咪唑类离子液体在天然产物黄酮类成分提取中的应用
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摘要
黄酮类化合物具有多方面的生理和药理活性,而离子液体因其独特的性质在天然产物黄酮类成分的提取中应用越来越多。综述了目前天然产物中黄酮类成分的提取方法,以及离子液体特别是咪唑类离子液体的阴阳离子类型、碳链长度、键合作用等对天然黄酮类化合物提取的影响规律,提出了应用于黄酮类化合物离子液体萃取剂选择的建议,并指出离子液体的绿色回收和可食用型离子液体的开发是未来的发展方向,为离子液体在天然黄酮类成分开发中的基础研究和工业应用奠定基础。
Flavonoids have many physiological and pharmacological activities. Ionic liquids are increasingly used in the extraction of flavonoids from natural products due to their unique properties. In this paper, various extraction methods of natural flavonoids were reviewed and summarized. The effects of anion and cation type, length of carbon chain, and bond cooperation on the extraction of natural flavonoids in ionic liquids, especially imidazole type ionic liquids, were also reviewed. Suggestions on selection of extractant for ionic liquid extraction of flavonoids were given. The advice of the green recovery of ionic liquids and the development of edible ionic liquids for the future direction of development were suggested. This study will lay the foundation for the basic research and industrial application of ionic liquids in the extraction of natural flavonoids.
Flavonoids have many physiological and pharmacological activities. Ionic liquids are increasingly used in the extraction of flavonoids from natural products due to their unique properties. In this paper, various extraction methods of natural flavonoids were reviewed and summarized. The effects of anion and cation type, length of carbon chain, and bond cooperation on the extraction of natural flavonoids in ionic liquids, especially imidazole type ionic liquids, were also reviewed. Suggestions on selection of extractant for ionic liquid extraction of flavonoids were given. The advice of the green recovery of ionic liquids and the development of edible ionic liquids for the future direction of development were suggested. This study will lay the foundation for the basic research and industrial application of ionic liquids in the extraction of natural flavonoids.
引文
[1]刘璐,付明哲,王侠,等.植物黄酮类化合物提取及测定方法研究进展[J].动物医学进展,2011,32(6):151-155.
[2]刘洋,金玉姬,吴湘军,等.甘草黄酮的研究现状及进展[J].吉林医药学院学报,2014,35(2):135-139.
[3]张永红,李艳.银杏叶黄酮类化合物提取方法探讨[J].实用中医药杂志,2007,23(6):397-398.
[4]张百霞,周凤琴,郭庆梅.金银花中黄酮类化合物的研究进展[J].中国实验方剂学杂志,2012,18(23):349-352.
[5]高靖,陈继红.葛根及葛根异黄酮的研究现状[J].畜牧与饲料科学,2013,34(6):44-45.
[6]曹秦,吴辉,张蓓蓓,等.黄酮类化合物在防治神经退行性疾病中作用的研究进展[J].中国药理学与毒理学杂志,2015,29(3):457-463.
[7]孙晓润,陈苹苹,林悦,等.天然黄酮类化合物抗肿瘤作用靶点研究进展[J].中国实验方剂学杂志,2017,23(6):218-228.
[8]苏艳杰,陈亚辉,崔燎.植物黄酮抗骨质疏松作用研究进展[J].中国骨质疏松杂志,2014,20(5):562-568.
[9]俞文英,张欢欢,吴月国,等.黄酮类化合物的构效关系及其在肺部炎症疾病中的应用[J].中草药,2018,49(20):4912-4918.
[10]方一杰,徐岩成,安毛毛,等.黄酮类化合物的药动学和药理作用研究进展[J].药学服务与研究,2015,15(1):6-9.
[11]徐学君,张秀芳,徐德琴,等.黄酮类化合物调节血脂作用的研究进展[J].中国药房,2016,27(1):114-117.
[12]Lin Z,Ravipati A S,Koyyalamudi S R,et al.Antioxidant and anti-inflammatory activities of selected medicinal plants containing phenolic and flavonoid compounds[J].J Agric Food Chem,2011,59(23):12361-12367.
[13]Nagaraja Y P,Krishna V.Hepatoprotective effect of the aqueous extract and 5-hydroxy,7,8,2′-trimethoxyflavone of Andrographis alata Nees.in carbon tetrachloride treated rats[J].Achiev Life Sci,2016,5(2):5-10.
[14]Wang W,Li Q,Liu Y,et al.Ionic liquid-aqueous solution ultrasonic-assisted extraction of three kinds of alkaloids from Phellodendron amurense Rupr and optimize conditions use response surface[J].Ultrason Sonochem,2014,24(5):13-18.
[15]Severa G,Edwards M,Cooney M J.Bio-oil extraction of Jatropha curcas with ionic liquid co-solvent:Fate of biomass protein[J].Biores Technol,2017,226(2):255-261.
[16]赵子龙,薛培凤,倪佩东,等.天然药物中总黄酮的提取工艺研究进展[J].内蒙古医学院学报,2012,34(6):512-516.
[17]吉惠杰,薛俊礼,程振玉,等.仙人草总黄酮提取工艺及抗氧化活性研究[J].河南工业大学学报:自然科学版,2016,37(6):62-66.
[18]陈建平,罗素琴,王金辉,等.中蒙药黄酮的提取方法研究进展[J].内蒙古医学院学报,2012,34(5):417-422.
[19]张艳,张传智,徐淼,等.微波辅助法提取紫苏油粕黄酮工艺及其抗氧化性的研究[J].粮油食品科技,2017,25(6):21-25.
[20]王海燕,赵晓宇,王继双,等.“药食同源”植物葛根中总黄酮提取方法的研究进展[J].食品安全质量检测学报,2017,8(10):3931-3934.
[21]焦岩,常影,刘井权.沙棘黄酮提取与分离技术研究综述[J].食品工业,2012,33(8):115-118.
[22]卢丞文,王玲.大豆异黄酮提取方法的研究进展[J].吉林农业,2017(15):111.
[23]谯康全,郑兴文,刘新露.竹叶总黄酮微波-超声协同提取工艺研究[J].安徽农业科学,2011,39(30):18516-18517.
[24]Passos H,Freire M G,Coutinho J A P.Ionic liquid solutions as extractive solvents for value-added compounds from biomass[J].Green Chem,2014,16(12):4786-4815.
[25]Wang Y Y,Zhang L H,Wang D D,et al.Room temperature ionic liquids-based salting-in strategy for counter-current chromatography in the separation of arctiin[J].J Chromatogr A,2016,1478(12):26-34.
[26]冯纪南,冯斯宇,邓斌.离子液体微波辅助提取臭牡丹中黄酮类化合物的研究[J].商丘师范学院学报,2015,31(3):51-55.
[27]杜芳艳,邓保炜,高立国,等.离子液体/微波萃取海红果渣中总黄酮工艺[J].光谱实验室,2013,30(5):2231-2234.
[28]李倩.离子液体微波辅助提取葛根总黄酮及纯化的研究[D].武汉:武汉工程大学,2012.
[29]陈君,周光明,杨远高,等.离子液体-超声辅助提取/高效液相色谱法测定白花杜鹃叶中的黄酮[J].分析测试学报,2013,32(3):341-345.
[30]陈君,周光明,杨远高,等.离子液体-超声辅助萃取-高效液相色谱测定桑叶中黄酮[J].食品科学,2012,33(24):215-218.
[31]Zeng H,Wang Y,Kong J,et al.Ionic liquid-based microwave-assisted extraction of rutin from Chinese medicinal plants[J].Talanta,2010,83(2):582-590.
[32]曾欢.中草药中活性成分芦丁的分离分析方法研究与应用[D].长沙:湖南大学,2011.
[33]王阳光,欧阳小琨,杨立业,等.离子液体微波辅助萃取柽柳中芦丁的研究[J].高校化学工程学报,2011,25(3):411-415.
[34]Du F Y,Xiao X H,Luo X J,et al.Application of ionic liquids in the microwave-assisted extraction of polyphenolic compounds from medicinal plants[J].Talanta,2009,78(3):1177-1184.
[35]Xu W,Chu K,Li H,et al.Ionic liquid-based microwave-assisted extraction of flavonoids from Bauhinia championii(Benth.)[J].Molecules,2012,17(12):14323-14335.
[36]郭燕燕,尹卫平,刘普,等.离子液体提取分离鹿藿中异黄酮化合物[J].应用化学,2011,28(5):537-541.
[37]李雪琴,郭瑞丽.疏水性离子液体萃取光甘草定[J].化学研究与应用,2013,25(2):169-173.
[38]李晓月,郭瑞丽,张建树.碱性离子液体萃取光甘草定的研究[J].石河子大学学报:自然科学版,2015,33(2):145-148.
[39]黄好.离子液体对几种天然活性物质的萃取分离[D].南宁:广西大学,2016.
[40]Chowdhury S A,Vijayarhavan R,Macfarlane D R.Distillable ionic liquid extraction of tannins from plant materials[J].Green Chem,2010,12(6):1023-1028.
[41]李敏,王秀玲,王力川,等.微波辅助离子液体提取酸枣仁中黄酮的研究[J].安徽农业科学,2015,43(27):225-227.
[42]曾珊.微波辅助离子液体提取黄酮类化合物的研究[D].湘潭:湘潭大学,2016.
[43]秦红英,周光明,彭贵龙,等.离子液体超声辅助萃取HPLC法测定天山雪莲中的4个有效成分[J].药物分析杂志,2014,34(5):844-847.
[44]Sun Y,Li W,Wang J.Ionic liquid based ultrasonic assisted extraction of isoflavones from Iris tectorumMaxim and subsequently separation and purification by high-speed counter-current chromatography[J].J Chromaogr B,2011,879(13/14):975-980.
[45]杨启炜.离子液体为介质萃取分离天然活性同系物[D].杭州:浙江大学,2010.
[2]刘洋,金玉姬,吴湘军,等.甘草黄酮的研究现状及进展[J].吉林医药学院学报,2014,35(2):135-139.
[3]张永红,李艳.银杏叶黄酮类化合物提取方法探讨[J].实用中医药杂志,2007,23(6):397-398.
[4]张百霞,周凤琴,郭庆梅.金银花中黄酮类化合物的研究进展[J].中国实验方剂学杂志,2012,18(23):349-352.
[5]高靖,陈继红.葛根及葛根异黄酮的研究现状[J].畜牧与饲料科学,2013,34(6):44-45.
[6]曹秦,吴辉,张蓓蓓,等.黄酮类化合物在防治神经退行性疾病中作用的研究进展[J].中国药理学与毒理学杂志,2015,29(3):457-463.
[7]孙晓润,陈苹苹,林悦,等.天然黄酮类化合物抗肿瘤作用靶点研究进展[J].中国实验方剂学杂志,2017,23(6):218-228.
[8]苏艳杰,陈亚辉,崔燎.植物黄酮抗骨质疏松作用研究进展[J].中国骨质疏松杂志,2014,20(5):562-568.
[9]俞文英,张欢欢,吴月国,等.黄酮类化合物的构效关系及其在肺部炎症疾病中的应用[J].中草药,2018,49(20):4912-4918.
[10]方一杰,徐岩成,安毛毛,等.黄酮类化合物的药动学和药理作用研究进展[J].药学服务与研究,2015,15(1):6-9.
[11]徐学君,张秀芳,徐德琴,等.黄酮类化合物调节血脂作用的研究进展[J].中国药房,2016,27(1):114-117.
[12]Lin Z,Ravipati A S,Koyyalamudi S R,et al.Antioxidant and anti-inflammatory activities of selected medicinal plants containing phenolic and flavonoid compounds[J].J Agric Food Chem,2011,59(23):12361-12367.
[13]Nagaraja Y P,Krishna V.Hepatoprotective effect of the aqueous extract and 5-hydroxy,7,8,2′-trimethoxyflavone of Andrographis alata Nees.in carbon tetrachloride treated rats[J].Achiev Life Sci,2016,5(2):5-10.
[14]Wang W,Li Q,Liu Y,et al.Ionic liquid-aqueous solution ultrasonic-assisted extraction of three kinds of alkaloids from Phellodendron amurense Rupr and optimize conditions use response surface[J].Ultrason Sonochem,2014,24(5):13-18.
[15]Severa G,Edwards M,Cooney M J.Bio-oil extraction of Jatropha curcas with ionic liquid co-solvent:Fate of biomass protein[J].Biores Technol,2017,226(2):255-261.
[16]赵子龙,薛培凤,倪佩东,等.天然药物中总黄酮的提取工艺研究进展[J].内蒙古医学院学报,2012,34(6):512-516.
[17]吉惠杰,薛俊礼,程振玉,等.仙人草总黄酮提取工艺及抗氧化活性研究[J].河南工业大学学报:自然科学版,2016,37(6):62-66.
[18]陈建平,罗素琴,王金辉,等.中蒙药黄酮的提取方法研究进展[J].内蒙古医学院学报,2012,34(5):417-422.
[19]张艳,张传智,徐淼,等.微波辅助法提取紫苏油粕黄酮工艺及其抗氧化性的研究[J].粮油食品科技,2017,25(6):21-25.
[20]王海燕,赵晓宇,王继双,等.“药食同源”植物葛根中总黄酮提取方法的研究进展[J].食品安全质量检测学报,2017,8(10):3931-3934.
[21]焦岩,常影,刘井权.沙棘黄酮提取与分离技术研究综述[J].食品工业,2012,33(8):115-118.
[22]卢丞文,王玲.大豆异黄酮提取方法的研究进展[J].吉林农业,2017(15):111.
[23]谯康全,郑兴文,刘新露.竹叶总黄酮微波-超声协同提取工艺研究[J].安徽农业科学,2011,39(30):18516-18517.
[24]Passos H,Freire M G,Coutinho J A P.Ionic liquid solutions as extractive solvents for value-added compounds from biomass[J].Green Chem,2014,16(12):4786-4815.
[25]Wang Y Y,Zhang L H,Wang D D,et al.Room temperature ionic liquids-based salting-in strategy for counter-current chromatography in the separation of arctiin[J].J Chromatogr A,2016,1478(12):26-34.
[26]冯纪南,冯斯宇,邓斌.离子液体微波辅助提取臭牡丹中黄酮类化合物的研究[J].商丘师范学院学报,2015,31(3):51-55.
[27]杜芳艳,邓保炜,高立国,等.离子液体/微波萃取海红果渣中总黄酮工艺[J].光谱实验室,2013,30(5):2231-2234.
[28]李倩.离子液体微波辅助提取葛根总黄酮及纯化的研究[D].武汉:武汉工程大学,2012.
[29]陈君,周光明,杨远高,等.离子液体-超声辅助提取/高效液相色谱法测定白花杜鹃叶中的黄酮[J].分析测试学报,2013,32(3):341-345.
[30]陈君,周光明,杨远高,等.离子液体-超声辅助萃取-高效液相色谱测定桑叶中黄酮[J].食品科学,2012,33(24):215-218.
[31]Zeng H,Wang Y,Kong J,et al.Ionic liquid-based microwave-assisted extraction of rutin from Chinese medicinal plants[J].Talanta,2010,83(2):582-590.
[32]曾欢.中草药中活性成分芦丁的分离分析方法研究与应用[D].长沙:湖南大学,2011.
[33]王阳光,欧阳小琨,杨立业,等.离子液体微波辅助萃取柽柳中芦丁的研究[J].高校化学工程学报,2011,25(3):411-415.
[34]Du F Y,Xiao X H,Luo X J,et al.Application of ionic liquids in the microwave-assisted extraction of polyphenolic compounds from medicinal plants[J].Talanta,2009,78(3):1177-1184.
[35]Xu W,Chu K,Li H,et al.Ionic liquid-based microwave-assisted extraction of flavonoids from Bauhinia championii(Benth.)[J].Molecules,2012,17(12):14323-14335.
[36]郭燕燕,尹卫平,刘普,等.离子液体提取分离鹿藿中异黄酮化合物[J].应用化学,2011,28(5):537-541.
[37]李雪琴,郭瑞丽.疏水性离子液体萃取光甘草定[J].化学研究与应用,2013,25(2):169-173.
[38]李晓月,郭瑞丽,张建树.碱性离子液体萃取光甘草定的研究[J].石河子大学学报:自然科学版,2015,33(2):145-148.
[39]黄好.离子液体对几种天然活性物质的萃取分离[D].南宁:广西大学,2016.
[40]Chowdhury S A,Vijayarhavan R,Macfarlane D R.Distillable ionic liquid extraction of tannins from plant materials[J].Green Chem,2010,12(6):1023-1028.
[41]李敏,王秀玲,王力川,等.微波辅助离子液体提取酸枣仁中黄酮的研究[J].安徽农业科学,2015,43(27):225-227.
[42]曾珊.微波辅助离子液体提取黄酮类化合物的研究[D].湘潭:湘潭大学,2016.
[43]秦红英,周光明,彭贵龙,等.离子液体超声辅助萃取HPLC法测定天山雪莲中的4个有效成分[J].药物分析杂志,2014,34(5):844-847.
[44]Sun Y,Li W,Wang J.Ionic liquid based ultrasonic assisted extraction of isoflavones from Iris tectorumMaxim and subsequently separation and purification by high-speed counter-current chromatography[J].J Chromaogr B,2011,879(13/14):975-980.
[45]杨启炜.离子液体为介质萃取分离天然活性同系物[D].杭州:浙江大学,2010.