Five novel taxanes from Taxus canadensis

被引:24
|
作者
Zamir, LO
Zhang, JZ
Wu, JH
Sauriol, F
Mamer, O
机构
[1] Univ Quebec, Inst Armand Frappier, INRS, Laval, PQ H7N 4Z3, Canada
[2] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
[3] McGill Univ, Biomed Mass Spectrometry Unit, Montreal, PQ H3A 1A3, Canada
来源
JOURNAL OF NATURAL PRODUCTS | 1999年 / 62卷 / 09期
关键词
D O I
10.1021/np990160s
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Five novel taxanes (1-5) have been isolated from the needles of Taxus canadensis, and their structures were elucidated on the basis of spectroscopic data. Two of these taxanes have structural features seldom found in yews, with a C-12, C-13 double bond and a hydroxymethylene at C-4. In addition, the 2D structures generated by molecular modeling of taxanes 1 and 2, differing mostly in the location of the double bond in ring A, were compared. The different conformation of ring A derived from the C-12, C-13 double band is particularly interesting because it implies that if a Taxol (paclitaxel) side chain were attached to C-13 it would have a different orientation from that in paclitaxel.
引用
收藏
页码:1268 / 1273
页数:6
相关论文
共 50 条
  • [41] NEW TAXANES FROM TAXUS-BREVIFOLIA
    KINGSTON, DGI
    HAWKINS, DR
    OVINGTON, L
    JOURNAL OF NATURAL PRODUCTS, 1982, 45 (04): : 466 - 470
  • [42] Rearranged taxanes from the bark of Taxus yunnanensis
    Li, SH
    Zhang, HJ
    Yao, P
    Sun, HD
    Fong, HHS
    JOURNAL OF NATURAL PRODUCTS, 2000, 63 (11): : 1488 - 1491
  • [43] Intramolecular transesterified taxanes from Taxus yunnanensis
    Zhang, HJ
    Mu, Q
    Xiang, W
    Yao, P
    Sun, HD
    Takeda, Y
    PHYTOCHEMISTRY, 1997, 44 (05) : 911 - 915
  • [44] TAXANES FROM THE SEEDS OF TAXUS-BACCATA
    APPENDINO, G
    TAGLIAPIETRA, S
    OZEN, HC
    GARIBOLDI, P
    GABETTA, B
    BOMBARDELLI, E
    JOURNAL OF NATURAL PRODUCTS, 1993, 56 (04): : 514 - 520
  • [45] Taxpropellane: A Novel Taxane with an Unprecedented Polycyclic Skeleton from the Needles of Taxus canadensis
    Zhang, Man-Li
    Dong, Mei
    Huo, Chang-Hong
    Li, Li-Geng
    Sauriol, Francoise
    Shi, Qing-Wen
    Gu, Yu-Cheng
    Makabe, Hidefumi
    Kiyota, Hiromasa
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (32) : 5414 - 5417
  • [46] A new taxane from Taxus canadensis needles
    Manli Zhang
    Zhiyu Ni
    Yufang Wang
    Mei Dong
    Ligeng Li
    Francoise Sauriol
    Changhong Huo
    Qingwen Shi
    Yucheng Gu
    Chemistry of Natural Compounds, 2012, 47 : 911 - 913
  • [47] A NEW TAXANE FROM Taxus canadensis NEEDLES
    Zhang, Manli
    Ni, Zhiyu
    Wang, Yufang
    Dong, Mei
    Li, Ligeng
    Sauriol, Francoise
    Huo, Changhong
    Shi, Qingwen
    Gu, Yucheng
    CHEMISTRY OF NATURAL COMPOUNDS, 2012, 47 (06) : 911 - 913
  • [48] Rearrangment of the major taxane from Taxus canadensis
    Zamir, LO
    Cherestes, AD
    Nikolakakis, A
    Sauriol, F
    Mamer, O
    TETRAHEDRON LETTERS, 1999, 40 (45) : 7917 - 7920
  • [49] A pair of taxoids from the needles of Taxus canadensis
    Yang, Chun
    Wang, Jun-Song
    Luo, Jian-Guang
    Kong, Ling-Yi
    JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2009, 11 (06) : 534 - 538
  • [50] A Novel Taxane 13-Glucoside and Other Taxanes from the Leaves of Taxus cuspidata
    Ni, Zhi-Yu
    Dong, Mei
    Cong, Bin
    Sauriol, Francoise
    Zhang, Man-Li
    Wang, Yu-Fang
    Huo, Chang-Hong
    Shi, Qing-Wen
    Kiyota, Hiromasa
    PLANTA MEDICA, 2011, 77 (03) : 281 - 283