Synthesis of a series of benzimidazole-ornamented pyrazoles, 6a-6j has been obtained from arylhydrazine and aralkyl ketones via a multistep synthetic strategy. Among them, a hybrid-possessing para-nitrophenyl moiety connected to a pyrazole scaffold (6a) exerted the highest anti-inflammatory activity, which is superior to the standard, diclofenac sodium. While executing the 2,2-diphenyl-1-picrylhydrazyl radical-scavenging activity, a hybrid-possessing para-bromophenyl unit integrated at the pyrazole structural motif (6i) exhibited the highest activity among the hybrids examined. Besides, evaluation of anticancer potency of the synthesized hybrids revealed that the one containing a para-fluorophenyl unit tethered at the pyrazole nucleus (6h) showed the highest activity against both the pancreatic cancer cells (SW1990 and AsPCl) investigated. Considerable binding affinity between B-cell lymphoma and the hybrid, 6h has been reflected while performing molecular docking studies (-8.65 kcal/mol). The outcomes of the investigation expose that these hybrids could be used as effective intermediates to construct more potent biological agents.
The amino-acid composition, 2, 2-Diphenyl-1-picryhydrazyl (DPPH) radical-scavenging activity, and peptide patterns of tilapia protein hydrolysates produced by the enzymatic hydrolysis of Alcalase (AH), Flavourzyme (FH) and Protamex (PH) for 5h using pH-stat method were studied. The ratio of essential amino acids to non-essential amino acids increased after hydrolysis in all samples; however, no significant differences among them were observed. AH had a highest (P < 0.05) DPPH radical-scavenging activity, but no significant difference in the DPPH between FH and PH was observed. SDS-PAGE patterns for all the hydrolysates showed significant (P < 0.05) reduction in the number and the intensity of the bands with increasing time of hydrolysis. Flavourzyme showed the lowest rate of hydrolytic activity towards the tilapia mince.
The aim of this study is to determine the antioxidant capacity of underutilized fruits in Malaysia namely Milk apple (Syzygium malaccense), Malay apple (Syzygium malaccense (L.) Merr. and Perry), and Water apple (Syzygium aqueum). Synthetic antioxidants (BHA and BHT) commonly used in the food industries may not be as safe as it was presumed earlier. As BHA and BHT may be carcinogenic, it is important to look for new sources of natural antioxidants from fruits and vegetables. Freeze dried samples extracted with acetone and water were measured by ferric 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and Ferric Reducing Antioxidant Power (FRAP) assays. Acetone extract (50%) showed higher values for both DPPH and FRAP assays compared with water extract. Milk apple has the highest DPPH value of 95.26% inhibition of DPPH. Milk apple also showed the highest FRAP value with 8722.22 µM of Fe (II) per gram of freeze dried sample. There was a significant difference (P < 0.05) in the types of extraction used. Antioxidant capacities of the samples are in the following order: Milk apple > Malay apple > Water apple. Proximate compositions and mineral contents of the samples were determined too. The samples can be used as a source of natural antioxidants.
Vitamin E is known to have potent antioxidant activity and plays an important role in reducing oxidative stress, a pivotal step in atherogenesis. However, several randomised clinical trials using α-tocopherol have failed to demonstrate consistent beneficial effects of antioxidants against atherosclerosis and clinical endpoints. Tocotrienol, a vitamin E compound analogue is shown to have more potent antioxidant activity compared to tocopherol. Finding the optimal anti-oxidative dose is crucial and may effectively be applied for cardioprotection in human. The objective of this study was to determine the optimal dose of tocotrienol rich fraction (TRF) with highest antioxidant activity in vitro using the ferric thiocyanate (FTC), 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and 2’, 7’- dichlorofluorescein diacetate (DCFHDA) assays. It was found that TRF exhibited potent antioxidant and free radical scavenging activities with an IC50 of 22.10 + 0.01 µg/ml. In all assays, TRF had optimal antioxidant activity at moderate concentrations (10-100 µg/ml). In conclusion, TRF has potent antioxidant activity, which is optimal at moderate concentrations.
In the last decade, non-thermal processing for inactivating microorganisms has been developed in response to the worldwide interest for more fresh and improved quality of food products. Winter melon is a very perishable fruit, hence, processing into puree is a necessity. However application of heat in the production of puree could affect the nutritional values, thus, application of non thermal treatment in combination with preservation method is significant for this fruit. This study was conducted to evaluate the effect of non-thermal processing in combining with preservation method on antioxidant activity, level of key antioxidant groups (total phenolic and ascorbic acid content) and the color of winter melon puree. Total phenolic content (TPC) was measured using Folin-Ciocalteu reagent. Ascorbic acid (AA) was determined using 2,6-dichlorophenol-indophenol titration method. Antioxidant activity were determined using four antioxidant assays namely Ferric Reducing Antioxidant Potential (FRAP), Oxygen Radical Absorbance Capacity (ORAC), 2,2-Diphenyl-1-Picrylhydrazyl (DPPH) and β-Carotene Bleaching Assays. For the TPC, puree with pH 3 (28.5±1.3 GAE/g fresh weight) exhibited high in TPC as compared to puree with pH 3.5 and unprocessed puree. In contrast, unprocessed puree contains significantly high ascorbic acid (AA) content (35.9 ± 1.8 mg/100 g fresh mass) as compared to pH 3.0 and pH 3.5 purees. In general, antioxidant activity for all assays of pH 3.0 and pH 3.5 purees were significantly higher (p
The aim of this study is to determine the total phenolic content and primary antioxidant activity of methanolic and ethanolic extracts of four aromatic plants’ leaves namely knotweed (Polygonum minus), curry (Murraya koenigii), kaffir lime (Citrus hysrix) and fragrant screwpine (Pandanus odurus). Total phenolic content (TPC) assay using Folin-Ciocalteu method was used to assess the presence and level of phenolic compounds in each sample. The present study showed that both methanolic and ethanolic extracts of P. minus had the highest TPC and followed by M. koenigii, C. hystrix and P. odorus. Primary antioxidant activity in terms of free radical scavenging activities of both methanolic and ethanolic extracts was then measured by 2, 2, diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging activity assay. The lowest EC50 values based on the DPPH. radical scavenging activity were shown by P. minus extracts as compared to the other samples. For both ethanolic and methanolic extracts, the correlations between TPC and EC50 based on the DPPH. radical scavenging activity assay were negative and weak. Relatively, the present results suggest that of the four aromaticplants, P. minus and M. koenigii have shown potential as sources of natural antioxidants.
This article discusses on the natural compounds from the ant plant (Myrmecodia species, family: Rubiaceae). The ethyl
acetate (EtOAc) extract from the tuber of M. platytyrea was fractionated by using medium pressure liquid chromatography,
giving eight fractions (F1-F8). Those fractions were evaluated using the 2, 2-diphenyl-1-picrylhydrazyl (DPPH)
assay. Fraction F5 was recorded as potent (EC50 = 21.57 ± 1.40 µg/mL). Then, it was purified by using column
chromatography (CC) (mobile phase = chloroform: EtOAc). From the CC, ten fractions (F5F1-F5F10) were obtained
and compound (1) was isolated from F5F3 via preparative thin layer chromatography (TLC). After spraying with
anisaldehyde-sulphuric reagent, compound (1) gave a green TLC spot (Rf
= 0.65, 100% CHCl3
, multiple development).
The 1
H-Nuclear Magnetic Resonance (NMR) spectroscopy (500 MHz, CDCl3
) was performed to determine the chemical
framework of (1). This compound was identified as morindolide, having an iridoid structure. Meanwhile, the mass
spectra for compounds (2) and (3) were analysed. The data presented the molecular ion at m/z 375 [M-H]- and 255,
suggesting the formulation of 2-(2-methylbutyryl)phloroglucinol glucoside and a flavanone, respectively. From the
literature, compound (1) was firstly isolated from a Chinese natural medicine, the dried root of Morinda officinalis
(family: Rubiaceae). The flavonoids are also included as the biologically active compounds from Myrmecodia. In
short, this is the first occurrence of morindolide from the ant plant.
Propolis contains high concentrations of polyphenols, flavonoids, tannins, ascorbic acid, and reducing sugars and proteins. Malaysian Propolis (MP) has been reported to exhibit high 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity and ferric reducing antioxidant power (FRAP) values. Herein, we report the antioxidant properties and cardioprotective properties of MP in isoproterenol- (ISO-) induced myocardial infarction in rats. Male Wistar rats (n = 32) were pretreated orally with an ethanol extract of MP (100 mg/kg/day) for 30 consecutive days. Subcutaneous injection of ISO (85 mg/kg in saline) for two consecutive days caused a significant increase in serum cardiac marker enzymes and cardiac troponin I levels and altered serum lipid profiles. In addition significantly increased lipid peroxides and decreased activities of cellular antioxidant defense enzymes were observed in the myocardium. However, pretreatment of ischemic rats with MP ameliorated the biochemical parameters, indicating the protective effect of MP against ISO-induced ischemia in rats. Histopathological findings obtained for the myocardium further confirmed the biochemical findings. It is concluded that MP exhibits cardioprotective activity against ISO-induced oxidative stress through its direct cytotoxic radical-scavenging activities. It is also plausible that MP contributed to endogenous antioxidant enzyme activity via inhibition of lipid peroxidation.
Water extract of Lentinus squarrosulus mycelia was analysed for nutritional content, antioxidant capacity, and antiulcer ability. The extract contains high protein (57.6 g/100 g) and low total fat (0.5 g/100 g) and is rich in magnesium (0.4 g/100 g), potassium (3.8 g/100 g), vitamins B(1) (1.42 mg/100 g), and B(3) (194.29 mg/100 g) with total phenolic content of 39.16 mg/100 g. The cupric reducing antioxidant capacity and 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity of the extract were A(450) of 0.20 ± 0.03 at 0.5 mg/ml and IC(50) of 14.29 mg/ml, respectively. Oral feeding of L. squarrosulus extract (250 mg/kg) offered significant gastric mucosal protection of Sprague-Dawley rats compared to cimetidine (50 mg/kg). The ulcer healing rate of ulcerated rats after 24, 48, and 72 hours of treatment was 82%, 90%, and 100%, respectively. The IL-1β level in the serum and the NF-κB level in the tissues indicate that the healing potential was associated with attenuation of proinflammatory cytokines.
Protein hydrolysates produced from different food sources exhibit therapeutic potential and can be used in the management of chronic diseases. This study was targeted to optimise the conditions for the hydrolysis of stone fish protein to produce antioxidant hydrolysates using central composite design (CCD) by response surface methodology (RSM). The stone fish protein was hydrolysed under the optimum predicted conditions defined by pH (6.5), temperature (54°C), E/S ratio (1.5%), and hydrolysis time (360 min). The hydrolysates were then evaluated for 2,2-diphenyl-1-picrylhydrazyl radical (DPPH•) scavenging activity and ferrous ion- (Fe2+-) chelating activity. Results validation showed no significant difference between the experimental values of DPPH• scavenging activity (48.94%) and Fe2+-chelating activity (25.12%) obtained at 54.62% degree of hydrolysis (DH) compared to their corresponding predicted values of 49.79% and 24.08% at 53.08% DH, respectively. The hydrolysates demonstrated non-Newtonian behavior (n < 1) with stronger shear-thinning effect and higher viscosities at increasing concentration. Thus, RSM can be considered as a promising strategy to optimise the production of stone fish protein hydrolysates containing antioxidant peptides. It is hoped that this finding will enhance the potential of stone fish protein hydrolysates (SHs) as therapeutic bioactive ingredient in functional foods development.
In the present study, in vitro antioxidant, free radical scavenging capacity, and hepatoprotective activity of methanol extracts from Polyalthia longifolia and Cassia spectabilis were evaluated using established in vitro models such as ferric-reducing antioxidant power (FRAP), 2,2-diphenyl-1-picryl-hydrazyl (DPPH(•)), hydroxyl radical (OH(•)), nitric oxide radical (NO(•)) scavenging, metal chelating, and antilipidperoxidation activities. Interestingly, all the extracts showed considerable in vitro antioxidant and free radical scavenging activities in a dose-dependent manner when compared to the standard antioxidant which verified the presence of strong antioxidant compound in leaf extracts tested. Phenolic and flavonoid content of these extracts is significantly correlated with antioxidant capacity. Since P. longifolia extract was exhibited better in vitro antioxidant activities, it was subjected for in vivo hepatoprotective activity in paracetamol-intoxicated mice. Therapy of P. longifolia showed the liver protective effect on biochemical and histopathological alterations. Moreover, histological studies also supported the biochemical finding, that is, the maximum improvement in the histoarchitecture of the liver. Results revealed that P. longifolia leaf extract could protect the liver against paracetamol-induced oxidative damage by possibly increasing the antioxidant protection mechanism in mice. Our findings indicated that P. longifolia and C. spectabilis have potential as good sources of natural antioxidant/antiaging compounds.
Roots and leaves of the Cermela Hutan (Phyllanthus gomphocarpus Hook. F) plant were studied to determine antioxidant activity, phytochemical compounds, proportion of carbohydrate, crude protein, moisture, ash, fat, total phenolic content (TPC), and total flavonoid content (TFC).
There is no available information on physicochemical and antioxidant properties on Bangladeshi honey. We investigated five different monofloral and three different multifloral honey samples collected from different parts of Bangladesh.
The aim of this study was to produce a valuable protein hydrolysate from palm kernel cake (PKC) for the development of natural antioxidants. Extracted PKC protein was hydrolyzed using different proteases (alcalase, chymotrypsin, papain, pepsin, trypsin, flavourzyme, and bromelain). Subsequently, antioxidant activity and degree of hydrolysis (DH) of each hydrolysate were evaluated using DPPH• radical scavenging activity and O-phthaldialdehyde spectrophotometric assay, respectively. The results revealed a strong correlation between DH and radical scavenging activity of the hydrolysates, where among these, protein hydrolysates produced by papain after 38 h hydrolysis exhibited the highest DH (91 ± 0.1%) and DPPH• radical scavenging activity (73.5 ± 0.25%) compared to the other hydrolysates. In addition, fractionation of the most effective (potent) hydrolysate by reverse phase high performance liquid chromatography indicated a direct association between hydrophobicity and radical scavenging activity of the hydrolysates. Isoelectric focusing tests also revealed that protein hydrolysates with basic and neutral isoelectric point (pI) have the highest radical scavenging activity, although few fractions in the acidic range also exhibited good antioxidant potential.
Conjugated linoleic acids (CLAs) are a mixture of positional and geometric isomers of linoleic acid (LA) and believed to have many positive biological activities.
Two new xanthones, pyranocycloartobiloxanthone A (1) and dihydroartoindonesianin C (2), were isolated from the stem bark of Artocarpus obtusus Jarrett by chromatographic separation. Their structures were determined by using spectroscopic methods and comparison with known related compounds. Pyranocycloartobiloxanthone A (1) showed strong free radical scavenging activity by using DPPH assay as well as cytotoxicity towards K562, HL-60, and MCF7 cell lines.
The antioxidant properties of virgin coconut oil produced through chilling and fermentation were investigated and compared with refined, bleached and deodorized coconut oil. Virgin coconut oil showed better antioxidant capacity than refined, bleached and deodorized coconut oil. The virgin coconut oil produced through the fermentation method had the strongest scavenging effect on 1,1-diphenyl-2-picrylhydrazyl and the highest antioxidant activity based on the beta-carotene-linoleate bleaching method. However, virgin coconut oil obtained through the chilling method had the highest reducing power. The major phenolic acids detected were ferulic acid and p-coumaric acid. Very high correlations were found between the total phenolic content and scavenging activity (r=0.91), and between the total phenolic content and reducing power (r=0.96). There was also a high correlation between total phenolic acids and beta-carotene bleaching activity. The study indicated that the contribution of antioxidant capacity in virgin coconut oil could be due to phenolic compounds.
A new linderone A, namely 2-cinnamoyl-3-hydroxy-4, 5-dimethoxycyclopenta-2, 4-dienone (5), together with three known flavonoids (1-3) and one linderone (4), were isolated from the bark of Lindera oxyphylla. Extensive spectroscopic analysis including 1D and 2D-NMR spectra determined their sturctures. In addition, the antioxidant activity of all the compounds has been determined using 2, 2-diphenyl-1-picrylhydrazyl radical scavenging (DPPH), ferric reducing antioxidant power (FRAP) and ferrous ion chelating (FIC) methods. Compound 3 showed excellent DPPH scavenging activity with IC50% value of 8.5 ± 0.004% (μg/mL) which is comparable with vitamin C. This compound, also showed an absorbance value of 1.00 ± 0.06% through FRAP test when compared with Butyl Hydroxy Aniline (BHA). However, FIC showed low activity for all the isolated compounds (chelating activity less than 50%) in comparison with ethylene diamine tetra acetic acid (EDTA). Anticancer activity for all compounds has also been measured on A375 human melanoma, HT-29 colon adenocarcinoma, MCF-7 human breast adenocarcinoma cells, WRL-68 normal hepatic cells, A549 non-small cell lung cancer cells and PC-3 prostate adenocarcinoma cell line. Compound 1 showed A549=65.03%, PC-3=30.12%, MCF-7=47.67, compound 2 showed PC-3=90.13%, compound 3 showed MCF-7=79.57 and for compound 5 MCF-7 is 96.33.
A new xanthone, namely garcinexanthone G (1), along with eight known compounds, stigmasta-5,22-dien-3β-ol (2), stigmasta-5,22-dien-3-O-β-glucopyranoside (3), 3β-acetoxy-11α,12α-epoxyoleanan-28,13β-olide (4), 2,6-dimethoxy-p-benzoquinone (5), 1,3,5-trihydroxy-2-methoxyxanthone (6), 1,3,7-trihydroxyxanthone (7), kaempferol (8) and quercetin (9), were isolated from the stem bark of Garcinia atroviridis. Their structures were elucidated based on spectroscopic methods including nuclear magnetic resonance (NMR-1D and 2D), UV, IR, and mass spectrometry. All the isolated compounds were evaluated for their antioxidant properties based on the DPPH radical scavenging activities. Results showed that 1,3,7-trihydroxyxanthone and quercetin showed significant antioxidant activities with EC50 values of 16.20 and 12.68 μg/ml, respectively, as compared to the control, ascorbic acid (7.4 μg/ml).
Lipase-catalyzed transesterification of flaxseed oil with cinnamic acid (CA) or ferulic acid (FA) using an immobilized lipase from Candida antarctica (E.C. 3.1.1.3) was conducted to evaluate whether the lipophilized products provided enhanced antioxidant activity in the oil. Lipase-catalyzed transesterification of flaxseed oil with CA or FA produced a variety of lipophilized products (identified using ESI-MS-MS) such as monocinnamoyl/feruloyl-diacylglycerol, dicinnamoyl-monoacylglycerol and monocinnamoyl-monoacylglycerol. The free radical scavenging activity of the lipophilized products of lipase-catalyzed transesterification of flaxseed oil with CA or FA toward 2,2-diphenyl-1-picrylhydrazyl radical (DPPH.) were both examined in ethanol and ethyl acetate. The polarity of the solvents proved important in determining the radical scavenging activity of the substrates. Unesterified FA showed the highest free radical scavenging activity among all substrates tested while CA had negligible activity. The esterification of CA or FA with flaxseed oil resulted in significant increase and decrease in the radical scavenging activity compared with the native phenolic acid, respectively. Based on the ratio of a substrate to DPPH. concentration, lipophilized FA was a much more efficient free radical scavenger compared to lipophilized CA and was able to provide enhanced antioxidant activity in the flaxseed oil. Lipophilized cinnamic acid did not provide enhanced radical scavenging activity in the flaxseed oil as the presence of natural hydrophilic antioxidants in the oil had much greater radical scavenging activity.