• Title of article

    Structure–activity relationships of 1′S-1′-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages

  • Author/Authors

    Hisashi Matsuda، نويسنده , , Shin Ando، نويسنده , , Toshio Morikawa، نويسنده , , Shinya Kataoka، نويسنده , , Masayuki Yoshikawa، نويسنده ,

  • Issue Information
    روزنامه با شماره پیاپی سال 2005
  • Pages
    5
  • From page
    1949
  • To page
    1953
  • Abstract
    1′S-1′-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC50 value of 2.3 μM. To clarify the structure–activity relationship of 1′S-1′-acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic phenylbutanoids were examined, and the following structural requirements were clarified. (1) The para or ortho substitution of the acetoxyl and 1-acetoxypropenyl groups at the benzene ring was essential. (2) The S configuration of the 1′-acetoxyl group was preferable. (3) The presence of the 3-methoxyl group and disappearance of the 2′–3′ double bond by hydrogenation reduced the activity. (4) The substitution of acetyl groups with propionyl or methyl groups reduced the activity. (5) Lengthening of the carbon chain between the 1′- and 2′-positions reduced the activity.
  • Keywords
    1?S-1?-Acetoxychavicol acetate , structure–activity relationship , nitric oxide production , Lipopolysaccharide , macrophage , Phenylpropanoid
  • Journal title
    Bioorganic & Medicinal Chemistry Letters
  • Serial Year
    2005
  • Journal title
    Bioorganic & Medicinal Chemistry Letters
  • Record number

    795510