Selective apoptosis-inducing activity of crinum-type Amaryllidaceae alkaloids

被引:96
作者
McNulty, James
Nair, Jerald J.
Codina, Carles
Bastida, Jaume
Pandey, Siyaram
Gerasimoff, Jenny
Griffin, Carly
机构
[1] McMaster Univ, Dept Chem, Hamilton, ON L8S 4M1, Canada
[2] Univ Barcelona, Fac Farm, Dept Nat Prod, E-08028 Barcelona, Spain
[3] Univ Windsor, Dept Chem & Biochem, Windsor, ON N9B 3P4, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
amaryllidaceae; apoptosis-induction; anticancer agent; alkaloid;
D O I
10.1016/j.phytochem.2007.01.006
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 selective apoptosis-inducing activity of Amaryllidaceae alkaloids belonging to the crinane-type is reported. A mini-library of natural and synthetic crinane alkaloids was assembled. Biological screening indicated crinamine 4 and haemanthamine 9 to be potent inducers of apoptosis in tumour cells at micromolar concentrations. Structure-activity relationships demonstrated the requirement for both an alpha-C2 bridge and a free hydroxyl at the C-11 position as pharmacophoric requirements for this activity. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1068 / 1074
页数:7
相关论文
共 24 条
  • [1] [Anonymous], 1968, AMARYLLIDACEAE ALKAL
  • [2] Alkaloids from South African Amaryllidaceae -: Part 7 -: Bioactive alkaloids from Brunsvigia radulosa
    Campbell, WE
    Nair, JJ
    Gammon, DW
    Codina, C
    Bastida, J
    Viladomat, F
    Smith, PJ
    Albrecht, CF
    [J]. PHYTOCHEMISTRY, 2000, 53 (05) : 587 - 591
  • [3] ALKALOIDS OF THE AMARYLLIDACEAE
    COOK, JW
    LOUDON, JD
    [J]. ALKALOIDS, 1952, 2 : 331 - 352
  • [4] Alkaloids from Cyrtanthus elatus
    Herrera, MR
    Machocho, AK
    Nair, JJ
    Campbell, WE
    Brun, R
    Viladomat, F
    Codina, C
    Bastida, J
    [J]. FITOTERAPIA, 2001, 72 (04) : 444 - 448
  • [5] Antiproliferative Amaryllidaceae alkaloids isolated from the bulbs of Sprekelia formosissima and Hymenocallis x festalis
    Hohmann, J
    Forgo, P
    Molnár, J
    Wolfard, K
    Molnár, A
    Thalhammer, T
    Máthé, I
    Sharples, D
    [J]. PLANTA MEDICA, 2002, 68 (05) : 454 - 457
  • [6] Acetylcholinesterase inhibitors from plants and fungi
    Houghton, PJ
    Ren, YH
    Howes, MJ
    [J]. NATURAL PRODUCT REPORTS, 2006, 23 (02) : 181 - 199
  • [7] INHIBITORS OF PROTEIN-SYNTHESIS IN EUKARYOTIC CELLS COMPARATIVE EFFECTS OF SOME AMARYLLIDACEAE ALKALOIDS
    JIMENEZ, A
    SANTOS, A
    ALONSO, G
    VAZQUEZ, D
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA, 1976, 425 (03) : 342 - 348
  • [8] Amaryllidaceae and Sceletium alkaloids
    Jin, Z
    [J]. NATURAL PRODUCT REPORTS, 2005, 22 (01) : 111 - 126
  • [9] Pancratistatin causes early activation of caspase-3 and the flipping of phosphatidyl serine followed by rapid apoptosis specifically in human lymphoma cells
    Kekre, N
    Griffin, C
    McNulty, J
    Pandey, S
    [J]. CANCER CHEMOTHERAPY AND PHARMACOLOGY, 2005, 56 (01) : 29 - 38
  • [10] TRADITIONAL MEDICINAL-PLANTS OF THAILAND .22. CYTOTOXIC AND ANTIMALARIAL ALKALOIDS FROM THE BULBS OF CRINUM-AMABILE
    LIKHITWITAYAWUID, K
    ANGERHOFER, CK
    CHAI, HB
    PEZZUTO, JM
    CORDELL, GA
    [J]. JOURNAL OF NATURAL PRODUCTS, 1993, 56 (08): : 1331 - 1338