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研究生:余俊賢
研究生(外文):Jin-Hsien Yu
論文名稱:恆春哥納香葉部化學成分及其細胞毒性之研究
論文名稱(外文):Chemical Constituents and Cytotoxicity of the Leaves of Goniothalamus amuyon
指導教授:吳永昌
指導教授(外文):Yang-Chang Wu
學位類別:碩士
校院名稱:高雄醫學大學
系所名稱:天然藥物研究所
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:2001
畢業學年度:89
語文別:中文
論文頁數:151
中文關鍵詞:恆春哥納香化學成分細胞毒性
外文關鍵詞:Goniothalamus amuyonChemical ConstituentsCytotoxicity
相關次數:
  • 被引用被引用:2
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中文摘要
從恆春哥納香(Goniothalamus amuyon)之葉部共分離純化得到二十個化合物,包含:十一個styrylpyrone骨架化合物,(6R,7R,8R)-goniodiol (1)、(6R,7S,8S)-goniodiol (2)、(6R,7R,8R)-goniodiol-7mono acetate (3)、(6R,7R,8R)-goniodiol-8-monoacetate (4)、(6R,7S,8S)-7-me thoxygoniodiol (5)、(5S,6R,7R,8R)-goniotriol (6)、(5S,6R,7S,8S)-goniotriol (7)、(5S,6R,7R,8R)-5-methoxygoniotriol (8)、goniothalamin (9)、goniothalamin epoxide (10)與 (+)-5-deoxygonio-pypyrone (11);四個alkaloid類的化合物,piperlactam C (12)、aristolactam FII (13)、liriodenine (14)與lysicamine (15);一個lignan類化合物,(+)-pinoresinol (16);兩個aromatic類化合物,veratic acid (17)與cinnamic acid (18),及兩個steroids類的化合物,b-sitosterol (19)與stigmasterol (20)之混合物。
上列二十個化合物的結構解析經由光譜資料分析、配合化學方法及各種衍生物的製備加以證明確定。其中,化合物2、5、7、8均為文獻未發表過之新化合物。化合物10、11、12、17與18 為本植物首次分離得到。在細胞毒殺作用研究方面,所分離得到styrylpyrone,結果顯示化合物2、3、4與10對於人類胃癌細胞 NUGC與鼻咽癌細胞HONE-1均有不錯的抑制活性。濃度於10 mM 對於人類胃癌細胞 NUGC之活性接近99 % 抑制活性。而化合物7濃度於50 mM對於人類胃癌細胞NUGC與鼻咽癌細胞HONE-1抑制活性接近30 %抑制活性。
Abstract
Twenty compounds including eleven styrylpyrones (6R,7R,8R)-goniodiol (1), (6R,7S,8S)-goniodiol (2), (6R,7R,8R)-goniodiol-7-mono-acetate (3),(6R,7R,8R)-goniodiol-8-monoacetate (4), (6R,7S,8S)-8-meth-oxygoniodiol (5), (5S,6R,7R,8R)-goniotriol (6), (5S,6R,7S,8S)-goniotriol (7), (5S, 6R, 7R, 8R)-7-methoxygoniotriol (8), goniothalamin (9), goniothalamin epoxide (10), and (+)-5-deoxy-goniopypyrone (11), four alkaloids, piperlactam C (12), aristolactam FII (13), liriodenine (14), and lysicamine (15), one lignan, (+)-pinoresinol (16), two aromatic compounds, veratic acid (17) and cinnamic acid (18), and two steroids, b-sitosterol (19) and stigmasterol (20), have been isolated from the leaves of Goniothalamus amuyon.
All isolates were characterized by spectral and chemical analysis. Among them, 2, 5, 7, and 8 are new compounds, compounds 10, 11, 12, 17, and 18 are isolated form this species for the first time.
Compounds 2, 3, 4, and 10 exhibited ca. 99 % inhibition against NUGC and HONE-1 cell lines at a concentration of 10 mM, compound 7 exhibited 30 % inhibition against NUGC and HONE-1 cell line at a concentration of 50mM.
目 錄
謝辭----------------------------------------------------------------------------------I
中文摘要---------------------------------------------------------------------------II
英文摘要------------------------------------------------------------------------- IV
第一章 緒論
第二章
第一節前言------------------------------------------------------------1
第二節植物分佈及形態--------------------------------------------14
第三節研究目的-----------------------------------------------------17
第三章 恆春哥納香葉部成分之抽取及分離------------------------------18
第四章 化合物之結構證明
第一節 (6R,7R,8R)-Goniodiol (1)之結構證明--------------------- 21
第二節 (6R,7S,8S)-Goniodiol (2)之結構證明----------------------28
第三節 Goniodiol-7-monoacetate (3)之結構證明-----------------34
第四節 Goniodiol-8-monoacetate (4)之結構證明-----------------39
第五節 (6R,7S,8S)-7-Methoxygoniodiol (5)之結構證------------44
第六節 (5S,6R,7R,8R)-Goniotiol (6)之結構證明------------------ 31
第七節 (5S,6R,7S,8S)-Goniotriol (7)之結構證明------------------58
第八節 (5S,6R,7R,8R)- 7-Methoxygoniotiol (8)之結構證明-----65
第九節 Goniothalamin (9)之結構證明------------------------------72
第十節 Goniothalamin epoxide (10)之結構證明------------------78
第十一節 (+)-5-deoxygoniopypyrone (11)之結構證明-----------83
第十二節 Piperlactam C (12)之結構證明--------------------------88
第十三節 Aristolactam FII (13)之結構證明------------------------92
第十四節 Liriodenine (14)之結構證明------------------------------96
第十五節 Lysicamine (15)之結構證明----------------------------101
第十六節 (+)-Pinoresinol (16)之結構證明------------------------104
第十七節 Veratic acid (17)之結構證明----------------------------108
第十八節 Cinnamic acid (18)之結構證明-------------------------111
第十九節 b-sitosterol (19) & stigamsterol (20)之結構證明----115
第五章生物活性試驗--------------------------------------------------------120
第六章相關實驗部份
第一節 儀器與材料---------------------------------------------------123
第二節 植物材料與分離純化---------------------------------------125
第三節 各化合物之光譜數據---------------------------------------127
第七章 結論--------------------------------------------------------------------141
第八章 參考文獻--------------------------------------------------------------142
圖 表 目 錄
圖一、恆春哥納香之外觀------------------------------------------------------32
圖二、恆春哥納香之葉部之分離流程---------------------------------------40
圖三、Styrylpyrones之生合成-----------------------------------------------161
圖四、Styrylpyrones立體決定與erythro & threo之關係-----------------162
圖五、Styrylpyrones立體決定與erythro & threo之關係-----------------163
圖六、Styrylpyrones之細胞毒殺機轉--------------------------------------164
圖1-1、(6R,7R,8R)-Goniodiol (1)之IR吸收光譜圖------------------------24
圖1-2、(6R,7R,8R)-Goniodiol (1)之1H-NMR光譜圖----------------------24
圖1-3、(6R,7R,8R)-Goniodiol (1)之13C-NMR光譜圖---------------------25
圖1-4、(6R,7R,8R)-Goniodiol (1)之DEPT光譜圖-------------------------25
圖1-5、(6R,7R,8R)-Goniodiol (1)之NOESY光譜圖-----------------------26
圖1-6、(6R,7R,8R)-Goniodiol (1)之COSY光譜圖-------------------------26
圖1-7、(6R,7R,8R)-Goniodiol (1)之HETCOR光譜圖---------------------27
圖1-8、(6R,7R,8R)-Goniodiol (1)之EIMS質譜圖--------------------------27
圖2-1、(6R,7S,8S )-Goniodiol (2)之IR吸收光譜圖------------------------31
圖2-2、(6R,7S,8S )-Goniodiol (2)之1H-NMR光譜圖----------------------31
圖2-3、(6R,7S,8S )-Goniodiol (2)之13C-NMR光譜圖---------------------32
圖2-4、(6R,7S,8S )-Goniodiol (2)之DEPT光譜圖-------------------------32
圖2-5、(6R,7S,8S )-Goniodiol (2)之NOESY光譜圖-----------------------33
圖2-6、(6R,7S,8S )-Goniodiol (2)之EIMS質譜圖--------------------------33
圖3-1、(6R,7R,8R)-Goniodiol-7-monoacetate (3)之IR吸收光譜圖-----37
圖3-2、(6R,7R,8R)-Goniodiol-7-monoacetate (3)之1H-NMR光譜圖---37
圖3-3、(6R,7R,8R)-Goniodiol-7-monoacetate (3)之EIMS質譜圖-------38
圖4-1、(6R,7R,8R)-Goniodiol-8-monoacetate (4)之IR吸收光譜圖-----42
圖4-2、(6R,7R,8R)-Goniodiol-8-monoacetate (4)之1H-NMR光譜圖---42
圖4-3、(6R,7R,8R)-Goniodiol-8-monoacetate (4)之EIMS質譜圖-------43
圖5-1、(5S,6R,7R,8R)-7-Methoxygoniodiol (5)之IR吸收光譜圖--------47
圖5-2、(5S,6R,7R,8R)-7-Methoxygoniodiol (5)之1H-NMR光譜圖------47
圖5-3、(5S,6R,7R,8R)-7-Methoxygoniodiol (5)之13C-NMR光譜圖-----48
圖5-4、(5S,6R,7R,8R)-7-Methoxygoniodiol (5)之NOESY光譜圖-------48
圖5-5、(5S,6R,7R,8R)-7-Methoxygoniodiol (5)之COSY光譜圖---------49
圖5-6、(5S,6R,7R,8R)-7-Methoxygoniodiol (5)之HETCOR光譜圖-----49圖5-7、(5S,6R,7R,8R)-7-Methoxygoniodiol(5)之EIMS質譜圖----------50圖6-1、(5S,6R,7R,8R)-Goniotriol (6)之IR吸收光譜圖--------------------54
圖6-2、(5S,6R,7R,8R)-Goniotriol (6)之1H-NMR光譜圖------------------54
圖6-3、(5S,6R,7R,8R)-Goniotriol (6)之13C-NMR光譜圖-----------------55
圖6-4、(5S,6R,7R,8R)-Goniotriol (6)之DEPT光譜圖---------------------55
圖6-5、(5S,6R,7R,8R)-Goniotriol (6)之NOESY光譜圖-------------------56
圖6-6、(5S,6R,7R,8R)-Goniotriol (6)之COSY光譜圖---------------------56
圖6-7、(5S,6R,7R,8R)-Goniotriol (6)之EIMS質譜圖----------------------57
圖7-1、(5S,6R,7S,8S)-Goniotriol (7)之IR吸收光譜圖---------------------61
圖7-2、(5S,6R,7S,8S)-Goniotriol (7)之1H-NMR光譜圖-------------------61
圖7-3、(5S,6R,7S,8S)-Goniotriol (7)之13C-NMR光譜圖------------------62
圖7-4、(5S,6R,7S,8S)-Goniotriol (7)之DEPT光譜圖----------------------62
圖7-5、(5S,6R,7S,8S)-Goniotriol (7)之NOESY光譜圖--------------------63
圖7-6、(5S,6R,7S,8S)-Goniotriol (7)之COSY光譜圖----------------------63
圖7-7、(5S,6R,7S,8S)-Goniotriol (7)之HETCOR光譜圖------------------64
圖7-8、(5S,6R,7S,8S)-Goniotriol (7)之EIMS質譜圖----------------------64
圖8-1、(5S,6R,7R,8R)-5-Methoxygoniotriol (8)之IR吸收光譜圖-------68
圖8-2、(5S,6R,7R,8R)-5-Methoxygoniotriol (8)之1H-NMR光譜圖-----68
圖8-3、(5S,6R,7R,8R)-5-Methoxygoniotriol (8)之13C-NMR光譜圖----69
圖8-4、(5S,6R,7R,8R)-5-Methoxygoniotriol (8)之NOESY光譜圖------69
圖8-5、(5S,6R,7R,8R)-5-Methoxygoniotriol (8)之COSY光譜圖--------70
圖8-6、(5S,6R,7R,8R)-5-Methoxygoniotriol (8)之HMQC光譜圖-------70
圖8-7、(5S,6R,7R,8R)-5-Methoxygoniotriol (8)之EIMS質譜圖---------71
圖9-1、Goniothalamin (9)之IR吸收光譜圖---------------------------------75
圖9-2、Goniothalamin (9)之1H-NMR光譜圖-------------------------------75
圖9-3、Goniothalamin (9)之13C-NMR光譜圖------------------------------76
圖9-4、Goniothalamin (9)之 DEPT光譜圖---------------------------------76
圖9-5、Goniothalamin (9)之EIMS質譜圖----------------------------------77
圖10-1、Goniothalamin epoxide (10)之IR吸收光譜圖-------------------81
圖10-2、Goniothalamin epoxide (10)之1H-NMR光譜圖-----------------81
圖10-3、Goniothalamin epoxide (10)之 13C-NMR光譜圖----------------82
圖10-4、Goniothalamin epoxide (10)之EIMS質譜圖---------------------82
圖11-1、(+)-5-Deoxygoniopypyrone (11)之IR吸收光譜圖---------------86
圖11-2、(+)-5-Deoxygoniopypyrone (11)之1H-NMR光譜圖-------------86
圖11-3、(+)-5-Deoxygoniopypyrone (11)之 13C-NMR光譜圖-----------87
圖11-4、(+)-5-Deoxygoniopypyrone (11)之EIMS質譜圖----------------90
圖12-1、Piperlactam C (12)之IR吸收光譜圖-------------------------------90
圖12-2、Piperlactam C (12)之1H-NMR光譜圖-----------------------------91
圖12-3、Piperlactam C (12)之EIMS質譜圖--------------------------------93
圖13-1、Aristolactam FII(13)之IR吸收光譜圖----------------------------94
圖13-2、Aristolactam FII(13)之1H-NMR光譜圖---------------------------94
圖13-3、Aristolactam FII(13)之EIMS質譜圖------------------------------95
圖14-1、Liriodenine (14)之IR吸收光譜圖----------------------------------99
圖14-2、Liriodenine (14)之1H-NMR光譜圖--------------------------------99
圖14-3、Lysicamine (15)之EIMS質譜圖----------------------------------100
圖15-1、Lysicamine (15)之IR吸收光譜圖--------------------------------103
圖15-2、Lysicamine (15)之1H-NMR光譜圖------------------------------103
圖16-1、(+)-Pinoresinol (16)之1H-NMR光譜圖--------------------------106
圖16-2、(+)-Pinoresinol (16)之13C-NMR光譜圖-------------------------106圖16-3、(+)-Pinoresinol (16)之EIMS質譜圖------------------------------107
圖17-1、Veratic acid (17)之IR吸收光譜圖--------------------------------110
圖17-2、Veratic acid (17)之1H-NMR光譜圖------------------------------110
圖18-1、Cinnamic acid (18)之IR吸收光譜圖-----------------------------113
圖18-2、Cinnamic acid (18)之1H-NMR吸收光譜圖---------------------113
圖18-3、Cinnamic acid (18)之EIMS質譜圖-------------------------------114
圖19-1、b-sitosterol (19) & stigmasterol (20)之IR吸收光譜圖--------118
圖19-2、b-sitosterol (19) & stigmasterol (20)之1H-NMR光譜圖------118
圖19-3、b-sitosterol (19) & stigmasterol (20)之EIMS之質譜圖-------119
表一、國內外哥納香屬之成分研究--------------------------------------------3
表二、本實驗室過去對恆春哥納香莖部所獲得之生物鹼---------------16
表三、本實驗室過去對恆春哥納香葉部所獲得之成分------------------16
表四、Styrylpyrones之活性---------------------------------------------------122
第七章 參考文獻
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