9,10-Diphenyl-9,10-epidioxyanthracene, C(26)H(18)O(2), (I), was accidentally used in a photooxygenation reaction that produced 9,10-dihydro-10,10-dimethoxy-9-phenylanthracen-9-ol, C(22)H(20)O(3), (II). In both compounds, the phenyl rings are approximately orthogonal to the anthracene moiety. The conformation of the anthracene moiety differs as a result of substitution. Intramolecular C-H.O interactions in (I) form two approximately planar S(5) rings in each of the two crystallographically independent molecules. The packing of (I) and (II) consists of molecular dimers stabilized by C-H.O interactions and of molecular chains stabilized by O-H.O interactions, respectively.
Kacip Fatimah (Labisia pumila Blume), one of the most famous and widely used herbs, especially in Southeast Asia, is found to have interesting bioactive compounds and displays health promoting properties. In this study, the antioxidant activities of the methanol extracts of leaves, stems and roots of three varieties of L. pumila (var. alata, pumila and lanceolata) were evaluated in an effort to compare and validate the medicinal potential of this indigenous Malaysian herb species. The antioxidant activity determined by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay, as well as the total amount of phenolics and flavonoids were the highest in the leaves, followed by the stems and roots in all the varieties. A similar trend was displayed by the ferric reducing antioxidant potential (FRAP) activity, suggesting that the L. pumila varieties possess high foliar antioxidant properties. At low FRAP activity concentrations, the values of the leaves' inhibition activity in the three varieties were significantly higher than those of the stems and roots, with var. alata exhibiting higher antioxidant activities and total contents of phenolics and flavonoids compared to the varieties pumila and lanceolata. The high production of secondary metabolites and antioxidant activities in var. alata were firmly related to low nitrogen content and high C/N ratio in plant parts. The study also demonstrated a positive correlation between secondary metabolite content and antioxidant activities, and revealed that the consumption of L. pumila could exert several beneficial effects by virtue of its antioxidant activity.
A new computational approach for the determination of 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity (DPPH-RSA) in food is reported, based on the concept of machine learning. Trolox standard was mix with DPPH at different concentrations to produce different colors from purple to yellow. Artificial neural network (ANN) was trained on a typical set of images of the DPPH radical reacting with different levels of Trolox. This allowed the neural network to classify future images of any sample into the correct class of RSA level. The ANN was then able to determine the DPPH-RSA of cinnamon, clove, mung bean, red bean, red rice, brown rice, black rice and tea extract and the results were compared with data obtained using a spectrophotometer. The application of ANN correlated well to the spectrophotometric classical procedure and thus do not require the use of spectrophotometer, and it could be used to obtain semi-quantitative results of DPPH-RSA.
The present study was conducted to determine the effect of air (AD), oven (OD) and freeze drying (FD) on the free radical scavenging activity and total phenolic content (TPC) of Cosmos caudatus and the effect of storage time by the comparison with a fresh sample (FS). Among the three drying methods that were used, AD resulted in the highest free radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) (IC50 = 0.0223 mg/mL) and total phenolic content (27.4 g GAE/100 g), whereas OD produced the lowest scavenging activity and TPC value. After three months of storage, the dried samples showed a high and consistent free radical scavenging activity when compared to stored fresh material. The drying methods could preserve the quality of C. caudatus during storage and the stability of its bioactive components can be maintained.
In this work, the bioactive compounds which was obtained by extracting Quercus infectoria via two extraction methods; Soxhlet and supercritical carbon dioxide (SC-CO2) extraction, were analyzed using total phenolic content and DPPH (2,2-diphenyl-1-picryl hydrazyl) free radical scavenging activity analysis. The aim of this study is to compare the total phenolic content and antioxidant activity of Quercus infectoria extract acquired from SC-CO2 extraction with those from Soxhlet extraction method. The results showed the used of SC-CO2 extraction give the lowest extraction yield as compared to Soxhlet extraction. The selectivity of Q. infectoria extracts using SC-CO2 extraction was better which in contrast with Soxhlet extraction method since it shows higher total phenolic content (143.75 ± 1.06 mg GAE/g sample). This study also revealed that the extracts from both extraction methods can posses’ antioxidant activity and comparable to those obtained from commercial antioxidant.
This study aimed to optimise potential extraction conditions using response surface methodology (RSM) for yielding maximum levels of total phenolic content (TPC) and 2,2-diphenyl-1-picrylhydrazyl radical (DPPH•) scavenging capacity of henna (Lawsonia inermis) stems. The ranges for selected independent variables, namely acetone concentration (20−90%, v/v), extraction time (10−90 min), and extraction temperature (25−45°C) were identified by screening tests. Optimum conditions obtained for extraction of TPC were 47.0% acetone, extraction time of 47.6 min and extraction temperature of 37.3oC. The result also showed that 75.8% acetone, extraction time of 26.2 min and extraction temperature of 41oC yielded the highest DPPH• scavenging capacity. The optimized extraction conditions have resulted in TPC and DPPH• scavenging capacity of 5232.4 mg GAE/100 g DW and 6085.7 mg TE/100 g DW, respectively which similar to the predicted values. Therefore, RSM has successfully optimized the extraction conditions for TPC and radical scavenging capacity of henna stems.
Medicinal properties of Malaysian Curcuma caesia have not been studied extensively, even though it has been used as a traditional remedy. This study examined the effects of various extraction temperatures (30, 40, 50, 60, 70oC) using a high frequency (40 kHz) ultrasonic extraction method, time (30,60,90 and 120 minutes), pH (1,2,3,4,5,6,7,8,9,10) on the extraction yield of total phenolics and DPPH (2,2-diphenyl-1-picrylhydrazyl) scavenging activities from C. caesia rhizome. Extraction was most efficient at pH 6.0, while the extraction time of 30 minutes and temperature of 60oC was the best in terms of total phenolics content and DPPH scavenging activity. This study is important due to its ability to improve extraction of total phenolics compound using ultrasonic extraction method while maintaining a relatively high DPPH scavenging activity of the extracts.
The aim of this study is to compare antioxidant level and activities (i.e. primary and secondary) in pulps and peels of two species of dragon fruits, Hylocereus undatus (white dragon fruit) and Hylocereus polyrhizus (red dragon fruit). Total phenolic content (TPC) assay demonstrated that peels of both Hylocereus species contained higher phenolic content than the pulps. The phenolic content in peels of H. undatus was higher than H. polyrhizus, but the phenolic content in pulps of H. undatus was much lower than H. polyrhizus. 2, 2, diphenyl-1-picrylhydrazyl (DPPH) assay showed that radical scavenging activities of peels for both species were higher than the pulps. For ferrous ion chelating (FIC) assay, peels and pulps of both Hylocereus species showed moderate metal ion chelating effect as compared to EDTA. Overall, the results suggested that the TPC showed good relationship with the primary antioxidant activities for general comparison between the peels and the pulps.
Herbal tea is widely consumed around the world because people believed that it contained high amount of antioxidant. However, usage of different maturity of the plants as raw materials could affect the antioxidant capacities in herbal tea. Hence, this paper reports the antioxidant activity of herbal tea prepared from Cosmos caudatus at different maturity namely young, mature and old leaves. The analyses carried out were total phenolic content (TPC), total flavonoid content (TFC), ferric reducing antioxidant power (FRAP) and DPPH (2-2-diphenyl- 1-picrylhydrazyl) radical scavenging assays. Based on the results obtained, herbal tea prepared from young leaves had significantly strong (p
In this work, polymers of poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-triphenylamine] with side chains containing: pyrene (C1), diphenyl (C2), naphthalene (C3), and isopropyl (C6) structures were synthesized via a Suzuki coupling reaction. The structures were verified using NMR and cyclic voltammetry measurements provide the HOMO and LUMO of the polymers. The polymer with pyrene (C1) and naphthalene (C3) produced photoluminescence in the green while the polymer with the side chain containing diphenyl (C2) and isopropyl (C6) produce dual emission peaks of blue-green photoluminescence (PL). In order to examine the electroluminescence properties of the polymers, the solutions were spin-coated onto patterned ITO anode, dried, and subsequently coated with an Al cathode layer to form pristine single layer polymer LEDs. The results are compared to a standard PFO sample. The electroluminescence spectra resemble the PL spectra for C1 and C3. The devices of C2, C3, and C6 exhibit voltage-dependent EL. An additional red emission peak was detected for C2 and C6, resulting in spectra with peaks at 435 nm, 490 nm, and 625 nm. The effects of the side chains on the spectral characteristics of the polymer are discussed.
2,4-Dimethylbenzoylhydrazones 1-30 were synthesized by condensation reactions of 2,4-dimethylbenzoylhydrazide with various aromatic aldehydes and characterized. The assigned structures of compounds 10, 15 and 22 were further supported by single-crystal X-ray diffraction data. The synthesized compounds were evaluated for their in vitro DPPH radical scavenging activity. They exerted varying degree of scavenging activity toward DPPH radical with IC₅₀ values between 25.6-190 µM. Compounds 1, 4, 2, 3, 7, and 6 have IC₅₀ values of 25.6, 28.1, 29.3, 29.8, 30.0 and 30.1 µM respectively, showing better activity than an n-propyl gallate standard (IC₅₀ value = 30.30 µM). For super oxide anion scavenging activity compounds 1, 2 and 3 with IC₅₀ values of 98.3, 102.6, and 105.6, respectively, also showed better activity than the n-propyl gallate standard (IC₅₀ value = 106.34 µM).
The aim of this study was to determine the antioxidant activities of dietary bitter melon fruit supplemented in male rat model. In this study, three common tests for measuring antioxidant activity of the bitter melon were evaluated using 2, 2-diphenyl-l-picrylhydrazyl assay (DPPH assay), total phenolic acid assay (TPC assay) and Ferric reducing ability of plasma assa. (FRAP assay). Results showed that the extracting solvent significantly (P
This study investigated the antioxidant activity and functional properties of fractionated cobia skin gelatin hydrolysate (CSGH) at different molecular weights (10, 5 and 3 kDa). Antioxidant activities studied included reducing power, ferrous ion chelation, DPPH (1, 1- diphenyl-2- picrylhydrazyl) radical scavenging, and superoxide anion scavenging. Functional properties studied included emulsifying and foaming properties as well as fat and water binding capacity. Results showed significant differences (p
Quercus infectoria gall, which is known as manjakani in Malaysia, was traditionally used in treating diseases. The bioactive compounds from the galls can be extracted using various extraction methods. In this study, supercritical carbon dioxide (SC-CO2) extraction was used to study the effects of CO2 flow rate on the yield, total phenolic content and antioxidant activity of Q. infectoria extract by fixing the pressure and temperature at the highest density (P: 30 MPa, T: 40°C). The results were compared with those acquired from the Soxhlet extraction method. The results showed that the Soxhlet extraction had a higher percentage of extraction yield than SC-CO2 extraction. The selectivity of Q. infectoria extracts using SC-CO2 extraction was better than the Soxhlet extraction method. Meanwhile, the extraction efficiency using the SC-CO2 extraction ranged from 46% to 53%. The SC-CO2 extraction also yielded higher total phenolic content than using the Soxhlet extraction method when 2 mL/min of CO2 flow rate was applied (203.53 mg GA/g sample). This study also revealed that the extracts from the SC-CO2 extraction showed a better radical scavenging activity compared to the Soxhlet extraction when analysed using DPPH (2,2-diphenyl-1-picryl hydrazyl) radical scavenging activity assays.radical scavenging activity compared to the Soxhlet extraction when analysed using DPPH (2,2-diphenyl-1-picryl hydrazyl) radical scavenging activity assays.
This study aimed to assess the effects of fresh, thermal drying method (vacuum oven drying), and nonthermal drying method (freeze drying) on the antioxidant activities of leaves and berries of Cayratia trifolia using ferric reducing antioxidant power (FRAP) and 1,1-diphenyl-1-picrylhydrazyl radical scavenging capacity (DPPH) assays. The total phenolic content (TPC) and flavonoid content (TFC) of the leaves and berries of C. trifolia were also measured. Based on the results obtained, the TPC, TFC, and antioxidant activities of the leaves and berries were arranged in the following order: freeze-dried sample with methanol extraction > vacuum-dried sample with methanol extraction > freeze-dried sample with water extraction > vacuum-dried sample with water extraction > fresh sample with methanol extraction > fresh sample with water extraction. The results showed a significant difference (p<0.05) between the fresh and dried samples. In conclusion, freeze drying was found to be a good method for maintaining TPC, TFC, and antioxidant activities by FRAP and DPPH methods in the leaves and berries of C. trifolia.
A study was conducted to investigate the antiviral activity of aqueous extracts from Orthosiphon stamineus (OS).
Extraction was done using different parts of OS. The whole plant except root (WPOS), leaves (LOS) and flowers (FOS) of
OS were extracted using aqueous extraction method. Cytotoxicity was assessed using 3-(4,5-dimethylthiazol-2,5-diphenyl
tetrazolium bromide (MTT) assay. Plaque reduction assays were carried out to evaluate the antiviral activity of OS extract
against herpes simplex virus type 1 (HSV-1). These include post-treatment, pre-treatment and virucidal assays. High
antiviral activity was observed in post-treatment and virucidal assay with 100% reduction of HSV-1 plaque at 0.39 mg/
mL in LOS, FOS and WPOS. In pre-treatment assay, 79%, 84% and 97% plaque reduction using the same concentration
was observed in FOS, LOS and WPOS, respectively. In conclusion, this study showed that OS aqueous extract has promising
potential to be explored as anti-HSV-1 agent regardless of the mode of treatment.
The antiradical efficiency (AE) and kinetic behavior of a new ferulate-based protic ionic liquids (PILs) were described using 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical assay. The reduction of the DPPH free radical (DPPH•) was investigated by measuring the decrease in absorbance at 517 nm. The time to reach steady state for the reaction of parent acid (ferulic acid) and synthesized PILs with DPPH• was continuously recorded for 1 h. Results revealed that the AE of 2-butylaminoethanol ferulate (2BAEF), 3-dimethylaminopropanol ferulate (3DMAPF) and 3-diethylaminopropanol ferulate (3DEAPF) PILs have improved compared to ferulic acid (FA) as the reaction class changes from low to medium. This attributed to the strong hydrogen abstraction occurred in the PILs. Furthermore, these PILs were found to have a good kinetic behavior compared to FA due to the high rate constant (k₂) (164.17, 242.84 and 244.73 M-1 s-1, respectively). The alkyl chain length and more alkyl substituents on the nitrogen atom of cation were believed to reduce the cation-anion interaction and speed up the hydrogen atom transfer (HAT) and electron transfer (ET) mechanisms; hence, increased rate constant was observed leading to a strong antioxidant activity of the synthesized PILs.
Antioxidant capacities of ethylacetate, butanol, and water fractions of peel, pulp, and seeds of Canarium odontophyllum Miq. (CO) were determined using various in vitro antioxidant models. Ethylacetate fraction of peel (EAFPE) exhibited the highest total phenolic (TPC), total flavonoid content (TFC), and antioxidant activities compared to pulp, seeds, and other solvent fractions. Antioxidant capacities were assayed by total antioxidant capability, 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical activity, ferric reducing antioxidant power (FRAP), and hemoglobin oxidation assay. Total phenolic content of ethylacetate fractions was positively correlated with the antioxidant activity. This is the first report on the antioxidant activities from CO fruit fractions. Thus, EAFPE can be used potentially as a readily accessible source of natural antioxidants and as a possible pharmaceutical supplement.
The methanol extract of the dried ripe fruits of Alpinia rafflesiana was investigated for its DPPH free radical scavenger constituents. 2',3',4',6'-Tetrahydroxychalcone (7), which has never been isolated from natural sources was found to be most active as a DPPH free radical scavenger with the IC50 value of 55 microM. Other known compounds isolated from this species include 5,6-dehydrokawain (1), flavokawin B (2). 1,7-diphenyl-5-hydroxy-6-hepten-3-one (3), (-)-pinocembrin (4), cardamonin (5) and (-)-pinostrobin (6). The DPPH free radical scavenger compounds were detected using TLC autographic analysis. The percentage inhibition of DPPH free radical scavenging activity was measured on isolates (5-7) using colorimetric analysis.
Clausena excavata (Lour.), locally known as "Kemantu hitam," is a common plant in Malaysian folklore medicine. This study evaluated the antioxidant properties of the solvent extracts of C. excavata leaves and determined the acute toxicity of methanolic extract C. excavata (MECE) leaves in Sprague-Dawley rats. Harvested leaves were dried and subjected to solvent extraction using petroleum ether, chloroform, ethyl acetate and methanol in succession. The antioxidant activity of each extract was determined using the ferric-reducing antioxidant power (FRAP) and 2,2-diphenyl-1-picryl dihydrazyl (DPPH) radical scavenging activity. The total phenolic content (TPC) and total flavonoids content (TFC) were estimated by Folin-Ciocalteu and ethanolic aluminium chloride method, respectively. The chloroform extract was found to be highest in flavonoid content, while the methanolic extract showed the highest TPC and antioxidant activity. There was no mortality in rats treated with MECE leaves even at a high dose of 5000 mg/kg body weight. However, the MECE leaves produced mild to moderate pathological changes in the liver and kidneys, shown by mild degenerative changes and leucocyte infiltration. The extract did not affect the haematological parameters or relative weights of the liver or kidneys. Overall, the MECE leaves have potent antioxidant activity and are presumed safe to be used orally as health-promoting product at low to moderate doses.