‘夏黑’葡萄花色苷定性检测及组成成分分析
|
摘要
为研究‘夏黑’葡萄花色苷的组成成分特点,以‘夏黑’葡萄皮为检测试材,以甲酸水溶液提取花色苷,利用高效液相色谱+飞行时间质谱和液质联用仪(UPLC-Q-TOF-MS)对‘夏黑’葡萄未知花色苷的种类与含量进行测定。结果表明,‘夏黑’葡萄成熟期果皮中检测到10种不同结构的花色苷,其糖苷主要以葡糖苷为主,但也存在鼠李糖苷、二葡糖苷。10种花色苷中有3种以锦葵色素为糖苷配基,有2种以芍药素为糖苷配基,有2种以飞燕草色素配基。其中锦葵色素-3-葡萄糖苷在总的花色苷含量中比例最大,为29%,其次是锦葵色素-3-(6-香豆基)-5-葡萄糖苷,所含比例为26%,芍药素-3-葡萄糖苷-5-葡萄糖苷第3位,为17%,飞燕草色素-3-葡糖苷第4位,为10%,锦葵素-3-葡萄糖苷-5-葡萄糖苷第5位,为9%。可见,‘夏黑’葡萄含有花色苷资源相当丰富,自然界中常见的6种基本花色苷,‘夏黑’葡萄占有3种。
To study the composition of anthocyanins from‘Summer Black'grape, we determine the type and content of anthocyanins unknown in‘Summer Black'grape, which are extracted with aqueous solution of formic acid from the peel, and conduct the analysis by high performance liquid chromatography, time of flight mass spectrometry, liquid chromatography-mass spectrometry(UPLC-Q-TOF-MS). The results show that there are 10 kinds of anthocyanins with different structures detected in the peel of maturing‘Summer Black'grape, the main glucosides are glucosides, but rhamnoside and diglucoside also exist. Among the 10 kinds of anthocyanins, 3 kinds of agar pigments are aglucone, 2 kinds of peoniflorin are aglycone, and 2 kinds are delphinidin. Among them, malvaceone-3-glucoside has the largest proportion of the total anthocyanin content,which is 29%, followed by malvidin-3-(6-coumaroyl)-5-glucoside with a proportion of 26%, peonidin-3-glucoside-5-glucoside accounts for 17%, delphinidin-3-glucoside is 10%, malolaose-3-glucoside-glycoside is 9%. Therefore,‘Summer Black'grape has rich anthocyanin resource, and occupies three of the six kinds of basic anthocyanins in nature.
To study the composition of anthocyanins from‘Summer Black'grape, we determine the type and content of anthocyanins unknown in‘Summer Black'grape, which are extracted with aqueous solution of formic acid from the peel, and conduct the analysis by high performance liquid chromatography, time of flight mass spectrometry, liquid chromatography-mass spectrometry(UPLC-Q-TOF-MS). The results show that there are 10 kinds of anthocyanins with different structures detected in the peel of maturing‘Summer Black'grape, the main glucosides are glucosides, but rhamnoside and diglucoside also exist. Among the 10 kinds of anthocyanins, 3 kinds of agar pigments are aglucone, 2 kinds of peoniflorin are aglycone, and 2 kinds are delphinidin. Among them, malvaceone-3-glucoside has the largest proportion of the total anthocyanin content,which is 29%, followed by malvidin-3-(6-coumaroyl)-5-glucoside with a proportion of 26%, peonidin-3-glucoside-5-glucoside accounts for 17%, delphinidin-3-glucoside is 10%, malolaose-3-glucoside-glycoside is 9%. Therefore,‘Summer Black'grape has rich anthocyanin resource, and occupies three of the six kinds of basic anthocyanins in nature.
引文
[1] Escribano-bail N M T, Santos-buelga C, Rivasgonzalo J C.Anthocyanins in cereals[J]. Rev Journal of Chromatography A,2004,1054:129-141.
[2]郑时莲,邓泽元,蒋海伟,等.茄子皮中花色苷提取方法的比较及其抗氧化活性研究[J].中国食品学报,2017,17(1):92-99.
[3]罗赟,陈宗玲,宋卫堂,等.草莓果实花色苷成分组成鉴定及分析[J].中国农业大学学报,2014,19(5):86-94.
[4]吕昱,严敏.紫薯花色苷的生理功能及分离纯化研究进展[J].食品与机械,2013,19(4):250-253,257.
[5]魏一枝,邓洁红,王维茜,等.花色苷纯化分离及鉴定研究进展[J].包装与食品机械,2014,32(1):50-54.
[6] Luque-rodriguez J M, Castro L D, Perez-juan P. Dynamic superheated liquid extraction of anthocyanins and other phenolics from red grape skins of winemaking residues[J]. Bioresource Technology,2007,98(14):2705-2713.
[7]吴斌,张玉丽,程琳琳,等.鲜食葡萄花色苷的研究进展[J].现代食品科技,2012,28(4):441-444.
[8]凌关庭.食品添加剂手册[M].北京:中国化学出版社,1997:543-545.
[9] Liang Z, Wu B, Fan P, et al. Anthocyanin composition and content in grape berry skin in Vitis germplasm[J]. Food Chemistry,2008,111(4):837-844.
[10]孙磊,樊秀彩,张颖,等.部分中国野生葡萄果皮花色苷组分分析[J].果树学报,2015,32(6):1143-1151.
[11]周君,陈宗玲,张琼,等.套袋对桃果实成熟过程中酚酸类和类黄酮类物质积累的影响[J].园艺学报,2009,36(12):1717-1724.
[12]王燕,陈学森,刘大亮,等.‘紫红1号’红肉苹果果肉抗氧化性及花色苷分析[J].园艺学报,2012,39(10):1991-1998.
[13] Xiao L, Min X, Yun L, et al. The effect of RNAi-induced silencing of FaDFR on anthocyanin metabolism in strawberry(Fragaria×ananassa)fruit[J]. Scientia Horticulturae,2013,160:123-128.
[14]肖敏.FaANS基因表达与草莓果实花色苷代谢的关系[D].北京:中国农业大学,2012.
[15] Anderson Q M, Joudheim M. Flavonoids:chemistry, biochemistry,and applications[M]. London:CRC Taylor&Francis Group,2006.
[16] Nardini M, Daquino M, Tomassi G, et al. Inhibition of human LDL oxidation by caffeic acid and other hydroxycinnamic acid derivatives[J]. Free Radical Biology and Medicine,1995,19(5):541-552.
[17] Honda T, Saito N. Recent progress in the chemistry of polyacylated anthocyanins as flower color pigments[J]. Heterocycles,2002,56(1):633-692.
[18] Nakayama T, Suzuki H, Nishino T. Anthocyanin acyltransferases:Specificities, mechanism, phylogenetics, and applications[J].Journal of Molecular Catalysis B:Enzymatic,2003,23(2):117-132.
[19]肖慧琳,张珍珍,朱保庆,等.川西北干旱河谷地区赤霞珠葡萄果实花色苷的积累[J].中外葡萄与葡萄酒,2012,3:16-21.
[20]张珍珍,邓玉杰,陈新军,等.新疆伊犁地区赤霞珠葡萄成熟过程中花色苷组成及含量变化研究[J].现代食品科技,2018,34(2):1-6.
[21] Podsdek A, Redzynia M, Klewicka E, et al. Matrix effects on the stability and antioxidant activity of red cabbage anthocyanins under simulated gastrointestinal digestion[J]. BioMed Research International,2014(2):1-11.
[22] Juadjur A, Mohn C, Schantz M, et al. Fractionation of an anthocyanin-rich bilberry extract and in vitro antioxidative activity testing[J]. Food Chemistry,2015,167(1):418-424.
[23] Santos-buelga C, Escribano-bailon M T. Anthocyanin copigmentation-evaluation, mechanisms and implications for the colour of red wines[J]. Current Organic Chemistry,2012,16(6):715-723.
[24]李丹,沈才洪,马懿.夏黑葡萄花色苷的提取及抗氧化活性研究[J].应用化工,2016,45(8):1418-1423.
[25]许萍,乔勇进,周慧娟,等.固体二氧化氯保鲜剂对夏黑葡萄保鲜效果的影响[J].食品科学,2012,33(10):282-286.
[2]郑时莲,邓泽元,蒋海伟,等.茄子皮中花色苷提取方法的比较及其抗氧化活性研究[J].中国食品学报,2017,17(1):92-99.
[3]罗赟,陈宗玲,宋卫堂,等.草莓果实花色苷成分组成鉴定及分析[J].中国农业大学学报,2014,19(5):86-94.
[4]吕昱,严敏.紫薯花色苷的生理功能及分离纯化研究进展[J].食品与机械,2013,19(4):250-253,257.
[5]魏一枝,邓洁红,王维茜,等.花色苷纯化分离及鉴定研究进展[J].包装与食品机械,2014,32(1):50-54.
[6] Luque-rodriguez J M, Castro L D, Perez-juan P. Dynamic superheated liquid extraction of anthocyanins and other phenolics from red grape skins of winemaking residues[J]. Bioresource Technology,2007,98(14):2705-2713.
[7]吴斌,张玉丽,程琳琳,等.鲜食葡萄花色苷的研究进展[J].现代食品科技,2012,28(4):441-444.
[8]凌关庭.食品添加剂手册[M].北京:中国化学出版社,1997:543-545.
[9] Liang Z, Wu B, Fan P, et al. Anthocyanin composition and content in grape berry skin in Vitis germplasm[J]. Food Chemistry,2008,111(4):837-844.
[10]孙磊,樊秀彩,张颖,等.部分中国野生葡萄果皮花色苷组分分析[J].果树学报,2015,32(6):1143-1151.
[11]周君,陈宗玲,张琼,等.套袋对桃果实成熟过程中酚酸类和类黄酮类物质积累的影响[J].园艺学报,2009,36(12):1717-1724.
[12]王燕,陈学森,刘大亮,等.‘紫红1号’红肉苹果果肉抗氧化性及花色苷分析[J].园艺学报,2012,39(10):1991-1998.
[13] Xiao L, Min X, Yun L, et al. The effect of RNAi-induced silencing of FaDFR on anthocyanin metabolism in strawberry(Fragaria×ananassa)fruit[J]. Scientia Horticulturae,2013,160:123-128.
[14]肖敏.FaANS基因表达与草莓果实花色苷代谢的关系[D].北京:中国农业大学,2012.
[15] Anderson Q M, Joudheim M. Flavonoids:chemistry, biochemistry,and applications[M]. London:CRC Taylor&Francis Group,2006.
[16] Nardini M, Daquino M, Tomassi G, et al. Inhibition of human LDL oxidation by caffeic acid and other hydroxycinnamic acid derivatives[J]. Free Radical Biology and Medicine,1995,19(5):541-552.
[17] Honda T, Saito N. Recent progress in the chemistry of polyacylated anthocyanins as flower color pigments[J]. Heterocycles,2002,56(1):633-692.
[18] Nakayama T, Suzuki H, Nishino T. Anthocyanin acyltransferases:Specificities, mechanism, phylogenetics, and applications[J].Journal of Molecular Catalysis B:Enzymatic,2003,23(2):117-132.
[19]肖慧琳,张珍珍,朱保庆,等.川西北干旱河谷地区赤霞珠葡萄果实花色苷的积累[J].中外葡萄与葡萄酒,2012,3:16-21.
[20]张珍珍,邓玉杰,陈新军,等.新疆伊犁地区赤霞珠葡萄成熟过程中花色苷组成及含量变化研究[J].现代食品科技,2018,34(2):1-6.
[21] Podsdek A, Redzynia M, Klewicka E, et al. Matrix effects on the stability and antioxidant activity of red cabbage anthocyanins under simulated gastrointestinal digestion[J]. BioMed Research International,2014(2):1-11.
[22] Juadjur A, Mohn C, Schantz M, et al. Fractionation of an anthocyanin-rich bilberry extract and in vitro antioxidative activity testing[J]. Food Chemistry,2015,167(1):418-424.
[23] Santos-buelga C, Escribano-bailon M T. Anthocyanin copigmentation-evaluation, mechanisms and implications for the colour of red wines[J]. Current Organic Chemistry,2012,16(6):715-723.
[24]李丹,沈才洪,马懿.夏黑葡萄花色苷的提取及抗氧化活性研究[J].应用化工,2016,45(8):1418-1423.
[25]许萍,乔勇进,周慧娟,等.固体二氧化氯保鲜剂对夏黑葡萄保鲜效果的影响[J].食品科学,2012,33(10):282-286.