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Caffeic acid phenethyl ester (CAPE) analogues : potent nitric oxide inhibitors from the Netherlands propolis

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.1248/bpb.26.487
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FormatText, Article
Subjectcaffeic acid phenethyl ester; nitric oxide inhibitor; Netherlands propolis; murine macrophage-like J774.1 cell; antiinflammation
Abstract
The MeOH and water extracts of the Netherlands propolis were tested for their inhibitory activity toward nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage-like J774.1 cells. Both of the extract possessed significant NO inhibitory activity with IC50 values of 23.8 and 51.5 μg/ml, respectively. Then 13 phenolic compounds obtained from the MeOH extract showing stronger NO inhibition were examined on their NO inhibitory activities. Caffeic acid phenethyl ester (CAPE) analogues, i.e., benzyl caffeate, CAPE and cinnamyl caffeate, possessed most potent NO inhibitory activities with IC50 values of 13.8, 7.64 and 9.53 μM, respectively, which were two- to four-fold stronger than the positive control NG-monomethyl-L-arginine (L-NMMA; IC50, 32.9 μM). Further study on the synthetic analogues of CAPE revealed that both of 3-phenylpropyl caffeate (18; IC50, 7.34 μM) and 4-phenylbutyl caffeate (19; IC50, 6.77 μM) possessed stronger NO inhibitory activity than CAPE (10) and that elongation of alkyl side chain of alcoholic parts of caffeic acid esters enhance the NO inhibitory activity. In addition, it was found that CAPE analogues having longer carbon chain (>C5) in alcoholic part showed toxic effects toward J774.1 cells. This NO inhibitory effect may directly correlate with antiinflammatory properties of the Netherlands propolis.
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  • Biological and Pharmaceutical Bulletin 26, no. 4 (16 January 2003): 487–491.
LanguageEnglish
Peer reviewedYes
NRC publication
This is a non-NRC publication

"Non-NRC publications" are publications authored by NRC employees prior to their employment by NRC.

NPARC number21274441
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Record identifier26490cb1-3134-479a-94c0-fb57f3311759
Record created2015-03-13
Record modified2020-04-02
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