花色苷生物转化修饰的研究进展

doi:10.13560/j.cnki.biotech.bull.1985.2019-0262

摘要/Abstract

摘要： 花色苷是植物界中广泛存在的一种天然的水溶性食用色素,是植物呈现靓丽颜色的重要物质基础,具有多种重要的生理功能和生物活性,药用和保健价值较高,具有巨大的商业应用潜力。花色苷由花色素和糖类物质经糖苷键缩合而成,其结构母核是2-苯基苯并吡喃阳离子,且结构上存在多个活性羟基,稳定性较差,对酸碱度、光照、温度等因素敏感,极易导致色泽或活性的消失。此外,其亲水性较强,在疏水环境中溶解性差,不易透过磷脂双分子层生物膜,导致生物利用度较低。在保持花色苷原有基本骨架结构基础上的酰基化修饰改造,可以获得理化特性改善、稳定性增强且具有良好生物利用度的花色苷酯衍生物,是解决花色苷应用难题的一条重要途径,也是当今研究的热点和难点。目前可用于花色苷类物质生物转化酰基化修饰的方法主要植物细胞转化、酶法转化和微生物全细胞转化。综述了花色苷的稳定性、生物活性及酰基化花色苷的生物合成方法,旨在为进一步开展花色苷的结构稳定性与生理活性研究及其在药品、食品、化妆品等行业中的广泛应用提供有益参考。

关键词: 花色苷, 生物活性, 生物转化, 微生物细胞转化

Abstract: Anthocyanins,as a natural water-soluble food coloring,possess a variety of important physiological functions and biological activities as well as high medicinal and health care value,and thus demonstrate great commercial potential. Anthocyanins are formed by the condensation reaction of anthocyanidin and saccharides in glycosidic bonds. The mother nucleus of the anthocyanin is 2-phenylbenzopyryalium cationic aglycone,and there are multiple active hydroxyl groups in the structure,which have poor stability and are sensitive to pH value,light,temperature and other factors,and easily leading to the loss of color or activity. In addition,anthocyanin is strongly hydrophilic and poor soluble in hydrophobic environment,thus it is not easy to pass through the phospholipid bilayer biofilm,resulting in a low bioavailability. Therefore,anthocyanin ester derivatives with improved physical and chemical properties and enhanced stability and good bioavailability may be obtained via acylation modification of anthocyanins on the basis of maintaining the original basic structure,which is an important approach to solve the problem in applying anthocyanins and also a hot and difficult topic in the current research. At present,biological acylation modification of anthocyanins mainly includes plant cell transformation,enzymatic transformation and whole cell microbial transformation. In this paper,the stability,bioactivity and acylation modification with biotransformation of anthocyanins are reviewed,which may provide useful reference for further research on the structural stability and physiological activity of anthocyanins and their broad application in pharmaceutical,food and cosmetic industries.

Key words: anthocyanins, biological activity, biotransformation, cell microbial transformation

赵祥杰, 杨文君, 杨荣玲, 吴婷婷, 王朝宇, 许宁宁, 何佳美. 花色苷生物转化修饰的研究进展[J]. 生物技术通报, 2019, 35(10): 205-211.

ZHAO Xiang-jie, YANG Wen-jun, YANG Rong-ling, WU Ting-ting, WANG Zhao-yu, XU Ning-ning, HE Jia-mei. Research Progress on Biotransformation Modification of Anthocyanins[J]. Biotechnology Bulletin, 2019, 35(10): 205-211.

参考文献

[1] He J, Giusti MM.Anthocyanins:natural colorants with health-promoting properties[J]. Annu Rev Food Sci Technol, 2010, 1(7):163-187.
[2] Serra D, Almeida LM, Dinis TCP.Anti-inflammatory protection afforded by cyanidin-3-glucoside and resveratrol in human intestinal cells via Nrf2 and PPAR-γ:comparison with 5-aminosalicylic acid[J]. Chemico-Biological Interactions, 2016, 260:102-109.
[3] Kopjar M, Orsolic M, Pilizota V.Anthocyanins, phenols, and antioxidant activity of sour cherry puree extracts and their stability during storage[J]. Int J Food Prop, 2014, 17(6):1393-1405.
[4] 崔清慧. 蓝莓花色苷的酰化及抑制Hep G2和Caco-2细胞增殖活性的研究[D]. 北京:北京林业大学, 2016.
[5] Shelly H, Hyun C, Lei Z, et al.Antiproliferative and antioxidant properties of anthocyanin-rich extract from acai[J]. Food Chemistry, 2010, 118(2):208-214.
[6] Xu JW, Ikeda K, Yamori Y.Upregulation of endothelial nitric oxide synthase by cyanidin-3-glucoside, a typical anthocyanin pigment[J]. Hypertension, 2004, 44(2):217-222.
[7] Rein M.Copigmentation reactions and color stability of berry anthocyanins[D]. Helsinki:University of Helsinki, 2005.
[8] Hassimotto NMA, Genovese MI, Lajolo FM.Absorption and metabolism of cyanidin-3-glucoside and cyanidin-3-rutinoside extracted from wild mulberry(Morus nigra L.)in rats[J]. Nutrition Research, 2008, 28(3):198-207.
[9] Zhao CL, Yu YQ, Chen ZJ, et al.Stability-increasing effects of anthocyanin glycosyl acylation[J]. Food Chemistry, 2017, 214:119-128.
[10] Zhao LY, Chen J, Wang ZQ, et al.Direct acylation of cyanidin-3-glucoside with lauric acid in blueberry and its stability analysis[J]. Int J Food Prop, 2016, 19(1):1-12.
[11] Matera R, Gabbanini S, Berretti S, et al.Acylated anthocyanins from sprouts of Raphanus sativus cv. Sango:Isolation, structure elucidation and antioxidant activity[J]. Food Chemistry, 2015, 166:397-406.
[12] Jordheim M, Calcott K, Gould KS, et al.High concentrations of aromatic acylated anthocyanins found in cauline hairs in Plectranthus ciliatus[J]. Phytochemistry, 2016, 128:27-34.
[13] Oyama K, Kawaguchi S, Yoshida K, et al.Synthesis of pelargonidin 3-O-6''-O-acetyl-β-D-glucopyranoside, an acylated anthocyanin, via the corresponding kaempferol glucoside[J]. Tetrahedron Letters, 2007, 48(34):6005-6009.
[14] Dougall DK, Baker DC, Gakh EG, et al.Anthocyanins from wild carrot suspension cultures acylated with supplied carboxylic acids[J]. Carbohydrate Research, 1998, 310(3):177-189.
[15] Sari P, Setiawan A, Siswoyo TA.Stability and antioxidant activity of acylated jambolan(Syzygium cumini)anthocyanins synthesized by lipase-catalyzed transesterification[J]. International Food Research Journal, 2015, 22(2):671-676.
[16] Castro VC, Silva PHA, Oliveira EB, et al.Extraction, identiﬁcation and enzymatic synthesis of acylated derivatives of anthocyanins from jaboticaba(Myrciaria cauli?ora)fruits[J]. International Journal of Food Science and Technology, 2014, 49(1):196-204.
[17] Furtado P, Figueiredo P, Neves HCD, et al.Photochemical and thermal degradation of anthocyanidins[J]. J Photoch Photobiol, 1993, 75(2):113-118.
[18] Maciel LG, Do C, Azevedo L, et al.Hibiscus sabdariffa anthocya-nins-rich extract:Chemical stability, in vitro antioxidant and antiproliferative activities[J]. Food and Chemical Toxicology, 2018, 113:187-197.
[19] Luna-vital D, Li Q, West L, et al. Anthocyanin condensed forms do not affect color or chemical stability of purple corn pericarp extracts stored under different pHs[J]. Food Chemistry, 2017, 232:639-647.
[20] Xie LH, Su HM, Sun CD, et al.Recent advances in understanding the anti-obesity activity of anthocyanins and their biosynthesis in microorganisms[J]. Trends Food Sci Technol, 2018, 72:13-24.
[21] Song Y, Huang LL, Yu JF.Effects of blueberry anthocyanins on retinal oxidative stress and inflammation in diabetes through Nrf2/HO-1 signaling[J]. Journal of Neuroimmunology, 2016, 301:1-6.
[22] Chen YF, Shibu MA, Fan MJ, et al.Purple rice anthocyanin extract protects cardiac function in STZ-induced diabetes rat hearts by inhibiting cardiac hypertrophy and fibrosis[J]. The Journal of Nutritional Biochemistry, 2016, 31:98-105.
[23] Pascual-Teresa S.Molecular mechanisms involved in the cardiovascular and neuroprotective effects of anthocyanins[J]. Archives of Biochemistry and Biophysics, 2014, 559(5):68-74.
[24] Peixoto H, Roxo M, Krstin S, et al.Anthocyanin-rich extract of Acai(Euterpe precatoria, Mart. )mediates neuroprotective activities in Caenorhabditis elegans[J]. J Functi Foods, 2016, 26:385-393.
[25] Wang LJ, Li YM, Lei L, et al.Cranberry anthocyanin extract prolongs lifespan of fruit flies[J]. Experimental Gerontology, 2015, 69:189-195.
[26] Wang L, Zhao Y, Zhou Q, et al.Characterization and hepatoprotective activity of anthocyanins from purple sweet potato(Ipomoea batatas, L. cultivar Eshu, No. 8)[J]. Journal of Food and Drug Analysis, 2016, 25(3):607-618.
[27] Wang YW, Luan GX, Zhou W, et al.Subcritical water extraction, UPLC-Triple-TOF/MS analysis and antioxidant activity of anthocyanins from Lycium ruthenicum Murr[J]. Food Chemistry, 2018, 249:119-126.
[28] Zhao ZG, Yan HF, Zheng R, et al.Anthocyanins characterization and antioxidant activities of sugarcane(Saccharum officinarum L.)rind extracts[J]. Ind Crops Products, 2018, 113:38-45.
[29] Abdel-Aal ESM, Hucl P, Rabalskia I.Compositional and antioxidant properties of anthocyanin-rich products prepared from purple wheat[J]. Food Chemistry, 2018, 254:13-19.
[30] Konczak-Islam I, Okuno S, Yoshimoto M, et al.Composition of phenolics and anthocyanins in a sweet potato cell suspension culture[J]. Biochem Eng J, 2003, 14(3):155-161.
[31] Konczak I, Terahara N, Yoshimoto M, et al.Regulating the quality of anthocyanins and phenolic acids in a sweetpotato cell culture towards production of polyphenolic complex with enhanced physiological activity[J]. Trends in Food Science & Technology, 2005, 16(9):377-388.
[32] Moris F, Gotor V.A useful and versatile procedure for the acylation of nucleosides through an enzymic reaction[J]. Journal of Organic Chemistry, 1993, 58(3):653-660.
[33] Zaks A, Klibanov AM.Enzymatic catalysis in nonaqueous solvents[J]. J Biol Chem, 1988, 263(7):3194-3201.
[34] Yan QL, Zhang LH, Zhang XF, et al.Stabilization of grape skin anthocyanins by copigmentation with enzymatically modified isoquercitrin(EMIQ)as a copigment[J]. Food Research International, 2013, 50(2):603-609.
[35] Yan Z, Li CY, Zhang LX, et al.Enzymatic acylation of anthocyanin isolated from black rice with methyl aromatic acid ester as donor:Stability of the acylated derivatives[J]. Journal of Agricultural and Food Chemistry, 2016, 64(5):1137-1143.
[36] Narancic T, Davis R, Nikodinovic-Runic J, et al.Recent developments in biocatalysis beyond the laboratory[J]. Biotechnology Letters, 2015, 37(5):943-954.
[37] Wachtmeister J, Rother D.Recent advances in whole cell biocatalysis techniques bridging from investigative to industrial scale[J]. Curr Opin Biotechnol, 2016, 42:169-177.
[38] Yang MY, Wu H, Lian Y, et al.Using ionic liquids in whole-cell biocatalysis for the nucleoside acylation[J]. Microbial Cell Factories, 2014, 13:143.
[39] 宋静. 提高蓝靛果花色苷稳定性菌种的筛选及作用条件研究[D]. 哈尔滨:东北林业大学, 2011.
[40] Cheng JR, Liu XM, Chen ZY, et al.Mulberry anthocyanin biotransformation by intestinal probiotics[J]. Food Chemistry, 2016, 213:721-727.
[41] Liang LH, Wu XY, Zhao T, et al.In vitro bioaccessibility and antioxidant activity of anthocyanins from mulberry(Morus atropurpurea Roxb. )following simulated gastro-intestinal digestion[J]. Food Res Int, 2012, 46(1):76-82.
[42] Forester SC, Waterhouse AL.Identification of cabernet sauvignon anthocyanin gut microflora metabolites[J]. Journal of Agricultural and Food Chemistry, 2008, 56(19):9299-9304.
[43] Chen Y, Li Q, Zhao T, et al.Biotransformation and metabolism of three mulberry anthocyanin monomers by rat gut microflora[J]. Food Chemistry, 2017, 237:887-894.
[44] Jeon A, Suk K, Ji GE, et al.Assay of β-glucosidase activity of bifidobacteria and the hydrolysis of isoflavone glycosides by Bifidobacterium sp. Int-57 in soymilk fermentation[J]. Journal of Microbiology and Biotechnology, 2002, 12(1):8-13.