Complexes of Glucosamine Hydrochloride and Phytic Acid in Aqueous Medium and Their Antioxidant Properties in Human Blood Plasma

Abstract

The reaction in aqueous medium of phytic acid (myo-inositol hexakisphosphate) and glucosamine hydrochloride (2-amino-2-deoxy-b-D-glucopyranose hydrochloride) formed phytic acid-glucosamine complexes of formula InsP 6 × 5GA. Their compositions were proved by elemental analysis for C, H, N, and P. IR, PMR, 13 C NMR, and 31 P NMR spectroscopy and potentiometric titration showed that the complexes of phytic acid and glucosamine were formed by H-bonds and electrostatic salt interactions. High antioxidant activity against lipid peroxidation and a positive effect on superoxide dismutase activity were found for complexes of InsP 6 H 12 and glucosamine in in vitro studies of human blood plasma under oxidative stress.Metabolic disruptions of bone and connective tissues, in particular in collagen and cartilage matrices, are responsible for inflammatory and degenerative changes and are caused by the formation of reactive oxygen species, activation of lipid peroxidation (LPO), deactivation of enzymes such as superoxide dismutase (SOD), and the development of oxidative stress [1 -4].Preparations of glucosamine salts (chloride or sulfate) are known to inhibit the formation of malondialdehyde and diene conjugates, i.e., intermediate steps in the oxidation of collagen that underlie the biochemical and biophysical destruction of the cartilage matrix [5]. Multi-year experience showed that glucosamine (I) played a positive role in decreasing cartilage collagen degradation that resulted from excessive LPO and protein oxidation [6]. As a rule, preparations of I are used in combination with chondroitin in order to increase the activity of antioxidant enzymes such as SOD and catalase [7].Recently, the natural antioxidant phytic acid (myo-inositol hexakisphosphate, II, InsP 6 H 12 ) has generated much interest. It is a phosphorylated sugar that regulates metabolic processes, including Ca-P and ion balance in bone and connective tissues, and is involved in maintaining energy production in the human body [8][9][10]. It is commonly thought that the antioxidant effect of II is due mainly to inhibition of xanthine oxidase, which generates superoxide anion O 2 ·-, and activation of SOD [11]. It should be expected that II is capable not only of causing a synergic antioxidant effect in preparations of I but also of correcting more completely metabolic disruptions due to collagen-associated diseases.The goals of the present work were to study the formation in aqueous medium of complexes of I hydrochloride and II and to evaluate the antioxidant properties of the resulting complexes using parameters such as the LPO level, total antioxidant activity (AOA), and SOD activity with ozone-induced oxidative stress.

Agaricus bisporus-Derived Glucosamine Hydrochloride Regulates VEGF through BMP Signaling to Promote Zebrafish Vascular Development and Impairment Repair

“…It is endogenous biosynthesis in animals and humans by glucosamination. GAH has been shown to have a variety of biological functions, including anti-inflammatory, antioxidant, and anti-tumor activities [2][3][4]. Our previous work has demonstrated that Agaricus bisporus-derived GAH regulates the bone morphogenetic protein (BMP) signaling pathway to repair skeletal damage in zebrafish [5].…”