Turbinatine, a potential key intermediate in the biosynthesis of corynanthean-type indole alkaloids

被引:24
作者
Cardoso, CL
Silva, DHS
Tomazela, DM
Verli, H
Young, MCM
Furlan, M
Eberlin, MN
Bolzani, VD
机构
[1] Univ Estadual Paulista, UNESP, Inst Quim, BR-14801970 Sao Paulo, Brazil
[2] Univ Estadual Campinas, UNICAMP, Inst Quim, Thompson Mass Spect Lab, BR-13083970 Campinas, SP, Brazil
[3] Inst Bot, Secao Fisiol & Bioquim Plantas, BR-10051 Sao Paulo, SP, Brazil
[4] Univ Fed Rio Grande Sul, Ctr Biotecnol, UFRGS, BR-91501970 Porto Alegre, RS, Brazil
来源
JOURNAL OF NATURAL PRODUCTS | 2003年 / 66卷 / 07期
关键词
D O I
10.1021/np020547m
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Extraction of the leaves of Chimarrhis turbinata has led to the isolation of turbinatine (1), a new corynanthean-type indole alkaloid, besides four known indole alkaloids, strictosidine, 5alpha-carboxystrictosidine, vallesiachotamine, and isovallesiachotamine. The structural determination of 1 was based on 1D and 2D spectroscopic data. An evaluation of the DNA-damaging activities of the isolates was performed by means of a bioassay using mutant strains of Saccharomyces cerevisiae, which indicated these compounds were weakly active.
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页码:1017 / 1021
页数:5
相关论文
共 20 条
  • [1] Boom Brian M., 1991, Boletim do Museu Paraense Emilio Goeldi Serie Botanica, V7, P223
  • [2] Notes on calycophyllous Rubiaceae .1. Morphological comparisons of the genera Chimarrhis, Bathysa, and Calycophyllum, with new combinations and a new species, Chimarrhis gentryana
    Delprete, PG
    [J]. BRITTONIA, 1996, 48 (01) : 35 - 44
  • [3] DESILVA KTD, 1971, CHEM COMMUN, P905
  • [4] DESILVA KTD, 1971, CHEM COMMUN, P908
  • [5] BIOACTIVE ERGOST-5-ENE-3-BETA,7-ALPHA-DIOL DERIVATIVES FROM PSEUDOBERSAMA-MOSSAMBICENSIS
    GUNATILAKA, AAL
    SAMARANAYAKE, G
    KINGSTON, DGI
    HOFFMANN, G
    JOHNSON, RK
    [J]. JOURNAL OF NATURAL PRODUCTS, 1992, 55 (11): : 1648 - 1654
  • [6] HEMSCHEIDT T, 1985, PLANT CELL REP, V24, P216
  • [7] KUTCHAN TM, 1998, ALKALOIDS CHEM BIOL, P259
  • [8] Recent progress in the chemistry of monoterpenoid indole alkaloids derived from secologanin
    Leonard, J
    [J]. NATURAL PRODUCT REPORTS, 1999, 16 (03) : 319 - 338
  • [9] First direct and detailed stereochemical analysis of strictosidine
    PatthyLukats, A
    Karolyhazy, L
    Szabo, LF
    Podanyi, B
    [J]. JOURNAL OF NATURAL PRODUCTS, 1997, 60 (02): : 69 - 75
  • [10] Highly diastereoselective mercury-mediated synthesis of functionalized 2-azabicyclo[3.3.0]octane derivatives
    Peçanha, EP
    Verli, H
    Rodrigues, CR
    Barreiro, EJ
    Fraga, CAM
    [J]. TETRAHEDRON LETTERS, 2002, 43 (09) : 1607 - 1611