arachidin-1 and 3-3--4-5--tetrahydroxystilbene

Peanut (Arachis hypogaea) produces stilbenoids upon exposure to abiotic and biotic stresses. Among these compounds, the prenylated stilbenoids arachidin-1 and arachidin-3 have shown diverse biological activities with potential applications in human health. These compounds exhibit higher or novel biological activities in vitro when compared to their nonprenylated analogues piceatannol and resveratrol, respectively. However, assessment of these bioactivities in vivo has been challenging because of their limited availability. In this study, hairy root cultures of peanut were induced to produce stilbenoids upon treatment with elicitors. Co-treatment with 100 μM methyl jasmonate (MeJA) and 9 g/L methyl-β-cyclodextrin (CD) led to sustained high levels of resveratrol, piceatannol, arachidin-1, and arachidin-3 in the culture medium when compared to other elicitor treatments. The average yields of arachidin-1 and arachidin-3 were 56 and 148 mg/L, respectively, after co-treatment with MeJA and CD. Furthermore, MeJA and CD had a synergistic effect on resveratrol synthase gene expression, which could explain the higher yield of resveratrol when compared to treatment with either MeJA or CD alone. Peanut hairy root cultures were shown to be a controlled and sustainable axenic system for the production of the diverse types of biologically active stilbenoids.

Topics: Acetates; Arachis; beta-Cyclodextrins; Cell Culture Techniques; Culture Media; Cyclopentanes; Gene Expression Regulation, Plant; Hemiterpenes; Oxylipins; Plant Growth Regulators; Plant Proteins; Plant Roots; Resveratrol; Stilbenes

Biological activities of peanut stilbenoids, mainly resveratrol and its derivatives, have attracted increased attention and interest because of peanut being a potent producer and a dietary channel to convey these polyphenols to the human body. As arachidin-1 and piceatannol are structurally close to resveratrol, it is worthy to investigate their immunological activities on inhibition of lipopolysaccharide (LPS)-induced production of PGE2 and NO and mediation of the related transcription factors (NF-kappaB and C/EBP) of RAW 264.7 macrophage cells. Productions of PGE2 and NO were inhibited by all the test stilbenoids in a dose-dependent manner while gene and protein expressions of COX-2 and iNOS were not inhibited. As shown by NF-kappaB-driven luciferase assay, LPS-induced NF-kappaB activities were also reduced by the stilbenoids. In further, when these stilbenoids were subjected to monitoring their inhibitory effectiveness on LPS-induced transcription factor expressions of C/EBPdelta and C/EBPbeta, only C/EBPdelta expressions were reduced. Thus, these stilbenoids were effective in inhibition of PGE2- or NO-mediated inflammation and NF-kappaB- or C/EBPdelta-mediated inflammatory gene expression. In comparison, the highest inhibitory activity on LPS-induced PGE2/NO production, C/EBPdelta gene expression, and NF-kappaB activation was piceatannol which was followed in order by arachidin-1 and resveratrol. The observed anti-inflammatory activities of these peanut stilbenoids are of merit in further consideration for nutraceutical applications.

Topics: Animals; Anti-Inflammatory Agents; Arachis; Cell Line; Inflammation; Lipopolysaccharides; Macrophages; Mice; Resveratrol; Stilbenes