華中五味子種子活性木質酚素成分之研究

本論文研究華中五味子(Schisandra sphenanthera Rehd. et Wils)之種子化學成分，從酒精萃取物中分離鑑定出七個新的木質酚素(1-7)和十一個已知化合物(8-18)。新發現的化合物schisphenin B (1)屬於 6,7-seco lignan、schisphentetralone A (2) 屬於aryltetralone-type lignan、schisphenins C-G (3-7)為 C18-dibenzocyclooctadiene lignans 。另外十一個已知化合物中有九個為木質酚素化合物，分別是 pre-gomisin (8)、meso-dihydroguaiaretic acid (9)、veraguensin (10)、(－)-8-epi-aristoligone (11)、benzoylgomisin P (12)、benzoylgomisin U (13)、gomisin F (14)、(+)-gomisin K3 (15)、schisantherin D (16) ，及兩個三萜類化合物 kadsuric acid (17) 和 coccinic acid (18)。以上化合物的結構是利用核磁共振圖譜1D-NMR (1H-NMR、13C-NMR), 及 2D-NMR (COSY、HMQC、HMBC、NOESY) 及各種物理數據分析，包括旋光度、紅外線、紫外線、CD光譜及高解析電灑式質譜儀，並參考相關文獻而確認。立體結構方面，化合物3-7 的biphenyl moiety部分為S-configuration且cyclooctadiene ring部分均為twist-boat-chair (TBC)構型。最後將所分得的十八個化合物進行生物活性檢測，利用reporter gene assay測試抗肝纖維化活性，發現化合物1、2、4、11、13、14、18對大鼠肝纖維化細胞有抑制作用，其中以化合物11效果最強。另外抗氧化試驗中發現化合物9有不錯自由基捕捉能力，但仍較vitamin C差。

關鍵字

華中五味子；種子；木質酚素； aryltetralone ； dibenzocyclooctadiene

並列摘要

This research investigated the chemical constituents of the seeds from the medicinal plant Schisandra sphenanthera. From the ethanol extract, seven new oxygenated lignans (1-7), and eleven known compounds (8-18) were isolated. New components could be classified into 6,7-seco dibenzocyclooctadiene type lignan, schisphenin B (1), aryltetralone type lignan, schisphentetralone A (2), and C18-dibenzocyclooctadiene lignans, schisphenins C-G (3-7). The known compounds were identified as nine lignans： pre-gomisin (8), meso-dihydroguaiaretic acid (9), veraguensin (10), (－)-8epi-aristoligone (11), benzoylgomisin P (12), benzoylgomisin U (13), gomisin F (14), (＋)-gomisin K3 (15), and schisantherin D (16), together with two triterpenoids, kadsuric acid (17) and coccinic acid (18). The structural elucidations of these compounds were determined on the basis of spectroscopic analyses of 1D-NMR (1H and 13C-NMR), 2D-NMR (COSY, HMQC, HMBC, NOESY) techniques, physical methods including optical rotation, IR, UV, CD, HRESIMS, as well as by comparison of the published data. The CD results showed that the biphenyl groups of new compounds 3-7 were all S-configuration and the analyses of NOESY correlations revealed that the octadiene moieties of them were twist-boat-chair conformation. Biological activities of all isolated components were evaluated as well. The reporter gene assay was used to measure anti-liver fibrosis effect in this study. Compounds 1, 2, 4, 11, 13, 14, 18 were regarded as better anti-inflammatory activity substances on HSC-T6 test. Among them, 11 is the most potential one because its activity is better than the positive control, silymarin. The DPPH free-radical scavenging experiment indicated that compound 9 exhibited good effect at 0.006 M (scarvenging activity 55.4%), but it was worse than vitamin C at 0.0057 M (scarvenging activity 95.8%).

並列關鍵字

Schisandra sphenanthera ； seeds ； ignan ； aryltetralone ； dibenzocyclooctadiene

參考文獻

50. Shen, Y. C.; Liaw, C. C.; Cheng, Y. B.; Ahmed, A. F.; Lai, M. C.; Liou, S. S.; Wu, T. S.; Kuo, Y. H.; Lin, Y. C. C18-dibenzocyclooctadiene lignans from Kadsura philippinensis. Journal of Natural Products 2006, 69, 963-966.

53. Shen, Y. C.; Cheng, Y. B.; Lan, T. W.; Liaw, C. C.; Liou, S. S.; Kuo, Y. H.; Khalil, A. T. Kadsuphilols A-H, oxygenated lignans from Kadsura philippinensis. Journal of Natural Products 2007, 70, 1139-1145.

57. Shen, Y. C.; Lin, Y. C.; Cheng, Y. B.; Chang, C. J.; Lan, T. W.; Liou, S. S.; Chien, C. T.; Liaw, C. C.; Khalil, A. T. New oxygenated lignans from Kadsura philippinensis. Helvetica Chimica Acta 2008, 91, 483-494.

65. Cheng, Y. B.; Cheng, M. T.; Lo, I. W.; Ho, C. J.; Kuo, Y. C.; Chien, C. T.; Chen, S. Y.; Liou, S. S.; Kuo, Y. H.; Shen, Y. C. Oxygenated lignans from the fruits of Schisandra arisanensis. Journal of Natural Products 2009, 72, 1663-1668

58. Gao, X. M.; Pu, J. X.; Huang, S. X.; Yang, L. M.; Huang, H.; Xiao, W. L.; Zheng, Y. T.; Sun, H. D. Lignans from Kadsura angustifolia. Journal of Natural Products 2008, 71, 558-563.

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華中五味子種子活性木質酚素成分之研究

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