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研究生:林憶珊
研究生(外文):Yi-Shan Lin
論文名稱:小西氏楠葉部成分、野薑花根莖成分及coronarin D衍生物製備之研究
論文名稱(外文):Chemical investigation of Machilus konishii leaves and Hedychium coronarium rhizomes and preparation of coronarin D derivatives
指導教授:李水盛
口試委員:沈雅敬張嘉銓徐鳳麟林雲蓮
口試日期:2014-07-04
學位類別:博士
校院名稱:國立臺灣大學
系所名稱:藥學研究所
學門:醫藥衛生學門
學類:藥學學類
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:290
中文關鍵詞:小西氏楠野薑花楨楠屬蝴蝶薑屬
外文關鍵詞:Machilus konishiiHeduchium coronariumcoronarin D
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本論文包括三個部分:
第一部分 小西氏楠葉部成分之研究
小西氏楠Machilus konishii (Hayata)為樟科楨楠屬的植物,中型至大型常綠喬木,為台灣特有,分佈於臺灣中南部中低海拔的闊葉林區。α-Glucosidase抑制劑為臨床上一類口服降血糖藥物,用於治療第二型糖尿病,主要作用為抑制碳水化合物在腸道的消化吸收。本研究以抑制α-glucosidase活性為導向,利用Sephadex LH-20管柱、離心分配層析、矽膠管柱、低壓逆相層析管柱以及半製備高壓液相層析管柱進行分離,自小西氏楠葉部乙醇萃取物分離並鑑定出二十九個化合物,分別屬於黃酮類(1, 7-25)、epicatechin聚合體類(2-6)、木脂素類(26-27)和酯類(28-29)。其中,化合物6為首次自天然物中分離得到,而化合物20、22、23及27為新化合物。活性測試結果顯示,化合物cinnamtannin B-1 (4)、kaempferol 3-O-(2-β-D-apiofuranosyl)-α-L-rhamnopyranoside (16)、tiliroside (24)和kaempferol 3-O-α-L-(2",4"-di-E-p-coumaroyl)-rhamnopyranoside (25)之IC50分別為24.2 μM、30.3 μM、18.3 μM和23.1 μM。

第二部分 野薑花之根莖部成分研究
野薑花Hedychium coronarium Koenig又稱為穗花山奈,為薑科蝴蝶薑屬的植物,分佈於印度、馬來西亞、越南、中國大陸南方和台灣,生長於低海拔的濕地。文獻報導其根莖部含有大量coronarin D,為具細胞毒性的雙&;#33820;類化合物,本研究擬分離大量此化合物,以供第三部分化學修飾研究用。野薑花根莖乙醇萃取物以極性劃分為氯仿、正丁醇和水可溶部分後,氯仿可溶部分進一步以乙&;#33096;和己烷進
行極性劃分成乙&;#33096;和己烷可溶部分,其中乙&;#33096;可溶部分以矽膠管柱分離可得到大量的coronarin D (30)成分。而正丁醇可溶部分則經Sephadex LH-20管柱、離心分配層析、矽膠管柱、低壓逆相層析管柱以及半製備高壓液相層析管柱進行分離,鑑定出十三個化合物,分別屬於diaryheptanoids (31-37)、芳香環配糖體(38-40)和核&;#33527;類(41-43),其中化合物31-37為新天然物,其結構係由光譜分析及化學反應而確定。
第三部分 Coronarin D衍生物之製備
本研究擬以coronarin D (30)作為起始物,以一系列反應,利用原有內脂環,開環再進一步重新形成七員環,合成12,13-dihydrogalanal A/B,或進一步胺基化形成胺基衍生物。針對exo-methylene修飾成羥甲基與提高反應性的步驟方面,嘗試了包括硼氫化-氧化反應、形成epoxide和與二氧化硒反應引入酮基等許多方法,可惜在產率方面都偏低,以致無法順利得到七員環之標的產物。然過程中一些較為成功的反應方法,仍可以作為未來繼續研究之碁石,包括以硫酸二甲酯/碳酸鉀進行甲基化反應,可針對內脂環進行開環形成methyl ester;以NiCl2‧6H2O和硼氫化鈉在甲醇中反應,產生(Ni2B)2H3,可選擇性還原Δ12位置上的共軛雙鍵,而不影響Δ8位置上的exo-methylene;以pyridinium chlorochromate作為氧化劑,可氧化15位置上屬於hemiacetal上的羥基,形成酸酐結構;以硼氫化鈉進行還原,再以濃硫酸和少量甲醇進行合環,兩階段反應可選擇性還原15位置上屬於hemiacetal上的羥基。


This dissertation includes three parts:
Part 1. Chemical investigation of the leaves of Machilus konishii
Machilus konishii Hayata (Lauraceae) is a medium-sized evergreen tree, endemically distributed in the broadleaved forests from low to medium altitudes in the central to southern parts of Taiwan. α-Glucosidase inhibitors, a class of orally administered hypoglycemic agents for type 2 diabetes, can decrease the absorption of carbohydrates from the intentine. Bioassay-guided fractionation against α-glucosidase has resulted in isolation and characterization of 29 compounds from the EtOH extract of the leaves of Machilus konishii by repeated chromatography on Sephadex LH-20, silica gel, Lobar RP-18, semipreparative HPLC, and centrifugal partition chromatography. These compounds were characterized as flavonoids (1, 7-25), epicatechin oligomers (2-6), lignans (26, 27), and esters (28, 29). Compound 6 is the first occurrence as natural product, and compounds 20, 22, 23 and 27 are new compounds. Cinnamtannin B-1 (4), kaempferol 3-O-(2-β-D-apiofuranosyl)-α-L-rhamnopyranoside (16), tiliroside (24), and kaempferol 3-O-α-L-(2",4"-di-E-p-coumaroyl)-rhamnopyranoside (25) showed moderate inhibitory activity against α-glucosidase with the IC50 values of 24.2 μM, 30.3 μM, 18.3 μM and 23.1 μM, respectively.
Part 2. Chemical investigation of Hedychium coronarium rhizome
Hedychium coronarium Koenig (Zingiberaceae) is a 1&;#8722;3 m tall herb, distributed in wetlands at low elevations of India, Malaysia, Vietnam, southern China, and Taiwan. Several cytotoxic compounds have been identified from the rhizome of this plant. To supply some of these active ingredients for chemical modification and to disclose polar constituents, the constituents of this part were reinvestigated. The EtOH extract were divided to fractions soluble in CHCl3, n-BuOH, and H2O. The CHCl3-soluble fraction was further partitioned into hexanes- and MeCN-soluble parts. The major component, coronarin D (30), was isolated from MeCN-soluble fraction by silica gel column chromatography and 13 compounds were isolated from n-BuOH -soluble fraction by repeated chromatography on Sephadex LH-20, silica gel, Lobar RP-18, semipreparative HPLC, and centrifugal partition chromatography. These compounds were characterized as diaryheptanoids (31-37), aromatic glycosides (38-40), and nucleosides (41-43). Of them, compounds 31-37 are new compounds. Their structures were established by spectroscopic analysis and chemical method.
Part 3. Preparation of coronarin D derivatives
The aim of this study is to prepare 12,13-dihydrogalanal A/B or their amine derivatives from coranarin D (30). After some attempts, our work was impeded by modification of exo-methylene to a hydroxymethyl group and failed to get cyclized target products. However, some successful methods could be helpful to the future study. Reaction with dimethyl sulfate/potassium carbonate could open the lactone ring besides forming methyl ester. Reaction with NiCl2‧6H2O and NaBH4 could selectively reduce the Δ12 conjugated doube bond without affectimg the exo-methylene (Δ8(17)). Oxidation of hemiacetal hydroxy group at C-15 with pyridinium chlorochromate could yield anhydride. Selective reduction of hemiacetal hydroxy group at C-15 could be achieved by NaBH4 and then cyclized by conc. H2SO4 in MeOH.


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…………………………………………………………………………………….VI
流程圖目錄 (List of schemes)………………………...………………………………..X
表目錄 (List of tables)…………………………………………………………….…..XI
圖目錄 (List of figures)………………………………………………………….…...XII
辭彙 (Glossary)……………………………………………………………….……..XIV
目錄
第一章:小西氏楠葉部成分之研究 1
壹、緒論及研究目的 1
1.1 研究目的 1
1.2小西氏楠植物簡介 2
1.3 樟科楨楠屬(Machilus)植物成分之文獻回顧 3
1.4 糖尿病與臨床治療藥物 14
1.4.1 糖尿病之盛行率與簡介 14
1.4.2 糖尿病治療藥物 14
1.4.3 α-Glucosidase inhibitors介紹 14
貳、實驗結果與討論 17
2.1 Epicatechin (1)與其寡聚物(2-5) 19
2.1.1 (&;#8722;)-Epicatechin (1)之結構解析 19
2.1.2 Procyanidin B-2 (2)、Procyanidin C-1 (3)、Cinnamtannin B-1 (4) 和Proanthocyanidin A-2 (5)之結構解析 20
2.1.3 Dehydrodiepicatechin A (6)之結構解析 25
2.2 黃酮類化合物(7-25) 28
2.2.1 Quercetin (7)及其配糖體(8-14)之結構解析 28
2.2.2 Kaempferol 3-O-β-D-galactopyranoside (15)及kaempferol 3-O-(2-β-D-apiofuranosyl)-α-L-rhamnopyranoside (16)之結構解析 32
2.2.3 Apigenin (17)及其配糖體(18-23)之結構解析 34
2.2.4 Tiliroside (24)及kaempferol 3-O-α-L-(2",4"-di-E-p-coumaroyl)- rhamnopyranoside (25)之結構解析 45
2.2.5 醣基部分光學活性之確認 47
2.3 木脂素化合物(26)和新木脂素化合物(27) 49
2.3.1 Isolariciresinol (26)之結構解析 49
2.3.2 Isolicarin B (27) 之結構解析 51
2.4 其他類化合物(28 and 29) 53
2.4.1 2,4,6-trihydroxybenzoic acid methyl ester (28)與 53
參、實驗部分 56
3.1 儀器與材料 56
3.1.1 理化性質測定儀器 56
3.1.2 成分分離之儀器及材料 56
3.1.3 試劑與溶媒 57
3.1.4 α-Glucosidase assay之試劑與儀器 58
3.1.5 糖分析之試劑與儀器 58
3.2 植物來源 59
3.3 小西氏楠葉部成分萃取與純化 59
3.3.1 正丁醇可溶部分之分離 59
3.3.2 乙酸乙酯可溶部分之分離 62
3.4 化合物之物理數據 67
3.5 α-Glucosidase抑制活性測試 (α-glucosidase inhibition assay) 72
3.5.1原理 72
3.5.2 實驗方法: 72
3.6 糖分析 75
3.6.1 酸水解 75
3.6.2 TMS衍生物之製備 75
3.6.3 GC分析 75
第二章: 野薑花根莖成分之研究 76
壹、緒論及研究目的 76
1.1 研究目的 76
1.2 野薑花植物簡介 77
1.3 薑科蝴蝶薑屬(Hedychium)植物之成分研究 79
貳、實驗結果與討論 87
2.1 Diterpene類(30) 89
2.2.1 Coronarin D (30)之結構解析 89
2.2 Diaryheptanoid類(31-37) 91
2.2.1 Hedycoropyran A (31)之結構解析 91
2.2.2 Hedycoropyran B (32)之結構解析 94
2.2.3 Hedycoropyran C (33)之結構解析 96
2.2.4 Hedycorofurans A-D (34-37)之結構解析 99
2.2.5 Hedycorofuran A-1,3-acetonide (34a)與 107
2.2.5 具四氫&;#21537;喃環與具四氫&;#21579;喃環之diarylheptanoid類化合物討論 109
2.3 芳香環配糖體類(38-40)之結構解析 112
2.4 核&;#33527;類(41-43) 116
2.4.1 Adenosine (41)、thymidine (42)和uridine (43)之結構解析 116
2.5 結論 118
參、實驗部分 119
3.1 儀器與材料 119
3.1.1 理化性質測定儀器 119
3.1.2 成分分離之儀器及材料 119
3.1.3 試劑與溶媒 120
3.2 植物來源 120
3.3 野薑花根莖部成分萃取與純化 120
3.3.1 Coronarin D (30)之分離 121
3.3.2 正丁醇可溶部分之分離 122
3.4 Acetonide衍生物之製備 126
3.4.1 Hedycorofuran A-1,3-acetonide (34a)之製備 126
3.4.2 Hedycorofuran D-2,3-acetonide (37a)之製備 126
3.5 化合物之物理數據 126
第三章: Coronarin D衍生物之製備 130
壹、緒論及研究目的 130
1.1 研究目的 130
貳、實驗結果與討論 131
2.1 實驗設計 131
2.2 化合物的合成 133
2.2.1 化合物I-IV的合成(Scheme 14) 133
2.2.2 化合物Va與Vb的合成(Scheme 15) 136
2.2.3 化合物VI與VII的合成(Schemes 16-17) 138
2.2.4 化合物VIII的合成(Scheme 18) 139
2.2.5 化合物IXa-IXc的合成(Scheme 19) 139
2.2.6 化合物X-XII的合成(Scheme 20) 141
2.2.7 化合物XIII-XVI的合成(Scheme 22) 142
2.2.8 化合物IXb, XVII-XX的合成(Schemes 23-24) 144
2.2.9 Hydroboration model study:末端雙鍵氧化形成醇基之反應(Scheme 25) 146
2.3 結論 147
參、實驗部分 148
3.1 儀器與材料 148
3.1.1 理化性質測定儀器 148
3.1.2 成分分離之儀器及材料 148
3.1.3 試劑與溶媒 148
3.2 Coronarin D衍生物之製備與物理數據 150
3.2.1 化合物I-IV之製備(Scheme 14) 150
3.2.2 化合物Va與Vb之製備(Scheme 15) 152
3.2.3 化合物VI之製備(Scheme 16) 153
3.2.4 化合物VII之製備(Scheme 17) 154
3.2.5 化合物VIII之製備(Scheme 18) 154
3.2.6 化合物IXa-IXc之製備(Schemes 19, 23 &; 24) 155
3.2.7 化合物X-XII之製備(Scheme 20) 157
3.2.8 化合物XIII-XVI之製備(Scheme 22) 159
3.2.9 化合物XVII-XX之製備(Scheme 24) 163
3.2.10 化合物L2之製備(Scheme 25) 166
參考文獻 167
附圖 178

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