臺灣博碩士論文加值系統

　　腺果藤 (Pisonia aculeata L.)屬於紫茉莉科 (Nyctaginaceae)，為一灌木狀帶刺之木質攀緣藤本，分布於中國南部、琉球、印度、馬來西亞、印尼及台灣東、南部沿海及低海拔地區。過去本實驗室針對多種台灣產植物做活性及成分之研究，發現P. aculeata甲醇萃取物具有抗結核活性，且其化學成分尚未被研究。
　　將腺果藤合併莖部及根部之甲醇萃取物經分配萃取後，得到乙酸乙酯、正丁醇及水可溶部。由乙酸乙酯可溶部具抗結核活性層進行化學成分之研究分離出十個chromone類：pisonin A (1)、pisonin B (2)、pisonin C (3)、pisonin D (4)、pisonin E (5)、pisonin F (6)、5-hydroxy-7-methoxy-2-methylchromone (7)、5-hydroxy-6,7- methoxy-2-methylchromone (8)、leptorumol (9)、noreugenin (10)，七個flavanoid類：pisonivanone (11)、dihydrooroxylin A (12)、2''-hydroxymethoxymatteucinol (13)、pisonivanol (14)、(2R,3R)-5-methoxy-6,7-methylenedioxyflavanonol (15)、pisonianone (16)、6,8-dimethylisogenistein (17)，四個amide類：pisoniamide (18)、N-trans-feruloyl-4''-O-methyldopamine (19)、N-trans-feruloyltyramine (20)、(R)-N-trans-feruloyloctopamine (21)，一個phenyl propanoid類：trans-methyl ferulate (22)，三個benzenoid類：vanillin (23)、4-hydroxybenzaldehyde (24)、syringaldehyde (25)，一個triterpenoid類：pisonolic acid (26)，三個steroid類：ergosterol peroxide (27)、混合物β-sitosterol (28)與stigmasterol (29)，一個chlorophyll類：pheophorbide a methyl ester (30)。以上化合物皆以各種圖譜分析來決定結構。
　　所有分離得到的化合物中，化合物1, 2, 4, 5, 11, 14, 16為新化合物，化合物3, 6, 18, 21, 26為天然首次分離得到之化合物，而化合物2, 11, 12, 13, 19, 20, 21顯示抗結核之活性。

　　Pisonia aculeata L. (Nyctaginaceae) is a scandent shrub with pricks, which distributed in south China, the Ryukyus, India, Malaysia, Indonesia and in thickets along the seashores and open forests at low elevations in the south and east of Taiwan. In a series of studies on the active constituents of Formosan plants, the MeOH extract of the combined stem and root of this plant showed antitubercular activity against Mycobacterium tuberculosis H37Rv in vitro. The chemical constituents of P. aculeata have never been conducted.
　　The MeOH extract of the combined stem and root of this plant was partitioned into EtOAc, n-BuOH and H2O-soluble parts. Investigation of the anti-TB active EtOAc-soluble extract led to the isolation of thirty compounds, including ten chromones: pisonin A (1), pisonin B (2), pisonin C (3), pisonin D (4), pisonin E (5), pisonin F (6), 5-hydroxy-7-methoxy-2-methylchromone (7), 5-hydroxy-6,7-methoxy- 2- methylchromone (8), leptorumol (9) and noreugenin (10); eight flavanoids: pisonivanone (11), dihydrooroxylin A (12), 2''-hydroxymethoxymatteucinol (13), pisonivanol (14), (2R,3R)-5-methoxy-6,7-methylenedioxyflavanonol (15), pisoniaone (16) and 6,8-dimethylisogenistein (17); five amides: pisoniamide (18), N-trans-feruloyl-4''-O-methyldopamine (19), N-trans-feruloyltyramine (20) and (R)-N-trans-feruloyloctopamine (21); one phenyl propanoid: trans-methyl ferulate (22); three benzenoids: vanillin (23), 4-hydroxybenzaldehyde (24) and syringaldehyde (25); one triterpenoid: pisonolic acid (26); three steroids: ergosterol peroxide (27), the mixtures of β-sitosterol (28) and stigmasterol (29); one chlorophyll: pheophorbide a methyl ester (30). The structures of these compounds were elucidated by spectral analysis.
　　Among these isolates, 1, 2, 4, 5, 11, 14 and 16 were new compounds, and compounds 3, 6, 18, 21 and 26 were first isolated from natural source. Compounds 2, 11, 12, 13, 19, 20 and 21 showed antitubercular activity in vitro.

目錄..........I-III
圖目錄..........IV
表目錄..........XII
中文摘要..........XIII
英文摘要..........XIV
Glossary of Abbreviations..........XV

第一章　緒論..........1
第二章　研究動機與目的..........3
第三章　皮孫木屬植物成分及藥理之研究回顧..........5
第四章　抗結核植物之研究文獻回顧..........13
第五章　萃取與分離..........14
第六章　結果與討論
第一節　pisonin A (1) 之結構研究..........20
第二節　pisonin B (2) 之結構研究..........27
第三節　pisonin C (3) 之結構研究..........34
第四節　pisonin D (4) 之結構研究..........41
第五節　pisonin E (5) 之結構研究..........48
第六節　pisonin F (6) 之結構研究..........55
第七節　5-hydroxy-7-methoxy-2-methylchromone (7) 之結構研究..........62
第八節　5-hydroxy-6,7-methoxy-2-methylchromone (8) 之結構研究..........65
第九節　leptorumol (9) 之結構研究..........68
第十節　noreugenin (10) 之結構研究..........71
第十一節　pisonivanone (11) 之結構研究..........74
第十二節　dihydrooroxylin A (12) 之結構研究..........82
第十三節　2''-hydroxymethoxymatteucinol (13) 之結構研究..........86
第十四節　pisonivanol (14) 之結構研究之結構研究..........92
第十五節　(2R,3R)-5-methoxy-6,7-methylenedioxyflavanonol (15)之結構研究..........101
第十六節　pisonianone (16) 之結構研究..........106
第十七節　6,8-dimethylisogenistein (17) 之結構研究..........114
第十八節　pisoniamide (18) 之結構研究..........118
第十九節　N-trans-feruloyl-4''-O-methyldopamine (19) 之結構研究..........125
第二十節　N-trans-feruloyltyramine (20) 之結構研究..........129
第二十一節　N-trans-feruloyloctopamine (21) 之結構研究..........133
第二十二節　trans-methylferulate (22) 之結構研究..........137
第二十三節　vanillin (23) 之結構研究..........140
第二十四節　4-hydroxybenzaldehyde (24) 之結構研究..........143
第二十五節　syringaldehyde (25) 之結構研究..........146
第二十六節　pisonolic acid (26) 之結構研究..........149
第二十七節　ergosterol peroxide (27) 之結構研究..........157
第二十八節　混合物β-sitosterol (28)與stigmasterol (29) 之結構研究..........162
第二十九節　pheophorbide a methyl ester (30) 之結構研究..........165
第七章　抗結核活性之研究..........168
第八章　結論..........170
第九章　相關實驗部份
第一節　儀器與材料..........172
第二節　莖部及根部之萃取與分離..........174

第三節　乙酸乙酯可溶部之分離..........174
第四節　抗結核活性試驗法..........177
第五節　各化合物之實驗數據..........178
第十章　參考文獻..........194

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