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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 李水盛 | |
dc.contributor.author | Chi-Chih Chang | en |
dc.contributor.author | 張吉智 | zh_TW |
dc.date.accessioned | 2021-06-15T16:45:28Z | - |
dc.date.available | 2018-09-24 | |
dc.date.copyright | 2015-09-24 | |
dc.date.issued | 2015 | |
dc.date.submitted | 2015-08-10 | |
dc.identifier.citation | 參考文獻
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dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/53118 | - |
dc.description.abstract | 第一部分 苦藤葉部抑制甲型葡萄糖水解酶活性成分之研究
苦藤Tinospora crispa (Linn.) Hook. f. et Thoms.為防己科青牛膽屬植物,帶有瘤狀莖的藤蔓,廣泛分布於亞洲熱帶與亞熱帶區域,包含印度、泰國、越南、菲律賓、印尼與馬來西亞等國家,其乾燥莖作為民俗療法應用於許多方面,並被證實具有抗糖尿病的活性。我們實驗室最近的研究發現,從莖部分離出來的活性成分,borapetosides A 與C具有降血糖之功效,其作用機轉與活化胰島素之訊息傳遞相關。延續這部分的工作至葉部,其成分還未被報導,同時本研究發現葉部的乙醇萃取物,具有抗甲型葡萄糖水解酶的活性,由於此標的抑制劑可用於治療第二型糖尿病,本研究擬揭示苦藤葉部這類活性成分。 苦藤葉部之乙醇萃取物具有抗甲型葡萄糖水解酶的活性,以生物活性為導向對此活性萃取物進行成分分離純化,藉助於HPLC-SPE-NMR連結技術,最後得到十七個黃酮類成分,包含了八個黃酮醯化苷(6-11, 13, 15),其中isoorientin-2'-(E)-sinapate (6)、isovitexin-2'-(E)-p-coumarate (8)、cosmosiin- 6'-(E)-ferulate (9)與cosmosiin-6'-(E)-cinnamate (15)為新化合物,它們的結構解析乃依據核磁共振及質譜光譜分析。酵素活性抑制試驗顯示,isovitexin- 2'-(E)-p-coumarate (8)具最強的抑制效果,其IC50值為4.3 ± 1.4 μM;然而isoorientin- 2'-(E)-p-coumarate (7),為3′位置羥基化,活性大幅降低(IC50: 35.7 μM)。其他cosmosiin之醯化衍生物,包含6'-(E)-ferulate (9)、6'-(E)-p-coumarate (10)、6'-(Z)-p-coumarate (11)與 6'-(E)-cinnamate (15),皆具有抑制活性,其IC50值分別8.8、14.6、10.1與 11.3 μM。 第二部分 柳葉石櫟葉部成分之研究 柳葉石櫟Pasania dodoniifolia Hayata為殼斗科柯屬植物,常綠中型喬木,高度可達9公尺,直徑約10公分,屬於台灣特有植物,分布於台灣南部中低海拔,在我們研究之前,還未有相關的成分報導,因此本研究擬研究其化學組成。 柳葉石櫟(Pasania dodoniifolia Hayata)葉部之乙醇萃取物,被劃分成二氯甲烷、乙酸乙酯、正丁醇與水可溶等部分,乙酸乙酯可溶部分進一步使用離心分配層析(CPC)、Sephadex LH-20管柱層析與RP-18管柱層析,等等一系列的分離純化後,得到 kaempferol-3-O-peracylated glucosides (18-21)、(2S)-6-C-β-glucopyranosyl-naringenin (22)、(2R)-6-C-β-glucopyranosyl naringenin (23)、(2S)-8-C-β-glucopyranosyl naringenin (24)、(2R)-8-C-β-glucopyranosyl naringenin (25)、(–)-epicatechin (26) 與 (7S,7'S,8R,8'R)-icariol A2 (27)。化合物22~27絕對立體構型的確認,係由所測得的CD圖譜與參考文獻進行比對。在這些化合物中,kaempferol-3-O-(3',4'-di-O-acetyl-2'-O-(Z)-p-coumaroyl-6'-O-(E)-p-coumaroyl)-β-glucopyranoside (20) 與 kaempferol-3-O-(3',4'-di-O-acetyl-2',6'-di-O-(Z)-p-coumaroyl)-β-glucopyranoside (21)為新化合物,其結構係由二維核磁共振光譜分析與質譜解析而確定。 | zh_TW |
dc.description.abstract | PartⅠ: α-Glucosidase inhibitors from Tinospora crispa leaves
Tinospora crispa (Linn.) Hook. f. et Thoms. (Menispermaceae) is a vine with warty stem and is widely distributed over tropical and subtropical Asia, including India, Thailand, Vietnam, Philippines, Indonesia, and Malaysia. The dried vines of this plant have been used as a folk medicine for many purposes and demonstrated to possess inhibitory activity against diabetes. Recent studies in our lab found borapetosides A and C, isolated from this vine, to be the active constituents possessing hypoglycemic activity with the mechanism of action related to activation of the insulin signaling pathway. Extension of such work on the leaf part, whose constituents have not been reported yet, found the ethanolic extract to be active against α-glucosidase, one of the therapeutic targets for type-2 diabetes mellitus. Thus, this study was aimed to disclose the active constituents from the leaf part of this folk plant. The ethanolic extract of Tinospora crispa leaves had shown inhibitory activity toward α-glucosidase. Bioassay guided fractionation and separation of this active extract with the aid of HPLC-SPE-NMR led to the isolation of 17 flavonoids, including 8 acylated glycosylflavonoids (6-11, 13, 15). Among them, isoorientin-2'-(E)-sinapate (6), isovitexin -2'-(E)-p-coumarate (8), cosmosiin-6'-(E)-ferulate (9), and cosmosiin-6'-(E)-cinnamate (15) are new compounds. Their structures were elucidated on the basis of NMR and mass spectroscopic analyse. From the enzyme inhibitory assay, isovitexin-2'-(E)-p-coumarate (8) showed the best activity against α-glucosidase with an IC50 value of 4.3 ± 1.4 μM. Isoorientin-2'-(E)-p-coumarate (7), the 3′-hydroxylated 8, however is much less active (IC50: 35.7 μM). Other acylated derivatives of cosmosiin, including 6'-(E)-ferulate (9), 6'-(E)-p-coumarate (10), 6'-(Z)-p-coumarate (11), and 6'-(E)-cinnamate (15), also exhibited inhibitory activities with the IC50 value of 8.8, 14.6, 10.1, and 11.3 μM, respectively. PartⅡ: Chemical investigation of Pasania dodoniifolia leaves Pasania dodoniifolia Hayata (Fagaceae), a medium-sized evergreen tree up to 9 m high and 10 cm in diameter, is an endemic species to southern Taiwan from medium to low attitude. Before our study, no chemical information about this plant had been reported. Thus, this study was aimed to investigate its chemical constituents. The ethanolic extract of its leaf was divided into fractions soluble in CH2Cl2, ethyl acetate, n-BuOH, and H2O. The EtOAc-soluble fraction was further chromatographed on a centrifugal partition chromatograph (CPC), Sephadex LH-20, and RP-18 columns to give four kaempferol 3-O-peracylated glucosides (18−21) in addition to (2S)-6-C-β-glucopyranosylnaringenin (22), (2R)-6-C-β-glucopyranosyl naringenin (23), (2S)-8-C-β-glucopyranosyl naringenin (24), (2R)-8-C-β-glucopyranosyl naringenin (25), l-epicatechin (26), and (7S,7'S,8R,8'R)-icariol A2 (27). The absolute configurations of compound 22~27 were determined by comparing their CD data with those reported. Among the isolated compounds, kaempferol-3-O-(3',4'-di-O-acetyl-2'-O-(Z)-p-coumaroyl-6'-O-(E)-p-coumaroyl)-β-glucopyranoside (20) and kaempferol-3-O-(3',4'-di-O-acetyl-2',6'-di-O-(Z)-p-coumaroyl)-β-glucopyranoside (21) are new compounds and their structures were elucidated by 2D NMR spectroscopic analyses and MS data. | en |
dc.description.provenance | Made available in DSpace on 2021-06-15T16:45:28Z (GMT). No. of bitstreams: 1 ntu-104-D97423006-1.pdf: 14462718 bytes, checksum: 82609c98424691fb0cfc6e8626e70860 (MD5) Previous issue date: 2015 | en |
dc.description.tableofcontents | 總目錄
口試委員審定書…………………………………………………………………………i Curriculum Vitae…………………………………………………………………...……ii 誌謝………………………………………………………………………..……………iii 中文摘要…………………………………………………………………...............…….I 英文摘要……………………………………………………………........…………….III 目錄…………………………………………………………………………….……….V 流程圖目錄 (List of schemes)……………………………………………………….VIII 表目錄 (List of tables)…………………………………………………………….... VIII 圖目錄 (List of figures)………………………………………………………………..IX 辭彙 (Glossary)………………………………………………………………………..XI 目錄 第一章 苦藤葉部抑制甲型葡萄糖水解酶活性成分之研究……………….1 壹、序論…………………………………………………………………...…………....1 1.1 Tinospora crispa植物功效與研究目的………………………………………….1 1.2 Tinospora crispa植物簡介...………………………………………...…………...2 1.3 防己科青牛膽屬(Tinospora)植物成分之成分研究…………………………….4 1.4 甲型葡萄糖水解酶抑制劑(α-glucosidase inhibitor)於糖尿病之應用...............15 1.5 HPLC-SPE-TT-NMR技術簡介………………………………………………...16 貳、實驗結果與討論…………………………………..…………………..………….17 2.1應用HPLC-SPE-TT-NMR 與 HPLC-HRESIMS技術分析Fr. B10…………18 2.2 Isoorientin, isovitexin與其衍生物 (1、3、6、7 & 8)…………………..…….24 2.2.1 Isoorientin (1)之結構解析………………………………………………….24 2.2.2 Isoorientin-2'-(E)-p-coumarate (7)之結構解析…………………………….24 2.2.3 Isoorientin-2'-(E)-sinapate (6)之結構解析…………………………………25 2.2.4 Isovitexin (3)之結構解析…………………...………………………………26 2.2.5 Isovitexin 2'-(E)-p-coumarate (8)之結構解析……………………………..26 2.3 Cosmosiin與其相關衍生物 (4-5、9-11、13 & 15)…………………………...27 2.3.1 Cosmosiin (apigenin-7-O-β-glucoside)(5)之結構解析…………………….27 2.3.2 Cosmosiin-6'-(E)-ferulate (9)之結構解析…………………………………28 2.3.3 Cosmosiin-6'-(E)-p-coumarate (10)、cosmosiin-6'-(Z)-p-coumarate (11) 及cosmosiin-6'-(E)-cinnamate (15)之結構解析………………………….29 2.3.4 Luteolin-7-O-β-glucoside (4)之結構解析………………………………….30 2.3.5 Luteolin-7-O-β-glucosyl-6'-(E)-p-cinnamate (13)之結構解析……………30 2.4 Flavonoid類化合物 (2、12、14、16 & 17)......................................................31 2.4.1 Orientin (luteolin-8-C-β-glucoside)(2)之結構解析………………………...31 2.4.2 Apigenin (12)之結構解析…………………………………………………..31 2.4.3 3'-O-methylluteolin (14)之結構解析……………………………………….32 2.4.4 Luteolin-4'-O-β-glucoside (16)之結構解析………………………………...32 2.4.5 Luteolin (17)之結構解析…………………………………………………...33 2.5 甲型葡萄糖水解酶之抑制活性測試結果……………………………………..34 2.6 討論…………………………………………………………………..…………36 2.7 結論……………………………………………………………………………..41 參、實驗方法………………………………………………………………………….42 3.1 儀器與材料……………………………………………………………………..42 3.1.1理化性質測定儀器…………………………………………………………42 3.1.2 成分分離之儀器、材料與方法…………………………..………..……...42 3.1.2.1層析分離……………………………………………………………….42 3.1.2.2 HPLC (High Performance Liquid Chromatography)…………………..43 3.1.2.3 HPLC-DAD-SPE-NMR儀器與分析方法.............................................43 3.1.2.4 HPLC-HRESIMS儀器與分析方法.......................................................44 3.2 試藥與溶劑……………………………………………………………………..45 3.3 植物來源………………………………………………………………………..45 3.4 萃取與分離純化………………………………………………………………..46 3.4.1萃取與正丁醇可溶部分之成分分離………………………………………46 3.4.2從Fr. B10中分離化合物1-15……………………………………………..47 3.5 甲型葡萄糖水解酶之活性試驗 (α-glucosidase activity assay)……………….49 3.5.1原理……………………………………………………………...………….49 3.5.2儀器與材料……………………………………………………...………….49 3.5.3步驟…………………………………………………………...…………….50 3.5.4 IC50值之測量……………………………………………………………….51 3.6 分子對接 (Molecular docking)………………………………...………………51 3.7化合物之物理數據...............................................................................................52 參考文獻……………………………………………………………………………….56 第二部分 柳葉石櫟葉部成分之研究……………..…………………………...63 壹、序論…………………………………………………………………...…………..63 1.1研究目的………………………………………………………………...………63 1.2 Pasania dodoniifolia Hayata植物簡介……………………………………...….63 1.3殼斗科柯屬(Pasania)植物成分之研究………………………………...………64 貳、實驗結果與討論…………………………………...……………………………..65 2.1化合物18–21之結構解析………………………………………………..…….66 2.2化合物22–25之結構解析……………………………………………..……….71 2.3化合物26之結構解析……………………………………………...…………..75 2.4化合物27之結構解析……………………………………………...…………..76 2.5結論…………………………………………………...…………………………77 參、實驗方法…………………………………...……………………………………..78 3.1 儀器與材料……………………………………………………………………..78 3.1.1理化性質測定儀器…………………………………………………………78 3.1.2 成分分離之儀器及材料…………………………………………………...78 3.1.2.1層析分離……………………………………………………………….78 3.1.2.2 HPLC (High Performance Liquid Chromatography)…………………..79 3.2 試藥與溶劑……………………………………………………………………..79 3.3 植物來源………………………………………………………………………..80 3.4 萃取與分離純化………………………………………………………………..80 3.5 化合物之物理數據..............................................................................................82 參考文獻……………………………………………………………………………….85 附圖…………………………………………………………………………………….87 流程圖目錄 (List of schemes) Scheme 1. Fractionation and isolation scheme for the ethanolic extract of T. crispa leaves……….………………………………………..………….. 48 Scheme 2. Isolation scheme for the ethanolic extract of P. dodoniifolia leaves…...…...81 表目錄 (List of tables) Table 1. Compounds isolated from Tinospora plants…………………….…………....4-8 Table 2. α-Glucosidase inhibitors in clinical use…...…………………………………..15 Table 3. HPLC-HRESIMS data of compounds in fraction B10 and their UV spectroscopic data, obtained from the HPLC-SPE-NMR analysis…….……...19 Table 4. 1H NMR Spectroscopic data (δ/ppm, mult., J in Hz) of compounds 1–3, 6–8, 12 & 14, obtained from HPLC-SPE-NMR (CD3OD, 600 MHz)………….….21 Table 5. 1H NMR Spectroscopic data (δ/ppm, mult., J in Hz) of compounds 4–5, 9–11, 13 & 15, obtained from HPLC-SPE-NMR (CD3OD, 600 MHz)…………....22 Table 6. 13C (150 MHz), 1H NMR, and HMBC (600 MHz) data of the isolated 7, 8, and 9…………………..……………………………………………………....23 Table 7. Anti-α-glucosidase effect of isolated flavone glycosides (IC50, μM)…………34 Table 8. Flavonoids and polyphenolics as α-glucosidase inhibitors…………..……37-38 Table 9. 1H NMR data of compounds 18–21 (δH /ppm, mult., J/Hz) (CD3OD, 600 MHz)……………................................………..……………….69 Table 10. 13C NMR and HMBC data of compound 18–21 (δC /ppm, mult.) (CD3OD, Bruker AVIII-600)…………………...……………………..……..70 Table 11. 1H NMR data (δH/ppm, mult., J/Hz) of compounds 22–25 (C5D5N, 600 MHz)…..………………………………….…..……………….73 Table 12. 13C NMR and HMBC data of compounds 22–25 (C5D5N, Bruker AVIII-600)………………....…………………….…………74 Table 13. 1H & 13C NMR data of compound 26 (CD3OD, Bruker AV-400)……...…… 75 Table 14. 1H & 13C NMR data of compound 27 (CD3OD, Bruker AV-400)……………76 圖目錄 (List of figures) Figure 1.苦藤 Tinospora crispa (Linn.) Hook. f. et Thoms. (Menispermaceae).............3 Figure 2. Structures of isolated compounds from Tinospora plants…………......…..9-14 Figure 3. Structures of α-glucosidase inhibitors in clinical use………………………...15 Figure 4. Principle of hyphenated LC-SPE-TT-NMR…………………….……………16 Figure 5. Structures of characterized compounds from n-BuOH soluble fraction of T. crispa leaves................................................................................................18 Figure 6. Reverse-phase HPLC profile of fraction B10 for HPLC-SPE-NMR experiment, monitored at 254 nm……………………………………………19 Figure 7. 1H NMR spectra of 1~15 (CD3OD, 600 MHz) obtained from the HPLC-SPE-NMR of fraction B10………………………………….................................20 Figure 8. Inhibitory effect of the EtOH extract and subfractions against α-glucosidase.35 Figure 9. The diagrammatic representation of the interactions between 7, 8, and the constructed human intestinal maltase-glucoamylase (α-glucosidase)……….36 Figure 10. Flavonoids and polyphenolics asα-glucosidase inhibitors……..………..39-40 Figure 11. Principle of α-glucosidase inhibition assay……………………………...….49 Figure 12. 96-Well plate sample arrangement (n=3)……………………...….………...50 Figure 13.柳葉石櫟 Pasania dodoniifolia Hayata (Fagaceae)………………………..64 Figure 14. Structures of characterized compounds from P. dodoniifolia leaves…….…65 Figure 15. CD spectra of compounds 22 ~25…………………………………………..72 | |
dc.language.iso | zh-TW | |
dc.title | 第一部分:苦藤葉部抑制甲型葡萄糖水解酶活性成分之研究
第二部分:柳葉石櫟葉部成分之研究 | zh_TW |
dc.title | Part 1 α-Glucosidase inhibitors from Tinospora crispa leaves
Part 2 Chemical investigation of Pasania dodoniifolia leaves | en |
dc.type | Thesis | |
dc.date.schoolyear | 103-2 | |
dc.description.degree | 博士 | |
dc.contributor.oralexamcommittee | 陳益昇,陳繼明,李安榮,張嘉銓 | |
dc.subject.keyword | 苦藤,甲型葡萄糖水解?抑制劑,黃酮醯化?,柳葉石櫟,葉部,黃酮類, | zh_TW |
dc.subject.keyword | Tinospora crispa,α-Glucosidase inhibitors,Acylated glucosylflavones,Pasania dodoniifolia,leaves,flavonoids, | en |
dc.relation.page | 203 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2015-08-10 | |
dc.contributor.author-college | 藥學專業學院 | zh_TW |
dc.contributor.author-dept | 藥學研究所 | zh_TW |
顯示於系所單位: | 藥學系 |
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