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研究生: 黃家展
Hwang, Chia-Chan
論文名稱: 台灣繡線菊莖部之成分研究
The Constituents of the Stems of Spiraea formosana
指導教授: 吳天賞
Wu, Tian-Shung
學位類別: 碩士
Master
系所名稱: 理學院 - 化學系
Department of Chemistry
論文出版年: 2003
畢業學年度: 91
語文別: 中文
論文頁數: 121
中文關鍵詞: 單萜類三萜類二萜類繡線菊屬台灣繡線菊生物鹼烏頭屬
外文關鍵詞: Aconitum, Spiraea, Rosaceae, formosana
相關次數: 點閱:218下載:2
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  •   將乾燥的台灣繡線菊莖部 8.60 kg以乙醇萃取六次過濾,並於減壓濃縮除去溶劑後,得到萃取物,將此萃取物分別以氯仿、正丁醇與水進行多次分配萃取,所得之各分配層分別以管柱層析、薄層層析、再結晶方法及高效液相層析法處理,共得到40個化合物,其中39個化合物經光譜分析與文獻比對光譜資料後,確定其化學結構為:agrimonolide, 3-O-β-D-glucosyl-4’,5-dihydroxystilbene, 3,4’,5-trihydro-xystilbene, p-hydroxybenzoic acid, methyl vanillate, p-hydroxybenz-aldehyde, veratric acid, syringic acid, nonadecyl ferulate, p-hydroxy-cinnamaldehyde, methyl ferulate, ethyl p-hydroxy-trans-cinnamate, ethyl ferulate, bakuchiol, (-)-isolariciresinol-3a-O-β-D-glucopyranoside,aurantiamide acetate, N,N-dimethyladenine, methyl quinate, (+)-5,7-dihydroxy-2-(3’,4’-methylenedioxyphenyl)chroman-4-one, β-sitosterone,sitgmasterol與β-sitosterol混合物, 3-O-β-D-glucosyl-p-vanillic acid,vanillic acid, uridine, nanodecyl-3-(4-hydroxy-phenyl)propioate, β-sitosterol, glutinol, β-amyrin, quercetin-3-O-β-D-glucopyranoside,quercetin, quercetin-3-O-β-D-galactopyranoside, kaempferol-3-O-β-D-glucopyranoside, p-coumaric acid, β-sitosteryl glucoside 。其中,spiraeaine A、spiraformin-A~D等5個為天然界首次發現之新化合物。

      The dried stems of Spiraea formosana (8.60 Kg) were extractdwith EtOH, and then concentrated under reduce pressure to give darkbrown crude extract 1.02 kg. The crude extract was partitioned bet-ween H2O and CHCl3, and then with n-BuOH. Forty compounds were isolated from each partitioned fraction of this plant by usuallychromatographic methods. The structure of thirty-nine compounds were determined by spectral analysis and chemical transformation.
      They are agrimonolide, 3-O-β-D-glucosyl-4’,5-dihydroxystil-bene, 3,4’,5-trihydroxystilbene, p-hydroxybenzoic acid, methyl vanill-ate, p-hydroxybenzaldehyde, veratric acid, syringic acid, nonadecyl ferulate, p-hydroxycinnamaldehyde, methyl ferulate, ethyl p-hydroxy-trans-cinnamate, ethyl ferulate, bakuchiol, (-)-isolariciresinol-3a-O-β-D-glucopyranoside, aurantiamide acetate, N,N-dimethyladenine, me-thyl quinate, (+)-5,7-dihydroxy-2-(3’,4’-methylenedioxyphenyl)chro-man-4-one, β-sitosterone, mixture sitgmasterol and β-sitosterol, 3-O-β-D-glucosyl-p-vanillic acid, vanillic acid, uridine, nanodecyl-3-(4-hydroxyphenyl)propioate, β-sitosterol, glutinol, β-amyrin, quercetin-3-O-β-D-glucopyranoside, quercetin, quercetin-3-O-β-D-galactopyrano-side, kaempferol-3-O-β-D-glucopyranoside, p-coumaric acid, β-sitoster-yl glucoside. Among them, new compounds, spiraeaine A and spira-formin-A~D were isolated from natural source for the first time.

    英文摘要 I 中文摘要 II 第一章 緒論 1   第一節   前言 1   第二節  植物形態 2 第二章 繡線菊屬成分研究回顧 3   第一節  藥理與藥效 3   第二節  繡線菊屬之成分回顧 4   第三章  萃取與分離 19 第四章 構造研究 28   第一節  化合物Spiraeaine A (1) 之構造研究 28   第二節  化合物Agrimonolide (2)之構造研究 34   第三節  化合物Spiraformin-A (3)之構造研究 39   第四節  化合物Spiraformin-B (4)之構造研究 44   第五節  化合物Spiraformin-C (5)之構造研究 48   第六節  化合物Spiraformin-D (6)之構造研究 52   第七節  3-O-β-D-Glucosyl-4’,5-dihydroxystilbene (7)之構造研究 56   第八節  3,4’,5-Trihydroxystilbene (8)之構造研究 61   第九節  Bakuchiol (19)之構造研究 63   第十節  (-)-Isolariciresinol 3a-O-β-D-glucopyranoside (20)之構造研究 67   第十一節 Quercetin -3-O-β-D-glucopyranoside (28) 之構造研究 72   第十二節 Quercetin (64) 之構造研究 77   第十三節 Kaempferol-3-O-β-D-glucopyranoside (63) 之構造研究 79   第十四節 (+)-5,7-Dihydroxy-2-(3’,4’-methylenedioxyphenyl)chroman-4-one (24) 之構造研究 82   第十五節 其他已知化合物之構造研究 84 第五章 結論 85 第六章 實驗部分 86   第一節  本實驗所使用之儀器 86   第二節  萃取與分離 87   第三節  化合物 (3-1) 之methylation 反應 91 光譜數據整理 92 參考文獻 117

    1. 中國科學院中國植物志編輯委員會, “中國植物志” 第三十六卷, 9-66
    科學出版社, 北京 (1974)

    2. 陳玉峰, “台灣植被誌”, 亞高山冷杉林帶與高地草原(下) 初版 第3卷, 477-479頁, 前衛出版社, 台北 (1998)

    3. Goto, G., Sasaki, K., Sakahe, N., Hirata, Y., “The alkaloids obtained from spiraea japonica L. fil” Tetrahedron Lett., 1369-1373 (1968)

    4. Hao, X. J, Nie, J. L., Sun, H., Gu, Z. J., “The chemotaxonomy of spiraea japonica complex” Yunnan Zhiwu YanJiu, 19, 297-303 (1997)

    5. Shen, Z. Q., Chen, Z. H., Li, L., Lei, W. Y., Hao, X. J., “Antiplatelet and antithrombotic effects of the diterpene spiramine Q from spiraea japonica var. incisa” Planta Med., 66, 287-289 (2000)

    6. So, H. S., Park, R., Oh, H. M., Pae, H. O., Lee, J. H., Chai, K. Y., Chung, S. Y., Chung, H. T., “The methanol extact of spiraea prunifolia var. simpliciflora root inhibits the generation of nitric oxide and superoxide in RAW 264.7 cells” J. Ethnopharmacol., 68, 209-217 (1999)

    7. Lin, L. C., Chou, C. J., Yang, L. M., “Chemical constituents from the fruit of spiraea formosana” Chin. Pharm. J., 51, 299-305(1999)

    8. Chou, C. J., Wang, C. B., Lin, L. C., “Triterpenoids and some other constituents from spiraea formosana” J. Chin. Chem. Soc., 24, 195-198 (1977)

    9. 行政院農業委員會特有生物研究保育中心;網址:http//:www. tesri. gov. tw/ knowthem/ c10. htn.

    10. Carl, E., Hans, E. C., Walter, H., “Esters and glucosides of sterols from seeds as neoplasm inhibitors” PCT Int. Appl. 91, 139 (1991)
    [Chem. Abstr. 115, 287165j (1991)]

    11.Hao, X. J., Hong, X., Yang, X. S., Zhao, B. T., “Diterpene alkaloids from roots spiraea japonica” Phytochemistry, 38, 545-547 (1995)

    12. So, H. S., Park, R., Oh, H. M., Chai, K. Y., Lee, J. H., Chung, H. T., “Enhancement of nitric oxide synthesis by the aqueous extract of spiraea prunifolla var. simpliciflora’s root in RAW 264.7 cells” Immunopharmacol. Immunotoxicol., 21, 343-355 (1999)

    13. Li, M., Du, X. B., Shen, Y. M., “New diterpenoid alkaloids from spiraea fritschiana var. parvifolia”Chin. Chem. Lett., 10, 827-830 (1999)

    14. Wang, B. G., Li, L., Yang, X. S., Chen, Z. H., Hao, X. J., “Three new diterpene alkaloids from spiraea japonica” Heterocycles, 53, 1343-1350 (2000)

    15. Hao, X. J., Zhou, J., Fuji, K., Node, M., “The chemical structures of spiramine J,k,L and M” Acta. Botanica. Yunnanica, 14, 314-318 (1992)

    16. Node, M. B., Hao, X. J., Zhou, J., “Spiraea A, B, C and D, a new diterpene alkaloids from spiraea japonica var. accuminata Franch. ” Heterocycles, 30, 635-643 (1990)

    17. Sun, F., Ling, X. T., Yu, D., “The structures of spirasine V and spirasine VI” Tetrahedron. Lett., 27, 275-278 (1986)

    18. Sun, F., Ling, X. T., Yu, D. Q., “Four new C20-diterpene alkaloids, spirasine I, spirasine II, spirasine VII, and spirasine VIII, from spiraeajaponica ” Heterocycles, 24, 2105-2110 (1986)

    19.Sun, F., Ling, X. T., Yu, D. Q., “A new C20-diterpene alkaloids, spirasine III and the interconversion of oxazolidine ring” Heterocycles, 26, 19-22(1987)

    20. Nie, J. L., Hao, X. J., “Diterpene alkaloids from spiraea japonica var. acuta.” Acta. Botanica. Yunnanica, 19, 429-432 (1997)

    21. Wang, B. G., Liu, B., Zuo, G. Y., Hao, X. J., “A new minor diterpene alkaloids from spiraea japonica var. acuta.” Acta. Botanica. Yunnanica, 22, 209-213 (2000)

    22. Hao, X. J., Nie, J. L., “Diterpene from spiraea japonica” Phytochemistry, 48, 1213-1215 (1998)

    23. Shen, Y. M., He, H. P., Zhang, Y. S., Wang, B. G., Hao, X. J., “Spiramide, a new diterpene amide from the roots of spiraea japonica var. acuta” Chin. Chem. Lett., 11,789-792 (2000)

    24. He, H. P.,Shen, Y. M., Zhang, J. X., Zuo, G. Y., Hao, X. J., “New diterpene alkaloids from the roots of spiraea japonica” J. Nat. Prod., 64, 379-380 (2001)

    25. Hao, X. J., Zhou, J., Chen, S. Y., Fuji, K., Node, M., “New diterpene alkaloids from spiraea japonica var. acuminata” Acta. Botanica. Yunnanica, 13, 452-454 (1991)

    26. Lei, N. J., Hao, X. J., “Spiramilactone B, a new diterpenoid from spiraea japonica var. stellaris” Acta. Botanica. Yunnanic., 18, 226-228 (1996)

    27. Hao, X. J., Node, M., Zhou, J., Chen, S. Y., Fuji, K., “The chemical structures of spiramine H, I, and O ” Acta. Botanica. Yunnanica, 16, 301-304 (1994)

    28. Nie, J. L., Hao, X. J., Li, L., “Chemical constituents of spiraea japonica var. acuminata” Acta. Botanica. Yunnanica, 19, 327-330 (1997)

    29. Zuo G. Y., He, H. P., Hong, X., Zhu, W. M., Yang, X. H., Hao, X. J., “New spiramines from spiraea japonica var. ovalifolla ” Heterocycles, 55, 487-493 (2001)

    30. Yang, X. S., Hao, X. J., “The diterpenoid from alkaloids spiraea japonica var. glabra ” Acta. Botanica. Yunnanica, 15,421-423 (1993)

    31. Chumbalov, T. K., Pashinina, L. T., Storozhenko, N. D., “Flavones and their 5-glycosides from spiraea hypericifolia” Chem. Nat. Compd., 11, 440-441 (1975)

    32. Oh, H. C., Oh, G. S., Seo, W. G., Pae, H. O., Chai, K. Y., Kwon, T. O., Lee, H. T., Lee, H. S., “Prunioside A: a new terpene glycoside from spiraea prunifolia” J. Nat. prod. 64, 942-944 (2001)

    33. Yoshio, T., Komami, F. M., Maya, T. B., Tetsuro, S., Tetsuro, F., Teruyoshi, I., “Monoterpene glucosides having a cross conjugated dienone system from spiraea cantoniensis”Phytochemistry, 29, 1591-1593 (1990)

    34. Arakawa, H., Torimoto, N., Masui, Y., “Die absolute konfiguration des (-)-β-tetralols und des agrimonolides” Tetrahedron Lett., 38, 4115-4117 (1968)

    35. Wang, M., Li, J., Rangarajan, M., Shao, Y., Lavoce, E. J., Huang, T. C., “Antioxidative phenolic compounds from sage (salvia officinalis)”
    J. Agric. Food. Chem., 46, 4869-4873 (1998)

    36. Nyemba, A. M., Mpondo, T. N., Kimbu, S. F., Connolly, J. D., “Stilbene glycosides from guibourtia tessmanii” Phytochemistry, 39, 895-898 (1995)

    37. Mehta, G., Nayak, U. R., Sukh, D., “Meroterpenoids –Ipsoralea corylifolia linn. Bakuchiol, a novel monoterpene phenol”Tetrahedron, 29, 1119-1125 (1973)

    38. Lundgren, L. N., Theander, O., “Cis-and trans-dihydroquercetin glucosides from needles of pinus sylvestris” Phytochemistry, 27, 829-832 (1988)

    39. Ferreira, E. O., Dias, D. A., “A methylenedioxyflavonol from aerial part of blutaparon portulacoides” Phytochemistry, 53, 145-147 (2000)

    40. Machida, K., Kikuchi, M., “Norisoprenoids from viburnum dilatatum”
    Phytochemistry, 41, 1333-1336 (1996)

    41. Wu, T. S., Ou, L. F., Teng, C. M., “Aristolochic acids, aristolactam alkaloids and amides from aristolochia kankauensis”Phytochemistry, 36, 1063-1068 (1994)

    42. Wu, T. S., Yeh, J. H., Wu, P. L., “The heartwood constituents of tetradium glabrifolium”Phytochemistry, 40, 121-124(1995)

    43. 林福文, “雲南丹參、三葉鼠尾及厚殼桂之成分與生物活性研究”, 成功大學, 博士論文, 103 (2002)

    44. Barik, B. R., Kundu, A. K., “Two phenolic constituents from alpinia galanga rhizomes” Phytochemistry, 26, 2126-2127 (1987)

    45. Machida, K., Kikuchi, M., “Norisoprenoids from viburnum dilatatum” Phytochemistry, 41, 1333-1336 (1995)

    46. Talapatra, S. K., Mukhopadhyay, S. K., Talapatra, B., “Minor coumarins of boenninghausenia albiflora” Phytochemical Reports., 836-837 (1974)

    47. Bhadari, S. P. S., Mishra, A., Roy, R., Garg, H. S., “Koelzioside,
    an iridoid diglycoside from scrophularia koelzii”Phytochemistry,31,
    689-691 (1992)

    48. Paknikar, S. K., Kirtany, J. K., Naik, C. G., “Communications”Indian. J. Chem., 13, 1234-1236 (1975)

    49. Wu, T. S., Chang, F. C., Wu, P. L., Kuoh, C. S., “Constituents of leaves of tetradium glabrifolium” J. Chin. Chem. Soc.,42, 929-934 (1995)

    50. 石麗仙, “中草藥之活性成分研究” 中國醫藥學院, 博士論文, 62
    (2001)

    51. Wu, T. S., Chan, Y. Y., “Constituents of leaves of uncaria hirsute
    haviland”J. Chin. Chem. Soc., 41, 209-212 (1994)

    52. Ayiyo, S. K., Maksut, C. K., Takashi, H. K., “Hydroxybenzoic acids
    from boreava orientalis”Phytochemistry, 40, 257-261 (1995)

    53. 石麗仙, “中草藥之活性成分研究” 中國醫藥學院, 博士論文, 48 (2001)

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