Two stereoisomeric pentacyclic oxindole alkaloids from Uncaria tomentosa:: uncarine C and uncarine E

被引：10
|
作者：
Muhammad, I
Khan, IA
Fischer, NH
Fronczek, FR [1 ]
机构：
[1] Louisiana State Univ, Dept Chem, Baton Rouge, LA 70803 USA
[2] Univ Mississippi, Sch Pharm, Pharmaceut Sci Res Inst, Nat Ctr Nat Prod Res, University, MS 38677 USA
[3] Univ Mississippi, Sch Pharm, Pharmaceut Sci Res Inst, Dept Pharmacognosy, University, MS 38677 USA
来源：
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY | 2001年 / 57卷
关键词：
D O I：
10.1107/S0108270101000932
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The chloroform solvate of uncarine C (pteropodine), (1'S,3R,4'aS,5'aS,10'aS)-1,2,5',5' a,7',8',10',10' a-octahydro-1'-methyl-2-oxospiro[3H-indole-3,6' (4'aH)-[1H]pyrano[3,4-f]-indolizine]-4'-carboxylic acid methyl ester, C21H24N2O4. CHCl3,has an absolute configuration with the spiro C atom in the R configuration. Its epimer at the spiro C atom, uncarine E (isopteropodine), (1'S,3S,4'aS,5'aS,10'aS)-1,2,5',5' a,7',8',10',10' a-octahydro-1'-methyl-2-oxospiro[3H-indole-3,6'(4'aH)-[1H]pyrano[3,4-f]indolizine]-4'-carboxylic acid methyl ester, C21H24N2O4, has Z/ = 3, with no solvent. Both form intermolecular hydrogen bonds involving only the oxindole, with N . . .O distances in the range 2.759 (4)-2.894 (5) Angstrom.
引用
下载
收藏
页码：480 / 482
页数：3
相关论文
共 50 条
  • [21] Supercritical fluid extraction of oxindole alkaloids from Uncaria Tormentosa
    LopezAvila, V
    Benedicto, J
    Robaugh, D
    HRC-JOURNAL OF HIGH RESOLUTION CHROMATOGRAPHY, 1997, 20 (04): : 231 - 236
  • [22] NEW TYPE OXINDOLE ALKALOIDS IN UNCARIA SALACCENSIS FROM THAILAND
    PONGLUX, D
    WONGSERIPIPATANA, S
    AIMI, N
    ISHIKAWA, M
    HAGINIWA, J
    SAKAI, S
    JOURNAL OF PHARMACEUTICAL SCIENCES, 1987, 76 (11) : S195 - S195
  • [23] Binding of an oxindole alkaloid from Uncaria tomentosa to amyloid protein (Aβ1-40)
    Frackowiak, Teresa
    Baczek, Tomasz
    Kaliszan, Roman
    Zbikowska, Beata
    Glensk, Michal
    Fecka, Izabela
    Cisowski, Wojciech
    ZEITSCHRIFT FUR NATURFORSCHUNG C-A JOURNAL OF BIOSCIENCES, 2006, 61 (11-12): : 821 - 826
  • [24] Cytotoxic Effect of the Pentacyclic Oxindole Alkaloid Mitraphylline Isolated from Uncaria tomentosa Bark on Human Ewing's Sarcoma and Breast Cancer Cell Lines
    Garcia Gimenez, Dolores
    Garcia Prado, Elena
    Saenz Rodriguez, Teresa
    Fernandez Arche, Angeles
    De la Puerta, Rocio
    PLANTA MEDICA, 2010, 76 (02) : 133 - 136
  • [25] ALKALOIDS FROM UNCARIA-TOMENTOSA AND THEIR PHAGOCYTOSIS-INCREASING EFFECT
    WAGNER, H
    KREUTZKAMP, B
    JURCIC, K
    PLANTA MEDICA, 1985, 51 (05) : 419 - 423
  • [26] UNCARINE C D (SPECIOPHYLLINE) E AND F - C-3 AND C-7 EPIMERIC OXINDOLES RELATED TO TETRAHYDROALSTONINE
    HART, NK
    JOHNS, SR
    LAMBERTO.JA
    CHEMICAL COMMUNICATIONS, 1967, (02) : 87 - &
  • [27] Determination of relative configurations and conformations of oxindole alkaloids from Uncaria guianensis by NMR
    Carbonezi, CA
    Hamerski, L
    Flausino, OA
    Furlan, M
    Bolzani, VD
    Claudia, M
    Young, M
    QUIMICA NOVA, 2004, 27 (06): : 878 - 881
  • [28] Effect of oxindole alkaloids from the hooks of Uncaria macrophylla on thiopental-induced hypnosis
    Sakakibara, I
    Takahashi, H
    Terabayashi, S
    Yuzurihara, M
    Kubo, M
    Ishige, A
    Higuchi, M
    Komatsu, Y
    Okada, M
    Maruno, M
    Biqiang, C
    Jiang, HX
    PHYTOMEDICINE, 1998, 5 (02) : 83 - 86
  • [29] HPLC quantification of uncarine D and the anti-plasmodial activity of alkaloids from leaves of Mitragyna inermis (Willd.) O. Kuntze
    Fiot, J
    Baghdikian, A
    Boyer, L
    Mahiou, V
    Azas, N
    Gasquet, M
    Timon-David, P
    Balansard, G
    Ollivier, E
    PHYTOCHEMICAL ANALYSIS, 2005, 16 (01) : 30 - 33
  • [30] STRUCTURE AND SYNTHESIS OF 2 NEW TYPES OF OXINDOLE ALKALOIDS FOUND FROM UNCARIA-SALACCENSIS
    PONGLUX, D
    WONGSERIPIPATANA, S
    AIMI, N
    NISHIMURA, M
    ISHIKAWA, M
    SADA, H
    HAGINIWA, J
    SAKAI, S
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (02) : 573 - 575
12345