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請用此 Handle URI 來引用此文件: http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/29663
完整後設資料紀錄
DC 欄位值語言
dc.contributor.advisor李水盛(Shoei-Sheng Lee)
dc.contributor.authorHsin-Yi Chenen
dc.contributor.author陳欣苢zh_TW
dc.date.accessioned2021-06-13T01:14:03Z-
dc.date.available2021-08-03
dc.date.copyright2011-10-07
dc.date.issued2011
dc.date.submitted2011-08-03
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3. Hart, N. K.; Johns, S. R.; Lamber, J. A. Alkaloids of the Sapotaceae: trans-β- methylthioacrylate and tiglate esters of (-)-isoretronecanol from a Planchonella species. Australian Journal of Chemistry 1968, 21, 1393-1395.
4. Cambie, R. C.; Ser, N. A.; Kokubun, T. Heartwood constituents of Planchonella vitiensis. Biochemical Systematics and Ecology 1997, 25, 677-678.
5. Lee, S. S.; Tseng, C. C.; Chen, C. K. Three new benzophenone glucosides from the leaves of Planchonella obovata. Helvetica Chimica Acta 2010, 93, 522-529.
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9. Wu, B.; Lin, W. H. Studies on chemical constituents of Epiphyllum oxypetalum. Chinese Pharmaceutical Journal 2010, 45, 496-499.
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11. Beck, M. A.; Häberlein, H. Flavonol glycosides from Eschscholtzia californica. Phytochemistry 1999, 50, 329-332.
12. Fico, G.; Rodondi, G.; Flamini, G.; Passarella, D.; Tomé, F. Comparative phytochemical and morphological analyses of three Italian Primula species. Phytochemistry 2007, 68, 1683-1691.
13. Lee, S. S.; Wang, P. H. Polar chemical constituents from Phoebe formosana. Journal of the Chinese Chemical Society 1999, 46, 215-219.
14. Li, L.; Henry, G. E.; Seeram, N. P. Identification and bioactivities of resveratrol oligomers and flavonoids from Carex folliculata seeds. Journal of Agricultural and Food Chemistry 2009, 57, 7282-7287.
15. Sang, S.; Lapsley, K.; Jeong, W. S.; Lachance, P. A.; Ho, C. T.; Rosen, R. T. Antioxidative phenolic compounds isolated from almond skins (Prunus amygdalus Batsch). Journal of Agricultural and Food Chemistry 2002, 50, 2459-2463.
16. Nhiem, N.; Van Kiem, P.; Van Minh, C.; Lee, J. J.; Ku, J.; Myung, C. S.; Kim, Y. A potential inhibitor of rat aortic vascular smooth muscle cell proliferation from the pollen of Typha angustata. Archives of Pharmacal Research 2010, 33, 1937-1942.
17. Rastrelli, L.; Saturnino, P.; Schettino, O.; Dini, A. Studies on the constituents of Chenopodium pallidicaule (Canihua) seeds. Isolation and characterization of two new flavonol glycosides. Journal of Agricultural and Food Chemistry 1995, 43, 2020-2024.
18. Ramadan, M. A.; Ahmad, A. S.; Nafady, A. M.; Mansour, A. I. Chemical composition of the stem bark and leaves of Ficus pandurata Hance. Journal of Natural Product Research 2009, 23, 1218-1230.
19. Shukla, Y. N.; Thakur, R. S.; Pachaly, P. A bidesmosidic oleanolic acid saponin from Panax pseudo-ginseng. Phytochemistry 1992, 31, 1046-1048.
20. Nigam, S. K.; Li, X. C.; Wang, D. Z.; Misra, G.; Yang, C. R. Triterpenoidal saponins from Madhuca butyracea. Phytochemistry 1992, 31, 3169-3172.
21. Kitagawa, I.; Shirakawa, K.; Yoshikawa, M. Saponin and sapogenol. XXIV. The structure of Mi-saponin C, a bisdemoside of protobassic acid from the seed kernels of Madhuca longifolia (L.) Macbride. Chemical & Pharmceutical Bulletin 1978, 26, 1100-1110.
22. Kitagawa, I.; Inada, A.; Yosioka, I. Saponin and sapogenol. XII. Mi-saponin A and Mi-saponin B, two major bisdesmosides from the seed kernels of Madhuca longifolia (L.) Macbride. Chemical & Pharmaceutical Bulletin 1975, 23, 2268-2278.
23. Jiang, Y.; Ali, O. A.; Guillaume, D.; Weniger, B.; Anton, R. Triterpenoid saponins from the root of Szderoxylon cubense. Phytochemistry 1994, 35, 1013-1015.
24. Charrouf, Z.; Wieruszeski, J. M.; Fkih-Tetouani, S.; Leroy, Y.; Charrouf, M.; Fournet, B. Triterpenoid saponins from Argania spinosa. Phytochemistry 1992, 31, 2079-2086.
25. Lavaud, C.; Massiot, G.; Becchi, M.; Misra, G.; Nigam, S. K. Saponins from three species of Mimusops. Phytochemistry 1996, 41, 887-893.
26. Sun, H.; Fang, W. S.; Wang, W. Z.; Hu, C. Structure-activity relationships of oleanane- and ursane-type triterpenoids. Botanical Studies 2006, 47, 339-368.
27. Chaturvedula, V. S.; Schilling, J. K.; Miller, J. S.; Andriantsiferana, R.; Rasamison, V. E.; Kingston, D. G. New cytotoxic oleanane saponins from the infructescences of Polyscias amplifolia from the Madagascar rainforest. Planta Medica 2003, 69, 440-444.
28. Konoshima, T.; Yasuda, I.; Kashiwada, Y.; Cosentino, L. M.; Lee, K. H. Anti-AIDS agents, 21 triterpenoid saponins as Anti-HIV principles from fruits of Gleditsia japonica and Gymnocladus chinesis, and a structure-activity correlation. Journal of Natural Products 1995, 58, 1372-1377.
29. Kinjo, J.; Yokomizo, K.; Hirakawa, T.; Shii, Y.; Nohara, T.; Uyeda, M. Anti-herpes virus activity of Fabaceous triterpenoidal saponins. Biological & Pharmaceutical Bulletin 2000, 23, 887-889.
30. Matsuda, H.; Li, Y.; Murakami, T.; Yamahara, J.; Yoshikawa, M. Structure-related inhibitory activity of oleanolic acid glycosides on gastric emptying in mice. Bioorganic & Medicinal Chemistry 1999, 7, 323-327.
31. Olennikov, D. N.; Chirikova, N. K.; Tankhaeva, L. M. Chemical study of Lophanthus chinensis. Chemistry of natural compounds 2010, 46, 301-302.
32. Lee, S. S.; Wang, J. S.; Chen, K. C. S. Chemical constituents from the roots of Zizyphus jujuba Mill. var. spinosa. Journal of the Chinese Chemical Society 1995, 42, 77-82.
33. Vidal-Ollivier, E.; Elias, R.; Faure, F.; Babadjamian, A.; Crespin, F.; Balansard, G.; Boudon, G. Flavonol glycosides from Calendula officinalis flowers. Planta Medica 1989, 55, 73-74.
34. Kijima, H.; Ide, T.; Otsuka, H.; Takeda, Y. Alangiflavoside, a new flavonol glycoside from the leaves of Alangium premnifolium. Journal of Natural Products 1995, 58, 1753-1755.
dc.identifier.urihttp://tdr.lib.ntu.edu.tw/jspui/handle/123456789/29663-
dc.description.abstract山欖科(Sapotaceae)大約有107個屬,超過1000個種,但至今仍只有少數山欖屬(Planchonella)植物之成分有被研究。本論文為持續本研究室先前對山欖葉部之成分探討,針對其山欖葉部乙醇萃取物之極性化割的正丁醇及甲醇可溶層做進一步成分分離,利用離心式分配層析儀、SP 700樹脂、凝膠管柱層析、矽膠管柱層析和逆向管柱層析等方式進行,共計得到15個化合物,包括六個黃酮醇成分:isorhamnetin 3-O-robinobioside (1)、3-O-rutinoside (2)、3-O-neohesperidoside (11) and 3-O-(2,6-di-O-α-rhamnosyl)-β-galactopyranoside (14)、quercetin 3-O-rutinoside (12) 及typhaneoside (13);一個三萜成分:ursolic acid (3);和八個三萜類皂苷即Mi-saponins A-C (15、6和4)、3'-O-β-apiofuranosylarganin F (5)、3-O-glucopyranosyl- protobassic acid (7)、isoarganin F (8)、3'-O-de-β-D-apiofuranosylisoarganin F (9)和arganin F (10)。其結構解析係藉由一維TOCSY與二維NMR技術之光譜分析而確認,其中化合物5、8和9為新的三萜類配醣體。zh_TW
dc.description.abstractThe Sapotaceae family contains about 107 genera and more than 1000 species. Up to now, only a few species of the Planchonella genus have been investigated phytochemically. In a continuation of our recent study on the EtOH extract of Planchonella obovata leaf, this thesis focused on chemical investigation of the n-BuOH and MeOH soluble fractions. Repeated chromatography through centrifugal partition chromatography, SP 700 resin, Sephadex LH-20, silica gel, and reversed-phase C-18 column (Lobar and semi-preparative HPLC) yielded fifteen compounds (1~15). They are six flavonols, i.e., isorhamnetin 3-O-robinobioside (1), 3-O-rutinoside (2), 3-O-neohesperidoside (11), 3-O-(2,6-di-O-α-rhamnosyl)-β-galactopyranoside (14), quercetin 3-O-rutinoside (12) and typhaneoside (13); one triterpene, i.e. ursolic acid (3); and eight triterpenoid saponins, i.e. Mi-saponins A-C (15, 6 and 4), 3'-O-β- apiofuranosylarganin F (5), 3-O-glucopyranosylprotobassic acid (7), isoarganin F (8), 3'-O-de-β-D-apiofuranosylisoarganin F (9) and arganin F (10). The structures of these compounds were elucidated based on elaborate spectroscopic analysis, especially using 1D-TOCSY and 2D-NMR. Among them, compounds 5, 8 and 9 are found to be new saponins.en
dc.description.provenanceMade available in DSpace on 2021-06-13T01:14:03Z (GMT). No. of bitstreams: 1
ntu-100-R98423003-1.pdf: 9694006 bytes, checksum: 5cb53ed70b546c0d9acf5976a89aa635 (MD5)
Previous issue date: 2011
en
dc.description.tableofcontents口詴委員會審定書 ..........................................i
誌謝 ................................................... ii
中文摘要 ...................................... I
英文摘要(Abstract) ............................. II
總目錄 ........................ III
表目錄 ........................ IV
圖目錄 ................... V
流程圖目錄 ............................. VIII
詞彙縮寫(Glossary of Abbreviations).......... IX
第一章 緒論 ............................................. 1
1.1 研究目的 ................. 1
1.2 植物簡介 ................... 1
1.3 Planchonella屬植物成分之相關研究 ................ 3
第二章 實驗結果與討論.............................. 6
2.1 黃酮類成分及三萜類成分之結構解析 ............... 6
2.1.1 Flavan-3-ol成分1, 2, 11-14之結構解析 ......... 8
2.1.1.1 Isorhamnetin 3-O-robinobioside (1)之結構解析 ..... 8
2.1.1.2 Isorhamnetin 3-O-rutinoside (2)之結構解析 .. 10
2.1.1.3 Isorhamnetin 3-O-neohesperidoside (11)之結構解析 . 12
2.1.1.4 Quercetin 3-O-rutinoside (12)之結構解析 ..... 14
2.1.1.5 Typhaneoside (13)之結構解析 .......... 16
2.1.1.6 Isorhamnetin 3-O-(2,6-di-O-α-rhamnosyl)-β-galactopyranoside (14)之結構解析 ...................... 18
2.1.2 Ursolic acid (3)之結構解析 ...................... 20
2.1.3 Protobassic acid glycosides 4-10, 15及衍生物4a之結構解析 .......... 22
2.1.3.1 Mi-saponin C (4)及Mi-saponin C peracetate (4a)之結構解析 ........ 23
2.1.3.2 3'-O-β-Apiofuranosylarganin F (5)之結構解析 .. 27
2.1.3.3 Mi-saponin B (6)之結構解析 ........ 31
2.1.3.4 3-O-β-D-Glucopyranosylprotobassic acid (7)之結構解析 ................ 35
2.1.3.5 Isoarganin F (8)之結構解析 ......... 37
2.1.3.6 3'-O-De-β-D-apiofuranosylisoarganin F (9)之結構解析 ................. 41
2.1.3.7 Arganin F (10)之結構解析 .............. 45
2.1.3.8 Mi-saponin A (15)之結構解析 ............. 49
2.2 結論 .................................................... 53
第三章 實驗部分 ......................................... 54
3.1 儀器與器材 ...................................... 54
3.1.1 理化性質測定儀器 ............... 54
3.1.2 成分分離之儀器與器材 ........ 54
3.1.3 詴藥及溶劑 ............................. 55
3.1.4 薄層層析展開系統 ................ 56
3.2 山欖葉部成分萃取與分離 ....................... 56
3.2.1 甲醇可溶層之成分分離 (A) ............. 59
3.2.2 甲醇可溶層之成分分離 (B)............ 60
3.2.3 正丁醇層之成分分離 .......... 61
3.3 各化合物之物理數據 ....................... 63
參考文獻 .................................. 69
dc.language.isozh-TW
dc.title山欖葉部之成份研究 (II)zh_TW
dc.titleChemical investigation of the leaves of Planchonella obovata (R. Br.) Pierre (II)en
dc.typeThesis
dc.date.schoolyear99-2
dc.description.degree碩士
dc.contributor.oralexamcommittee陳繼明,陳春雄(Chung-Hsiung Chen),林雲蓮(Yun-Lian Lin)
dc.subject.keyword山欖科,山欖,三&#33820,類皂&#33527,zh_TW
dc.subject.keywordSapotaceae,Planchonella obovata,triterpenoid saponins,en
dc.relation.page162
dc.rights.note有償授權
dc.date.accepted2011-08-03
dc.contributor.author-college醫學院zh_TW
dc.contributor.author-dept藥學研究所zh_TW
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