Planta Med 2000; 66(8): 746-748
DOI: 10.1055/s-2000-9566
Letters
© Georg Thieme Verlag Stuttgart · New York

Radical Scavenger Activity of Phenylethanoid Glycosides in FMLP Stimulated Human Polymorphonuclear Leukocytes: Structure-Activity Relationships

Jörg Heilmann1,*, Ihsan Çalis2 , Hasan Kirmizibekmez2 , Wolfgang Schühly1 , Sebnem Harput2 , Otto Sticher1
  • 1 Department of Applied BioSciences, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology (ETH) Zurich, Zürich, Switzerland
  • 2 Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey
Further Information

Publication History

Publication Date:
31 December 2000 (online)

Abstract

Radical scavenger activities of 21 phenylethanoid glycosides, including 15 ester derivatives of caffeic, ferulic, vanillic and syringic acid as well as 6 deacyl derivatives were determined by quantifying their effects on the production of reactive oxygen species (ROS) in a luminol-enhanced chemiluminescence assay with formyl-methionyl-leucyl-phenylalanine (FMLP) stimulated human polymorphonuclear neutrophils (PMNs). All phenylethanoids acylated with phenolic acids showed strong antioxidant activity whereas the deacyl derivatives were more than 30-fold less active. Therefore, the antioxidant activity is mainly related to the number of aromatic methoxy and hydroxy groups and the structure of the acyl moiety (C6-C1 or C6-C3). In contrast, modification of the sugar chain or replacement of hydroxy groups by methoxy groups in the acyl or the phenylethanoid moiety is of minor importance. The position of the acyl moiety is without significance. Free caffeic, ferulic, vanillic and syringic acid are less active compared to the phenylethanoid derivatives. This points to the importance of dissociation and lipophilicity of these acids in a cellular test system.

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Dr. Jörg Heilmann

Institute of Pharmaceutical Sciences, ETH Zurich

Winterthurerstrasse 190

8057 Zürich

Switzerland

Email: heilmann@pharma.ethz.ch

Phone: ++4116356049

Fax: ++4116356882