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Food Science and Human Wellness 2016, 5(2): 85-94 https://doi.org/10.1016/j.fshw.2016.02.004
Research Article | Open Access | Issue | Published: 05 March 2016

Bioactive constituents from the leaves of Quercus phillyraeoides A. Gray for α-glucosidase inhibitor activity with concurrent antioxidant activity

Show Author's Information Anastasia Wheni Indrianingsiha,b,  Sanro Tachibanac( )
The United Graduate School of Agricultural Sciences, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan
Research Unit for Development of Chemical Engineering Process, Indonesian Institute of Sciences, Gading, Playen, Gunungkidul, Yogyakarta 55581, Indonesia
Department of Applied Biosciences, Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan

Peer review under responsibility of Beijing Academy of Food Sciences.

Keywords:
Antioxidative activity, Quercus phillyraeoides A. Gray, α-Glucosidase inhibitor, Lineweaver–Burk plot
Cite this article:
Indrianingsih AW, Tachibana S. Bioactive constituents from the leaves of Quercus phillyraeoides A. Gray for α-glucosidase inhibitor activity with concurrent antioxidant activity. Food Science and Human Wellness, 2016, 5(2): 85-94. https://doi.org/10.1016/j.fshw.2016.02.004
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Abstract Full text About this article

Several α-glucosidase inhibitory constituents were isolated from the methanolic extract of the leaves of Quercus phillyraeoides A. Gray (Q. phillyraeoides) using a bioassay-guided fractionation technique. Further separation and purification of the methanol-soluble fraction led to the isolation of constituents with moderate and strong inhibitory activities against α-glucosidase: β-sitosterol-D-glucoside (1) and condensed tannin fractions (2, 3, 4, 5, and 6). Compound 1 and fractions 2–6 had inhibitory concentration (IC50) values against α-glucosidase from Saccharomyces cerevisiae of 118.8, 2.79, 2.78, 3.10, 2.60, and 3.14 μg/mL, respectively, while quercetin as the standard had an IC50 value of 4.80 μg/mL. Furthermore, the significant antioxidant activities were evaluated using several assays, such as the DPPH radical scavenging, hydrogen peroxide radical scavenging, reducing power, and β-carotene-linoleate bleaching assays, and the results suggested that the isolated constituents showed their possible application for treating the hyperglycemia-induced oxidative stress. The results of the present study showed the potential of Q. phillyraeoides as a rich source of natural antidiabetic medicine.


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About this article

Bioactive constituents from the leaves of Quercus phillyraeoides A. Gray for α-glucosidase inhibitor activity with concurrent antioxidant activity

Show Author's information Anastasia Wheni Indrianingsiha,b, Sanro Tachibanac( )
The United Graduate School of Agricultural Sciences, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan
Research Unit for Development of Chemical Engineering Process, Indonesian Institute of Sciences, Gading, Playen, Gunungkidul, Yogyakarta 55581, Indonesia
Department of Applied Biosciences, Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan

Peer review under responsibility of Beijing Academy of Food Sciences.

Abstract

Several α-glucosidase inhibitory constituents were isolated from the methanolic extract of the leaves of Quercus phillyraeoides A. Gray (Q. phillyraeoides) using a bioassay-guided fractionation technique. Further separation and purification of the methanol-soluble fraction led to the isolation of constituents with moderate and strong inhibitory activities against α-glucosidase: β-sitosterol-D-glucoside (1) and condensed tannin fractions (2, 3, 4, 5, and 6). Compound 1 and fractions 2–6 had inhibitory concentration (IC50) values against α-glucosidase from Saccharomyces cerevisiae of 118.8, 2.79, 2.78, 3.10, 2.60, and 3.14 μg/mL, respectively, while quercetin as the standard had an IC50 value of 4.80 μg/mL. Furthermore, the significant antioxidant activities were evaluated using several assays, such as the DPPH radical scavenging, hydrogen peroxide radical scavenging, reducing power, and β-carotene-linoleate bleaching assays, and the results suggested that the isolated constituents showed their possible application for treating the hyperglycemia-induced oxidative stress. The results of the present study showed the potential of Q. phillyraeoides as a rich source of natural antidiabetic medicine.

Keywords: Antioxidative activity, Quercus phillyraeoides A. Gray, α-Glucosidase inhibitor, Lineweaver–Burk plot

References(42)

[1]

R.P. Lanza, D.M. Ecker, W.M. Kuhtreiber, J.P. Marsh, J. Ringeling, W.L. Chick, Transplantation of islets using microencapsulation: studies in diabetic rodents and dogs, J. Mol. Med. 77 (1999) 206-210.
DOI Google Scholar
[2]

A.L. Notkins, Immunologic and genetic factors in type 1 diabetes, J. Biol. Chem. 277 (2002) 43545-43548.
DOI Google Scholar
[3]

S.O. Oyedemi, G. Bradley, A.J. Afolayan, Ethnobotanical survey of medicinal plants used for the management of diabetes mellitus in the Nkonkobe municipality of South Africa, J. Med. Plant. Res. 3 (2009) 1040-1044.
Google Scholar
[4]

B. Mlinar, J. Marc, A. Janez, M. Pfeifer, Molecular mechanisms of insulin resistance and associated diseases, Clin. Chim. Acta 375 (2007) 20-35.
DOI Google Scholar
[5]

I. Funke, M.F. Melzig, Traditionally used plants in diabetes therapy – phytotherapeutics as inhibitors of α-amylase activity, Braz. J. Pharmacogn. 16 (2006) 1-5.
DOI Google Scholar
[6]

B.B. Zhang, D.E. Moller, New approaches in the treatment of type 2 diabetes, Curr. Opin. Chem. Biol. 4 (2000) 461-467.
DOI Google Scholar
[7]

F.J. Alarcon-Aguilar, R. Roman-Ramos, J.L. Flores-Saenz, F. Aguirre-Garcia, Investigation on the hypoglycaemic effects of extracts of four Mexican medicinal plants in normal and alloxan-diabetic mice, Phytother. Res. 16 (2002) 383-386.
DOI Google Scholar
[8]

M.J. Aybar, A.N. Sanchez Riera, A. Grau, S.S. Sanchez, Hypoglycemic effect of the water extract of Smallantus sonchifolius (yacon) leaves in normal and diabetic rats, J. Ethnopharmacol. 74 (2001) 125-132.
DOI Google Scholar
[9]

W.R. Cunha, G.M. Arantes, D.S. Ferreira, R. Lucarini, M.L.A. Silva, N.A.J.C. Furtado, et al., Hypoglycemic effect of Leandra lacunosa in normal and alloxan-induced diabetic rats, Fitoterapia 79 (2008) 356-360.
DOI Google Scholar
[10]

C. Coman, O.D. Rugina, C. Socaciu, Plants and natural compounds with antidiabetic action, Not. Bot. Horti. Agrobot. 40 (2012) 314-325.
DOI Google Scholar
[11]

S. Prasad, A.K. Sinha, Free radical activity in hypertensive type 2 diabetic patients, Int. J. Diabetes Mellit. 2 (2010) 141-143.
DOI Google Scholar
[12]

H.E. Poulson, H. Prieme, S. Loft, Role of oxidative DNA damage in cancer initiation and promotion, Eur. J. Cancer Prev. 7 (1998) 9-16.
Google Scholar
[13]

J.I. Kim, H.Y. Kim, S.G. Kim, K.T. Lee, I.H. Ham, W.K. Whang, Antioxidant compounds from Quercus salicina Blume stem, Arch. Pharm. Res. 31 (2008) 274-278.
DOI Google Scholar
[14]

G. Nonaka, S. Nakayama, I. Nishioka, Tannins and related compounds LXXXIII. Isolation and structure of hydrolyzable tannins, phillyraeoidins A-E from Quercus phillyraeoides, Chem. Pharm. Bull. 37 (1989) 2030-2036.
DOI Google Scholar
[15]

B. Labarbe, V. Cheynier, F. Brossaud, J.M. Souquet, M. Moutounet, Quantitative fractionation of grape proanthocyanidins according to their degree of polymerization, J. Agric. Food Chem. 47 (1999) 2719-2723.
DOI Google Scholar
[16]

Y.M. Kim, Y.K. Jeong, M.H. Wang, W.Y. Lee, H.I. Rhee, Inhibitory effect of pine extract on α-glucosidase activity and postprandial hyperglycemia, Nutrition 21 (2005) 756-761.
DOI Google Scholar
[17]

G.C. Yen, H.Y. Chen, Antioxidant activity of various tea extracts in relation to their antimutagenicity, J. Agric. Food Chem. 43 (1995) 27-32.
DOI Google Scholar
[18]

J. Wang, X. Yuan, Z. Jin, Y. Tian, H. Song, Free radical and reactive oxygen species scavenging activities of peanut skins extract, Food Chem. 104 (2007) 242-250.
DOI Google Scholar
[19]

M. Oyaizu, Studies on products of browning reaction – antioxidative activities of products of browning reaction prepared from glucosamine, Jpn. J. Nutr. 44 (1986) 307-315.
DOI Google Scholar
[20]

G.K. Jayaprakasha, R.P. Singh, K.K. Sakariah, Antioxidant activity of grape seed (Vitis vinifera) extracts on peroxidation models in vitro, Food Chem. 73 (2001) 285-290.
DOI Google Scholar
[21]

M. Miyazawa, N. Yagi, K. Taguchi, Inhibitory compounds of α-glucosidase activity from Arctium lappa L, J. Oleo. Sci. 54 (2005) 589-594.
DOI Google Scholar
[22]

S. Sang, H. Kikuzaki, K. Lapsley, R.T. Rosen, N. Nakatani, C.T. Ho, Sphingolipid and other constituents from almond nuts (Prunus amygdalus Batsch), J. Agric. Food Chem. 50 (2002) 4709-4712.
DOI Google Scholar
[23]

P. Schofield, D.M. Mbugua, A.N. Pell, Analysis of condensed tannins: a review, Anim. Feed Sci. Tech. 91 (2001) 21-40.
DOI Google Scholar
[24]

S. Matthews, I. Mila, A. Scalbert, B. Pollet, C. Lapierre, C.L.M. Herve du Penhoat, et al., Method for estimation of proanthocyanidins based on their acid depolymerization in the presence of nucleophiles, J. Agric. Food Chem. 45 (1997) 1195-1201.
DOI Google Scholar
[25]

H. Sugihara, M. Nagao, T. Harada, Y. Nakajima, K. Tanimura-Inagaki, F. Okajima, et al., Comparison of three α-glucosidase inhibitors for glycemic control and bodyweight reduction in Japanese patients with obese type 2 diabetes, J. Diabetes Investig. 5 (2014) 206-212.
DOI Google Scholar
[26]

V. Katalinic, S.S. Mozina, D. Skroza, I. Generalic, H. Abramovic, M. Milos, et al., Polyphenolic profile, antioxidant properties and antimicrobial activity of grape skin extracts of 14 Vitis vinifera varieties grown in Dalmatia (Cratioa), Food Chem. 119 (2010) 715-723.
DOI Google Scholar
[27]

Y.Q. Li, F.C. Zhou, F. Gao, J.S. Bian, F. Shan, Comparative evaluation of quercetin, isoquercetin, and rutin as inhibitors of alpha-glucosidase, J. Agric. Food Chem. 57 (2009) 11463-11468.
DOI Google Scholar
[28]

H. Gao, T. Nishioka, J. Kawabata, T. Kasai, Structure-activity relationships for alpha-glucosidase inhibition of baicalein 5,6,7- trihydroxyflavone: the effect of A-ring substitution, Biosci. Biotechnol. Biochem. 68 (2004) 369-375.
DOI Google Scholar
[29]

M.D. Ivorra, M.P. D’Ocon, M. Paya, A. Villar, Antihyperglycemic and insulin-releasing effects of beta-sitosterol 3-beta-D-glucoside and its aglycone, beta sitosterol, Arch. Int. Pharmacodyn. Ther. 296 (1988) 224-231.
Google Scholar
[30]

C.N. Kunyanga, J.K. Imungi, M. Okoth, C. Momanyi, H.K. Biesalski, V. Vadivel, Antioxidant and antidiabetic properties of condensed tannins in acetonic extract of selected raw and processed indigenous food ingredients from Kenya, J. Food Sci. 76 (2011) C560-C567.
DOI Google Scholar
[31]

R.A. Anderson, M.M. Polansky, Tea enhances insulin activity, J. Agric. Food Chem. 50 (2002) 7182-7186.
DOI Google Scholar
[32]

T. Matsui, T. Ueda, T. Oki, K. Sugita, N. Terahara, K. Matsumoto, α-Glucosidase inhibitory action of natural acylated anthocyanidins. 1. Survey of natural pigments with potent inhibitory activity, J. Agric. Food Chem. 49 (2001) 1948-1951.
DOI Google Scholar
[33]

M.F. Mahomoodally, D.D. Muthoora, Kinetic of inhibition of carbohydrate-hydrolysing enzymes, antioxidant activity and polyphenolic content of Phyllanthus amarus Schum. & Thonn. (Phyllanthaceae), J. Herb. Med. 4 (2014) 208-223.
DOI Google Scholar
[34]

S.B. Kedare, R.P. Singh, Genesis and development of DPPH method of antioxidant assay, J. Food Sci. Technol. 48 (2011) 412-422.
DOI Google Scholar
[35]

H.Y. Lai, Y.Y. Lim, Evaluation of antioxidant activities of the methanolic extracts of selected ferns in Malaysia, Int. J. Environ. Sci. Dev. 2 (2011) 442-447.
DOI Google Scholar
[36]

M.A. Gyamfi, Y. Aniya, Antioxidant properties of Thonningianin A, isolated from the African medicinal herb, Thonningia sanguine, Biochem. Pharmacol. 63 (2002) 1725-1737.
DOI Google Scholar
[37]

J. Serrano, R. Puupponen-Pimia, A. Dauer, A. Aura, F. Saura-Calixto, Tannins: current knowledge of food sources, intake, bioavailability and biological effects, Mol. Nutr. Food Res. 53 (2009) S310-S329.
DOI Google Scholar
[38]

R. Amarowicz, M. Naczk, F. Shahidi, Antioxidant activity of crude tannins of canola and rapeseed hulls, J. Am. Oil. Chem. Soc. 77 (2000) 957-961.
DOI Google Scholar
[39]

P. Siddhuraju, P.S. Mohan, K. Becker, Studies on the antioxidant activity of Indian Laburnum (Cassia fistula L.): a preliminary assessment of crude extracts from stem bark, leaves, flowers and fruit pulp, Food Chem. 79 (2002) 61-67.
DOI Google Scholar
[40]

P. Siddhuraju, K. Becker, The antioxidant and free radical scavenging activities of processed cowpea (Vigna unguiculata (L.) Walp.) seed extracts, Food Chem. 101 (2007) 10-19.
DOI Google Scholar
[41]

R.S. Kumar, B. Rajkapoor, P. Perumal, Antioxidant activities of Indigofera cassioides Rottl. Ex. DC using various in vitro assay models, Asian Pac. J. Trop. Biomed. 2 (2012) 256-261.
DOI Google Scholar
[42]

T. Madhujith, M. Naczk, F. Shahidi, Antioxidant activity of common beans (Phaseolus vulgaris L.), J. Food Lip. 11 (2004) 220-233.
DOI Google Scholar
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Received: 06 October 2015
Revised: 18 February 2016
Accepted: 28 February 2016
Published: 05 March 2016
Issue date: June 2016

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© 2016 Beijing Academy of Food Sciences.

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