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Punica Granatum L.) Iranian Journal of Pharmaceutical Sciences 2021: 17 (1): 51-68 www.ijps.ir Original Article Diversity of Phenolic Profiles in Peel of an Iranian Pomegranate Cultivar (Punica granatum L.) Akram Taleghani*, Reza Akbari Department of Chemistry, Faculty of Science, Gonbad Kavous University, Gonbad, Iran. Abstract Pomegranate (Punica granatum L.) is one of the oldest known fruits native to Iran. In addition to multiple studies carried out on different parts of pomegranate, the peels are noted due to various phytochemicals in different colors and regions. In the present study, major anthocyanins and non-anthocyanins of an Iranian black pomegranate cultivar (i.e., pomegranate samples of Ghaemshahr, Iran) were analyzed using high-performance liquid chromatography-mass spectrometry. In total, 30 compounds were obtained from pomegranate peels. Among these compounds, 5 anthocyanins, 1 gallotannin, 15 ellagitannins, 4 hydroxybenzoic acids, 2 gallagyl esters, 1 dihydroflavonol, and 7 hydroxycinnamic acids were identified based on their fragmentation patterns and ultraviolet spectra. Among the varieties of Iranian pomegranates, the anthocyanins of peonidin-hexoside and cyanidin-pentoside were identified in this species for the first time. Peonidin-hexoside, caffeic acid, coumaric acid-hexoside, and galloyl-hexoside were major phenolic compounds. In addition, the antioxidant activity of different fractions was tested using DPPH free radical scavenging in vitro assay (IC50: 133.13-557.23 µg/mL). The obtained results of this study highlighted that this cultivar can be an important candidate for future new drug discoveries. Keywords: Punica granatum, peel, anthocyanin, non-anthocyanin phenolic compounds, HPLC-MS/MS, antioxidant. Corresponding Authors: Akram Taleghani, phytochemicals. It is native to the Department of Chemistry, Faculty of Science, Gonbad Mediterranean region and is cultivated in Kavous University, Gonbad, Iran. Tel: +98 9156872563 subtropical and tropical regions around the Email: [email protected] Cite this article as: Taleghani A, Akbari A, Diversity world, such as Iran, California, Turkey, Egypt, of Phenolic Profiles in Peel of an Iranian Pomegranate Italy, India, Chile, and Spain [1]. Pomegranate Cultivar (Punica granatum L.), 2021, 17 (1): 51-68. peels (PPs) remain as byproducts after juice extraction. At present, fruit peels have become 1. Introduction attractive due to beneficial phytochemicals and Pomegranate (Punica granatum L.) is are utilized in pharmaceutical, food, and consumed as a popular fruit and juice due to cosmetic industries [2, 3]. In PPs, the main the potential health benefits and phenolic compounds (i.e., one class of Taleghani A, et al. / IJPS 2021; 17 (1): 51-68 bioactive phytochemicals) previously reported countries, there are a limited number of studies in the literature include phenolic acids (i.e., are on the profiles of these compounds in the chlorogenic, syringic, caffeic, sinapic, ferulic, Iranian cultivar. In this paper, considering the p-coumaric, ellagic, cinnamic, and gallic structural diversity of the active compounds of acids), tannins (i.e., ellagic acid derivatives, pomegranates, a cultivar of p. granatum with such as punicalin, punicalagin, pedunculagin, black color was selected to investigate the and ellagitannins), and flavonoids (i.e., diversity of anthocyanins and non- anthocyanins, such as delphinidin, anthocyanins in PPs using the HPLC and mass pelargonidin, cyanidin, and their derivatives, spectrometry (MS) techniques. Firstly, and anthoxanthins, such as epicatechin, different fractions of PPs (i.e., methanol, catechin, and quercetin) [3-5]. Pomegranates ethanol acetone, and ethyl acetate) were have a large variety of colors from white to red evaluated for antioxidant activity using 2,2- and dark red. The red color and mild diphenyl-1-picrylhydrazyl (DPPH) free radical astringency are the characteristics of scavenging in vitro assay. Among different pomegranates related to polyphenol fractions of PPs, the methanolic and ethanolic constituents [6]. The color of PPs is due to the extracts were chosen for the characterization presence of anthocyanins (i.e., one class of of phenolic compounds due to the highest flavonoids). Cultivars with a dark red color amount of antioxidant activity. possess higher antioxidant activity than other portions [4, 7]. The identification and 2. Materials and Methods characterization of secondary metabolites in 2.1. Solvents and Reagents this fruit are important due to their role in All reagents and solvents used for HPLC- reducing the risk of diseases, such as cancer, MS separation and identification were inflammation, and cardiovascular and purchased (Merck & Co., Inc., Germany) with neurodegenerative diseases [8-10]. Previous analytical or HPLC grade. Moreover, all other studies have reported a number of methods for solvents for extraction were also purchased the identification of phenolic compounds in (Merck & Co., Inc., Germany). pomegranates [11]. Recently, particular attention has been given to high-performance 2.2. Plant Materials liquid chromatography (HPLC) with mass Iranian pomegranate fruits of unknown spectrometric detection due to the limited cultivar obtained from Ghaemshahr, Iran, were availability of reference standards and difficult washed and steamed (5 min) for enzyme identification of compounds only based on inactivation. A voucher number (803885) was ultraviolet spectra [12, 13]. Although there deposited in the Herbarium of Gonbad Kavous have been many studies carried out on the University, Gonbad, Iran. evolution of phenolic compounds in pomegranate cultivars grown in Iran and other 52 Phenolic Profiles in Peel of Iranian Pomegranate 2.3. Extracts Preparation %DPPH scavenging = [Ac-As/Ac] × 100 At first, the peels were lyophilized and where As is the absorbance of the sample, ground with a blender. Then, each extract was while Ac is the absorbance of control. Different obtained as it will be described. Subsequently, concentrations of extracts inhibiting 50% the dried powder was separately extracted with DPPH (IC50) were calculated by the ethyl acetate, acetone, methanol, and ethanol concentration of the extracts against the for the evaluation of the antioxidant activity. inhibition (%) of DPPH. 2.4. Quantification of Antioxidant Activity 2.5. Extraction of Anthocyanins The antioxidant potential of pomegranate The peel powder (1.0 g) was sonicated in fractions (i.e., methanol, ethanol acetone, and 30 mL of methanol (containing 0.1 % HCl) for ethyl-acetate) was determined by DPPH free 30 min. The obtained hydroalcoholic extract radical scavenging assay. The DPPH reduced was centrifuged at 5,000 rpm for 30 min and by an antioxidant, which can donate hydrogen. dried in a rotary evaporator under vacuum at The changes in color were measured from 35°C [7]. deep violet to light yellow using an ultraviolet- visible light spectrophotometer. Firstly, dried 2.6. Extraction of Non-anthocyanin powder of peel was separately extracted with Polyphenolics ethyl acetate, acetone, methanol, and ethanol. The plant extract was prepared as described In order to determine the radical scavenging in a study by Zahin et al. [15]. The methanolic capacity of the different concentrations of and ethanolic extracts of P. granatum were extracts against stable DPPH, a slightly gained by a continuous stirring of the dried modified method was spectrophotometrically peels at ambient temperature for 2 days. used as it will be described [14]. Briefly, 50 μl Furthermore, at the end of the extraction, the of different concentrations of the obtained extracts were separately filtered to make extracts (35-250 µg/ml) were mixed with 50 µl methanol and ethanol fractions, and the fresh of the 0.1 mM solution of methanolic DPPH. solvent was added to the plant materials. The The 50-µL methanol was employed as a obtained extracts were concentrated using a control in the experiment. After 30 min of rotary evaporator for dryness. A crude extract incubation at 37ºC, the absorbance of the was obtained after the removal of the samples using a microplate reader was extraction solvent and stored at 4°C in the dark spectrophotometrically read at 517 nm. until further testing. A stock solution of 1 Butylated hydroxyl toluene (BHT) within the mg/ml in the water of LC-MS grade was range of 35-250 µg/ml was used as a positive prepared and 2 µl was injected for LC-MS control. The antioxidant activity as percentage analysis. inhibition was calculated using the following equation: 53 Taleghani A, et al. / IJPS 2021; 17 (1): 51-68 2.7. High-Performance Liquid 3. Results and Discussion Chromatography-Mass Spectrometry (LC-MS) 3.1. Antioxidant Activity The method of Zahin et al. [15] was used The PPs have antioxidant activities due to a for the LC-MS analysis of the secondary good source of phenolic compounds (e.g., metabolites. The HPLC (Shimadzu, Tokyo, anthocyanins, quercetin, catechin, Japan) system coupled with a mass gallotannins, ferulic acid, ellagitannins, and spectrometer, which combines an AB SCIEX ellagic and gallic acids). The obtained results 3200 Q-TRAP with a Turbo V electrospray of the current study are in agreement with the ionization (ESI) source, was developed in the antioxidant activities of PPs reported in the present study. All the experiments were literature from different regions. The findings performed using a Thermo scientific liquid of studies have shown that methanol, acetone, chromatography system connected to ESI. The and aqueous extracts of Tunisian
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