Phenolic constituents and antioxidant activity of Wendita calysina leaves (Burrito), a folk Paraguayan tea.
Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, Via Ponte don Melillo, 84084 Fisciano (SA), Italy.
Burrito tea originates from the leaves of Wendita calysina, an indigenous Paraguayan plant, which is commonly consumed in South America and in Western countries. Phytochemical investigation of this species has led to the isolation of 14 constituents, among them 2 new flavanonols, dihydroquercetagetin (1) and 3,5,6,7,4'-pentahydroxyflavanonol (2), in addition to several known methoxyflavones, methoxyflavonols, phenylethanoid glycosides, and benzoic acid derivatives (4-14). All structures were elucidated by ESI-MS and NMR spectroscopic methods. Quantitative determination of phenolic constituents from burrito water infusions has been performed by HPLC-UV-DAD. The total antioxidant activity of the tea was measured by the ABTS(*)(+) radical cation decolorization and chemiluminescence (CL) assays and compared with the values of other commonly used herbal teas (green and black teas, mate, and rooibos).
Anal Chem Insights. 2012 ;7 :1-12 22493561
Holistic Control of Herbal Teas and Tinctures Based on Sage (Salvia officinalis L.) for Compounds with Beneficial and Adverse Effects using NMR Spectroscopy.
Department for Public Health and Health Technology Assessment, University for Health Sciences, Medical Informatics and Technology, Eduard Wallnöfer-Zentrum 1, A-6060 Hall in Tyrol, Austria.
A methodology that utilizes (1)H-NMR spectroscopy has been developed to simultaneously analyze toxic terpenes (thujone and camphor), major polyphenolic compounds, the total antioxidant capacity (ORAC) and the Folin-Ciocalteu (FC) index in foods and medicines containing sage. The quantitative determination of rosmarinic acid (limit of detection (LOD)= 10 mg/L) and total thujone (LOD = 0.35 mg/L) was possible using direct integration of the signals. For other parameters (derivatives of rosmarinic acid, carnosol and flavone glycosides, ORAC and FC index), chemometric regression models obtained separately for alcohol-based tinctures (R(2)= 0.94-0.98) and aqueous tea infusions (R(2)= 0.79-0.99) were suitable for screening analysis. The relative standard deviations for authentic samples were below 10%. The developed methodology was applied for the analysis of a wide variety of sage products (n = 108). The total thujone content in aqueous tea infusions was found to be in the range of not detectable (nd) to 37.5 mg/L (average 9.2 mg/L), while tinctures contained higher levels (range nd-409 mg/L, average 107 mg/L). The camphor content varied from 2.1 to 43.7 mg/L in aqueous infusions and from not detectable to 748 mg/L in tinctures (averages were 14.1 and 206 mg/L, respectively). Phenolic compounds were also detected in the majority of the investigated products.(1)H-NMR spectroscopy was proven to have the ability to holistically control all important adverse and beneficial compounds in sage products in a single experiment, considerably saving time, resources and costs as NMR replaces four separate methodologies that were previously needed to analyze the same parameters.
J Med Food. 2011 May ;14 (5):517-27 21434775
Fatima Abderrahim, Seyer Estrella, Cristina Susín, Silvia M Arribas, M Carmen González, Luis Condezo-Hoyos
Department of Physiology, Faculty of Medicine, Autonomous University of Madrid, Madrid, Spain.
Because of its good sensorial attributes, lemon verbena is used as a primary ingredient in infusions and nonalcoholic drinks. The present study was designed to assess the antioxidant activity (AA) of lemon verbena infusion (LVI) as well as the thermal stability of its AA and the content of polyphenolic compounds. The values reflecting the AA of LVI, including AA index, fast scavenging rate against 2,2-diphenyl-1-picrylhydrazyl, Trolox equivalent antioxidant capacity, and hydroxyl radical scavenging, are higher than those of many herbal infusions and antioxidant drinks estimated from reported data. In addition, the slope lag time and specific oxyradical antioxidant capacity values of LVI are comparable to those of a commercial antioxidant drink based on green tea. Hence, LVI is a source of bifunctional antioxidants, and thus in vivo studies of the antioxidant capacity of LVI would be useful to evaluate its potential as an ingredient in antioxidant drinks.
Effects of phenolic compounds of fermented thai indigenous plants on oxidative stress in streptozotocin-induced diabetic rats.
Chaiyavat Chaiyasut, Winthana Kusirisin, Narissara Lailerd, Peerasak Lerttrakarnnon, Maitree Suttajit, Somdet Srichairatanakool
Department of Pharmaceutical Science, Faculty of Pharmacy, Chiang Mai University, Chiang Mai 50200, Thailand.
We investigated the effects of antioxidant activity of fermentation product (FP) of five Thai indigenous products on oxidative stress in Wistar rats with streptozotocin (STZ)-induced diabetes type II. The rats were fed with placebo and with the FP (2 and 6 mL/kg body weight/day) for 6 weeks. Rutin, pyrogallol and gallic acid were main compounds found in the FP. Plasma glucose levels in diabetic rats receiving the higher dose of the FP increased less when compared to the diabetic control group as well as the group receiving the lower FP dose (13.1%, 29%, and 21.1%), respectively. A significant dose-dependent decrease in plasma levels of thiobarbituric acid reactive substance (P <.05) was observed. In addition, the doses of 2 and 6 mL FP/kg/day decreased the levels of erythrocyte ROS in diabetic rats during the experiment, but no difference was observed when compared to the untreated diabetic rat group. Results imply that FP decreased the diabetes-associated oxidative stress to a large extent through the inhibition of lipid peroxidation. The FP also improved the abnormal glucose metabolism slightly but the difference was not statistically significant. Thus, FP may be a potential therapeutic agent by reducing injury caused by oxidative stress associated with diabetes.
Hypotriacylglycerolemic and antiobesity properties of a new fermented tea product obtained by tea-rolling processing of third-crop green tea (Camellia sinensis) leaves and loquat (Eriobotrya japonica) leaves.
Kazunari Tanaka, Shizuka Tamaru, Shoko Nishizono, Yuji Miyata, Kei Tamaya, Toshiro Matsui, Takashi Tanaka, Yoshie Echizen, Ikuo Ikeda
Graduate School of Human Health Science, University of Nagasaki, Nagayo-cho, Nishisonogi-gun, Nagasaki, Japan. firstname.lastname@example.org
We manufactured a new fermented tea by tea-rolling processing of third-crop green tea (Camellia sinensis) leaves and loquat (Eriobotrya japonica) leaves. The mixed fermented tea extract inhibited pancreatic lipase activity in vitro, and effectively suppressed postprandial hypertriacylglycerolemia in rats. Rats fed a diet containing 1% freeze-dried fermented tea extract for 4 weeks had a significantly lower liver triacylglycerol concentration and white adipose tissue weight than those fed the control diet lacking fermented tea extract. The activity of fatty acid synthase in hepatic cytosol markedly decreased in the fermented tea extract group as compared to the control group. The serum and liver triacylglycerol- and body fat-lowering effects of the mixed fermented tea extract were strong relative to the level of dietary supplementation. These results suggest that the new fermented tea product exhibited hypotriacylglycerolemic and antiobesity properties through suppression of both liver fatty acid synthesis and postprandial hypertriacylglycerolemia by inhibition of pancreatic lipase.
Department of Environmental Toxicology, University of California, Davis, CA 95616, USA.
Recently, research on natural antioxidants has become increasingly active in various fields. Accordingly, numerous articles on natural antioxidants, including polyphenols, flavonoids, vitamins, and volatile chemicals, have been published. Assays developed to evaluate the antioxidant activity of plants and food constituents vary. Therefore, to investigate the antioxidant activity of chemical(s), choosing an adequate assay based on the chemical(s) of interest is critical. There are two general types of assays widely used for different antioxidant studies. One is an assay associated with lipid peroxidations, including the thiobarbituric acid assay (TBA), malonaldehyde/high-performance liquid chromatography (MA/HPLC) assay, malonaldehyde/gas chromatography (MA/GC) assay, beta-carotene bleaching assay, and conjugated diene assay. Other assays are associated with electron or radical scavenging, including the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid)(ABTS) assay, ferric reducing/antioxidant power (FRAP) assay, ferrous oxidation-xylenol orange (FOX) assay, ferric thiocyanate (FTC) assay, and aldehyde/carboxylic acid (ACA) assay. In this review, assays used recently were selected for extended discussion, including discussion of the mechanisms underlying each assay and its application to various plants and foods.
Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
Three new phenolic compounds named whiskey tannins A and B and carboxyl ellagic acid were isolated from commercial Japanese whiskey, along with gallic acid, ellagic acid, brevifolin carboxylic acid, three galloyl glucoses, a galloyl ester of phenolic glucoside, 2,3-(S)-hexahydroxydiphenoylglucose, and castacrenin B. Whiskey tannins A and B were oxidation products of a major oak wood ellagitannin, castalagin, in which the pyrogallol ring at the glucose C-1 position of castalagin was oxidized to a cyclopentenone moiety. These tannins originated from ellagitannins contained in the oak wood used for barrel production; however, the original oak wood ellagitannins were not detected in the whiskey. To examine whether the whiskey tannins were produced during the charring process of barrel production, pyrolysis products of castalagin were investigated. Dehydrocastalagin and a new phenolcarboxylic acid trislactone having an isocoumarin structure were isolated, along with castacrenin F and ellagic acid. However, whiskey tannins were not detected in the products.
Post-Harvest and Wine Technology Division, ARC Infruitec-Nietvoorbij, Private Bag X5026, Stellenbosch 7599, South Africa. joubertL@arc.agric.za
Rooibos (Aspalathus linearis (Brum.f) Dahlg.) and honeybush (Cyclopia Vent. species) are popular indigenous South African herbal teas enjoyed for their taste and aroma. Traditional medicinal uses of rooibos in South Africa include alleviation of infantile colic, allergies, asthma and dermatological problems, while a decoction of honeybush was used as a restorative and as an expectorant in chronic catarrh and pulmonary tuberculosis. Traditional medicinal uses of Athrixia phylicoides DC., or bush tea, another indigenous South African plant with very limited localised use as herbal tea, include treatment of boils, acne, infected wounds and infected throats. Currently rooibos and honeybush are produced for the herbal tea market, while bush tea has potential for commercialisation. A summary of the historical and modern uses, botany, distribution, industry and chemical composition of these herbal teas is presented. A comprehensive discussion of in vitro, ex vivo and in vivo biological properties, required to expand their applications as nutraceutical and cosmeceutical products, is included, with the main emphasis on rooibos. Future research needs include more comprehensive chemical characterisation of extracts, identification of marker compounds for extract standardisation and quality control, bioavailability and identification of bio-markers of dietary exposure, investigation of possible herb-drug interactions and plant improvement with regards to composition and bioactivity.
Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo Machi, Nagasaki 852-8521, Japan.
Lipase and amylase inhibitory activities of black tea were examined. After solvent partitioning of a black tea extract with the ethyl acetate and n-butanol, the two soluble fractions showed comparable inhibitory activities. Activity in the ethyl acetate fraction was mainly attributable to polyphenols with low-molecular weights, such as theaflavin gallates. On the other hand, the active substance in the n-butanol layer was ascertained to be a polymer-like substance. 1H- and 13C-NMR spectra showed signals arising from the flavan A-ring and galloyl groups, although signals due to flavan B-rings were not detected, suggesting that the polymer-like substances were generated by oxidative condensation of flavan B-rings, a result which was previously deduced from our results of in vitro catechin oxidation experiments. Enzymatic oxidation of epicatechin 3-O-gallate produced a similar polymer-like substance and suggested that condensation between a B-ring and galloyl groups was involved in the polymerization reaction.
Inhibition of inducible nitric oxide synthase in vitro and in vivo by a water-soluble extract of Wendita calysina leaves.
Stefania Marzocco, Anna Lisa Piccinelli, Luca Rastrelli, Emanuela Mazzon, Salvatore Cuzzocrea, Giuseppina Autore
Department of Pharmaceutical Sciences, School of Pharmacy, University of Salerno, Via Ponte don Melillo, 84084 Fisciano, Italy. email@example.com
Wendita calysina is a Paraguayan herbaceous plant commonly known as burrito. Our previous study indicated that burrito leaves are a very good source of phenylpropanoid glycosides, principally verbascoside. From W. calysina leaves, a standardized, water-soluble extract (WSE) rich in phenylpropanoid glycosides has been developed on an industrial scale to be used as a food supplement, cosmetic, phytomedicine, and ingredient of different formulations. In this study, we investigated the effect of the W. calysina WSE both in vitro in murine macrophage cell line J774.A1 stimulated with lipopolysaccharide (LPS) and, in vivo in an animal model of acute inflammation, carrageenan-induced pleurisy. Here we report that W. calysina WSE (0.05, 0.1, and 0.5 mg/ml) inhibited inducible nitric oxide synthase (iNOS) expression and activity in LPS-stimulated J774.A1. In vivo experiments showed that injection of carrageenan (2%) into the pleural cavity of rats elicited an acute inflammatory response characterized by iNOS expression, intercellular adhesion molecule-1 (ICAM-1) up-regulation, nitrotyrosine and poly (ADP-ribose) synthase (PARS) formation, and lung tissue damage-all parameters significantly reduced by W. calysina WSE (500 mg/kg per os). These results report, for the first time, that a treatment with W. calysina WSE exerts anti-inflammatory effects both in vitro and in vivo.
Other papers by authors:
Anna Lisa Piccinelli, Mercedes Campo Fernandez, Osmany Cuesta-Rubio, Ingrid Márquez Hernández, Francesco De Simone, Luca Rastrelli
Dipartimento di Scienze Farmaceutiche, Università di Salerno, Via Ponte Don Melillo, 84084 Fisciano, Salerno, Italy, and Instituto de Farmacia y Alimentos (IFAL), Universidad de La Habana, Avenida 23, 21425 Lisa, La Habana, Cuba CP. 13600.
Chemical investigation of a red-type Cuban propolis sample has led to the isolation of 11 isoflavonoids (2 isoflavones, 3 isoflavans, and 6 pterocarpans), together with gallic acid, isoliquiritigenin, and (-)-liquiritigenin. Structural determination, including the absolute stereochemistry, was accomplished by spectroscopic analysis, particularly CD and 2D NMR techniques. The fragmentation behavior of pterocarpans was studied by electrospray ionization (ESI) tandem mass spectrometry (MS/MS) using an ion-trap analyzer, and a generalized fragmentation pathway, useful in the identification and structural characterization of pterocarpans, is proposed. Isoflavonoids are reported for the first time from propolis samples.
Daylin Gamiotea-Turro, Osmany Cuesta-Rubio, Sylvia Prieto-González, Francesco De Simone, Siro Passi, Luca Rastrelli
Center of Pharmaceutical Chemistry (CQF), 200 & 21, Atabey, Playa, PO Box 16042, Apartado 6990, La Habana, Cuba.
Two new compounds have been isolated from the leaves of Hypericum styphelioides. Their structures have been established on the basis of mass spectrometry and 2D NMR techniques as 1,3,5-trihydroxy-2-(2',2'-dimethyl-4'-isopropenyl)cyclopentanylxanthone (1) and 3,5-dihydroxybenzophenon-4-beta-d-glucoside (2). Known compounds 5-O-demethylpaxanthonin (3) and 3-geranyl-1-(3-methylbutanoyl)phloroglucinol (4) were also isolated and characterized. Compounds 1-4 were evaluated for their antioxidative properties in Trolox equivalent antioxidant activity (TEAC) and chemiluminescence (CL) assays.
Fatty acid pattern, oxidation product development, and antioxidant loss in muscle tissue of rainbow trout and Dicentrarchus labrax during growth.
Istituto Dermopatico dell'Immacolata (IDI, IRCCS), Via Monti di Creta, 104, Roma, Italy.
The levels of hydrophilic, lipophilic, and enzymatic antioxidants, the oxidative damage to lipids and proteins, and the fatty acid patterns of triglyceride and phospholipid fractions were assayed in fresh muscle tissue of rainbow trouts (Oncorhynchus mykiss) and sea basses (Dicentrarchus labrax) during aging, to investigate the correlation between oxidative stress and aging processes in fish. The present studies suggests that lipid peroxidation and accumulation of oxidized proteins during in vivo aging are most likely to be linked with an age-dependent decline of lipophilic antioxidants (CoQH(2), CoQ, and vitamin E) and vitamin C contents in muscle tissue, whereas fish aging is not linked to a decline in antioxidant enzymes and reduced glutathione levels. Lipophilic antioxidant and vitamin C levels represent a reliable marker of oxidative stress during aging, and their determination might be useful for the assessment of fish age.
Fatty acid composition and antioxidant levels in muscle tissue of different Mediterranean marine species of fish and shellfish.
Istituto Dermopatico dell'Immacolata (IDI, IRCCS), Via Monti di Creta, 104, Roma, Italy.
The levels of hydrophilic, lipophilic, and enzymatic antioxidants, as well as the fatty acids composition, of triglyceride and phospholipid fractions were determined in the muscle tissue of 21 species of teleosts, 3 species of cephalopods, and 6 species of crustaceans, just caught from the central Tyrrhenian Sea (Mediterranean Sea). The enzymatic activities and the levels of low-molecular-weight antioxidants, and the percentages of fatty acids, showed marked interspecies differences. Our results showed that total polyunsaturated fatty acids (21.7-61.5%) were the highest, followed by saturated (16.9-41.3%) and monounsaturated (9.1-42.8%) fatty acids. The total n-3 fatty acids content (16.6-57.1%) was found to be higher than the total n-6 fatty acids content (4.1-10.6%). All of the species studied had an n-3/n-6 ratio of more than 1, confirming the great importance of fish and shellfish as a significant dietary source of n-3 polyunsaturated fatty acids and their beneficial role in the Mediterranean type of diet.
Rate of degradation of alpha-tocopherol, squalene, phenolics, and polyunsaturated fatty acids in olive oil during different storage conditions.
Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, Via Ponte don Melillo, 84084 Fisciano (SA), Italy. firstname.lastname@example.org
Changes in the concentration of tocopherol, monophenols, o-diphenols, squalene, and polyunsaturated fatty acids in olive oil were evaluated during 1 year at various storage conditions. Samples of two different extra virgin olive oil (EOO), produced in Calabria (Italy), were stored in dark and in colorless bottles, filled up completely or to half, in order to simulate the domestic storage conditions. The extent of oxidation or photooxidation was monitored by periodic measurements of peroxide values and the rate of degradation of alpha-tocopherol, o-diphenols, squalene, and polyunsaturated fatty acids. The quantitative analysis of the constituents has been performed by HPLC-DAD, HPLC-MS, and GC-MS. The main changes in the concentrations of the analyzed compounds were associated with the major oxygen level in the half-empty glass bottles. alpha-Tocopherol was the first molecule to be oxidized (-20% after 2 months,-92% after 12 months). Squalene and o-diphenols were protected in the first months by the presence of alpha-tocopherol, and their content decreased significantly only after 6 and 8 months, respectively, in the half-empty bottles. The concentration of polyunsaturated fatty acids remained almost constant during 8 months for all four different storage conditions; their oxidation started when the level of the antioxidants decreased.
J Agric Food Chem. 2012 Dec 2;: 23199374
DEVELOPMENT AND VALIDATION OF METHOD FOR DETERMINATION OF (E)-RESVERATROL AND RELATED PHENOLIC COMPOUNDS IN BEVERAGES USING MOLECULARLY IMPRINTED PHASE EXTRACTION.
A molecularly imprinted polymer was prepared using E-resveratrol as template and was evaluated for multi-component multi-class analysis of polyphenolic compounds in complex matrices such as natural and alcoholic beverages. Chromatographic evaluation of the polymer exhibited high selectivity for E-resveratrol and its structural analogues as quercetin and other flavonoids. An analytical procedure based on Molecularly imprinted solid phase extraction (MISPE) and high performance liquid chromatography coupled to UV detector was developed and validated for determination of (E)-resveratrol and quercetin in wine and fruit juice samples. Specific binding capacity of the MIP was estimated as 80 μg g-1 polymer by the cartridge test. MISPE sample pretreatment allows an excellent sample clean up enormously decreasing the number of co-extracted potentially interfering compounds. Under the described conditions, by extracting 2 mL samples a clean extract is obtained and E-resveratrol and quercetin could be easily identified at concentration levels of respectively 1.5 and 7.0 μg L-1 level. Keywords: molecularly imprinted polymer, solid phase extraction, flavonoids, resveratrol, quercetin, wine, red fruits juice, lingonberry.
pH-controlled dispersive liquid-liquid microextraction for the analysis of ionisable compounds in complex matrices: Case study of ochratoxin A in cereals.
Dipartimento di Scienze Farmaceutiche e Biomediche, Università degli Studi di Salerno, via Ponte Don Melillo, 84084 Fisciano (SA), Italy.
A new sample preparation procedure, termed pH-controlled dispersive liquid-liquid microextraction (pH-DLLME), has been developed for the analysis of ionisable compounds in highly complex matrices. This DLLME mode, intended to improve the selectivity and to expand the application range of DLLME, is based on two successive DLLMEs conducted at opposite pH values. pH-DLLME was applied to determination of ochratoxin A (OTA) in cereals. The hydrophobic matrix interferences in the raw methanol extract (disperser, 1mL) were removed by a first DLLME (I DLLME) performed at pH 8 to reduce the solubility of OTA in the extractant (CCl(4), 400μL). The pH of the aqueous phase was then adjusted to 2, and the analyte was extracted and concentrated by a second DLLME (extractant, 150μL C(2)H(4)Br(2)). The main factors influencing the efficiency of pH-DLLME including type and volume of I DLLME extractant, as well as the parameters affecting the OTA extraction by II DLLME, were studied in detail. Under optimum conditions, the method has detection and quantification limits of 0.019 and 0.062μgkg(-1), respectively, with OTA recoveries in the range of 81.2-90.1%(n=3). The accuracy of the analytical procedure, evaluated with a reference material (cereal naturally contaminated with OTA), is acceptable (accuracy of 85.6%±1.7, n=5). The applicability of pH-DLLME to the selective extraction of other ionisable compounds, such as acidic and basic pharmaceutical products was also demonstrated. The additional advantages of pH-DLLME are a higher selectivity and the extension of this microextraction technique to highly complex matrices.
J Agric Food Chem. 2012 Sep 10;: 22957519
HPLC-PDA-MS and NMR Characterization of a Hydroalcoholic Extract of Citrus aurantium L. var. amara peel with Antiedematogenic Activity.
Teresa Mencherini, Luca Campone, Anna Lisa Piccinelli, Milagros Garcia Mesa, Dulce Maria Armenteros, Rita Aquino, Luca Rastrelli
The phytochemical profile of a hydroalcoholic extract of Citrus aurantium var. amara L. peel, used in Cuba as herbal medicine, was characterized by HPLC-PDA-MS. Two di-C-glycosyl flavones (vincenin II and diosmetin 6,8-di-C-glucoside), a series of flavone (luteolin 7-O-neohesperidoside, rhoifolin and neodiosmin) and flavanone (neoeriocitrin, naringin and neohesperidin) 7-O-neohesperidosides and two methoxyflavones (nobiletin and tangeretin), commonly present in Citrus, were identified. Furthermore, brutieridin and melitidin, two 3-hydroxy-3-methylglutaryl flavanone glycosides were also characterized along with rhoifolin 4'-glucoside and three coumarins (8-3'-β-D-glucopyranosyloxy-2'-hydroxy-3'-methylbutyl-7-methoxycoumarin, merazin hydrate and isomerazin). A preparative isolation procedure followed by NMR spectroscopy confirmed the proposed structures of the major flavonoids and identified the coumarins. The phenolic content was found to be 14.8 mg mL-1, and naringin and neohesperidin were the compounds present in the highest concentration'(3.6 and 2.6 mg mL-1). The extract of C. aurantium peel inhibited significantly (p<0.05) both the histamine and dextran-induced edema in rats in a concentration-dependent manner (IC50 = 119.6 and 118.3 mg Kg-1, respectively), providing evidence for the therapeutic use of C. aurantium var. amara peel.
Lianet Monzote Fidalgo, Idalia Sariego Ramos, Marley García Parra, Osmany Cuesta-Rubio, Ingrid Márquez Hernández, Mercedes Campo Fernández, Anna Lisa Piccinelli, Luca Rastrelli
Parasitology Department, Institute of Tropical Medicine "Pedro Kouri", Havana City, Cuba. email@example.com
In this paper we analyzed the antiprotozoal effects of eighteen Cuban propolis extracts (brown, red and yellow type) collected in different geographic areas, using Leishmania amazonensis (as a model of intracellular protozoa) and Trichomonas vaginalis (as a model of extracellular protozoa). All evaluated propolis extracts caused inhibitory effect on intracellular amastigotes of L. amazonensis. However, cytotoxicity on peritoneal macrophages from BALB/c mice was observed. Only five samples decreased the viability of T. vaginalis trophozoites at concentrations lower than 10 microg/mL. No correlation between the type of propolis and antiprotozoal activity was found. Cuban propolis extracts demonstrated activity against both intracellular and extracellular protozoa model, as well as the potentialities of propolis as a natural source to obtain new antiprotozoal agents.
Departamento de Control Químico, Facultad de Farmacia, Universidad Nacional Autonoma - Tegucigalpa, Honduras. firstname.lastname@example.org
A new phenolic derivative, 4-methoxyphenol 1-O-beta-D-apiofuranosyl-(1 --> 6)-O-beta-D-glucopyranoside (1), has been identified together with uncommon 3,4-dimethoxyphenol 1-O-beta-D-apiofuranosyl-(1 --> 6)-O-beta-D-glucopyranoside (2) and 3-hydroxy, 4-methoxyphenol 1-O-beta-D-apiofuranosyl-(1 --> 6)-O-beta-D-glucopyranoside (3) from the leaves of Martinella obovata (Kunth) Bureau & K. Schum., an Honduran species used in folk medicine for the treatment of eyes diseases. Verbascoside, isoverbascoside, leucoceptoside A, vitexin, isovitexin, luteolin 8-C-beta-D-glucopiranoside and spireoside were also found. All structures were elucidated on the basis of mass spectrometry and 2D NMR techniques.
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Planta Med. 2012 May ;78 (7):703-10 22322398
Adriana Passos Oliveira, Melanie Raith, Ricardo Machado Kuster, Leandro Machado Rocha, Matthias Hamburger, Olivier Potterat
Division of Pharmaceutical Biology, University of Basel, Klingelbergstrasse 50, Basel, Switzerland.
Sideroxylon obtusifolium (Roem.& Schult.) T. D. Penn.(family Sapotaceae) is a tree native to Central and South America. Infusions of the bark and the leaves are used in Brazilian folk medicine as an anti-inflammatory remedy. However, information on the constituents of S. obtusifolium remains scarce, and only common pentacyclic triterpenoids have been previously reported. HPLC-DAD/MS analyses revealed that saponins and flavonoids were the main constituents of the leaves. From the butanol-soluble fraction of an ethanolic extract, a total of four saponins and ten flavonol glycosides were isolated by a combination of chromatographic methods including Sephadex LH-20, MPLC, and HPLC. Their structures were established by acid hydrolysis and spectroscopic methods, mainly MS (n), 1D and 2D NMR experiments. The compounds include the new triterpene glycoside 3-O-( β-D-glucopyranosyl)-protobassic acid 28-O- β-D-apiofuranosyl-(1 → 3)-O-[O- β-D-apiofuranosyl-(1 → 3)- β-D-xylopyranosyl-(1 → 4)]-O- α-L-rhamnopyranosyl-(1 → 2)- α-L-arabinopyranosyl ester ( 1), as well as the new flavonol glycosides, quercetin-3-O-(O- α-L-rhamnopyranosyl-(1→ 2)-O-[ β-D-glucopyranosyl-(1 → 3)]- β-D-galactopyranoside)( 6) and kaempferol-3-O-(O- α-L-rhamnopyranosyl-(1 → 2)-O-[ β-D-glucopyranosyl-(1 → 3)]- β-D-galactopyranoside)( 8). In addition, catechin and a glycerogalactolipid, gingerglycolipid A, were obtained from the ethyl acetate-soluble fraction. The isolated compounds could be used in the future as chemical markers for quality control of this herbal drug.
Comparative study of the effect of green and roasted water extracts of mate (Ilex paraguariensis) on glucosyltransferase activity of Streptococcus mutans.
Jim Battagim, Verônica Trícoli de Souza, Natália Reiko Sato Miyasaka, Ildenize Barbosa da Silva Cunha, Alexandra Christine Sawaya, Anna Maria Alves de Piloto Fernandes, Marcos Nogueira Eberlin, Marcelo Lima Ribeiro, Patrícia de Oliveira Carvalho
São Francisco University (USF), Bragança Paulista, SP , Brazil.
Glucosyltransferase (GTF) plays an important role in the development of dental caries. This study was carried out to compare the efficiency of green mate (GM) and roasted mate (RM) water extracts, drinks rich in polyphenolic compounds consumed in the subtropical region of South America, on the extracellular GTF activity from Streptococcus mutans. The RM extract exhibited a greater inhibitory effect (IC₅₀ of 10 mg/mL) despite presenting lower polyphenolic content. The kinetic analysis showed that there were significant differences (P < 0.05) between the extracts with respect to the values for K(m) and K(i), whereas the values for V(max) were the same, implying the competitive nature of GTF inhibition. GTF activity was also measured using selected polyphenols as inhibitors, and the most effective inhibitors were rutin and caffeoylshikimic acid. The characterization of the extracts by ESI-MS and UPLC-MS showed that the compounds formed during roasting, possibly shikimic acid derivatives and other unindentified compounds formed by the Maillard reaction, appeared to contribute to the inhibition of GTF activity.
BMC Biochem. 2011 ;12 :16 21510884
The inhibition of the mammalian DNA methyltransferase 3a (Dnmt3a) by dietary black tea and coffee polyphenols.
Chemistry, Jacobs University Bremen, Campus Ring 1, 28759 Bremen, Germany.
Black tea is, second only to water, the most consumed beverage globally. Previously, the inhibition of DNA methyltransferase 1 was shown by dietary polyphenols and epi-gallocatechin gallate (EGCG), the main polyphenolic constituent of green tea, and 5-caffeoyl quinic acid, the main phenolic constituent of the green coffee bean. We studied the inhibition of DNA methyltransferase 3a by a series of dietary polyphenols from black tea such as theaflavins and thearubigins and chlorogenic acid derivatives from coffee. For theaflavin 3,3 digallate and thearubigins IC50 values in the lower micro molar range were observed, which when compared to pharmacokinetic data available, suggest an effect of physiological relevance. Since Dnnmt3a has been associated with development, cancer and brain function, these data suggest a biochemical mechanism for the beneficial health effect of black tea and coffee and a possible molecular mechanism for the improvement of brain performance and mental health by dietary polyphenols.
Phytochem Anal. 2011 Mar 17;: 21413094
Identification of 2″-Galloylated Flavonol 3-O-Glycosides Accumulating in Developing Leaves of Persimmon.
Department of Food Science, Niigata University of Pharmacy and Applied Life Sciences, 265-1 Higashijima, Akiha-ku, Niigata, 956-8603, Japan.
Introduction - Dried leaves of persimmon, traditionally consumed as a herbal tea in Japan, contain bioactive galloylated flavonol glycosides. Investigation of the seasonal compositional changes in these compounds is important for determining the optimum harvest time. Objective - The three objectives were:(1) to elucidate the compositional changes of the flavonol glycosides in persimmon leaves collected in different seasons;(2) to develop an efficient method for separation of the constituents; and (3) to compare their antioxidant activities. Methodology - Fresh persimmon leaves were collected at different growth stages in 2007 and 2008 in Niigata, Japan. Total flavonols were extracted with 70% aqueous acetone followed by ethyl acetate partitioning, and were analysed by high-performance liquid chromatography. Enzymatic transformation and chromatographic fractionation was performed to isolate the individual flavonols. Two antioxidant assays were performed. Results - Four nongalloylated flavonol glycosides were detected at the leaf-shooting stage, and four additional galloylated flavonol glycosides accumulated during leaf development, resulting in a total of eight constituents. Isolation of nongalloylated and galloylated constituents was successfully achieved through enzymatic transformation of the flavonol mixture using combinations of tannase, β-glucosidase and β-galactosidase, followed by chromatographic fractionation. The gallates were identified as regiospecific 2″-galloylated galactosides and glucosides of kaempferol and quercetin. A mixture of 2″-galloylated flavonol glycosides had a two-fold stronger antioxidant activity than the nongalloylated mixture. Conclusion - This study showed that four 2″-galloylated flavonol glycosides had accumulated in developing leaves of persimmon by the end of May through a rapid 2″-galloylation of the corresponding nongalloylated flavonol glycosides. Copyright © 2011 John Wiley & Sons, Ltd.
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, China.
Camellia pachyandra Hu. is a species in Camellia sect. Heterogenea (Theaceae), whose leaves have been used for making tea and consumed by the local people living in Yunnan province, China. This is the first investigation of the chemical constituents in the leaves of C. pachyandra, from which 22 phenolic compounds including nine hydrolyzable tannins (1-9), 11 flavonol glycosides (10-20), and two simple phenolics (21, 22) were isolated. It was noted that the leaves of the title plant contained no caffeine and no catechin, whereas hydrolyzable tannins were found to be the major constituents, of which the content of ellagitannin 5 reached to 3.7%. All the isolates were evaluated for their antioxidant activities by DPPH radical scavenging and tyrosinase inhibitory assays. Though the secondary metabolites without caffeine and catechins are different from the commonly consumed tea plants, the results suggested that the leaves of C. pachyandra, rich in hydrolyzable tannins as potent antioxidants, could be developed as an ideal resource for a natural beverage without caffeine.
Department of Pharmaceutical Sciences, Dr. Hari Singh Gour University, Sagar (M.P.) 470003, India. email@example.com
Curculigo orchioides Gaertn.(family Amaryllidaceae) is an endangered rasayana herb which is popularly known as "Kali Musli". The plant is native to India, and holds a special position as a potent adaptogen and aphrodisiac in Ayurvedic system of medicine. It is an important ingredient of many Ayurvedic preparations and is considered to have aphrodisiac, immunostimulant, hepatoprotective, antioxidant, anticancer and antidiabetic activities. Various chemical constituents like mucilage, phenolic glycosides, saponins and aliphatic compounds from the plant have been reported. The plant is also considered as an important component of various herbal preparations of the Chinese and Kampo medicine. The present review is an attempt to enumerate various biologically tested activities and evaluation of different phytochemicals present in this important medicinal plant.
Planta Med. 2010 Oct ;76 (15):1746-8 20379958
College of Basic Medical Sciences, Department of Biochemistry and Molecular Biology, Second Military Medical University, Shanghai, P. R. China.
Three new iridoid glycosides, epiasperuloside (1), epipaederosidic acid (2), and epipaederoside (3), together with 7 known compounds, were isolated from the 85% ethanol extract of the leaves of Saprosma ternatum Hook. f. Their structures were determined by application of spectroscopic (NMR, MS) and chemical methodologies. The antioxidant activity was evaluated for all isolates in terms of both DPPH and ABTS bioassays. Epiasperuloside (1) showed some antioxidant activity.
Department of Chemistry, Kohat University of Science and Technology, Kohat 26000, NWFP, Pakistan. firstname.lastname@example.org
Phytochemical investigations on the n-BuOH-soluble fraction of the whole plant of Buddleja davidii led to the isolation of the phenylpropanoid glycosides 1-10. Their structures were determined by 1D and 2D NMR spectroscopic techniques. All the compounds showed potent antioxidative activity in three different tests, with IC(50) values in the range 4.15-9.47 microM in the hydroxyl radical ( OH) inhibitory activity test, 40.32-81.15 microM in the total ROS (reactive oxygen species) inhibitory activity test, and 2.26-7.79 microM in the peroxynitrite (ONOO(-)) scavenging activity test. Calceolarioside A (1) displayed the strongest scavenging potential with IC(50) values of (4.15 +/- 0.07, 40.32 +/- 0.09, 2.26 +/- 0.03 microM) for OH, total ROS and scavenging of ONOO(-), respectively.
Hasan Kirmizibekmez, Carla Bassarello, Sonia Piacente, Engin Celep, Irem Atay, Güldem Mercanoğlu, Erdem Yeşilada
Department of Pharmacognosy, Faculty of Pharmacy, Yeditepe University, TR-34755, Kayişdaği, Istanbul, Turkey. email@example.com
From the MeOH extract of Hypericum calycinum, two caffeoylquinic acid derivatives, butyl chlorogenate (1), and chlorogenic acid (2), seven flavonoids, quercetin (3), quercitrin (4), hyperoside (5), isoquercitrin (6), miquelianin (7), rutin (8) and I3,II8-biapigenin (9) and two flavanols,(+)-catechin (10) and (-)-epicatechin (11) were isolated. Identification of the isolates was carried out by spectroscopic analysis including 1D and 2D NMR experiments as well as mass spectrometry. Free radical scavenging activities of the isolated compounds were determined in in-vitro 1,1-diphenyl-2-picrylhydrazyl (DPPH) and nitric oxide (NO) scavenging models. The compounds showed strong DPPH and moderate NO scavenging activities in a concentration dependent manner.(+)-Catechin and (-)-epicatechin were found to be the most active compounds with IC50 values of 4.16 and 4.67 microM for DPPH and 190 and 170 microM for NO scavenging activities, respectively.
Frédéric Martin, Anne-Emmanuelle Hay, Valentin R Quinteros Condoretty, Delphine Cressend, Marianne Reist, Mahabir P Gupta, Pierre-Alain Carrupt, Kurt Hostettmann
Laboratory of Pharmacognosy and Phytochemistry, School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Quai Ernest-Ansermet 30, CH-1211 Geneva 4, Switzerland, Unit of Pharmacochemistry, School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Quai Ernest-Ansermet 30, CH-1211 Geneva 4, Switzerland, and Center for Pharmacognostic Research on Panamanian Flora (CIFLORPAN), College of Pharmacy, University of Panama, Panama.
Extracts from several plants of the family Bignoniaceae from Panama were submitted to a rapid DPPH TLC test for the detection of radical-scavenging activity. The MeOH extract of the stems of Jacaranda caucana, a tree that grows from Costa Rica to Colombia, was selected due to its interesting activity and the lack of phytochemical studies on the polar extract. This extract was partitioned between ethyl acetate, butanol, and water. The EtOAc fraction afforded two new phenylethanoid glycosides (1, 2), along with protocatechuic acid, acteoside, and jionoside D. Further purifications yielded isoacteoside and martynoside. The BuOH fraction afforded a new rhamnosyl derivative of sisymbrifolin (8), a neolignan. The structures were determined by means of spectrometric methods, including 1D and 2D NMR experiments and MS analysis.