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研究生:廖宇仁
研究生(外文):Yu-RenLiao
論文名稱:I.小葉桑之成分與生物活性研究II.Benzocamphorin衍生物之合成研究
論文名稱(外文):I.Studies on the Constituents and Biological Activities of Morus australis Poir.II.Synthesis of Benzocamphorin and its Derivatives.
指導教授:吳天賞吳天賞引用關係
指導教授(外文):Tian-Shung Wu
學位類別:博士
校院名稱:國立成功大學
系所名稱:化學系碩博士班
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2012
畢業學年度:100
語文別:中文
論文頁數:254
中文關鍵詞:小葉桑牛樟芝Sonogashira反應抗血小凝集反應抗發炎反應
外文關鍵詞:Morus australis PoirTaiwanofungus camphoratusanti-platelet aggregationanti-inflammatorySonogashira reaction
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從小葉桑部分離得到40個化合物,經光譜分析與化學方法鑑定確認其結構,分別為: atalantoflavone (299)、morusin (11)、oxydihydromorusin (25)、cyclomorusin A (19)、neocyclomorusin (132)、artocommunols CD (300)、2-(2,4-diacetoxy-phenyl)-5-hydroxy-8,8-dimethyl-3-(3-methyl-but-2-enyl)
-8H-pyrano[2,3-f]chromen-4-one (301)、orobol (302)、morustralin A (303)、morustralin B (304)、(Z)-1-hydroxy-4-(2-nitroethenyl)benzene (305)、moracin B (192)、ergosterol (306)、ergosta-4, 6, 8 (14), 22-tetraen-3-one (307)、ursolic acid (308)、norartocarpetin (309)、kuwanon C (310)、morusinol (311)、moracin P (312)、7-Hydroxycoumarin (313)、Scopoletin (314)、Vanillic acid (315)、Syringic acid (316)、Methyl syringate (317)、p-Hydroxybenzaldehyde (318)、Vanillin (319)、Syringaldehyde (320)、4-Hydroxy-3-methoxycinnamic acid (321)、angustifolin (322)、 toddanin (323)、Methyl gallate (324)、Gallic acid (325)、4-Hydroxycinnamic acid (326)、3-(5,6-dimethoxybenzofuran-2-yl)-5-methoxyphenol (327)、unknown(328)、unknown(329)。其中有2個為首次分離得到之化合物,分別為morustralin A (303)、morustralin B (304),以及1個天然界首次分離得到之化合物為(Z)-1-hydroxy-4-(2-nitroethenyl)benzene (305)。抗血小板凝集生物活性測試中,在ADP的抑制活性 (IC50 )表現上,尤以化合物305 ( IC50 = 9.67μM )及化合物301 ( IC50 = 10.15μM ) 具有更顯著的抑制效果。以及在AA的抑制活性表現上,化合物305 ( IC50 = 9.81μM )具有非常顯著的抑制效果。抗發炎作用生物活性測試中,可以發現化合物311 (IC50 =4.1μg/mL)、305 (IC50 =2.1μg/mL)、19 (IC50 =4.5μg/mL)、328 (IC50 =8.2μg/mL )、132 (IC50 =6.3μg/mL )、301 (IC50 =2.4μg/mL )及25 (IC50 =4.6μg/mL)具有相當的開發藥物的潛力。

Benzocamphorin H (336)、F(351) 從牛樟芝(Taiwanofungus camphoratus)植物中分離純化所分離出的具有抗發炎活性的成分,本研究利用Sonogashira反應成功的合成出具有三鍵化合物的單苯環類(benzenoids)骨架化合物,且針對合成出的化合物Benzocamphorin H (336)、F(351)進一步做抗發炎活性的評估,顯示化合物336及351對於NADPH氧化酶(NOX)及一氧化氮合成酶(nitric oxide synthase,NOS)都有濃度相關(concentration-dependent)之抑制作用,其半數抑制濃度IC50 分別為15.09及8.6 μM,但與NOX抑制劑(diphenyleneiodonium,DPI)及NOS抑制劑(L-NAME)做對照後,發現化合物351抑制活性明顯強於NOS抑制劑(L-NAME)。

Forty compounds were isolated from the stems of Morus australis Poir. and were characterized by comprehensive analyses of their 1D, 2D-NMR and mass spectral data, and also by chemical transformation studies. Two new compounds were characterized as morustralin A (303)、morustralin B (304) by spectroscopic analyses. One compound was (Z)-1-hydroxy-4-(2-nitroethenyl)benzene (305) which were reported for the first time from natural sources. On the other hand, thirty- seven known compounds were identified as atalantoflavone (299)、morusin (11)、oxydihydromorusin (25)、cyclomorusin A (19)、neocyclomorusin (132)、artocommunols CD (300)、2-(2,4-diacetoxy-phenyl)-5-hydroxy-8,8-dimethyl-3-(3-methyl-but-2-enyl)-8H-pyrano[2,3-f]chromen-4-one (301)、orobol (302)、 moracin B (192)、ergosterol (306)、ergosta-4, 6, 8 (14), 22-tetraen-3-one (307)、ursolic acid (308)、norartocarpetin (309)、kuwanon C (310)、morusinol (311)、moracin P (312)、7-Hydroxycoumarin (313)、Scopoletin (314)、Vanillic acid (315)、Syringic acid (316)、Methyl syringate (317)、p-Hydroxybenzaldehyde (318)、Vanillin (319)、Syringaldehyde (320)、4-Hydroxy-3-methoxycinnamic acid (321)、angustifolin (322)、 toddanin (323)、Methyl gallate (324)、Gallic acid (325)、4-Hydroxycinnamic acid (326)、3-(5,6-dimethoxybenzofuran-2-yl)-5-methoxyphenol (327)、unknown(328)、unknown(329)。The structures of the isolated compounds were elucidated by 1H-, 13C-, 2D-NMR, MS, UV and IR spectral analyses and the comparison of spectroscopic data with those reported in the literatures. The bioactive assay of the isolated compounds including anti-platelet aggregation and anti-inflammatory effects exhibited potent anti-platelet aggregation bioactivity.

A naturally occurring enynyl-benzenoid, benzocamphorin F(351)、H(336), from the edible fungus Taiwanofungus camphoratus (Antrodia camphorata) was characterized by the comprehensive spectral analysis. It displayed anti-inflammatory bioactivity and would be valuable for further biological studies. The present study is the first total synthesis (by Sonogashira reaction) of benzocamphorin F、H and the developed strategy described a more efficient procedure that allowed large-scale production of benzocamphorin F for the further research of biological activity (anti-inflammatory) both in vitro and in vivo.

目 錄

英文摘要………………………………………………………………………………….I
中文摘要……………………………………………………………………………….III
第一章 緒論…………………………………………………………………..……..1
第二章 桑屬植物研究之回顧..………………..……………………….……...3
第一節 小葉桑之植物形態…………………………………….…………..3
第二節 桑屬(Morus)植物之藥理研究回顧…………………………...4
第三節 桑屬(Morus)植物之成分研究回顧……………….…………..18
第四節 小葉桑之成分抽取與分離…………………………………….………59
第三章 小葉桑成分之化學構造研究及藥理試驗……………………………..63
第一節 Atalantoflavone(299)之構造研究………………….……….65
第二節 Morusin(11)之構造研究…………………………………….....71
第三節 Oxydihydromorusin(25)之構造研究………………….……….77
第四節 Cyclomorusin A(19)之構造研究………………….….………84
第五節 Neocyclomorusin(132)之構造研究……………………….………92
第六節 Artocommunols CD(300)之構造研究…………………….………101
第七節 2-(2,4-diacetoxy-phenyl)-5-hydroxy-8,8-dimethyl-3-(3-methyl-but-2-enyl)-8H-pyrano[2,3-f]chromen-4-one (301)(171)之構造研究..…….……...108
第八節 Orobol (302)之構造研究…………………………..….……...116
第九節 Morustralin A (303)之構造研究………………………….………119
第十節 Morustralin B (304)之構造研究…………………….……...130
第十一節 (Z)-1-hydroxy-4-(2-nitroethenyl)benzene (305)之構造研究.……...….137
第十二節 Moracin B (192)之構造研究…………………....….……...145
第十三節 Ergosterol (306)之構造研究…………………………………...150
第十四節 Ergosta-4, 6, 8 (14), 22-tetraen-3-one (307)之構造研究…….….…….153
第十五節 ursolic acid (308)之構造決定…………………………………..156
第十六節 其他化合物之構造決定…………………………………...….…...159
第十七節 小葉桑成分之抗血小板凝集之活性試驗………………………….160
第十八節 小葉桑成分之抗發炎作用機制與生理活性探討…………………...162
第四章 牛樟芝衍生物之全合成研究及藥效評估……………………..……167
第一節 牛樟芝之形態介紹……………………………….………….……167
第二節 發炎反應…………………..……………………………….……………168
第三節 Benzocamphorin系列之相關生理活性概況及研究動機……………………………………………………….……..170
第四節 Sonogashira 反應的起源與發展………………………….….….173
第五節 Benzocamphorin H(336) 之合成途徑探討……………………….178
第六節 Benzocamphorin F (351) 之合成途徑探討……………………181
第七節 Benzocamphorin衍生物 (355 ~360) 之合成探討……………183
第八節 抗發炎作用機制與生理活性探討……………………………….…184
第五章 結論……………………………………….………………………...187
第六章 實驗部分……………………………………………………...….………189
第一節 本實驗所使用之儀器與藥品……………………………..…………….189
第二節 小葉桑的採集及鑑定………………………………………….….…….191
第三節 小葉桑成分之萃取與分離……………………………….….…….…192
第四節 Benzocamphorin H(336)全合成研究之實驗步驟……….….…195
第五節 血小板凝集檢測試驗步驟......197
第六節 彈性蛋白酶釋放及超氧化物檢測試驗步驟....198
第七節 產生NO之抑制活性試驗檢測步驟.......199
第七章 光譜數據……………………………………..……….…...200
第一節 小葉桑所分離得到成分之光譜數據……………………...........200
第二節 牛樟芝衍生物全合成研究之光譜數據…………………………….223
參考文獻…………………………………………………………………………….234

圖 目 錄

圖1 小葉桑植物之外觀圖……………………………………………………………….3
圖2 小葉桑植物之外觀繪圖…………………………………………………………….3
圖3 小葉桑之成熟果實外觀圖…………………………………...……………………..3
圖4 小葉桑各分配層之分離流程………………………………………….…………..60
圖5 黃酮類類化合物的母核結構……………………………………………………..63
圖6 化合物(299)之1H NMR光譜……………………………………………………..67
圖7 化合物(299)之1H NMR光譜……………………………………………………..67
圖8 化合物(299)之13C NMR光譜…………………………………………………….68
圖9 化合物(299)之HSQC光譜……………………………………………………..68
圖10 化合物(299)之HMBC光譜……………………………………………………..79
圖11 化合物(299)之HMBC光譜……………………………………………………..79
圖12 化合物(299)之COSY光譜……………………………………………………..70
圖13 化合物(11)之1H NMR光譜……………………………………………………..73
圖14 化合物(11)之13C NMR光譜…………………………………………………..73
圖15 化合物(11)之dept-135 NMR光譜………………….…………………………..74
圖16 化合物(11)之HSQC光譜……………………………………………………....74
圖17 化合物(11)之HMBC光譜……………………………………………………...75
圖18 化合物(11)之COSY光譜………………………………………………………76
圖19 化合物(25)之1H NMR光譜……………………………………………….….79
圖20 化合物(25)之13C NMR光譜……………………………………………..……..79
圖21 化合物(25)之HSQC譜……………………………………………….……..80
圖22 化合物(25)之HSQC光譜…….……………………………………………….80
圖23 化合物(25)之HMBC光譜…………………………………………………..81
圖24 化合物(25)之HMBC光譜…………………………………………………..82
圖25 化合物(25)之COSY光譜…………………………………………….………..83
圖26 化合物(19)之1H NMR光譜……………………………………………………..86
圖27 化合物(19)之13C NMR光譜…………………………………………………..86圖28 化合物(19)之13C NMR光譜…………………………………………………..87圖29 化合物(19)之13C NMR光譜…………………………………………………..87
圖30 化合物(19)之HSQC光譜…………………………………………………….88
圖31 化合物(19)之HSQC光譜……………………………………………….……..88
圖32 化合物(19)之HMBC光譜…………………………………………………….89
圖33 化合物(19)之HMBC光譜……………………………………………………..90
圖34 化合物(19)之HMBC光譜…………………………………………………..90
圖35 化合物(19)之COSY光譜…………………………………………….………..91
圖36 化合物(19)之NOESY光譜…………………………………………………….91
圖37 化合物(132)之1H NMR光譜………………………………………………….94
圖38 化合物(132)之1H NMR光譜………………………………………………….94
圖39 化合物(132)之13C NMR光譜…………………………………………….……95
圖40 化合物(132)之13C NMR光譜…………………………………………………95
圖41 化合物(132)之dept-135 NMR光譜……………………………………………..96
圖42 化合物(132)之HSQC光譜…………………………………………………..96
圖43 化合物(132)之HSQC光譜…………………………………………….………..97
圖44 化合物(132)之HSQC光譜……………………………………………………..97
圖45 化合物(132)之HMBC光譜……………………………………………………..98
圖46 化合物(132)之HMBC光譜……………………………………………………...98圖47 化合物(132)之HMBC譜……………………………………………….……..99
圖48 化合物(132)之HMBC光譜…………………….…………………………….99
圖49 化合物(300)之1H NMR光譜…………………………………………………..100
圖50 化合物(300)之13C NMR光譜……………………………………………….104
圖51 化合物(169)之HMQC光譜…………………………………………….…….105
圖52 化合物(169)之HMBC光譜………………………………………………….106
圖53 化合物(169)之COSY光譜……………………………………………………..107
圖54 化合物(301)之1H NMR光譜…………………………………………………108
圖55 化合物(301)之1H NMR譜……………..………………………………….…110
圖56 化合物(301)之13C NMR光譜………………….……………………………110
圖57 化合物(301)之HSQC光譜………………………………………………111
圖58 化合物(301)之HSQC光譜……………………………………………111
圖59 化合物(301)之HSQC光譜……..…………………………………….…112
圖60 化合物(301)之HMBC光譜……………………………………………113
圖61 化合物(301)之HMBC光譜……..………………………………………114
圖62 化合物(301)之HMBC光譜………..……………………………………114
圖63 化合物(301)之COSY譜……………..………………………………….115
圖64 化合物(302)之1H NMR光譜……………….……………………………117
圖65 化合物(302)之13C NMR光譜…………………………………………118
圖66 化合物(303)之EI-MS光譜………………………………………………122
圖67 化合物(303)之IR光譜……..…………………………………….…122
圖68 化合物(303)之CD光譜……………………………………………123
圖69 化合物(303)之1H NMR光譜……..…………………………………………123
圖70 化合物(303)之13C NMR光譜………..………………………………………124
圖71 化合物(303)之dept-135 NMR譜…………….…………………………….…124
圖72 化合物(303)之HSQC光譜………………….…………………………125
圖73 化合物(303)之HSQC光譜………………………………………………126
圖74 化合物(303)之HSQC光譜………………………………………………126
圖75 化合物(303)之HMBC光譜……..…………………………………….……127
圖76 化合物(303)之HMBC光譜………………………………………………128
圖77 化合物(303)之COSY光譜……..……………………………………………129
圖78 化合物(304)之EI-MS光譜………..………………………………………132
圖79 化合物(304)之IR光譜…………..………………………………….…132
圖80 化合物(304)之1H NMR光譜……………….….……………………………133
圖81 化合物(304)之13C NMR光譜………………………………………………133
圖82 化合物(304)之HSQC光譜………………………………………………134
圖83 化合物(304)之HSQC光譜……..…………………………………….……134
圖84 化合物(304)之HMBC光譜………………………………………………135
圖85 化合物(305)之1H NMR光譜……..…………………………………………139
圖86 化合物(305)之1H NMR光譜………..………………………………………139
圖87 化合物(305)之13C NMR譜…………..………………………………….…140
圖88 化合物(305)之HSQC光譜………….……….……………………………140
圖89 化合物(305)之HSQC光譜………………………………………………141
圖90 化合物(305)之HMBC光譜…………………………………………………141
圖91 化合物(305)之HMBC光譜……..…………………………………….……142
圖92 化合物(305)之COSY光譜………………………………………………143
圖93 化合物(305)之IR光譜……..…………………………………………144
圖94 化合物(192)之1H NMR光譜………..………………………………………147
圖95 化合物(192)之13C NMR 譜…………..………………………………….…147
圖96 化合物(192)之HSQC光譜……………….…….……………………………148
圖97 化合物(192)之HMBC光譜………………………………………………148
圖98 化合物(192)之NOESY光譜………………………………………………149
圖99 化合物(306)之1H NMR光譜……..…………………………………….……152
圖100 化合物(306)之13C NMR光譜………………………………………………152
圖101 化合物(307)之1H NMR光譜……..…………………………………………155
圖102 化合物(307)之13C NMR光譜………..…………………………………155
圖103 化合物(308)之IR譜…………..………………………………….…157
圖104 化合物(308)之1H NMR光譜……………….……….……………………157
圖105 化合物(308)之13C NMR光譜………………………………………………158
圖106 化合物Antrocamphin A(337)…………………………………………………..170
圖107 Antrocamphin A合成路徑…………..………………………………….……..171
圖108 Benzocamphorin H化合物的逆向合成拆解(retrosynthesis)………………..172
圖109 Benzocamphorin F化合物的逆向合成拆解(retrosynthesis)…………………172
圖110 Sonogashira Cross-Coupling 反應機制……………………….………………173




















表 目 錄

表1 桑屬植物迄今所報導之化學成分………………………………………..….18
表2 抑制血小板凝集活性………………………………………..……….…….160
表3 小葉桑萃取物抑制血小板凝集之活性………………………………………161
表4 小葉桑成分抑制NO活性試驗結果………………………………………..163
表5 化合物336及351對NOS、NADPH (NOX) 及DPPH 生物活性測試………184
表6 化合物354-359對超氧自由基陰離子的抗發炎活性試驗……………………..185
表7 化合物354-359對彈性蛋白酶的抗發炎活性試驗………………………..….…186


參考文獻

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