- 學位論文
印度紫檀與台灣油點草之化學成分及生物活性之研究
Studies on the Chemical Constituents and Bioactivities of Pterocarpus indicus and Tricyrtis formosana
摘要
印度紫檀 (豆科) 分佈於熱帶地區，在南亞是相當著名的植物，當地民間流傳其紅色的乳膠汁可抑制腫瘤的生長；印度紫檀皮部之甲醇粗萃物在 50 ?慊/ml 對子宮頸癌細胞株 (Hela cells) 顯現 52.0% 的抑制活性能力；經初步分層後，其水層萃取物與氯仿層萃取物在 20 ?慊/ml 濃度時分別顯現 58.6% 與 53.6% 之抑制活性能力；在化學成分研究方面，從氯仿層和水層萃取物共分離出十個化合物。其中包含六個三帖類化合物：包含 lupeol (1)，betulinic acid (2)，betulin (3)，betulin-3-caffeate (4)，friedelin (5)及3??-friedelinol (6)；一個醣類：為 sucrose (7)；三個固醇類混合物，分別為 ??-sitosterol (8) 及 stigmasterol (9)，??-sitosteryl-3-O-??-D-glucoside (10) 及 ??-sigmasteryl-3- O-?n??- D-glucoside (11)，??-sitosterone (12) 及stigmasterone (13)；在這些化合物當中，化合物 4 在DPPH radical scavenging activity的抗氧化活性試驗裡，其 IC50?n值為16.75 ?慊/ml。 台灣油點草 (百合科) 為多年生草本，是台灣特有的植物，屬油點草屬；台灣油點草的甲醇粗萃物，經初步分層後的正己烷層和丙酮層萃取物具有抑制癌細胞生長及抗發炎的活性，在化學成分研究方面，本研究從台灣油點草的正己烷層和丙酮層萃取物中分離純化得到 七個化合物，其中有三個固醇類混合物，為 ??-sitosterol (8) 及 stigmasterol (9)，??-sitosteryl-3-O-??-D-glucoside (10) 及 ??-sigmasteryl-3- O-?n??- D-glucoside (11)，6-(??-sitosteryl-3-O-??-glucopyranosidyl)- stearate (14) 及6-(??-sitosteryl-3-O-??-glucopyranosidyl)- icosanoate (15)；兩個神經醯胺類混合物，其一為2-hydroxy-N-(1,3,4-trihydroxypentadecan-2-yl) pentacosanamide (16)，2-hydroxy-N-(1,3,4-trihydroxyheptadecan-2-yl) pentacosanamide (17) 及2-hydroxy-N-(1,3,4-trihydroxynondecan-2-yl) pentacosanamide (18)；另一為 2-hydroxy-N-(1,3,4- trihydroxyhexatriaco ntan-2-yl) pentacosanamide (19)，2-hydroxy-N-(1,3,4-trihydroxyoctatriac ontan-2-yl) pentacosanamide (20) 及2-hydroxy-N-(1,3,4-trihydroxytetracon tan-2-yl) pentacosanamide (21)；兩個脂肪類化合物，其一為 stearic acid (22)，另一為heptadecanoic acid (23)，nondecanoic acid (24)，heneicosanoic acid (25) 及tricosanoic acid (26) 之混合物。這些化合物都是第一次從此植物被分離出來，其中混合物 19，20，21 為新的ceramides。
並列摘要
Pterocarpus indicus (Fabaceae) distributed throughout the tropics. It is one of the best-known trees in the southern Asia. The red latex is used as folk medicine for the treatment of tumors. The methanolic extracts of the barks of P. indicus exhibited 52.0% inhibition against the Hela cancer cell line at 50 ?慊/ml. After partition, the water layer and chloroform layer exhibited 58.6% and 53.6% inhibition against the Hela cancer cell line at 20 ?慊/ml respectively. There were ten compounds isolated from the chloroform and the water layers, including six triterpenoids: lupeol (1), betulinic acid (2), betulin (3), betulin-3-caffeate (4), friedelin (5), and 3??-friedelinol (6); one sugar: sucrose (7); three mixtures of steroids: ??-sitosterol (8) and stigmasterol (9), ??-sitosteryl-3-O-??-D-glucoside (10) and ??-sigmasteryl-3- O-?n??- D-glucoside (11), and ??-sitosterone (12) and stigmasterone (13). In addition, compound 4 showed moderate anti-oxidant activity, the value of IC50?n is 16.75 ?慊/ml. Tricyrtis formosana( Liliaceae) is an indigenous, herbaceous perennial plant in Taiwan. The n-hexane and acetone layers from the methanolic extracts of T. formosana showed cytotoxicity and anti-inflammentary effects. In this study, seven compounds were isolated, including three mixtures of steroids: ??-sitosterol (8) and stigmasterol (9), ??-sitosteryl-3-O-??-D-glucoside (10) and ??-sigmasteryl-3-O-??- D-glucoside (11), 6-(??-sitosteryl-3-O-??-glucopyranosidyl)-stearate (14) and 6-(??-sitosteryl-3-O-??-glucopyranosidyl)- icosanoate (15); two mixtures of ceramides: 2-hydroxy-N-(1,3,4-trihydroxypentadecan-2-yl) pentacosanamide (16), 2-hydroxy-N-(1,3,4-trihydroxyheptadecan-2-yl) pentacosanamide (17), and 2-hydroxy-N-(1,3,4-trihydroxynondecan-2-yl) pentacosanamide (18), and 2-hydroxy-N-(1,3,4-trihydroxyhexatriacontan-2-yl) pentacosanamide (19), 2-hydroxy-N-(1,3,4-trihydroxyoctatriacontan-2-yl) pentacosanamide (20), and 2-hydroxy-N-(1,3,4-trihydroxytetracontan-2-yl) pentacosanamide (21); two fatty acids: stearic acid (22), a mixture of heptadecanoic acid (23), nondecanoic acid (24), heneicosanoic acid (25), and tricosanoic acid (26). These compounds were isolated for the first time from this plant. Among them, the mixture of 19, 20, and 21 are new ceramides.