综述与专题评论

根皮素的制备、结构修饰及生理活性研究进展

  • 魏丽娜 ,
  • 赵静 ,
  • 罗仓学 ,
  • 刘娟 ,
  • 史长政
展开
  • (陕西科技大学 食品与生物工程学院,陕西 西安, 710021)
魏丽娜讲师,博士和赵静硕士研究生为共同第一作者,(魏丽娜讲师为通讯作者,E-mail:weilina_sust@163.com)。

收稿日期: 2019-01-25

  网络出版日期: 2019-10-24

基金资助

国家自然科学基金(NSFC)项目(31701562);陕西省重点研究开发项目(2017TSCXL-NY-02-03);陕西科技大学博士科研启动基金项目(2016BJ-27)

Preparation, structural modification and physiological activities ofphloretin: a review

  • WEI Lina ,
  • ZHAO Jing ,
  • LUO Cangxue ,
  • LIU Juan ,
  • SHI Changzheng
Expand
  • (College of Food and Biological Engineering, Shaanxi University of Science and Technology, Xi′an 710021, China)

Received date: 2019-01-25

  Online published: 2019-10-24

摘要

根皮素是属于黄酮类中的二氢查尔酮类化合物,具有抑菌、抗氧化和抗酪氨酸酶等一系列生物活性,在食品、药品、化妆品等领域中均有巨大的应用前景。目前研究多集中在根皮素的制备、结构修饰、生物活性及机理研究方面,针对根皮素研究的综述较少。因此,该文在参考国内外研究文献的基础上,对根皮素的制备,包括从天然产物中提取分离、化学法半合成及全合成制备、生物合成;化学结构修饰,如酯化修饰、醚化修饰以及缩合反应等;生物活性,包括抗氧化、抑制肿瘤细胞增殖、免疫抑制及抗炎等及其作用机制等方面进行了综述,并对目前根皮素开发研究中面临的问题及对策进行了探讨。以期为未来根皮素的研究应用提供参考借鉴。

本文引用格式

魏丽娜 , 赵静 , 罗仓学 , 刘娟 , 史长政 . 根皮素的制备、结构修饰及生理活性研究进展[J]. 食品与发酵工业, 2019 , 45(17) : 278 -285 . DOI: 10.13995/j.cnki.11-1802/ts.020079

Abstract

Phloretin is a kind of dihydrochalcone that belongs to flavonoids, which has a wide range of biological activities and great application prospects in food, medicine, cosmetics and other fields. At present, most researches have focused on the preparation, structural modification, biological activities and mechanisms of phloretin, however, a systematic review regarding phloretin is lacking. Therefore, this review summarized the ways of preparing phloretin, including extraction and separation from natural products, chemical semi-synthesis and total synthesis, as well as biological synthesis. Moreover, chemical structural modification of phloretin, such as esterified modification, etherification and condensation reaction etc. were reviewed. Furthermore, biological activities of phloretin and related mechanisms, such as tumor cell proliferation inhibition, anti-oxidation, immunosuppression and anti-inflammation etc. were discussed. The problems and countermeasures in developing and researching phloretin were mentioned, which aims to provide a reference for future research and application of phloretin.

参考文献

[1] ANTIKA L D,LEE E J,KIM Y H,et a1.Dietary phlorizin enhanees osteoblastogenic bone formation through enhancing β-catenin activity via GSK-3B inhibition in amodel of senile osteoporosis[J].The Journal of Nutritional Biochemistry,2017,49:42-52.
[2] LIN C C,CHU C L,NG C S,et a1.Immunomodulation of phloretin by impairing dendritic cell activation and function[J].Food Function,2014,5(5):997-1 006.
[3] SHIN S,KUM H,RYU D,et al.Protective effects of new phloretin derivative against UVB-induced damage in skin cell model and human volunteers[J].Int J Mol Sci,2014,15(10):18 919-18 940.
[4] LIN Y P,HSU F L,CHEN C S,et al.Constituents from the Formosan apple reduce tyrosinase activity in human epidermal melanocytes[J].Phytochemistry,2007,68(8):1 189-1 199.
[5] SUN Yinshi,LI Wei,LIU Zhengbo.Preparative isolation, quantification and antioxidant activity of dihydrochalcones from Sweet Tea (Lithocarpus polystachyus Rehd.)[J].Journal of Chromatography B,2015,1002:372-378.
[6] 李穆琼,范引科,李晰,等.根皮苷及根皮素对小鼠的半数致死量测定[J].中国药师,2013(16):466-468.
[7] VERSARI A,BIESENBRUCH S,BARBANTI D,et al.Adulteration of fruit juices:Dihydrochalcones as quality markers for apple juice identification[J].Lebensm Wiss U Technol,1997,30:585-589.
[8] PETERSEN C.Analyse des phloridzins[J].Annales Academie Science Francaise,1835(15):178.
[9] LEE K W,KIM Y J,KIM D O, et al.Major phenolics in apple and their contribution to the total antioxidant capacity[J].J Agric Food Chem,2007,51(22):6 516-6 520.
[10] 张金宏,李俊娥,魏新元,等.苹果渣中结合酚不同提取方法的研究[J].食品工业科技,2016(20):160-165.
[11] 李荣涛,刘杰超,焦中高,等.RP-HPLC法测定苹果树枝、叶中根皮苷的含量[J].食品工业科技,2009(30):385-387.
[12] SUN Lijun,GUO Yurong,FU Chengcheng,et al.Simultaneous separation and purification of total polyphenols,chlorogenic acid and phlorizin from thinned young apples[J].Food Chem,2013,136(2):1 022-1 029.
[13] WALDBAUER K,MCKINNON R,KOPP B.Apple Pomace as potential source of natural active compounds[J].Planta Medica, 2017, 83(12):994-1010.
[14] 赵艳敏,王皎,宋光明,等.苹果树枝和叶中根皮苷及根皮素含量变化研究[J].食品研究与开发,2013(7):95-98.
[15] 李淑玲,陈笑笑,赵宝龙,等. 10个苹果品种果实中酚类物质与褐变度分析[J].新疆农业科学,2016,53(7):1 199-1 203.
[16] DONG Huaqiang,NING Zhengxiang,YU Lijing,et al.Preparative separation and identification of flavonoid phloridzin from the crude extract of Sweet Tea(Lithocarpus polystachyus Rehd)[J].MOLECULES,2007(12):552-562.
[17] 侯雪瑞,谢阳,赖维,等.HPLC-MS检测荔枝果皮中的根皮苷[J].安徽医药,2014,18(12):2 255-2 257.
[18] 夏冬梅,李敏,王道清,等.藏药俄色叶中根皮苷、根皮素含量分析[J].中国现代医药,2014,16(8):618-622.
[19] 丁传波,赵婷,董岭,等.山荆子中根皮苷和黄酮含量的测定及其乙醇提取物的抗氧化活性[J].西北农林科技大学学报(自然科学版),2014,42(6):161-166.
[20] 殷法杰,秦国培,蒋海强,等.杜梨叶中根皮苷含量测定[J].山东中医杂志,2011,30(3):200-215.
[21] 李辰,陈卫林,郭玫,等.锁阳中儿茶素、根皮苷的提取及含量测定[J].五邑大学学报,2011, 25(1):23-28.
[22] ROZMER Z,PERJESI PAL.Naturally occurring chalcones and their biological activities[J].Phytochemistry Reviews,2016(15):87-120.
[23] 李秉擘.具有生物活性的天然产物根皮素的合成与纯化的相关研究[D].杭州:浙江大学,2012.
[24] VIDAVALUR S,CHUNDURI V R,SOMEPAL V.A concisesynthesis of polyhydroxydihydrochalcones and homoisoflavonoids [J].Tetrahedron,2006,62:841-846.
[25] 石磊,班树荣,冯秀娥,等. 二氢黄酮类衍生物的合成及抗肿瘤活性研究[J].中国药物化学杂质,2010(20):176-180.
[26] 陈艳君.大豆脂肪氧合酶抑制剂根皮素的合成及性能研究[D].无锡:江南大学,2008.
[27] CHRISTIAN G,HEIDI H,KARL S.Phloridzin:Biosynthesis,distri bution and physiological relevance in plants[J].Phytochem, 2010 (71): 838-843.
[28] DARE A,TOMES S,COONEY J,et al.The role of enoylreductase genes in phloridzin biosynthesis in apple[J].Plant Physiology and Biochemistry,2013,72:54-62.
[29] VALENTINO J S,KWAME W N A.Prodrug strategies to overcome poor water solubility[J].Adv Drug Delivery Rev,2007,59:677-694.
[30] 李翠萍,余燕影,曹树稳.根皮素乙酰阿魏酸酯的合成及抗氧化活性研究[J].天然产物研究与开发,2012,24:316-320.
[31] XU Bingbing,YU Yanying,WAN Pinghong,et al.Synthesis and antityrosinase,antioxidant activities of phloretinthiosemicarbazones [J].Res Chem Intermed,2013,3:19.
[32] 张宏宇,周武喜,赵余庆.根皮素衍生化的研究进展[J].中草药,2017, 48 (20):4 353-4 360.
[33] 魏丽娜.根皮素胺乙基醚化修饰及其生物活性、安全性和对三文鱼片保藏效果[D].西安:陕西师范大学,2015.
[34] MINDAUGAS L,PRANAS V,RAIMONDAS R,et al.Phenolic composition and antioxidant activity of Malus domestica leaves[J].The Scientific World Journal,2014(9):1-10.
[35] XUE Yunsheng, ZHENG Youguang,AN Lin,et al.Density functional theory study of the structure-antioxidant activity of polyphenolic deoxybenzoins[J].Food Chemistry,2014,151(20):198-206.
[36] ALINA S,GRAZYNA Z,ALEKSANDRA S.Analysis of polyphenolic compounds in extracts from leaves of some malus domestica cultivars:antiradical and antimicrobial analysis of these extracts[J].Biomed Res Int,2016,2016:1-12.
[37] SHAPIRO B.The mechanism of phloridzin glucosuria[J].Biochem J,1947,41:151-154.
[38] GAUCHER M,BERNONVILLE D D,THOMAS,et al.Histolocalization and physico-chemical characterization of dihydrochalcones: Insight into the role of apple major flavonoids[J].Phytochemistry,2013,90:78-89.
[39] LEE J H,REGMI S C,KIM J A,et al.Apple flavonoid phloretin inhibits escherichia coli O157∶H7 biofilm formation and ameliorates colon inflammation in rats[J].Infection and Immunity,2011,79(12):4 819-4 827.
[40] DAVIDE B,ERSILIA B,GIUSEPPINA L,et al.Biochemical and antimicrobial activity of phloretin and its glycosylated derivatives present in apple and kumquat[J].Food Chem,2014,160:292-297.
[41] HUANG W C,DAI Y W,PENG H L,et al.Phloretin ameliorates chemokines and ICAM-1 expression via blocking of the NF-κB pathway in the TNF-α-induced HaCaT human keratinocytes[J].International Immunopharmacology,2015,27(1):32-37.
[42] MIN J,LI X,HUANG K,et al.Phloretin induces apoptosis of non-small cell lung carcinoma A549 cells via JNK1/2 and p38 MAPK pathways[J].Oncology Reports,2015.
[43] 杜鹏. 根皮素酰腙衍生物的合成及其生物活性研究[D].南昌:南昌大学,2013.
[44] ZHENG Z P,CHENG K W, ZHU Q,et al.Tyrosinase inhibition constituents in roots of Morus nigra: a structure-activity relationship study[J].J Agric Food Chem,2010,58(9):5 368-5 373.
[45] CHANG,Weitien, HUANG Wenchung,LIOU Chianjiun.Evaluation of the anti-inflammatory effects of phloretin and phlorizin in lipopolysaccharide-stimulated mouse macrophages[J].Food Chem,2012,134:972-979.
[46] LU Xiaoyu,ZENG Yaoying,YE Yanxia,et al.Anti-inflammatory and immunosuppressive effect of phloretin[J].Acta Pharmaceutica Sinica,2009,44 (5):480-485.
[47] JIAO Pengfei.Study on cardiovascular protective effects of phloretin[J].J Mod Med Health,2012,28 (9):1 284-1 286.
[48] ZHU Qin, NATALIE,ZHANG Qishan,CHI F L,et al.In vitro attenuation of acrolein-induced toxicity by phloretin,a phenolic compound from apple[J].Food Chem,2012,135:1 762-1 768.
[49] 石珂,赵璐,游志鹏,等.根皮素对糖尿病小鼠光感受器视杆细胞的保护作用[J].眼科新进展,2014,34(9):809-812.
[50] WEI Lina,CHENG Jing, MENG Yonghong,et al.A novel formulation of thiamine dilaurylsulphate and its preservative effect on apple juice and sterilised milk[J].Food Chem,2014, 152: 415-422.
文章导航

/