本論文主要是在利用各種色層分析方式分離台灣產紅廬莖柳珊瑚 (Junceella juncea) 與叢羽軟珊瑚 (Cespitularia taeniata) 以及南洋紅豆杉 (Taxus sumatrana) 枝葉之乙酸乙酯萃取物並分析鑑定所含的化學成分，共計分離得到二十七個新的天然物，並檢測分離到化合物的生物活性。

在研究期間從紅蘆莖柳珊瑚中分離出三個 briarane-type的新化合物 juncenolides I-K（1-3）。由叢羽軟珊瑚中分離出十一個新化合物，包括二個 6/13 雙環結構新骨架化合物 4-5 、一個 cespitularane 類化合物 6、四個 verticillane 類化合物 7-10、一個 10, 11-seco verticillane 類化合物 11 以及三個倍半萜類化合物 12-14。從南洋紅豆杉中分離出十三個新的雙萜類化合物，包括六個 wallifoliol-type 化合物 tasumatrols R-U, W, Z（15-18, 20, 23）、四個 11(15→1), 11(10→9) diabeotaxane類化合物 tasumatrols V, Y（19, 22）以及 taiwantaxins B-C （25-26）、一個 2(3→20) abeotaxane類化合物 tasumatrol X（21）、一個 11(15→1) abeotaxane 類化合物 taiwantaxin A（24）、一個6/8/6 合環化合物 taiwantaxin D（27）。

上述所有化合物的結構均是由各種物理數據 (紅外線、質譜、紫外線、旋光值)，配合各種核磁共振圖譜，並且比對文獻上相關化合物的數據來定立的。在細胞毒殺活性方面，由國立中國醫藥研究所郭曜豪老師實驗室進行測試，從紅蘆莖柳珊瑚與叢羽軟珊瑚所得的化合物 (1-14) 對人類乳癌細胞 (MCF-7)、人類骨髓癌細胞 (Daoy) 、人類結腸癌細胞 (WiDr) 、人類子宮頸癌細胞 (Hela) 四種癌細胞株進行活性測試，發現化合物 12 與 14 具有微弱的活性。另外對南洋紅豆杉所得化合物 15-27 進行活性測試發現tasumatrol Y(22) 針對人類肝癌 (Hepa2) 具有中等毒殺活性其 ED50 為 3.5 μg/mL, taiwantaxin B (25) 則對人類前列腺癌 (PC-3) 具有不錯的毒殺活性其 IC50 為 5.02 +0.6 μg/mL (8.96 +0.34 μM)。

This dissertation mainly discussed the investigation of two different Formosan soft corals, Junceella juncea and Cespitularia taeniata, as well as twigs and needles of Taxus sumatrana (Taxaceae). Their EtOAc extracts were investigated by intensive chromatography. Twenty-seven new natural products were isolated and parts of their biological activities were studied.

Three new briarane-type natural products, Juncenolides I-K（1-3）, were isolated from Junceella juncea. In the research of soft coral Cespitularia taeniata, eleven new compounds inculding two new skeleton natural products （4-5）of 6/13 bicyclic, one cespitularane-type diterpene (6), four verticillane-type diterpenes (7-10), one 10, 11-seco verticillane-type diterpene (11), three sesquiterpenes (12-14) were purified. Chemical investigation of Taxus sumatrana (Taxaceae) resulted in isolation of thirteen new taxane diterpenes, including tasumatrols R-U, W, Z （15-18, 20, 23）, six wallifoliol-type diterpenes, tasumatrols V, Y（19, 22） and 11(15→1), 11(10→9) diabeotaxane diterpenes , taiwantaxins B-C （25-26） ; 2(3→20) abeotaxane diterpene, tasumatrol X ( 21）; one 11(15→1) abeotaxane diterpene, taiwantaxin A（24）; one 6/8/6 ring system diterpene, taiwantaxin D（27）,.

All the structures of above compounds were elucidated by physical and spectroscopic analyses (IR, mass, UV, optical rotation and NMR), and also by comparisions with the published data. Cytotoxicity and in vitro anti-inflammatory activities were measured by Dr. Kuo Yao-Haur, respectively. The biological activities of compounds 1-14 against MCF-7 (Human breast adenocarcinoma), Doay (Human medulloblastoma), WiDr (Human colon adenocarcinoma), Hela (Human cervical epitheloid carcinoma) , compounds 12 and 14 showd weak cytotoxicity. Tasumatrol Y (22) exhibited mild cytotoxicity against human liver carcinoma (Hepa2) with ED50 at 3.5 μg/mL. Taiwantaxin B (25) showed marked cytotoxicity against human prostate cancer (PC-3) cell lines with an IC50 of 5.02 +0.6 μg/mL (8.96 +0.34 μM).

第一章、台灣產軟珊瑚之天然物研究

壹、序論
一、前言 1
二、相關化合物之文獻回顧
第一節 Junceella 屬 4
第二節 Cespitularia 屬 16
三、研究動機與目的 27
四、物種型態與分類地位
1. Junceella 屬柳珊瑚的外觀與分類地位 28
2. Cespitularia 屬軟珊瑚的外觀與分類地位 30

貳、研究結果
一、紅蘆莖柳珊瑚 Junceella juncea 的成分研究
Juncenolide I (1) 之結構分析 31
Juncenolide J (2) 之結構分析 39
Juncenolide K (3) 之結構分析 46
二、叢羽軟珊瑚 Cespitularia taeniata 的成分研究
化合物 4 之結構分析 53
化合物 5 之結構分析 61
化合物 6 之結構分析 68
化合物 7 之結構分析 75
化合物 8 之結構分析 82
化合物 9 之結構分析 89
化合物 10 之結構分析 96
化合物 11 之結構分析 103
化合物 12 之結構分析 110
化合物 13 之結構分析 117
化合物 14 之結構分析 124

第二章、南洋紅豆杉之天然物研究

壹、序論
一、前言 131
二、相關化合物之文獻回顧 133
第一節 歐洲紅豆杉 134
第二節 加拿大紅豆杉 134
第三節 中國紅豆杉 137
第四節 日本紅豆杉 138
第五節 南方紅豆杉 141
第六節 南洋紅豆杉 143
三、物種型態與分類地位
紅豆杉的外觀與分類地位 145

貳、研究結果
Tasumatrol R (15) 之結構解析 147
Tasumatrol S (16) 之結構解析 155
Tasumatrol T (17) 之結構解析 163
Tasumatrol U (18) 之結構解析 170
Tasumatrol V (19) 之結構解析 177
Tasumatrol W (20) 之結構解析 184
Tasumatrol X (21) 之結構解析 191
Tasumatrol Y (22) 之結構解析 198
Tasumatrol Z (23) 之結構解析 205
Taiwantaxin A (24) 之結構解析 211
Taiwantaxin B (25) 之結構解析 219
Taiwantaxin C (26) 之結構解析 226
Taiwantaxin D (27) 之結構解析 232

第三章、結論 239

第四章、實驗程序
壹、樣品的採集及萃取分離
一、 Junceella juncea 珊瑚之採集與分離 246
二、 Cespitularia taeniata珊瑚之採集與分離 248
三、南洋紅豆杉 Taxus sumatrana 之採集與分離 250
貳、實驗儀器與材料 252
參、生物活性檢測 254

第五章、參考文獻 256

1. 管華詩, 中國海洋藥物雜誌 2000, 4, pp. 44-47.

2. http://www.biotech.org.cn 中國醫藥網

3. Su, J.; Long, K.; Pang, T.; He, C.; Jon, C. “The Structure of Methyl Isosartortuoate, a Novel Tetracyclic Tetraterpenoid from the Soft Coral Sarcophyton tortuosum” J. Am. Chem. Soc. 1986, 108, 177-178.

4. Kortmansky, J., Schwartz, G. K., “Bryostatin-1: a novel PKC inhibitor in clinical development”, Cancer Invest., 2003, 21(6), 924-936. Review.

5. Aune, G. J., Furuta, T., Pommier, Y., “ Ecteinascidin 743: a novel anticancer drug with a unique mechanism of action”, Anticancer Drugs, 2002, 13(6), 545-555. Review.

6. Miljanich, G. P., “Ziconotide: neuronal calcium channel blocker for treating severe chronic pain”, Curr. Med. Chem., 2004, 11(23), 3029-3040. Review.

7. Luo, Y., Long, K., Fang, Z., “Studies of the chemical constituents of the Chinese gorgonian (III)-isolation and identification of a new polyacetoxy chlorine-contain ing diterpene lactone (praelolide)”, Zhongshan Daxue Xuebao, Ziran Kexueban, 1983, 1, 83-92.

8. Lin, Y., Long, K., “Studies of the chemical constituents of the Chinese gorgonian (IV)-junceellin, a new chlorine-containing diterpenoid from Junceella squamata”, Zhongshan Daxue Xuebao, Ziran Kexueban, 1983, 2, 46-51.

9. Burks, J. E., Helm, D. van der, Chang, C. Y., Ciereszko, L. S., “The crystal and molecular structure of briarein A, a diterpenoid from the gorgonian Briareum asbestinum”, Acta Cryst., 1977, B33, 704-709.

10. Long, K., Lin, Y., Huang, W., “Studies on the chemical constituents of the Chinese gorgonian (VI)— junceellin B, a new chlorinecontaining diterpenoid from Junceella squamata”, Zhongshan Daxue Xuebao, Ziran Kexueban, 1987, 2, 15-20.

11. Shin, J., Park, M., Fenical, W., “The junceellolides new anti-inflammatory diterpe
noids of the briarane class from the Chinese gorgonian Junceella fragilis”, Tetrahedron, 1989, 45, 1633-1638.

12. Bowden, B. F., Coll, J. C., Ko‥nig, G. M., “Studies of Australian soft corals XLVIII. New briaran diterpenoids from the gorgonian coral Junceella gemmacea”, Aust. J. Chem., 1990, 43, 151-159.

13. Isaacs, S., Carmely, S., Kashman, Y., “Juncins A-F, six new briarane diterpenoids from the gorgonian Junceella juncea”, J. Nat. Prod., 1990, 53, 596-602.

14. He, H. Y., Faulkner, D. J., “New chlorinated diterpenes from the 160 gorgonian Junceella gemmacea”, Tetrahedron, 1991, 47, 3271-3280.

15. Lin, Y., “Six kinds of N-acylsphingosines from the Chinese gorgonian Junceella squamata”, Zhongguo Haiyang Yaowu (Chin. J. Mar. Drugs), 1995, 14(2), 1-4.

16. Anjaneyulu, A. S. R., Rao, N. S. K., “Juncins G and H: new briarane diterpenoids of the Indian Ocean gorgonian Junceella juncea Pallas”, J. Chem. Soc., Perkin Trans 1, 1997, 959-962.

17. Garcı′a, M., Rodrı′guez, J., Jime′nez, C., “Absolute structures of new briarane diterpenoids from Junceella fragilis”, J. Nat. Prod., 1999, 62, 257-260.

18. Sung, P. J., Wu, S. L., Fang, H. J., Chiang, M. Y., Wu, J. Y., Fang, L. S., Sheu, J. H., “Junceellolides E-G, new briarane diterpenes from the west Pacific Ocean gorgonian Junceella fragilis”, J. Nat. Prod., 2000, 63, 1483-1487.

19. Shen, Y. C., Lin, Y. C., Chiang, M. Y., “Juncenolide A, a new briarane from the Taiwanese gorgonian Junceella juncea”, J. Nat. Prod., 2002, 65, 54-56.

20. Shen, Y. C., Lin, Y. C., Ko, C. L., Wang, L. T., “New briaranes from the Taiwanese gorgonian Junceella juncea”, J. Nat. Prod., 2003, 66, 302-305.

21. Shen, Y. C., Lin, Y. C., Huang, Y. L., “Juncenolide E, a new briarane from Taiwanese Gorgonian Junceella juncea”, J. Chin. Chem. Soc., 2003, 50, 1267-1270.

22. Anjaneyulu, A. S. R., Rao, V. L., Sastry, V. G., Venugopal, M. J. R. V., Schmitz, F. J., “Juncins I-M, five new briarane diterpenoids from the Indian Ocean gorgonian Junceella juncea Pallas”, J. Nat. Prod., 2003, 66, 507-510.

23. Sung, P. J., Fan, T. Y., Fang, L. S., Wu, S. L., Li, J. J., Chen, M. C., Cheng, Y. M., Wang, G. H., “Briarane derivatives from the gorgonian coral Junceella fragilis”, Chem. Pharm. Bull., 2003, 51, 1429-1431.

24. Sung, P. J., Fan, T. Y., Fang, L. S., Sheu, J. H., Wu, S. W., Wang, G. H., Lin, M. R., “Juncin N, a new briarane-type diterpenoid from the gorgonian coral Junceella juncea” Heterocycles, 2003, 61, 587-592.

25. Krishna, N., Muralidhar, P., Murali krishna Kumar, M., Venkata Rao, D., and Bheemasankara Rao, C.H., ”A new sphingolipid from the gorgonian Junceella juncea of the Indian Ocean” Nat. Prod. Res., 2004, 18, 551-555.

26. Sung, P. J., Lin, M. R., Chen, W. C, Fang, L. S., Lu, C. K., and Sheu, J. H., “Fragilide A, a novel diterpenoid from Junceella fragilis”, Bull. Chem. Soc. Jpn., 2004, 77, 1229-1230.

27. Sung, P. J., Lin M. R., and Fang, L. S., “Briarane diterpenoids from the Formosan gorgonian coral Junceella fragilis”, Chem. Pharm. Bull., 2004, 52, 1504-1506.

28. Qi, S. H., Zhang, S., Huang, H., Xiao, Z. H., Huang, J. S., Li, Q. X., “New briaranes from the south China Sea gorgonian Junceella juncea”, J. Nat. Prod., 2004, 67, 1907-1910.

29. Zhang, W., Guo, Y. W., Mollo, E., Cimino, G., “Junceellonoids A and B, two new briarane diterpenoids from the Chinese gorgonian Junceella fragilis RIDLEY”, Helv. Chim. Acta, 2004, 87, 2341-2345.

30. Qi, S. H., Zhang, S., Wen, Y. M., Xiao, Z. H., Li, Q. X., “New briaranes from the South China Sea gorgonian Junceella fragilis”, Helv. Chim. Acta, 2005, 88, 2349-2354.

31. Lin, Y. C., Huang, Y. L., Khalil, A. T., Chen, M. H., Shen, Y. C., “Juncenolides F and G, two new Briarane diterpenoids from Taiwanese gorgonian Junceella juncea”, Chem. Pharm. Bull., 2005, 53, 128-130.

32. Qi, S. H., Zhang, S., Qian, P. Y., Xiao, Z. H., and Li, M. Y., “Ten new antifouling briarane diterpenoids from the South China Sea gorgonian Junceella juncea”, Tetrahedron, 2006, 62, 9123-9130.

33. Kubota, N. K. Kobayashi, Y., Iwamoto, H., Fukazawa, Y., and Uchio, Y., “Two new halogenated briarane diterpenes from the Papuan gorgonian coral Junceella fragilis”, Bull. Chem. Soc. Jpn., 2006, 79, 634-636.

34. Sheu, J. H., Chen, Y. P., Hwang, T. L., Chiang, Michael Y., Fang, L. S., and Sung, P. J., “Junceellolides J-L, 11,20-epoxybriaranes from the gorgonian coral Junceella fragilis”, J. Nat. Prod., 2006, 69, 269-273.

35. Sung, P. J., Pai, C. H., Hwang, T. L., Fang, T. Y., Su, J. H., Chen, J. J., Sheu, J. H., “Junceols D-H, new polyoxygenated briaranes from sea whip gorgonian coral Junceella juncea”, Chem. Pharm. Bull., 2008, 56, 1276-1281.

36. Liaw, C. C., Shen, Y. C., Lin, Y. S., Hwang, T. L., Kuo, Y. H., Khalil, A. T., “Frajunolides E-K, briarane diterpenes from Junceella fragilis”, J. Nat. Prod., 2008, 71, 1551-1556.

37. Cheer J.; D. H. Smith; C. Djerassi; B. Tursch; J. C. Braekman, “Applications of Artificial Intelligence for ChemicalInference-XXI: Chemical Studies of Marine Invertebrates-XVII. The Computer-Assisted Identification of [+]-Palustrol in the Marine Organism Cespitularia sp., aff. Subviridis” , Tetrahedron 1976, 32, 1807-1810.
38. Braekman J. C.; D. Daloze; R. Ottinger; B. Tursch, “Chemical Studies of Marine Intertebrates. XXVII. on the Absolute Configuration of Aromadendrane Sesquiterpenes from the Soft Coral Cespitularia aff. Subviridis” , Experientia 1977, 33, 993.

39. Bowden B. F.; J. C. Coll; S. J. Mitchell; G. J. Stokie; J. F. Blount, “Studies of Australian soft coral. VIII A Chemical and Crystallographic Study of a Novel Bicyclic Diterpene Alcohol with a Rearranged Skeleton from an Unknown Species of Soft Coral” , Aust. J. Chem. 1978, 31, 2039-2046.

40. Bowden B. F.; J. C. Braekman; J. C. Coll; S. J. Mitchell, “Studies of Australian Soft Corals. A New Sesquiterpene Furan from Soft Corals of the Family Xeniidae and an Examination of Clavularia inflate from North Queensland Waters” , Aust J. Chem., 1980, 33, 927-932.

41. Burns K. P.; R. Kazlauskas; P. T. Murphy; R. J. Well; P. schonholzer, “Two Cembrances from Cespitularia Species (Soft Coral)”, Aust.J.chem. 1982, 35, 85-94.

42. Bowden B. F.; J. C. Coll; D. M. Tapiolas, “Studies of Australian Soft Coral. A Novel Trisnorsesquiterpene form a Cespitularia Species and the Isolation of Guaiazulene from a Small Blue Alcyonium Species” , Aust. J. Chem. 1983, 36, 211-214.

43. Bowden B. F.; J. C. Coll; J. M. Gulbis; M. F. Mackay; R. H. Willis, “Studies of Australian Soft Corals. XXXVIII Structure Determination of Several Diterpenes Derived from a Cespitularia Species (Coelenterata, Octocorallia, Xeniidae)” , Aust. J. Chem. 1986, 39, 803-812.

44. König G. M.; A. D. Wright, “A New Caryophyllene-Based Diterpene from the Soft Coral, Cespitularia sp. ”, J. Nat. Prod., 1993, 56, 2198-2200.

45. Coll J. C.; P. S. Kearns; J. A. Rideout, “Isolation of Novel Diterpene Triacetate from Two Soft Corals of the Order Alcyonacea” , J. Nat. Prod., 1998, 61, 835-837.

46. Duh C. Y.; A. A. H. El-Gamal; S. K. Wang; C. F. Dai, “Novel Terpenoids from Formosan Soft Carol Cespitularia Hypotentaculata” , J. Nat. Prod. 2002, 64, 1028-1031.


47. Shen Y. C.; Y. S. Lin ; Y. H. Kuo ; Y. B. Cheng, “ Cespitulactams A, B, and C, three new nitrogen-containing diterpenes from Cespitularia taeniata May” , Tetrahedron Letters 2005 , 46 , 7893–7897.

48. Shen Y. C.; C. J. Ho; Y. H. Kuo; Y. S. Lin, “Cespitulactones A and B, New Diterpenoids from Cespitularia taeniata” , Bioorg. Med. Chem. Lett. 2006, 16, 2369-2372.

49. Duh C. Y.; C. H. Li; S. K. Wang; C. F. Dai, “Diterpenoids, Norditerpenoids, and Secosteroids from the Formosan Soft Coral Cespitularia hypotentaculata” , J. Nat. Prod. 2006, 69, 1188-1192.

50. Shen Y. C.; J. J. Lin; Y. R. Wu; J. Y. Chang; C. Y. Duh; K. L. Lo, “New Norditerpenoids from Cespitularia hypotentaculata” , Tetrahedron Letters, 2006, 47, 6651-6655.

51. Shen Y. C.; Y. B. Cheng; J. Kobayashi; T. Kubota; Y. Takahashi; Y. Mikami; J. Ito; Y. S. Lin, “Nitrogen-Containing Verticillene Diterpenoids from the Taiwanese Soft Coral Cespitularia taeniata” , J. Nat. Prod. 2007, 70, 1961-1965

52. Shen Y. C.; Y. R. Wu; J. J. Lin; K. L. Lo.; Y. C. Kuo; A. T. Khalil, “ Eight New Diterpenoids from Soft Coral Cespitularia hypotentaculata” , Tetrahedron, 2007, 63, 10914-10920.

53. Janairo J. R. O.; G. C. Janairo; C. Y. Ragasa; B. F. Bowden, “A marine verticillane diterpenoid from Cespitularia erecta” , Nat. Prod. Res., 2008, 22, 48-52.

54. Shen Y. C.; K. L. Lo; Y. H. Kuo; Y. C. Kuo; C. H. Chen, and A. T. Khalil, “Cespihypotins Q-V, Verticillene Diterpenoids from Cespitularia hypotentaculata” , J. Nat. Prod. 2008, 71, 1993–1997.

55. Cheng Y. B.; C. Y. Chen; Y. H. Kuo; and Y. C. Shen, “New Nitrogen-Containing Sesquiterpenoids from the Taiwanese Soft Coral Cespitularia taeniata May” , CHEMISTRY & BIODIVERSITY 2009, 6, 1266-1272.

56. 方力行, 珊瑚學, 教育部大學聯合出版委員會, 1989, pp. 22-37.

57. 臺灣的珊瑚, 臺灣省政府教育廳, 1989, pp. 173.

58. AIMS 網頁：http：//www. aims. gov. au/

59. 宋秉鈞, 兩種柳珊瑚 Briareum excavatum 及 Junceella fragilis 所含具細胞毒性之 Briarane 類化合物的研究, 中山大學海洋資源研究所博士論文, 2000.

60. Lelong, H.; Ahond, A.; Chiaroni, A.; Poupat, C.; Riche, C.; Potier, P.; Pusset, J.; Pusset, M.; Laboute, P.; Menou, J. L. “Invertébrés Marins du Lagon Néo-Calédonien, VIII. Métabolites Terpéniques de Xenia membranacea” J. Nat. Prod. 1987, 50, 203-210.

61. Fabricius, K.; Alderslade, P., Soft Corals and Sea Fans, Australian Institute of Marine Science 2001, pp. 106-107.

62. Shen, Y. C.; Lin, Y. S.; Cheng, Y. B.; Cheng, K. C.; Khalil, A. T.; Kuo, Y. H.; Chien, C. T.; Lin Y. C. Novel taxane diterpenes from Taxus sumatrana with the first C-21
taxane ester. Tetrahedron, 2005, 61, 1345-1352.

63. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J. Am. Chem. Soc., 1971, 93, 2325-2327.

64. Schiff, P. B.; Fant, J.; Horwitz, S. B. Promotion of microtubule assembly in Vitro by Taxol. Nature, 1979, 277, 665-667.

65. Shannon, K. B.; Julie, C. C.; Moree, C. B.; Tirnauer, J. S.; Salmon, E. D. Taxol -stabilized microtubules can position the cytokinetic furrow in mammalian cells. Mol. Biol. Cell, 2005, 16, 4423-4436.

66. Simpkins, H.; Parekh, H. The transport and binding of Taxol. Gen Pharmac, 1997, 29, 167-172.

67. Shi, Q. W.; Kiyota, H. New natural taxane diterpenoids from taxus species since 1999. Chemistry and Biodiversity, 2005, 2, 1597-1623.

68. Parmar, V. S.; Amitabh, J.; Bisht, K.S.; Poonam, T.; Singh, S.K.; Ajay K.; Poonam; Rajni J.; Olsen, C.E. Constituents of the yew trees. Phytochemistry, 1999, 50, 1267-1304.

69. Baloglu, E.; Kingston, D.G.I. The taxane diterpenoids. J. Nat. Prod., 1999, 62, 1448-1472.

70. Shi, Q. W.; Lederman, Z.; Sauriol, F.; McCollum, R. S.; Zamir, L. O. A Yew in Israel, New Taxane Derivatives. J. Nat. Prod., 2004, 67, 168-173.

71. Shi, Q. W.; Sauriol, F.; Lesimple, A.; Zamir, L. O. First three examples of taxane-derived di-propellanes in Taxus canadensis needles. Chem. Commun., 2004, 544-545.

72. Shi, Q. W.; Ji, X.; Lesimple, A.; Sauriol, F.; Zamir, L. O. Reports on structure elucidation. Phytochemistry, 2004, 65, 3097-3106.

73. Shi, Q. W.; Sauriol, F.; Park, Y.; Smith Jr, V. H.; Lord, G.; Zamir, L. O. First example of conformational exchange in a natural taxane enolate. Magn. Reson. Chem., 2005; 43, 798-804.

74. Shi, Q. W.; Si, X. T.; Zhao, Y. M.; Su, X. H.; Li, X.; Zamir, L. O.; Yamada, T.; Kiyota, H.; Two new alkaloidal taxoids from the needles of Taxus cuspidata. Biosci. Biotechnol. Biochem., 2006, 70, 732-736.

75. Shi, Q. W.; Dong, M.; Huo, C. H.; Su, X. H.; Li, C. F.; Zhang, X. P.; Wang, Y. F.; Kiyota, H. New 14-hydroxy-taxane and 2α,20-epoxy-11(15→1)abeotaxane from the needles of Taxus canadensis. Biosci. Biotechnol. Biochem., 2007, 71, 1777-1780.

76. Petzke, T. L.; Shi, Q. W.; Sauriol, F.; Mamer, O.; Zamir, L. O. Taxanes from rooted cuttings of Taxus canadensis. J. Nat. Prod. 2004, 67, 1864-1869.

77. Wang, F. S.; Peng, L. Y.; Zhao, Y.; Xu, G.; Zhao, G. S.; Sun, H. D. Three new oxetane-ring-containing taxoids from Taxus chinensis. J. Nat. Prod. 2004, 67, 905-907.

78. Zhao, Y.; Wang, F. S.; Peng L. Y.; Li, X. L.; Xu, G.; Luo, X. X.; Lu, Y.; Wu, L.; Zheng, Q. T.; Zhao, Q. S. Taxoids from Taxus chinensis. J. Nat. Prod. 2006, 69, 1813-1815.

79. Xia, Z. H.; Peng, L. Y.; Xu, G.; Zhao, Q. S.; Sun, H. D. Two new taxoids from Taxus chinensis. Chemistry and Biodiversity, 2005, 2, 1316-1319.

80. Dong, M.; Zhang, M. L.; Wang, Y. F.; Zhang, X. P.; Li, C. F.; Shi, Q. W.; Cong, B.; Kiyota H. Prolidase from Xanthomonas maltophilia: purification and characterization of the enzyme. Biosci. Biotechnol. Biochem., 2007, 71, 2087-2090.

81. Shi, Q. W.; Li, Z. P.; Zhao, D.; Gu, J. S.; Oritani, T.; Kiyota, H. New 2(3.RAR.20)abeotaxane and 3,11-cyclotaxane from needles of Taxus cuspidata. Biosci. Biotechnol. Biochem., 2004, 68, 1584-1587.

82. Li, L.; Cao, C. M.; Huo, C.; Zhang, M.; Shi, Q. W.; kiyota, H. Structure elucidation and complete NMR spectral assignments of a new taxane-glycoside from the needles of Taxus cuspidata. Magn. Reson. Chem., 2005, 43, 475-478.

83. Shi, Q. W.; Cao, C. M.; Gu, J. S.; Kiyota, H. Four new epoxy taxanes from the needles of Taxus cuspidata. Natural Product Research, 2006, 20, 173-179.

84. Cao, C. M.; Zhang, M. L.; Wang, Y. F.; Shi, Q. W.; Yamada, T.; Kiyota, H. Two new taxanes from the branches bark and needles of Taxus cuspidata. Chemistry and Biodiversity, 2006, 3, 1153-1161.

85. Huo, C. H.; Su, X. H.; Li, X.; Zhang, C. F.; Wang, Y. F.; Shi, Q. W.; Kiyota, H. Structural determination of a new 2(3→20)abeotaxane with an unusual 13β-substitution and a new 6/8/6-ring taxane from Taxus cuspidata. Magn. Reson. Chem., 2007, 45, 527-530.

86. Morita, H.; Machida, I.; Hirasawa, Y.; Kobayashi, J. Taxezopidines M and N, new taxoids from Japanese yew Taxus cuspidata. J. Nat. Prod., 2005, 68, 935-937.

87. Bai, J.; Kitabatake, M.; Toyoizumi, K.; Fu, L.; Zhang, S.; Dai, J.; Sakai, J.; Hirose, K.; Yamori, T.; Tomida, A.; Tsuruo, T.; Ando, M. Production of biologically active taxoids by a callus culture of Taxus cuspidata. J. Nat. Prod. 2004, 67, 58-63.

88. Dai, J.; Bai, J.; Hasegawa, T.; Nishizawa, S.; Sakai, J.; Oka, S.; Kiuchi, M.; Hirose, K.; Tomida, A.; Tsuruo, T.; Li, M.; Ando, M. A new taxid from a callus culture of Taxus cuspidate as an MDR reversal agent. Chem. Pharm. Bull. 2006, 45, 306-309.

89. Bai, J.; Ito, N.; Sakai, J.; Kitabatake, M.; Fujisawa, H.; Bai, L.; Dai, J.; Zhang, S.; Hirose, K.; Tomida, A.; Tsuruo, T.; Ando, M. Taxoids and abietanes from callus cultures of Taxus cuspidata. J. Nat. Prod. 2005, 68, 497-501.

90. Shi, Q. W.; Li, Z. P.; Wang, C. L.; Zhang, M. L.; Choony, N.; Kiyota, H. New taxanes from the seeds of Taxus mairei. Journal of Asian Natural Products Research, 2006, 8, 431-437.

91. Shi, Q. W.; Zhao, Y. M.; Si, X. T.; Li, Z.P.; Yamada, T.; Kiyota, H. 1-deoxypaclitaxel and abeo-taxoids from the seeds of Taxus mairei. J. Nat. Prod. 2006, 69, 280-283.

92. Shi, Q. W.; Li, Z. P.; Zhao, D.; Gu, J. S.; Kiyota, H. Isolation and structure revision of 10-deacetyltaxinine from the seeds of the Chinese yew, Taxus mairei. Natural Product Research, 2006, 20, 47-51.


93. Shen, Y. C.; Ko, C. L.; Cheng, Y. B.; Chiang, M. Y.; Khalil, A. T. Newregio- and Stereoselective O-decacetylated and Epoxy Products of Taxanes Isolated from Taxus mairei. J. Nat. Prod. 2004, 67, 2136-2140.

94. Shen, Y. C.; Cheng, K. C.; Lin, C. H.; Cheng, Y. B.; Khalil, A. T.; Guh, J. H.; Chien, C. T.; Teng, C. M.; Chang, Y. T. Three new taxane diterpenoids from Taxus sumatrana. J. Nat. Prod. 2005, 68, 90-93.

95. Shen,Y. C.; Hsu, S. M.; Lin, Y. S.; Cheng, K. C.; Chien, C. T.; Chou, C. H.; Cheng, Y. B. New bicyclic taxane diterpenoids from Taxus sumatrana. Chem. Pharm. Bull. 2005, 53, 808-810.

96. Shen, Y. C.; Lin, Y. S.; Cheng, Y. B.; Cheng, K. C.; Khalil, A. T.; Kuo, Y. H.; Chien, C. T.; Lin Y. C. Novel taxane diterpenes from Taxus sumatrana with the first C-21 taxane ester. Tetrahedron, 2005, 61, 1345-1352.

97. Banskota, A. H.; Usia, T.; Tezuka, Y.; kouda, K.; Nguyen, N. T.; Kadota, S. Three new C-14 oxygenated taxanes from the wood of Taxus yunnanensis. J. Nat. Prod., 2002, 65, 1700-1702.

98. 劉葉經, “台灣木本植物誌”, 107-111, 國立中興大學農學院出版, 1972。

99. Shen, Y. C., Lin, Y. S., Hsu, S. M., Khalil, A. T., Wang, S. S., Chien, C. T., Kuo, Y. H., Chou, C. H. Tasumatrols P-T, five new taxoids from Taxus sumatrana. Helvetica Chimica Acta, 2007, 90, 1319-1329.

100. Yue, Q.; Fang, Q. C.; Liang, X. T.; He, C. H.; Jing, X. L. Rearranged taxoids from Taxus yunnanensis. Planta Med., 1995, 61, 375-377.

101. Wang X., H. Shigemori, J. Kobayashi, Tetrahedron 1996, 53, 2327.