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    Please use this identifier to cite or link to this item: https://ir.fy.edu.tw:8080/ir/handle/987654321/10518


    Title: 冷子番荔枝化學成分和生物活性之研究
    Other Titles: Studies on the Chemical Constituents and Biological Activities of Annona cherimola Mill.
    Authors: 陳中一
    Contributors: 輔英科技大學 醫學檢驗生物技術系
    Keywords: 番荔枝科;生物鹼;Cherimoline;Cherinonaine;乙醯生合成物;Aromin-A;抗血小板凝集;細胞毒殺作用;Annonaceae;Alkaloids;Cherimoline;Cherinonaine;Acetogenins;Aromin-A;Antiplatelet Aggregation;Cytotoxicity
    Date: 1999
    Issue Date: 2010-11-24 14:51:08 (UTC+8)
    Abstract: 為了持續一貫對台灣產番荔枝科植物 (Formosan Annonaceous plants) 相關抗血小板凝集,抗腫瘤與抗 HIV 病毒等之活性成分物質的開發與研究,採集了台灣產番荔枝科 Annona 屬植物-----冷子番荔枝 (Annona cherimola Mill.) 之莖部及葉部,分別進行其成分與生物活性關係之探討。由冷子番荔枝的莖部進行化學成分分離與純化,共計得到八十九個化合物,包括:三十二個 Alkaloid 類化合物,分別為 [liriodenine (1), lysicamine (2), atherospermidine (3), oxoxylopine (4), oxoanolobine (5), oxoasimilobine (6), oxoglaucine (7), (-)-anonaine (9), (-)-asimilobine (10), (-)-norstephalagine (11), (-)-xylopine (12), (-)-anolobine (13), (-)-norisocorydine (14), (-)-N-methylasimilobine (15), (-)-romucosine (16), (-)-N-formylanonaine (17), (+)-laurotetanine (18), (+)-isocorydine (19), (+)-N-methyllaurotetanine (20), (+)-norisocorydine (21), (-)-norushinsunine (22), (-)-ushinsunine (23), (-)-artabonatine A (24), (+)-stepharine (25), (+)-pronuciferine (26), (+)-orentaline (27), (-)-kikemanine (28), thalifoline (29), doryphornine (30), nicotinic acid (34), cherimoline (35) 及 cheritamine (36)];九個Amide類化合物,分別為 [N-p-coumaroyltyramine (37), N-trans-caffeoyltyramine (38), N-trans-feruloyltyramine (39), dihydro-feruloyltyramine (40), N-cis-feruloyltyramine (41), N-cis-caffeoyltyramine (42), N-trans-feruloylmethoxytyramine (43), N-cis-feruloylmethoxy-tyramine (44) 及 cherinonaine (45)];十個 Kaurane 類化合物,分別為[ent-kaur-16-en-19-oic acid (46), 16b-hydro-17-acetoxy-ent-kauran-19-oic acid (47), 16b-hydroxy-17-acetoxy-ent-kauran-19-oic acid (48), 16a-hydro-17-acetoxy-ent-kauran-19-oic acid (49), 16b-hydro-17-hydroxy-ent-kauran-19-oic acid (50), 16a-hydro-17-hydroxy-ent-kauran-19-oic acid (51), 16b-hydroxy-17-acetoxy-ent-kauran-19-al (52), 16b-hydro-17-hydroxy-ent-kauran-19-al (53), 16a-hydro-17-hydroxy-ent-kauran-19-al (54) 及 16b-hydroxy-17,19-diacetoxy-ent-kaurane (55)];四個 Lignan 類化合物,分別為 [(+)-syringaresinol (56), (+)-dia-syringaresinol (57), (+)-epi-syringaresinol (58), liriodendrin ((+)-syringaresinol-di-O-b-D-glucopyranoside) (59)]。九個 Steroids 類化合物,分別為 [b-sitosterol (60), stigmasterol (61), b-sitostenone (62), stigmasta-4,22-dien-3-one (63), 6b-hydroxy-b-sitosterone (64), 6b-hydroxystigmasterone (65), b-sitosteryl-D-glucoside (66), stigmasteryl-D-glucoside (67) 及 6''-(b-sitosteryl-3-O-b-glucopyranosyl) hexadecanoate (68)];二個 Acetogenin 類化合物,分別為 [squamocin (69) 及 aromin-A [19,20-erythro-aromin] (70)];十九個 Benzenoid 類化合物,分別為 [p-hydroxybenzadehyde (71), p-hydroxybenzoic acid (72), methylparaben (73), 3-chloro- benzoic acid (75), vanillin (76), isovanillin (77), vanillic acid (78), isovanillic acid (79), methyl vanillate (80), methyl isovanillate (81), syringaldehyde (82), syringic acid (83), 3,4,5-trimethoxybenzoic acid (84), trans-methyl p-coumarate (85), ferulic acid (87), p-dihydrocoumaric acid (88), 3-(4-hydroxy-3,5-dimethoxyphenyl)-1,2-propanediol (89), 3,4,5-trimethoxyphenyl-b-D-glucopyranoside (90) 及 thalictoside (91)] ;二個 Purine 類化合物,分別為 [adenosine (31) 及 uridine (32)] ;一個 Lactam amide 化合物,為 [squamolone (33)] 以及一個 Quinone 化合物,為 [2,6-dimethoxy-p-benzoquinone (92)]。由冷子番荔枝之葉部進行化學成分分離與純化,共計得到十九個化合物,包括:六個 Alkaloid 類化合物,分別為 [liriodenine (1), oxoxylopine (4), oxonantenine (8), asimilobine (10), xylopine (12) 及 anolobine (13)]; 四個Steroid 類化合物,分別為 [b-sitosterol (60), stigmasterol (61), b-sitosterol-D-glucoside (66) 及 stigmasterol-D-glucoside (67)] 及九個 Benzenoid 類化合物,分別為 [p-hydroxybenzaldehyde (71), p-hydroxybenzoic acid (72), methylparaben (73), 4-methoxybenzoic acid methyl ester (74), vanillin (76), methyl vanillate (80), trans-methyl p-coumarate (85), cis-methyl p-coumarate (86) 及 p-dihydrocoumaric acid (88)]。以上化合物經由光譜分析並配合衍生物之製作,加以證明及確認其結構式。其中化合物 14, 24, 35, 36, 40, 42, 43, 44, 45, 55 與 70 為新化合物,58 及 75 為首次分離得到之化合物,除了化合物 1, 2, 9, 10, 13, 31, 33, 39, 60 與 61 之外,其餘皆為首次自該植物中分離得到。
    上述化合物之相關生物活性研究,在抗血小板凝集試驗方面,化合物 2, 10, 12, 13, 16, 20, 37, 38 和 39 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 2, 13 和 20 對於 platelet-activating factor (PAF) 所誘發之血小板凝集有明顯的抑制效果; 化合物10, 13 和 15 對於 collagen 所誘發之血小板凝集有明顯的抑制作用; 化合物 12, 13, 18, 19 和 23 對於 thrombin 所誘發之血小板凝集有明顯的抑制效果。在抗癌活性研究方面,化合物 69 對肝癌細胞 (Hep G2 & Hep 2,2,15)、鼻咽癌細胞 (KB) 及直腸癌細胞 (CCM2) 皆有很強的毒殺效果;化合物 70 對肝癌細胞 (Hep G2 & Hep 2,2,15) 則展現出邊緣的毒殺效果;化合物 9 對肝癌細胞 (59T & Hep G2 & SKHep1) 及胃癌細胞 (AGS) 具有很強的毒殺效果,而對於直腸癌細胞 (DLD1) 則展現出邊緣的毒殺效果;而化合物 45 對於肝癌細胞 (59T) 則具有強力並選擇性的毒殺作用。
    除此之外,以半合成所製備的 N-(methoxycarbonyl)aporphine 以及dehydroaporphine 型生物鹼之抗血小板凝集活性仍在測試中
    Relation: 高雄醫學院 藥學研究所 博士論文
    Appears in Collections:[醫學檢驗生物技術系] 博碩士論文

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