近幾年來，全世界對於海洋無脊椎動物進行許多研究，而在軟珊瑚發現許多化合物(如：sesquiterpenoids、diterpenoids、steroids等)，具有抑制癌細胞生長及抗發炎等效果。近幾年在天然物的研究指出，從軟珊瑚(Cespitularia sp.)成份的verticillene骨架與部份紅豆杉雙萜類(taxoids)成份有相當類似的化學結構，所以研究紅豆杉的化學成份，可以間接了解軟珊瑚化學結構的關連性。
為了尋找實用與豐富的紅豆杉雙萜類成份，以研究其結構關連性，選擇在高雄縣六龜林區所採集的台灣產南洋10年生紅豆杉T. sumatrana的枝葉為材料，由丙酮萃取，再經色層分析法，純化出雙萜類成分，並進行分析。本次實驗，共分離出4個新的化合物1~4，其化學結構分析主要採用核磁共振磁譜技術，以及其他物理方法，如：質譜(ESIMS、HRESIMS)、紅外線光譜(IR)、紫外線光譜(UV)以及旋光度之測量，再加上比對相關文獻之後所建立，化合物1是taxoid 6/10/6 ring骨架，而化合物2~4是verticillene骨架，但是取代基不同。

In recent years, many marine invertebrates were studied in the world, and many compounds were discovered from soft corals (for example: sesquiterpenoids, diterpenoids, steroids and so on). From the previous studies on marine nature products, we found that verticillenes of soft corals have similar structures to taxoid diterpenoids of Taxus sp. This prompted us to study Taxus sp., thus we may indirectly understand the correlation of verticillienes of Taxus with verticilliene diterpenes of the soft corals.
In order to discover new taxoid derivatives, the twigs and leaves of the Formosan T. sumatrana growing in Taiwan were investigated. Chromatographic separations of acetone extract of the leaves and twigs of this species yielded taxoid-enrich extracts. Fractionation of T. sumatrana has resulted in the isolation of four new compounds 1- 4. All structures were established primarily on the basis of 1D and 2D NMR experiments and other physical methods, such as mass spectroscopy, infrared, ultraviolet and optical rotation. The compound 1 is a taxoid 6/10/6 ring skeleton. The compounds, 2~4, are the verticillene skeleton, but the functional groups are different.

目錄
頁次
壹、緒論
一、前言 …………………………………………………………… 6
二、研究動機與目的 ……………………………………………… 8
三、紅豆杉簡介與文獻回顧
A.紅豆杉簡介 …………………………………………………… 9
B.紅豆杉文獻回顧 ……………………………………………… 11
四、軟珊瑚簡介與文獻回顧
A.軟珊瑚簡介 …………………………………………………… 19
B.軟珊瑚文獻回顧 ……………………………………………… 20
貳、材料與研究方法
一、樣品的採集……………………………………………………… 24
二、矽膠與溶劑……………………………………………………… 24
三、分離方法之簡述………………………………………………… 25
四、儀器……………………………………………………………… 31
五、結構鑑定………………………………………………………… 32
參、結果與討論
一、化合物1 (T1-14-4-2-3)之結構鑑定 ………………………… 33
二、化合物2 (T1-28-6a-4)之結構鑑定 ………………………… 42
三、化合物3 (T1-28-6b-2)之結構鑑定 ………………………… 51
四、化合物4 (T2-17-m1-2-7)之結構鑑定………………………… 62
五、紅豆杉之已知verticillene骨架化合物 ………………………… 69
六、化合物的水解反應 ……………………………………………… 70
七、雙萜類化合物taxoid與cespitularin結構上的比較 …………… 72
肆、結論 ………………………………………………………………… 76
伍、參考文獻……………………………………………………………… 77

1. Duh, C.Y., El-Gamal, A. A. H., Wang, S.K., Dai C.F., “Novel terpenoids from the Formosan soft coral Cespitularia hypotentaculata”, J. Nat. Prod., 2002, 65 1429-1433.
2. Shen, Y.C., Hsu, S.M., Lin, Y.S., Cheng, K.C., Chien, C.T., Chou, C.H., and Cheng, Y.B., “New bicyclic taxane diterpenoids from Taxus sumatrana”, Chem. Pharm. Bull., 2005, 53, 808-810.
3. Wani, M. C., Taylor, H. L., Wall, M. C., Coggon. P., McPhail, A. T., “Plant antitumor agents. VI. The isolation and structure of taxol, anovel antileukemic and antitumor agent from Taxus brevifolia” , J. Am. Chem. Soc.,1971, 93, 2325-2327.
4. Lindel, T., Jensen, P. R., Fenical, W.; Long, B. H.; Casazza, A. M.; Carboni, J., Fairchild, C. R., “Eleutherobin, a new cytotoxin that mimics paclitaxel (Taxol) by stabilizing microtubules”, J. Am. Chem. Soc., 1997, 119, 8744-8745.
5. 中國醫學科學院藥物研究所，“中草藥現代研究 第三卷”，pp. 305-360,北京醫科大學中國協和醫科大學聯合出版社。
6. 甘偉松，“藥用植物學”，pp. 140-141，國立中國醫藥研究所出版。
7. Shen, Y.C., Cheng, K.C., Lin, Y.C., Cheng, Y.B., Khalil, A. T., Guh, J.H., Chien, C.T., Teng, C.M., and Chang, Y.T., “Three new taxane diterpenoids from Taxus sumatrana”, J. Nat. Prod., 2005, 68, 90-93.
8. Shen, Y.C., Ko, C.L., Cheng, Y.b., Chiang, M. Y., and Khalil, A. T., “New regio- and stereoselective O-deacetylated and epoxy products of taxanes isolated from Taxus mairei”, J. Nat. Prod., 2004, 67, 2136-2140.
9. Shi, Q.W., Zhao, Y.M., Si, X.T., Li, Z.P., Yamada, T., and Kiyota, H., “1-Deoxypaclitaxel and abeo-taxoids from the seeds of Taxus mairei ”, J. Nat. Prod., 2006, 69, 280-283.
10. Shi, Q.W., Li, Z.P., Zhao, D., Gu, J.S. and Kiyota, H., “Isolation and structure revision of 10-deacetyltaxinine from the seeds of the Chinese yew, Taxus mairei”, Nat. Prod. Res., 2006, 20, 47–51.
11. Shi, Q.W., Li, Z.P., Wang, C.L., Zhang, M.L., CHOONY, N. and KIYOTA, H., “New taxanes from the seeds of Taxus mairei” ,J. Asian Nat. Prod. Res., 2006, 8, 431–437.
12. Wang F.S., Peng, L.Y., Zhao, Y., Xu, G., Zhao, Q.-S., and Sun, H.D., “Three new oxetane-ring-containing taxoids from Taxus chinensis”, J. Nat. Prod., 2004, 67, 905-907.
13. Zhao, Y., Wang, F.S., Peng, L.Y., Li, X.L., Xu, G., Luo, X.X., Lu, Y., Wu L., Zheng, Q.T., and Zhao, Q.S., “Taxoids from Taxus chinensis”, J. Nat. Prod., 2006, 69, 1813-1815.
14. Xia, Z.H., Peng, L.Y., Zhao, Y., Xu, G., Zhao, Q.S., and Sun H.D., “Two new taxoids from Taxus chinensis”, Chem. Biodiv., 2005, 2, 1316-1319.
15. Shi, Q.W., Lederman, Z., Sauriol, F., McCollum, R. S., and Zamir, L. O., “A yew in Israel, new taxane derivatives”, J. Nat. Prod., 2005, 68, 90-93.
16. Shi, Q.W., Sauriol, F., Lesimple, A. and Zamir, L. O., “First three examples of taxane-derived di-propellanes in Taxus canadensis needles”, Chem. Commun. , 2004, 5, 544-545.
17. Shi, Q.W., Ji, X., Lesimple, A., Sauriol, F., Zamir, L. O., “Taxanes with C-5-amino-side chains from the needles of Taxus canadensis”, Phytochemistry, 2004, 65, 3097–3106.
18. Shi Q.W., Sauriol, F., Park, Y., Smith Jr., V. H., Lord, G. and Zamir, L. O., “First example of conformational exchange in a natural taxane enolate”, Magn. Reson. Chem., 2005, 43, 798–804.
19. Shi, Q.W., Si, X.T., Zhao, Y.M., Su, X.H., Li, X., Zamir, L. O., Yamada, T. and Kiyota, H., “Two new alkaloidal taxoids from the needles of Taxus canadensis”, Biosci. Biotechnol. Biochem., 2006, 70, 732-736.
20. Shi, Q.W., Dong, M., Huo, C.H., Su, X.H., Li, C.F., Zhang, X.P., Wang, Y.-F. and Kiyota, H., “New 14-hydroxy-taxane and2α,20
-epoxy-11(15→1)abeotaxane from the needles of Taxus canadensis”, Biosci. Biotechnol. Biochem., 2007, 71, 1777-1780.
21. Petzke, T. L., Shi, Q.W., Sauriol, F., Mamer, O., and Zamir, L. O., “Taxanes from Rooted Cuttings of Taxus canadensis”, J. Nat. Prod. 2004, 67, 1864-1869.
22. Shen, Y.-C., Lin, Y.-S., Kuo, Y.-H., Cheng, Y.-B., “Cespitulactams A, B, and C, Three New Nitrogen-containing Diterpenes from Cespitularia taeniata May”, Tetrahedron Lett., 2005, 46, 7893-7897.
23. Shen, Y.C., Ho, C.J., Kuo, Y.H., Lin, Y.S., “Cespitulactones A and B, New Diterpenoids from Cespitularia taeniata”, Bioorganic & Medicinal Chemistry Letters, 2006, 16, 2369–2372.
24. Duh, C.Y., Li, C.H., Wang, S.K., Dai, C.F., “Diterpenoids, Norditerpenoids, and Secosteroids from the Formosan Soft Coral Cespitularia hypotentaculata”, J. Nat. Prod. 2006, 69, 1188-1192.
25. Shen, Y.C., Lin, J.J., Wu, Y.R., Chang, J.Y., Duh, C.Y., Lo, K.L., “New norditerpenoids from Cespitularia hypotentaculata”, Tetrahedron letter. 2006, 47, 6651-6655.
26. Fang, W.S., Fang, Q.C., Liang, X.T., Lu, Y., and Q.T., Zheng, “Taxachitrienes A and B, two new bicyclic taxane diterpenoids from Taxus chinensis”, Tetrahedron 1995, 51, 8483-8490.