Revisão Revisado por pares

Chemical Studies on Taxus cuspidata

2010; Wiley; Volume: 7; Issue: 7 Linguagem: Catalão

10.1002/cbdv.200800295

ISSN

1612-1880

Autores

Yu‐Fang Wang, Shu‐Hong Yu, Mei Dong, Manli Zhang, Chang‐Hong Huo, Qing‐Wen Shi,

Tópico(s)

Synthetic Organic Chemistry Methods

Resumo

Chemistry & BiodiversityVolume 7, Issue 7 p. 1698-1716 Review Chemical Studies on Taxus cuspidata Yu-Fang Wang, Yu-Fang Wang Laboratory of Natural Product Chemistry, School of Pharmaceutical Sciences, Hebei Medical University, 050017, Shijiazhuang, P. R. ChinaSearch for more papers by this authorShu-Hong Yu, Shu-Hong Yu Laboratory of Natural Product Chemistry, School of Pharmaceutical Sciences, Hebei Medical University, 050017, Shijiazhuang, P. R. ChinaSearch for more papers by this authorMei Dong, Mei Dong Department of Forensic Medicine, Hebei Medical University, 050017, Shijiazhuang, P. R. ChinaSearch for more papers by this authorMan-Li Zhang, Man-Li Zhang Laboratory of Natural Product Chemistry, School of Pharmaceutical Sciences, Hebei Medical University, 050017, Shijiazhuang, P. R. ChinaSearch for more papers by this authorChang-Hong Huo, Chang-Hong Huo Laboratory of Natural Product Chemistry, School of Pharmaceutical Sciences, Hebei Medical University, 050017, Shijiazhuang, P. R. ChinaSearch for more papers by this authorQing-Wen Shi, Qing-Wen Shi Laboratory of Natural Product Chemistry, School of Pharmaceutical Sciences, Hebei Medical University, 050017, Shijiazhuang, P. R. ChinaSearch for more papers by this author Yu-Fang Wang, Yu-Fang Wang Laboratory of Natural Product Chemistry, School of Pharmaceutical Sciences, Hebei Medical University, 050017, Shijiazhuang, P. R. ChinaSearch for more papers by this authorShu-Hong Yu, Shu-Hong Yu Laboratory of Natural Product Chemistry, School of Pharmaceutical Sciences, Hebei Medical University, 050017, Shijiazhuang, P. R. ChinaSearch for more papers by this authorMei Dong, Mei Dong Department of Forensic Medicine, Hebei Medical University, 050017, Shijiazhuang, P. R. ChinaSearch for more papers by this authorMan-Li Zhang, Man-Li Zhang Laboratory of Natural Product Chemistry, School of Pharmaceutical Sciences, Hebei Medical University, 050017, Shijiazhuang, P. R. ChinaSearch for more papers by this authorChang-Hong Huo, Chang-Hong Huo Laboratory of Natural Product Chemistry, School of Pharmaceutical Sciences, Hebei Medical University, 050017, Shijiazhuang, P. R. ChinaSearch for more papers by this authorQing-Wen Shi, Qing-Wen Shi Laboratory of Natural Product Chemistry, School of Pharmaceutical Sciences, Hebei Medical University, 050017, Shijiazhuang, P. R. ChinaSearch for more papers by this author First published: 15 July 2010 https://doi.org/10.1002/cbdv.200800295Citations: 10AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat References 1 E. Baloğlu, D. G. I. Kingston, J. Nat. Prod. 1999, 62, 1448. 2 V. S. Parmar, A. Jha, K. S. Bisht, P. Taneja, S. K. Singh, A. Kumar, Poonam, R. Jain, C. E. Olsen, Phytochemistry 1999, 50, 1267. 3 D. G. I. Kingston, A. A. Molinero, J. M. Rimoldi, in 'Progress in the Chemistry of Organic Natural Products', Springer, New York, 1993, Vol. 61, p. 1. 4 'The Chemistry and Pharmacology of Taxol and Its Derivatives', Eds. G. Appendino, V. Farina, Elsevier, Amsterdam, 1995, Vol. 22, p. 1. 5 Q.-W. Shi, H. Kiyota, Chem. Biodiversity 2005, 2, 1597. 6 H. Kondo, T. Takahashi, Yakugaku Zasshi 1925, 45, 861. 7 M. Kurono, Y. Nakadaira, S. Onuma, K. Sasaki, K. Nakanishi, Tetrahedron Lett. 1963, 4, 2153. 8 M. Kurono, Y. Maki, K. Nakanishi, M. Ohashi, K. Ueda, S. Uyeo, M. C. Woods, Y. Yamamoto, Tetrahedron Lett. 1965, 24, 1917. 9 J. Kobayashi, H. Shigemori, Heterocycles 1999, 52, 1111. 10 J. Kobayashi, H. Shigemori, Med. Res. Rev. 2002, 22, 305. 11 H. Shigemori, J. Kobayashi, J. Nat. Prod. 2004, 67, 245. 12 T. Sugiyama, T. Oritani, T. Oritani, Biosci., Biotechnol., Biochem. 1994, 58, 1923. 13 J. Kobayashi, A. Ogiwara, H. Hosoyama, H. Shigemori, N. Yoshida, T. Sasaki, Y. Li, S. Iwasaki, M. Naito, T. Tsuruo, Tetrahedron 1994, 50, 7401. 14 X.-X. Wang, H. Shigemori, J. Kobayashi, Tetrahedron 1996, 52, 2337. 15 J. Kobayashi, H. Hosoyama, T. Katsui, N. Yoshida, H. Shigemori, Tetrahedron 1996, 52, 5391. 16 H. Shigemori, X. X. Wang, J. Kobayashi, Chem. Pharm. Bull. 1997, 45, 1205. 17 F. Balza, S. Tachibana, H. Barrios, G. H. N. Towers, Phytochemistry 1991, 30, 1613. 18 L. Barboni, P. Gariboldi, E. Torregiani, G. Appendino, B. Gabetta, G. Zini, E. Bombardelli, Phytochemistry 1993, 33, 145. 19 R. Murakami, Q.-W. Shi, T. Horiguchi, T. Oritani, Biosci., Biotechnol., Biochem. 1999, 63, 1660. 20 H. Morita, A. Gonda, L. Wei, Y. Yamamura, K. Takeya, H. Itokawa, J. Nat. Prod. 1997, 60, 390. 21 X.-J. Tong, W.-S. Fang, J.-Y. Zhou, C.-H. He, W.-M. Chen, Q.-C. Fang, J. Nat. Prod. 1995, 58, 233. 22 X.-X. Wang, H. Shigemori, J. Kobayashi, Tetrahedron 1996, 52, 12159. 23 K. Fuji, K. Tanaka, B. Li, T. Shingu, H. Sun, T. Taga, J. Nat. Prod. 1993, 56, 1520. 24 X. J. Tong, W. S. Fang, J. Y. Zhou, W. M. Chen, Q. C. Fang, Yaoxue Xuebao 1994, 29, 55. 25 K. V. Rao, J. H. Johnson, Phytochemistry 1998, 49, 1361. 26 H. Morita, A. Gonda, L. Wei, Y. Yamamura, H. Wakabayashi, K. Takeya, H. Itokawa, Planta Med. 1998, 64, 183. 27 Q.-W. Shi, T. L. Petake, F. Sauriol, O. Mamer, L. O. Zamir, Can. J. Chem. 2003, 90, 64. 28 H. Hosoyama, A. Inubushi, T. Katsui, H. Shigemori, J. Kobayashi, Tetrahedron 1996, 52, 13145. 29 L. Barboni, P. Gariboldi, G. Appendino, R. Enriù, B. Gabetta, E. Bombardelli, Liebigs Ann. Chem. 1995, 345. 30 Q.-W. Shi, T. Oritani, T. Sugiyama, T. Horiguchi, R. Murakami, D. Zhao, T. Oritani, Tetrahedron 1999, 55, 8365. 31 Q.-W. Shi, T. Oritani, D. Zhao, R. Murakami, T. Oritani, Planta Med. 2000, 66, 294. 32 Q. W. Shi, T. Oritani, K. Hiromasa, Nat. Prod. Lett. 2001, 15, 55. 33 H. Morita, A. Gonda, L. Wei, Y. Yamamura, H. Wakbayashi, K. Takeya, Phytochemistry 1998, 48, 857. 34 Q.-W. Shi, Z.-P. Li, D. Zhao, J.-S. Gu, T. Oritani, H. Kiyota, Biosci., Biotechnol., Biochem. 2004, 68, 1584. 35 C. Huo, X. Su, X. Li, X. Zhang, C. Li, Y. Wang, Q. Shi, H. Kiyota, Magn. Reson. Chem. 2007, 45, 527. 36 J. Kobayashi, A. Inubushi, H. Hosoyama, N. Yoshida, T. Sasaki, H. Shigemori, Tetrahedron 1995, 51, 5971. 37 K. Kosugi, J. Sakai, S. Zhang, Y. Watanabe, H. Sasaki, T. Suzuki, H. Hagiwara, N. Hirata, K. Hirose, M. Ando, A. Tomida, T. Tsuruo, Phytochemistry 2000, 54, 839. 38 C.-M. Cao, M.-L. Zhang, Y.-F. Wang, Q.-W. Shi, T. Yamada, H. Kiyota, Chem. Biodiversity 2006, 3, 1153. 39 J. Y. Liang, Z. D. Min, M. Niwa, J. Acta Chim. Sin. 1988, 46, 1053. 40 H. C. Chiang, M. C. Woods, Y. Nakadaira, K. Nakanishi, J. Chem. Soc., Chem. Commun. 1967, 1201. 41 T. Takahashi, J. Pharm. Soc. Jpn. 1931, 51, 401. 42 M. Miyazaki, K. Shimizu, H. Mishima, M. Kurabayashi, Chem. Pharm. Bull. 1968, 16, 546. 43 X.-X. Wang, H. Shigemori, J. Kobayashi, J. Nat. Prod. 1998, 61, 474. 44 L. Ettouati, A. Ahond, O. Convert, C. Poupat, P. Potier, Bull. Soc. Chim. Fr. 1988, 8, 749. 45 M.-K. Yeh, J.-S. Wang, L.-P. Liu, F.-C. Chen, Phytochemistry 1988, 27, 1534. 46 D. P. Della Casa de Marcano, T. G. Halsall, J. Chem. Soc., Chem. Commun. 1969, 1282. 47 J. Sakai, H. Sasaki, K. Kosugi, S. Zhang, N. Hirata, K. Hirose, A. Tomida, T. Tsuruo, M. Ando, Heterocycles 2001, 54, 999. 48 Q.-W. Shi, T. Oritani, T. Horiguchi, T. Sugiyama, R. Murakami, T. Yamada, Biosci., Biotechnol., Biochem. 1999, 63, 924. 49 Q. Cheng, T. Oritani, T. Horiguchi, Biosci. Biotechnol., Biochem. 2000, 64, 894. 50 M. Ando, J. Sakai, S. Zhang, Y. Watanabe, K. Kosugi, T. Suzuki, H. Hagiwara, J. Nat. Prod. 1997, 60, 499. 51 Q.-W. Shi, T. Oritani, T. Sugiyama, T. Oritani, Nat. Prod. Lett. 2000, 14, 265. 52 V. S. Parmar, A. Jha, in 'Studies in Natural Product Chemistry', Ed. Atta-ur-Rahman, Elsevier Science B.V, 1998, Vol. 20, p. 79. 53 Q.-W. Shi, F. Sauriol, O. Mamer, L. O. Zamir, J. Nat. Prod. 2003, 66, 1480. 54 M. Dong, M.-L. Zhang, Y.-F. Wang, X.-P. Zhang, C.-F. Li, Q.-W. Shi, B. Cong, H. Kiyota, Biosci., Biotechnol., Biochem. 2007, 71, 2087. 55 J. Kobayashi, H. Hosoyama, H. Shigemori, Y. Koiso, S. Iwasaki, Experientia 1995, 51, 592. 56 Q. W. Shi, Doctoral thesis, Tohoku University, Sendai, Japan, 2000; Q.-W. Shi, T. Oritani, H. Kiyota, D. Zhao, Phytochemistry 2000, 54, 829. 57 B. Li, K. Tanaka, K. Fuji, H. Sun, T. Taga, Chem. Pharm. Bull. 1993, 41, 1672. 58 H. Shigemori, C. A. Sakurai, H. Hosoyama, A. Kobayashi, S. Kajiyama, J. Kobayashi, Tetrahedron 1999, 55, 2553. 59 F. Yoshizaki, M. Fukuda, S. Hisamichi, T. Ishida, Y. In, Chem. Pharm. Bull. 1988, 36, 2098. 60 U. K. Nizam, P. Nazneen, J. Sci. Ind. Res. 1987, 46, 512. 61 J. A. Beutler, G. M. Chmurny, S. A. Look, K. M. Witherup, J. Nat. Prod. 1991, 54, 893. 62 H. Morita, I. Machida, Y. Hirasawa, J. Kobayashi, J. Nat. Prod. 2005, 68, 935. 63 M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon, A. T. McPhail, J. Am. Chem. Soc. 1971, 93, 2325. 64 H. Morita, A. Gonda, L. Wei, K. Takeya, H. Itokawa, Bioorg. Med. Chem. Lett. 1997, 7, 2387. 65 R. G. Powell, R. W. Miller, C. R. Smith Jr., J. Chem. Soc., Chem. Commun. 1979, 102. 66 H. Morita, L. Wei, A. Gonda, K. Takeya, H. Itokawa, Phytochemistry 1997, 46, 583. 67 G. P. Gunawardana, U. Premachandran, N. S. Burres, D. N. Whittern, R. Henry, S. Spanton, J. B. McAlpine, J. Nat. Prod. 1992, 55, 1686. 68 L. O. Zamir, M. E. Nedea, Z.-H. Zhou, S. Bélair, G. Caron, F. Sauriol, E. Jacomain, F. I. Jean, F.-X. Garneau, O. Mamer, Can. J. Chem. 1995, 73, 655. 69 J. L. McLaughlin, R. W. Miller, R. G. Powell, C. R. Smith Jr., J. Nat. Prod. 1981, 44, 312. 70 L. Barboni, P. Gariboldi, E. Torregiani, G. Appendino, B. Gabetta, E. Bombardelli, Phytochemistry 1994, 36, 987. 71 H. Zhang, Y. Takeda, T. Matsumoto, Y. Minami, K. Yoshida, W. Xiang, Q. Mu, H. Sun, Heterocycles 1994, 38, 975. 72 W. Ma, G. L. Park, G. A. Gomez, M. H. Nieder, T. L. Adams, J. S. Aynsley, O. P. Sahai, R. J. Smith, R. W. Stahlhut, P. J. Hylands, F. Bitsch, C. Shackleton, J. Nat. Prod. 1994, 57, 116. 73 G. Appendino, G. Cravotto, R. Enriù, P. Gariboldi, L. Barboni, E. Torregiani, B. Gabetta, G. Zini, E. Bombardelli, J. Nat. Prod. 1994, 57, 607. 74 C. Huo, X. Zhang, C. Li, Y. Wang, Q. Shi, H. Kiyota, Biochem. Syst. Ecol. 2007, 35, 704. 75 X.-X. Wang, H. Shigemori, J. Kobayashi, Tetrahedron Lett. 1997, 38, 7587. 76 Q.-W. Shi, C.-M. Cao, J.-S. Gu, H. Kiyota, Nat. Prod. Res. 2006, 20, 173. 77 C.-L. Wang, M.-L. Zhang, C.-M. Cao, Q.-W. Shi, H. Kiyota, Heterocycl. Commun. 2005, 11, 211. 78 L. O. Zamir, J. Zhang, J. Wu, F. Sauriol, O. Mamer, Tetrahedron 1999, 55, 14323. 79 M.-L. Zhang, Q.-W. Shi, M. Dong, Y.-F. Wang, C.-H. Huo, Y.-C. Gu, B. Cong, H. Kiyota, Tetrahedron Lett. 2008, 49, 1180. 80 Q.-W. Shi, T. Oritani, T. Sugiyama, R. Murakami, T. Horiguchi, J. Asian Nat. Prod. Res. 1999, 2, 63. 81 R. Murakami, Q.-W. Shi, T. Oritani, Phytochemistry 1999, 52, 1577. 82 H. Kiyota, Q.-W. Shi, T. Oritani, L. G. Li, Biosci., Biotechnol., Biochem. 2001, 65, 35. 83 P. V. Ripa, E. A. Martin, S. M. Cocciolone, J. H. Adler, Phytochemistry 1990, 29, 425. 84 F. Yoshizaki, M. Fufuda, S. Hisamichi, Shoyakugaku Zashi 1986, 40, 429. 85 H. Erdtman, K. Tsuno, Phytochemistry 1969, 8, 931. 86 F. Kawamura, Y. Kikuchi, T. Ohira, M. Yastagai, J. Wood Sci. 2000, 46, 167. 87 K. Fumio, O. Tatsuro, K. Yoshinari, Jpn. Wood Res. Soc. 2004, 50, 548; Y.-C. Shen, C.-Y. Chen, Y.-J. Chen, Y.-H. Kuo, C.-T. Chien, Y.-M. Lin, Chin. Pharm. J. 1994, 49, 285. 88 K. Fuji, K. Tanaka, B. Li, T. Shingu, H. Sun, T. Taga, Tetrahedron Lett. 1992, 33, 7915. 89 A. Chu, M. Furlan, L. B. Davin, J. Zajicek, G. H. N. Towers, C. M. Soucy-Breau, S. J. Rettig, R. Croteau, N. G. Lewis, Phytochemistry 1994, 36, 975. 90 G. Appendino, L. Borboni, P. Gariboldi, E. Bombardielli, B. Gabetta, D. Viterbo, Chem. Commun. 1993, 1587. 91 J. Zhang, F. Sauriol, O. Mamer, L. O. Zamir, Phytochemistry 2000, 54, 221. 92 G. Appendino, P. Lusso, P. Gariboldi, E. Bombardelli, B. Gabetta, Phytochemistry 1992, 31, 4259. 93 H. Hosoyama, H. Shigemori, Y. In, T. Ishida, J. Kobayashi, Tetrahedron 1998, 54, 2521. 94 T. Horiguchi, Ph.D. thesis, Tohoku University, Sendai, Japan, 2001. 95 M. Sako, H. Suzuki, N. Yamamoto, K. Hirota, Y. Maki, J. Chem. Soc., Perkin Trans. 1 1998, 417. 96 T. Horiguchi, C. D. Rithner, R. Croteau, R. M. Williams, Tetrahedron 2003, 59, 267. 97 G. Samaranayake, K. A. Neidigh, D. G. I. Kingston, J. Nat. Prod. 1993, 56, 884. 98 W.-S. Fang, Q.-C. Fang, X.-T. Liang, Y. Lu, Q.-T. Zheng, Tetrahedron 1995, 51, 8483. 99 L. O. Zamir, Z. H. Zhou, G. Caron, M. E. Nedea, F. Sauriol, O. Mamer, Chem. Commun. 1995, 529. 100 Q.-W. Shi, T. Oritani, T. Sugiyama, K. Kiyota, J. Nat. Prod. 1998, 61, 1437. 101 P. B. Shiff, J. Fant, S. B. Horwitz, Nature 1979, 277, 665. 102 D. G. I. Kingston, Pharmacol. Ther. 1991, 52, 1. 103 E. L. M. van Rozendaal, S. J. L. Kurstjens, T. A. van Beek, R. G. van den Berg, Phytochemistry 1999, 52, 427. 104 Q. W. Shi, F. Sauriol, O. Mamer, L. O. Zamir, Tetrahedron Lett. 2002, 43, 6869. 105 Q. W. Shi, F. Sauriol, O. Mamer, L. O. Zamir, Chem. Commun. 2003, 68. 106 Q. W. Shi, F. Sauriol, A. Lesimple, L. O. Zamir, Chem. Commun. 2004, 544. 107 C.-H. Huo, X.-H. Su, Y.-F. Wang, X.-P. Zhang, Q.-W. Shi, H. Kiyota, Tetrahedron Lett. 2007, 48, 2721. 108 M.-L. Zhang, M. Dong, C.-H. Huo, L.-G. Li, F. Sauriol, Q.-W. Shi, Y.-C. Gu, H. Makabe, H. Kiyota, Eur. J. Org. Chem. 2008, 5414. Citing Literature Volume7, Issue7July 2010Pages 1698-1716 ReferencesRelatedInformation

Referência(s)