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研究生:賈宜琛
研究生(外文):Chia Yi-Chen
論文名稱:毛瓜馥木與多脈瓜馥木化學成分及異奎寧型生物鹼抗血小板凝集作用之研究
論文名稱(外文):Studies on the Chemical Constituents of Fissistigma oldhamii and F. balansae and the Antiplatelet Aggregation Activities of Isoquinoline Alkaloids
指導教授:吳永昌
指導教授(外文):Wu Yang-Chang
學位類別:博士
校院名稱:高雄醫學大學
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:2000
畢業學年度:88
語文別:中文
中文關鍵詞:番荔枝科瓜馥木屬毛瓜馥木多脈瓜馥木抗血小板凝集作用異奎寧型生物鹼
外文關鍵詞:AnnonaceaeFissistigmaFissistigma oldhamiiFissistigma balansaeAntiplatelet Aggregation ActivitiesIsoquinoline Alkaloids
相關次數:
  • 被引用被引用:8
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本論文延續番荔枝科植物(Annonaceous plants)相關抗血小板凝集等活性成分物質的開發與化學成分的分類研究,分別採集台灣產番荔枝科瓜馥木屬(Fissistigma)植物---毛瓜馥木[Fissistigma oldhamii (Hemsl.) Merr.]與大陸雲南產同屬植物---多脈瓜馥木[F. balansae (A. DC.) Merr.],進行其成分與抗血小板凝集作用的探討。由毛瓜馥木的莖部進行化學成分分離與純化,共計得到四十三個化合物,包括:二十八個alkaloid類化合物,分別為[liriodenine (1), oxoxylopine (2), oxocrebanine (3), oxoisocalycinine (5), O-methylmoschatoline (6), noraristolodione (7), (-)-anonaine (10), (-)-xylopine (11), (-)-dicentrine (12), (-)-crebanine (13), (-)-O-methyllirinine (14), piperlactam A (23), piperlactam C (24), aristolactam A II (25), aristolactam B III (28), aristolactam F II (29), goniothalactam (30), velutinam (31), isostigmalactam (32), stigmalactam (33), N-trans-feruloyltyramine (34), N-trans-cinnamoyltyramine (35), N-cis-feruloyltyramine (36), (-)-tetrahydropalmatine (37), (-)-stepholidine (38), palmatine (42), O-methylflavinantine (47)及squamolone (48)];十個flavonoid類化合物,分別為[5,8-dihydroxy-6,7-dimethoxyflavone (49), 6-hydroxy-5,7,8-trimethoxyflavone (50), 6,8-dihydroxy-5,7-dimethoxyflavone (51), 5,6,8-trihydroxy-7-methoxyflavanone (53), 5,8-dihydroxy-6,7-dimethoxyflavanone (54) isopedicin (55), kanakugin (56), dihydrooroxylin A (57), O-methylonysilin (58) 及6,8-dihydroxy-5,7-dimethoxyflavanone (59)];一個phenanthrene類化合物,為[perakensol (68)];二個steroid類化合物,分別為[-sitosterol (69)及stigmasterol (71)] 以及二個benzenoid類化合物,分別為[trans-cinnamic acid (73)及syringic acid (74)]。由毛瓜馥木的未成熟果實部進行化學成分分離與純化,共計得到十一個化合物,包括:二個alkaloid類化合物,分別為[oxoxylopine (2)及(-)-N-methyl carboxylate xylopine (20)];四個flavonoid類化合物,分別為[pinostrobin (60), onysilin (61), 5-hydroxy-6,7,8-trimethoxyflavanone (62)及5-hydroxy-7,8-dimethoxyflavone (63)];一個furanone類化合物,為[fissohamione (65)];二個cyclopentenone類化合物,分別為[stigmahamone I (66)及stigmahamone II (67)] 以及二個steroid類化合物,分別為[-sitosterol (69)及stigmasterol (71)]。由多脈瓜馥木的枝葉部進行化學成分分離與純化,共計得到四十五個化合物,包括:三十一個alkaloid類化合物,分別為[liriodenine (1), oxoxylopine (2), oxobuxifoline (4), noraristolodione (7), norcepharadione B (8), 7-chloronorcepharadione B (9), (-)-xylopine (11), (-)-isolaureline (15), (-)-discoguattine (16), (-)-fissoldine (17), (-)-N-methylfissoldine (18), (-)-N-methylnandigerine (19), (-)-N-methyl carboxylate xylopine (20), fissilandione (21), norfissilandione (22), piperlactam A (23), piperlactam C (24), aristolactam A II (25), aristolactam AⅢa (26), aristolactam B II (27), aristolactam B Ⅲ (28), aristolactam F II (29), goniothalactam (30), N-trans-feruloyltyramine (34), (-)-kikemanine (39), (-)-discretamine (40), (-)-thaipetaline (41), columbamine (43), dehydrodiscretamine (44), dehydrocorydalmine (45)及fissisaine (46)];二個flavonoid類化合物,為[kaempferol-3-O-rhamnoside (52)及catechin (64)];四個steroid類化合物,分別為[-sitosterol (69), -sitosteryl-D-glucoside (70), stigmasterol (71)及stigmasteryl-D-glucoside (72)];七個benzenoid類化合物,分別為[trans-cinnamic acid (73), syringic acid (74), vanillic acid (75), p-hydroxybenzoic acid (76), p-hydroxybenzaldehyde (77), protocatechuic acid (78)及3,4,5-trimethoxyphenyl--D-glucopyranoside (79)]以及一個biphenyltetraol類化合物,為[biphenyl-3,4,3'',4''-tetraol (80)]。以上化合物經由光譜分析和配合衍生物之製作,加以證明及確認其結構式,其中化合物65屬於furanone類新骨架化合物, 66與67屬於cyclopentenone類新骨架化合物,化合物20, 21, 22, 32, 33, 46, 51, 與59為新化合物,化合物36為首次自天然界分離得到的化合物,而除了1, 2, 3, 6, 7, 8, 10, 11, 12, 13, 17, 23, 24, 25, 27, 28, 30, 34, 40, 47, 49, 54, 69, 71, 73與74等二十六個化合物之外,其餘皆是首次自該屬植物分離得到。
另由該屬植物所分離得到aristolactam與dioxoaporphine型生物鹼化合物進行抗血小板凝集活性之研究,顯示化合物7, 23, 24, 28, 29, 30, 32與33對於 arachidonic acid (AA) 所誘發之血小板凝集有明顯的抑制作用;化合物7, 23, 24, 25, 26, 28, 29, 30, 31與32對於 collagen 所誘發之血小板凝集有明顯的的抑制作用;化合物24, 26, 29, 30, 32與33對於 platelet-activating factor (PAF) 所誘發之血小板凝集有明顯的抑制效果。推論其化合物結構與抗血小板凝集活性的相關性:
1.本類型化合物主要對於AA及collagen所誘發血小板的凝集作用有較佳的抑制效果。
2.aristolactam類化合物結構,於C-2、C-3及C-4接有含氧取代基,具有最強的抑制PAF誘導血小板凝集活性,如果D環接上一個OH基則其活性下降。
3.本類型化合物的結構,於A環上有二個甲氧基取代,D環無取代,反而促進血小板凝集。
另由本實驗室以往分離到的aporphine與7-dehydroaporphine型生物鹼化合物進行抗血小板凝集活性之研究,推論化合物結構與活性的相關性:
1.dehydroaporphine類化合物對於AA及collagen所誘發血小板的凝集作用有較佳的抑制效果,如果於C-7接上OH基,會增強抑制PAF誘導血小板凝集活性。
2.aporphine類化合物經製備形成鹽類,會改變抗血小板凝集活性,其影響效果不一。
除此之外,以半合成所製備的p-quinonoids型生物鹼與其他類型化合物之抗血小板凝集活性與細胞毒性仍在測試中。
As a series of studies on the chemical constituents and biological activities of Formosan Annonaceous plants, the methanolic extracts of stems and unripe fruits of Fissistigma oldhamii (Hemsl.) Merr., and ethanolic extracts of twigs of Fissistigma balansae (A. DC.) Merr. were investigated, respectively. Forty-three compounds including twenty-eight alkaloids [liriodenine (1), oxoxylopine (2), oxocrebanine (3), oxoisocalycinine (5), O-methylmoschatoline (6), noraristolodione (7), (-)-anonaine (10), (-)-xylopine (11), (-)-dicentrine (12), (-)-crebanine (13), (-)-O-methyllirinine (14), piperlactam A (23), piperlactam C (24), aristolactam A II (25), aristolactam B III (28), aristolactam F II (29), goniothalactam (30), velutinam (31), isostigmalactam (32), stigmalactam (33), N-trans-feruloyltyramine (34), N-trans-cinnamoyltyramine (35), N-cis-feruloyltyramine (36), (-)-tetrahydropalmatine (37), (-)-stepholidine (38), palmatine (42), O-methylflavinantine (47) and squamolone (48)]; ten flavonoids [5,8-dihydroxy-6,7-dimethoxyflavone (49), 6-hydroxy-5,7,8-trimethoxyflavone (50), 6,8-dihydroxy-5,7-dimethoxyflavone (51), 5,6,8-trihydroxy-7-methoxyflavanone (53), 5,8-dihydroxy-6,7-dimethoxyflavanone (54), isopedicin (55), kanakugin (56), dihydrooroxylin A (57), O-methylonysilin (58) and 6,8-dihydroxy-5,7-dimethoxyflavanone (59)]; one phenanthrene [perakensol (68)]; two steroids [-sitosterol (69) and stigmasterol (71)] and two benzenoids [trans-cinnamic acid (73) and syringic acid (74)] were isolated from the stems of F. oldhamii. Eleven compounds including two alkaloids [oxoxylopine (2) and (-)-N-methyl carboxylate xylopine (20)]; four flavonoids [pinostrobin (60), onysilin (61), 5-hydroxy-6,7,8-trimethoxyflavanone (62), and 5-hydroxy-7,8-dimethoxyflavone (63)]; one furanone [fissohamione (65)]; two cyclopentenones [stigmahamone I (66) and stigmahamone II (67)] and two steroids [-sitosterol (69) and stigmasterol (71)] were isolated from the unripe fruits of F. oldhamii. Forty-five compounds including thirty-one alkaloids [liriodenine (1), oxoxylopine (2), oxobuxifoline (4), noraristolodione (7), norcepharadione B (8), 7-chloronorcepharadione B (9), (-)-xylopine (11), (-)-isolaureline (15), (-)-discoguattine (16), (-)-fissoldine (17), (-)-N-methylfissoldine (18), (-)-N-methylnandigerine (19), (-)-N-methyl carboxylate xylopine (20), fissilandione (21), norfissilandione (22), piperlactam A (23), piperlactam C (24), aristolactam A II (25), aristolactam A Ⅲa (26), aristolactam B II (27), aristolactam B Ⅲ (28), aristolactam F II (29), goniothalactam (30), N-trans-feruloyltyramine (34), (-)-kikemanine (39), (-)-discretamine (40), (-)-thaipetaline (41), columbamine (43), dehydrodiscretamine (44), dehydrocorydalmine (45) and fissisaine (46),]; two flavonoids [kaempferol-3-O-rhamnoside (52) and catechin (64)]; four steroids [-sitosterol (69), -sitosteryl-D-glucoside (70), stigmasterol (71) and stigmasteryl-D-glucoside (72)]; seven benzenoids [trans-cinnamic acid (73), syringic acid (74), vanillic acid (75), p-hydroxybenzoic acid (76), p-hydroxybenzaldehyde (77), protocatechuic acid (78) and 3,4,5-trimethoxyphenyl--D-glucopyranoside (79)] and one biphenyltetraol [biphenyl-3,4,3'',4''-tetraol (80)] were isolated from the twigs of F. balansae. The structures of these compounds were identified by spectral data interpretation or confirmed by chemical methods. Among them, 65 is a novel furanone; 66 and 67 are two novel cyclopentenones; 20, 21, 22, 32, 33, 46, 51, and 59, are new compounds. Compound 36 was isolated from natural sources for the first time though they had been synthesized previously. All compounds, except 1, 2, 3, 6, 7, 8, 10, 11, 12, 13, 17, 23, 24, 25, 27, 28, 30, 34, 40, 47, 49, 54, 69, 71, 73 and 74, are found for the first time from the Fissistigma species.
Aristolactams and dioxoaporphines had been isolated from these species and subjected to the antiplatelet testing. At a concentration of 100 g/mL, compounds 7, 23, 24, 28, 29, 30, 32 and 33 showed significant inhibition of arachidonic acid (AA)-induced platelet aggregation. Compounds 7, 23, 24, 25, 26, 28, 29, 30, 31 and 32 showed inhibition of collagen-induced platelet aggregation. Compounds 24, 26, 29, 30, 32 and 33 exhibited inhibition of platelet-activating factor (PAF)-induced platelet aggregation. From the results obtained, the following structure-activity conclusions can be drawn in terms of antiplatelet effects:
1. Aristolactams and dioxoaporphines showed significant inhibition of AA- and collagen-induced platelet aggregation.
2. The aristolactams containing three oxygenated substituents in ring A and no substitution in ring D led to the strong inhibition of PAF-induced platelet aggregation. When a hydroxyl group was present in ring D, the antiplatelet activity was reduced.
3. The aristolactams or dioxoaporphines containing two methoxyl groups in ring A and no substitution in ring D, promoted the platelet aggregation caused by these inducers.
Aporphines, 7-dehydroaporphines and some semi-synthetic derivatives, which were isolated from Formosan plants and prepared by our laboratory, were also tested for their antiplatelet effects. The conclusions can be drawn in terms of antiplatelet effects:
1. Dehydroaporphine alkaloids are significantly active against AA- and collagen-induced aggregation, and inhibition of PAF-induced aggregation was enhanced if a hydroxy group was attached at the C-7 position.
2. The parent aporphines and their salts have varying effects on the inhibition of aggregation induced by ADP, AA, collagen and PAF.
The compounds of semisynthesis of p-quinonoids aporphine and the other isolates on antiplatelet aggregation testing and cytotoxicity bioassay are currently under investigation.
封面
目錄
圖表目錄
中文摘要
英文摘要
第一章 序論
第一節 前言
第二節 文獻回顧
第三節 植物之分佈及型態
第四節 研究目的
第二章 研究材料成分之抽取的分離
第三章 化合物之結構證明
第一節 O-Methylmoschatoline(6)之結構證明
第二節 Norcepharadione B(8)之結構證明
第三節 (-)-O-Methyllirinine(14)之結構證明
第四節 (-)-N-Methylfissoldine(18)之結構證明
第五節 (-)-N-Methylcarboxylate xylopine(20)之結構證明
第六節 Fissilandione(21)之結構證明
第七節 Norfissilandione(22)之結構證明
第八節 Piperlactam C(24)之結構證明
第九節 Aristolactam AIIIa(26)之結構證明
第十節 Goniothalactam(30)之結構證明
第十一節 Velutinam(31)之結構證明
第十二節 Isostigmalactam(32)之結構證明
第十三節 Stigmalactam(33)之結構證明
第十四節 N-trans-Feruloyltyramine(34)之結構證明
第十五節 N-trans-Cinnamoyltyramine(35)之結構證明
第十六節 (-)-Discretamine(40)之結構證明
第十七節 (-)-Thaipetaline(41)之結構證明
第十八節 Dehydrodiscretamine(44)之結構證明
第十九節 Fissisaine(46)之結構證明
第二十節 O-Methylflavinantine(47)之結構證明
第二十一節 6-Hydroxy05,7,8-trimethoxyflavone(50)之結構證明
第二十二節 6,8-Dihydroxy-5,7-dimethoxyflavone(51)之結構證明
第二十三節 Isopedicin(55)之結構證明
第二十四節 Kanakugin(56)之結構證明
第二十五節 6,8-Dihydroxy-5,7-dimethoxyflavanone(59)之結構證明
第二十六節 Fissohamione(66)之結構證明
第二十七節 Stigmahamone I(67)之結構證明
第二十八節 Stigmahamone II(68)之結構證明
第二十九節 Perakensol(69)之結構證明
第三十節 Bipheny1-3,4,3'',4''-tetraol(79)之結構證明
第四章 抗血小板凝集活性試驗
第五章 Aporphine生物鹼的反應
第六章 結論
第七章 相關實驗部份
第一節 儀器與材料
第二節 植物材料與分離純化
第三節 各化合物之物理及光譜數據
第八章 參考文獻
第九章 論文著作及發表
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