A Yew in Israel, New Taxane Derivatives

Journal of Natural Products

Volumn 67, Issue 2, 2004, Pages 168-173

  Shi, Qing Wen ^a   Lederman, Zel ^b   Sauriol, Francoise ^c   McCollum, Robert S ^a   Zamir, Lolita O ^a  

^a UNIVERSITÉ LAVAL   (Canada)

^b Jerusalem Botanical Gardens   (Israel)

^c QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1BETA,2ALPHA,9ALPHA,10BETA TETRAHYDROXY 5ALPHA CINNAMOYLOXYTAXA 4(20),11 DIEN 13 ONE; 2ALPHA,10BETA DIACETOXY 1BETA,9ALPHA DIHYDROXY 5ALPHA CINNAMOYLOXY 3,11 CYCLOTAXA 4(20) DIEN 13 ONE; 2ALPHA,9ALPHA,10BETA TRIHYDROXY 5ALPHA CINNAMOYLOXYTAXA 4(20),11 DIEN 13 ONE; 5ALPHA,9ALPHA,10BETA,13ALPHA TETRAACETOXY 14BETA O (BETA DEXTRO GLUCOPYRANOSYL)TAXA 4(20),11 DIENE; 9ALPHA ACETOXY 2ALPHA,10BETA DIHYDROXY 5ALPHA CINNAMOYLOXYTAXA 4(20,11 DIEN 13 ONE; TAXANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG IDENTIFICATION; DRUG STRUCTURE; ISRAEL; MASS SPECTROMETRY; NONHUMAN; PLANT GROWTH; PROTON NUCLEAR MAGNETIC RESONANCE; TAXUS BACCATA;

BRIDGED COMPOUNDS; ISRAEL; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANTS, MEDICINAL; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; STEREOISOMERISM; TAXOIDS; TAXUS;

TAXUS; TAXUS BACCATA;

EID: 1442334507     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np030311y     Document Type: Article

References (46)

1. Hook, I.; Poupat, C.; Ahond, A.; Guénard, D.; Guéritte, F. ; Adeline, M.-T.; Wang, X.-P.; Dempsey, D.; Breuillet, S.; Potier, P. Phytochemistry 1999, 52, 1041-1045.
2. Hartzell, H., Jr. The Yew Tree: A Thousand Whispers: Biography of a Species; Hulogosi: Eugene, OR, 1991; pp 1-319.
3. Denis, J. N.; Green, A. E.; Guénard, D.; Guéritte-Voegelin, F.; Mangatal, L.; Potier, P. J. Am. Chem. Soc. 1988, 110, 5917-5919.
4. Senilh, V.; Blechert, S.; Colin, M.; Guénard, D.; Picot, F.; Varenne, P. J. Nat. Prod. 1984, 47, 131-137.
5. Gabetta, B.; Orsini, P.; Peterlongo, F.; Appendino, G. Phytochemistry 1998, 47, 1325-1329.
6. Gabetta, B.; Bellis, P.; Pace, R.; Appendino, G.; Barboni, L.; Torregiani, E.; Gariboldi, P.; Viterbo, D. J. Nat. Prod. 1995, 58, 1508-1514.
7. Kingston, D. G. I.; Molinero, A. A.; Rimoldi, G. M. In Progress in the Chemistry of Organic Natural Products; Herz, W., Moore, R. E., Kirby, G. W., Steglich, W., Tamm, C., Eds.; Springer: Wien, 1993; Vol. 61, pp 1-206.
8. Appendino, G. In The Chemistry and Pharmacology of Taxol and Its Derivatives; Farina, V., Ed.; Amsterdam, 1995; Vol. 22, pp 1-53 and pp 55-101.
9. Baloglu, E.; Kingston, D. G. I. J. Nat. Prod. 1999, 62, 1448-1472.
10. Chmurny, G. N.; Paukstelis, J. V.; Alvarado, A. B.; McGuire, M. T.; Snader, K. M.; Muschik, G. M.; Hilton, B. D. Phytochemistry 1994, 34, 477-483.
11. Appendino, G.; Gariboldi, P.; Pisetta, A.; Bombardelli, E.; Gabetta, B. Phytochemistry 1992, 31, 4253-4257.
12. Baxter, J. N.; Lythgoe, B.; Scrowston, R. M.; Trippett, S. J. Chem. Soc. 1962, 2964-2971.
13. Chiang, H. C.; Woods, M. C.; Nakadaira, K.; Nakanishi, K. J. Chem. Soc., Chem. Commun. 1967, 1201-1202.
14. Sakai, J.; Sasaki, H.; Kosugi, K.; Zhang, S.; Hirata, N.; Hirose, K.; Tomida, A.; Tsuruo, T.; Ando, M. Heterocycles 2001, 54, 999-1009.
15. Woods, M. C.; Chiang, H. C.; Nakadaira, K.; Nakanishi, K. J. Am. Chem. Soc. 1968, 90, 522-523.
16. Kobayashi, J.; Inubushi, A.; Hosoyama, H.; Yoshida, N.; Sasaki, T.; Shigemori, H. Tetrahedron 1995, 51, 5971-5978.
17. Della Casa de Marcano, D. P.; Halsall, T. G. J. Chem. Soc., Chem. Commun. 1969, 1282-1283.
18. Erdtman, H.; Tsuno, K. Phytochemistry 1969, 8, 931-932.
19. Wang, X.; Shigemori, H.; Kobayashi, J. J. Nat. Prod. 1998, 61, 474-479.
20. Barboni, L.; Gariboldi, P.; Appendino, G.; Enriu, R.; Gabetta, B.; Bombardelli, E. Liebigs Ann. 1995, 345-349.
21. Shi, Q. W.; Dauriol, F.; Mamer, O.; Zamir, L. Bioorg. Med. Chem. 2003, 11, 293-303.
22. Shi, Q. W.; Oritani, T.; Horigucg, T.; Sugiyama, T.; Murakami; Yamada, T. Biosci. Biotechnol. Biochem. 1999, 63, 924-929.
23. Kosugi, K.; Sasaki, J.; Zhang, S.; Watanabe, Y.; Sasaki, H.; Suzuki, T.; Hagiwara, H.; Hirata, N.; Hirose, K.; Ando, M.; Tomida, A.; Tsuruo, T. Phytochemistry 2000, 54, 839-845.
24. Beutler, J. A.; Chmurny, G. M.; Look, S. A.; Witherup, K. M. J. Nat. Prod. 1991, 54, 893-897.
25. Zhang, Z.; Jia, Z.; Zhu, Z.; Cui, Y.; Wang. Q. Planta Med. 1990, 56, 293-294.
26. Yoshizaki, F.; Fuduka, M.; Hisamichi, S.; Ishida, T.; In, Y. Chem. Pharm. Bull. 1988, 36, 2098-2112.
27. Zamir, L.; Zhang, J.; Wu, J.; Sauriol, F.; Mamer, O. J. Nat. Prod. 1999, 62, 1268-1273.
28. Zamir, L.; Zhang, J.; Wu, J.; Sauriol, F.; Mamer, O. Tetrahedron 1999, 55, 14323-14340.
29. Zhang, Z.; Jia, Z. Phytochemistry 1990, 29, 3673-3675.
30. Hosoyama, H.; Inubushi, A.; Katasui, T.; Shigemori, H.; Kobayashi, J. Tetrahedron 1996, 52, 13145-13150.
31. Ma, W.; Stahlhut, R. W.; Adams, T. L.; Park, G. L.; Evans, W. A.; Blumenthal, S. G.; Gomez, G. A.; Nieder, M. H.è Hylands, P. J. J. Nat. Prod. 1994, 57, 1320-1325.
32. Chauviere, G.; Guenard, D.; Picot, F.; Senilh, V.; Potier, P. Acad. Sci. Paris, Ser. II 1981, 293, 501-503.
33. Della Casa de Marcano, D. P.; Halsall, T. G. J. Chem. Soc., Chem. Commun. 1975, 365-366.
34. Miller, R. W.; Powell, R. G.; Smith, C. R., Jr.; Arnold, E.; Clardy, J. J. Org. Chem. 1981, 46, 1469-1474.
35. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327.
36. McLaughlin, J. L.; Miller, R. W.; Powell, R. G., Jr.; Smith, C. R. J. Nat. Prod. 1981, 44, 312-319.
37. Rao, K. V.; Reddy, G. C.; Juchum, J. Phytochemistry 1996, 43, 439-442.
38. Shi, Q. W.; Oritani, T.; Sugiyama, T. Phytochemistry 1999, 52, 1559-1563.
39. Kobayashi, J.; Ogiwara, A.; Hosoyama, H.; Shigemori, H.; Yoshida, N.; Sasaki, T.; Li, Y.; Iwasaki, S.; Naito, M.; Tsuruo, T. Tetrahedron 1994, 50, 7401-7416.
40. Zamir, L. O.; Zhou, Z. H.; Caron, G.; Nedea, M. E.; Sauriol, F.; Mamer, O. J. Chem. Soc., Chem. Commun. 1995, 529-530.
41. Boulanger, Y.; Khiat, A.; Zhou, Z. H.; Caron, G.; Zamir, L. O. Tetrahedron 1996, 52, 8957-8968.
42. Fang, W. Fang, Q.; Liang, X.; Lu, Y.; Zheng, Q. Tetrahedron 1995, 51, 8483-8490.
43. Louis, H. D. J.; Erik, L. M.; van Rozendaal; Teris, A.; van Beek. J. Nat Prod. 1996, 59, 117-123.
44. Yoshizaki, F.; Madarame, M.; Takahashi, C.; Hisamichi, S. Shoyakugaku Zasshi 1986, 40, 429-432.
45. Appendino, G.; Tagliapietra, S.; Ozen, H. C.; Gariboldi, P.; Gabetta, B. ; Bombardelli, E. J. Nat. Prod. 1993, 56, 514-520.
46. Horiguchi, T.; Rithner, C. D.; Croteau, R.; Williams, R. M. Tetrahedron 2003, 59, 267-273.