betadex 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

Piceatannol is one of resveratrol derivatives having health promoting potential. However, its low water-solubility and bioavailability could limit its use in both food and pharmaceutical fields. The aim of this work is the study of piceatannol complexation by β-cyclodextrin (β-CD) in aqueous media. The complex formed could improve the bioavailability, the solubility and the stability of piceatannol. The method used was based on RP-HPLC in which, β-CD was added to methanol/water mixtures mobile phases. The apparent formation constant of piceatannol/β-cyclodextrin complex was determined. Within the concentration interval studied (0-4 mM), whenever the concentration of β-CD increased, retention time of piceatannol decreased; indicating an enhancement of solubility due to the formation of the piceatannol/β-CD complex. The formation constants (KF) of the piceatannol/β-CD complex varied significantly with both the methanol concentration in the water-methanol mixture and the temperature. Moreover, in all the physicochemical conditions tested, the stoichiometry of piceatannol/β-CD complex was 1:1. Finally, the thermodynamic parameters were determined: ΔG°=-13.123 kJ mol(-1), ΔH°=-33. 265 kJ mol(-1) and ΔS°=-67.559 J mol(-1) K(-1).

Topics: beta-Cyclodextrins; Chromatography, High Pressure Liquid; Resveratrol; Stilbenes; Thermodynamics