新橙皮苷二氢查耳酮的调味应用及其生理活性研究进展Research Progress of Flavor Modifying and Physiological Activity of Neohesperidin dihydrochalcone
雷琳,黄宝华,卢宇靖,周金林
摘要(Abstract):
新橙皮苷二氢查耳酮(NHDC)是高效、无毒、低热值甜味剂,具有风味改良和苦味抑制的功效,因此在食品行业中具有广阔的应用前景。首先概述NHDC的结构、性质及其合成方法进展。新橙皮苷在碱性条件下水解后经氢化还原可制得NHDC。由于新橙皮苷来源不足,目前一般是以来源广泛的柚苷为原料的化学合成法和以价廉易得的橙皮苷为原料的生物合成法制备新橙皮苷。然后,着重介绍了NHDC的调味应用与生理活性。NHDC具有増甜、增香、掩盖苦味、修饰风味等特性;同时具有抗氧化性和清除自由基能力,并且具有降低胆固醇、降血糖、抑制胃酸分泌和抑制α-淀粉酶等活性。NHDC由于极佳的改善口味的功效与优良的生理活性,是非常有前景的功能性甜味剂。
关键词(KeyWords): 新橙皮苷二氢查耳酮;调味;生理功能
基金项目(Foundation): 广东省自然科学基金资助项目(S2012010010200);; 广东省科技计划项目(2012B020306007);; 广东省佛山市南海区“蓝海人才计划”第三批创业团队项目
作者(Author): 雷琳,黄宝华,卢宇靖,周金林
参考文献(References):
- [1]Horowitz R M,Gentili B.Dihydrochalcone derivatives and their use as sweetening agents:United States,US 3087821[P].1963-04-30.
- [2]戴启广,陈国平,王幸宜.新型甜味剂——二氢查尔酮衍生物[J].精细化工中间体,2004,34(3):7-9.
- [3]Varzakas T,Labropoulos A,Anestis S.Sweeteners:nutritional aspects,applications,and production technology[M].United States:CRC Press,2012.
- [4]EFSA panel on additives and products or substances used in animal feed(FEEDAP);scientific opinion on the safety and efficacy of neohesperidine dihydrochalcone when used as a sensory additive for piglets,pigs for fattening,calves for rearing and fattening,lambs for rearing and fattening,dairy sheep,ewes for reproduction,salmonids and dogs[J].EFSA Journal,2011,9(12):2444.
- [5]苏东林,单杨.柑橘果皮中功能性成分的作用概述[J].现代食品科技,2006,22(2):260-262.
- [6]温辉梁,欧阳振宇,胡晓波,等.新橙皮苷二氢查耳酮的研究进展[J].中国调味品,2008,33(10):70-73.
- [7]Francisco Borrego.Alternative Sweeteners[M].United States:Fourth Edition,2011.
- [8]Krbechek L,Dowling B,Wagner R.Dihydrochalcone sweeteners-sensory and stability evaluation[J].Journal of Food Science,1969,34:101-103.
- [9]Canales I,Borrego F,Lindley M G.Neohesperidin dihydrochalcone stability in aqueous buffer solutions[J].Journal of Food Science,1992,57(3):589-561.
- [10]Waalkens-Berendsen D H,Kuilman-Wahls M E M,Bar A.Embryotoxicity and teratogenicity study with neohesperidin dihydrochalcone in rats[J].Regulatory Toxicology and Pharmacology,2004,40:74-79.
- [11]Braune A,Engst W,Blaut M.Degradation of Neohesperidin dihydrochalcone by human intestinal bacteria[J].Journal of Agricultural and Food Chemistry,2005,53:1782-1790.
- [12]徐国波,袁小红,冯运波,等.常温常压下合成新橙皮苷二氢查尔酮的工艺研究[J].北京化工大学学报,2010,37(5):111-114.
- [13]于宏伟,张绍岩,陆敏,等.新橙皮苷研究进展[J].河南农业科学,2011,40(8):33-35.
- [14]Horowitz R M,Gentiii B.Conversion of naringin to neohesperidin and neohesperidin dihydrochalcone:United States,US 3375242[P].1968-03-26.
- [15]夏时川,陈宁,吴尚全.新橙皮苷的合成工艺:中国,CN101863940B[P].2014-02-05.
- [16]Frydman A,Weisshaus O,Huhman D V,et al.Metabolic engineering of plant cells for biotransformation of hesperedin into neohesperidin,a substrate for production of the low-calorie sweetener and flavor enhancer NHDC[J].Journal of Agricultural and Food Chemistry,2005,53,9708-9712.
- [17]朱思明,于淑娟,何树珍.一种新橙皮苷的高通量酶法的合成方法:中国,CN 101709316B[P].2012-05-09.
- [18]周金林,黄宝华,卢宇靖.一种酶法制备新橙皮苷的方法:中国,CN 103224968A[P].2013-07-31.
- [19]She Gai-mei,Wang Si,Liu Bin.Dihydrochalcone glycosides from oxytropis myriophylla[J].Chemistry Central Journal,2011(5):71-73.
- [20]Zygler A,Wasik A,Namies'nik J.Analytical methodologies for determination of artificial sweeteners in foodstuffs[J].Trends in Analytical Chemistry,2009,28(9):1082-1102.
- [21]Zygler A,Wasik A,Kot-Wasik A,et al.Determination of nine high-intensity sweeteners in various foods by highperformance liquid chromatography with mass spectrometric detection[J].Anal.Bioanal.Chem.,2011,400:2159-2172.
- [22]Lim H S,Park S K,Kwak I S,et al.HPLC-MS/MS analysis of 9artificial sweeteners in imported foods[J].Food Science and Biotechnology,2013,22:233-240.
- [23]Wang Xian-qin,Yu Pan,Ma Jian-she.Application of a liquid chromatography-tandem mass spectrometry method to the pharmacokinetics,bioavailability and tissue distribution of neohesperidin dihydrochalcone in rats[J].Xenobiotica,2013.
- [24]Servant G,Tachdjian C,Li Xiao-dong,et al.The sweet taste of true synergy:positive allosteric modulation of the human sweet taste receptor[J].Trends in Pharmacological Sciences,2011,32(11):631-636.
- [25]Ghanemi A.Targeting G protein coupled receptor-related pathways as emerging molecular therapies[J].Saudi Pharmaceutical Journal,2013.
- [26]Winnig M,Bufe B,Kratochwil N A,et al.The binding site for neohesperidin dihydrochalcone at the human sweet taste receptor[J].BMC Structural Biology,2007(7):66.
- [27]Servant G,Tachdjian C,Tang Xiao-qing,et al.Positive allosteric modulators of the human sweet taste receptor enhance sweet taste[J].PNAS,2010,107(10):4746-4751.
- [28]Fujiwara S,Imadaa T,Nakagita T,et al.Sweeteners interacting with the transmembrane domain of the human sweet-taste receptor induce sweet-taste synergisms in binary mixtures[J].Food Chemistry,2012,130(3):561-568.
- [29]Rathjen S,Schwarz S.Edible composition with low glycemic index and the taste of pure sucrose:United States,US 20080044541A1[P].2008-02-21.
- [30]DuBois G E,Crosby G A,Stephenson R A,et al.Dihydrochalcone sweeteners.Synthesis and sensory evaluation of sulfonate derivatives[J].Journal of Agricultural and Food Chemistry,1977,25(4):763-772.
- [31]Guadangni D G,Maier V P,Turnbaugh J H.Some factors affecting sensory thresholds and relative bitterness of limonin and naringin[J].Journal of the Science of Food and Agriculture,1974,25(10):1199-1205.
- [32]Choi D H,Kim N A,Nam T S.Evaluation of tastemasking effects of pharmaceutical sweeteners with an electronic tongue system[J].Drug Dev.Ind.Pharm.,2014,40(3):308-317.
- [33]Boghani N,Gebreselassie P,Bingley C A.Taste potentiator compositions and edible confectionery and chewing gum products containing same:United States,US 8455033B2[P].2013-06-04.
- [34]Lindley M G,Beyts P K,Canales I,et al.Flavor modifying characteristics of the intense sweetener neohesperidin dihydrochalcone[J].Journal of Food Science,1993,58(3):592-594.
- [35]Nahon D F,Roozen J P,Graaf C D.Sweetness flavor interactions in soft drinks[J].Food Chemistry,1996,56(3):283-289.
- [36]Schrader D,Christopher S L,Henze T,et al.Liquid aroma and flavoring compositions:United States,US0295260A1[P].2013-11-07.
- [37]Suarez J,Herrera M D,Marhuenda E.In vitro scavenger and antioxidant properties of neohesperidin dihydrochalcone[J].Phytomedicine,1998,5(6):469-473.
- [38]Mkynen K,Jitsaardkul S,Tachasamran P,et al.Cultivar variations in antioxidant and antihyperlipidemic properties of pomelopulp(Citrus grandis L.Osbeck)in Thailand[J].Food Chemistry,2013,139:735-743.
- [39]Caengprasath N,Ngamukote S,Mkynen K,et al.The protective effects of pomelo extract(citrus grandisl.osbeck)against fructose-mediated protein oxidation and glycation[J].EXCLI Journal,2013,12:491-502.
- [40]Choi J M,Yoon B S,Lee S K,et al.Antioxidant properties of neohesperidin dihydrochalcone:inhibition of hypochlorous acid-induced DNA strand breakage,protein degradation,and cell death[J].Biological&Pharmaceutical Bulletin,2007,30(2):324-330.
- [41]Kuijpers T F M,Herk T V,Vincken J P,et al.Potato and mushroom polyphenol oxidase activities are differently modulated by natural plant extracts[J].Journal of Agricultural and Food Chemistry,2014,62:214-221.
- [42]Potin A,Oresajo C,Chen Nan-nan,et al.Method of inhibiting premature aging of human skin caused by exposure to infrared radiation:United States,US20140045777A1[P].2014-02-13.
- [43]Bok S H,Jeong T S,Hwan B K,et al.Use of neohesperidin dihydrochalcone for the manufacture of a medicament for preventing or treating elevated blood lipid level-related diseases:European,EP 1113726 B1[P].2004-03-24.
- [44]Bok S H,Jeong T S,Choi M S,et al.Bioflavonoids as plasma high density lipoprotein level increasing agent:Canadian,CA 2346325A1[P].2001-04-07.
- [45]Takii H,Matsumoto K,Kometani T,et al.Lowering effect of phenolic glycosides on the rise in postprandial glucose in mice[J].Bioscience Biotechnology and Biochemistry,1997,61(9):1531-1535.
- [46]Kashani-Amin E,Larijani B,Ebrahim-Habibi A.Neohesperidin dihydrochalcone:presentation of a small molecule activator of mammalian alpha-amylase as an allosteric effector[J].FEBS Lett.,2013,587:652-658.
- [47]张硕,洪波,王庆林,等.4种黄酮类化合物对CCl4致小鼠肝纤维化的防治作用[J].华西药学杂志,2012,27(2):141-43.
- [48]Hu Li-hua,Li Ling-rui,Xu De-mei,et al.Protective effects of neohesperidin dihydrochalcone against carbon tetrachloride-induced oxidative damage in vivo and in vitro[J].Chemico-Biological Interactions,2014,213:51-59.
- [49]Suhrez J,Herrera M D,Marhuenda E.Hesperidin and Neohesperidin dihydrochalcone on different experimental models of induced gastric ulcer[J].Phytotherapy Research,1996,10:616-618.
- [50]Beards E,Tuohy K,Gibson G.A human volunteer study to assess the impact of confectionery sweeteners on the gut microbiota composition[J].British Journal of Nutrition,2010,104:701-708.
- [51]Daly K,Darby A C,Hall N,et al.Dietary supplementation with lactose or artificial sweetener enhances swine gut lactobacillus population abundance[J].British Journal of Nutrition,2014,111(suppl 1):S30-S35.