Structure-activity relationships of 1'S-1'-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages.
Hisashi Matsuda, Shin Ando, Toshio Morikawa, Shinya Kataoka, Masayuki Yoshikawa
Index: Bioorg. Med. Chem. Lett. 15 , 1949-53, (2005)
Full Text: HTML
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 IC(50) value of 2.3 microM. 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.
Related Compounds
Related Articles:
Aptamer-based polyvalent ligands for regulated cell attachment on the hydrogel surface.
2015-04-13
[Biomacromolecules 16(4) , 1382-9, (2015)]
Polymerization of affinity ligands on a surface for enhanced ligand display and cell binding.
2014-12-08
[Biomacromolecules 15(12) , 4561-9, (2014)]
2014-10-01
[Eur. J. Pharm. Biopharm. 88(2) , 406-14, (2014)]
Use of an enzyme-assisted method to improve protein extraction from olive leaves.
2015-02-15
[Food Chem. 169 , 28-33, (2014)]
2015-04-30
[Int. J. Pharm. 484(1-2) , 283-91, (2015)]