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Isolation of Antidiabetic Principle from Fruit Rinds of Punica Granatum

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Isolation of Antidiabetic Principle from Fruit Rinds of Punica Granatum Hindawi Publishing Corporation Evidence-Based Complementary and Alternative Medicine Volume 2012, Article ID 147202, 11 pages doi:10.1155/2012/147202 Research Article Isolation of Antidiabetic Principle from Fruit Rinds of Punica granatum Vishal Jain,1 G. L. Viswanatha,2 D. Manohar,1 and H. N. Shivaprasad1 1 Research and Development, Olive Lifesciences Pvt. Ltd., Karnataka, Tumkur 572 106, India 2 Department of Pharmacology, PES College of Pharmacy, Karnataka, Bangalore 560 050, India Correspondence should be addressed to Vishal Jain, [email protected] Received 26 February 2012; Accepted 26 April 2012 Academic Editor: I-Min Liu Copyright © 2012 Vishal Jain et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Present study was aimed to isolate and evaluate the antidiabetic activity of phytoconstituents from fruit rinds of Punica granatum. With the above objectives Valoneic acid dilactone (VAD) was isolated from methanolic fruit rind extracts of Punica granatum (MEPG) and confirmed by 1H-NMR, 13C-NMR, and mass spectral data. Antidiabetic activity was evaluated by Aldose reductase, α-amylase and PTP1B inhibition assays in in vitro and Alloxan-induced diabetes in rats was used as an in vivo model. In bioactivity studies, MEPG and VAD have showed potent antidiabetic activity in α-amylase, aldose reductase, and PTP1B inhibition assays with IC50 values of 1.02, 2.050, 26.25 μg/mL and 0.284, 0.788, 12.41 μg/mL, respectively. Furthermore, in alloxan-induced diabetes model MEPG (200 and 400 mg/kg, p.o.) and VAD (10, 25, and 50 mg/kg, p.o.) have showed significant and dose dependent antidiabetic activity by maintaining the blood glucose levels within the normal limits. Inline with the biochemical findings histopathology of MEPG (200 and 400 mg/kg, p.o.), VAD (10, 25, and 50 mg/kg, p.o.), and glibenclamide (10 mg/kg, p.o.) treated animals showed significant protection against alloxan-induced pancreatic tissue damage. These findings suggest that MEPG and VAD possess significant antidiabetic activity in both in vitro and in vivo models. 1. Introduction such as flavonoids, gallotannins, amino acids, and other related polyphenols [5]. Diabetes mellitus is a metabolic disorder characterized by Pomegranate (Punica granatum L., Punicaceae) is used hyperglycaemia and alterations in carbohydrate, lipid, and in the traditional system of medicine in different Asian protein metabolism, associated with absolute or relative cultures for the treatment of variety of ailments. In Ayurvedic deficiencies in insulin secretion and/or insulin action [1]. medicine, the plant is described under its Sanskrit name The World Health Organization (WHO) has estimated “dalima” (fruit) as a “blood purifier” and used to cure that major burden of diabetes will occur in developing parasitic infections, aphthae (mouth ulcers), diarrhoea, and countries, and by 2025, there will be 42% increase (from 51 ulcers [6]. Punica granatum is a deciduous tree belongs to to 72 million) in the developed countries and 170% increase the family Punicaceae; it is known for its edible fruit. During (from 84 to 228 million) in the developing countries [2]. the last two decades, various parts of the plant had been It is estimated that, by 2025, India, China, and the United subjected to extensive phytochemical, pharmacological, and States will be the top three countries to have large number of clinical investigations; many interesting findings have been diabetic patients [3]. reported in various fields [7]. The high prevalence of diabetes as well as its long- Punica granatum is found to contain hydrolysable tan- term complications has led to an ongoing search for nins as major active chemical constituents and phyto- hypoglycaemic agents; over the years, various medicinal constituents, namely, corilagin, ellagic acid, kaempferol, plants and their extracts have been reported to be effective luteolin, myricetin, quercetin, quercimetrine, and quercetin- in the treatment of diabetes [4]. Plants are rich sources 3-o-rutinoside which were previously isolated from the fruits of antidiabetic, antihyperlipidemic, and antioxidant agents of Punica granatum [8]. 2 Evidence-Based Complementary and Alternative Medicine In the literature, various parts of the plant are reported Dried fruit rind powder of pomegranate 3 kg for various pharmacological activities such as antioxidant [9], antidiarrheal [10], anti-inflammatory [11], antimalarial [12], antimutagenic [13], immunomodulatory [14], hepato- protective [15], antiulcer [16], atherosclerosis and thyroid 800 g methanolic extract dysfunction [17], memory enhancing [18], wound healing [19], and anticancer [20] activities. Apart from these medic- Partitioned with ethyl acetate inal uses, various parts of the plant have been scientifically proved for antidiabetic activity [21]. In our previous studies, Ethyl acetate fraction (137.3 g) we have isolated three components from methanolic extracts Fractionation of ethyl acetate fraction of Punica granatum [8]. In continuation, the present study was undertaken to isolate the antidiabetic principle from the methanolic extracts of fruit rinds of Punica granatum. Fr-1 Fr-(2-6) Fr-7 Fr-8 Fr-(9-12) 2. Materials and Methods 2.1. Drugs and Chemicals. Human recombinant PTP1B (BIOMOL International LP (Plymouth Meeting, PA)), α- Valoneic acid dilactone amylase (Sigma Aldrich, Bangalore), acarbose (Glenmark, Mumbai), glibenclamide (Cipla, Mumbai), and biochemical Figure 1: Scheme of isolation process. kits (ERBA diagnostic Mannheim GMBH, Germany) were used, and all the solvents used for the extraction and isolation were of analytical grade and purchased from local firms. (98% pure), respectively, based on spectral data. With this 2.2. Plant Material. The fruit rinds of Punica granatum were background information, FR-7 was further taken forward for collected locally and authenticated by Dr. K. P. Srinath, characterization by NMR and Mass spectroscopy at Radiant Department of Botany, Bangalore University, Bangalore; Research and Training Institute and IISc, Bangalore. a voucher specimen was deposited in the department (PESCP/2009-10/PG-06). 2.4. Experimental Animals. Male Wistar rats (200–250 g) were purchased from Bioneeds, Nelamangala, Tumkur, 2.3. Isolation and Identification of the Compound. Fruit rinds India, and they were maintained in polypropylene cages at ± ◦ of Punica granatum were collected, dried, and powdered; the atemperatureof25 1 C and relative humidity of 45– powder (3.0 Kg) was successively extracted with methanol in 55% in clean environment under 12:12 h light-dark cycle. a static extractor and concentrated under vacuum at 60◦C Theanimalshadfreeaccesstofoodpellets(PranavAgro and dried in vacuum tray dryer. The percentage yield of the Industries, Bangalore, India) and purified water ad libitum. methanolic extract was found to be 26.67% w/w (800 g per AlltheexperimentalprotocolswereapprovedbyInstitu- 3.0 kg of methanolic extract). tional Animal Ethics Committee (IAEC), and all the animal Vacuum-dried methanolic extract (800 g) was macerated experiments were conducted according to the principles with ethyl acetate in the solvent : solute ratio of 4 : 1 for 72 h and guidelines of CPCSEA (Committee for the Purpose of with frequent shaking. The fraction was dried using vacuum Control and Supervision of Experimentation on Animals), tray dryer. The yield of ethyl acetate fraction was found to India. be 27% w/w. The major phytochemical constituents present in the ethyl acetate fraction were identified by thin-layer 2.5. Experimental Protocol chromatography (TLC). TLC plates were developed using water : acetic acid solvent system (3 : 2) and scanned at 254 2.5.1. In Vitro α-Amylase Inhibition Assay. In vitro α-amylase and 366 nm. The 5% FeCl3 reagent was sprayed, and the inhibition assay was carried out based on the spectrophoto- chromatogram was observed. metric assay using acarbose as the reference compound [4]. The fraction was subjected to HPLC for the identifi- 2 mg of MEPG and VAD was dissolved in 500 μLofDMSO, cation and quantification of the active components; based and further dilutions were prepared using deionised water. on HPLC data, ethyl acetate fraction was subjected to The enzyme α-amylase solution (0.5 unit/mL) was prepared column chromatography for the isolation of phytochemical by mixing 3.246 mg of α-amylase (EC 3.2.1.1) in 100 mL of constituent using a glass column and Diaion resin as 40 mM phosphate buffer pH 6.9. In short, 60 μLof40mM stationary phase. Totally 12 subfractions (FR-1 to FR-12) phosphate buffer/acarbose/test drug and 30 μLofα-amylase were obtained from the ethyl acetate fraction, and all the enzyme were added, mixed, and preincubated at 37◦Cfor sub fractions were subjected to HPLC for the identification 10 min, and then 120 μL of 2-chloro-p-nitrophenyl-α-D- of the desired compound. Scheme of isolation process is maltotrioside (CNPG3) was added, mixed, and incubated at given in Figure 1. In our previous study, the FR-1 and FR- 37◦C for 8 min. The absorbance was measured at 405 nm, 8 were identified as gallic acid (95% pure) and ellagic acid and control reaction was carried out without the extract. Evidence-Based Complementary and Alternative Medicine 3 Percentage inhibition was calculated by expression: adjusted to an ionic strength of 0.15 M by the addition of NaCl. In brief, appropriately diluted inhibitors (undiluted % Inhibition and 50 μM compound) were added to the reaction mixture containing 0 or 2.5 mM pNPP (final assay concentration, Absorbance of control − Absorbance of test μ = × 100. total volume of 100 L). The reaction was initiated by the Absorbance of control addition of the enzyme (i.e., recombinant PTP1B) and (1) allowed to proceed for 5 min before the inhibitor was added and the time was recorded, that is, it continued 2.5.2. In Vitro Aldose Reductase Inhibition Assay incubation for 5–60 min at 37◦C. The reaction was stopped by the addition of 20 μL 0.5 M NaOH in 50% ethanol.
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