Isolation of 2-arylbenzofurans and stilbenes with potential anti-inflammatory activity and their metabolism in model of colon microbiota

Stilbenes and benzofurans are common components of some food or content compounds of medicinal plants with antioxidant, chemoprotective and anti-inflammatory effect. The occurrence of the most well-known stilbene resveratrol is described for example in wine, peanuts, cocoa powder and different berries, the rich source of benzofuran derivatives is for example mulberry root [1,2].

Their activity is connected with interaction with multiple cellular targets, however, only limited information is known about their metabolism and interaction with gut microbiota. Therefore, our study is aimed to isolate natural stilbenes and benzofurans from plants, and to analyze their metabolism in a model of colon microbiota.

Several benzofurans and stilbenes were isolated from Morus alba root bark and Artocarpus heterophyllus using combination of different chromatographic techniques including preparative TLC and HPLC. These compounds were tested to analyze their anti-inflammatory activity, together with some commercially available stilbenoids.

Several stilbenoid compounds were subjected to metabolism in model of colon microbiota. The results obtained via LC-MS analysis of metabolic products showed the formation of total 19 metabolites. Surprisingly, no monocyclic stilbene metabolites were detected. The most intensive was metabolism of resveratrol and batatasin III, the most pronounced was formation of dihydroresveratrol from trans-resveratrol. The most common reaction observed was reduction of one meta localized hydroxy group, demethylation, double bond (bridge) oxidation or double bond reduction.

Authors thank to support of Grant Agency of Czech Republic (GAČR 16 – 07193S).

[1] Shen T, Wang XN, Lou HX. Nat Prod Rep 2009; 26: 916 – 935

[2] Khanam H, Uzzaman S. Eur J Med Chem 2015; 97: 483 – 504