Ipomoeassins A-E, cytotoxic macrocyclic glycoresins from the leaves of Ipomoea squamosa from the Suriname rainforest

被引:69
作者
Cao, SG
Guza, RC
Wisse, JH
Miller, JS
Evans, R
Kingston, DGI
机构
[1] Virginia Polytech Inst & State Univ, Dept Chem, Blacksburg, VA 24061 USA
[2] Bedrijf Geneesmiddelen Voorziening Suriname, Geyersvlijt, Suriname
[3] Missouri Bot Garden, St Louis, MO 63166 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2005年 / 68卷 / 04期
关键词
D O I
10.1021/np049629w
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
The new glycoresins, ipomoeassins A-E (1-5), have been isolated from the leaves of Ipomoea squamosa. The structures were elucidated by spectroscopic analyses and chemical transformations. The absolute configurations of C-5 (ipomoeassins 3-5) and C-11 (ipomoeassins 1 and 2) were determined by their derivatives with (R)- and (S)-MPA. All the isolates were active in the A2780 human ovarian cancer cell line assay, and 4 showed the highest activity with an IC50 value of 35 nM.
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收藏
页码:487 / 492
页数:6
相关论文
共 13 条
  • [1] Bioactive natural products from traditionally used Mexican plants .5. Isolation and structural characterization of new glycolipid ester type dimers from the resin of Ipomoea tricolor (Convolvulaceae)
    Bah, M
    PeredaMiranda, R
    [J]. TETRAHEDRON, 1997, 53 (27) : 9007 - 9022
  • [2] Detailed FAB mass spectrometry and high resolution NMR investigations of Tricolorins A-E, individual oligosaccharides from the resins of Ipomoea tricolor (Convolvulaceae)
    Bah, M
    PeredaMiranda, R
    [J]. TETRAHEDRON, 1996, 52 (41) : 13063 - 13080
  • [3] Characterization of an anti-tuberculosis resin glycoside from the prairie medicinal plant Ipomoea leptophylla
    Barnes, CC
    Smalley, MK
    Manfredi, KP
    Kindscher, K
    Loring, H
    Sheeley, DM
    [J]. JOURNAL OF NATURAL PRODUCTS, 2003, 66 (11): : 1457 - 1462
  • [4] CHATURVEDULA VSP, IN PRESS J NAT PROD
  • [5] Orizabins V-VIII, tetrasaccharide glycolipids from the Mexican scammony root (Ipomoea orizabensis)
    Hernández-Carlos, B
    Bye, R
    Pereda-Miranda, R
    [J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (08): : 1096 - 1100
  • [6] Isolation and characterization of five new tetrasaccharide glycosides from the roots of Ipomoea stans and their cytotoxic activity
    León, I
    Enríquez, RDG
    Gnecco, D
    Villarreal, ML
    Cortés, DA
    Reynolds, WF
    Yu, M
    [J]. JOURNAL OF NATURAL PRODUCTS, 2004, 67 (09): : 1552 - 1556
  • [7] LOUIE KG, 1985, CANCER RES, V45, P2110
  • [8] NODA N, 1994, CHEM PHARM BULL, V42, P2011, DOI 10.1248/cpb.42.2011
  • [9] RESIN GLYCOSIDES .1. ISOLATION AND STRUCTURE ELUCIDATION OF ORIZABIN-I, ORIZABIN-II, ORIZABIN-III AND ORIZABIN-IV, GENUINE RESIN GLYCOSIDES FROM THE ROOT OF IPOMOEA-ORIZABENSIS
    NODA, N
    ONO, M
    MIYAHARA, K
    KAWASAKI, T
    OKABE, M
    [J]. TETRAHEDRON, 1987, 43 (17) : 3889 - 3902
  • [10] Biodynamic constituents in the Mexican morning glories: Purgative remedies transcending boundaries
    Pereda-Miranda, R
    Bah, M
    [J]. CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2003, 3 (02) : 111 - 131