The aim of the study was to determine in vitro biological activity of fruit ethanol extract from Chaenomeles speciosa (Sweet) Nakai (Japanese quince, JQ) and its important constituents (−)-epicatechin (EC) and chlorogenic acid (CA). The study also investigated the structural changes in phosphatidylcholine (PC) liposomes, dipalmitoylphosphatidylcholine liposomes, and erythrocyte membranes (RBC) induced by the extract. It was found that the extract effectively inhibits oxidation of RBC, induced by 2,2′-azobis (2-amidinopropane) dihydrochloride (AAPH), and PC liposomes, induced by UVB radiation and AAPH. Furthermore, JQ extract to a significant degree inhibited the activity of the enzymes COX-1 and COX-2, involved in inflammatory reactions. The extract has more than 2 times greater activity in relation to COX-2 than COX-1 (selectivity ratio 0.48). JQ extract stimulated growth of the beneficial intestinal bacteria Lactobacillus casei and Lactobacillus plantarum. In the fluorimetric method by means of the probes Laurdan, DPH and TMA-DPH, and 1H-NMR, we examined the structural changes induced by JQ and its EC and CA components. The results show that JQ and its components induce a considerable increase of the packing order of the polar heads of lipids with a slight decrease in mobility of the acyl chains. Lipid membrane rigidification could hinder the diffusion of free radicals, resulting in inhibition of oxidative damage induced by physicochemical agents. JQ extract has the ability to quench the intrinsic fluorescence of human serum albumin through static quenching. This report thus could be of huge significance in the food industry, pharmacology, and clinical medicine.
This study was designed to evaluate the effects of purple potato extract of the Blue Congo variety (PP) on diabetes and its antioxidant activities after two-week administration tostreptozotocin (STZ)-induced diabetic rats. The activities of PP were evaluated at a dose of 165 mg/kg body weight (b.w.) by estimating biochemical changes in blood plasma and through a histopathological study of kidney, muscles, and liver tissue. We evaluated the effect of treatment with extract on glucose level, glycated hemoglobin, activities of enzymatic antioxidants (including superoxide dismutase, glutathione peroxidase, and catalase), and lipid peroxidation. Moreover, we determined advanced glycation end-products (AGEs), advanced oxidation protein products (AOPPs), and the level of oxidative modified proteins (OMPs) as markers of carbonyl-oxidative stress in rats with diabetes. Using high-performance liquid chromatography, we identified five anthocyanins and six phenolic acids in the extract from Blue Congo with the dominant acylated anthocyanin as petunidin-3-p-coumaroyl-rutinoside-5-glucoside. The administration of Blue Congo extract lowered blood glucose, improved glucose tolerance, and decreased the amount of glycated hemoglobin. Furthermore, PP demonstrated an antioxidative effect, suppressed malondialdehyde levels, and restored antioxidant enzyme activities in diabetic rats. After administration of PP, we also noticed inhibition of OMP, AGE, and AOPP formation in the rats′ blood plasma.
The synthesis of different classes of prenylated aglycones (α,β-dihydroxanthohumol (2) and (Z)-6,4’-dihydroxy-4-methoxy-7-prenylaurone (3)) was performed in one step reactions from xanthohumol (1)—major prenylated chalcone naturally occurring in hops. Obtained flavonoids (2–3) and xanthohumol (1) were used as substrates for regioselective fungal glycosylation catalyzed by two Absidia species and Beauveria bassiana. As a result six glycosides (4–9) were formed, of which four glycosides (6–9) have not been published so far. The influence of flavonoid skeleton and the presence of glucopyranose and 4-O-methylglucopyranose moiety in flavonoid molecule on binding to main protein in plasma, human serum albumin (HSA), and inhibition of cyclooxygenases COX-1 and COX-2 were investigated. Results showed that chalcone (1) had the highest binding affinity to HSA (8.624 × 104 M−1) of all tested compounds. It has also exhibited the highest inhibition of cyclooxygenases activity, and it was a two-fold stronger inhibitor than α,β-dihydrochalcone (2) and aurone (3). The presence of sugar moiety in flavonoid molecule caused the loss of HSA binding activity as well as the decrease in inhibition of cyclooxygenases activity.
We investigated the effects of acylated cyanidin-3-O-β-(6″-O-E-p-coumaroyl-sambubioside)-5-O-β-glucoside (C3cs-5G) and nonacylated cyanidin, cyanidin-3,5-di-O-β-glucoside (C3,5G) and cyanidin-3-O-β-glucoside (C3G), on cell-mimic membranes (MM) that reflected the membrane lipid composition of tumor cells. The relationship between structural derivatives of cyanidin (Cy-d), membrane interactivity, their antioxidant activity, and interaction with albumin were characterized. Studies showed that Cy-d caused an increase in packing order mainly in the hydrophilic region of the membranes. Cy-d have shown high antioxidant activity against liposome oxidation induced by AAPH and ability to bind to albumin through a static quenching mechanism. The results showed that glycosylation number and the presence of aromatic acid attached to sugars affected the membrane properties, according to the sequence C3-cs-5G > C3,5G > C3G. It can be stated that Cy-d in the process of interaction with MM caused a rigidifying effect, which is fundamental for understanding their anticancer and antioxidant activity and is one of the possible pharmaceutical mechanisms.
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