Cytotoxic lupane-type triterpenoids from Acacia mellifera

被引:70
|
作者
Mutai, C
Abatis, D
Vagias, C
Moreau, D
Roussakis, C
Roussis, V
机构
[1] Kenya Govt Med Res Ctr, Ctr Tradit Med & Drug Res, Nairobi, Kenya
[2] ISOMer, Lab Pharmacogenomique Marine, Fac Pharm, F-44035 Nantes, France
关键词
Acacia mellifera; Leguminosae; isolation; lupanes; 28-hydroxy-3-oxo-lup-20-(29)-en-30-al;
D O I
10.1016/j.phytochem.2004.03.002
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
One new and eight previously described lupane-type metabolites were isolated for the first time from Acacia mellifera (Leguminosae). Based on spectral analyses, the structure of the new compound was elucidated as 28-hydroxy-3-oxo-lup-20-(29)-en-30-al (1), while the known compounds were identified as 3-oxo-lup-20-(29)-en-30-al (2), 3-hydroxy-lup-20-(29)-en-30-al (3), 28-hydroxy-lup-20-(29)-en-3-one (4), lupenone (5), lupeol (6), betulin (7), betulinic acid (8), and betulonic acid (9). Metabolites 2, 3, and 4 are reported for the first time in the Leguminosae family. The cytotoxicity of the isolated metabolites was evaluated on the NSCLC-N6 cell line, derived from a human non-small-cell bronchopulmonary carcinoma. Compounds I and 3 exhibited significant levels of activity. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1159 / 1164
页数:6
相关论文
共 50 条
  • [1] Lupane triterpenoids from Acacia mellifera with cytotoxic activity
    Mutai, Charles
    Abatis, Dennis
    Vagias, Constantinos
    Moreau, Dimitri
    Roussakis, Christos
    Roussis, Vassilios
    [J]. MOLECULES, 2007, 12 (05): : 1035 - 1044
  • [2] Lupane-type triterpenoids from Acacia dealbata bark extracted by different methods
    Rodrigues, Vitor H.
    de Melo, Marcelo M. R.
    Portugal, Ines
    Silva, Carlos M.
    [J]. INDUSTRIAL CROPS AND PRODUCTS, 2021, 170
  • [3] Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents
    Gauthier, Charles
    Legault, Jean
    Lebrun, Maxime
    Dufour, Philippe
    Pichette, Andr
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (19) : 6713 - 6725
  • [4] Lupane-Type Triterpenoids from Schefflera octophylla
    Pang Su-qiu
    Sun Ai-jing
    Wang Guo-quan
    Xu Xian-xiang
    Xu Ruian
    [J]. CHEMISTRY OF NATURAL COMPOUNDS, 2016, 52 (03) : 432 - 435
  • [5] Cytotoxic Ceanothane- and Lupane-Type Triterpenoids from the Roots of Ziziphus jujuba
    Kang, Kyo Bin
    Kim, Jung Wha
    Oh, Won Keun
    Kim, Jinwoong
    Sung, Sang Hyun
    [J]. JOURNAL OF NATURAL PRODUCTS, 2016, 79 (09): : 2364 - 2375
  • [6] Lupane-Type Triterpenoids from Schefflera octophylla
    Pang Su-qiu
    Sun Ai-jing
    Wang Guo-quan
    Xu Xian-xiang
    Xu Ruian
    [J]. Chemistry of Natural Compounds, 2016, 52 : 432 - 435
  • [7] Lupane-type Triterpenoids from the Leaves of Heteropanax fragrans
    Zhao, Sanjun
    Huang, Zunxi
    Gao, Jing
    [J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (04): : 1368 - 1370
  • [8] Discovery of immunosuppressive Lupane-type Triterpenoids from Hypericum longistylum
    Yan, Shan
    Feng, Hao
    Sun, Lingjuan
    Shi, Zhengyi
    Hu, Hong
    Duan, Yulin
    Guo, Yi
    Tan, Xiaosheng
    Chen, Gang
    Qi, Changxing
    Zhang, Yonghui
    [J]. NATURAL PRODUCT RESEARCH, 2022, 36 (17) : 4394 - 4400
  • [9] Elesesterpenes A-K: Lupane-type Triterpenoids From the Leaves of Eleutherococcus sessiliflorus
    Han, Dong
    Liu, Yan
    Li, Xiao-Mao
    Wang, Si-Yi
    Sun, Yan
    Algradi, Adnan Mohammed
    Zou, Hai-Dan
    Pan, Juan
    Guan, Wei
    Kuang, Hai-Xue
    Yang, Bing-You
    [J]. FRONTIERS IN CHEMISTRY, 2022, 9
  • [10] Lupane-Type Triterpenoids and Sterol from Zizyphus Spina Christi Grown in Sudan
    Elnagar, Nawal Mohamed Ibrahim
    Modawi, Barakat Mohammed
    [J]. ORIENTAL JOURNAL OF CHEMISTRY, 2016, 32 (02) : 895 - 901