Determination of dihydroquercetin in food by solid phase extraction-high performance liquid chromatography
LIU Guiliang1,2, LIAN Zhenxia3, GONG Pixue1,2, XUE Xia1,2, LIU Yanming1,2*, ZHU Jianhua1,2*
1(Shandong Institute for Food and Drug Control,Jinan 250101,China) 2(Shandong Research Center of Engineering and Technology for Safety Inspection of Food and Drug,Jinan 250101,China) 3(Shandong Academy of Pharmaceutical Sciences,Jinan 250101,China)
Abstract: A novel method for the determination of dihydroquercetin in food by solid-phase extraction-high performance liquid chromatography was established. The sample was extracted by V(methanol)∶V(2% acetic acid-water)=1∶1 and purified by hydrophile-lipophile balance (HLB) solid-phase extraction column. Methanol-0.1% acetic acid water was used as a mobile phase for gradient elution. The sample was analyzed by HPLC and determined by a diode array detector. The retention time and spectrogram were qualitative and quantitative by the external standard method. The results showed that the linear range was 0.8-100.0 μg/mL and the linear correlation coefficient was 0.999 9. The detection limit reached 0.6 mg/kg and the quantitative limit was 2.0 mg/kg. Three concentration levels of 2, 20 and 200 mg/kg were added to beverage, fermented milk and cocoa products respectively. The average recoveries were between 90.3% and 102.5%, and the relative standard deviations were between 0.45% and 1.42%. The method has a good purification effect, high sensitivity and accuracy, and is suitable for the determination of dihydroquercetin in food.
柳森, 张卫鹏,付警辉,等.二氢槲皮素的提取及含量测定的研究进展[J].吉林农业科技学院学报,2012,21(2):78-80.LIU S,ZHANG W P,FU J H,et al.Research progression in extraction and content assaying of dihydroquercetin[J].Journal of Jilin Agricultural Science and Technology University,2012,21(2):78-80.
[2]
乔华, 谢鋆,张晓云.花旗松素的生物活性及其应用[J].中草药,2003,34(8):15-17.QIAO H,XIE Y,ZHANG X Y,Bioactivity and application of semasin[J].Chinese Traditional and Herbal Drugs,2003,34(8):15-17.
[3]
FUKUI Y,NAKADOME K,ARIYOSHI H.Studies on the monomer flavonoides of the plants of Coniferae.II.Isolation of a new taxifolin glucoside from the leaves of Chamaecyparis obtusa Endlicher[J].Yakugaku Zasshi,1966,86(3):184-187.
[4]
张晓利, 赵瑞香,姜建福,等.葡萄皮渣中花旗松素提取工艺优化及其抗氧化能力测定[J].食品工业科技,2021,42(5):200-205;220.ZHANG X L,ZHAO R X,JIAN J F,et al.Optimization of extraction process of taxifolin from grape pomace and determination of its antioxidant capacity[J]. Science and Technology of Food Industry,2021,42(5):200-205;220.
[5]
曾志辉, 王晓莉,叶艳琼,等.花旗松素对H9C2细胞氧化应激保护作用机制研究[J].中国全科医学,2019,22(15):1 794-1 799.ZENG Z H,WANG X L,YE Y Q,et al.Oxidative stress protection mechanism of taxifolin in H9C2 cells[J].Chinese General Practice,2019,22(15):1 794-1 799.
[6]
周生学, 邵莹,郑毅男.长白落叶松3种黄酮化合物定性、定量分析及其抗氧化活性研究[J].食品工业科技,2019,40(23):66-72.ZHOU S X,SHAO Y,ZHENG Y N.Qualitative and quantitative analysis of 3 kinds of flavonoids in Larix olgensis var.Koreana extract and their antioxidant activities[J].Science and Technology of Food Industry,2019,40(23):66-72.
[7]
蔡华君, 郑毅男,刘文丛.二氢槲皮素抗炎抗过敏止痒作用的活性研究[J].人参研究,2015,27(3):32-35.CAI H J,ZHENG Y N,LIU C W.Study on taxifolin’s activities of anti-inflammatory,anti-allergic and relieving itching[J].Ginseng Research,2015,27(3):32-35.
[8]
王佳奇, 陈凯,王月亮,等.二氢槲皮素与二氢杨梅素抗炎活性对比研究[J].中国兽药杂志,2016,50(7):46-52.WANG J Q,CHEN K,WANG Y L,et al.Comparison of anti-inflammatory activity of dihydroquercetin and dihydromyricetin[J].Chinese Journal of Veterinary Drug,2016,50(7):46-52.
[9]
付警辉, 柴婧,韩佳彤,等.落叶松中花旗松素对酪氨酸酶的抑制作用[J].日用化学工业,2014,44(4):218-221.FU J H,CHAI J,HAN J T,et al.Inhibitory effect of taxifolin in Larix olgensis on tyrosinase[J].China Surfactant Detergent & Cosmetics,2014,44(4):218-221.
[10]
吴奋飞, 郭晶晶.花旗松素对糖尿病肾病大鼠的作用及机制分析[J].解放军药学学报,2018,34(6):514-516;520.WU F F,GUO J J.Alleviation of streptozotocin-induced diabetic nephropathy by taxifolin in rats[J].Pharmaceutical Journal of Chinese PLA,2018,34(6):514-516;520.
[11]
王佳奇, 宋明铭,陈凯,等.二氢槲皮素与二氢杨梅素的抗肿瘤活性对比[J].中国免疫学杂志,2016,32(11):1 614-1 620.WANG J Q,SONG M M,CHEN K,et al.Antitumor activity of dihydroquercetin and dihydromyricetin[J].Chinese Journal of Immunology,2016,32(11):1 614-1 620.
[12]
符小玲, 赵兴丹,张倩,等.花旗松素对人非小细胞肺癌细胞A549的作用及其机制的研究[J].肿瘤药学,2018,8(4):519-523;527.FU X L,ZHAO X D,ZHANG Q,et al.Effects of taxifolin on human non-small cell lung cancer A549 cells and its mechanism[J].Anti-tumor Pharmacy,2018,8(4):519-523;527.
[13]
国家食品安全风险评估中心.食叶草等3种新食品原料公开征求意见[EB/OL].(2020-11-12)[2021-01-14].https://www.cfsa.net.cn/Article/News.aspx?id=70B958EEF045BA-BB62E6E675E15FCE67685503FE3F240751China National Center for Food Safety Risk Assessment.Three kinds of new food raw materials such as leafy grass[EB/OL].(2020-11-12)[2021-01-14].https://www.cfsa.net.cn/Article/News.aspx?id=70B958EEF045BABB62E6E675E15FC-E67685503FE3F240751
[14]
刘东, 林书玉,梁戈亮.分光光度法测水红花子中花旗松素含量[J].现代生物医学进展,2008,8(2):331-332;320.LIU D,LIN S Y,LIANG G L.Determination of the content of taxifolin in princes-feather fruit by spectrophotometry[J].Progress in Modern Biomedicine,2008,8(2):331-332;320.
[15]
王宇, 王遂.分光光度法测定落叶松中的总黄酮含量[J].食品科学,2009,30(22):314-317.WANG Y,WANG S.Determination of total flavonoids in larch by spectrophotometry[J].Food Science,2009,30(22):314-317.
[16]
樊超, 钟艺青,粟芸,等.荧光猝灭法研究二氢槲皮素和二氢杨梅素与牛血清白蛋白的相互作用[J].安徽医药,2018,22(11):2 088-2 091.FAN C,ZHONG Y Q,SU Y,et al.An interaction study of bovine serum albumin with dihydroquercetin and dihydromyricetin by fluorescence quenching method[J].Anhui Medical and Pharmaceutical Journal,2018,22(11):2 088-2 091.
[17]
李云静, 何忠梅.HPLC波长切换联合梯度洗脱法同时测定荆防败毒丸中10个成分的含量[J].药物分析杂志,2017,37(3):414-421.LI Y J,HE Z M.Simultaneous determination of ten components in Jingfang Baidu pills by HPLC method with wavelength switching and gradient elution[J].Chinese Journal of Pharmaceutical Analysis,2017,37(3):414-421.
[18]
樊铁波, 刘红煜,汤青,等.HPLC法测定松针中二氢槲皮素含量[J].中国药师,2009,12(8):1 046-1 048.FAN T B,LIU H Y,TANG Q,et al.Determination the content of dihydroquercetin in pine needles by HPLC[J].China Pharmacist,2009,12(8):1 046-1 048.
[19]
李俊雅, 李君.RP-HPLC法测定不同产地花生壳中二氢槲皮素的含量[J].河南职工医学院学报,2013,25(2):128-130.LI J Y,LI J.Determination of dihydroquercetian in peanut hull by RP-HPLC[J].Journal of Henan Medical College for Staff and Workers,2013,25(2):128-130.
[20]
田超, 侯红萍.高效液相色谱同时测定葡萄酒中12种酚含量的研究[J].酿酒科技,2018,289(7):65-69.TIAN C,HOU H P.Simultaneous determination of 12 kinds of monophenols in grape wine by HPLC[J].Liquor-Making Science & Technology,2018,289(7):65-69.
[21]
闵捷, 饶毅,吕尚,等.HPLC法测定中药穿破石中花旗松素的含量[J].江西中医药大学学报,2017,29(6):79-81.MIN J,RAO Y,LV S,et al.Content determination of taxifolin in traditional Chinese medicine Chuanposhi by HPLC[J].Journal of Jiangxi University of Traditional Chinese Medicine,2017,29(6):79-81.
[22]
马悦, 赵乐凤,吕子燕,等.高效液相色谱-四极杆-静电场轨道阱高分辨质谱分析桑葚中黄酮类和多酚类物质[J].质谱学报,2017,38(1):45-51.MA Y,ZHAO L F,LV Z Y,et al.Analysis of flavonoids and polyphenols in mulberry extracts by high-performance liquid chromatography quadrupole-orbitrap mass spectrometry[J].Journal of Chinese Mass Spectrometry Society,2017,38(1):45-51.
[23]
李勇, 林茜,逄涛,等.超高效液相色谱-串联质谱法定量分析烟叶中的12种类黄酮物质[J].色谱,2015,33(7):746-752.LI Y,LIN Q,PANG T,et al.Determination of 12 flavonoids in tobacco leaves using ultra-high performance liquid chromatography-tandem mass spectrometry[J].Chinese Journal of Chromatography,2015,33(7):746-752.
[24]
丁丽娜, 邱亦亦,束彤,等.超高效液相色谱-质谱联用技术解析沙棘果超临界CO2萃取物中黄酮类天然产物结构[J].食品科学,2019,40(18):273-280.DING L N,QIU Y Y,SHU T,et al.Determination of flavonoids in the supercritical CO2 extract of sea buckthorn fruit by using ultra-high performance liquid chromatography-mass spectrometry[J].Food Science,2019,40(18):273-280.
[25]
张宇, 苏丹.二氢槲皮素提取方法的比较和优化[J].中医学报,2015,30(10):1 470-1 472.ZHANG Y,SU D.Comparison and optimization of the extraction technologies of dihydroquercetin[J].China Journal of Chinese Medicine,2015,30(10):1 470-1 472.
[26]
马春慧, 孙震,黄金明,等.超声-微波交替法提取落叶松二氢槲皮素[J].化工进展,2010,29(1):134-139;145.MA C H,SUN Z,HUANG J M,et al.Extraction of dihydroquercetin from larch wood with ultrasonic-microwave alternant method[J].Chemical Industry and Engineering Progress,2010,29(1):134-139;145.
2021, Vol. 47 
