甘肃醉鱼草化学成分及抑菌活性研究
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摘要
甘肃醉鱼草(Buddleja Purdomii W.W Smith.)为马钱科醉鱼草属植物,产于甘肃的岷县、武都、文县、舟曲等地,为甘肃特有种,无药用记载。本文通过对其化学成分的研究和体外抑菌活性的研究来探讨其是否有药用价值。
近年来有关醉鱼草属植物化学成分及生物活性的研究十分活跃,文献报道从醉鱼草属植物中分离得到的化学成分主要由黄酮、苯丙素酚苷、环烯醚萜苷、倍半萜和皂苷等化合物。有关甘肃醉鱼草的化学成分研究已有报道,但主要是石油醚及乙酸乙酯萃取部分。本文对甘肃醉鱼草的95%乙醇提取物的化学成分进行了更为深入的研究,采用结晶、重结晶方法和硅胶柱层析、聚酰胺柱层析等色谱技术纯化分离了10个化合物,并通过MS、~1H NMR、~(13)C NMR等现代波谱技术鉴定了10个化合物的结构:桃叶珊瑚苷(1)、丁香苷(2)、丁香树脂醇-单-O-β-D-葡萄糖苷(3)、毛蕊花糖苷(4),2-乙基-2-羟基-3-甲氧基丁酸葡萄糖苷(5)、6-(1,3-dihydroxypropan-2-yl)-3-(htydmxymethyl)cyclohex-2-enol(6)、6-(1,3-dihydroxypmpan-2-yl)-3-(hydroxymethyl),cyclohex-3-enol(7)、柳杉二醇(8)、半乳糖醇(9)、胡萝卜苷(10)。
本文采用GC-MS联用技术,对甘肃醉鱼草的石油醚萃取部分,经硅胶柱层析分离得到的低极性成分进行了分析,从分离出的317种组分中鉴定出66个化合物,占总峰面积的43.96%。并采用“K-B”法对低极性成分的体外抑菌活性做了初步研究。其体外抑菌活性研究表明:低极性成分对金黄色葡萄球菌有较强的抑制作用,对大肠埃希菌和铜绿假单胞菌都有一定的抑制作用。
通过对甘肃醉鱼草化学成分的研究,发现该植物中含有苯丙素酚苷类、木脂素类、萜类、芳香类、糖类及有机酸苷类化合物,其生物活性有待进一步研究。
Buddleja purdomii W.W Smith, is one of Buddleja L.,which distributeas in min.county,wudu county,zhouqu county of Gansu province.It is a kind of natural plant which cannot be found in the rest of China,except for Gansu.So far no relevant medicinal record has been reported.This dissertation is to study its chemical constituents and bacteriostatic activities in vitro to explore whether it has medicinal value.Many studies on the chemical constituents and bioactivities of genus Buddleja L. have been done. Previous phytochemical investigation on Buddleja led to flavonoids, phenylpropanoids,iridoids,sesquiterpenes and saponins.But only a few work on the chemical constituents and bioactivities has been reported on Buddleja purdomii W.W Smith..In order to provide rational knowledge for the bioactivity and plant taxonomy,the chemical constituents and bacteriostatic activities in vitro of Buddleja purdomii W.W Smith.have been investigated in this dissertation.The chemical constituents of the 95% ethanolic extract of Buddleja purdomii W.W Smith.were studied and 10 compounds were isolated by chromatography on silica gel column and polyamide column.Their structures were identified by spectroscopic methods such as MS,~1H NMR ,IR and ~(13)C NMR.Then 10 chemical constituents were established as aucubin (l),syringin(2),syringaresinol-O-β-D-glucopynanoside(3),acteoside(4)(2-ethyl -2-hydroxy- 3-methoxybutanoate-O-β-D-glucopynanoside)(5),6-(1,3-dihydroxypropan-2-yl)-3-(hydroxy-methyl)cyclohex-2-enol(6),6-(l,3-dihydroxypropan-2-yl)-3-(hydroxylmethyl)cyclohex-3-enol (7), cryptomeridiol(8), galactilol(9), and daucosterol(10).In this study,it has been found that Buddleja purdomii W.W Smith.is rich in phenylpropa-
noid glycosides,terpenes and galactilol.Their bioactivities are expected to be further studied.The constituents of the low polarity part from Buddleja purdomii W.W Smith.were analysed by GC-MS. 66 constituents were identified and they comprised 43.96% of the total peak area.We used the K.-B method to observe its antibacterial action in vitro.The results showed the low polarity constituents could effectively inhabit Staphy loco cciaureus, Escherichia coli and Psedomonas aeruginasa.
近年来有关醉鱼草属植物化学成分及生物活性的研究十分活跃,文献报道从醉鱼草属植物中分离得到的化学成分主要由黄酮、苯丙素酚苷、环烯醚萜苷、倍半萜和皂苷等化合物。有关甘肃醉鱼草的化学成分研究已有报道,但主要是石油醚及乙酸乙酯萃取部分。本文对甘肃醉鱼草的95%乙醇提取物的化学成分进行了更为深入的研究,采用结晶、重结晶方法和硅胶柱层析、聚酰胺柱层析等色谱技术纯化分离了10个化合物,并通过MS、~1H NMR、~(13)C NMR等现代波谱技术鉴定了10个化合物的结构:桃叶珊瑚苷(1)、丁香苷(2)、丁香树脂醇-单-O-β-D-葡萄糖苷(3)、毛蕊花糖苷(4),2-乙基-2-羟基-3-甲氧基丁酸葡萄糖苷(5)、6-(1,3-dihydroxypropan-2-yl)-3-(htydmxymethyl)cyclohex-2-enol(6)、6-(1,3-dihydroxypmpan-2-yl)-3-(hydroxymethyl),cyclohex-3-enol(7)、柳杉二醇(8)、半乳糖醇(9)、胡萝卜苷(10)。
本文采用GC-MS联用技术,对甘肃醉鱼草的石油醚萃取部分,经硅胶柱层析分离得到的低极性成分进行了分析,从分离出的317种组分中鉴定出66个化合物,占总峰面积的43.96%。并采用“K-B”法对低极性成分的体外抑菌活性做了初步研究。其体外抑菌活性研究表明:低极性成分对金黄色葡萄球菌有较强的抑制作用,对大肠埃希菌和铜绿假单胞菌都有一定的抑制作用。
通过对甘肃醉鱼草化学成分的研究,发现该植物中含有苯丙素酚苷类、木脂素类、萜类、芳香类、糖类及有机酸苷类化合物,其生物活性有待进一步研究。
Buddleja purdomii W.W Smith, is one of Buddleja L.,which distributeas in min.county,wudu county,zhouqu county of Gansu province.It is a kind of natural plant which cannot be found in the rest of China,except for Gansu.So far no relevant medicinal record has been reported.This dissertation is to study its chemical constituents and bacteriostatic activities in vitro to explore whether it has medicinal value.Many studies on the chemical constituents and bioactivities of genus Buddleja L. have been done. Previous phytochemical investigation on Buddleja led to flavonoids, phenylpropanoids,iridoids,sesquiterpenes and saponins.But only a few work on the chemical constituents and bioactivities has been reported on Buddleja purdomii W.W Smith..In order to provide rational knowledge for the bioactivity and plant taxonomy,the chemical constituents and bacteriostatic activities in vitro of Buddleja purdomii W.W Smith.have been investigated in this dissertation.The chemical constituents of the 95% ethanolic extract of Buddleja purdomii W.W Smith.were studied and 10 compounds were isolated by chromatography on silica gel column and polyamide column.Their structures were identified by spectroscopic methods such as MS,~1H NMR ,IR and ~(13)C NMR.Then 10 chemical constituents were established as aucubin (l),syringin(2),syringaresinol-O-β-D-glucopynanoside(3),acteoside(4)(2-ethyl -2-hydroxy- 3-methoxybutanoate-O-β-D-glucopynanoside)(5),6-(1,3-dihydroxypropan-2-yl)-3-(hydroxy-methyl)cyclohex-2-enol(6),6-(l,3-dihydroxypropan-2-yl)-3-(hydroxylmethyl)cyclohex-3-enol (7), cryptomeridiol(8), galactilol(9), and daucosterol(10).In this study,it has been found that Buddleja purdomii W.W Smith.is rich in phenylpropa-
noid glycosides,terpenes and galactilol.Their bioactivities are expected to be further studied.The constituents of the low polarity part from Buddleja purdomii W.W Smith.were analysed by GC-MS. 66 constituents were identified and they comprised 43.96% of the total peak area.We used the K.-B method to observe its antibacterial action in vitro.The results showed the low polarity constituents could effectively inhabit Staphy loco cciaureus, Escherichia coli and Psedomonas aeruginasa.
引文
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[2] 李冲,张承忠,姚华.互叶醉鱼草中的环烯醚萜甙.中草药,1994,25(5):227～228,271
[3] 王曙光,夏冰,董云法.紫花醉鱼草化学成分的研究.中草药,2003,34(5):403～405
[4] 李楠,庾石山.醉鱼草化学成分的研究.中草药,2003,34(8):693～695
[5] 余冬蕾,张青,张虎翼等.羊耳朵叶化学成分的研究.天然产物研究与开发,1997,9(4):14～18
[6] Houtghon,P.J.,Ethnopharmacology of some Buddleja species.J Ethnopharmacol. 1984, 11 (3): 293～308
[7] Yamamoto A, Nitta S, Miyase T, et al. Phenylethanoid and lignan-iridoid complex glycosides from roots of Buddleja davidii.Phytochemistry, 1993,32(2): 421～425
[8] Arciniegas A. Avendano A. Ana-L.Flavonoids from Buddleja parviflora. Biochemical Systematics and Ecology. 1997,25(2): 185～186
[9] Pardo F., Perich F., Villarroel L. et al.Isolation of verbascoside,an antimicrobial of Buddleja globisa leaves.J Ethnopharmacol. 1993,39(3):221～222
[10] Hu-YiZhang,Jing-Xian Pan.Phenylpropanoid glycosides and flavonoid glycosides isolated from buds of Buddleja officinalis Maxim.Journal of Chinese pharmaceutical sciences, 1996,5(2): 105～108
[11] Miyase, T.,Akahori C.Kohsaka H. et al. Acylated iridoid glycosides from Buddleja japonica Hemsl.Chem Pharm Bull, 1991,39(11):2944～2951
[12] Yoshida,T.,Nobuhara J.Uchida M. et al.Buddledin A,B and C,piscicidal sesquiterpwnes from Buddleja davidii Franch.Tetrahedron letters. 1976, 41:3717～3720
[13] Yoshida T, Nobuhara J,Okuda T.Studies on the constituents of Buddleja species. Ⅰ. Structures of buddledin A and B,two new toxic sesquiterpenes from Buddleja davidii Franch.Chem Phann Bull. 1978,26(8):2535～2542
[14] Alfonso Romo De vivar. David Aaron Nieto,Ruben Gavino. et al. Isocapanell-9- en-8-one and 6 a -hydroxyisocapanell-9-en-8-one, sesquiterpenes from Buddleja species. Phytochemistry.1995,40(1):167—170
[15] Mensah A.Y,et al.Known and novel terpenes from Buddleja globosa displaying selective antifungal activity against dermatophytes.J Nat prod.2000, 63:1210—1213
[16] Houghton,P.J.,Woldemariam T.Z. Candau M.et al.Buddlejajone,A diterpene from buddleja albiflora.Phytochemistry, 1996,42(2):485 —488
[17] Liao YH,Houghton PJ,Hoult JR.Novel and known constituents from Buddleja species and their activity against leukocyte eicosanoid generation. 1999,62(9): 1241 — 1245
[18] Yamamoto A,Miyase T,Ueno A,et al.Buddlejasaponin I-IV,four new oleananetriterpene saponions from the aerial parts of Buddleja japonica Hemsl Chem Pham Bull. 1991, 39(10): 2764-2766
[19] Ding N,Yahara S,Nohara T.Structure of mimengoside A and B,new triterpenoid glycosides from Buddlejae Flos produced in china.Chem Pharm Bull. 1992,40:780—782
[20] Emam AM,Diaz-Lanza AM, Matellano-Fernandez L, et al. Biological activities of buddlejasaponin isolated from Buddleja madaagascarensis and Scrophularia scorodonia.Pharmazie. 1997,52:76—77
[21] Jose Guillermo Avila A.Alfonso Romo de Vivar,Triterpenoid saponins and other glycoside from Buddleja scordioides.Biochemical systematics and ecology.2002, 30:1003—1005
[22] Houghton, P. J. Ligans and neolignans from Buddleja davidii, Phytochemistry, 1985, 24(4): 819-826
[23] Houghton, P.J., Phenolic fatty acid esters from Buddleja globosa stembark. Phochemistry, 1989,28(10):2693-2695
[24] Roder E.,Wiedenfeld H.Hoenig A.Isolierung eines neuen trizyklischen Piperdinalka loids aus Buddleja davidii.Planta Med.,1985,51(2):164—165
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