Abstract
BackgroundThe isoflavonoid genistein represents the major active compound from soybean, the vegetal product from Glycine max (Fabaceae). The aim of this study is to prove that genistein was incorporated in two semisynthetic cyclodextrins, beta-cyclodextrin derivatives: hydroxypropyl-beta-cyclodextrin and randomly-methylated-beta-cyclodextrin as well as to compare the anti-inflammatory activity of genistein with that of genistein incorporated in these two types of semisynthetic cyclodextrins.ResultsThe animal studies were conducted on 8-week old C57BL/6 J female mice. Inflammation was induced in both ears of each mouse by topical application of 10 micrograms 12-O-tetradecanoylphorbol-3-acetate dissolved in 0.1 ml solvent (acetone : dimethylsulfoxide in a molar ratio 9:1). Thirty minutes later treatment was applied. The inflammatory reaction was correlated with increased values in ear thickness. Treatment with genistein and genistein incorporated in the two cyclodextrins led to decreased values for ear thickness. Better anti-inflammatory action was found for the complexes of genistein. Both haematoxylin-eosin analysis and CD45 marker expression are in agreement with these findings.ConclusionsResults allow concluding that genistein is an active anti-inflammatory phytocompound and its complexation with hydrophilic beta-cyclodextrin derivatives leads to a stronger anti-inflammatory activity.
Highlights
The isoflavonoid genistein represents the major active compound from soybean, the vegetal product from Glycine max (Fabaceae)
The aim of this study is to compare the anti-inflammatory activity of genistein with the one of genistein incorporated in two ramified beta-cyclodextrins: hydroxypropyl-;betacyclodextrin (HPBCD) and randomly–metylated-beta-cyclodextrin (RAMEB); cyclodextrin-genistein products were physical-chemically analysed by X-ray diffraction, thermal analysis and electronic microscopy in order to evaluate the formation of real inclusion complexes
Genistein-β-CD complexes were previously prepared, as reported in the literature [15], mainly through the insertion of the guest A-ring into the cyclodextrin cavity
Summary
The isoflavonoid genistein represents the major active compound from soybean, the vegetal product from Glycine max (Fabaceae). Flavonoids (flavus = yellow) are a class of secondary plant metabolites which function mainly as vegetal pigments, as antibiotic defence substances and as signal molecules for beneficial micro organisms in the rhizosphere [1]. The isoflavonoid genistein (Gen) (4,’ 5, 7-trihydroxyisoflavone) (Figure 1), the aglycone of the heterosidegenistin, Inflammation is a localized reaction of tissues in response to an aggressive action, characterized by redness, warmth, swelling, pain, and sometimes loss of mobility or function. Previous studies have demonstrated that genistein and other flavonoids exhibit an antiinflammatory effect both for human and mouse skin, as well as inhibitory action against the activation of nuclear factor-kB and secretory phospholipase A2 [9,10,11]
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