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酚酸对蘑菇抗炎活性的贡献:在酚类提取物、单个母体分子以及合成的葡萄糖醛酸化和甲基化衍生物中的筛选。

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.

作者信息

Taofiq Oludemi, Calhelha Ricardo C, Heleno Sandrina, Barros Lillian, Martins Anabela, Santos-Buelga Celestino, Queiroz Maria João R P, Ferreira Isabel C F R

机构信息

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.

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.

出版信息

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

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 (EC 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.

摘要

在本研究中,对14种可食用蘑菇的乙醇提取物在脂多糖(LPS)激活的RAW 264.7巨噬细胞中的抗炎潜力进行了研究。此外,还对提取物中的酚酸及相关化合物进行了化学表征。为了建立构效关系并了解体内代谢反应对化合物活性的影响,还对通过化学合成获得的已鉴定分子(对羟基苯甲酸、对香豆酸和肉桂酸)及其葡萄糖醛酸化和甲基化衍生物的相同生物活性进行了评估。平菇、高大环柄菇、皱柄牛肝菌和双孢蘑菇的提取物显示出最强的抗炎潜力(EC值为96±1至190±6μg/mL),肉桂酸浓度也最高(656至156μg/g),而肉桂酸也是具有最高抗炎活性的单个化合物。对香豆酸的衍生物显示出最强的特性,特别是羧基甲基化的衍生物(CoA-M1),其表现出与用作抗炎标准的地塞米松相似的活性;相比之下,对羟基苯甲酸的衍生物对一氧化氮产生的抑制作用最低。总而言之,虽然共轭反应会改变酚酸的化学结构,可能增加或降低其活性,但所研究化合物的葡萄糖醛酸化和甲基化衍生物仍具有抗炎活性。

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