ACETOGENIC ISOQUINOLINE ALKALOIDS .35. (+/-)-DIONCOPHYLLACINE-A, A NAPHTHYLISOQUINOLINE ALKALOID WITH A 4-METHOXY SUBSTITUENT FROM THE LEAVES OF TRIPHYOPHYLLUM-PELTATUM

被引:14
作者
BRINGMANN, G
ORTMANN, T
ZAGST, R
SCHONER, B
ASSI, LA
BURSCHKA, C
机构
[1] UNIV ABIDJAN,CTR NATL FLORIST,CONSERVATOIRE & JARDIN BOT,ABIDJAN 22,COTE IVOIRE
[2] UNIV WURZBURG,INST INORGAN CHEM,W-8700 WURZBURG,GERMANY
关键词
TRIPHYOPHYLLUM-PELTATUM; DIONCOPHYLLACEAE; LEAVES; (+/-)-DIONCOPHYLLACINE-A; NAPHTHYLISOQUINOLINE ALKALOIDS; BIARYLS; NATURALLY OCCURRING; STRUCTURE ELUCIDATION;
D O I
10.1016/S0031-9422(00)97575-7
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The isolation and structure elucidation of rac-dioncophyllacine A from the leaves of Triphyophyllum peltatum, is described. Unlike all other naphthylisoquinoline alkaloids, this fully dehydrogenated representative has an additional methoxy group at C-4, the position of which is deduced from NOE results. Dioncophyllacine A has a 7,1'-site of the biaryl axis, as in dioncophylline A. Its constitution is confirmed by an X-ray structure analysis, which shows that the crystalline form of this new alkaloid is racemic.
引用
收藏
页码:4015 / 4018
页数:4
相关论文
共 21 条
  • [1] ACETOGENIC ISOQUINOLINE ALKALOIDS .17. 1ST TOTAL SYNTHESIS OF (-)-DIONCOPHYLLINE-A (TRIPHYOPHYLLINE) AND OF SELECTED STEREOISOMERS - COMPLETE (REVISED) STEREOSTRUCTURE
    BRINGMANN, G
    JANSEN, JR
    REUSCHER, H
    RUBENACKER, M
    PETERS, K
    VONSCHNERING, HG
    [J]. TETRAHEDRON LETTERS, 1990, 31 (05) : 643 - 646
  • [2] ACETOGENIC ISOQUINOLINE ALKALOIDS .23. STRUCTURE OF THE NAPHTHYL ISOQUINOLINE ALKALOID DIONCOPHYLLINE-A .22.
    BRINGMANN, G
    ZAGST, R
    SCHONER, B
    BUSSE, H
    HEMMERLING, M
    BURSCHKA, C
    [J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 : 1703 - 1705
  • [3] A 1ST AND GENERAL-ROUTE TO NAPHTHYLISOQUINOLINE ALKALOIDS - THE TOTAL SYNTHESIS OF O-METHYL-TETRADEHYDRO-TRIPHYOPHYLLINE
    BRINGMANN, G
    JANSEN, JR
    [J]. TETRAHEDRON LETTERS, 1984, 25 (24) : 2537 - 2540
  • [4] ACETOGENIC ISOQUINOLINE ALKALOIDS .34. ANCISTROBREVINE-B, THE 1ST NAPHTHYLISOQUINOLINE ALKALOID WITH A 5,8'-COUPLING SITE, AND RELATED-COMPOUNDS FROM ANCISTROCLADUS-ABBREVIATUS
    BRINGMANN, G
    ZAGST, R
    REUSCHER, H
    ASSI, LA
    [J]. PHYTOCHEMISTRY, 1992, 31 (11) : 4011 - 4014
  • [5] ACETOGENIC ISOQUINOLINE ALKALOIDS .24. DIONCOPELTINE-A AND DIONCOLACTONE-A - ALKALOIDS FROM TRIPHYOPHYLLUM-PELTATUM
    BRINGMANN, G
    RUBENACKER, M
    VOGT, P
    BUSSE, H
    ASSI, LA
    PETERS, K
    VONSCHNERING, HG
    [J]. PHYTOCHEMISTRY, 1991, 30 (05) : 1691 - 1696
  • [6] ACETOGENIC ISOQUINOLINE ALKALOIDS .16. ON THE STRUCTURE OF THE DIONCOPHYLLACEAE ALKALOIDS DIONCOPHYLLINE-A (TRIPHYOPHYLLINE) AND O-METHYL-TRIPHYOPHYLLINE
    BRINGMANN, G
    RUBENACKER, M
    JANSEN, JR
    SCHEUTZOW, D
    ASSI, LA
    [J]. TETRAHEDRON LETTERS, 1990, 31 (05) : 639 - 642
  • [7] ACETOGENIC ISOQUINOLINE ALKALOIDS .26. DIONCOPHYLLINE-B, A NAPHTHYLISOQUINOLINE ALKALOID WITH A NEW COUPLING TYPE FROM TRIPHYOPHYLLUM-PELTATUM
    BRINGMANN, G
    RUBENACKER, M
    GEUDER, T
    ASSI, LA
    [J]. PHYTOCHEMISTRY, 1991, 30 (11) : 3845 - 3847
  • [8] BRINGMANN G, 1991, LIEBIGS ANN CHEM, P803
  • [9] BRINGMANN G, 1991, PHYTOCHEMISTRY, V30, P2097
  • [10] BRINGMANN G, 1991, PLANTA MED, V57, P96