Isolation and structural determination of a novel bicyclic taxane diterpene from needles of the chinese yew, taxu

Bioscience, Biotechnology and Biochemistry

Volumn 63, Issue 4, 1999, Pages 756-759

  Wen Shi, Qing ^a   Oritani, Takayuki ^a   Sugiyama, Takeyoshi ^a   Yamada, Teiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Bicyclic taxanes; Needles; Taxaceae; Taxoids; Taxus mairei

Indexed keywords

2,7,9,10,13,20 HEXAACETOXY 5 (2' ACETOXYCINNAMOYLOXY) 3,8 SECOTAXA 3,8,11 TRIENE; 2,7,9,10,13,20-HEXAACETOXY-5-(2'-ACETOXYCINNAMOYLOXY)-3,8-SECOTAXA-3,8,11-TRIENE; BICYCLO COMPOUND;

ARTICLE; CHEMISTRY; CHINA; CONFORMATION; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; INFRARED SPECTROPHOTOMETRY; ISOLATION AND PURIFICATION; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ULTRAVIOLET SPECTROPHOTOMETRY;

BICYCLO COMPOUNDS; CHINA; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PLANTS, MEDICINAL; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0033111033     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.63.756     Document Type: Article

References (15)

1. Appendino, G., The phytochemistry of the yew tree. Nat. Prod. Rep., 12, 349-360 (1995).
2. Kingston, D. G. I., Molinero, A. A., and Rimoldi, J. M., in “Progress in the Chemistry of Organic Natural Products” ed. by Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., and Tamm, C. H. Springer, 61, 1-206 (1993)
3. Shi, Q. W., Oritani, T., Kiyota, H., and Horiguchi, T., Isolation and structure elucidation of a new 11(15 1)-abeotaxanç from the Chinese yew, Taxus mairei. Nat. Prod. Lett., 12, 67-74 (1998).
4. Shi, Q. W., Oritani, T., and Sugiyama, T., A newly rearranged 2(3 ->20)-a&eotaxane diterpene from the bark of Chinese yew, Taxus mairei. Biosci. Biotechnol. Biochem., 62, 2263-2266 (1998).
5. Zamir, L. O., Zhou, Z. H., Carron, G., Nedea, M. E., Sauriol, F., and Zamer, C., Isolation of a putative biogenetic taxane precursor from Taxus Canadensis needles. J. Chem. Soc., Chem. Commun., 529-530 (1995).
6. Fang, W. S., Fang, Q. C., Liang, X. T., Lu, Y., and Zheng, Q. T., Taxachitrienes A and B, two new bicyclic taxane diterpenoids from Taxus chinensis. Tetrahedron, 51, 8483-8490 (1995).
7. Appendino, G., in “The Chemistry and Pharmacology of Taxol and Its Derivatives,” ed. by Farina, V. Amsterdam, 22, 55-102 (1995).
8. Fukushima, M., Fukamiya, N., Tagahara, K., Lee, K. H., and Okano, M., Study on chemical constituents of Taxus chinensis. 42nd Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Gifu, 281-283 (1998).
9. Shigemori, H., Wang, X. X., Yoshida, N., and Kobayashi, J., Taxuspines X-Z, new taxoids from Japanese yew Taxus cuspida-ta. Chem. Pharm. Bull, 45, 1205-1208 (1997).
10. Jackson, C. B., and Pattenden, G., Total synthesis of ver-ticillene, the putative biogenetic precursor of taxane alkaloids. Tetrahedron Lett., 26, 3393-3396 (1985).
11. Begley, M. J., Jackson, C. B., and Pattenden, G., Investigation of transannular cyclisations of verticillanes to the taxane ring system. Tetrahedron Lett., 26, 3397-3400 (1985).
12. Hosoyama, H., Inubushi, A., Katsui, T., Shigemori, H., and Kobayashi, J., Taxuspines U, V, and W, new taxane and related diterpenoids from the Japanese yew Taxus cuspidata. Tetrahedron, 52, 13145-13150 (1996).
13. Fang, W. S., Fang, Q. C., and Liang, X. T., Bicyclic taxoids from needles of Taxus chinensis. Planta Med., 62, 567-569 (1996).
14. Juéritte-Voegelein, F., Guénard, D., and Potier, P., Taxol and derivitives: a biogenetic hypothesis. J. Nat. Prod., 50, 9-18 (1987).
15. Hezari, M., and Croteau, R., Taxol biosythesis: an update. Planta Med., 63, 291-295 (1997)