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標題: | 長尾尖葉櫧抑制甲型葡萄糖水解酶之活性成分暨其化學修飾之研究 Active constituents from Castanopsis cuspidata var. carlesii against α-glucosidase and chemical modification of castanopsinins |
作者: | Chen-Che Wu 吳承哲 |
指導教授: | 李水盛 |
關鍵字: | 糖尿病,口服抗高血糖藥,甲型葡萄糖水解酶,長尾尖葉櫧,三?類, Diabetes mellitus,oral antidiabetic agents,α-glucosidase,Castanopsis cuspidata var. carlesii,triterpenoids, |
出版年 : | 2013 |
學位: | 碩士 |
摘要: | 糖尿病(Diabetes Mellitus)是世界各地盛行的一種慢性病,分為第一型、第二型及其他類型。治療第二型糖尿病的口服抗高血糖藥物中,甲型葡萄糖水解酶抑制劑(α-glucosidase inhibitors)其作用機制為抑制小腸壁的刷狀絨毛上的甲型葡萄糖水解酶(α-glucosidase),藉由延遲多糖被水解成葡萄糖及其他單糖,可以達到減緩飯後血糖的上升,來達到治療糖尿病的效果。
長尾尖葉櫧(Castanopsis cuspidata var. carlesii)為殼斗科栲屬植物,本論文對先前本植物葉部之成分研究進行更徹底之探研。針對乙醇萃取物之正丁醇可溶部分做進一步成分分離,利用Sephadex LH-20管柱層析、離心式分配層析儀、逆相高效液相層析儀分離純化,共得8個化合物及3組混合物。化合物包含1個黃酮類(4)及7個沒食子酸衍生物(1-3, 5-8),3組混合物為castanopsinins系列之三萜類化合物(9a/b, 10a/b, 13a/b),每組混合物含有兩個化合物,並探討各成分對甲型葡萄糖水解酶(α-glucosidase)之活性抑制。結果發現castanopsinins系列化合物皆有較好之抑制活性。 Castanopsinins系列化合物(castanopsinins A-H)之三萜骨架為ursane及oleanane型,並以難分離之混合物呈現。因此,本實驗更進一步利用化學修飾以及各種分離方法,已發展出一種可以純化ursane type 及oleanane type之三萜類化合物之方法。探討官能基對活性之影響,結果發現castanopsinins類化合物的3,3',4,4',5,5'-hexahydroxydiphenoyl (HHDP) 基對甲型葡萄糖水解酶抑制活性相當重要。 Diabetes mellitus (DM) is a chronic disease growing with high prevalence worldwide. There are two main types of DM, type I and type II. Among the oral antidiabetic agents, α-glucosidase inhibitors target on the enzymes in the small intestine brush border, which are responsible for the breakdown of oligosaccharides and disaccharides into glucose and other monosaccharides. They can delay the digestion of carbohydrates, lowering postprandial glucose level to achieve therapeutic control of DM. In a continuation of our recent study on the EtOH extract of Castanopsis cuspidata var. carlesii leaf, this thesis focused on chemical investigation of the n-BuOH soluble fraction. Repeated chromatography on Sephadex LH-20, centrifugal partition chromatograph, and reversed-phase C-18 columns yielded one flavonoid (4), seven gallic derivatives (1-3, 5-8) and three castanopsinins, each composed of two compounds (9a/b, 10a/b, 13a/b). Among them, castanopsinins showed better inhibitory activities against α-glucosidase. Castanopsinins A-H contain a triterpenoid core. Separation of structural isomers consisting of a mixture of oleanane and ursane type triterpene skeletons is very difficult. The present study tried to establish a simple way to separate them using chemical modifications and various separation methods, leading to the preparation of these two types of triterpenoids. Bioassay of the isolated and prepared triterpenoid derivatives has been undertaken and found the 3,3',4,4',5,5'-hexahydroxydiphenoyl (HHDP) moiety to play an important role in their anti-α-glucosidase activity. |
URI: | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/62257 |
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顯示於系所單位: | 藥學系 |
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