植物源1-脱氧野尻霉素分离纯化技术综述
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摘要
1-脱氧野尻霉素(DNJ)是从桑树等植物中分离的一种具有降血糖功效的天然活性物质。由于植物DNJ的分离纯化存在较多困难,因此限制了天然DNJ在糖尿病临床治疗中的应用。本文基于天然DNJ的溶解性能、吸附与解吸附性能以及分子质量大小等,对近年来国内外有关植物DNJ的分离纯化技术研究进展进行分类概述和讨论,以期为桑树DNJ分离纯化工艺技术的实用化改进提供有益参考。
1-Deoxynojirimycin(DNJ) is a natural active substance with hypoglycemic activity isolated from mulberry and other plants. Its application in clinical therapy of diabetes is limited by the difficulty in separation and purification from plant materials. In this paper,research advances in separation and purification technology of DNJ from plant are reviewed and discussed from the aspects of natural DNJ solubility,adsorption and desorption,molecular size,etc,which may provide useful references for market-oriented improvement on separation and purification technology of DNJ from mulberry.
1-Deoxynojirimycin(DNJ) is a natural active substance with hypoglycemic activity isolated from mulberry and other plants. Its application in clinical therapy of diabetes is limited by the difficulty in separation and purification from plant materials. In this paper,research advances in separation and purification technology of DNJ from plant are reviewed and discussed from the aspects of natural DNJ solubility,adsorption and desorption,molecular size,etc,which may provide useful references for market-oriented improvement on separation and purification technology of DNJ from mulberry.
引文
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[2]Nitra N,Kornkanok I,Wiroje K,et al.Quantitative determination of1-deoxynojirimycin in mulberry leaves using liquid chromatographytandem mass spectrometry[J].J Pharmaceut Biomed,2007,44(4):853-858
[3]Toshiyuki K,Kiyotaka N,Yuko S,et al.Determination of 1-deoxynojirimycin in mulberry leaves using hydrophilic interaction chromatography with evaporative light scattering detection[J].J Agric Food Chem,2004,52(6):1415-1418
[4]Kazuhisa Y,Masatoshi I,Satoshi O.The relationship between 1-deoxynojirimycin content andα-glucosidase inhibitory activity in leaves of 276 mulberry cultivars(Morus spp.)in Kyoto[J].Japan J Nat Med,2008,62(1):63-66
[5]Chaluntorn V,Kiyotaka N,Phumon S,et al.Development of high1-deoxynojirimycin(DNJ)content mulberry tea and use of response surface methodology to optimize tea-making conditions for highest DNJ extraction[J].LWT-Food Sci Technol,2012,45(2):226-232
[6]Kim H S,Kim Y H,Hong Y S,et al.α-Glucosidase inhibitors from Cornmelina communis[J].Planta Med,1999,65(5):437-439
[7]Asano N,Kato A,Miyanchi M,et al.Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientatis[J].J Nat Ptod,1998,61(5):625-628
[8]Asano N,Nishida M,Miyauchi M,et al.Polyhydroxylated pyrrolidine and piperidine alkaloids from Adenophora triphylla var.japonica(Campanulaceae)[J].Phytochemistry,2000,53(3):379-382
[9]Zhu Y P,Yamaki K,Yoshihashi T,et al.Purification and identification of 1-deoxynojirimycin(DNJ)in okara fermented by Bacillus subtilis B2 from chinese traditional food(meitaoza)[J].J Agric Food Chem,2010,58(7):4097-4103
[10]徐立,刘超,刘静,等.制备桑叶方便食品的调味料及其桑叶方便食品和制备方法:中国,201310293660.9[P].2013-09-25
[11]Michiru Y,Youichi T,Fumiko M,et al.Binding parameters and thermodynamics of the interaction of imino sugars with a recombinant human acidα-glucosidase(alglucosidase alfa):insight into the complex formation mechanism[J].Clin Chim Acta,2008,391(1/2):68-73
[12]Toshiyuki K,Kiyotaka N,Hiroyuki K,et al.Food-grade mulberry powder enriched with 1-deoxynojirimycin suppresses the elevation of postprandial blood glucose in humans[J].J Agric Food Chem,2007,55(14):5869-5874
[13]Tsuruok A T,Tamur A A,Matsuhashi Y,et al.Binding of D-methionine to peptidoglycan in the presence of inhibitors of cell wall synthesis in Escherichia coli[J].Agric Biol Chem,1985,49(8):2489-2490
[14]Eike S,Thomas W,Stephanie K.Antiviral effects of amantadine and iminosugar derivatives against hepatitis C virus[J].Hepatology,2007,46(2):330-338
[15]Fenouillet E,Papandréou M J,Jones I M.Recombinant HIV envelope expressed in anα-glucosidase I-deficient CHO cell line and its parental cell line in the presence of 1-deoxynojirimycin is functional[J].Virology,1997,231(1):89-95
[16]Kim J Y,Choi B G,Jung M J,et al.Mulberry leaf water extract ameliorates insulin sensitivity in high fator high sucrose diet induced overweight rats[J].J Korean Soc Appl Bi,2011,54(4):612-618
[17]杨青,郑晓瑞,陈红梅,等.1-脱氧野尻霉素衍生物的研究进展[J].中国生化药物杂志,2010,31(1):1-5
[18]陈燕军,冯青然.常用精制方法在纯化中药制剂中的应用[J].中国实验方剂学杂志,2003,9(3):56-60
[19]黄建,周玉飞,翟龙飞,等.1-脱氧野尻霉素晶体的制备及稳定性[J].应用化工,2012,41(12):2050-2056
[20]殷红.脱氧野尻霉素的一种纯化方法:中国,201110422786.2[P].2012-06-13
[21]黄建伟.桑叶中1-脱氧野尻霉素的制备方法:中国,201110021131.4[P].2011-08-17
[22]马全民,聂复礼,李雪斌,等.由桑叶中提取分离高纯度1-脱氧野尻霉素的方法:中国,201110038204.0[P].2011-06-22
[23]杨茹,卢朝华.天然产物中提取分离高纯1-脱氧野尻霉素的方法:中国,200910167602.5[P].2010-02-24
[24]孟夏.桑叶中1-脱氧野尻霉素的分离纯化技术研究[D].镇江:江苏大学,2008
[25]黄华学,唐方华,刘永胜.一种从桑叶中提取1-脱氧野尻霉素的方法:中国,201110087108.5[P].2011-09-21
[26]欧阳臻,孟夏,常钰,等.一种从桑叶总生物碱中分离1-脱氧野尻霉素单体的方法:中国,200810122998.7[P].2008-12-03
[27]向华.一种从桑叶提取1-脱氧野尻霉素和白藜芦醇的方法:中国,201110234164.7[P].2012-02-15
[28]唐忠梅.一种从植物中同时提取1-脱氧野尻霉素和白藜芦醇的方法:中国,201210162994.8[P].2012-10-17
[29]冯旭东,刘明明,路娟,等.等电点-冷却结晶去除谷氨酸中的焦谷氨酸[J].食品科学,2013,34(20):19-22
[30]叶青,裘兆蓉,韶晖,等.用降膜结晶法分离人造麝香的研究[J].化工进展,2004,23(11):1233-1235
[31]张世文,姚祖凤.萃取-结晶法制备高纯辣椒碱类化合物[J].吉首大学学报:自然科学版,2002,2(2):90-92
[32]艾秀珍,沈波,危凤,等.萃取-结晶法制备辣椒碱类化合物工艺研究[J].天然产物研究与开发,2008(20):150-153
[33]李宇亮,李剑敏,吴雅睿.1-脱氧野尻霉素提取分离方法研究[J].应用化工.2006,35(9):659-665
[34]杭伟锋,鲍玲,刘刚,等.一种从桑叶中连续提取分离1-脱氧野尻霉素(DNJ)、黄酮的方法:中国,200910192542.2[P].2010-03-17
[35]汤世江.一种高纯度1-脱氧野尻霉素的提取方法:中国,201310051701.3[P].2013-07-17
[36]李翠清,王腾,李继文,等.从桑叶中连续提取分离多糖及1-脱氧野尻霉素的方法:中国,201210462979.5[P].2013-03-13
[37]周长新,莫建霞,翁林佳,等.一种从桑叶中提取1-脱氧野尻霉素的方法:中国,200710067498.3[P].2007-08-22
[38]颜继忠,李行诺,雷伟.利用滤膜和树脂制备桑叶1-脱氧野尻霉素提取物的方法:中国,201210190238.6[P].2012-10-10
[39]朱元元,朱晓丹,白钢,等.桑枝皮中具有抑制α-糖苷酶活性的水溶性生物碱纯化方法及应用:中国,201210118472.8[P].2012-07-25
[40]张晓琦,叶葳,叶文才,等.具有α-糖苷酶抑制剂活性的中药提取物及其应用:中国,200710026300.7[P].2007-08-01
[41]欧阳臻,贾晓斌,李永辉,等.桑叶降血糖有效组分组合物及制备方法:中国,200610038713.2[P].2006-10-25
[42]罗蕾蕾,吴俊.桑叶中1-脱氧野尻霉素分离纯化的工艺研究[J].现代食品科技,2012,28(12):167-169
[43]吴方睿.桑叶中1-脱氧野尻霉素提取分离工艺研究[D].合肥:合肥工业大学,2009
[44]洪春力.一种含有桑叶总碱浸膏的制剂及其制备方法:中国,03101988.9[P].2003-07-23
[45]朱元元,白钢,亓晖.蚕沙总生物碱中的α-糖苷酶抑制剂化合物及其应用:中国,200910070770.2[P].2010-03-17
[46]常津,任晓文,魏民,等.天然絮凝剂对生脉饮提取液的精制研究[J].中国医药学报,1998,13(2),22-25
[47]刘茉娥.膜分离技术[M].北京:北京化学工业出版社,1998:1-2
[2]Nitra N,Kornkanok I,Wiroje K,et al.Quantitative determination of1-deoxynojirimycin in mulberry leaves using liquid chromatographytandem mass spectrometry[J].J Pharmaceut Biomed,2007,44(4):853-858
[3]Toshiyuki K,Kiyotaka N,Yuko S,et al.Determination of 1-deoxynojirimycin in mulberry leaves using hydrophilic interaction chromatography with evaporative light scattering detection[J].J Agric Food Chem,2004,52(6):1415-1418
[4]Kazuhisa Y,Masatoshi I,Satoshi O.The relationship between 1-deoxynojirimycin content andα-glucosidase inhibitory activity in leaves of 276 mulberry cultivars(Morus spp.)in Kyoto[J].Japan J Nat Med,2008,62(1):63-66
[5]Chaluntorn V,Kiyotaka N,Phumon S,et al.Development of high1-deoxynojirimycin(DNJ)content mulberry tea and use of response surface methodology to optimize tea-making conditions for highest DNJ extraction[J].LWT-Food Sci Technol,2012,45(2):226-232
[6]Kim H S,Kim Y H,Hong Y S,et al.α-Glucosidase inhibitors from Cornmelina communis[J].Planta Med,1999,65(5):437-439
[7]Asano N,Kato A,Miyanchi M,et al.Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientatis[J].J Nat Ptod,1998,61(5):625-628
[8]Asano N,Nishida M,Miyauchi M,et al.Polyhydroxylated pyrrolidine and piperidine alkaloids from Adenophora triphylla var.japonica(Campanulaceae)[J].Phytochemistry,2000,53(3):379-382
[9]Zhu Y P,Yamaki K,Yoshihashi T,et al.Purification and identification of 1-deoxynojirimycin(DNJ)in okara fermented by Bacillus subtilis B2 from chinese traditional food(meitaoza)[J].J Agric Food Chem,2010,58(7):4097-4103
[10]徐立,刘超,刘静,等.制备桑叶方便食品的调味料及其桑叶方便食品和制备方法:中国,201310293660.9[P].2013-09-25
[11]Michiru Y,Youichi T,Fumiko M,et al.Binding parameters and thermodynamics of the interaction of imino sugars with a recombinant human acidα-glucosidase(alglucosidase alfa):insight into the complex formation mechanism[J].Clin Chim Acta,2008,391(1/2):68-73
[12]Toshiyuki K,Kiyotaka N,Hiroyuki K,et al.Food-grade mulberry powder enriched with 1-deoxynojirimycin suppresses the elevation of postprandial blood glucose in humans[J].J Agric Food Chem,2007,55(14):5869-5874
[13]Tsuruok A T,Tamur A A,Matsuhashi Y,et al.Binding of D-methionine to peptidoglycan in the presence of inhibitors of cell wall synthesis in Escherichia coli[J].Agric Biol Chem,1985,49(8):2489-2490
[14]Eike S,Thomas W,Stephanie K.Antiviral effects of amantadine and iminosugar derivatives against hepatitis C virus[J].Hepatology,2007,46(2):330-338
[15]Fenouillet E,Papandréou M J,Jones I M.Recombinant HIV envelope expressed in anα-glucosidase I-deficient CHO cell line and its parental cell line in the presence of 1-deoxynojirimycin is functional[J].Virology,1997,231(1):89-95
[16]Kim J Y,Choi B G,Jung M J,et al.Mulberry leaf water extract ameliorates insulin sensitivity in high fator high sucrose diet induced overweight rats[J].J Korean Soc Appl Bi,2011,54(4):612-618
[17]杨青,郑晓瑞,陈红梅,等.1-脱氧野尻霉素衍生物的研究进展[J].中国生化药物杂志,2010,31(1):1-5
[18]陈燕军,冯青然.常用精制方法在纯化中药制剂中的应用[J].中国实验方剂学杂志,2003,9(3):56-60
[19]黄建,周玉飞,翟龙飞,等.1-脱氧野尻霉素晶体的制备及稳定性[J].应用化工,2012,41(12):2050-2056
[20]殷红.脱氧野尻霉素的一种纯化方法:中国,201110422786.2[P].2012-06-13
[21]黄建伟.桑叶中1-脱氧野尻霉素的制备方法:中国,201110021131.4[P].2011-08-17
[22]马全民,聂复礼,李雪斌,等.由桑叶中提取分离高纯度1-脱氧野尻霉素的方法:中国,201110038204.0[P].2011-06-22
[23]杨茹,卢朝华.天然产物中提取分离高纯1-脱氧野尻霉素的方法:中国,200910167602.5[P].2010-02-24
[24]孟夏.桑叶中1-脱氧野尻霉素的分离纯化技术研究[D].镇江:江苏大学,2008
[25]黄华学,唐方华,刘永胜.一种从桑叶中提取1-脱氧野尻霉素的方法:中国,201110087108.5[P].2011-09-21
[26]欧阳臻,孟夏,常钰,等.一种从桑叶总生物碱中分离1-脱氧野尻霉素单体的方法:中国,200810122998.7[P].2008-12-03
[27]向华.一种从桑叶提取1-脱氧野尻霉素和白藜芦醇的方法:中国,201110234164.7[P].2012-02-15
[28]唐忠梅.一种从植物中同时提取1-脱氧野尻霉素和白藜芦醇的方法:中国,201210162994.8[P].2012-10-17
[29]冯旭东,刘明明,路娟,等.等电点-冷却结晶去除谷氨酸中的焦谷氨酸[J].食品科学,2013,34(20):19-22
[30]叶青,裘兆蓉,韶晖,等.用降膜结晶法分离人造麝香的研究[J].化工进展,2004,23(11):1233-1235
[31]张世文,姚祖凤.萃取-结晶法制备高纯辣椒碱类化合物[J].吉首大学学报:自然科学版,2002,2(2):90-92
[32]艾秀珍,沈波,危凤,等.萃取-结晶法制备辣椒碱类化合物工艺研究[J].天然产物研究与开发,2008(20):150-153
[33]李宇亮,李剑敏,吴雅睿.1-脱氧野尻霉素提取分离方法研究[J].应用化工.2006,35(9):659-665
[34]杭伟锋,鲍玲,刘刚,等.一种从桑叶中连续提取分离1-脱氧野尻霉素(DNJ)、黄酮的方法:中国,200910192542.2[P].2010-03-17
[35]汤世江.一种高纯度1-脱氧野尻霉素的提取方法:中国,201310051701.3[P].2013-07-17
[36]李翠清,王腾,李继文,等.从桑叶中连续提取分离多糖及1-脱氧野尻霉素的方法:中国,201210462979.5[P].2013-03-13
[37]周长新,莫建霞,翁林佳,等.一种从桑叶中提取1-脱氧野尻霉素的方法:中国,200710067498.3[P].2007-08-22
[38]颜继忠,李行诺,雷伟.利用滤膜和树脂制备桑叶1-脱氧野尻霉素提取物的方法:中国,201210190238.6[P].2012-10-10
[39]朱元元,朱晓丹,白钢,等.桑枝皮中具有抑制α-糖苷酶活性的水溶性生物碱纯化方法及应用:中国,201210118472.8[P].2012-07-25
[40]张晓琦,叶葳,叶文才,等.具有α-糖苷酶抑制剂活性的中药提取物及其应用:中国,200710026300.7[P].2007-08-01
[41]欧阳臻,贾晓斌,李永辉,等.桑叶降血糖有效组分组合物及制备方法:中国,200610038713.2[P].2006-10-25
[42]罗蕾蕾,吴俊.桑叶中1-脱氧野尻霉素分离纯化的工艺研究[J].现代食品科技,2012,28(12):167-169
[43]吴方睿.桑叶中1-脱氧野尻霉素提取分离工艺研究[D].合肥:合肥工业大学,2009
[44]洪春力.一种含有桑叶总碱浸膏的制剂及其制备方法:中国,03101988.9[P].2003-07-23
[45]朱元元,白钢,亓晖.蚕沙总生物碱中的α-糖苷酶抑制剂化合物及其应用:中国,200910070770.2[P].2010-03-17
[46]常津,任晓文,魏民,等.天然絮凝剂对生脉饮提取液的精制研究[J].中国医药学报,1998,13(2),22-25
[47]刘茉娥.膜分离技术[M].北京:北京化学工业出版社,1998:1-2