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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 張嘉銓 | |
dc.contributor.author | Tzu-Yun Chou | en |
dc.contributor.author | 周姿妘 | zh_TW |
dc.date.accessioned | 2021-06-16T02:39:11Z | - |
dc.date.available | 2020-07-01 | |
dc.date.copyright | 2015-09-24 | |
dc.date.issued | 2015 | |
dc.date.submitted | 2015-07-23 | |
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dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/54080 | - |
dc.description.abstract | 本論文包含兩部分: 第一部分:北冬蟲夏草之成分分析之研究 北冬蟲夏草(Cordyceps militaris)是使用多年的中草藥具有許多活性,例如:抗發炎、抗糖尿病、抗腫瘤等功效。由於天然的北冬蟲夏草的來源不足,因此人工培養之北蟲草為目前主要的生產方式。本研究探討以白米(CM-A)、白米添加3%茶葉(CM-B)以及白米添加3%茶蠶砂(CM-C)等三種培養基培養出北冬蟲夏草其活性成分的差異。取白米培養得到的蟲草子實體乙醇抽取物,極性劃分成氯仿、乙酸乙酯、正丁醇和水可溶部分及沉澱物,氯仿及正丁醇可溶部分經Sephadex LH-20、半製備HPLC等管柱層析法於得到1個新化合物及9個已知結構,分別為phenylalanine (1)、cordycedipeptide B (2)、nicotinic acid (3)、tryptophan (4)、N6-(2-hydroxyethyl)-adenosine (5)、uracil (6)、uridine (7)、cordycepin (8)、ergosterol (9) 和 mannitol (10)。其中化合物2為首次於天然物中分離,為含有ornithine骨架的類雙肽新化合物。大部分所分離到的化合物與天然蟲草的成分是相似的;化合物5並未自此子實體中被發現,且蟲草素(cordycepin)含量比天然的蟲草多(125倍)。以白米培養之北蟲草子實體成分與另兩種培養基培養的比較,3 %之茶葉添加物在化合物5、8及9含量上無顯著影響;3 %茶蠶砂添加物所培養的子實體中並無發現化合物9,但化合物5的含量增加2~3倍。這些培養的北蟲草子實體因培養的方式不同而有成分上的改變,可以進一步作為增加特定活性成分的方法。 第二部分:茶蠶砂之成分分析之研究 蠶砂為蠶排泄物,具有促進傷口癒合、抗腫瘤、降血糖及血脂等功能。茶蠶(Andraca theae)為危害茶樹的害蟲。茶蠶砂為其排泄物,其化學成分尚未有任何報告,其可能用途亦未有報告。基於上述原因本研究以層析法分離茶蠶砂之化學成分,釐清與茶葉組成的差異,進而評估茶蠶砂開發為藥用的潛力。 茶蠶砂的乙醇萃取物經極性劃分成氯仿、乙酸乙酯、正丁醇和水可溶部分,乙酸乙酯可溶部分利用Sephadex LH-20、CPC、Lobar RP-18和半製備HPLC等管柱分離得到1個生物鹼(11)、3個羧酸類(12、13及15)及10個黃酮類(14與16-24)。黃酮類化合物16、17及19-24之總含量比茶葉多4.2倍,所以茶蠶這些化合物可能無法為所利用,或經其腸道細菌轉化而排出,化合物11並未見於茶葉成分,是茶蠶代謝咖啡因的產物。故此茶蠶砂可成為提供前述黃酮類活性成分的重要來源。 | zh_TW |
dc.description.abstract | This dissertation includes two parts: Part 1. Chemical investigation of the Cordyceps militaris Cordyceps militaris (L.) Link is a traditional Chinese medicine, with various biological activities, including anti-inflammation, anti-tumor, and anti-diabetes. Because of its limited natural supply, culture of C. militaris has become the major source. The aim is to discuss the active ingredients of the cultured C. militaris which was cultured with different sources such as rice (CM-A), rice plus 3 % tea leaves (CM-B) and rice plus 3 % feces of Andraca bipunctata (CM-C). The ethanolic extract of dried C. militaris (cultured with rice) was divided into fractions soluble in CHCl3, EtOAc, n-BuOH and a precipitate via liquid-liquid partitioning process. The n-BuOH- and CHCl3- soluble fractions were separated by chromatographic methods to afford ten compounds (1-10). Through NMR and MS spectroscopic analyse, they were characterized as phenylalanine (1), cordycedipeptide B (2), nicotinic acid (3), tryptophan (4), N6-(2-hydroxyethyl)-adenosine (5), uracil (6), uridine (7), cordycepin (8), ergosterol (9), and mannitol (10). Of that cordycedipeptide B (2) is a new compound. The chemical components from cultured C. militaris are found to be similar to those from the natural one. Among them, N6-(2-hydroxyethyl)-adenosine (5) has never been identified from this species, and the content of cordycepin from the cultured is 125 folds more than that from the nature. This study indicates that the ingredients of CM-B has no significant difference from those of CM-A. Nevertheless, the amount of N6-(2-hydroxyethyl)-adenosine (5) in CM-C is increased 2~3 folds. With different culture conditions, the compounds of C. militaris are not the same. Hence, the culture conditions can be used as a tool to produce specific active compound(s). Part 2. Chemical investigation of the Andraca theae droppings. Silkworm Feculae (droppings of silkworm), a traditional Chinese medicine possess to a number of bioactivities, including promotion of wound healing, anti-tumor, anti-hyperglycemia, and anti-hyperlipidemia. Tea silkworm (Andraca theae) is a common tea pestsin, and its droppings have not reported yet, nor chemical constitute of its medical use. For the above reasons, the present study was aimed to isolate the chemical constituents of tea silkworm feces by chromatographic methods, and evaluate its potential for medical uses. The ethanolic extract of the dried droppings of tea silkworm was divided into fractions soluble in CHCl3, EtOAc, n-BuOH, and a precipitate via liquid-liquid partitioning process. The EtOAc-soluble fractions was separated by chromatographic methods including Sephadex LH-20, CPC, and RP-18 column to afford 14 compounds (11-24). They were characterized as one xanthine alkaloid (11), three benzoic acids (12, 13 and 15) and ten flavonoids (14, 16-24). 1,7-Dimethyl xanthine (11) is not present in tea leaves. The amount of compounds 16, 17, and 19-24 in the feces is about 4.2 folds related to that of tea droppings. Thus, these compounds are not absorted and eliminated directly, except for 11, which might be transformed from caffine by microflora of the insect. This study suggest the tea silkworm droppings to be a good source of the bioactive flavonoids from tea leaves. | en |
dc.description.provenance | Made available in DSpace on 2021-06-16T02:39:11Z (GMT). No. of bitstreams: 1 ntu-104-R02423001-1.pdf: 14112906 bytes, checksum: 07b60f64a309c415cd52596ed3bb2864 (MD5) Previous issue date: 2015 | en |
dc.description.tableofcontents | 總目錄 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)………………………………………IX 圖目錄 (List of figures)…………………………………………X 辭彙 (Glossary)………………………………………………….XI 目錄 第一章 :北冬蟲夏草之成分分析 1 1. 緒論及研究目的 1 1.1 研究目的 1 1.2 北冬蟲夏草之簡介 2 1.3 北蟲草之文獻回顧 3 1.3.1 北蟲草生物活性之研究 3 1.3.2 天然蟲草與培養蟲草主要活性成分含量比較 4 1.4 蟲草屬(Cordyceps)成分之文獻回顧 5 2. 實驗結果與討論 19 2.1 胺基酸類 20 2.1.1 Phenylalanine (1)之結構解析 20 2.1.2 Tryptophan (4)之結構解析 21 2.2 核苷類 22 2.2.1 N6-(2-hydroxyethyl)adenosine (5)之結構解析 22 2.2.2 Cordycepin (8)之結構解析 23 2.2.3 Uracil (6)之結構解析 25 2.2.4 Uridine (7)之結構解析 25 2.3 其他 27 2.3.1 Cordycedipeptide B (2)之結構解析 27 2.3.2 Nicotinic acid (3)之結構解析 29 2.3.3 Ergosterol (9)之結構解析 30 2.3.4 Mannitol (10)之結構解析 32 2.4 結論 33 3. 實驗部分 35 3.1 儀器與材料 35 3.1.1 理化性質測定儀器 35 3.1.2 成分分離之儀器及材料 35 3.1.3 試劑與溶媒 36 3.1.4 薄層層析展開系統 36 3.2 北蟲草材料來源 36 3.3 北蟲草子實體成分萃取與純化 37 3.3.1 白米培養之子實體(CM-A) 37 3.3.1.1 正丁醇可溶部分之分離 37 3.3.1.2 氯仿可溶部分之分離 40 3.3.2 白米添加3%茶葉培養之子實體(CM-B) 42 3.3.2.1 正丁醇可溶部分之分離與純化 43 3.3.2.2 氯仿可溶部分之分離與純化 44 3.3.3 白米添加3%茶蠶砂培養之子實體(CM-C) 44 3.3.3.1 正丁醇可溶部分之分離與純化 45 3.3.3.2 氯仿可溶部分之分離與純化 46 3.4 物理性質 47 第二章 茶蠶砂之化學成分研究 49 1. 緒論及研究目的 49 1.1 茶蠶砂簡介與研究目的 49 1.2 成分之文獻回顧 50 2. 實驗結果與討論 62 2.1 生物鹼 63 2.1.1 1,7-Dimethyl xanthine (11)之結構解析 63 2.2 苯甲酸衍生物 (Benzoic acid derivatives) 64 2.2.1 3-O-Methylgallic acid (12)之結構解析 64 2.2.2 4-Hydroxybenzoic Acid (13)之結構解析 64 2.2.3 Gallic acid (15)之結構解析 64 2.3 黃酮類 (Flavonols) 66 2.3.1 (−)-Catechin (16)之結構解析 66 2.3.2 (−)-Epicatechin (17)之結構解析 66 2.3.3 (+)-Gallocatechin (20)之結構解析 68 2.3.4 (–)-Epigallocatechin (21)之結構解析 68 2.3.5 (–)-3'-O-Methyl-epigallocatechin gallate (22)之結構解析 70 2.3.6 (–)-Epigallocatechin gallate (23)之結構解析 70 2.3.7 (−)-Epicatechin gallate (24) 之結構解析 70 2.3.8 Kaempferol 3-O-rutinoside (14)之結構解析 73 2.3.9 Isomyricitrin (18)之結構解析 75 2.3.10 Quercetin 3-O-β-D-galactopyranoside (19)之結構解析 77 2.4 結論 79 3. 實驗部分 81 3.1 儀器與材料 81 3.1.1 理化性質測定儀器 81 3.1.2 成分分離之儀器及材料 81 3.1.3 試劑與溶媒 82 3.1.4 薄層層析展開系統 82 3.2 茶蠶砂材料來源 82 3.3 茶蠶砂成分萃取與純化 83 3.3.1 乙酸乙酯可溶部分之分離 84 3.3.1.1 化合物11之純化 84 3.3.1.2 化合物12, 13, 14之純化 84 3.3.1.3 化合物15之純化 84 3.3.1.4 化合物16, 17之純化 85 3.3.1.5 化合物18, 19之純化 85 3.3.1.6 化合物20, 21之純化 85 3.3.1.7 化合物22之純化 85 3.3.1.8 化合物23, 24之純化 86 3.4 化合物之物理性質 89 參考文獻 92 附 圖 104 流程圖目錄 Scheme 1. Fractionation of the EtOH extract of Cordyceps militaris cultured in condition A (CM-A) 37 Scheme 2. Separation scheme of the n-BuOH-soluble fraction of the EtOH extract of CM-A 39 Scheme 3. Separation scheme of the CHCl3-soluble fraction of the EtOH extract of CM-A 41 Scheme 4. Fractionation of the EtOH extract of Cordyceps militaris cultured in condition B (CM-B) 42 Scheme 5. Separation scheme of the n-BuOH-soluble fraction of the EtOH extract of CM-B 43 Scheme 6. Separation scheme of the CHCl3-soluble fraction of the EtOH extract of CM-B 44 Scheme 7. Fractionation of the EtOH extract of Cordyceps militaris cultured in condition C (CM-C) 45 Scheme 8. Separation scheme of the n-BuOH-soluble fraction of the EtOH extract of CM-C 46 Scheme 9. Separation scheme of the CHCl3-soluble fraction of the EtOH extract of CM-C 46 Scheme 10. Fractionation of the EtOH extract of Andraca theae droppings 83 Scheme 11. Separation scheme of the EtOAc-soluble fraction of the EtOH extract of Andraca theae droppings 87 Scheme 12. Separation scheme of the EtOAc-soluble fraction of the EtOH extract of Andraca theae droppings 88 表目錄 Table 1. Contents of main chemical components in two wild and four cultured Cordyceps sp. 4 Table 2. Compounds isolated from Cordycps species 5 Table 3. 1H and 13C NMR data of 1 (methanol-d4, Bruker DPX-200) 20 Table 4. 1H and 13C NMR data of 4 (methanol-d4, Bruker DPX-200) 21 Table 5. 1H and 13C NMR data of 5 (DMSO-d6, Bruker AV-III 600) and 8 (methanol-d4, Bruker DPX-200) 24 Table 6. 1H and 13C NMR data of 6 and 7 (methanol-d4, Bruker DPX-200) 26 Table 7. 1H and 13C NMR data of 2 (DMSO-d6, Bruker AV-III 600). 28 Table 8. 1H and 13C NMR data of 3 (methanol-d4, Bruker DPX-200) 29 Table 9. 1H and 13C NMR data of 9 (CDCl3, Bruker AV-400) 31 Table 10. 1H and 13C NMR data of 10 (methanol-d4) 32 Table 11. Amount and percentage of compounds 5, 8, and 9 of three cultured conditions of C. militaris (CM-A-C) 34 Table 12. Compounds isolation from Camellia sinensis 50 Table 13. 1H and 13C NMR data of 11 (methanol-d4, Bruker AV-III 600). 63 Table 14. 1H and 13C NMR data of 12 (pyridine-d5, Bruker DPX-200 ), 13 and 15 (methanol-d4, Bruker DPX-200) 65 Table 15. 1H and 13C NMR data of compound 16 and 17 (methanol-d4, Bruker DPX-200) 67 Table 16. 1H and 13C NMR data of 20 and 21 (methanol-d4, Bruker DPX-200) 69 Table 17. 1H and 13C NMR data of 22, 23 and 24 (methanol-d4, Bruker DPX-200) 72 Table 18. 1H and 13C NMR data of 14 (methanol-d4, Bruker AV-400) 74 Table 19. 1H and 13C NMR data of 18 (methanol-d4, Bruker AV-400) 76 Table 20. 1H and 13C NMR data of 19 (methanol-d4, Bruker AV-400) 78 Table 21. The contants of compounds 14-24 in C. sinensis and A. theae droppings55,57,59,67,68 80 圖目錄 Figure 1. Fruiting bodies of Cordyceps militaris4 2 Figure 2. Structures of compounds 1-10 from Cordyceps militaris 19 Figure 3. Andraca sp.droppings.53,54 49 Figure 4 . Structures of compounds (11-24) from the droppings of Andraca theae 62 附圖目錄 (List of supporting figures) Figure S1. 1H NMR spectrum of compound 1 (CD3OD, 200 MHz). 109 Figure S2. 13C NMR spectra of compound 1 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 110 Figure S3. 1H NMR spectrum of compound 2 (DMSO-d6, 600 MHz). 111 Figure S4. 13C NMR spectra of compound 2 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (DMSO-d6, 150 MHz). 112 Figure S5. HMBC spectrum of compound 2 (DMSO-d6, 600 MHz). 113 Figure S6.HSQC spectrum of compound 2 (DMSO-d6, 600 MHz). 114 Figure S7. NOESY spectrum of compound 2 (DMSO-d6, 600 MHz). 115 Figure S8.COSY spectrum of compound 2 (DMSO-d6, 600 MHz). 116 Figure S9. 1H NMR spectrum of compound 3 (CD3OD, 200 MHz). 117 Figure S10. 13C NMR spectra of compound 3 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 118 Figure S11. 1H NMR spectrum of compound 4 (CD3OD, 200 MHz). 119 Figure S12. 13C NMR spectra of compound 4 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 120 Figure S13. 1H NMR spectrum of compound 5 (DMSO-d6, 600 MHz). 121 Figure S14. 13C NMR spectra of compound 5 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (DMSO-d6, 150 MHz). 122 Figure S15. COSY spectrum of compound 5 (DMSO-d6, 600 MHz). 123 Figure S16. 1H NMR spectrum of compound 6 (CD3OD, 200 MHz). 124 Figure S17. 13C NMR spectra of compound 6 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 125 Figure S18. 1H NMR spectrum of compound 7 (CD3OD, 200 MHz). 126 Figure S19. 13C NMR spectra of compound 7 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 127 Figure S20. 1H NMR spectrum of compound 8 (CD3OD, 200 MHz). 128 Figure S21. 13C NMR spectra of compound 8 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 129 Figure S22. 1H NMR spectrum of compound 9 (CD3OD, 400 MHz). 130 Figure S23. 13C NMR spectra of compound 9 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 100 MHz). 131 Figure S24. 1H NMR spectrum of compound 10 (CD3OD, 400 MHz). 132 Figure S25. 13C NMR spectra of compound 10 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 133 Figure S26. 1H NMR spectrum of compound 11 (DMSO-d6, 600 MHz). 134 Figure S27. 13C NMR spectra of compound 11 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (DMSO-d6, 150 MHz). 135 Figure S28. HMBC spectrum of compound 11 (DMSO-d6, 600 MHz). 136 Figure S29. 1H NMR spectrum of compound 12 (Pyridine-d5, 200 MHz). 137 Figure S30. 13C NMR spectra of compound 12 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz) 138 Figure S31. 1H NMR spectrum of compound 13 (CD3OD, 200 MHz). 139 Figure S32. 13C NMR spectra of compound 13 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz) 140 Figure S33. 1H NMR spectrum of compound 14 (CD3OD, 400 MHz). 141 Figure S34. 13C NMR spectra of compound 14 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 100 MHz) 142 Figure S35. 1H NMR spectrum of compound 15 (CD3OD, 200 MHz). 143 Figure S36. 13C NMR spectra of compound 15 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 144 Figure S37. 1H NMR spectrum of compound 16 (CD3OD, 200 MHz). 145 Figure S38. 13C NMR spectra of compound 16 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 146 Figure S39. 1H NMR spectrum of compound 17 (CD3OD, 200 MHz). 147 Figure S40. 13C NMR spectra of compound 17 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 148 Figure S41. 1H NMR spectrum of compound 18 (CD3OD, 400 MHz). 149 Figure S42. 13C NMR spectra of compound 18 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 100 MHz). 150 Figure S43. 1H NMR spectrum of compound 19 (CD3OD, 400 MHz). 151 Figure S44. 13C NMR spectra of compound 19 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 100 MHz). 152 Figure S45. 1H NMR spectrum of compound 20 (CD3OD, 200 MHz). 153 Figure S46. 13C NMR spectra of compound 20 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 154 Figure S47. 1H NMR spectrum of compound 21 (CD3OD, 200 MHz). 155 Figure S48. 13C NMR spectra of compound 21 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 156 Figure S49. 1H NMR spectrum of compound 22 (CD3OD, 200 MHz). 157 Figure S50.13C NMR spectra of compound 22 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 158 Figure S51. 1H NMR spectrum of compound 23 (CD3OD, 200 MHz). 159 Figure S52. 13C NMR spectra of compound 23 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 160 Figure S53. 1H NMR spectrum of compound 24 (CD3OD, 200 MHz). 161 Figure S54. 13C NMR spectra of compound 24 (BBD, bot.; DEPT-135, mid.; DEPT-90, top) (CD3OD, 50 MHz). 162 | |
dc.language.iso | zh-TW | |
dc.title | 北冬蟲夏草及茶蠶砂之化學成分分析研究 | zh_TW |
dc.title | Chemical investigation of Cordyceps militaris and Andraca theae droppings | en |
dc.type | Thesis | |
dc.date.schoolyear | 103-2 | |
dc.description.degree | 碩士 | |
dc.contributor.coadvisor | 李水盛 | |
dc.contributor.oralexamcommittee | 陳繼明 | |
dc.subject.keyword | 北蟲草,茶蠶砂, | zh_TW |
dc.subject.keyword | Cordyceps militaris,Andraca theae droppings, | en |
dc.relation.page | 162 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2015-07-23 | |
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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