Anti-hyperglycaemic effects of the Japanese red maple <i>Acer pycnanthum</i> and its constituents the ginnalins B and C

Honma, Atsushi; Koyama, Tomoyuki; Yazawa, Kazunaga

doi:10.3109/14756366.2010.486795

Cited by 23 publications

(17 citation statements)

References 34 publications

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“…The GCGs did not scavenge RCS bur showed an antioxidant mechanism of inhibitory effect which was supported by the free radical scavenging (DPPH assay) and EPR data as well as metal chelating activity (Ferrous II 2,2′-bipyridyl assay). Therefore, the findings from the current study, as well as previously published animal data, 30–32 support further investigations of these natural products for their antidiabetic potential given their antioxidant, α -glucosidase inhibitory, and antiglycating properties.…”

Section: Discussionsupporting

confidence: 88%

Glucitol-core containing gallotannins inhibit the formation of advanced glycation end-products mediated by their antioxidant potential

Liu

Frost

et al. 2016

Food Funct.

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Glucitol-core containing gallotannins (GCGs) are polyphenols containing galloyl groups attached to a 1,5-anhydro-D-glucitol core, which is uncommon among naturally occurring plant gallotannins. GCGs have only been isolated from maple (Acer) species, including the red maple (Acer rubrum), a medicinal plant which along with the sugar maple (Acer saccharum), are the major sources of the natural sweetener, maple syrup. GCGs are reported to show antioxidant, α-glucosidase inhibitory, and antidiabetic effects, but their antiglycating potential is unknown. Herein, the inhibitory effects of five GCGs (containing 1–4 galloyls) on the formation of advanced glycation end-products (AGEs) were evaluated by MALD-TOF mass spectroscopy, and the BSA-fructose, and G.K. peptide-ribose assays. The GCGs showed superior activities compared to the synthetic antiglycating agent, aminoguanidine (IC50 15.8–151.3 vs. > 300 μM) at the early, middle, and late stages of glycation. Circular dichroism data revealed that the GCGs were able to protect the secondary structure of BSA protein from glycation. The GCGs did not inhibit AGEs formation by the trapping of reactive carbonyl species, namely, methylglyoxal, but showed free radical scavenging activities in the DPPH assay. The free radical quenching properties of the GCGs was further confirmed by electron paramagnetic resonance spectroscopy using ginnalin A (contains 2 galloyls) as a representative GCG. In addition, this GCG chelated ferrous iron, an oxidative catalyst of AGEs formation, supporting a potential antioxidant mechanism of antiglycating activity for these polyphenols. Therefore, GCGs should be further investigated for their antidiabetic potential given their antioxidant, α-glucosidase inhibitory, and antiglycating properties.

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Section: Discussionsupporting

confidence: 88%

Glucitol-core containing gallotannins inhibit the formation of advanced glycation end-products mediated by their antioxidant potential

Liu

Frost

et al. 2016

Food Funct.

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“…3, Table 2). Previously, it was shown that ginnalins A, B, and C have α-glucosidase inhibitory activity (18,19). However, our observations indicate that a group of unknown phenolic compounds that were present only in SML and eluted between 18-23 min, could have a more pronounced effect on α-glucosidase inhibition.…”

Section: Resultscontrasting

confidence: 75%

“…Recently, Honma et al (18) reported that sugar maple (Acer saccharum) leaf extracts had phenolic-mediated potential for type 2 diabetes management via inhibition of the carbohydrate hydrolyzing enzyme α-glucosidase and identified acertanin (ginnalin A) as the active compound. On the other hand, Japanese red maple (Acer pycnanthum K. Koch) appeared to have similar effect against type 2 diabetes, but the active compounds for the observed effect were identified as ginnalins B and C (19).…”

Section: Introductionmentioning

confidence: 95%

Seasonal influence on phenolic-mediated antihyperglycemic properties of Canadian sugar and red maple leaves using in vitro assay models

Apostolidis

Kang³

et al. 2012

Food Sci Biotechnol

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Red and sugar maple leaves collected in the summer and fall from Canada, were evaluated for phenolic content, antioxidant, α-glucosidase, and α-amylase inhibitory activities variation. The phenolic contents of summer red maple leaves (RML-S) and summer sugar maple leaves (SML-S) were higher than red and sugar maple leaves collected in fall (RML-F and SML-F, respectively). HPLC analyses showed differences in phenolic compounds present in the SML samples compared to the RML samples. The extracts were assayed for yeast and rat α-glucosidase inhibitory activities. Both results showed that SML-S extracts had the highest inhibitory activity which could possibly be attributed to the unique phenolics present therein. Milder effects were observed in terms of α-amylase inhibitory activity, with RML-F having the highest inhibitory activity. These results suggest that maple tree leaf extracts may have potential for phenolic-mediated α-glucosidase inhibition, relevant to type 2 diabetes management, with SML-S extract having the highest bioactivity.

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“…The reaction was terminated by heating with boiling water for 5 min, and the quantity of glucose produced was measured with a commercial GOD-POD kit (Glucose CII-test, WAKO Pure Chem, Osaka, Japan). 7) DPPH Free Radical Scavenging Activity In a 96-well micro plate, a 10 mM of test sample was dissolved in EtOH (1, 10, 100 mM) and 190 ml of a mixed solution, and a 3 : 1 : 4 solution of MilliQ: 400 mM MES buffer: 0.4 mM DPPH solution dissolved in EtOH were added. The reaction solution was measured at a wavelength 490 nm using a spectrophotometer.…”

Section: Methodsmentioning

confidence: 99%

“…7) In this a-glucosidase inhibitory activity, we investigated the structure-activity relationship of pycnalin (1), as well as ginnalins A (2), B (3), and C (4), and 3,6-di-GAG (5). Compounds 1-5 were found to be inhibitors of a-glucosidase, showing promising inhibitory activities in a dose-dependent manner.…”

mentioning

confidence: 99%

Pycnalin, a New .ALPHA.-Glucosidase Inhibitor from Acer pycnanthum

Ogawa

Miyamae

Honma

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Postprandial hyperglycemic excursion has been implicated as an independent risk factor for cardiovascular disease, not only among diabetes patients, but also among other pre-diabetic subjects in the general population with pre-diabetic states. 1,2) Therefore, sustained postprandial hyperglycemia (PPHG) also results in postprandial oxidative stress (PPOS). PPOS is characterized by an increased susceptibility of the organism toward oxidative damage after consumption of a meal rich in lipids and/or carbohydrates, and is associated with a higher risk for atheroscleroses, diabetes and obesity. 3) Hence, combinations of agents that reduce PPHG and PPOS are becoming therapeutics of interest to combat diabetes and its related complications. a-Glucosidase inhibitors are used in the management of non-insulin-dependent diabetes mellitus, acting by reversible inhibition of the gastrointestinal sucrases, glucoamylase, dextrinase, maltase, and isomaltase. These enzymes normally catalyze the conversion of dietary starch and sucrose into absorbable monosaccharides; therefore, enzyme inhibition delays and reduces the peak of postprandial blood glucose. 4) In a recent study, it was reported that oral administration of the Acer extract to mice caused their blood glucose level to be lower than control at 30 min. 5,6) Additionally, it was suggested that the effect is also involved in a-glucosidase inhibitory activity, and ginnalins B (3) and C (4) from A. pycnanthum were found to be a portion of the active compounds. 7) In this study, we report the isolation and structure determination of a new compound, pycnalin (1), and investigated of its a-glucosidase inhibitory and 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activities. Results and DiscussionIsolation and Structure Elucidation The leaves of A. pycnanthum were extracted with hot water. The hot water extract was partitioned among EtOAc, BuOH, and H 2 O and ginnalin A (2, 4.4%) was obtained from the EtOAc-insoluble portion. The BuOH-soluble portion was separated by octadecylsilyl ( The molecular formula of pycnalin (1), C 13 H 16 O 9 , was established by high resolution-electrospray ionization-mass spectra (HR-ESI-MS) [m/z 339.0949 (MϩNa) ϩ , Dϩ0.7 mmu]. IR spectrum implied the presence of hydroxyl (3423 cm Ϫ1 ) and ester carbonyl (1699, 1237 cm Ϫ1 ) groups. The gross structure of 1 was deduced from detailed analyses of the 1 H-and 13 C-NMR data (Table 1) aided by 2D-NMR ( 1 H-1 H correlation spectroscopy (COSY), 1 H-detected heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond connectivity (HMBC)). The 1 H-NMR spectral data showed nine proton signals. A singlet at d H 7.13, integrating for two protons, was attributed to the two aromatic protons of a galloyl group. Eight proton signals at d H 3.40-4.52 suggested the presence of a structure similar to that of a sugar moiety. The 13 C-NMR and distortionless enhancement by polarization transfer (DEPT) spectra of 1 indicated the presence of two oxymethylene carbons, four oxymethine carbons,...

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Anti-hyperglycaemic effects of the Japanese red maple Acer pycnanthum and its constituents the ginnalins B and C

Cited by 23 publications

References 34 publications

Glucitol-core containing gallotannins inhibit the formation of advanced glycation end-products mediated by their antioxidant potential

Glucitol-core containing gallotannins inhibit the formation of advanced glycation end-products mediated by their antioxidant potential

Seasonal influence on phenolic-mediated antihyperglycemic properties of Canadian sugar and red maple leaves using in vitro assay models

Pycnalin, a New .ALPHA.-Glucosidase Inhibitor from Acer pycnanthum

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