Inhibitory Activity of Cyanidin-3-rutinoside on α-Glucosidase

Adisakwattana, Sirichai; Ngamrojanavanich, Nattaya; Kalampakorn, Kanyarat; Tiravanit, Wilaiwon; Roengsumran, Sophon; Yibchok-anun, Sirintorn

doi:10.1080/14756360409162443

Cited by 47 publications

(27 citation statements)

References 21 publications

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“…26 TSAHC was originally found to inhibit ␣-glucosidase (median inhibitory concentration [IC 50 ] ϭ 0.98 M) 18 more strongly than sugar-derived glucosidase inhibitors currently used for therapeutic purposes, such as voglibose (IC 50 ϭ 23.4 M) and deoxynojirimycin (IC 50 ϭ 3.5 M). 27,28 Glycosidases are elevated in the interstitial fluid of tumors and sera of tumor patients and correlate with increased metastatic potential. Thus, there was considerable interest in the development of glycosidase inhibitors.…”

Section: Discussionmentioning

confidence: 99%

Blockade of four-transmembrane L6 family member 5 (TM4SF5)-mediated tumorigenicity in hepatocytes by a synthetic chalcone derivative

et al. 2008

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We previously reported that the four-transmembrane L6 family member 5 (TM4SF5) was highly expressed in hepatocarcinoma, induced morphological elongation and epithelialmesenchymal transition, and caused abnormal cell growth in multilayers in vitro and tumor formation in vivo. In this study, we identified a synthetic compound, 4 -(p-toluenesulfonylamido)-4-hydroxychalcone (TSAHC) that antagonized both the TM4SF5-mediated multilayer growth and TM4SF5-enhanced migration/invasion. TSAHC treatment induced multilayer-growing cells to grow in monolayers, recovering contact inhibition without accompanying apoptosis, and inhibited chemotactic migration and invasion. E pithelial monolayer integrity is maintained by integrin-mediated cell adhesion between the cell and the extracellular matrix (ECM) and by E-cadherin-mediated contact between adjacent cells. 1 Epithelial-mesenchymal transition (EMT) through loss of cellcell contacts disrupts monolayer integrity and alters cell-ECM interactions. 2 Tumor cells disseminated from primary tumors via loss of cell adhesion and contact can migrate to and invade distal tissues. 3 We recently reported that TM4SF5-mediated EMT results in a loss of contact inhibition and multilayer growth. 4 Therefore, altered cell adhesion and contact may lead to both a loss of contact inhibition and a dissemination of metastatic cells from the primary tumor. 5 Integrin-mediated cell adhesion reorganizes actin filaments 6 through activation of diverse intracellular signaling molecules, including focal adhesion kinase (FAK), Rho guanosine triphosphatases (RhoA, Rac1, and CDC42), and others, 7 which are critical for cellular morphology and migration. 8 TM4SF proteins (i.e., tetraspanins or tetraspans) are a group of membrane proteins with four transmembrane

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Section: Discussionmentioning

confidence: 99%

Blockade of four-transmembrane L6 family member 5 (TM4SF5)-mediated tumorigenicity in hepatocytes by a synthetic chalcone derivative

et al. 2008

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“…Ingestion of berry anthocyanins may have rapid effects on blood glucose levels by delaying carbohydrate digestion and inhibiting the rate of glucose absorption across the intestine [7], [8], [9], [10], [11], [12], [13], although proanthocyanidins are likely to be responsible for inhibition of α-amylase [13]. Randomized controlled trials suggest that consuming whole berries may help control blood glucose concentrations [14], [15], [16], [17], [18], but the active component is not yet clear.…”

Section: Introductionmentioning

confidence: 99%

Drinks containing anthocyanin-rich blackcurrant extract decrease postprandial blood glucose, insulin and incretin concentrations

Castro-Acosta

Smith

Miller

et al. 2016

The Journal of Nutritional Biochemistry

114

108

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Blackcurrants are rich in polyphenolic glycosides called anthocyanins, which may inhibit postprandial glycemia. The aim was to determine the dose-dependent effects of blackcurrant extract on postprandial glycemia. Men and postmenopausal women (14 M, 9 W, mean age 46 years, S.D.=14) were enrolled into a randomized, double-blind, crossover trial. Low sugar fruit drinks containing blackcurrant extract providing 150-mg (L-BE), 300-mg (M-BE) and 600-mg (H-BE) total anthocyanins or no blackcurrant extract (CON) were administered immediately before a high-carbohydrate meal. Plasma glucose, insulin and incretins (GIP and GLP-1) were measured 0–120 min, and plasma 8-isoprostane F2α, together with arterial stiffness by digital volume pulse (DVP) was measured at 0 and 120 min. Early plasma glucose response was significantly reduced following H-BE (n=22), relative to CON, with a mean difference (95% CI) in area over baseline (AOB) 0-30 min of −0.34 mmol/l.h (−0.56, −0.11, P<.005); there were no differences between the intermediate doses and placebo. Plasma insulin concentrations (AOB 0–30 min) were similarly reduced. Plasma GIP concentrations (AOB 0–120 min) were significantly reduced following H-BE, with a mean difference of −46.6 ng/l.h (−66.7, −26.5, P<.0001) compared to CON. Plasma GLP-1 concentrations were reduced following H-BE at 90 min. There were no effects on 8-isoprostane F2α or vascular function. Consumption of blackcurrant extract in amounts roughly equivalent to 100-g blackcurrants reduced postprandial glycemia, insulinemia and incretin secretion, which suggests that inclusion of blackcurrant polyphenols in foods may provide cardio-metabolic health benefits. This trial was registered at clinicaltrials.gov as NCT01706653.

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“…The combination of acarbose and cyanidin-3-galactoside has a synergistic effect on intestinal α-glucosidase inhibition [8]. Our previous study indicates that cyanidin-3-rutinoside also exhibits an inhibitory effect on yeast α-glucosidase in a non-competitive manner [9]. Although the α-glucosidase inhibitory activities of cyanidins are well-documented, studies regarding the structureactivity relationship of cyanidin and its glycosides on the inhibition of α-glucosidases and pancreatic α-amylase have not been undertaken.…”

Section: Introductionmentioning

confidence: 99%

Inhibitory Activities of Cyanidin and Its Glycosides and Synergistic Effect with Acarbose against Intestinal α-Glucosidase and Pancreatic α-Amylase

Akkarachiyasit

Charoenlertkul

Yibchok-anun

et al. 2010

IJMS

Self Cite

224

145

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Cyanidin and its glycosides are naturally dietary pigments which have been indicated as promising candidates to have potential benefits to humans, especially in the prevention and treatment of diabetes mellitus. We investigated the structure activity relationships of cyanidin and its glycosides to inhibit intestinal α-glucosidases and pancreatic α-amylase in vitro. The results found that cyanidin and its glycosides are more specific inhibitors of intestinal sucrase than intestinal maltase. Cyanidin-3-galactoside and cyanidin-3-glucoside were the most potent inhibitors against intestinal sucrase and pancreatic α-amylase with IC50 values of 0.50 ± 0.05 and 0.30 ± 0.01 mM, respectively. Our findings indicate that the structural difference between glucose and galactose at the 3-O-position of cyanidin was an important factor for modulating the inhibition of intestinal sucrase and pancreatic α-amylase. The combination of cyandin-3-glucoside, cyanidin-3- galactoside or cyanidin-3,5-diglucosides with a low concentration of acarbose showed synergistic inhibition on intestinal maltase and sucrase. The synergistic inhibition was also found for a combination of cyanidin or cyanidin-3-glucoside with a low concentration of acarbose. The findings could provide a new insight into a use for the naturally occurring intestinal α-glucosidase and pancreatic α-amylase inhibitors for the prevention and treatment of diabetes and its complications.

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Inhibitory Activity of Cyanidin-3-rutinoside on α-Glucosidase

Cited by 47 publications

References 21 publications

Blockade of four-transmembrane L6 family member 5 (TM4SF5)-mediated tumorigenicity in hepatocytes by a synthetic chalcone derivative

Blockade of four-transmembrane L6 family member 5 (TM4SF5)-mediated tumorigenicity in hepatocytes by a synthetic chalcone derivative

Drinks containing anthocyanin-rich blackcurrant extract decrease postprandial blood glucose, insulin and incretin concentrations

Inhibitory Activities of Cyanidin and Its Glycosides and Synergistic Effect with Acarbose against Intestinal α-Glucosidase and Pancreatic α-Amylase

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