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  • 學位論文

台灣產鷗蔓之娃兒藤生物鹼的分離與鑑定

Isolation and Identification of Phenanthroindolizidine Alkaloids from Formosa Tylophora ovata

指導教授 : 李秀珠 張晃猷
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摘要


鷗蔓又稱卵葉娃兒藤,在分類學上屬於被子植物門、雙子葉綱、龍膽目、蘿摩科、娃兒藤屬(鷗蔓屬),為多年生藤蔓性植物。目前全世界已有60種以上的娃兒藤屬植物被鑑定出來,而這些娃兒藤屬植物大多含有娃兒藤生物鹼,又稱菲并吲哚啶生物鹼(phenanthroindolizidine alkaloids),此種化學成分首次於1935年從印度娃兒藤中分離出來,並命名為娃兒藤鹼(tylophorine),這些化合物多數具有抗癌、抗發炎等生物活性。本篇研究以台灣生鷗蔓做為研究材料,除了希望藉此開啟台灣娃兒藤植物所含活性成分的研究之外,也希望藉此尋找抗癌等生物活性更佳的娃兒藤生物鹼。首先經由甲醇萃取、酸鹼萃取、分配萃取,生物鹼成分會溶解在有機層,再經一系列管柱層析、製備級高效率液相層析(preparative high pressure liquid chromatography)實驗,以純化莖、葉所含的生物鹼成分。最後從葉部分離出10種化合物;從莖部則分離出7種,經由EI-MS、1H-NMR、13C-NMR、DEPT、2D-NMR,並輔以UV、IR、比旋光度等分析方法來確認化合物結構,共有12種不同的娃兒藤生物鹼被分離出來,分別是:(S)-(+)-tylophorine, (S)-(+)-septicine, (+)-tylophorinine, (-)-tylophorinicine, (+)-tylophorinicine , (S)-(+)-hispidine, (S)-(+)-2,6-didesmethoxyl-4-hydroxyl-septicine, (S)-(+)-6-desmethylsepticine, (S)-(+)-6-desmethyltylophorine, (S)-(+)-3-desmethyisotylocrebrine, trans-(+)-3,14α-dihydroxy-4,6,7-trimethoxyphenanthroindolizidine, and trans-(+)-3,14α-dihydroxy-6,7-dimethoxyphenanthroindolizidine. 關鍵詞:娃兒藤生物鹼(菲并吲哚啶生物鹼)、製備級高效率液相層析、印度娃兒藤、鷗蔓(卵葉娃兒藤)、娃兒藤鹼。

並列摘要


Tylophora ovata (T. ovata) belongs to phylum Magnoliophyta, class Dicotyledoneae, order Gentianales, family Asclepiadaceae, and genus Tylophora. Up to date, botanists have found about 60 species of Tylophora all over the world. Since the first isolation of tylophorine from Tylophora indica in A.D. 1935, many kinds of phenanthroindolizidine or phenanthroquinolizidine alkaloids have been isolated and purified from Asclepiadaceae, especially from Tylophora and Cynanchum. These alkaloids have been shown to exert anti-leukemia, anti-asthma, anti-anaphylactic, anti-bacterial and other anti-inflammatory activities. Last decade, they have regained attentions for development into therapeutic agents with well known cytotoxic activity against a variety of cancer cell lines in vitro and in vivo. T. ovata is most commonly distributed species of tylophora plants native to Taiwan than the other two species, T. oshimae Hayata and T. taiwanensis Hatusima). In order to investigate the tylophorine analogous ingredients from T. ovata, we collected T. ovata plant materials for isolation and purification of tylophorine analogues. The air-dried leaves and stems were extracted with MeOH at boiling point under reflux and then concentrated to green-brown gummy residues, respectively. The residues in 0.5% HCl-soluble portions were filtered. The filtrates were made alkaline with 25% NH4OH (pH=9), and extracted repeatedly with CHCl3 until the organic layer exhibited Dragendorff test was negative. Subsequently, a series of chromatography including open silica gel column and preparative high pressure liquid chromatography were applied for purification. EI-MS, 1H-NMR, 13C-NMR, DEPT, 2D-NMR, IR, and [α] were exploited to identify the structures of the 12 compounds from the leaves and the stems of T. ovata. They are (S)-(+)-tylophorine, (S)-(+)-septicine, (+)-tylophorinine, (+)-tylophorincine, (-)-tylophorincine, (S)-(+)-hispidine, (S)-(+)-2,6-didesmethoxyl-4-hydroxyl-septicine, (S)-(+)-6-desmethylsepticine, (S)-(+)-6-desmethyltylophorine, (S)-(+)-3-desmethyisotylocrebrine, trans-(+)-3,14α-dihydroxy-4,6,7-trimethoxyphenanthroindolizidine, and trans-(+)-3,14α-dihydroxy-6,7-dimethoxyphenanthroindolizidine.

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