黄酮类化合物的生物转化研究进展
|
摘要
黄酮类化合物广泛存在于高等植物及蕨类植物中,以黄酮醇和黄酮最为常见,具有抗氧化、抗炎、抗菌、抗肿瘤及降血糖等多种生理活性.芸香苷、橙皮苷、儿茶素、水飞蓟素、黄芩苷等多种黄酮类药物已应用于临床.但部分黄酮类成分溶解性较差、生物利用度低,因此对黄酮类化合物的结构修饰已成为研究的热点.生物转化拥有反应条件温和、高效、环保及立体选择性强等优势,在天然产物的结构修饰中应用越来越广泛.文章分别综述了微生物转化及以植物细胞为载体的生物转化在黄酮中的应用,以期为黄酮类化合物的进一步研究提供参考.
Flavonoids exist widely in higher plants and ferns,with flavonols and flavones as the most common types,which have many physiological activities of being antioxidant,anti-inflammatory,antibacterial,antitumor and hypoglycemic. Rutin,hesperidin,catechin,silymarin,baicalin and other flavonoids have been applied in clinic. However,some flavonoids have poor solubility and low bioavailability. Therefore,the structural modification of flavonoids has become a research hotspot. Biotransformation,which has been widely used in the structure modification of natural products,has the advantages of mild reaction conditions,high efficiency,environmental protection,and strong stereoselectivity. The application of microbial transformation and the biotransformation that takes plant cells as the carrier to flavonoids is reviewed in this paper,with a view to providing a reference for further research of flavonoids.
Flavonoids exist widely in higher plants and ferns,with flavonols and flavones as the most common types,which have many physiological activities of being antioxidant,anti-inflammatory,antibacterial,antitumor and hypoglycemic. Rutin,hesperidin,catechin,silymarin,baicalin and other flavonoids have been applied in clinic. However,some flavonoids have poor solubility and low bioavailability. Therefore,the structural modification of flavonoids has become a research hotspot. Biotransformation,which has been widely used in the structure modification of natural products,has the advantages of mild reaction conditions,high efficiency,environmental protection,and strong stereoselectivity. The application of microbial transformation and the biotransformation that takes plant cells as the carrier to flavonoids is reviewed in this paper,with a view to providing a reference for further research of flavonoids.
引文
[1]唐浩国.黄酮类化合物研究[M].北京:科学出版社,2009.
[2]李丹,肖刚,丁霄霖.苦荞黄酮抗氧化作用的研究[J].食品科学,2001,22(4):22-24.
[3]Escriche I,Kadar M,Juan-Borrás M,et al.Suitability of antioxidant capacity,flavonoids and phenolic acids for floral authentication of honey.Impact of industrial thermal treatment[J].Food Chemistry,2014,142(2):135-143.
[4]杨杰,沙金丹,高翔,等.黄酮类化合物的免疫调节作用及机制[J].动物营养学报,2017,29(12):4295-4300.
[5]吴涛.芦丁抗疲劳作用的实验研究[D].陕西师范大学,2013.
[6]韩敏.黄酮类化合物降血脂作用研究进展[J].西安文理学院学报(自然科学版),2013,16(4):11-15.
[7]谢鹏,张敏红.黄酮类化合物抑菌作用的研究进展[J].中国动物保健,2004(12):35-37.
[8]朱会平.黄酮类化合物促进癌细胞凋亡的分子机理研究进展[J].生物技术通讯,2006,17(3):455-456.
[9]Li H,Deng Z,Liu R,et al.Bioaccessibility,in vitro antioxidant activities and in vivo anti-inflammatory activities of a purple tomato(Solanum lycopersicum L.)[J].Food Chemistry,2014,159(11):353.
[10]Xiao J,H9gger P.Influence of diabetes on the pharmacokinetic behavior of natural polyphenols[J].Current Drug Metabolism.2014,15(1):23-29.
[11]赵雪巍,刘培玉,刘丹,等.黄酮类化合物的构效关系研究进展[J].中草药,2015,46(21):3264-3271.
[12]赖剑峰,杨荣玲,刘学铭.黄酮类化合物的生物转化研究进展[J].广东农业科学,2013,40(4):95-98.
[13]崔莉,孙娥,陈玲玲,等.生物转化在黄酮类化合物中的研究与应用[J].中华中医药杂志,2013(3):764-767.
[14]赵宏,缪月英,张义秀,等.黄酮类化合物生物转化的研究进展[J].科学技术创新,2013(9):55.
[15]Seleem D,Pardi V,Murata R M.Review of flavonoids:A diverse group of natural compounds with anti-Candida albicans activity in vitro[J].Archives of Oral Biology,2017,76:76-83.
[16]周珮.生物技术制药[M].北京:人民卫生出版社,2007.
[17]Loughlin W A.Biotransformations in organic synthesis[J].Bioresource Technology,2000,74(1):49-62.
[18]赵雪巍,刘培玉,刘丹,等.黄酮类化合物的构效关系研究进展[J].中草药,2015,46(21):3264-3271.
[19]扈飞凡.植物生物转化技术在生物药物中的应用[J].赤峰学院学报,2008,(6):21-23.
[20]牛红军,王芃,杨官娥.微生物转化技术在中药研究中的应用[J].中国实验方剂学杂志,2013,19(18):346-349.
[21]Sordon S,Madej A,Popoński J,et al.Regioselective ortho-Hydroxylations of Flavonoids by Yeast[J].Journal of Agricultural&Food Chemistry,2016,64(27):5525.
[22]Luo J,Liang Q,Shen Y,et al.Biotransformation of bavachinin by three fungal cell cultures[J].Journal of Bioscience&Bioengineering,2013,117(2):191-196.
[23]王敏,骆健美,申雁冰,等.一种补骨脂二氢黄酮甲醚羟基化衍生物及合成方法:CN 103724309 A[P].2014-04-16.
[24]Tronina T,Bartmańska A,Popoński J,et al.Transformation of xanthohumol by Aspergillus ochraceus[J].Journal of Basic Microbiology,2014,54(1):66-71.
[25]邬建国.槐角异黄酮生物转化及其产物抗乳腺癌细胞活性研究[D].华中科技大学2011年博士学位论文.
[26]井乐刚,张永忠.微生物发酵制备大豆异黄酮的研究进展[J].微生物学通报,2003,30(2):86-88.
[27]马达.大豆异黄酮的生物转化和体外雌激素活性[D].大连轻工业学院2006年硕士学位论文.
[28]Xiao X,Si X,Xing T,et al.Preparation of flavonoids and diarylheptanoid from Alpinia katsumadai hayata,by microwave-assisted extraction and high-speed counter-current chromatography[J].Separation&Purification Technology,2011,81(3):265-269.
[29]周天,李崎.酒花中的黄腐酚及其他含异戊二烯基类黄酮[J].酿酒科技,2006(8):45-47.
[30]傅明亮.生物催化异黄腐酚合成8-异戊烯基柚皮素研究[D].浙江大学2012年硕士学位论文.
[31]高霞,陈彦,王莹,等.淫羊藿总黄酮的生物转化过程分析[J].中国中药杂志,2013,38(23):4079.
[32]Luo C F,Yuan M,Chen M S,et al.Pharmacokinetics,tissue distribution and relative bioavailability of puerarin solid lipid nanoparticles following oral administration[J].International Journal of Pharmaceutics,2011,410(1-2):138.
[33]Ye H,Yuan S,Cong X D.Biotransformation of puerarin into 3'-hydroxypuerarin by Trichoderma harzianum NJ01[J].Enzyme and Microbial Technology,2007,40:594-597.
[34]Teresa V,Alba R N,Francesca A,et al.Flavonoids in inflammatory bowel disease:a review[J].Nutrients,2016,8(4):211.
[35]Saleh N A M,Bohm B A,Ornduff R.Flavonoids of Lasthenia conjugens,and Lasthenia fremontii[J].Phytochemistry,2016,10(3):611-614.
[36]Em D M B C,Pimenta F C,Luz W C,et al.Selection of filamentous fungi of the Beauveria genus able to metabolize quercetin like mammalian cells[J].Brazilian Journal of Microbiology,2008,39(2):405.
[37]Ping L,Zheng Y A,Wang Y S,et al.Bioconversion of flavonoidal glycosides in the leaves of hippophae rhamnoides into aglycones[J].Journal of Chemical Engineering of Chinese Universities,2006,20(6):996-1000.
[38]吴鹏,郭峰,陈龙,等.银杏叶黄酮的酶法提取及生物转化研究[J].特产研究,2007,29(4):22-24.
[39]王智磊,刘素娟,张鑫,等.黑曲霉生物转化黄酮类成分研究进展[J].中国实验方剂学杂志,2017,38(21):220-228.
[40]姚轶俊,王立峰,鞠兴荣.纤维素载体固定化β-葡萄糖苷酶及其在大豆异黄酮水解中的应用[J].食品科学,2017,38(24):177-182.
[41]Duarte P,Ribeiro D,Carqueijeiro I,et al.Protoplast transformation as a plant-transferable transient expression system[J].methods in molecular biology,2016,1405:137.
[42]Byrappa K,Ohara S,Adschiri T.Nanoparticles synthesis using supercritical fluid technology-towards biomedical applications[J].Adv Drug Deliv Rev,2008,60(3):299-327.
[43]Shuler M L,Hallsby G A,Pyne J W,et al.Bioreactors for immobilized plant cell culturesa[J].Annals of the New York Academy of Sciences,2010,469(1):270-278.
[44]刘岱琳,隋玉辉,臧志和.萜类化合物及其皂苷生物转化的研究进展[J].武警医学,2007,18(3):221-224.
[45]尹云泽,陈日道,王春梅,等.植物悬浮细胞对黄酮类化合物的异戊烯基化[A].中国药学大会暨中国药师周论文集[C].2011:1.
[2]李丹,肖刚,丁霄霖.苦荞黄酮抗氧化作用的研究[J].食品科学,2001,22(4):22-24.
[3]Escriche I,Kadar M,Juan-Borrás M,et al.Suitability of antioxidant capacity,flavonoids and phenolic acids for floral authentication of honey.Impact of industrial thermal treatment[J].Food Chemistry,2014,142(2):135-143.
[4]杨杰,沙金丹,高翔,等.黄酮类化合物的免疫调节作用及机制[J].动物营养学报,2017,29(12):4295-4300.
[5]吴涛.芦丁抗疲劳作用的实验研究[D].陕西师范大学,2013.
[6]韩敏.黄酮类化合物降血脂作用研究进展[J].西安文理学院学报(自然科学版),2013,16(4):11-15.
[7]谢鹏,张敏红.黄酮类化合物抑菌作用的研究进展[J].中国动物保健,2004(12):35-37.
[8]朱会平.黄酮类化合物促进癌细胞凋亡的分子机理研究进展[J].生物技术通讯,2006,17(3):455-456.
[9]Li H,Deng Z,Liu R,et al.Bioaccessibility,in vitro antioxidant activities and in vivo anti-inflammatory activities of a purple tomato(Solanum lycopersicum L.)[J].Food Chemistry,2014,159(11):353.
[10]Xiao J,H9gger P.Influence of diabetes on the pharmacokinetic behavior of natural polyphenols[J].Current Drug Metabolism.2014,15(1):23-29.
[11]赵雪巍,刘培玉,刘丹,等.黄酮类化合物的构效关系研究进展[J].中草药,2015,46(21):3264-3271.
[12]赖剑峰,杨荣玲,刘学铭.黄酮类化合物的生物转化研究进展[J].广东农业科学,2013,40(4):95-98.
[13]崔莉,孙娥,陈玲玲,等.生物转化在黄酮类化合物中的研究与应用[J].中华中医药杂志,2013(3):764-767.
[14]赵宏,缪月英,张义秀,等.黄酮类化合物生物转化的研究进展[J].科学技术创新,2013(9):55.
[15]Seleem D,Pardi V,Murata R M.Review of flavonoids:A diverse group of natural compounds with anti-Candida albicans activity in vitro[J].Archives of Oral Biology,2017,76:76-83.
[16]周珮.生物技术制药[M].北京:人民卫生出版社,2007.
[17]Loughlin W A.Biotransformations in organic synthesis[J].Bioresource Technology,2000,74(1):49-62.
[18]赵雪巍,刘培玉,刘丹,等.黄酮类化合物的构效关系研究进展[J].中草药,2015,46(21):3264-3271.
[19]扈飞凡.植物生物转化技术在生物药物中的应用[J].赤峰学院学报,2008,(6):21-23.
[20]牛红军,王芃,杨官娥.微生物转化技术在中药研究中的应用[J].中国实验方剂学杂志,2013,19(18):346-349.
[21]Sordon S,Madej A,Popoński J,et al.Regioselective ortho-Hydroxylations of Flavonoids by Yeast[J].Journal of Agricultural&Food Chemistry,2016,64(27):5525.
[22]Luo J,Liang Q,Shen Y,et al.Biotransformation of bavachinin by three fungal cell cultures[J].Journal of Bioscience&Bioengineering,2013,117(2):191-196.
[23]王敏,骆健美,申雁冰,等.一种补骨脂二氢黄酮甲醚羟基化衍生物及合成方法:CN 103724309 A[P].2014-04-16.
[24]Tronina T,Bartmańska A,Popoński J,et al.Transformation of xanthohumol by Aspergillus ochraceus[J].Journal of Basic Microbiology,2014,54(1):66-71.
[25]邬建国.槐角异黄酮生物转化及其产物抗乳腺癌细胞活性研究[D].华中科技大学2011年博士学位论文.
[26]井乐刚,张永忠.微生物发酵制备大豆异黄酮的研究进展[J].微生物学通报,2003,30(2):86-88.
[27]马达.大豆异黄酮的生物转化和体外雌激素活性[D].大连轻工业学院2006年硕士学位论文.
[28]Xiao X,Si X,Xing T,et al.Preparation of flavonoids and diarylheptanoid from Alpinia katsumadai hayata,by microwave-assisted extraction and high-speed counter-current chromatography[J].Separation&Purification Technology,2011,81(3):265-269.
[29]周天,李崎.酒花中的黄腐酚及其他含异戊二烯基类黄酮[J].酿酒科技,2006(8):45-47.
[30]傅明亮.生物催化异黄腐酚合成8-异戊烯基柚皮素研究[D].浙江大学2012年硕士学位论文.
[31]高霞,陈彦,王莹,等.淫羊藿总黄酮的生物转化过程分析[J].中国中药杂志,2013,38(23):4079.
[32]Luo C F,Yuan M,Chen M S,et al.Pharmacokinetics,tissue distribution and relative bioavailability of puerarin solid lipid nanoparticles following oral administration[J].International Journal of Pharmaceutics,2011,410(1-2):138.
[33]Ye H,Yuan S,Cong X D.Biotransformation of puerarin into 3'-hydroxypuerarin by Trichoderma harzianum NJ01[J].Enzyme and Microbial Technology,2007,40:594-597.
[34]Teresa V,Alba R N,Francesca A,et al.Flavonoids in inflammatory bowel disease:a review[J].Nutrients,2016,8(4):211.
[35]Saleh N A M,Bohm B A,Ornduff R.Flavonoids of Lasthenia conjugens,and Lasthenia fremontii[J].Phytochemistry,2016,10(3):611-614.
[36]Em D M B C,Pimenta F C,Luz W C,et al.Selection of filamentous fungi of the Beauveria genus able to metabolize quercetin like mammalian cells[J].Brazilian Journal of Microbiology,2008,39(2):405.
[37]Ping L,Zheng Y A,Wang Y S,et al.Bioconversion of flavonoidal glycosides in the leaves of hippophae rhamnoides into aglycones[J].Journal of Chemical Engineering of Chinese Universities,2006,20(6):996-1000.
[38]吴鹏,郭峰,陈龙,等.银杏叶黄酮的酶法提取及生物转化研究[J].特产研究,2007,29(4):22-24.
[39]王智磊,刘素娟,张鑫,等.黑曲霉生物转化黄酮类成分研究进展[J].中国实验方剂学杂志,2017,38(21):220-228.
[40]姚轶俊,王立峰,鞠兴荣.纤维素载体固定化β-葡萄糖苷酶及其在大豆异黄酮水解中的应用[J].食品科学,2017,38(24):177-182.
[41]Duarte P,Ribeiro D,Carqueijeiro I,et al.Protoplast transformation as a plant-transferable transient expression system[J].methods in molecular biology,2016,1405:137.
[42]Byrappa K,Ohara S,Adschiri T.Nanoparticles synthesis using supercritical fluid technology-towards biomedical applications[J].Adv Drug Deliv Rev,2008,60(3):299-327.
[43]Shuler M L,Hallsby G A,Pyne J W,et al.Bioreactors for immobilized plant cell culturesa[J].Annals of the New York Academy of Sciences,2010,469(1):270-278.
[44]刘岱琳,隋玉辉,臧志和.萜类化合物及其皂苷生物转化的研究进展[J].武警医学,2007,18(3):221-224.
[45]尹云泽,陈日道,王春梅,等.植物悬浮细胞对黄酮类化合物的异戊烯基化[A].中国药学大会暨中国药师周论文集[C].2011:1.