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Food Res Int. 2015 Oct;76(Pt 3):821-827. doi: 10.1016/j.foodres.2015.07.044. Epub 2015 Aug 3.

The contribution of phenolic acids to the anti-inflammatory activity of mushrooms: Screening in phenolic extracts, individual parent molecules and synthesized glucuronated and methylated derivatives.

Author information

1
Mountain Research Centre (CIMO), ESA, Polytechnic Institute of Bragança, Campus de Santa Apólónia, 1152, 5301-855 Bragança, Portugal; GIP-USAL, Faculty of Pharmacy, University of Salamanca, Campus Miguel de Unamuno, 37007 Salamanca, Spain.
2
Mountain Research Centre (CIMO), ESA, Polytechnic Institute of Bragança, Campus de Santa Apólónia, 1152, 5301-855 Bragança, Portugal; Center of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal.
3
Mountain Research Centre (CIMO), ESA, Polytechnic Institute of Bragança, Campus de Santa Apólónia, 1152, 5301-855 Bragança, Portugal.
4
GIP-USAL, Faculty of Pharmacy, University of Salamanca, Campus Miguel de Unamuno, 37007 Salamanca, Spain.
5
Center of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal.

Abstract

In the present study, the ethanolic extracts of fourteen edible mushrooms were investigated for their anti-inflammatory potential in LPS (lipopolysaccharide) activated RAW 264.7 macrophages. Furthermore the extracts were chemically characterized in terms of phenolic acids and related compounds. The identified molecules (p-hydroxybenzoic, p-coumaric and cinnamic acids) and their glucuronated and methylated derivatives obtained by chemical synthesis were also evaluated for the same bioactivity, in order to establish structure-activity relationships and to comprehend the effects of in vivo metabolism reactions in the activity of the compounds. The extracts of Pleurotus ostreatus, Macrolepiota procera, Boletus impolitus and Agaricus bisporus revealed the strongest anti-inflammatory potential (EC50 values 96±1 to 190±6μg/mL), and also the highest concentration of cinnamic acid (656 to 156μg/g), which was also the individual compound with the highest anti-inflammatory activity. The derivatives of p-coumaric acid revealed the strongest properties, specially the derivative methylated in the carboxylic group (CoA-M1) that exhibited similar activity to the one showed by dexamethasone used as anti-inflammatory standard; by contrast, the derivatives of p-hydroxybenzoic revealed the lowest inhibition of NO production. All in all, whereas the conjugation reactions change the chemical structure of phenolic acids and may increase or decrease their activity, the glucuronated and methylated derivatives of the studied compounds are still displaying anti-inflammatory activity.

KEYWORDS:

Anti-inflammatory; Edible mushrooms; Glucuronated and methylated derivatives; HPLC–PDA; Nitric oxide production; Phenolic acids

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