Six new indole alkaloids from Gelsemium sempervirens Ait. f.

被引:41
作者
Kogure, N [1 ]
Nishiya, C [1 ]
Kitajima, M [1 ]
Takayama, H [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
基金
日本学术振兴会;
关键词
indole alkaloid; Gelsemium; structure elucidation; NMR; total synthesis; isomerization; solvent effect;
D O I
10.1016/j.tetlet.2005.06.136
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
One new yohimbane and five new sarpagine-type indole alkaloids were isolated from the radix of Gelsemium sempervirens Ait. f., and their structures were determined by spectroscopic analysis, chemical conversion or total synthesis. It was found that 2-acyl sarpagine-type alkaloids possessing an N-b-methyl group take a keto-amino structure or a transannular form in solution depending on the solvent. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5857 / 5861
页数:5
相关论文
共 12 条
  • [1] Synthesis of sempervirine, a pentacyclic anhydronium indole alkaloid
    Chatterjee, A
    Sahu, A
    Saha, M
    Banerji, J
    [J]. MONATSHEFTE FUR CHEMIE, 1996, 127 (12): : 1259 - 1262
  • [2] C-D RING CLEAVAGE OF DIHYDROCORYNANTHEINE DERIVATIVES - PARTIAL SYNTHESIS OF DIHYDROBURNAMICINE
    DOLBY, LJ
    SAKAI, S
    [J]. TETRAHEDRON, 1967, 23 (01) : 1 - &
  • [3] GORMAN M, 1964, TETRAHEDRON LETT, V5, P3105
  • [4] A DIRECTED METALATION ROUTE TO THE ZWITTERIONIC INDOLE ALKALOIDS - SYNTHESIS OF SEMPERVIRINE
    GRIBBLE, GW
    BARDEN, TC
    JOHNSON, DA
    [J]. TETRAHEDRON, 1988, 44 (11) : 3195 - 3202
  • [5] Structure reinvestigation of gelsemoxonine, a constituent of Gelsemium elegans, reveals a novel, azetidine-containing indole alkaloid
    Kitajima, M
    Kogure, N
    Yamaguchi, K
    Takayama, H
    Aimi, N
    [J]. ORGANIC LETTERS, 2003, 5 (12) : 2075 - 2078
  • [6] New oxindole alkaloids and iridoid from Carolina jasmine (Gelsemium sempervirens AIT. f.)
    Kitajima, M
    Urano, A
    Kogure, N
    Takayama, H
    Aimi, N
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (10) : 1211 - 1214
  • [7] A chemical study on "Yakatsu" stored in Shosoin repository - Isolation and characterization of four indole alkaloids from a 1250 year-old sample of the Chinese toxic medicine
    Kitajima, M
    Arai, Y
    Takayama, H
    Aimi, N
    [J]. PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES, 1998, 74 (07): : 159 - 163
  • [8] NEW SYNTHESES OF FLAVOPEREIRINE AND YOHIMBANES BY ENAMIDE PHOTOCYCLIZATION
    NINOMIYA, I
    TADA, Y
    KIGUCHI, T
    YAMAMOTO, O
    NAITO, T
    [J]. HETEROCYCLES, 1978, 9 (11) : 1527 - 1531
  • [9] STUDIES ON THE INDOLE ALKALOIDS OF GELSEMIUM-ELEGANS (THAILAND) - STRUCTURE ELUCIDATION AND PROPOSAL OF BIOGENETIC ROUTE
    PONGLUX, D
    WONGSERIPIPATANA, S
    SUBHADHIRASAKUL, S
    TAKAYAMA, H
    YOKOTA, M
    OGATA, K
    PHISALAPHONG, C
    AIMI, N
    SAKAI, S
    [J]. TETRAHEDRON, 1988, 44 (16) : 5075 - 5094
  • [10] TRANSFORMATION OF INDOLE ALKALOIDS .3. PARTIAL SYNTHESIS OF PROTOPINE TYPE INDOLE ALKALOID BURNAMICINE
    SAKAI, S
    YAMANAKA, E
    DOLBY, LJ
    [J]. YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1977, 97 (03): : 309 - 319