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研究生:吳家侖
研究生(外文):Chia-Lun Wu
論文名稱:山苦瓜藤葉中的化學成分與生物活性之探討
論文名稱(外文):Studies on Chemical Constituents and Biological Activities From the Vines and Leaves of Momordica charantia L. var abbreviata Ser.
指導教授:黃中宜郭曜豪郭曜豪引用關係
指導教授(外文):Chung-Yi HuangYao-Haur Kuo
口試委員:駱錫能陳翠瑤李宗徽
口試委員(外文):Shyi-Neng LouTsui-Yao ChenTzong-Huei Lee
口試日期:2014-07-14
學位類別:碩士
校院名稱:國立宜蘭大學
系所名稱:食品科學系碩士班
學門:農業科學學門
學類:食品科學類
論文種類:學術論文
論文出版年:2014
畢業學年度:102
語文別:中文
論文頁數:152
中文關鍵詞:苦瓜藤葉三萜類化合物細胞毒殺抗發炎α-葡萄糖苷酶
外文關鍵詞:Momordica charantia L.vines and leavestriterpenoidscytotoxicityanti-inflammatoryα-glucosidase
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山苦瓜 (Momordica charantia L. var abbreviata Ser.) 為葫蘆科苦瓜屬的一年生蔓性草本植物,其含有三萜類、皂苷、類黃酮與酚酸等生物活性物質。其中三萜類化合物具有抗腫瘤、抗糖尿病、抗發炎及其他藥理活性等。本實驗室先前的研究曾由山苦瓜果實中分離出具有降血糖與抗腫瘤之葫蘆烷型三萜類化合物與其皂苷。本論文進一步研究山苦瓜藤葉,期望能從中分離出具有生物活性的三萜類化合物與皂苷。本研究將山苦瓜藤葉以 95% 乙醇提取,經一系列層析方法進行分離與純化,總共分離得到二十個葫蘆烷型三萜類化合物,其中包含七個新化合物,分別為 Kuguacins T-V (A1, A2, C2)、Kuguaglycosides I-L (B1, B2, B3, C1),以及十三個已知化合物 (19R,23E)-5β,19-Epoxy-19-methoxycucurbita-6,23,25-triene-3β-ol (A3)、(23E)-5β,19-Epoxycucurbita-6,23-diene-3β,25-diol (A4)、Kuguaglycoside C (A5)、(19R,23E)-5β,19-Epoxy-19-methoxycucurbita-6,23-diene-3β,25-diol (A6)、(19S,23E)-5β,19-Epoxy-19-methoxycucurbita-6,23-diene-3β,25-diol (A7)、(19R,23E)-5β,19-Epoxy-19,25-dimethoxycucurbita-6,23-diene-3β-ol (A8)、(19S,23E)-5β,19-Epoxy-19,25-dimethoxycucurbita-6,23-diene-3β-ol (A9)、(23R)-23-O-Methyl-momordicine IV. (B4)、Kuguasaponin I (B5)、(23E)-3β-Hydroxy-7β,25-dimethoxycucurbita-5,23-diene-19-al (C3)、Momordicoside K (C4)、Momordicoside L (C5)、Kuguasaponin B (C6)。以上化合物皆利用一維及二維核磁共振光譜技術 (COSY、HSQC、HMBC 與 NOESY) 與高解析質譜儀進行結構解析,化合物 A1、C3、C4 與 C6 完整化學結構進而由 X-Ray 資料確認。生物活性方面,細胞毒殺試驗中顯示,化合物 B4、B5、C1、C6 對 A549、HepG2、MCF-7 與 WiDr 具有細胞毒殺活性 (IC50值介於 5~20 μM);抗發炎試驗中顯示,化合物 B4、B5、C1、C4、C6 具有抗發炎活性 (IC50值介於 9~18 μM);於 α-葡萄糖苷酶活性抑制試驗則無明顯效果存在。

Momordica charantia L. var abbreviata Ser. is a climber, belonging to family Cucurbitaceae, and its biological components contain triterpenoids, saponins, flavonoids, phenolic acids. In addition, cucurbitane-type triterpenoids exhibited various biological activities including anti-cancer, anti-diabetic, anti-inflammatory and other pharmacological activities. Our previous study on the fruit of M. charantia resulted in the isolation of cucurbitane-type triterpenoids and saponins, which showed anti-diabetic and anti-cancer effects. To discover more biosctive cucurbitanes and its glycosides from the vines and leaves of the title plants. we extracted the vines and leaves of M. charantia with 95% ethanol. Further purification by using a series of chromatographic methods, seven new compounds, Kuguacin T-V (A1, A2, C2), Kuguaglycoside I-L (B1, B2, B3, C1), along with thirteen known cucurbitanes and its saponins, (19R,23E)-5β,19-Epoxy-19-methoxycucurbita-6,23,25-triene-3β-ol (A3), (23E)-5β,19-Epoxycucurbita-6,23-diene-3β,25-diol (A4), Kuguaglycoside C (A5), (19R,23E)-5β,19-Epoxy-19-methoxycucurbita-6,23-diene-3β,25-diol (A6), (19S,23E)-5β,19-Epoxy-19-methoxycucurbita-6,23-diene-3β,25-diol (A7), (19R,23E)-5β,19-Epoxy-19,25-dimethoxycucurbita-6,23-diene-3β-ol (A8), (19S,23E)-5β,19-Epoxy-19,25-dimethoxycucurbita-6,23-diene-3β-ol (A9), (23R)-23-O-Methylmomordicine IV. (B4), Kuguasaponin I (B5), (23E)-3β-Hydroxy-7β,25-dimethoxycucurbita-5,23-diene-19-al (C3), Momordicoside K (C4), Momordicoside L (C5), and Kuguasaponin B (C6), were isolated from the EtOH extract of M. charantia. Structural elucidation of the new isolates were based on spectroscopic analyses, including 1D and 2D NMR techniques (COSY, HSQC, HMBC and NOESY) and mass spectrometry. The structure of compound A1, C3, C4, and C6 was further confirmed by single X-ray crystallographic analysis. Cytotoxicity assays showed that compounds B4, B5, C1, and C6 possessed moderate cytotoxicity against several human tumor cell lines (MCF-7, A549, WiDr, and HepG2, IC50 = 5~20 μM). In the anti-NO production test, compounds B4, B5, C1, C4, and C6 showed moderate inhibitory effects (IC50 = 9~18 μM). However, all the isolates have no α-glucosidase inhibitory effects.

中文摘要 I
英文摘要 II
總目錄 V
表目錄 VI
圖目錄 VII
縮寫表 X
第一章 緒論 1
第一節 研究背景與目的 1
第二節 山苦瓜與苦瓜之介紹 4
第三節 藥理與化學成分研究回顧 7
第二章 材料與方法 43
第一節 實驗儀器與藥品 43
第二節 實驗架構 47
第三節 實驗方法 48
第三章 化合物之結構解析 57
三萜類化合物及其皂苷之簡介 57
第一節 Kuguacin T (A1) 之結構解析 59
第二節 Kuguacin U (A2) 之結構解析 69
第三節 Kuguaglycoside I (B1) 之結構解析 78
第四節 Kuguaglycoside J (B2) 之結構解析 88
第五節 Kuguaglycoside K (B3) 之結構解析 98
第六節 Kuguaglycoside L (C1) 之結構解析 108
第七節 Kuguacin V (C2) 之結構解析 118
第八節 已知化合物 (C3) 立體結構之 X-Ray 確認 127
第九節 已知化合物 (C4) 立體結構之 X-Ray 確認 129
第十節 已知化合物 (C6) 立體結構之 X-Ray 確認 131
第四章 生物活性試驗 133
第一節 細胞毒殺活性 133
第二節 抗發炎活性 138
第三節 α-葡萄糖苷酶活性抑制 141
第五章 結論 142
第六章 參考文獻 144

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