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  • 學位論文

苦瓜果實中苦瓜苷成分及其生物活性之探討

Studies on Kuguaosides and their Bioactivities from the Momordica charantia Fruit

指導教授 : 徐鳳麟
共同指導教授 : 郭曜豪
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摘要


苦瓜 (Momordica charantia L.) 為一年生蔓性攀緣草本植物,為葫蘆科( Cucurbitaceae ),苦瓜屬 ( Momordica ) 的植物。苦瓜常被作為食用與藥用的植物,之前研究已證實苦瓜具有降血糖、抗腫瘤、抗發炎等功效。本研究以苦瓜果實70 % 酒精的萃取物,針對皂素活性成分並配合生物活性導向篩選 ( Bioactive-guided fractionation ) 進行分離與純化,總共分離得到二十九個葫蘆烷型 ( Cucurbitane-type ) 三萜類的化合物,包括十五個新化合物,分別為kuguaoside A (A1)、kuguaoside B (A2)、kuguaoside C (A3)、kuguaoside D (A4)、kuguaoside E (A5) 和kuguaoside F (B1)、kuguaoside G (B2)、kuguaoside H (B3)、kuguaoside I (B4)、kuguaoside J (B5)、kuguaoside K (B6)、kuguaoside L (B7)、kuguaoside M (B8)、kuguaoside N (B9)、kuguaoside O (B10),以及十四個已知化合物,momordicoside I (A6)、momordicoside F1 (A7)、momordicoside F2 (A8)、momordicoside K (A9)、momordicoside L (A10)、momordicoside U (A11)、goyaglycoside-b (A12)、goyaglycoside-d (A13)、7β,25-dihydroxycucurbita-5,23(E)-dien-19-al 3-O-β-D- allopyranoside (A14) 、25-hydroxy-5β,19-epoxycucurbita- 6,23-dien-19-on-3β-ol 3-O-β-D-glucopyranoside (A15)、momordicine IV (B11)、goyaglycoside-a (B12)、kuguaglycoside C (B13)、3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al (B14)。以上化合物皆藉由一維、二維核磁共振光譜等物理數據及化學方法鑑定化合物之結構。 藥理活性方面,在細胞毒殺 ( Cytotxicity ) 試驗中顯示,化合物A1、A2、A6、A7、A8、A9、A11、A12、A13、B1、B3、B4、B5、B6、B8、B12、B13對於人類乳癌細胞 ( MCF-7, Human breast adenocarcinoma )、人類結腸癌細胞 ( WiDr, Human colon adenocarcinoma ) 、人類喉癌細胞 ( HEp-2, Human laryngeal carcinoma ) 以及人類髓母細胞瘤 ( Doay, Human medulloblastoma ) 具有抑制癌細胞增生作用 ( IC50值介於 5~40 μg/ml之間),在葡萄糖攝取量 ( glucose uptake ) 測定中顯示,化合物A9、A14、B4、B5、B6、B7、B11有刺激C2Cl2肌肉母細胞 ( myoblast cell ),進而促進葡萄糖吸收的作用。結果顯示,苦瓜中葫蘆烷型的三萜類成分,可用以發展治療糖尿病或癌症藥物的潛力。

並列摘要


Momordica charantia L. (Cucurbitaceae), an annual vine, is widely distributed in tropical areas and is cultivated as vegetable crop and folk medicine in Taiwan. Previous investigations have shown that crude extracts of M. charantia possess antidiabetic (hypoglycemic), anti-tumor, anti-inflammatory activities. By column chromatography and bioassay-directed fractionation, twenty-nine cucurbitane-type triterpenoids including fifteen new compounds, kuguaoside A (A1), kuguaoside B (A2), kuguaoside C (A3), kuguaoside D (A4), kuguaoside E (A5), kuguaoside F (B1), kuguaoside G (B2), kuguaoside H (B3), kuguaoside I (B4), kuguaoside J (B5), kuguaoside K (B6), kuguaoside L (B7), kuguaoside M (B8), kuguaoside N (B9) and kuguaoside O (B10), along with fourteen known triterpene glycosides, momordicoside I (A6), momordicoside F1 (A7), momordicoside F2 (A8), momordicoside K (A9), momordicoside L (A10), momordicoside U (A11), goyaglycoside-b (A12), goyaglycoside-d (A13), and 7Momordica charantia L. (Cucurbitaceae), an annual vine, is widely distributed in tropical areas and is cultivated as vegetable crop and folk medicine in Taiwan. Previous investigations have shown that crude extracts of M. charantia possess antidiabetic (hypoglycemic), anti-tumor, anti-inflammatory activities. By column chromatography and bioassay-directed fractionation, twenty-nine cucurbitane-type triterpenoids including fifteen new compounds, kuguaoside A (A1), kuguaoside B (A2), kuguaoside C (A3), kuguaoside D (A4), kuguaoside E (A5), kuguaoside F (B1), kuguaoside G (B2), kuguaoside H (B3), kuguaoside I (B4), kuguaoside J (B5), kuguaoside K (B6), kuguaoside L (B7), kuguaoside M (B8), kuguaoside N (B9) and kuguaoside O (B10), along with fourteen known triterpene glycosides, momordicoside I (A6), momordicoside F1 (A7), momordicoside F2 (A8), momordicoside K (A9), momordicoside L (A10), momordicoside U (A11), goyaglycoside-b (A12), goyaglycoside-d (A13), and 7??,25-dihydroxycucurbita-5,23 (E)-dien-19-al 3-O-??-D-allopyranoside (A14), 25-hydroxy-????,19-epoxycucurbita-6,23 -dien-19-on-????-ol 3-O-??-D-glucopyranoside (A15), momordicine IV (B11), goyaglycoside-a (B12), kuguaglycoside C (B13), 3??,????,25-trihydroxycucurbita-5,23 (E)-dien-19-al (B14) were isolated and characterized glycosides constituents from 70 % EtOH extracts of the fruits of M. charantia. The structural elucidation of these fifteen new and fourteen known compounds were based on spectroscopic analyses (mainly 1D and 2D NMR techniques), as well as chemical evidences. Biological assay of cytotxicity showed that the A1, A2, A6, A7, A8, A9, A11, A12, A13, B1, B3, B4, B5, B6, B8, B12,and B13 possess moderate to promising cytotoxicity against several human tumor cell lines (MCF-7, WiDr, HEp-2, Doay, IC50 = 5~40 μg/ml). And in the glucose uptake test, A9, A14, B4, B5, B6, B7,and B11 could enhance the glucose uptake in C2Cl2 myoblast cell. These findings indicate that cucurbitane triterpenoids, the characteristic constituents of M. charantia, may provide leads as a class of therapeutic drugs against diabetes or cancer. ,25-dihydroxycucurbita-5,23 (E)-dien-19-al 3-O-β-D-allopyranoside (A14), 25-hydroxy-????,19-epoxycucurbita-6,23 -dien-19-on-3β-ol 3-O-β-D-glucopyranoside (A15), momordicine IV (B11), goyaglycoside-a (B12), kuguaglycoside C (B13), 3β,7β,25-trihydroxycucurbita-5,23 (E)-dien-19-al (B14) were isolated and characterized glycosides constituents from 70 % EtOH extracts of the fruits of M. charantia. The structural elucidation of these fifteen new and fourteen known compounds were based on spectroscopic analyses (mainly 1D and 2D NMR techniques), as well as chemical evidences. Biological assay of cytotxicity showed that the A1, A2, A6, A7, A8, A9, A11, A12, A13, B1, B3, B4, B5, B6, B8, B12,and B13 possess moderate to promising cytotoxicity against several human tumor cell lines (MCF-7, WiDr, HEp-2, Doay, IC50 = 5~40 μg/ml). And in the glucose uptake test, A9, A14, B4, B5, B6, B7,and B11 could enhance the glucose uptake in C2Cl2 myoblast cell. These findings indicate that cucurbitane triterpenoids, the characteristic constituents of M. charantia, may provide leads as a class of therapeutic drugs against diabetes or cancer.

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