect on the conformation of protein.Journal of Pharmaceutical and Biomedical Analysis,56(2):336-342
Yue YY,Liu JM,Liu R,Sun YY,Li XG,Fan J,2014.The binding affinity of phthalate plasticizers-protein revealed by spectroscopic techniques and molecular modeling.Food and Chemical Toxicology,71(5):244-253
Zhang GW,Wang L,Pan JH,2012.Probing the binding of the flavonoid diosmetin to human serum albumin by multispectroscopic techniques.Journal of Agricultural and Food Chemistry,60(10):2721-2729
Zhang J,Zhuang SL,Tong CL,Liu WP,2013.Probing the molecular interaction of triazole fungicides with human serum albumin by multispectroscopic techniques and molecular modeling.Journal of Agricultural and Food Chemistry,61(30):7203-7211
Zhou H,Yu H,Han SY,2009.Progress in clinical application of calcium ion antagonists.Journal of Hebei United University(Medical Edition),11(2):175-177(in Chinese)
Zhou JH,Wu XH,Gu XT,Zhou L,Song KX,Wei SH,Feng YY,Shen J,2009.Spectroscopic studies on the interaction of hypocrellin A and hemoglobin.Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy,72(1):151-155
Zhu BC,Chai YQ,Zhang SS,Peng XX,Jin YW,Chen GJ,2016.Effects of active components from Ophiocordyceps sobolifera on anticonvulsions.Mycosystema,35(5):619-627(in Chinese)
Zhu WJ,Chai YQ,Jin YW,Li XL,Yu XP,2017.Effects of antinocieptive compound from Ophiocordyceps sobolifera on the transcriptome and Adora1 etc.pain-related genes in gouty rats.Mycosystema,36(1):48-59(in Chinese)
柴一秋,金轶伟,朱碧纯,厉晓腊,陈官菊,刘又高,2013.一种快速制备高纯度的N6-(2-羟乙基)腺苷的方法:CN103242402 A,2013-08-14
刘智梅,2013.钙离子拮抗剂对原发性高血压患者心血管器官的保护作用研究.中西医结合心血管病电子杂志,21(8):60-61
彭秀秀,柴一秋,朱碧纯,金轶伟,厉晓腊,喻林升,2015.蝉花虫草提取物N6-(2-羟乙基)腺苷对小鼠肾脏缺血再灌注损伤的保护作用.菌物学报,34(2):311-320
周辉,余红,韩淑英,2009.钙离子拮抗剂临床应用研究进展.河北联合大学学报(医学版),11(2):175-177
朱碧纯,柴一秋,章思思,彭秀秀,金轶伟,陈官菊,2016.蝉花虫草活性成分的抗惊厥作用.菌物学报,35(5):619-627
朱伟坚,柴一秋,金轶伟,厉晓腊,俞晓平,2017.蝉花虫草镇痛化合物对痛风大鼠转录组及Adora1等疼痛相关基因的影响.菌物学报,36(1):48-59
Fang M,Chai YQ,Chen GJ,Wang HD,Huang B,2016.N6-(2-hydroxyethyl)-adenosine exhibits insecticidal activity against Plutella xylostellavia adenosine receptors.PLoS One,11(9):1-13
Feroz SR,Saharuddin BM,Noraini B,Sri NAM,Saad T,2012.Multispectroscopic and molecular modeling approach to investigate the interaction of flavokawain B with human serum albumin.Journal of Agricultural and Food Chemistry,60(23):5899-5908
Fleckenstein A,2003.Specific pharmacology of calcium in myocardium,cardiac pacemakers,and vascular smooth muscle.Annual Review of Pharmacology Toxicology,17(17):149-166
Frisch MJ,2006.Optimizing large molecules with Gaussian 03.Chemicke Listy,100(4):A9-A9
Furuya T,Hirotani M,Matsuzawa M,1983.N6-(2-hydroxyethyl)adenosine,a biologically active compound from cultured mycelia of Cordyceps and Isaria species.Phytochemistry,22(11):2509-2512
Gao H,Lei LD,Liu JQ,Kong Q,Chen XG,Hu ZD,2004.The study on the interaction between human serum albumin and a new reagent with antitumour activity by spectrophotometric methods.Journal of Photochemistry and Photobiology A:Chemistry,167(2004):213-221
Goddard TD,Huang CC,Feerin TE,2007.Visualizing density maps with UCSF chimera.Journal of Structural Biology,157(1):281-287
Hwangseo P,Lee J,Lee S,2006.Critical assessment of the automated AutoDock as a new docking tool for virtual screening.Proteins-Structure Function and Bioinformatics,65(3):549-554
Ibrahim N,Ibrahim H,Kim S,Nallet JP,Nepveu F,2010.Interactions between antimalarial indolone-N-oxide derivatives and human serum albumin.Biomacromolecules,11(12):3341-3351
Liu ZM,2013.Protective effect of calcium ion antagonist on cardiovascular organs in patients with essential hypertension.Practical Journal of Cardiac Cerebral Pneumal and Vascular Disease,21(8):60-61(in Chinese)
Makarska BM,2017.Interactions of hemin with bovine serum albumin and human hemoglobin:a fluorescence quenching study.Spectrochimica Acta Part A Molecular&Biomolecular Spectroscopy,193(5):23-32
Makarska BM,2018.Comparative study of binding interactions between porphyrin systems and aromatic compounds of biological importance by multiple spectroscopic techniques:a review.Spectrochimica Acta Part AMolecular&Biomolecular Spectroscopy,200(5):263-274
Mandal P,Ganguly T,2009.Fluorescence spectroscopic characterization of the interaction of human adult hemoglobin and two isatins,1-methylisatin and1-phenylisatin:a comparative study.Journal of Physical Chemistry B,113(45):14904-14913
Ni YN,Liu QH,Serge K,2011.Spectrophotometric study of the interaction between chlorotetracycline and bovine serum albumin using eosin Y as site marker with the aid of chemometrics.Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy,78(1):443-448
Olsson Tjelvar SG,Mark AW,William RP,John EL,2008.The thermodynamics of protein-ligand interaction and solvation:insights for ligand design.Journal of Molecular Biology,384(4):1002-1017
Peng XX,Chai YQ,Zhu BC,Jin YW,Li XL,Yu LS,2015.The protective effects of N6-(2-hydroxyethyl)-adenosine extracted from Ophiocordyceps sobolifera on renal ischemia reperfusion injury(IRI)in mice.Mycosystema,34(2):311-320(in Chinese)
Peters TJ,1996.All about albumin:biochemistry,genetics,and medical applications.Academic Press,San Diego,CA.432-450
Ross PD,Subramanian S,1981.Thermodynamics of protein association reactions-forces contributing to stability.Biochemistry,20(11):3096-3102
Shaw AK,Samir KP,2008.Resonance energy transfer and ligand binding studies on pH-induced folded states of human serum albumin.Journal of Photochemistry and Photobiology B-Biology,90(3):187-197
Sudlow G,Birkett DJ,Wade DN,1976.Further characterization of specific drug binding sites on human serum albumin.Molecular Pharmacology,12(6):1052-1061
Sugio S,Kashima A,Mochizuki S,Noda M,Kobayashi K,1999.Crystal structure of human serum albumin at 2.5angstrom resolution.Protein Engineering,12(6):439-446
Sung GH,Hywel JNL,Sung JM,Luangsa AJJ,Shrestha B,Spatafora JW,2007.Phylogenetic classification of Cordyceps and the clavicipitaceous fungi.Studies in Mycology,57:5-59
Suryawanshi VD,Anbhule PV,Gore AH,Patil SR,Kolekar GB,2012.Spectroscopic investigation on the interaction of pyrimidine derivative,2-amino-6-hydroxy-4-(3,4-dimethoxyphenyl)-pyrimidine-5-carbonitrile with human serum albumin:mechanistic and conformational study.Industrial&Engineering Chemistry Research,51(1):95-102
Tian FF,Jiang FL,Han XL,Chen X,Ge YS,Li JH,Zhang Y,Li R,Ding XL,Liu Y,2010.Synthesis of a novel hydrazone derivative and biophysical studies of its interactions with bovine serum albumin by spectroscopic,electrochemical,and molecular docking methods.Journal of Physical Chemistry B,114(46):14842-14853
Wang YQ,Wang XY,Wang J,Zhao YM,He WJ,Guo ZJ,2011.Noncovalent interactions between a trinuclear monofunctional platinum complex and human serum albumin.Inorganic Chemistry,50(24):12661-12668
Xiao JH,Qi Y,Xiong Q,2013.Nucleosides,a valuable chemical marker for quality control in traditional Chinese medicine Cordyceps.Recent Patents on Biotechnology,7(2):153-166
Yue YY,Liu JM,Fan J,Yao XJ,2011.Binding studies of phloridzin with human serum albumin and its effect on the conformation of protein.Journal of Pharmaceutical and Biomedical Analysis,56(2):336-342
Yue YY,Liu JM,Liu R,Sun YY,Li XG,Fan J,2014.The binding affinity of phthalate plasticizers-protein revealed by spectroscopic techniques and molecular modeling.Food and Chemical Toxicology,71(5):244-253
Zhang GW,Wang L,Pan JH,2012.Probing the binding of the flavonoid diosmetin to human serum albumin by multispectroscopic techniques.Journal of Agricultural and Food Chemistry,60(10):2721-2729
Zhang J,Zhuang SL,Tong CL,Liu WP,2013.Probing the molecular interaction of triazole fungicides with human serum albumin by multispectroscopic techniques and molecular modeling.Journal of Agricultural and Food Chemistry,61(30):7203-7211
Zhou H,Yu H,Han SY,2009.Progress in clinical application of calcium ion antagonists.Journal of Hebei United University(Medical Edition),11(2):175-177(in Chinese)
Zhou JH,Wu XH,Gu XT,Zhou L,Song KX,Wei SH,Feng YY,Shen J,2009.Spectroscopic studies on the interaction of hypocrellin A and hemoglobin.Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy,72(1):151-155
Zhu BC,Chai YQ,Zhang SS,Peng XX,Jin YW,Chen GJ,2016.Effects of active components from Ophiocordyceps sobolifera on anticonvulsions.Mycosystema,35(5):619-627(in Chinese)
Zhu WJ,Chai YQ,Jin YW,Li XL,Yu XP,2017.Effects of antinocieptive compound from Ophiocordyceps sobolifera on the transcriptome and Adora1 etc.pain-related genes in gouty rats.Mycosystema,36(1):48-59(in Chinese)
柴一秋,金轶伟,朱碧纯,厉晓腊,陈官菊,刘又高,2013.一种快速制备高纯度的N6-(2-羟乙基)腺苷的方法:CN103242402 A,2013-08-14
刘智梅,2013.钙离子拮抗剂对原发性高血压患者心血管器官的保护作用研究.中西医结合心血管病电子杂志,21(8):60-61
彭秀秀,柴一秋,朱碧纯,金轶伟,厉晓腊,喻林升,2015.蝉花虫草提取物N6-(2-羟乙基)腺苷对小鼠肾脏缺血再灌注损伤的保护作用.菌物学报,34(2):311-320
周辉,余红,韩淑英,2009.钙离子拮抗剂临床应用研究进展.河北联合大学学报(医学版),11(2):175-177
朱碧纯,柴一秋,章思思,彭秀秀,金轶伟,陈官菊,2016.蝉花虫草活性成分的抗惊厥作用.菌物学报,35(5):619-627
朱伟坚,柴一秋,金轶伟,厉晓腊,俞晓平,2017.蝉花虫草镇痛化合物对痛风大鼠转录组及Adora1等疼痛相关基因的影响.菌物学报,36(1):48-59