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Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages.

Abstract：

:Caffeic acid esters, one of the components of propolis, are known to show a variety of biological effects such as anti-tumor, anti-oxidant, and anti-inflammatory activities. Although, the anti-inflammatory activities of caffeic acid esters have been studied by analyzing their structure, the detailed mechanisms of their activities remain unclear. Thus, in this study, we examined the function of the ester functional group and the alkyl side chain (alcoholic part) and transformed caffeic acid to several derivatives. The inhibitory effect of these derivatives on NO production in murine macrophage RAW264.7 cells was dependent on the length and size of the alkyl moiety, and undecyl caffeate was the most potent inhibitor of NO production. In addition, individual experiments using undecanol, caffeic acid, undecanol plus caffeic acid, and undecyl caffeate showed that the connection between caffeic acid and the alkyl chain is critical for activity. Amide and ketone derivatives showed that not only the ester functional group but also the amide and ketone functional groups exhibit an inhibitory effect on NO production.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Uwai K,Osanai Y,Imaizumi T,Kanno S,Takeshita M,Ishikawa M

doi

10.1016/j.bmc.2008.07.006

subject

Has Abstract

pub_date

2008-08-15 00:00:00

pages

7795-803

issue

16

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(08)00603-2

journal_volume

16

pub_type

杂志文章

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