野生黑枸杞果实中酚类物质的组成分析
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摘要
以产自宁夏的野生黑枸杞鲜果为实验材料,采用高效液相色谱-三重四极杆串联质谱联用仪对黑枸杞果实中的酚类物质组成进行定性、定量分析。结果显示,黑枸杞果实富含酚类物质,共鉴定到花色苷类物质20种,非花色苷酚类物质16种。其中,最主要的花色苷为甲基花翠素-3,5-O-双葡萄糖苷和一些6-O-香豆酰化衍生的3-O-单糖苷花色苷,而最主要的非花色苷酚类物质为绿原酸等一系列羟基肉桂酸,与葡萄、蓝莓等富含酚类物质的深色水果有极大不同,具有典型的种属特异性。本研究将为黑枸杞的鲜果消费以及产品开发提供一定的理论基础。
In this research, the phenolic composition of fresh fruit of wild black wolfberry from Ningxia autonomous region was qualitatively and quantitatively analyzed by high-performance liquid chromatography/triple-quadrupole tandem mass spectrometry(HPLC-QqQ-MS/MS). Our data showed that black wolfberries were rich in phenolic compounds including20 anthocyanins and 16 non-anthocyanin phenolics identified. Among them, the main anthocyanins were petunidin-3,5-O-diglucoside and some 6-O-coumaroyl acylated 3-O-glucosidic anthocyanins, and the main non-anthocyanin phenolics were a series of hydroxy cinnamic acids such as chlorogentic acid, which were quite different from those present in some other dark-colored fruits rich in phenolics such as grapes and blueberries. The composition of anthocyanins was typically species specific. The present study provides a theoretical basis for the consumption of fresh black wolfberries as well as the development of black wolfberry products.
In this research, the phenolic composition of fresh fruit of wild black wolfberry from Ningxia autonomous region was qualitatively and quantitatively analyzed by high-performance liquid chromatography/triple-quadrupole tandem mass spectrometry(HPLC-QqQ-MS/MS). Our data showed that black wolfberries were rich in phenolic compounds including20 anthocyanins and 16 non-anthocyanin phenolics identified. Among them, the main anthocyanins were petunidin-3,5-O-diglucoside and some 6-O-coumaroyl acylated 3-O-glucosidic anthocyanins, and the main non-anthocyanin phenolics were a series of hydroxy cinnamic acids such as chlorogentic acid, which were quite different from those present in some other dark-colored fruits rich in phenolics such as grapes and blueberries. The composition of anthocyanins was typically species specific. The present study provides a theoretical basis for the consumption of fresh black wolfberries as well as the development of black wolfberry products.
引文
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[24]WANG Y,ZHAO L,WANG D,et al.Anthocyanin-rich extracts from blackberry,wild blueberry,strawberry,and chokeberry:antioxidant activity and inhibitory effect on oleic acid-induced hepatic steatosis in vitro[J].Journal of the Science of Food&Agriculture,2016,96(7):2494-2503.DOI:10.1002/jsfa.7370.
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[27]WANG G F,SHI L P,REN Y D,et al.Anti-hepatitis B virus activity of chlorogenic acid,quinic acid and caffeic acid in vivo and in vitro[J].Antiviral Research,2009,83(2):186-190.DOI:10.1016/j.antiviral.2009.05.002.
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[29]ZHAO Y Y,WANG J K,BALLEVRE O,et al.Antihypertensive effects and mechanisms of chlorogenic acids[J].Hypertension Research,2012,35(4):370-374.DOI:10.1038/hr.2011.195.
[30]刘凤兰,王建友,韩宏伟,等.不同处理方法对“黑杞1号”枸杞几种功能性成分的影响[J].北方园艺,2015(21):158-160.DOI:10.11937/bfyy.201521041.
[31]赵秀玲.黑枸杞生理活性成分研究进展[J].食品与生物技术学报,2016,35(6):561-568.DOI:10.3969/j.issn.1673-1689.2016.06.001.
[2]DHAR P,TAYADE A,BALLABH B,et al.Lycium ruthenicum Murray:a less-explored but high-value medicinal plant from transhimalayan cold deserts of Ladakh,India[J].Plant Archives,2011,11(2):583-586.
[3]任小娜,曾俊,王玉涛.黑枸杞的植物化学成分及生物活性研究现状[J].食品工业,2014,35(11):231-235.
[4]PENG Q,LIU H,LEI H,et al.Relationship between structure and immunological activity of an arabinogalactan from Lycium ruthenicum[J].Food Chemistry,2016,194:595-600.DOI:10.1016/j.foodchem.2015.08.087.
[5]蔺定运,甘青梅.黑枸杞果实色素的初步研究[J].中国食品添加剂,1995(2):5-9.
[6]BASTIANETTO S,ZHENG W H,QUIRION R.Neuroprotective abilities of resveratrol and other red wine constituents against nitric oxide-related toxicity in cultured hippocampal neurons[J].British Journal of Pharmacology,2000,131(4):711-720.DOI:10.1038/sj.bjp.0703626.
[7]BURNS J,GARDNER P T,O’NEIL J,et al.Relationship among antioxidant activity,vasodilation capacity,and phenolic content of red wines[J].Journal of Agricultural and Food Chemistry,2000,48(2):220-230.DOI:10.1021/jf9909757.
[8]CAROCHO M,FERREIRA I C.The role of phenolic compounds in the fight against cancer:a review[J].Anti-Cancer Agents in Medicinal Chemistry(Formerly Current Medicinal Chemistry-Anti-Cancer Agents),2013,13(8):1236-1258.DOI:10.2174/18715206113139990301.
[9]ALVES M J,FERREIRA I C,FROUFE H J,et al.Antimicrobial activity of phenolic compounds identified in wild mushrooms,SARanalysis and docking studies[J].Journal of Applied Microbiology,2013,115(2):346-357.DOI:10.1111/jam.12196.
[10]DOWNEY M O,MAZZA M,KRSTIC M P.Development of a stable extract for anthocyanins and flavonols from grape skin[J].American Journal of Enology and Viticulture,2007,58(3):358-364.
[11]LI S Y,HE F,ZHU B Q,et al.A systematic analysis strategy for accurate detection of anthocyanin pigments in red wines[J].Rapid Communications in Mass Spectrometry,2016,30(13):1619-1626.DOI:10.1002/rcm.7584.
[12]ZHENG J,DING C X,WANG L S,et al.Anthocyanins composition and antioxidant activity of wild Lycium ruthenicum Murr.from Qinghai-Tibet plateau[J].Food Chemistry,2011,126(3):859-865.DOI:10.1016/j.foodchem.2010.11.052.
[13]HE F,LIANG N N,MU L,et al.Anthocyanins and their variation in red wines I.Monomeric anthocyanins and their color expression[J].Molecules,2012,17(2):1571-1601.DOI:10.3390/molecules17021571.
[14]SILVáN J M,REGUERO M,PASCUAL T S.A protective effect of anthocyanins and xanthophylls on UVB-induced damage in retinal pigment epithelial cells[J].Food&Function,2016,7(2):1067-1076.DOI:10.1039/c5fo01368b.
[15]GOULD K,DAVIES K M,WINEFIELD C.Anthocyanins:biosynthesis,functions,and applications[M].Berlin:Springer Science&Business Media,2009:6-7.DOI:10.1111/tpj.12153.
[16]闫亚美,戴国礼,冉林武,等.2008不同产地野生黑枸杞资源果实多酚组成分析[J].中国农业科学,2014,47(22):4540-4550.DOI:10.3864/j.issn.0578-1752.2014.22.020.
[17]谭亮,董琦,曹静亚,等.黑枸杞中花色苷的提取与结构鉴定[J].天然产物研究与开发,2014,26(11):1797-1802.DOI:10.16333/j.1001-6880.2014.11.006.
[18]张小敏,冉林武,曹有龙,等.黑枸杞花色苷HPLC半定量分析[J].食品工业,2014,35(11):207-209.
[19]林丽,李进,丁成丽.高效液相色谱法测定黑果枸杞果实中花色苷的含量[J].食品科学,2013,34(6):164-166.DOI:10.7506/spkx1002-6630-201306036.
[20]JIN H L,LIU Y F,YANG F,et al.Characterization of anthocyanins in wild Lycium ruthenicum Murray by HPLC-DAD/QTOF-MS/MS[J].Analytical Methods,2015,7(12):4947-4956.DOI:10.1039/C5AY00612K.
[21]HU N,ZHENG J,LI W C,et al.Isolation,stability,and antioxidant activity of anthocyanins from Lycium ruthenicum Murray and Nitraria tangutorum Bobr of Qinghai-Tibetan plateau[J].Separation Science and Technology,2014,49(18):2897-906.DOI:10.1080/01496395.2014.943770.
[22]GARRIDO J,BORGES F.Wine and grape polyphenols:a chemical perspective[J].Food Research International,2013,54(2):1844-1858.DOI:10.1016/j.foodres.2013.08.002.
[23]SANG J,MA Q,LI B,et al.An approach for extraction,purification,characterization and quantitation of acylated-anthocyanins from Nitraria tangutorun Bobr.fruit[J].Journal of Food Measurement&Characterization,2018,12(1):45-55.DOI:10.1007/s11694-017-9615-1.
[24]WANG Y,ZHAO L,WANG D,et al.Anthocyanin-rich extracts from blackberry,wild blueberry,strawberry,and chokeberry:antioxidant activity and inhibitory effect on oleic acid-induced hepatic steatosis in vitro[J].Journal of the Science of Food&Agriculture,2016,96(7):2494-2503.DOI:10.1002/jsfa.7370.
[25]楼舒婷.黑枸杞的活性成分和挥发性组分研究[D].杭州:浙江大学,2015:18-19.
[26]陈晨,文怀秀,赵晓辉,等.固相萃取快速测定黑枸杞果汁中酚酸类化合物[J].中国中药杂志,2011,36(7):896-898.DOI:10.4268/cjcmm20110716.
[27]WANG G F,SHI L P,REN Y D,et al.Anti-hepatitis B virus activity of chlorogenic acid,quinic acid and caffeic acid in vivo and in vitro[J].Antiviral Research,2009,83(2):186-190.DOI:10.1016/j.antiviral.2009.05.002.
[28]SHI H T,DONG L,DANG X Y,et al.Effect of chlorogenic acid on LPS-induced proinflammatory signaling in hepatic stellate cells[J].Inflammation Research,2013,62(6):581-587.DOI:10.1007/s00011-013-0610-7.
[29]ZHAO Y Y,WANG J K,BALLEVRE O,et al.Antihypertensive effects and mechanisms of chlorogenic acids[J].Hypertension Research,2012,35(4):370-374.DOI:10.1038/hr.2011.195.
[30]刘凤兰,王建友,韩宏伟,等.不同处理方法对“黑杞1号”枸杞几种功能性成分的影响[J].北方园艺,2015(21):158-160.DOI:10.11937/bfyy.201521041.
[31]赵秀玲.黑枸杞生理活性成分研究进展[J].食品与生物技术学报,2016,35(6):561-568.DOI:10.3969/j.issn.1673-1689.2016.06.001.