Taxanes with C-5-amino-side chains from the needles of Taxus canadensis

Phytochemistry

Volumn 65, Issue 23, 2004, Pages 3097-3106

  Shi, Qing Wen ^a   Ji, Xiuhong ^a   Lesimple, Alain ^b   Sauriol, Françoise ^c   Zamir, Lolita O ^a,d  

^a INRS INSTITUT ARMAND FRAPPIER   (Canada)

^b MCGILL UNIVERSITY   (Canada)

^c QUEEN S UNIVERSITY   (Canada)

^d MCGILL UNIVERSITY   (Canada)

Author keywords

C 5 amino side chain; Metabolites; Taxacae; Taxanes; Taxus canadensis; Yew

Indexed keywords

2ALPHA HYDROXY 7BETA,9ALPHA,10BETA,13ALPHA TETRAACETOXY 5ALPHA (2' HYDROXY 3' N,N DIMETHYLAMINO 3' PHENYL)PROPIONYLOXYTAXA 4(20),11 DIENE; 2ALPHA,17 DIHYDROXY 9ALPHA,10BETA,13ALPHA TRIACETOXY 5ALPHA (3' N,N DIMETHYLAMINO 3' PHENYL)PROPIONYLOXYTAXA 4(20),11 DIENE; 2ALPHA,7BETA,9ALPHA,10BETA,13 PENTAACETOXY 11BETA HYDROXY 5ALPHA (3' N,N DIMETHYLAMINO 3' PHENYL)PROPIONYLOXYTAXA 4(20),12 DIENE; 2ALPHA,9ALPHA DIHYDROXY 10BETA,13ALPHA DIACETOXY 5ALPHA (3' METHYLAMINO 3' PHENYL)PROPIONYLOXYTAXA 4(20),11 DIENE; 9ALPHA HYDROXY 2ALPHA,10BETA,13ALPHA TRIACETOXY 5ALPHA (3' N,N DIMETHYLAMINO 3' PHENYL)PROPIONYLOXYTAXA 4(20),11 DIENE; PLANT EXTRACT; TAXANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; MEDICINAL PLANT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUBSTITUTION REACTION; TAXUS CANADENSIS;

MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; TAXOIDS; TAXUS;

TAXUS; TAXUS CANADENSIS; TAXUS CUSPIDATA;

EID: 8444226000     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2004.08.042     Document Type: Article

References (28)

1. Appendino, G., 1995. Naturally occurring taxoids, vol. 22, pp. 1-53 and The structural elucidation of taxoids, vol. 22, pp. 55-101. In: Farina, V. (Ed.), Timmerman, H., The Chemistry and Pharmacology of Taxol (R) and its Derivatives
2. Appendino, G., 1995. Naturally occurring taxoids, vol. 22, pp. 1-53 and The structural elucidation of taxoids, vol. 22, pp. 55-101. In: Farina, V. (Ed.), Timmerman, H., The Chemistry and Pharmacology of Taxol (R) and its Derivatives
3. G. Appendino, H.C. Ozen, I. Fenoglio, P. Gariboldi, B. Gabetta, and E. Bombardelli Pseudoalkaloid taxanes from Taxus baccata Phytochemistry 33 1993 1521 1523
4. E. Baloglu, and D.G.I. Kingston The taxane diterpenoids J. Nat. Prod. 62 1999 1448 1472
5. A.H. Banskota, T. Usia, Y. Tezuka, K. Kouda, N. Nguyen, and S. Kadota Three new C-14 oxygenated taxanes from wood of Taxus yunnanensis J. Nat. Prod. 65 2002 1700 1702
6. M.I. Choudhary, A.M. Khan, H. Rehman, A. Rahman, and M. Ashraf Two new rearranged taxoids from Taxus wallichiana Zucc Chem. Pharm. Bull. 50 2002 1488 1490
7. G.M. Cragg, D.J. Newman, and K.M. Snader Natural products in drug discovery and development J. Nat. Prod. 60 1997 52 60
8. F. Gueritte General and recent aspects of the chemistry and structure activity relationships of taxol Curr. Pharmaceut. Des. 7 2001 1229 1249
9. D.G.I. Kingston Taxol, a molecule for all seasons J. Chem. Soc., Chem. Commun. 2001 867 880
10. D.G.I. Kingston, A.A. Molinero, and G.M. Rimoldi W. Herz R.E. Moore G.W. Kirby W. Steglich C. Tamm Progress in the Chemistry of Organic Natural Products 61 1993 Springer Wien 1 206
11. D.G.I. Kingston, P.G. Jagtap, H. Yuan, and L. Samala W. Herz H. Falk G.W. Kirby Progress in the Chemistry of Organic Natural Products vol. 84 2002 Springer Wien 53 225
12. J. Kobayashi, H. Hosoyama, T. Katsui, N. Yoshida, and H. Shigemori Taxuspines N, O, and P, new taxoids from Japanese yew Taxus cuspidata Tetrahedron 52 1996 5391 5396
13. S.H. Li, H.J. Zhang, P. Yao, H.D. Sun, and H.H.S. Fong Taxane diterpenoids from the bark of Taxus yunnanensis Phytochemistry 38 2001 369 374
14. S.H. Li, H.J. Zhang, X.M. Niu, P. Yao, H.D. Sun, and H.H.S. Fong Taxuyunnanines S-V, new taxoids from Taxus yunnanensis Planta Med. 68 2002 253 257
15. S.H. Li, H.J. Zhang, X.M. Niu, P. Yao, H.D. Sun, and H.H.S. Fong Novel taxoids from the Chinese yew Taxus yunnanensis Tetrahedron 59 2003 37 45
16. D.J. Newman, G.M. Cragg, and K.M. Snader Natural products as sources of new drugs over the periods 1981-2002 J. Nat. Prod. 66 2003 1022 1037
17. N.T. Nguyen, A.H. Banskota, Y. Tezuka, T. Nobukawa, and S. Kadota Diterpenes and sesquiterpenes from the bark of Taxus yunnanensis Phytochemistry 64 2001 1141 1147
18. Y.C. Shen, S.S. Wang, Y.L. Pan, K.L. Lo, L. Chakraborty, C.T. Chien, Y.H. Kuo, and Y.C. Lin New taxane diterpenoids from the leaves and twigs of Taxus sumatrana J. Nat. Prod. 65 2002 1848 1852
19. Y.C. Shen, Y.T. Chang, Y.C. Lin, C.L. Lin, Y.H. Kuo, and C.Y. Chen New taxane diterpenoids from the roots of Taiwanese Taxus mairei Chem. Pharm. Bull. 50 2002 781 787
20. H. Shigemori, W.W. Wang, N. Yoshida, and J. Kobayashi Taxuspines X-Z, new taxoids from Japanese yew Taxus cuspidata Chem. Pharm. Bull. 45 1997 1205 1208
21. Y. Shinozaki, N. Fukamiya, M. Fukushima, M. Okano, T. Nehira, L. Tagahara, S.X. Zhang, D.C. Zhang, and K.H. Lee Dataxusins C and D, two novel taxoids from Taxus yunnnensis J. Nat. Prod. 65 2002 371 374
22. Q.W. Shi, T. Oritani, D. Zhao, R. Murakami, and T. Oritani Three new taxoids from the seeds of Japanese yew, Taxus cuspidata Planta Med. 66 2000 294 299
23. Q.W. Shi, F. Sauriol, O. Mamer, and O.L. Zamir A novel minor metabolite (taxane?) from Taxus candensis needles Tetrahedron Lett. 43 2002 6869 6873
24. Q.W. Shi, F. Sauriol, O. Mamer, and O.L. Zamir New minor taxane analogues from the needles of Taxus canadensis Bioorg. Med. Chem. 11 2003 293 303
25. Q.W. Shi, F. Sauriol, O. Mamer, and O.L. Zamir New minor taxane derivatives from the needles of Taxus canadensis J. Nat. Prod. 66 2003 1480 1485
26. Q.W. Shi, F. Sauriol, A. Lesimple, and O.L. Zamir First three examples of a taxane- derived di-propellane in Taxus canadensis needles J. Chem. Soc., Chem. Commun. 544 2004 545
27. M.C. Wani, H.L. Taylor, M.E. Wall, P. Coggon, and A.T. McPhail Plant antitumor agents. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia J. Am. Chem. Soc. 93 1971 2325 2327
28. J.Z. Zhang, F. Sauriol, O. Mamer, X.L. You, M. Alaoui-Jamali, G. Batist, and L.O. Zamir New taxane analogues from the needles of Taxus canadensis J. Nat. Prod. 64 2001 450 455 and references therein