Polyphenolic contents and antioxidant activities of aerial parts of Salvia multicaulis from the Iran flora

Abstract

Folk medicine sometimes involves the use of salvia species for therapeutic purposes. Polyphenols with the highest amounts included rosmarinic acid (7.358mg/g), catechin (1.5?mg/g), vanillin (1.00?mg/g), chlorogenic acid (0.53?mg/g), quercetin (0.16?mg/g), and p-coumaric acid (0.015). Furthermore, the results showed that S. multicaulis has a high content of total phenol (4.39?mg/g) and DPPH activity (8.44?mg/g). Salvia multicaulis could be potentially used as a medicinal plant because of its antioxidant activity and polyphenol content.     

Triterpenes and Phenolic Compounds from the Fungus Fuscoporia torulosa: Isolation,Structure Determination and Biological Activity

Investigation of the methanol extract of the poroid fungus Fuscoporia torulosa resulted in the isolation of a novel triterpene, fuscoporic acid (1), together with inoscavin A and its previously undescribed Z isomer (2 and 3), 3,4-dihydroxy-benzaldehide (4), osmundacetone (5), senexdiolic acid (6), natalic acid (7), and ergosta-7,22-diene-3-one (8). The structures of fungal compounds were determined on the basis of NMR and MS spectroscopic analyses, as well as molecular modeling studies. Compounds 1, 6–8 were examined for their antibacterial properties on resistant clinical isolates, and cytotoxic activity on human colon adenocarcinoma cell lines. Compound 8 was effective against Colo 205 (IC₅₀ 11.65 ± 1.67 µM), Colo 320 (IC₅₀ 8.43 ± 1.1 µM) and MRC-5 (IC₅₀ 7.92 ± 1.42 µM) cell lines. Potentially synergistic relationship was investigated between 8 and doxorubicin, which revealed a synergism between the examined compounds with a combination index (CI) at the 50% growth inhibition dose (ED₅₀) of 0.521 ± 0.15. Several compounds (1 and 6–8) were tested for P-glycoprotein modulatory effect in Colo 320 resistant cancer cells, but none of the compounds proved to be effective in this assay. Fungal metabolites 2–5 were evaluated for their antioxidant activity using the oxygen radical absorbance capacity (ORAC) and DPPH assays. Compounds 4 and 5 were found to have a considerable antioxidant effect with EC₅₀ 0.25 ± 0.01 (DPPH) and 12.20 ± 0.92 mmol TE/g (ORAC). The current article provides valuable information on both the chemical and pharmacological profiles of Fuscoporia torulosa, paving the way for future studies with this species.     

Phenolic content and antioxidant properties of seeds from different grape cultivars grown in Iran

This study investigated the antioxidant activity and phenolic composition of seed extracts from three grape cultivars grown in Iran. Folin Ciocalteu method was used for the determination of the total phenolic contents and GC–MS was used for the analysis of phenolic compositions. 1,1-diphenyl-2-picrylhydrazyl (DPPH) method was used to evaluate the antioxidant activity. The highest and the lowest total phenolic contents of seed extract were found in the black and green grape, respectively. The content of individual phenols such as Frulic acid, Gentistic acid, Syringic acid, (+) Catechin, Chlorogenic acid and (?)- Epicatchin gallate was cultivars dependent. The antioxidant activity of the seed extracts ranged from 34.03% (Green) to 53.63% (Black). Generally, the Black grape seed extract with the total phenolic content (3 ± 0.01 mg tannic acid/g DM), DPPH (53.63 ± 0.34%), IC₅₀ and AEAC (7.41 and 16.92 mg/mL) showed the highest level of total antioxidant capacity.     

一种半受阻酚类抗氧剂中间体的合成及抗氧化性能研究

采用2-甲基-6-叔丁基苯酚和丙烯酸甲酯为原料,通过迈克尔加成反应合成半受阻酚类抗氧剂中间体β-(3-甲基-5-叔丁基-4-羟基苯基)丙酸甲酯.条件优化实验确定该抗氧剂中间体的最佳合成工艺条件为:2-甲基-6-叔丁基苯酚与丙烯酸甲酯物质的量之比为1∶1.1,催化剂KOH与2-甲基-6-叔丁基苯酚的物质的量比为1∶10,丙烯酸甲酯滴加温度为90℃,丙烯酸甲酯滴加时间为30 min,反应温度为130℃,反应时间为5 h.在此条件下,半受阻酚类抗氧剂中间体β-(3-甲基-5-叔丁基-4-羟基苯基)丙酸甲酯的收率大于70%,熔程41.6℃~44.0℃.IR和1H NMR证实所合成目标产物的化学结构与其理论结构相一致.DPPH法测定半受阻酚类抗氧剂中间体清除自由基的性能,并与全受阻酚类抗氧剂中间体β-(3,5-二叔丁基-4-羟基苯基)丙酸甲酯进行对比.结果表明,由于邻位取代基的不对称效应,使得空间位阻较小的不对称抗氧剂中间体β-(3-甲基-5-叔丁基-4-羟基苯基)丙酸甲酯清除DPPH·的活性高于邻位取代基空间位阻较大的对称抗氧剂中间体清除DPPH·的活性.     

Integration of in silico and in vitro approaches to evaluate antioxidant and anticancer properties of Tribulus terrestris extracts

Plants have been found useful in treating many human diseases caused by bacteria and viruses. The ability to synthesize compounds by plant secondary metabolism makes them an invaluable source of pharmaceutical and therapeutic products. The present study was designed to evaluate the phytochemical constituents, antioxidant, and anticancer activities of Tribulus terrestris seed extracts on HepG2 cell lines. TPC and TFC contents were 51 ± 0.7 mg GAE/g and 66.5 ± 0.4 mg QE/g, respectively. The antioxidant profile of the T. terrestris revealed that all the extracts have antioxidant potential and display the highest antiradical behavior in the pattern of methanolic > acetonic > chloroform > n-hexane, through DPPH, FRAP, OH radical scavenging, and NO radical scavenging assays. The antioxidant activity explored at the cellular level against H₂O₂-induced DNA damage showed a dose-dependent antioxidant effect of T. terrestris. Moreover, the methanolic extracts of all plant extracts showed notable thrombolytic potentials, the percentage of clot lysis accounted for T. terrestris was 33%, 27%, 17%, and 6% which indicated the significant clot lysis of methanolic and acetonic extracts in contrast to positive and negative standards. The genotoxicity was assessed through comet assay which exposed that T. terrestris at a low dose (0.5 mg/mL) is considered to be safe for effective treatment. MTT assay using HepG2 cell lines revealed that the highest tested concentration i.e., 100 μg/mL of the methanolic extract resulted in 86% cell viability compared to the control group. In silico study, from 14 selected compounds, three compounds, Heptacosane, Apiol, and Palmitic acid showed an affinity with target protein 51X0. The present findings may serve as a guideline for the standardization and validation of natural drugs containing the T. terrestris as an ingredient.     

Optimization of polysaccharides extraction from quince peels: partial characterization,antioxidant and antiproliferative properties

Abstract

In this study, Box-Behnken Design was used to optimize the ultrasonic extraction of polysaccharides from quince peels (QPPs) by ascorbic acid and the effect of extraction temperature, extraction time and pH was evaluated. Under optimized conditions of temperature 90?°C, 60?min sonication time and pH?=?3.26, the extraction yield, the galacturonic acid yield and the concentration of sample required to scavenge 50% of 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic) acid (ABTS) values of QPPs were respectively 10.25%, 3.86% and 1.35?mg/mL. The QPPs extracted under optimum conditions was characterized by Fourier transform infrared spectroscopy (FTIR), Nuclear magnetic resonance (^1?H NMR) and Size exclusion chromatography (SEC/MALS/VD/DRI). The monosaccharide analysis revealed that arabinose was the most abundant, followed by galactose, glucose, mannose and xylose. Moreover, QPPs showed significant antioxidant activities (2,2-diphenyl-1-picrylhydrazyl (DPPH) and Ferric- reducing antioxidant power (FRAP)) and reduced viability of human Caco-2 and murine B-16 cell lines in a dose-dependent manner. Hence QPPs could be used as antitumor agent in functional foods andpharmaceutical industries.     

A new phenanthropyran and a new biphenanthrene from the rhizomes of Dioscorea septemloba and their antioxidant activities

Abstract

A new phenanthropyran, dioscorone B (1), and a new phenanthrene (2), together with seven known compounds (3–9), were isolated from the 75% ethanol extract of Dioscorea septemloba rhizomes. The chemical structures of these compounds were elucidated by comprehensive spectroscopic methods including NMR, HRESIMS, IR, and UV spectra. Compounds 1–5 were first isolated from genus Dioscorea. The proton and carbon chemical shifts of compounds 1–9 were unambiguously assigned based on the 1D-NMR and 2D-NMR data. Compounds 1–5 and 8–9 were first tested for their antioxidant activities. Compounds 1 and 2 showed excellent activities with IC₅₀ values of 0.07?±?0.10?μM and 0.13?±?0.09?μM, respectively.     

高速逆流色谱结合制备液相色谱法分离制备葡萄籽中的多酚

采用高速逆流色谱结合制备液相色谱法从葡萄籽乙醇提取物中分离得到了8种多酚。高速逆流色谱以上相为固定相,下相为流动相,主机转速为900 r/min,流速为2 mL/min,分离温度为25℃,检测波长为280 nm,利用正向和反向洗脱相结合的模式,在正丁醇-乙酸乙酯-水（1∶14∶15,v/v/v）和正己烷-乙酸乙酯-水（1∶10∶10,v/v/v）溶剂系统下从葡萄籽提取物中分离得到了5种多酚。原花青素B₁、原花青素B₂、没食子酸、表儿茶素没食子酸酯和儿茶素的纯度分别为98.5%、97.2%、98.3%、98.9%和96.7%。利用制备液相色谱法对高速逆流色谱分离成分进一步分离纯化,获得了表儿茶素、表没食子儿茶素没食子酸酯和没食子儿茶素没食子酸酯,纯度分别99.2%、99.3%和99.2%。该方法单次制备量均达到毫克级,简便、快速、分离纯度高,适合于葡萄籽中多酚的分离制备。     

Comparison on the antioxidant capacity of selected fruits and vegetables and their separations

Several kinds of fruits, including apple, pear, and grape, and vegetables, including onion and tomato, were studied in this paper. FRAP and DPPH assays were used to determine the antioxidant activity of ethanol extracts and their separations. After being extracted, different phenolic compounds were separated on Sephadex LH-20 column. EC1 and EC50 were used to show the ferric reducing ability and DPPH scavenging activity. The results indicated that the Fe-reducing ability order of different extracts was different with that of DPPH scavenging ability. The mutual effect of the substances in the mixture influenced the antioxidant activity of the separations. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 333–335, July–August, 2006.     

Antimicrobial and antioxidant activities of a new benzamide from endophytic Streptomyces sp. YIM 67086

A new benzamide (1) and four known compounds (2–5) were isolated from endophytic Streptomyces YIM67086, and their structures were determined as 2-amino-3,4-dihydroxy-5-methoxybenzamide (1), 4-hydroxy-3-methoxybenzoic acid (2), phenylacetic acid (3), N-acetyltyramine (4) and p-hydroxytruxinic acid (5). Compound 5 was first found in the microorganism. The antimicrobial activities of compounds 1–5 and antioxidant activity of compound 1 were investigated.     

石楠叶红、绿色素成分比较及抗氧化活性研究

采用多溶剂筛选最佳提取溶剂;以紫外分光光度法、高效液相色谱法、红外光谱法系统比较石楠红、绿色素成分的差别;同时考察红、绿色素对DPPH·清除能力、还原Fe3+能力和清除·OH自由基能力。结果以90%乙醇和乙酸乙酯-乙醇(1∶1)提取红色素、绿色素效果较好;通过显色反应、紫外光谱、红外光谱鉴别和高效液相色谱分析,基本确定红色素成分为黄酮类,绿色素成分为叶绿素类。抗氧化实验结果表明,在达到最大浓度0.34mg·m L-1时,石楠叶红、绿色素和维生素C对DPPH·清除率依次为79.6%,70.8%,66.9%,红、绿色素对·OH自由基的清除率依次为67.1%,51.2%,且红色素还原Fe3+能力较强。     

Isolation,structural elucidation and in vitro antioxidant activity of compounds from chloroform extract of Cedrus deodara (Roxb.) Loud.

This study was designed to isolate, characterise and explore in vitro antioxidant potential of compounds from the chloroform extract of Cedrus deodara wood belonging to Pinacae family. We have investigated the in vitro free radical scavenging activity of isolated compounds by measuring total antioxidant capacity (TAC) and reducing power ability. From the chloroform extract five sesquiterpenes namely atlantone, himaphenolone, atlantolone, deodardione and atlantone-2,3-diol were identified. Himaphenolone and deodardione from the chloroform extract of this plant have been isolated for the first time. A marked dose-dependent reducing power and strong TAC were found in favour of himaphenolone and atlantone-2,3-diol, respectively. Moreover, deodardione and atlantolone also exhibit good antioxidant potentials. However, atlantone has showed least antioxidant activity. In conclusion, the chloroform extract of C. deodara exhibited significant antioxidant potential mainly due to the presence of sesquiterpenes which may be responsible for various pharmacological activities of this plant.     

In vitro evaluation of the antioxidant and antimicrobial activity of DIMBOA [2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one]

The aim of this study was to evaluate the in vitro antioxidant and antimicrobial properties of the natural cyclic hydroxamic acid: 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA). Antioxidant activity of the isolated DIMBOA was examined using DPPH, FRAP and ABTS tests. It was found that DIMBOA exhibits a potent free-radical scavenging activity and a weaker iron (III) ions reducing activity. Antimicrobial activity against selected G(+), G(–) bacterial strains and against yeasts-like reference strains of fungi was investigated using disk-diffusion method. It has been shown that DIMBOA possess growth inhibitory properties against many strains of studied bacteria and fungi, such as Staphylococcus aureus, Escherichia coli as well as against Saccharomyces cerevisiae.     

Quantification of polyphenols with potential antioxidant properties in wines using reverse phase HPLC

A RP-HPLC method with photodiode array detection (DAD) was developed to separate, identify and quantify simultaneously the most representative phenolic compounds present in Madeira and Canary Islands wines. The optimized chromatographic method was carefully validated in terms of linearity, precision, accuracy and sensitivity. A high repeatability and a good stability of phenolics retention times (< 3%) were obtained, as well as relative peak area. Also high recoveries were achieved, over 80.3%. Polyphenols calibration curves showed a good linearity (r(2) >0.994) within test ranges. Detection limits ranged between 0.03 and 11.5 microg/mL for the different polyphenols. A good repeatability was obtained, with intra-day variations less than 7.9%. The described method was successfully applied to quantify several polyphenols in 26 samples of different kinds of wine (red, rosé and white wines) from Madeira and Canary Islands. Gallic acid was by far the most predominant acid. It represents more than 65% of all phenolics, followed by p-coumaric and caffeic acids. The major flavonoid found in Madeira wines was trans-resveratrol. In some wines, (-)-epicatechin was also found in highest amount. Canary wines were shown to be rich in gallic, caffeic and p-coumaric acids and quercetin.     

HPLC–DAD–MS identification of polyphenols from Passiflora leschenaultii and determination of their antioxidant,analgesic, anti-inflammatory and antipyretic properties

Passion fruit (Passiflora leschenaultii DC), an endemic species to peninsular India, is traditionally used to treat various ailments such as dysentery, urinary stone disease and wounds. The present study aimed to investigate the antioxidant, analgesic, anti-inflammatory, antipyretic activities and chemical composition of leaf extracts of P. leschenaultii. Bioactive secondary metabolites such as total phenolics, tannins and flavonoids were quantified. Antioxidant activities were determined by DPPH, ABTS⁺, FRAP, metal chelating and phosphomolybdenum assays. Hot plate, acetic acid and formalin induced pain models were used to evaluate the analgesic activity. In order to study the acute and chronic anti-inflammatory activities, carrageenan and cotton pellet induced models were used in rats. Brewer’s yeast induced pyrexia method was applied for the antipyretic test. Functional compounds from the plant were identified and quantified through HPLC–DAD–MS analysis. The obtained results revealed that the acetone extract of leaves exhibited higher phenolic (440.24 mg GAE/g extract) and flavonoid (253.33 mg RE/g extract) contents and scavenged the DPPH (IC₅₀ 29.14 μg/mL), ABTS⁺ (10509.69 μM TEAC/g extract) effectively. On investigating the analgesic, anti-inflammatory and antipyretic activities, the acetone extracts of leaves, at a dose of 400 mg/kg (p.o.) reduced significantly (p < 0.001) the pain, inflammation and fever responses in vivo. Bioactive compounds such as hyperin, chlorogenic acid, rutin and caffeic acids were identified in the leaves of P. leschenaultii employing HPLC–DAD–MS analysis. These findings illustrate the excellent potential of this species as valuable source of natural phytochemicals with pharmacological properties.     

Chemical composition and antioxidant activities of the essential oil from Nandina domestica fruits

The chemical composition and antioxidant activities of the essential oil from Nandina domestica fruits were studied for the first time. Twenty-two compounds, representing 82.79% of the oil, were identified from the oil. The major compounds were 3-hexen-1-ol (12.9%), linalool (12.3%), 2-methoxy-4-vinylphenol (9.9%), oleic acid (8.0%), furfural (5.8%) and 2,6-di-tert-butyl-4-methylphenol (5.7%). The antioxidant activities of the oil were evaluated using reducing power, metal chelating ability and scavenging capacity against 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azinobis-3-ethylbenzthiazoline-6-sulfonate (ABTS) and superoxide anion free radical. The oil exhibited significant antioxidant activities.     

Excelsanone,a new isoflavonoid from Erythrina excelsa (Fabaceae), with in vitro antioxidant and in vitro cytotoxic effects on prostate cancer cells lines

Abstract

A new isoflavonoid, excelsanone (2), was isolated from the ethyl acetate extract of Erythrina excelsa stem bark, together with three known compounds namely 6,8-diprenylgenistein (3), β-sitosterol (1) and sitosteryl-β-D-glucopyranoside (4). Their structures were elucidated using spectroscopic methods (HR-ESI-MS, NMR and IR) and by comparison with some literature data. The antioxidant activity of crude extracts and two isolated compounds was evaluated using free radical scavenging (DPPH) and Ferric Reducing Ability Power (FRAP) methods with catechin as standard. The results of the radical scavenging activity showed that excelsanone (2) has a moderate potential with an IC₅₀ of 1.31?mg/ml. The cytotoxicity of compounds 2 and 3 as well as the ethyl acetate extract was evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay in two prostate cancer cell lines (DU145 and PC3). Excelsanone (2) induced a greater cytotoxicity in all tested cell lines, with a significant inhibition of DU145 cells growth in a concentration-dependent manner.     

Metal-free multicomponent synthesis and in vitro antioxidant activity of indolylpyrazolopyrimidines

Multisubstituted indolylpyrazolopyrimidines were synthesized in good yields with base promoted one-pot multicomponent system from aldehyde, ketone, and indolylpyrazolamine. Milder and cost-effective conditions are the highlights of the present protocol. Among the synthesized compounds ( 4a-j ) 4b , 4c , 4e , and 4f have shown significant better in vitro antioxidant activity compared to standard ascorbic acid.     

Chemical constituents,anticancer, antimicrobial and antioxidant activities of essential oil from Anaphalis lacteal grown in Qinghai-Tibet Plateau

The chemical constituent of the essential oil from Anaphalis lacteal was determined; 31 compounds, representing 93.91% of the total oil, were identified by gas chromatography–mass spectrometry analysis. Three Gram-positive bacteria species, three Gram-negative bacteria species and four fungi were used to determine antimicrobial activity; the results revealed that the essential oil had a remarkable antimicrobial effect against bacteria and a susceptive effect against fungus. The oil also possessed more efficient free-radical scavenging activities than butylated hydroxytoluene (BHT) with 50% inhibitory concentration (IC₅₀) value 31 μg/mL (40 μg/mL for BHT). MTT assay illustrated that the oil expressed certain effect in inhibiting the growth of HeLa and Hep-6 cancer cells.     

Identification and in vitro antioxidant activities of phenolic compounds isolated from Cynoglossum cheirifolium L.

In an extensive search for bioactive compounds from plant sources, the quantitative and qualitative characterisation of the compounds present in Cynoglossum cheirifolium extracts was studied. Total phenolic and flavonoid contents were determined by spectrophotometric techniques. In vitro antioxidant and radical scavenging profiling was determined through DPPH^? scavenging activity and Ferric reducing antioxidant power (FRAP). Our study showed that leaves produce more phenolic compounds, followed by flowering aerial part. The butanolic fraction obtained from leaves extract exhibited the highest total phenolics (78.65 ± 3.58 mg GAE/g DW) and flavonoids (22.15 ± 4.66 mg CE/g DW). In contrast, this fraction displayed the highest DPPH^? scavenging ability with IC₅₀ values of 0.06 ± 0.003 mg/mL. The RP-HPLC-PDA analysis of phenolic compounds from leaves of C. cheirifolium lets to identify: rosmarinic acid, ferulic acid, caffeic acid, p-coumaric acid, syringic acid, sinapic acid and rutin. The obtained results indicate that this plant represent a valuable source of natural antioxidants.