盐肤木根的化学成分及抗氧化活性研究
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摘要
目的研究盐肤木(Rhus chinensis Mill.)根的化学成分及其抗氧化活性。方法应用多种色谱技术对盐肤木根水提醇沉提取物进行分离纯化,采用一维核磁共振(1D-NMR)及高分辨电喷雾质谱(HR-ESI-MS)等波谱方法鉴定化合物结构,并用1,1-二苯基-2-三硝基苯肼(DPPH)法评价其抗氧化活性。结果从总提物中分离得到20个化合物(包括2个鞣质,9个酚酸及9个黄酮),分别鉴定为1,2,3,4,6-五-O-没食子酰基-β-D-葡萄糖(1)、1,2,3,6-四-O-没食子酰基-β-D-葡萄糖(2)、没食子酸(3)、没食子酸甲酯(4)、没食子酸乙酯(5)、鞣花酸(6)、原儿茶醛(7)、原儿茶酸(8)、苔黑酚葡萄糖苷(9)、对羟基苯甲酸(10)、盐肤木内酯A(11)、芦丁(12)、漆黄素(13)、山柰酚(14)、山柰酚-3-O-芸香糖苷(15)、紫铆亭(16)、二氢漆黄素(17)、(+)-儿茶素(18)、根皮素(19)、根皮苷(20)。其中1～7、12～14抗氧化活性IC50值依次为2.61、5.54、8.75、8.99、9.36、10.86、14.60、16.68、18.88、27.52μmol·L~(-1),均优于阳性对照药维生素C。结论 2、7、10、15、16、18系首次从该植物分离,且1～7、12～14抗氧化活性良好。
Objective To study the chemical compositions of root of the Rhus chinensis Mill. and their anti-oxidative activities.Methods The root of R.chinensis was subjected to water extraction and alcohol precipitation to obtain a total extract.Compounds were purified by column chromatography on silica gel as well as ODS. Their structures were identified by spectroscopic methods including 1 D-NMR,HR-ESI-MS and comparison with references.Moreover,anti-oxidative activities of all the isolates were evaluated by DPPH radical scavenging assay. Results Twenty compounds,including two tannins,nine phenolic acids as well as nine flavonoids,were isolated from R.chinensis Mill.,which were identified as pentagalloylglucose( 1),teragalloylglucose( 2),gallic acid( 3),methyl gallate( 4),ethyl gallate( 5),ellagic acid( 6),protocatechuic aldehyde( 7),protocatechuic acid( 8),orcinol glucoside( 9),p-hydroxybenzoic acid( 10),rhuscholide A( 11),rutin( 12),fisetin( 13),kaempferol( 14),kaemferol-3-O-β-D-rutinoside( 15),butin( 16),fustin( 17),( +)-catechin( 18),phloretin( 19) and phloridzin( 20).Compounds 1～ 7 and 12～ 14 show anti-oxidative activities,with IC50 values of2.61,5.54,8.75,8.99,9.36,10.86,14.60,16.68,18.88,27.52 μmol·L~(-1),respectively,which were better than the positive control vitamin C.Conclusion Compounds 2,7,10,15,16,18 were gained from R. chinensis for the first time. Moreover,compounds 1 ～ 7 and 12 ～ 14 showed anti-oxidative activities might be useful in the treatment of CHD for their anti-oxidative activities.
Objective To study the chemical compositions of root of the Rhus chinensis Mill. and their anti-oxidative activities.Methods The root of R.chinensis was subjected to water extraction and alcohol precipitation to obtain a total extract.Compounds were purified by column chromatography on silica gel as well as ODS. Their structures were identified by spectroscopic methods including 1 D-NMR,HR-ESI-MS and comparison with references.Moreover,anti-oxidative activities of all the isolates were evaluated by DPPH radical scavenging assay. Results Twenty compounds,including two tannins,nine phenolic acids as well as nine flavonoids,were isolated from R.chinensis Mill.,which were identified as pentagalloylglucose( 1),teragalloylglucose( 2),gallic acid( 3),methyl gallate( 4),ethyl gallate( 5),ellagic acid( 6),protocatechuic aldehyde( 7),protocatechuic acid( 8),orcinol glucoside( 9),p-hydroxybenzoic acid( 10),rhuscholide A( 11),rutin( 12),fisetin( 13),kaempferol( 14),kaemferol-3-O-β-D-rutinoside( 15),butin( 16),fustin( 17),( +)-catechin( 18),phloretin( 19) and phloridzin( 20).Compounds 1～ 7 and 12～ 14 show anti-oxidative activities,with IC50 values of2.61,5.54,8.75,8.99,9.36,10.86,14.60,16.68,18.88,27.52 μmol·L~(-1),respectively,which were better than the positive control vitamin C.Conclusion Compounds 2,7,10,15,16,18 were gained from R. chinensis for the first time. Moreover,compounds 1 ～ 7 and 12 ～ 14 showed anti-oxidative activities might be useful in the treatment of CHD for their anti-oxidative activities.
引文
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[25]柴玲,林霄,梁柏照,等.拟草果化学成分研究[J].中草药,2018,49(14):3217-3221.
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[31]李胜华,伍贤进,杨青丹,等.多穗柯化学成分研究[J].中药材,2010,33(4):549-551.
[32] BRAND-WILLIAMS W,CUVELIER M E,BERSET C.Use of a free radical method to evaluate antioxidantactivity[J]. LWT-Food Sci Technol,1995,28(1):25-30.
[2]陈伟伟,高润霖,刘力生,等.《中国心血管病报告2017》概要[J].中国循环杂志,2018,33(1):1-8.
[3]中国科学院中国植物志编辑委员会.中国植物志[M].北京:科学出版社,1980:100.
[4]沈亚英.治疗冠心病新药———舒冠通糖浆[J].中国药学杂志,1980,15(5):28.
[5] WU Y B,KUO Y H,OUYANG M A.Novel 4-(2-meth-ylphenyl)-flavan,rhusjavanins A and B,from the roots ofRhus semialata[J]. Nat Prod Res,2010,24(17):1643-1647.
[6]顾琼.五种药用植物化学与抗HIV成分研究[D].昆明:中国科学院昆明植物研究所,2007.
[7] DJAKPO O,YAO W.Rhus chinensis and Galla chinensis-folklore to modern evidence:review[J]. Phytother Res,2010,24(12):1739-1747.
[8]高洁莹.盐肤木果粕成分研究[D].长沙:湖南中医药大学,2015.
[9] TAN D,YAN Q X,MAX J.Chemical constituents of Rhuschinensis[J]. Chem Nat Compd+,2015,51(3):542-543.
[10] ZHANG C T,MA Y L,ZHAO Y X,et al.Phenolic composi-tion,antioxidant and pancreatic lipase inhibitory activities ofChinese sumac(Rhus chinensis Mill.)fruits extracted bydifferent solvents and interaction between myricetin-3-O-rhamnoside and quercetin-3-O-rhamnoside[J].Int J FoodSci Tech,2017,53(4):1045-1053.
[11] JANG S E,HYAM S R,JEONG J J,et al.Penta-O-galloyl-β-D-glucose ameliorates inflammation by inhibitingMy D88/NF-κB and My D88/MAPK signalling pathways[J].Brit J Pharmacol,2013,170(5):1078-1091.
[12] SUN M,HUANG L M,ZHU J L,et al.Screening nephro-protective compounds from cortex Moutan by mesangialcell extraction and UPLC[J]. Arch Pharm Res,2015,38(6):1044-1053.
[13]刘延麟,邓旭明,王大成,等.土耳其棓子化学成分及抑菌活性的研究[J].林产化学与工业,2008,28(4):44-48.
[14]张丽媛,任灵芝,王腾华,等.抱石莲的化学成分研究[J].中草药,2014,45(20):2890-2894.
[15]刘章彬,黄永林,杨克迪,等.南岭栲叶多酚类化学成分的分离与鉴定[J].天然产物研究与开发,2017,29(1):67-73.
[16]杨孟妮,张慧,刘娟,等.叶下珠化学成分研究[J].中草药,2016,47(20):3573-3577.
[17]王洪平,曹芳,杨秀伟.头花蓼地上部分的化学成分研究[J].中草药,2013,44(1):24-30.
[18]王召平,朱姮,李岗,等.忍冬根的化学成分与抗炎活性研究[J].中草药,2016,47(14):2412-2417.
[19]马微微,刘奂,孟思彤,等.紫椴花的化学成分研究[J].中草药,2014,45(17):2453-2456.
[20]张新渐,孙艳花,王洪云.仙茅化学成分的研究[J].中成药,2017,39(9):1869-1872.
[21]曹彦刚,郑晓珂,齐曼,等.水栀子中酚性成分研究[J].中草药,2017,48(22):4615-4619.
[22] GU Q,WANG R R,ZHANG X M,et al.A new benzofura-none and anti-HIV constituents from the stems of Rhuschinensis[J].Planta Med,2007,73(3):279-282.
[23]孙丽仁,何明珍,冯育林,等.山蜡梅叶的化学成分研究[J].中草药,2009,40(8):1214-1216.
[24] LEE S H,PARK Y H,MOON B H,et al. Substitutioneffect of hydroxyl groups on the1H and13C chemicalshifts in hydroxyflavonols[J]. Bull Korean Chem Soc,2008,29(8):1957-1960.
[25]柴玲,林霄,梁柏照,等.拟草果化学成分研究[J].中草药,2018,49(14):3217-3221.
[26]王鸣,刘培,冯煦,等.北柴胡茎叶化学成分研究(Ⅱ)[J].中药材,2009,32(3):367-369.
[27]乐佳美,吴志军,熊筱娟.大狼把草的化学成分研究[J].中国药学杂志,2014,49(20):1802-1806.
[28] SHRESTHA S,LEE D Y,PARK J H,et al. Flavonoidsfrom the fruits of Nepalese sumac(Rhus parviflora)atten-uate glutamate-induced neurotoxicity in HT22 cells[J].Food Sci Biotechnol,2013,22(4):895-902.
[29] El-RAZEK M H A.NMR assignments of four catechin ep-imers[J].Asian J Chem,2007,19(6):4867-4872.
[30]尹伟,刘金旗.木犀根中黄酮类化学成分研究[J].中药材,2016,39(7):1550-1553.
[31]李胜华,伍贤进,杨青丹,等.多穗柯化学成分研究[J].中药材,2010,33(4):549-551.
[32] BRAND-WILLIAMS W,CUVELIER M E,BERSET C.Use of a free radical method to evaluate antioxidantactivity[J]. LWT-Food Sci Technol,1995,28(1):25-30.