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指叶苔和多花花萼苔化学成分的研究
Chemical Constituents of Liverworts Lepidozia Reptans and Asterella Multiflora
【作者】 张艳丽;
【导师】 娄红祥;
【作者基本信息】 山东大学 , 天然药物化学, 2010, 硕士
【摘要】 苔藓植物门(Bryophyta)在分类学上介于藻类和蕨类植物之间,包括苔纲(Hepaticae),藓纲(Musci)和角苔纲(Anthocerotae),其中苔纲植物在全球约有6000余种。绝大多数苔类植物细胞中含有油体结构,可合成和储存萜类化合物及联苄类化合物。药理活性实验表明,许多双联苄类化合物具有抗真菌、抗微生物、细胞毒、抗癌、肌肉松弛以及对5-脂氧化酶、环氧化酶以及钙调节蛋白抑制作用等广泛的生物活性。本文对两种分别采自云南昆明轿子雪山和贵州苔类植物:指叶苔属指叶苔(Lepidozia reptans),花萼苔属多花花萼苔(Asterella multiflora)的生物活性成分进行了系统的研究,共分离鉴定获得26个化合物,包括联苄9个,三萜10个,倍半萜2个,甾体2个,单苯环化合物2个,长链脂肪族化合物1个。利用广泛的柱层析和半制备HPLC,从指叶苔中分离得到15个化合物:Friedelin 1, Taraxerone 2, Taraxerol 3, Betulinic Acid 4, Ursolic Acid 5, Abieslactone 6,24,25-dihydroabieslactone 7,5α-hydroxy-9α,10α-epoxycadinan-3-en-2β,14-olide 8; Perretten E9, Lunularin 10, Ethyl Orsellinate 11,3,4-dihydroxybenzoic acid 12, 10-nonacosanol 13,β-sitosterol 14, Daucosterine 15。化合物均采用NMR, MS,IR等波谱学方法及同已知化合物进行TLC对照或混合测定熔点鉴定。其中化合物8为新化合物,而其他化合物均为首次从该植物中分离得到。多花花萼苔富含联苄化合物,采用各种色谱分离方法从中分离得到11个化合物,并采用波谱学方法鉴定了其结构:Diplopterol 16,α-zeorin 17,6α,11α,22-trihydroxyhopane 18, Marchantin C 19, Isomarchantin C 20, Neomarchantin A 21,Riccardin D 22, Riccardin F 23, Isoriccardin C 24, Riccardin C 25, Herbertenediol26。化合物均采用NMR, MS, IR等波谱学方法及同已知化合物进行TLC对照或混合测定熔点鉴定。化合物均为首次从该植物中分离得到。
【Abstract】 The bryophytes, placed between algae and pteridophytes morphologically, are divided into Musci(mosses), Hepaticae(liverworts) and Anthocerotae(hornworts). More than 6 000 species of liverworts are known in the world. Almost all the liverworts possess cellular oil bodies which are mainly composed of terpenoids and bisbibenzyls. Recent studies reveal that bisbibenzyls exhibit various bioactivities, including antioxidant, cytotoxic, antibacterial, antiviral, anticancer and antifungal activities as well as inhibitory effects on cyclooxygenase,5-lipoxygenase and calmodulin.In this paper, the liverworts Lepidozia Reptans collected in Yunnan, Asterella multiflora collected in Guizhou were phytochemically investigated. A total of 26 compounds were obtained, including 9 bisbibenzyls,10 triterpenoids,2 sesquiter-penoids,2 steroids,1 higher fatty alcohols,2 simple aromatic compounds.From the extract of the liverwort Lepidozia Reptans,15 compounds including Friedelin 1, Taraxerone 2, Taraxerol 3, Betulinic Acid 4, Ursolic Acid 5, Abieslactone 6,24,25-dihydroabieslactone 7,5α-hydroxy-9α,10α-epoxycadinan-3-en-2β,14-olide 8, Perretten E 9, Lunularin 10, Ethyl Orsellinate 11,3,4-dihydroxybenzoic acid 12, 10-nonacosanol 13,β-sitosterol 14 and Daucosterine 15 were obtained. The structures were elucidated on the basis of 1D and 2D-NMR, MS and IR spectroscopy. Compound 8 is a new secondary metabolite. All the other compounds were isolated from this species for the first time. 11 compounds, including Diplopterol 16,α-zeorin 17,6α,11α,22-trihydroxy-hopane 18, Marchantin C 19, Iomarchantin C 20, Neomarchantin A 21, Riccardin D 22, Riccardin F 23, Isoriccardin C 24, Riccardin C 25 and Herbertenediol 26 were isolated from the liverwort Asterella multiflora. The structures were elucidated on the basis of 1D and 2D-NMR, MS and IR spectroscopy. All the compounds were isolated from this species for the first time.
【Key words】 bryophytes; Lepidozia Reptans; Asterella multiflora; chemical constituents; bisbibenzyls; terpenoids;