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  3. 藥學專業學院
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請用此 Handle URI 來引用此文件: http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/42799
完整後設資料紀錄
DC 欄位值語言
dc.contributor.advisor沈雅敬(Ya-Ching Shen)
dc.contributor.authorYa-Chu Linen
dc.contributor.author林雅竹zh_TW
dc.date.accessioned2021-06-15T01:23:55Z-
dc.date.available2011-09-15
dc.date.copyright2009-09-15
dc.date.issued2009
dc.date.submitted2009-07-24
dc.identifier.citation1. Isao, K., Naosuke, B., Miwa, H., Nobusuke, K., Masakatsu, T., Hiroshi, K., Chun, S. Y., & Sadao, S. (1989). Isolation of three new sesquiterpene lactones from the pericarps of Illicium majus. Chem. Pharm. Bull., 37(9), 2448-2451.
2. Chun, S. Y., Miwa, H., Naosuke, B., Masakatsu, T., Hiroshi, K., Nobusuke, K., & Isao, K. (1990). A new toxic neoanisatin derivative from the pericarps of Illicium majus. Chem. Pharm. Bull., 38(1), 291-292.
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6. Jian, M. H., Ritsuko, Y., Chun, S. Y., & Yoshiyasu, F. (2001). Structure and neurotrophic activity of seco-prezizaane-type sesquiterpenes from Illicium merrillianum. J. Nat. Prod., 64(4), 428-431.
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32. Yoshiyasu, F., Naomi, S., Mitsuaki, K., Masaru, K., Masakazu, N., et al. (1992). Illicinolides A and B, novel sesquiterpene lactones from the wood of Illicium tashiroi. Tetrahedron, 48(28), 5847-5854.
33. Isao, K., Yukari, Y., Satomi, S., Miki, S., & Chun, S. Y. (1992). Phenylpropanoids from the barks of Illicium difengpi. Chem. Pharm. Bull., 40(9), 2461-2464.
34. Isao, K., Chifumi, I., Yuki, K., Takashi, T., & Chun, S. Y. (1994). A new triphenyl-type neolignan and a biphenylneolignan from the bark of Illicum simonsii. Chem. Pharm. Bull., 42(1), 112-114.
35. Yoshiyasu, F., Naomi, S., Yuuko, H., & Mitsuaki, K. (1994). Prenylated C6-C3 compounds from Illicium tashroi. Phytochemistry, 36(6), 1497-1503.
36. Yoshiyasu, F., Naomi, S., & Mitsuaki, K. (1995). Tashironin, A plausible biosynthetic precursor of anisatin-type sesquiterpenes. Tetrahedron Lett., 36(4), 583-586.
37. Jian, M. H., & Chun, S. Y. (1996). Pseudoanisatin-like sesquiterpene lactones from the pericarps of Illicium dunnianum. Phytochemistry, 42(5), 1375-1376.
38. Lai, K. S., & Geoffrey, D. B. (1996). A sesquilignan from Illicium dunnianum. Phytochemistry, 43(6), 1417-1419.
39. Lai, K. S., Richard, M. K. S., & Geoffery, D. B. (1997). Phytochemistry of Illicium dunnianum and the systematic position of the illiciaceae. Phytochemistry, 44(6), 1099-1108.
40. Jian, M. H., Jia, L. W., & Chun, S. Y. (1997). Sesquiterpene lactones from the pericarp of Illicium dunnianum. Phytochemistry, 46(4), 777-780.
41. Isao, K., Shigeko, S., Zhi, H. J., & Takashi, T. (1997). Prenylated C6-C3 compounds from root bark of Illicium anisatum. Phytochemistry, 46(8), 1389-1392.
42. Lai, K. S., & Geoffery, D. B. (1998). A sesquiterpene class from Illicium dunnianum. Phytochemistry, 47(2), 301-302.
43. Thomas, J. S., Hildegard, M. S., Eva, M., Wilfried, P., Frank, R. F., et al. (1998). New sesquiterpene lactones from Illicium floridanum. J. Nat. Prod., 61(2), 230-236.
44. Lai, K. S., & Geoffery, D. B. (1998). Novel phenylpropanoids and lignans from Illicium verum. J. Nat. Prod., 61(8), 987-992.
45. Lai, K. S., & Geoffery, D. B. (1998). A seco-cycloartane from Illcium verum. Phytochemistry, 48(7), 1169-1171.
46. Lai, K. S., & Geoffery, D. B. (1998). A prezizaane sesquiterpene from Illcium angustisepalum. Phytochemistry, 49(6), 1715-1717.
47. Lai, K. S., & Geoffery, D. B. (1998). Abietane diterpenes from Illcium angustisepalum. J. Nat. Prod., 61(7), 907-912
48. Jian, M. H., Chun, S. Y., Hai, W., Qiu, M. W., Jia, L. W., & Yoshiyasu, F. (1999). Structure of novel sesquiterpenes from the pericarps of Illicium merrillianum. Chem. Pharm. Bull., 47(12), 1749-1752.
49. Koon, S. N., & Geoffery, D. B. (1999). Santalane and isocampherenane sesquiterpenoids from Illicium tsangii. Phytochemistry, 50, 1213-1218.
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51. Thomas, J. S. (1999). Novel seco-prezizaane sesquiterpenes from north American Illicium species. J. Nat. Prod., 62(5), 684-687.
52. Koon, S. N., & Geoffery, D. B. (1999). Allohimachalane, seco-allohimachalane and himachalane sesquiterpenes from Illicium tsangii. Tetrahedron, 55, 759-770.
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dc.identifier.urihttp://tdr.lib.ntu.edu.tw/jspui/handle/123456789/42799-
dc.description.abstract本論文主要研究台灣產紅花八角 (Illicium arborescens Hayata) 果實之CH2Cl2與EtOAc混合液萃取物並分析鑑定其prenylated C6-C3類成分,分離共得12個化合物,包含3個新的與9個已知化合物。
由紅花八角分離得到一個類似prenylated C6-C3類化合物之新骨架化合物、一個prenylated C6-C3類化合物、一個phytoquinoid化合物,分別命名為illicaborin A (1)、illicaborin B (2)、illicaborin C (3),以及9個已知化合物,分別是1-allyl-2,3-
(methylenedioxy)-5-methoxybenzene (4) 、apiol (5) 、 illicinone E (6) 、11-epi-
illilinone E (7)、2,3-dehydroillifunone C (8)、illifunone A (9) 、illifunone B (10) 、illifunone C (11)、illifunone D (12)。

化合物1為一新骨架化合物,特徵為prenylated C6-C3骨架之C-2位置增加一個CH2OH基團,化合物2具有典型的prenylated C6-C3骨架,化合物3為phytoquinoid化合物。以上所有化合物結構是利用各種物理數據,包括紅外線、質譜、紫外線、旋光值以及配合各種核磁共振圖譜,包含1D和2D的圖譜並且比對過去文獻相關化合物的數據而得。立體結構解析方面,則是利用NOESY圖譜決定。化合物活性相關實驗則是委託郭曜豪老師實驗室協助測定,受測化合物1-3、8與11中,僅有2對於HEp-2、Daoy、MCF-7與WiDr等癌細胞具有些微細胞毒殺活性,其對以上細胞的ED50分別為10.32、14.52、16.82與17.16 μg/mL。
zh_TW
dc.description.abstractThis research focuses on prenylated C6-C3 compounds from the fruits of Illicium arborescens Hayata. The CH2Cl2 and EtOAc extracts of fruits were investigated by using chromatography to yield 12 compounds.
By using liquid chromatography, three new compounds named illicaborin A (1), illicaborin B (2), illicaborin C (3) were isolated, together with nine known compounds, 1-allyl-2,3-(methylenedioxy)-5-methoxybenzene (4), apiol (5), illicinone E (6), 11-epi-illilinone E (7), 2,3-dehydroillifunone C (8), illifunone A (9), illifunone B (10), illifunone C (11) and illifunone D (12)。
Compound 1 has a new skeleton which is analogous with prenylated C6-C3 skeleton, but compound 1 connects with an additional CH2OH group at C-2 position. The new compound 2 possesses a prenylated C6-C3 skeleton, and compound 3 is a new phytoquinoid. All structures of the above compounds were elucidated by means of 1D, 2D-NMR spectroscopic analysis and physical methods including IR, mass, UV, and optical rotation, and also by comparision with the published data. The relative configuration of compounds 1-3 was determined by NOESY experiment.
Cytotoxicity of compounds 1-3, 8, 11 was evaluated by Dr. Kuo’s lab. Compound 2 exhibited weak cytotoxicity against HEp-2, Daoy, MCF-7 and WiDr cell lines, as ED50 were 10.32, 14.52, 16.82 and 17.16 μg/mL, respectively.
en
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Previous issue date: 2009
en
dc.description.tableofcontents中文摘要 I
英文摘要 Ⅱ
第一章 序論 1
第一節 前言 1
第二節 相關化合物之文獻回顧 4
第二章 材料及方法 49
第一節  材料介紹 49
第二節 分離流程 51
第三節 實驗儀器 54
第四節 矽膠與溶劑 55
第三章 實驗結果 56
第一節 化合物1之結構解析 57
第二節 化合物2之結構解析 68
第三節 化合物3之結構解析 78
第四節 化合物4之結構 86
第五節 化合物5之結構 87
第六節 化合物6之結構 88
第七節 化合物7之結構 89
第八節 化合物8之結構 90
第九節 化合物9之結構 91
第十節 化合物10之結構 92
第十一節 化合物11之結構93
第十二節 化合物12之結構94
第十三節 活性測試結果 95
第四章 結論 97
第五章 參考文獻 101
dc.language.isozh-TW
dc.subject紅花八角zh_TW
dc.subjectillicabrin Czh_TW
dc.subjectillicabrin Bzh_TW
dc.subjectillicabrin Azh_TW
dc.subject細胞毒殺測試zh_TW
dc.subjectprenylated C6-C3化合物zh_TW
dc.title紅花八角果實Prenylated C6-C3類活性化合物研究zh_TW
dc.titleStudies on the Bioactive Prenylated C6-C3 compounds from the fruits of Illicium arborescens Hayataen
dc.typeThesis
dc.date.schoolyear97-2
dc.description.degree碩士
dc.contributor.oralexamcommittee郭曜豪(Yao-Haur Kuo),李宗徽(Tzong-Huei Lee)
dc.subject.keyword紅花八角,prenylated C6-C3化合物,細胞毒殺測試,illicabrin A,illicabrin B,illicabrin C,zh_TW
dc.subject.keywordIllicium arborescens Hayata,prenylated C6-C3,cytotoxicity,illicabrin A,illicabrin B,illicabrin C,en
dc.relation.page106
dc.rights.note有償授權
dc.date.accepted2009-07-24
dc.contributor.author-college醫學院zh_TW
dc.contributor.author-dept藥學研究所zh_TW
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