柴胡果实化学成分及其质量标准研究
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摘要
柴胡果实为伞形科柴胡属(Bupleurum)植物柴胡Bupleurum chinense DC.的干燥成熟果实。未见柴胡果实系统研究的报道。本文对柴胡果实鉴别和化学成分进行了系统研究,并对其它品种的柴胡果实进行了品种鉴别和化学成分分析研究,为柴胡果实的品种鉴定、开发和应用,奠定了科学基础。主要研究内容和结果如下:
一.利用性状、显微、理化鉴别等方法,研究了我国北方常见的柴胡果实、狭叶柴胡果实、银州柴胡果实、引种日本31号柴胡果实的鉴别方法和主要特征。
二.对柴胡果实进行系统的化学成分研究,从柴胡果实的乙醇提取物中分离得到28个单体化合物,利用理化性质、~1NMR、~(13)CNMR、H-HCOSY、HMBC、HQSC、DEPT、FAB-MS、IR等方法、技术,确定了其化学结构。3-(3-环己基-丙基)-木犀草素(1),槲皮素(2)、山萘酚(3)、3,5,7-三羟基-3′,4′-甲氧基黄酮(4)、异鼠李素(5)、异甘草素(6)、芦丁(7)、β-D-吡喃葡萄糖(1→4)-β-D-吡喃葡萄糖豆甾醇(8)、醋酸铵(9)、蔗糖(10)、葡萄糖(11)、蒈诺菲林(12)、乌苏酸(13)、胡萝卜苷(14)、己酸甲酯(15)、二十七碳酸(16)、亚油酸三甘油酯(17)、油酸单甘油酯(18)、豆甾醇(19)、乙酰豆甾醇(20)、β-谷甾醇(21)、α-菠甾醇(22)、12-烯-齐墩果-3,28-二醇(23)、1-十九烷醇(24)、油酸(25)、齐墩果酸(26)、n-十五烷(27)、十五碳-6-醇(28)。其中化合物1为新化合物,其余27个已知化合物均为首次从柴胡果实中分离得到的单体化合物。
GC-MS分析确定了柴胡果实挥发油51个化合物、柴胡果实精油(SFE提取)73个化合物;GC-MS分析确定了柴胡果实油26个化合物(包括4个脂肪酸);HPLC分析了柴胡果实17种氨基酸。
三.系统分析柴胡果实的化学成分的含量。柴胡果实和狭叶柴胡果实挥发油提取率(水气蒸馏法)分别为0.3%和0.25%,柴胡果实精油SFE的提取率为6.60%。
柴胡果实和狭叶柴胡果实油提取率分别为27.6%和23.6%。
凯氏定氮法测得柴胡果实、狭叶柴胡果实和银州柴胡果实的粗蛋白总量分别为22.07%、18.22%、17.29%;HPLC法测得柴胡果实、狭叶柴胡果实和银州柴胡果实的17种氨基酸的总量分别为19.49%、17.53%和14.96%。
柴胡果实、狭叶柴胡果实和引种日本31号柴胡果实的总黄酮含量(紫外-可见分光光度法)分别为2.3-2.7%、4.6%,1.1%;柴胡果实、狭叶柴胡果实、银州柴胡果实和引种日本31号柴胡果实的芦丁含量(HPLC法)分别为0.5363%、1.4211%、0.6266%、0.0887%。
柴胡果实、狭叶柴胡果实、银州柴胡果实和引种日本31柴胡果实的蒈诺
The fruits of Chaihu is the dried ripe fruits of the plants of Bupleurum chinenseDC. Systemic research of the fruits of Chaihu has not been studied previously. This doctoral dissertation deals with the identification and the phytochemical studies on the fruits of Chaihu.1. Studies on the methods of the identification of the fruits of Bupleurum chinense DC, B. scorzonerifolium Willd. , B. yinchowenseShan et Y.Li and Japan No. 31 Chaihu by the figure, microstructure, physical and chemical characteristics.2. The systemic study on the chemical constituents of the fruits of Chaihu. 28 compounds were got from the ethanol extraction of the fruits of Chaihu, its chemical structure were confirmed by the physical chemistry character ~1NMR, ~(13)CNMR, H-HCOSY, HMBC, HQSC, DEPT, FAB-MS, IR. 3-(3-Cyclohexyl-propyl)-luteolin (Compound 1), in addition ,known 27 compounds were Quercetin (Compound 2), Kaempferol (Compound 3), 3, 5 , 7-Trihydroxy-3 ' , 4 ' -dimethoxy-flavone(Compound 4) ,Isorhamnetin (Compound 5),Isoliquiritigenin(Compound 6) ,Rutin(Compound 7), Stigmasterol-3-0-β -D-glucopyranosyl-(1—4)-glucopyranoside (Compound 8) , Ammonium acetate(Compound 9) , Sucrose(Compound 10) , Glucose (Compound 11) , kaerophyllin (Compound 12) , Ursolic acid(Compound 13) , Daucosterol(Compound 14), Caproic acid methylester(Compound 15) , heptacosanoic acid(Compound 16), Glycerol trilinolet(Compound 17) , Glycerol oleate(Compound 18), Stigmasterol(Compound 19) , Stigmasterol acetate(Compound 20), β-Sitosterol(Compound 21), α -Spinasterol (Compound 22) , 12-Olean-3, 28-diol (Compound 23) , 1- Nonadecanol (Compound 24) , Oleic acid(Compound 25) , Oleanolic acid (Compound 26) , n-Pentadecane (Compound 27) , pentadecane-6-ol (Compound 28). Compound 1 is a new compound, the other 27 compounds are got from the fruits of Chaihu at the first times.51 compounds from the volatile oils and 73 compounds from essential oil (SFE) were separate confirmed by GC-MS;27 compounds (included 5 fatty acids) from Chaihu oil were separate confirmed by GC-MS;17 amino acids were separate confirmed by HPLC.
3. The yield of the volatile oil of the fruits of Bupleurum chinense DC. and B. scorzonerifoliumViilld. were 0. 3% and 0. 25% by vapour, the yield of essential oil from the fruits of Bupleurum chinense DC. by SFE was 6. 60%.The yield of the Chaihu oil of the fruits of Bupleurum chinense DC. and B. scorzoneri folium Wi lid. were 27. 6% and 23. 6%.The totale coarse protein of the fruits of Bupleurum chinense DC. and B. scorzoneri folium Wi lid. and B. yinchowense Shan et Y.Li parting were 22.07%, 18.22% and 17.29%; The totale aminophenol (17 amino acids analyzing) parting were 19.49%, 17.53% and 14.96%.The contents of totale flavones of the fruits of Bupleurum chinense DC. and B. scorzoneri folium Willd. and Japan No. 31 were 2. 3~2. 7%, 4.6%, 1.1% by UV & Vis spectrophotometry. The contents of rutin of the fruits of Bupleurum chinense DC., B. scorzoneri folium Willd., B. yinchowense Shan et Y. Li and Japan No. 31 were 0. 5363%, 1.4211%, 0.6266%, 0. 0887% by HPLC.The contents of kaerophyllin of the fruits of Bupleurum chinense VC. , B. scorzoneri foil urn Willd., B. yinchowense Shan et Y. Li and Japan No. 31 were 0.0625%, 0.0510%, 0.0101% and trace by HPLC.4.The chemical configuration of quercetin and rutin were changed by chemical reaction using epoxy propane, two new compounds of Hydroxypropyl quercetin and Hydroxypropyl rutin were got.5. According to the research result, the drafted standard plan of the fruits of Chaihu was gived.
一.利用性状、显微、理化鉴别等方法,研究了我国北方常见的柴胡果实、狭叶柴胡果实、银州柴胡果实、引种日本31号柴胡果实的鉴别方法和主要特征。
二.对柴胡果实进行系统的化学成分研究,从柴胡果实的乙醇提取物中分离得到28个单体化合物,利用理化性质、~1NMR、~(13)CNMR、H-HCOSY、HMBC、HQSC、DEPT、FAB-MS、IR等方法、技术,确定了其化学结构。3-(3-环己基-丙基)-木犀草素(1),槲皮素(2)、山萘酚(3)、3,5,7-三羟基-3′,4′-甲氧基黄酮(4)、异鼠李素(5)、异甘草素(6)、芦丁(7)、β-D-吡喃葡萄糖(1→4)-β-D-吡喃葡萄糖豆甾醇(8)、醋酸铵(9)、蔗糖(10)、葡萄糖(11)、蒈诺菲林(12)、乌苏酸(13)、胡萝卜苷(14)、己酸甲酯(15)、二十七碳酸(16)、亚油酸三甘油酯(17)、油酸单甘油酯(18)、豆甾醇(19)、乙酰豆甾醇(20)、β-谷甾醇(21)、α-菠甾醇(22)、12-烯-齐墩果-3,28-二醇(23)、1-十九烷醇(24)、油酸(25)、齐墩果酸(26)、n-十五烷(27)、十五碳-6-醇(28)。其中化合物1为新化合物,其余27个已知化合物均为首次从柴胡果实中分离得到的单体化合物。
GC-MS分析确定了柴胡果实挥发油51个化合物、柴胡果实精油(SFE提取)73个化合物;GC-MS分析确定了柴胡果实油26个化合物(包括4个脂肪酸);HPLC分析了柴胡果实17种氨基酸。
三.系统分析柴胡果实的化学成分的含量。柴胡果实和狭叶柴胡果实挥发油提取率(水气蒸馏法)分别为0.3%和0.25%,柴胡果实精油SFE的提取率为6.60%。
柴胡果实和狭叶柴胡果实油提取率分别为27.6%和23.6%。
凯氏定氮法测得柴胡果实、狭叶柴胡果实和银州柴胡果实的粗蛋白总量分别为22.07%、18.22%、17.29%;HPLC法测得柴胡果实、狭叶柴胡果实和银州柴胡果实的17种氨基酸的总量分别为19.49%、17.53%和14.96%。
柴胡果实、狭叶柴胡果实和引种日本31号柴胡果实的总黄酮含量(紫外-可见分光光度法)分别为2.3-2.7%、4.6%,1.1%;柴胡果实、狭叶柴胡果实、银州柴胡果实和引种日本31号柴胡果实的芦丁含量(HPLC法)分别为0.5363%、1.4211%、0.6266%、0.0887%。
柴胡果实、狭叶柴胡果实、银州柴胡果实和引种日本31柴胡果实的蒈诺
The fruits of Chaihu is the dried ripe fruits of the plants of Bupleurum chinenseDC. Systemic research of the fruits of Chaihu has not been studied previously. This doctoral dissertation deals with the identification and the phytochemical studies on the fruits of Chaihu.1. Studies on the methods of the identification of the fruits of Bupleurum chinense DC, B. scorzonerifolium Willd. , B. yinchowenseShan et Y.Li and Japan No. 31 Chaihu by the figure, microstructure, physical and chemical characteristics.2. The systemic study on the chemical constituents of the fruits of Chaihu. 28 compounds were got from the ethanol extraction of the fruits of Chaihu, its chemical structure were confirmed by the physical chemistry character ~1NMR, ~(13)CNMR, H-HCOSY, HMBC, HQSC, DEPT, FAB-MS, IR. 3-(3-Cyclohexyl-propyl)-luteolin (Compound 1), in addition ,known 27 compounds were Quercetin (Compound 2), Kaempferol (Compound 3), 3, 5 , 7-Trihydroxy-3 ' , 4 ' -dimethoxy-flavone(Compound 4) ,Isorhamnetin (Compound 5),Isoliquiritigenin(Compound 6) ,Rutin(Compound 7), Stigmasterol-3-0-β -D-glucopyranosyl-(1—4)-glucopyranoside (Compound 8) , Ammonium acetate(Compound 9) , Sucrose(Compound 10) , Glucose (Compound 11) , kaerophyllin (Compound 12) , Ursolic acid(Compound 13) , Daucosterol(Compound 14), Caproic acid methylester(Compound 15) , heptacosanoic acid(Compound 16), Glycerol trilinolet(Compound 17) , Glycerol oleate(Compound 18), Stigmasterol(Compound 19) , Stigmasterol acetate(Compound 20), β-Sitosterol(Compound 21), α -Spinasterol (Compound 22) , 12-Olean-3, 28-diol (Compound 23) , 1- Nonadecanol (Compound 24) , Oleic acid(Compound 25) , Oleanolic acid (Compound 26) , n-Pentadecane (Compound 27) , pentadecane-6-ol (Compound 28). Compound 1 is a new compound, the other 27 compounds are got from the fruits of Chaihu at the first times.51 compounds from the volatile oils and 73 compounds from essential oil (SFE) were separate confirmed by GC-MS;27 compounds (included 5 fatty acids) from Chaihu oil were separate confirmed by GC-MS;17 amino acids were separate confirmed by HPLC.
3. The yield of the volatile oil of the fruits of Bupleurum chinense DC. and B. scorzonerifoliumViilld. were 0. 3% and 0. 25% by vapour, the yield of essential oil from the fruits of Bupleurum chinense DC. by SFE was 6. 60%.The yield of the Chaihu oil of the fruits of Bupleurum chinense DC. and B. scorzoneri folium Wi lid. were 27. 6% and 23. 6%.The totale coarse protein of the fruits of Bupleurum chinense DC. and B. scorzoneri folium Wi lid. and B. yinchowense Shan et Y.Li parting were 22.07%, 18.22% and 17.29%; The totale aminophenol (17 amino acids analyzing) parting were 19.49%, 17.53% and 14.96%.The contents of totale flavones of the fruits of Bupleurum chinense DC. and B. scorzoneri folium Willd. and Japan No. 31 were 2. 3~2. 7%, 4.6%, 1.1% by UV & Vis spectrophotometry. The contents of rutin of the fruits of Bupleurum chinense DC., B. scorzoneri folium Willd., B. yinchowense Shan et Y. Li and Japan No. 31 were 0. 5363%, 1.4211%, 0.6266%, 0. 0887% by HPLC.The contents of kaerophyllin of the fruits of Bupleurum chinense VC. , B. scorzoneri foil urn Willd., B. yinchowense Shan et Y. Li and Japan No. 31 were 0.0625%, 0.0510%, 0.0101% and trace by HPLC.4.The chemical configuration of quercetin and rutin were changed by chemical reaction using epoxy propane, two new compounds of Hydroxypropyl quercetin and Hydroxypropyl rutin were got.5. According to the research result, the drafted standard plan of the fruits of Chaihu was gived.
引文
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