栀子的化学成分研究  

Research on chemical constituents of Gardenia jasminoides

作　　者：李海波[1,2] 马金凤 庞倩倩 梅玉丹 王振中[2] 姚新生[1] 于洋[1] LI Hai-bo;MA Jin-feng;PANG Qian-qian;MEI Yu-dan;WANG Zhen-zhong;YAO Xin-sheng;YU Yang(Institute of Traditional Chinese Medicine and Natural Products,Jinan University,Guangzhou 510632,China;State Key Laboratory of New-tech for Chinese Medicine Pharmaceutical Process,Kanion Pharmaceutical Co.,Ltd.,Lianyungang 222001,China)

机构地区：[1]暨南大学中药及天然药物研究所,广东广州510632 [2]江苏康缘药业股份有限公司中药制药过程新技术国家重点实验室,江苏连云港222001

出　　处：《中草药》2020年第22期5687-5697,共11页Chinese Traditional and Herbal Drugs

基　　金：重大新药创制科技重大专项“十三五”计划(2018ZX09711001-008-005);国家自然科学基金重点项目(81630097)。

摘　　要：目的对中药栀子Gardenia jasminoides的主要化学成分进行系统研究。方法综合应用各种现代色谱分离技术对栀子环烯醚萜苷富集部位进行系统的化学成分研究,根据化合物的理化性质和核磁共振波谱数据进行结构鉴定。结果经UPLC-Q/TOF-MS快速分析发现栀子果实60%乙醇提取物经HP-20大孔吸附树脂30%乙醇水洗脱部位为环烯醚萜苷类化合物富集部位,从中分离鉴定了31个化合物,分别为2’-O-[(E)-对香豆酰基]-栀子新苷(1)、6’-O-[(E)-芥子酰基]-栀子新苷(2)、7-去氧栀子新苷(3)、tarenninoside C(4)、2’-O-coumaroylmussaenosidic acid(5)、10-0-咖啡酰基去乙酰基交让木苷(6)、6’-O-[(E)-芥子酰基]-京尼平苷(7)、京尼平-1-O-β-D-龙胆二糖苷(8)、京尼平苷(9)、7-脱氧-8-表马钱苷酸(10)、断氧化马钱苷酸(11)、gardenamide A(12)、6’-O-trans-sinapoyljasminoside B(13)、epijasminoside A(14)、jasminodiol(15)、6’-O-trans-sinapoyljasminoside L(16)、3-(β-D-glucopyranosyloxymethyl)-2,4,4-trimethyl-2-cyclohexen-1-one(17)、jasminoside C(18)、芥子酸(19)、咖啡酸(20)、没食子酸甲酯(21)、C-藜芦酰基乙二醇(22)、β-hydroxypropiosyringone(23)、3-羟基-1-(3-甲氧基-4-羟基苯基)丙烷-1-酮(24)、threo-guaiacylglycerol-8’-vanillic acid ether(25)、1,2-双-(4-羟基-3-甲氧基苯基)-1,3-丙二醇(26)、反-2,3,5,4,-四羟基二苯乙烯-2-O-β-D-葡萄糖苷(27)、1-芥子酰基-O-β-D-吡喃葡萄糖苷(28)、1,3,5-三甲氧基苯(29)、芦丁(30)、glycyrrhisoflavone(31)。结论化合物1~12为环烯醚萜苷类化合物,13~18为单萜苷类化合物,6、10、22~29和31为首次从栀子果实中分离得到。Objective To study the main constituents from Gardenia jasminoides.Method In this study,the chemical constituents of enrichment fraction of iridoid glycosides were isolated by various chromatographic techniques and their structures were elucidated by spectroscopic analyses and comparison of NMR data with those reported in literatures.Results The 60%ethanol extract of G.jasminoides was subjected to HP-20 macroporous adsorption resin CC to yield 30%ethanol fraction(GJ-2,UPLC-Q/TOF-MS method was used to identify the enrichment fraction of iridoid glycosides).Thirty-one compounds were obtained and characterized as 2′-O-trans-coumaroylgardoside(1),6′-O-trans-sinapoylgardoside(2),7-deoxygardoside(3),tarenninoside C(4),2′-Ocoumaroylmussaenosidic acid(5),10-O-caffeoyl deacetyldaphylloside(6),6′-O-trans-sinapoylgeniposide(7),genipin-1-O-β-D-gentiobioside(8),geniposide(9),7-deoxy-8-epiloganicacid(10),secologanoside(11),gardenamide A(12),6′-O-transsinapoyljasminoside B(13),epijasminoside A(14),jasminodiol(15),6′-O-trans-sinapoyljasminoside L(16),3-(β-D-glucopyranosyloxymethyl)-2,4,4-trimethyl-2-cyclohexen-1-one(17),jasminoside C(18),sinapinic acid(19),caffeic acid(20),methyl gallate(21),C-veratroylglucol(22),β-hydroxypropiosyringone(23),3-hydroxy-1-(4-hydroxy-3-methoxyphenoyl)propan-1-one(24),threo-guaiacylglycerol-8′-vanillic acid ether(25),1,2-bis-(4-hydroxy-3-methoxyphenyl)-1,3-propanediol(26),trans-2,3,5,4′-tetrahydroxystilbene-2-β-D-glucoside(27),1-sinapoyl-β-D-glucopyranoside(28),1,3,5-trimethoxybenzene(29),rutin(30),and glycyrrhisoflavone(31),respectively.Conclusion Compounds 1—12 are iridoid glycosides and 13—18 are monoterpenoid glycosides.Compounds 6,10,22—29,and 31 were identified from Gardeniae Fructus for the first time.

关 键 词：栀子 化学成分 环烯醚萜苷类 10-O-咖啡酰基去乙酰基交让木苷 7-脱氧-8-表马钱苷酸 C-藜芦酰基乙二醇 

分 类 号：R284.1[医药卫生—中药学]