13
views
0
recommends
+1 Recommend
0 collections
    0
    shares
      • Record: found
      • Abstract: found
      • Article: found
      Is Open Access

      Effect of antioxidant activity of caffeic acid with cyclodextrins using ground mixture method

      research-article

      Read this article at

      Bookmark
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Graphical Abstract

          Caffeic acid/α-cyclodextrin (molar ratio = 1/1), the vinylene group of the caffeic acid molecule appears to be included from the wider to the narrower rim of the ring of α-cyclodextrin. Caffeic acid /β-cyclodextrin (molar ratio = 1/1), the aromatic ring of the caffeic acid molecule appears to be included from the wider to the narrower rim of the ring of βCD. This suggests that forms of inclusion differed in the caffeic acid /α-cyclodextrin (molar ratio = 1/1) and the caffeic acid /β-cyclodextrin (molar ratio = 1/1).

          Abstract

          In the current study, we prepared a ground mixture (GM) of caffeic acid (CA) with α-cyclodextrin (αCD) and with β-cyclodextrin (βCD), and then comparatively assessed the physicochemical properties and antioxidant capacities of these GMs. Phase solubility diagrams indicated that both CA/αCD and CA/βCD formed a complex at a molar ratio of 1/1. In addition, stability constants suggested that CA was more stable inside the cavity of αCD than inside the cavity of βCD. Results of powder X-ray diffraction (PXRD) indicated that the characteristic diffraction peaks of CA and CD disappeared and a halo pattern was produced by the GMs of CA/αCD and CA/βCD (molar ratios = 1/1). Dissolution testing revealed that both GMs had a higher rate of dissolution than CA alone did. Based on the 1H- 1H NOESY NMR spectra for the GM of CA/αCD, the vinylene group of the CA molecule appeared to be included from the wider to the narrower rim of the αCD ring. Based on spectra for the GM of CA/βCD, the aromatic ring of the CA molecule appeared to be included from the wider to the narrower rim of the βCD ring. This suggests that the structures of the CA inclusion complexes differed between those involving αCD rings and those involving βCD rings. Results of a DPPH radical-scavenging activity test indicated that the GM of CA/αCD had a higher antioxidant capacity than that of the GM of CA/βCD. The differences in the antioxidant capacities of the GMs of CA/αCD and CA/βCD are presumably due to differences in stability constants and structures of the inclusion complexes.

          Related collections

          Most cited references28

          • Record: found
          • Abstract: found
          • Article: not found

          Antihyperglycemic and antioxidant properties of caffeic acid in db/db mice.

          This study investigated the blood glucose-lowering effect and antioxidant capacity of caffeic acid in C57BL/KsJ-db/db mice. Caffeic acid induced a significant reduction of the blood glucose and glycosylated hemoglobin levels than the control group. The plasma insulin, C-peptide, and leptin levels in caffeic acid group were significantly higher than those of the control group, whereas the plasma glucagon level was lower. Increased plasma insulin by caffeic acid was attributable to an antidegenerative effect on the islets. Caffeic acid also markedly increased glucokinase activity and its mRNA expression and glycogen content and simultaneously lowered glucose-6-phosphatase and phosphoenolpyruvate carboxykinase activities and their respective mRNA expressions, accompanied by a reduction in the glucose transporter 2 expression in the liver. In contrast to the hepatic glucose transporter 2, adipocyte glucose transporter 4 expression was greater than the control group. In addition, caffeic acid significantly increased superoxide dismutase, catalase, and glutathione peroxidase activities and their respective mRNA levels, while lowering the hydrogen peroxide and thiobarbituric acid reactive substances levels in the erythrocyte and liver of db/db mice. These results indicate that caffeic acid exhibits a significant potential as an antidiabetic agent by suppressing a progression of type 2 diabetic states that is suggested by an attenuation of hepatic glucose output and enhancement of adipocyte glucose uptake, insulin secretion, and antioxidant capacity.
            Bookmark
            • Record: found
            • Abstract: found
            • Article: not found

            Chlorogenic acid and synthetic chlorogenic acid derivatives: novel inhibitors of hepatic glucose-6-phosphate translocase.

            The enzyme system glucose-6-phosphatase (EC 3.1.3.9) plays a major role in the homeostatic regulation of blood glucose. It is responsible for the formation of endogenous glucose originating from gluconeogenesis and glycogenolysis. Recently, chlorogenic acid was identified as a specific inhibitor of the glucose-6-phosphate translocase component (Gl-6-P translocase) of this enzyme system in microsomes of rat liver. Glucose 6-phosphate hydrolysis was determined in the presence of chlorogenic acid or of new synthesized derivatives in intact rat liver microsomes in order to assess the inhibitory potency of the compounds on the translocase component. Variation in the 3-position of chlorogenic acid had only poor effects on inhibitory potency. Introduction of lipophilic side chain in the 1-position led to 100-fold more potent inhibitors. Functional assays on isolated perfused rat liver with compound 29i, a representative of the more potent derivatives, showed a dose-dependent inhibition of gluconeogenesis and glycogenolyosis, suggesting glucose-6-phosphatase as the locus of interference of the compound for inhibition of hepatic glucose production also in the isolated organ model. Gl-6-P translocase inhibitors may be useful for the reduction of inappropriately high rates of hepatic glucose output often found in non-insulin-dependent diabetes.
              Bookmark
              • Record: found
              • Abstract: found
              • Article: not found

              Characterization of inhibitors of postprandial hyperglycemia from the leaves of Nerium indicum.

              Nerium indicum is an India-Pakistan-originated shrub belonging to the oleander family. The ingestion of leaves of N. indicum before a meal is known to effect the lowering of postprandial glucose levels in Type II diabetic patients and this plant is now used as a folk remedy for Type II diabetes in some regions of Pakistan. In the present study, the hot-water extract of N. indicum leaves was found to reduce the postprandial rise in the blood glucose when maltose or sucrose was loaded in rats. It was also found that the extract strongly inhibited alpha-glucosidase, suggesting that the suppression of the postprandial rise in the blood glucose is due to the occurrence of some inhibitors of alpha-glucosidase in the leaves. We, therefore, tried to isolate the active principles from the leaf extract, using alpha-glucosidase-inhibitory activity as the index. Employing Sephadex G-15, silica gel and reversed-phase HPLC, we isolated two active compounds. The UV, mass and NMR spectrometric analyses established that the chemical structures of these compounds are 3-O-caffeoylquinic acid (chlorogenic acid) and its structural isomer, 5-O-caffeoylquinic acid. Both compounds were shown to inhibit alpha-glucosidases in a non-competitive manner. The authentic chlorogenic acid was found to suppress the postprandial rise in the blood glucose in rats and also inhibited the absorption of the glucose moiety from maltose and glucose in the everted gut sac system prepared from rat intestine. These results demonstrate that chlorogenic acid is one of the major anti-hyperglycemic principles present in the leaves of N. indicum. Furthermore, among polyphenol compounds tested, quercetin and catechins were shown to have strong inhibitory activity against alpha-glucosidase.
                Bookmark

                Author and article information

                Contributors
                Journal
                Asian J Pharm Sci
                Asian J Pharm Sci
                Asian Journal of Pharmaceutical Sciences
                Shenyang Pharmaceutical University
                1818-0876
                2221-285X
                14 October 2017
                January 2018
                14 October 2017
                : 13
                : 1
                : 24-33
                Affiliations
                Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado-shi, Saitama 3500295, Japan
                Author notes
                [* ]Corresponding author. Laboratory of Drug Safety Management, Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado-shi, Saitama 350-0295, Japan. Tel.: +81 49 271 7317; Mobile: +81 90 6921 9565. yinoue@ 123456josai.ac.jp
                Article
                S1818-0876(17)30352-5
                10.1016/j.ajps.2017.08.006
                7032159
                32104375
                2fc650aa-1823-4ece-9a66-dc9ebc977ac7
                © 2018 Shenyang Pharmaceutical University. Production and hosting by Elsevier B.V.

                This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

                History
                : 8 May 2017
                : 8 August 2017
                : 15 August 2017
                Categories
                Original Research Article

                caffeic acid,cyclodextrins,inclusion,antioxidant activity,solubility,ground mixture

                Comments

                Comment on this article