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DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 李水盛 | |
dc.contributor.author | Chen-Che Wu | en |
dc.contributor.author | 吳承哲 | zh_TW |
dc.date.accessioned | 2021-06-16T13:36:55Z | - |
dc.date.available | 2016-09-24 | |
dc.date.copyright | 2013-09-24 | |
dc.date.issued | 2013 | |
dc.date.submitted | 2013-07-16 | |
dc.identifier.citation | 參考文獻
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I., Ishimatsu, M., Ageta, M., Nishioka, I., Tannins and related compounds. LXXVI. Isolation and characterization of cercidinins A and B and cuspinin, unusual 2,3-(R)-hexahydroxydiphenoyl glucoses from Cercidiphyllum japonicum and Castanopsis cuspidata var. sieboldii. Chem. Pharm. Bull. 1989, 37, 50-53. 14. Ageta, M., Nonaka, G. I., Nishioka, I., Tannins and related compounds. LXVII. Isolation and characterization of castanopsinins A-H, novel ellagitannins containing a triterpenoid glycoside core, from Castanopsis cuspidata var. sieboldii NAKAI. (3). Chem. Pharm. Bull. 1988, 36, 1646-1663. 15. Nonaka, G. I., Ishimaru, K., Mihashi, K., Iwase, Y., Ageta, M., Nishioka, I., Tannins and related compounds. LXIII. Isolation and characterization of monogolicains A and B, novel tannins from Quercus and Castanopsis species. Chem. Pharm. Bull. 1988, 36, 857-869. 16. The expert committee on the diagnosis and classification of diabetes mellitus. 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Tanaka, N., Tanaka, T., Fujioka, T., Fujii, H., Mihashi, K., Shimomura, K., Ishimaru, K., An ellagic compound and iridoids from Cornus capitata root cultures. Phytochemistry 2001, 57, 1287-1291. 23. Bai, N. S., He, K., Roller, M., Zheng, B. L., Chen, X. Z., Shao, Z. G., Peng, T. S., Zheng, Q. Y., Active compounds from Lagerstroemia speciosa, Insulin-like glucose uptake-stimulatory/inhibitory and adipocyte differentiation-inhibitory activities in 3T3-L1 cells. J. Agr. Food. Chem. 2008, 56, 11668-11674. 24. Zhu, X. D., Dong, X. J., Wang, W. F., Ju, P., Luo, S. D., Phenolic compounds from Viburnum cylindricum. Helv. Chim. Acta. 2005, 88, 339-342. 25. Argoti, J. C., Linares-Palomino, P. J., Salido, S., Ramirez, B., Insuasty, B., Altarejos, J., On-line activity screening for radical scavengers from Baccharis Chilco. Chem. Biodivers. 2013, 10, 189-197. 26. Si, C. L., Zhang, Y., Zhu, Z. Y., Liu, S. C., Chemical constituents with antioxidant activity from the pericarps of Juglans sigillata. Chem. Nat. Compd. 2011, 47, 442-445. 27. Fecka, I., Cisowski W., Tannins and flavonoids from the Erodium cicutarium herb. Z. Naturforschung. B 2005, 60b, 555-560. 28. Bilia, A. R., Lucia C., Mendez, J., Morelli, I., Phytochemical investigations of Licania genus. Flavonoids from Licania pyrifolia. Pharm. Acta Helv. 1996, 7, 199-204. 29. Nandy, A. K., Podder, G., Sahu, N. P., Mahato, S. B., Triterpenoids and their glucosides from Terminalia bellerica. Phytochemistry 1989, 28, 2769-2772. 30. Wang, Y. H., Xiang, L. M., Chen, M., Zhang, Z. X., He, X. J., Substrate specificity for the 2α-hydroxylation of ursolic acid by Alternaria alternata and the antitumor activities of those metabolites. J. Mol. Catal. B-Enzym. 2012, 83, 51-56. 31. Xiaoan, W., Hongbin, S., Jun, L., Keguang, C., Pu, Z., Liying, Z., Jia, H., Luyong, Z., Peizhou, N., Spyros, E. Z., Demetres, D. L., Kyra-Melinda, A., Thanasis, G. Joseph, M. H., Nikos, G. O., Naturally Occurring Pentacyclic Triterpenes as Inhibitors of Glycogen Phosphorylase:Synthesis, Structure-Activity Relationships, and X-ray Crystallographic Studies. J. Med Chem, 2008, 51, 3540-3554 | |
dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/62257 | - |
dc.description.abstract | 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。 | zh_TW |
dc.description.abstract | 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. | en |
dc.description.provenance | Made available in DSpace on 2021-06-16T13:36:55Z (GMT). No. of bitstreams: 1 ntu-102-R00423002-1.pdf: 7233478 bytes, checksum: 9fbcf0856eb8784a4f9ffa4dd3c96ee4 (MD5) Previous issue date: 2013 | en |
dc.description.tableofcontents | 總目錄
口試委員會審定書 i 誌謝 ii 中文摘要 iii 英文摘要(Abstract) iv 目錄 v 流程圖目錄 viii 表目錄 ix 圖目錄 x 詞彙縮寫(Glossary of Abbreviations) xiii 目錄 第一章 緒論 1 1.1 研究目的 1 1.2長尾尖葉櫧之植物簡介 2 1.3糖尿病及臨床治療藥物 7 1.3.1糖尿病之盛行率 7 1.3.2糖尿病之分類 7 1.3.3糖尿病之病因及併發症 7 1.3.4糖尿病之治療藥物 8 1.3.5臨床上使用的α-glucosidase抑制劑及其特點 11 第二章 實驗結果與討論 13 2.1黃酮類成分及沒食子酸衍生物之結構解析 13 2.1.1 Ellagic acid 成分 1, 2, 5 之結構解析 15 2.1.1.1 3,3'-Di-O-methylellagic acid- 4-O-α-L- arabinofuranoside (1) 15 2.1.1.2 3,3'-Di-O-methylellagic acid (2) 17 2.1.1.3 3,3',4'-Tri-O-methylellagic acid-4-O-α-L-arabinofuranoside (5) 18 2.1.2 Chlorogenic acid methyl ester (3)及Chlorogenic acid (6) 21 2.1.3 Gallic acid (7) 23 2.1.4 (-)-3-O-Galloyl-shikimic acid (8) 24 2.1.5 Kaempferol-3-O-α-L-rhamnopyranoside (4) 25 2.1.6 Castanopsinin E, 9a/b, castanopsinin A, 10a/b, 及castanopsiniin A 13a/b 27 2.2 Castanopsinin Aa (10a) / Ab (10b)之結構解析 29 2.2.1 3,23-(R)-2α,3β,23,24-Tetrahydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside (10a)及3,23-(R)-2α,3β,23,24-tetrahydroxyurs-12-en-28-oic acid 28-O-β-D-glucopyranoside (10b)之結構解析 29 2.3 Castanopsinins之結構修飾研究 31 2.3.1 2α,3β,23,24-Tetrahydroxyolean-12-en-28-oic acid (11a, belleric acid) 及-urs -12-en-28-oic acid (11b)混合物之製備 33 2.3.2 Belleric acid benzyl ester (12a)及2α,3β,23,24-tetrahydroxyurs-12-en-28-oic acid benzyl ester (12b)混合物之製備 34 2.3.3化合物11a及11b之製備 34 2.3.4 2α,3β,23,24-Tetrahydroxyolean-12-en-28-oic acid (11a, belleric acid) 、 2α,3β,23,24-tetrahydroxyurs-12-en-28-oic acid (11b)、belleric acid benzyl ester (12a)及2α,3β,23,24-tetrahydroxyurs-12-en-28-oic acid benzyl ester (12b)之結構解析 35 2.3.4.1 Belleric acid (11a)之結構解析 36 2.3.4.2 2α,3β,23,24-Tetrahydroxyurs-12-en-28-oic acid (11b)之結構解析 40 2.3.4.3 Belleric acid benzyl ester (12a)之結構解析 42 2.3.4.4 2α,3β,23,24-Tetrahydroxyurs-12-en-28-oic acid benzyl ester (12b)之結構解析 44 2.4甲型葡萄糖水解酶抑制活性之結果與討論 46 2.4.1化合物1-8之活性 46 2.4.2化合物9a/b, 10a/b, 13a/b之活性 46 2.4.3化合物10a及10b之IC50 47 2.4.4化合物11a, 11b, 12a, 12b, ursolic acid與oleanolic acid之活性 48 2.5結論 49 第三章 實驗方法 51 3.1儀器與材料 51 3.1.1物理數據測定儀器 51 3.1.2成分分離之儀器及材料 51 3.1.3溶劑 52 3.1.4試藥 52 3.1.5甲型葡萄糖水解酶之活性試驗(α-glucosidase assay)所需之試劑及儀器 52 3.2長尾尖葉櫧葉部成分之抽取與分離(第一部分) 53 3.2.1正丁醇可溶部分之成分分離 53 3.3長尾尖葉櫧葉部成分之抽取與分離(第二部分) 57 3.3.1 Castanopsinins類化合物之製備 58 3.4 Castanopsinins之結構修飾研究 60 3.4.1 2α,3β,23,24-Tetrahydroxyolean-12-en-28-oic acid (11a, belleric acid)及-urs -12-en-28-oic acid (11b)混合物之製備 60 3.4.2 Belleric acid benzyl ester (12a) 及2α,3β,23,24-tetrahydroxyurs-12-en-28-oic acid benzyl ester (12b)混合物之製備 60 3.4.3 化合物11a及11b之製備 61 3.5甲型葡萄糖水解酶之抑制活性試驗(α-glucosidase activity assay) 62 3.5.1原理 62 3.5.2酵素活性 62 3.5.3單位實驗方法 62 3.5.3.1試劑配置 62 3.5.3.2正向控制組 63 3.5.3.3實驗步驟 63 3.6 化合物 1-13各化合物之物理數據 65 參考文獻 69 附 圖 72 流程圖目錄(List of Schemes) Scheme 1. Alkaline hydrolysis of n-BuOH fraction of Castanopsis cupidata var. carlesii 33 Scheme 2. Benzylation of 11a/b 34 Scheme 3. Hydrogenolysis (Debenzylation) of 12a and 12b 35 Scheme 4. Extraction and fractionation of the leaves of Castanopsis cuspidata var. carlesii 53 Scheme 5. Isolation scheme of 1-8, 9a/b, 10a/b and 13a/b from n-BuOH soluble fraction 56 Scheme 6. Extraction and fractionation of the leaves of Castanopsis cuspidata var. carlesii (Part 2) 57 Scheme 7. Isolation scheme of 10a and 10b 59 Scheme 8. The principle of α-glucosidase assay 62 表目錄(List of Tables) Table 1. Chemical constituents isolated from the Castanopsis plants 3 Table 2. Characteristics of insulin preparations 8 Table 3. Orally administered antihyperglycemic agents (OHAs) for diabetes 9 Table 4. Potential combinations of OHAs for the treatment of type 2 diabetes 10 Table 5. Characteristics of α-glucosidase inhibitors in clinical use 12 Table 6. 1H and 13C NMR data of 1 (C5D5N) 16 Table 7. 1H NMR data of 2 (CDCl3:CD3OD=5:1) 17 Table 8. 1H and 13C NMR, Key HMBC and NOESY data of 5 (CDCl3:CD3OD=2:1, Bruker AVIII 600) 20 Table 9. 1H and 13C NMR data of 3 and 6 (CD3OD) 22 Table 10. 1H and 13C NMR data of 7 (CD3OD) 23 Table 11. 1H and 13C NMR data of 8 (CD3OD) 24 Table 12. 1H and 13C NMR data of 4 (CD3OD) 26 Table 13. 13C NMR data of 9a/b, 10a/b and 13a/b (C5D5N) 28 Table 14. 13C NMR data of 10a and 10b (C5D5N) 30 Table 15. Structures of castanopsinins A-H 32 Table 16. 1H and 13C NMR, Key HMBC and NOESY data of 11a (C5D5N, Bruker AV-III 600) 38 Table 17. Comparison of 13C NMR data and reported reference of belleric acid (2α,3β,23,24-tetrahydroxyolean-12-en-28-oic acid, 11a) (C5D5N) 39 Table 18. 1H and 13C NMR data of 11b (C5D5N) 41 Table 19. 1H and 13C NMR data of 12a (CD3OD) 43 Table 20. 1H and 13C NMR data of 12b (CD3OD) 45 圖目錄(List of Figures) Figure 1. Botanical morphology of Castanopsis cuspidata (Thunb. ex Murray) Schottky var. carlesii (Hemsl.) Yamazaki f. carlesii 2 Figure 2. Major target organs and action of orally administered antihyperglycemic agents in type 2 diabetes mellitus 10 Figure 3. Structures of α-glucosidase inhibitors in clinical use 12 Figure 4. Structures of compounds (1-8, 9a/b, 10a/b, 13a/b) from the n-BuOH-soluble fraction of the leaves of Castanopsis cuspidata var. carlesii 14 Figure 5. CD spectrum of 1 (acetonitrile) 17 Figure 6. Key NOESY and HMBC correlations of 3,3',4'-tri-O-methylellagic acid-4-α-L-arabinofuranoside (5) 19 Figure 7. CD spectrum of 5 (acetonitrile) 19 Figure 8. Structures of 9a/b, 10a/b and 13a/b 31 Figure 9. Key HMBC and NOESY correlations of belleric acid (11a) 37 Figure 10. Inhibition of compounds 1-8 against α-glucosidase 46 Figure 11. Inhibition of compounds 9a/b, 10a/b and 13a/b against α-glucosidase 47 Figure 12. Exploration of IC50 value of Castanopsinin A (10a/10b) 48 Figure 13. Inhibition of compounds 11a, 11b, 12a and 12b, ursolic acid and oleanolic acid against α-glucosidase 49 Figure 14. HPLC chromatograms of Fr. 3-7-6, Fr. 3-7-6-1 and Fr. 3-7-6-3 55 Figure 15. HPLC chromatograms of Fr. 2-3-5 58 Figure 16. HPLC chromatograms of 12a/12b 61 Figure 17. 1H NMR spectrum of 1 (DMSO-d6, 200 MHz) 73 Figure 18. 13C NMR spectra (BBD, bottom; DEPT 135, middle; DEPT 90, top) of 1 (DMSO-d6, 50 MHz) 74 Figure 19. 1H NMR spectrum of 2 [CD3OD-CDCl3 (1:5), δ (CD2HOD) 3.30, 200 MHz] 75 Figure 20. 1H NMR spectrum of 3 (CD3OD, 200 MHz) 76 Figure 21. 13C NMR spectra (BBD, bottom; DEPT 135, middle; DEPT 90, top) of 3 (CD3OD, 50 MHz) 77 Figure 22. 1H NMR spectrum of 4 (CD3OD, 400 MHz) 78 Figure 23. 13C NMR spectra (BBD, bottom; DEPT 135, middle; DEPT 90, top) of 4 (CD3OD, 100 Hz) 79 Figure 24. 1H NMR spectrum of 5 [CD3OD-CDCl3 (1:2), δ (CD2HOD) 3.30 ppm, 600 MHz] 80 Figure 25. 13C NMR spectra (BBD, bottom; DEPT 135, middle; DEPT 90, top) of 5 [CD3OD-CDCl3 (1:2), δ (CD2HOD) 49.0 ppm, 150 MHz] 81 Figure 26. COSY spectrum of 5 [CD3OD-CDCl3 (1:2), δ (CD2HOD) 3.30 ppm, 600 MHz] 82 Figure 27. NOESY spectrum of 5 [CD3OD-CDCl3 (1:2), δ (CD2HOD) 3.30 ppm, 600 MHz] 83 Figure 28. HSQC spectrum of 5 [CD3OD-CDCl3 (1:2), δ (CD2HOD) 3.30 ppm, 600 MHz] 84 Figure 29. HMBC spectrum of 5 [CD3OD-CDCl3 (1:2), δ (CD2HOD) 3.30 ppm, 600 MHz] 85 Figure 30. 1H NMR spectrum of 6 (CD3OD, 400 MHz) 86 Figure 31. 13C NMR spectra (BBD, bottom; DEPT 135, middle; DEPT 90, top) of 6 (CD3OD, 100 MHz) 87 Figure 32. 1H NMR spectrum of 7 (CD3OD, 200 MHz) 88 Figure 33. 13C NMR spectra (BBD, bottom; DEPT 135, middle; DEPT 90, top) of 7 (CD3OD, 50 MHz) 89 Figure 34. 1H NMR spectrum of 8 (CD3OD, 400 MHz) 90 Figure 35. 13C NMR spectra (BBD, bottom; DEPT 135, middle; DEPT 90, top) of 8 (CD3OD, 100 MHz) 91 Figure 36. 1H NMR spectrum of 9a/b (C5D5N, 600 MHz) 92 Figure 37. 13C NMR spectra (BBD, bottom; DEPT 135, middle; DEPT 90, top) of 9a/b (C5D5N, 150 MHz) 93 Figure 38. 1H NMR spectrum of 10a/b (C5D5N, 600 MHz) 94 Figure 39. 13C NMR spectra (BBD, bottom; DEPT 135, middle; DEPT 90, top) of 10a/b (C5D5N, 150 MHz) 95 Figure 40. 1H NMR spectrum of 10a (C5D5N, 600 MHz) 96 Figure 41. 13C NMR spectrum of 10a (C5D5N, 150 MHz) 97 Figure 42. 1H NMR spectrum of 10b (C5D5N, 600 MHz) 98 Figure 43. 13C NMR spectrum of 10b (C5D5N, 150 MHz) 99 Figure 44. 1H NMR spectrum of 11a (C5D5N, 600 MHz) 100 Figure 45. 13C NMR spectra (BBD, bottom; DEPT 135, middle; DEPT 90,top) of 11a (C5D5N, 150 MHz) 101 Figure 46. COSY spectrum of 11a (C5D5N, 600 MHz) 102 Figure 47. NOESY spectrum of 11a (C5D5N, 600 MHz) 103 Figure 48. HSQC spectrum of 11a (C5D5N, 600 MHz) 104 Figure 49. HMBC spectrum of 11a (C5D5N, 600 MHz) 105 Figure 50. 1H NMR spectrum of 11b (C5D5N, 400 MHz) 106 Figure 51. 13C NMR spectra (BBD, bottom; DEPT 135, middle; DEPT 90,top) of 11b (C5D5N, 100 MHz) 107 Figure 52. 1H NMR spectrum of 12a (CD3OD, 400 MHz) 108 Figure 53. 13C NMR spectra (BBD, bottom; DEPT 135, middle; DEPT 90, top) of 12a (CD3OD, 100 MHz) 109 Figure 54. 1H NMR spectrum of 12b (CD3OD, 400 MHz) 110 Figure 55. 13C NMR spectra (BBD, bottom; DEPT 135, middle; DEPT 90, top) of 12b (CD3OD, 100 MHz) 111 Figure 56. 1H NMR spectrum of 13a/b (C5D5N, 600 MHz) 112 Figure 57. 13C NMR spectra (BBD, bottom; DEPT 135, middle; DEPT 90, top) of 13a/b (CD3OD, 150 MHz) 113 | |
dc.language.iso | zh-TW | |
dc.title | 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 | zh_TW |
dc.title | Active constituents from Castanopsis cuspidata var. carlesii against α-glucosidase and chemical modification of castanopsinins | en |
dc.type | Thesis | |
dc.date.schoolyear | 101-2 | |
dc.description.degree | 碩士 | |
dc.contributor.oralexamcommittee | 陳春雄,林雲蓮,張嘉銓 | |
dc.subject.keyword | 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, | zh_TW |
dc.subject.keyword | Diabetes mellitus,oral antidiabetic agents,α-glucosidase,Castanopsis cuspidata var. carlesii,triterpenoids, | en |
dc.relation.page | 113 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2013-07-17 | |
dc.contributor.author-college | 醫學院 | zh_TW |
dc.contributor.author-dept | 藥學研究所 | zh_TW |
顯示於系所單位: | 藥學系 |
文件中的檔案:
檔案 | 大小 | 格式 | |
---|---|---|---|
ntu-102-1.pdf 目前未授權公開取用 | 7.06 MB | Adobe PDF |
系統中的文件,除了特別指名其著作權條款之外,均受到著作權保護,並且保留所有的權利。