西藏胡黄连的化学成分研究
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摘要
西藏胡黄连( Picrorhiza scrophu1ariiflora Pennell. )为玄参科(Scrophulariaceae)多年生草本植物,药用部位为根茎,主产于西藏、云南、四川等高海拔(4400 m以上)地区。西藏胡黄连味苦、性寒,具有清热凉血、燥湿消疳的功效,主治骨蒸潮热、小儿疳疾、湿热泻痢、黄疸、吐血、衄血、目赤肿痛、疮疡肿毒等症,为清虚热之要药。
本文对西藏胡黄连的化学成分进行了研究。西藏胡黄连用95%乙醇回流提取,提取所得浸膏利用硅胶色谱、凝胶色谱和HPLC色谱等分离方法进行分离提纯,从中分离得到了42个化合物。通过理化性质、化学反应以及波谱分析,鉴定了其中35个化合物的结构。
在已分离并鉴定出结构的35个化合物中,首次分离得到10个新化合物,分别为苯乙醇苷类和环烯醚萜苷类化合物:藏黄连苷H (scroside H)(1)、藏黄连苷Ⅰ(scrosideⅠ)(2)、藏黄连环烯醚萜苷Ⅰ(picrogentiosideⅠ)(3)、藏黄连环烯醚萜苷Ⅱ(picrogentiosideⅡ)(4)、藏黄连环烯醚萜苷A(picrogentioside A)(5)、藏黄连环烯醚萜苷C(picrogentioside C)(6)、藏黄连獐芽菜苷Ⅰ(picrosecosideⅠ)(7)、藏黄连獐芽菜苷Ⅱ(picrosecosideⅡ)(8)、藏黄连獐芽菜苷A(picrosecoside A)(9)、藏黄连獐芽菜苷B(picrosecoside B)(10)。
除分出上述10个新化合物外,在剩余25个化合物中,有4个化合物为首次在胡黄连属内分离得到,分别为獐芽菜苷(sweroside)(27)、龙胆苦苷(gentiopicroside)(28)、香草醛(vanillin)(32)、辛二酸(suberic acid)(35)。
本文系统研究了上述化合物的物理化学性质,剖析了新化合物与已知化合物化学组成与结构。研究结果为研究西藏胡黄连的化学成分、药理作用以及后继开发研究该中药材提供了理论依据。
The plant Picrorhiza scrophulariiflora Pennell (Scrophulariaceae) grows in high-altitude regions (above 4400 m) in southeast Tibet and northwest Yunnan province of China. The root of this plant is used in traditional Chinese medicine for the treatment of damp-heat dysentery, jaundice, indigestion, common fever, acute viral hepatitis, and steaming of bone.
For the purpose of clearing the material base of its bioactivity and providing theory basis for the successor development research on the root of Picrorhiza scrophulariiflora Pennell, the chemical constituents investigation on the acetic ether layer and n-butanol layer of the 95% ethanol extracts was carried out. By using silica gel , sephadex LH-20, HPLC and so on, 42 compounds were isolated, morever, the structures of 35 compounds were identified by the physical-chemical properties and spectral methods, which were identified as scroside H(1)、scrosideⅠ(2)、picrogentiosideⅠ(3)、picrogentiosideⅡ(4)、picrogentioside A(5)、picrogentioside C(6)、picrosecosideⅠ(7)、picrosecosideⅡ(8)、picrosecoside A()9)、picrosecoside B(10)、scrocaffeside A(11)、scrocaffeside B(12)、scrocaffeside C)(13)、scroside D(14)、scroside E(15)、scroside G(16)、scrophenoside A(17)、25-acetoxy-2-β-D-glucopyranosyloxy-3 , 16 , 20-trihydroxy-9-methyl-19- norlanosta-5,23-diene-22-one(18)、vanillic acid(19)、gallic acid(20)、arbutin(21)、androsin(22)、catechin(23)、11-O-galloylbergenin(24)、6-feruloylcatalpol(25)、veronicoside(26)、sweroside(27)、gentiopicroside(28)、isoferulic acid(29)、plantamajoside (30)、plantainoside D(31)、vanillin(32)、β-sitosterol(33)、daucosterol(34)and suberic acid(35)。
Among them compound 27、28、32、35 were isolated from Picrorhiza genus for the first time, compounds1-10 were new compounds.
本文对西藏胡黄连的化学成分进行了研究。西藏胡黄连用95%乙醇回流提取,提取所得浸膏利用硅胶色谱、凝胶色谱和HPLC色谱等分离方法进行分离提纯,从中分离得到了42个化合物。通过理化性质、化学反应以及波谱分析,鉴定了其中35个化合物的结构。
在已分离并鉴定出结构的35个化合物中,首次分离得到10个新化合物,分别为苯乙醇苷类和环烯醚萜苷类化合物:藏黄连苷H (scroside H)(1)、藏黄连苷Ⅰ(scrosideⅠ)(2)、藏黄连环烯醚萜苷Ⅰ(picrogentiosideⅠ)(3)、藏黄连环烯醚萜苷Ⅱ(picrogentiosideⅡ)(4)、藏黄连环烯醚萜苷A(picrogentioside A)(5)、藏黄连环烯醚萜苷C(picrogentioside C)(6)、藏黄连獐芽菜苷Ⅰ(picrosecosideⅠ)(7)、藏黄连獐芽菜苷Ⅱ(picrosecosideⅡ)(8)、藏黄连獐芽菜苷A(picrosecoside A)(9)、藏黄连獐芽菜苷B(picrosecoside B)(10)。
除分出上述10个新化合物外,在剩余25个化合物中,有4个化合物为首次在胡黄连属内分离得到,分别为獐芽菜苷(sweroside)(27)、龙胆苦苷(gentiopicroside)(28)、香草醛(vanillin)(32)、辛二酸(suberic acid)(35)。
本文系统研究了上述化合物的物理化学性质,剖析了新化合物与已知化合物化学组成与结构。研究结果为研究西藏胡黄连的化学成分、药理作用以及后继开发研究该中药材提供了理论依据。
The plant Picrorhiza scrophulariiflora Pennell (Scrophulariaceae) grows in high-altitude regions (above 4400 m) in southeast Tibet and northwest Yunnan province of China. The root of this plant is used in traditional Chinese medicine for the treatment of damp-heat dysentery, jaundice, indigestion, common fever, acute viral hepatitis, and steaming of bone.
For the purpose of clearing the material base of its bioactivity and providing theory basis for the successor development research on the root of Picrorhiza scrophulariiflora Pennell, the chemical constituents investigation on the acetic ether layer and n-butanol layer of the 95% ethanol extracts was carried out. By using silica gel , sephadex LH-20, HPLC and so on, 42 compounds were isolated, morever, the structures of 35 compounds were identified by the physical-chemical properties and spectral methods, which were identified as scroside H(1)、scrosideⅠ(2)、picrogentiosideⅠ(3)、picrogentiosideⅡ(4)、picrogentioside A(5)、picrogentioside C(6)、picrosecosideⅠ(7)、picrosecosideⅡ(8)、picrosecoside A()9)、picrosecoside B(10)、scrocaffeside A(11)、scrocaffeside B(12)、scrocaffeside C)(13)、scroside D(14)、scroside E(15)、scroside G(16)、scrophenoside A(17)、25-acetoxy-2-β-D-glucopyranosyloxy-3 , 16 , 20-trihydroxy-9-methyl-19- norlanosta-5,23-diene-22-one(18)、vanillic acid(19)、gallic acid(20)、arbutin(21)、androsin(22)、catechin(23)、11-O-galloylbergenin(24)、6-feruloylcatalpol(25)、veronicoside(26)、sweroside(27)、gentiopicroside(28)、isoferulic acid(29)、plantamajoside (30)、plantainoside D(31)、vanillin(32)、β-sitosterol(33)、daucosterol(34)and suberic acid(35)。
Among them compound 27、28、32、35 were isolated from Picrorhiza genus for the first time, compounds1-10 were new compounds.
引文
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2王答祺,贺震旦,冯宝树等,西藏胡黄连的化学成分[J].云南植物研究, 1993, 15(1):83-88。
3张惠兰,夏光成,楼之岑等.国产胡黄连的植物及生药学研究[J].药学学报,1965,12(12):808.
4 Narayanan P,Akamanchi K G.Colorimetric estimation of total iridoid content of Picrorhiza kurrooa [J].J Asian Nat Prod Res,2003,5(2):105-111.
5 Stuppner H,Wagner H.Minor iridoid and phenolglycosides of Picrorhiza kurrooa [J].Planta Med,1989,55:467.
6 Weinges K,Schick H,Neuber K et al.Isolierung und strukturaufklarung nruer inhaltssttoffle aus dem sodoalkalischen extraction Picrorhiza kurrooa [J].Liebigs Ann Chem,1989:1113.
7汪豪,吴佳俊,刘戈等.西藏胡黄连中的环烯醚萜类化学成分[J].中国天然药物,2006,4(1):36-39.
8 Li Jian Xin,Li Ping,Tezuka Yasuhiro et al.Three phenylethanoid glycosides and an iridoid glycoside from Picrorhiza scrophulariiflora [J].Phytochemistry,1998,48:537.
9 Hao Wang,Wen-Cai Ye,Ren-Wang Jiang et al.Three new cyclopentanoid monoterpenes from Picrorhiza scrophulariiflora [J].Planta Med Letter,2004,70:382-384.
10 Stupper H,Wagner H.New cucurbitacin glycosides from Picrorhiza kurrooa [J].Planta Med,1989,55:559-563.
11 Stupper H,Muller E P,Wagner H.Cucurbitacin from Picrorhiza kurrooa [J].Phytochemistry,1991,30(1):305.
12 Stupper H,Kahling H P,Seligmann O et al.Minor cucurbitacin glycosides from Picrorhiza kurrooa [J].Phytochemistry,1990,29(5):1633.
13 Stupper H,Muller E P.Cucurbitacin with unusual side chains from Picrorhiza kurrooa [J].Phytochemistry,1993,33(5):1139.
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