Synthesis and anti-inflammatory activity of indole glucosinolates

被引:41
|
作者
Vo, Quan V. [1 ]
Trenerry, Craige [2 ]
Rochfort, Simone [3 ,4 ]
Wadeson, Jenny [3 ]
Leyton, Carolina [3 ]
Hughes, Andrew B. [1 ]
机构
[1] La Trobe Univ, Dept Chem, Bundoora, Vic 3086, Australia
[2] Knoxfield Ctr, Dept Primary Ind, Knoxfield 3180, Australia
[3] Victorian AgriBiosci Ctr, Dept Primary Ind, Bundoora, Vic 3083, Australia
[4] La Trobe Univ, Bundoora, Vic 3086, Australia
关键词
Indole glucosinolates; Anti-inflammatory; Brassica; TNF-alpha; Glucobrassicin; 1-METHOXYINDOLES; CHEMISTRY;
D O I
10.1016/j.bmc.2013.12.003
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 nitronate and nitrovinyl methods to synthesize indole glucosinolates (GLs) have been investigated. The results were applied to generally the most prevalent natural indole glucosinolates to synthesize 4-methoxyglucobrassicin (MGB) and neo-glucobrassicin (NGB) in moderate overall yield for the first time. The anti-inflammatory activity of the synthetic indole GLs was determined by inhibition of TNF-alpha secretion in LPS-stimulated THP-1 cells. The data showed that glucobrassicin (GB) exhibited higher activity than other synthetic indolyl GLs. (C) 2013 Elsevier Ltd. All rights reserved.
引用
下载
收藏
页码:856 / 864
页数:9
相关论文
共 50 条
  • [41] Synthesis and anti-inflammatory activity of some pyrazole derivatives
    Samir M. El-Moghazy
    Flora F. Barsoum
    Hamdy M. Abdel-Rahman
    Adel A. Marzouk
    Medicinal Chemistry Research, 2012, 21 : 1722 - 1733
  • [42] SYNTHESIS AND ANTI-INFLAMMATORY ACTIVITY OF "ORTHO-CARBOXYPHENYLAMINOPYRIMIDINES
    KARP, VK
    TATYANCHENKO, IS
    PORTNYAGINA, VA
    MOKHORT, NA
    RYABUKHA, TK
    VINNIKOVA, AV
    KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1983, 17 (11): : 1304 - 1307
  • [43] The synthesis and anti-inflammatory activity of quinopimaric acid derivatives
    Kazakova, O. B.
    Tret'yakova, E. V.
    Smirnova, I. E.
    Spirikhin, L. V.
    Tolstikov, G. A.
    Chudov, I. V.
    Bazekin, G. V.
    Ismagilova, A. F.
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2010, 36 (02) : 257 - 262
  • [44] Synthesis of licochalcone analogues with increased anti-inflammatory activity
    Kim, Si-Jun
    Kim, Cheol Gi
    Yun, So-Ra
    Kim, Jin-Kyung
    Jun, Jong-Gab
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (01) : 181 - 185
  • [46] Synthesis and anti-inflammatory activity of fluorinated chalcone derivatives
    Jadhav, Dhanaji H.
    Ramaa, C. S.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2007, 46 (12): : 2064 - 2067
  • [47] Simple Synthesis of Modafinil Derivatives and Their Anti-inflammatory Activity
    Jung, Jae-Chul
    Lee, Yeonju
    Son, Jee-Young
    Lim, Eunyoung
    Jung, Mankil
    Oh, Seikwan
    MOLECULES, 2012, 17 (09) : 10446 - 10458
  • [48] Synthesis and anti-inflammatory activity of the major metabolites of imrecoxib
    Feng, Zhiqiang
    Chu, Fengming
    Guo, Zongru
    Sun, Piaoyang
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (08) : 2270 - 2272
  • [49] Synthesis and anti-inflammatory activity of acetylsalicylamino acids and peptides
    Khalikov, Sh. Kh.
    Kodirov, M.
    Alieva, S. V.
    CHEMISTRY OF NATURAL COMPOUNDS, 2006, 42 (02) : 204 - 207
  • [50] Synthesis and anti-inflammatory activity of fluorinated propanedione derivatives
    More, Arpita H.
    Ramaa, C. S.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2010, 49 (03): : 364 - 367