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Made available in DSpace on 2022-04-28T19:44:07Z (GMT). No. of bitstreams: 0 Previous issue date: 2022-02-01 Approximately 11.4 million tonnes of solid by-products and an increased amount of waste water will be generated during the 2020/21 coffee harvest. There are currently no truly value-adding uses for these potentially environmentally threatening species. This work presents the most wide-ranging chemical investigation of coffee by-products collected from farms to factories, including eight never previously investigated. Twenty compounds were found for the first time in coffee by-products including the bioactive neomangiferin, kaempferol-3-O-rutinoside, lup-20(29)-en-3-one and 3,4-dimethoxy cinnamic acid. Five by-products generated inside a factory showed caffeine (53.0–17.0 mg.g−1) and/or chlorogenic acid (72.9–10.1 mg.g−1) content comparable to coffee beans, while mature leaf from plant pruning presented not only high contents of both compounds (16.4 and 38.9 mg.g-1, respectively), but also of mangiferin (19.4 mg.g-1) besides a variety of flavonoids. Such by-products are a source of a range of bioactive compounds and could be explored with potential economic and certainly environmental benefits. São Paulo State University (UNESP) Faculty of Agricultural Sciences University of São Carlos (UFSCar) Department of Chemistry Brazilian Agricultural Research Corporation (EMBRAPA) Embrapa Agroenergy The University of Auckland School of Chemical Sciences Centre for Green Chemical Sciences School of Chemical Sciences The University of Auckland São Paulo State University (UNESP) Faculty of Agricultural Sciences

Made available in DSpace on 2019-10-06T16:43:42Z (GMT). No. of bitstreams: 0 Previous issue date: 2019-02-01 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Abstract: We recognize the chemical composition of the acetonic extract of Rhizophora mangle barks (AERM) using mass spectrometry analysis [liquid chromatography (LC)–ESI–IT-MS/MS and matrix-assisted laser desorption/ionization-time of flight-MS (MALDI-TOF)]. Analgesic activity was evaluated by formalin and tail-flick experimental assays. Anti-inflammatory activity was performed by paw edema test induced by carrageenan and 48/80 compounds. The first series of experiments involved [LC]–FIA–IT-MS/MS with 11 separated catechins derivatives until degree of polymerization 3 (DP3). The spectra obtained by MALDI-TOF analysis of the AERM presented two homologous series: one based on polymers of m/z 288 Da increments (up to DP12) and another series based on polymers of m/z [288 + 162] Da increments (up to DP11). In addition to these series of flavan-3-ol, each DP had a subset of masses with a variation of − 16 Da (homologous series of afzelechins—m/z 873–3465 Da) and + 16 Da (homologous series of gallocatechins—m/z 905–3497 Da). A similar pattern with homologous series of gallocatechins and afzelechins could also be observed for a fifth and a sixth monohexoside series: glucogallocatechins (m/z 779–3371) and glucoafzelechins (m/z 747–3339). The intraperitoneal administration of different doses of AERM (50, 150 and 300 µg mL−1) have a morphine-like effect and intense anti-inflammatory activity. Graphical Abstract: [Figure not available: see fulltext.]. Laboratory of Bioprospection of Natural Products (LBPN) UNESP - São Paulo State University/Coastal Campus of São Vicente, Pça Infante Dom Henrique S/N Laboratório de Estudos Avançados em Fitomedicamentos (LEAF) UFMA - Federal University of Maranhão, Av. dos Portugueses, 1966 - Bacanga Embrapa Agroenergy Brazilian Agricultural Research Corporation, W3 Norte, PqEB Laboratory of Bioprospection of Natural Products (LBPN) UNESP - São Paulo State University/Coastal Campus of São Vicente, Pça Infante Dom Henrique S/N FAPESP: 2009/52237-9 FAPESP: 2014/23951-3

Microbial production of xylonic acid can be achieved via xylose oxidation catalyzed by the xylose dehydrogenase enzyme. In the present study, 11 putative xylose dehydrogenases (XDH) from bacterial and fungi were identified through in silico analysis using the sequences of the two XDH previously described. Among them, 6 genes were successfully cloned and expressed in Komagataella phaffii (Pichia pastoris) as demonstrated by the ability of the strains to produce xylonic acid. The best strain was capable of producing up to 37.1 ± 1.9 and 11.7 ± 1.6 g/L of xylonic acid with yields of 0.96 ± 0.02 and 0.40 ± 0.06 g/g in mineral medium and sugarcane bagasse hydrolysate, respectively. The results presented here demonstrated the functionality of 6 newly identified xylose dehydrogenases, increasing the number of XDH described. In addition, the efficiency of K. phaffii as a xylonic acid producer is showed for the first time.

The use of bioprocess to convert low valued biomass or agroindustrial byproducts into high-value chemicals is an emerging area. However, laboratories usually use outdated analytical techniques to identify bioproducts, losing valuable information, such as the identification of unexpected compounds. In this work, we presented a successful systematic and modern analytical approach based on direct infusion mass spectrometry (DIMS) for an automated high-throughput screening of untargeted compounds from glycerin bioconversion process. We describe advantages of DIMS and its combined application with chemometrics towards an untargeted metabolomics approach to analyze several samples in a short time (11 samples per h). Three batches with 34 samples from the bioconversion of glycerin using several filamentous fungi strains were analyzed. Batch 347 was selected as promising, since high value chemicals, such as amide, phenolic and acid compounds, were identified. The platform presented was fast, robust, and versatile, then it could be applied to different bioprocesses.

Xylose fermentation is a bottleneck in second-generation ethanol production. As such, a comprehensive understanding of xylose metabolism in naturally xylose-fermenting yeasts is essential for prospection and construction of recombinant yeast strains. The objective of the current study was to establish a reliable metabolomics protocol for quantification of key metabolites of xylose catabolism pathways in yeast, and to apply this protocol to Spathaspora arborariae. Ultra-high performance liquid chromatography coupled to tandem mass spectrometry (UHPLC-MS/MS) was used to quantify metabolites, and afterwards, sample preparation was optimized to examine yeast intracellular metabolites. S. arborariae was cultivated using xylose as a carbon source under aerobic and oxygen-limited conditions. Ion pair chromatography (IPC) and hydrophilic interaction liquid chromatography-tandem mass spectrometry (HILIC-MS/MS) were shown to efficiently quantify 14 and 5 metabolites, respectively, in a more rapid chromatographic protocol than previously described. Thirteen and eleven metabolites were quantified in S. arborariae under aerobic and oxygen-limited conditions, respectively. This targeted metabolomics protocol is shown here to quantify a total of 19 metabolites, including sugars, phosphates, coenzymes, monosaccharides, and alcohols, from xylose catabolism pathways (glycolysis, pentose phosphate pathway, and tricarboxylic acid cycle) in yeast. Furthermore, to our knowledge, this is the first time that intracellular metabolites have been quantified in S. arborariae after xylose consumption. The results indicated that fine control of oxygen levels during fermentation is necessary to optimize ethanol production by S. arborariae. The protocol presented here may be applied to other yeast species and could support yeast genetic engineering to improve second generation ethanol production. Graphical Abstract ?. Made available in DSpace on 2021-04-06T18:33:52Z (GMT). No. of bitstreams: 1 Abdelnur-ASMassSoectiometry-2017.pdf: 1612418 bytes, checksum: 40ad6176a91413e50eb04942e2ae6edf (MD5) Previous issue date: 2017

Crude glycerol is a by-product of biodiesel production and nowadays has low commercial value for chemical industries. Biotechnological processes may be used to transform this by-product into diverse value-added chemical compounds. In this context, a representative analytical protocol to monitor the production of chemicals from bioprocesses is mandatory. This study presents a novel, simple and fast method developed, validated and based on ultra-high performance liquid chromatography (UPLC) with evaporative light scattering detection (ELSD) using a hydrophilic interaction chromatography column (HILIC) to identify and quantify glycerol, arabitol and mannitol during bioconversion of crude glycerol. Under optimized conditions, these three target analytes were baseline separated with 6 min. Limits of detection (LOD) and quantification (LOQ) ranged from 5.0 to 8.0 and 13.0 to 18.0 ng, respectively. The method showed good precision, stability, repeatability and recovery. Polyols exhibited a regression relationship to the log–log function (R > 0.999) within the concentration ranges from 5.0 to 2000.0 μg mL−1. Average recoveries covering four points were within the range of 94.6–101.7% with the coefficient of variation being ≤3.1% for the three analytes. The intra- and inter-assay precisions were less than 3.9%. This method was successfully applied to real samples obtained after bioconversion of crude glycerol. The developed method was simpler, faster and more sensitive than the conventional HPLC-RID protocol. Thereby, this new method based on HILIC-UPLC-ELSD represents an important analytical protocol for monitoring glycerol conversion in biotechnological processes and helps to select promising microorganisms during bioprospection studies.

The recent increase in the production of crude glycerin through the manufacture of biodiesel has imputed a commercial issue, the excess of this raw material in the market and its constant devaluation, which resulted in the need for new technologies for its use. Crude glycerin can be used in biotechnological processes for the production of high value-added compounds. This study presents novel, simple and fast methods based on ultra-high performance liquid chromatography (UHPLC) using evaporative light scattering detection (ELSD) for simultaneous analysis of ten sugar alcohols with a hydrophilic interaction chromatography (HILIC) column. The selected compounds and their possible stereoisomers have major commercial importance and they can be obtained by biotechnological routes. Under optimized conditions, threitol, erythritol, adonitol, xylitol, arabitol, iditol, sorbitol, mannitol, dulcitol and volemitol can be analyzed simultaneously within 15.0 min. The use of different column temperatures was a key parameter to reach the selectivity during the separation of some stereoisomers. Regression equations revealed a good linear relationship (R > 0.995) over the range from 50.0 to 800.0 ng. Limits of detection (LOD) and quantification (LOQ) ranged from 30.0 to 45.0 ng and 50.0–75.0 ng, respectively. The HILIC-UHPLC-ELSD methods showed good precision with low coefficient of variation (CV%) for the intra- and inter-assays experiments (≤ 5.1%) and high repeatability in terms of retention times for each analyte (≤ 0.5%). The accuracy was confirmed with an average recovery ranging from 92.3 to 107.3%. The developed methods employ an analytical technique more accessible and suitable for routine analyzes and have shown to be suitable for simultaneous analysis of sugar alcohols present in crude bioconverted glycerin samples using different classes of microorganisms.

Made available in DSpace on 2019-10-06T16:59:55Z (GMT). No. of bitstreams: 0 Previous issue date: 2019-03-01 Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Byrsonima intermedia is a species of bush popularly used to treat gastrointestinal disorders, such as gastric ulcers, gastritis, and diarrhea. Previous studies have revealed that the methanolic crude extract of B. intermedia leaves has gastroprotective and healing properties. In this new study, we specifically investigated two purified partitions, ethyl acetate (EtOAc) and water (AcoAq), obtained from the crude extract to characterize the antiulcer effects of these two partitions and the mechanisms of action of this medicinal plant. The healing effects of these partitions on the gastric and duodenal mucosa were assessed after ischemia-reperfusion (I/R) or acetic acid-induced injury. The involvement of tumor necrosis factor-alpha (TNF-alpha), interleukin 1β (IL-1β), interleukin 10 (IL-10), and myeloperoxidase (MPO) activity and glutathione (GSH) levels were determined. The antibacterial activity against Helicobacter pylori was evaluated using microdilution methods. The phytochemical analysis of AcoAq revealed a predominance of oligomeric proanthocyanidins and galloyl quinic esters, whereas EtOAc was found to contain concentrated flavonoids. Both partitions led to a significant reduction in gastric lesions, but AcoAq was more effective than EtOAc with regard to anti-Helicobacter pylori activity in addition to protecting the gastric mucosa against ethanol, non-steroidal anti-inflammatory drugs (NSAIDs) and duodenal mucosal damage induced by cysteamine. Additionally, both partitions were associated with a significant increase in gastric and duodenal healing and increased gastric mucosal GSH content after damage induced by acetic acid. On the other hand, after 6 days of treatment, EtOAc was more effective than AcoAq in ameliorating gastric damage upon initiation of the gastric I/R, which was accompanied by a significant reduction in the activity of gastric mucosal MPO, IL 1-β and TNF-alpha, as well as an elevation in IL-10 and GSH content. These results demonstrate that the oligomeric proanthocyanidins and galloyl quinic esters present in AcoAq were more effective in the prevention of gastric and duodenal ulcers due to the antioxidant effects of these compounds, whereas the flavonoids present in EtOAc were more effective due to their anti-inflammatory activity on the gastric and duodenal tissue. All these results confirm that the rich phytochemical diversity of B. intermedia contributes to the pharmacological actions of this medicinal plant on the gastrointestinal tract in addition to its activity against H. pylori. Departamento de Fisiologia UNESP - Universidade Estadual Paulista Instituto de Biociências Laboratório de Pesquisa de Compostos Bioativos USF- Universidade São Francisco Instituto de Biociências UNESP - Universidade Estadual Paulista Embrapa Agroenergia Embrapa - Empresa Brasileira de Pesquisa Agropecuária Escola de Artes Ciências e Humanidade USP - Universidade de São Paulo Faculdade de Ciências Farmacêuticas UNESP - Universidade Estadual Paulista Departamento de Biologia Vegetal UNICAMP - Universidade de Campinas Instituto de Biologia Departamento de Fisiologia UNESP - Universidade Estadual Paulista Instituto de Biociências Instituto de Biociências UNESP - Universidade Estadual Paulista Faculdade de Ciências Farmacêuticas UNESP - Universidade Estadual Paulista CNPq: 305570/2012-9

Oil palm (E. guineensis), the most consumed vegetable oil in the world, is affected by fatal yellowing (FY), a condition that can lead to the plant’s death. Although studies have been performed since the 1980s, including investigations of biotic and abiotic factors, FY’s cause remains unknown and efforts in researches are still necessary. This work aims to investigate the metabolic expression in plants affected by FY using an untargeted metabolomics approach. Metabolic fingerprinting analysis of oil palm leaves was performed using ultra high liquid chromatography–electrospray ionization–mass spectrometry (UHPLC–ESI–MS). Chemometric analysis, using principal component analysis (PCA) and partial least square discriminant analysis (PLS-DA), was applied to data analysis. Metabolites identification was performed by high resolution mass spectrometry (HRMS), MS/MS experiments and comparison with databases and literature. Metabolomics analysis based on MS detected more than 50 metabolites in oil palm leaf samples. PCA and PLS-DS analysis provided group segregation and classification of symptomatic and non-symptomatic FY samples, with a great external validation of the results. Nine differentially expressed metabolites were identified as glycerophosphorylcholine, arginine, asparagine, apigenin 6,8-di-C-hexose, tyramine, chlorophyllide, 1,2-dihexanoyl-sn-glycero-3-phosphoethanolamine, proline and malvidin 3-glucoside-5-(6″-malonylglucoside). Metabolic pathways and biological importance of those metabolites were assigned. Nine metabolites were detected in a higher concentration in non-symptomatic FY plants. Seven are related to stress factors i.e. plant defense and nutrient absorption, which can be affected by the metabolic depression of these compounds. Two of those metabolites (glycerophosphorylcholine and 1,2-dihexanoyl-sn-glycero-3-phosphoethanolamine) are presented as potential biomarkers, since they have no known direct relation to plant stress.

Jatropha curcas L. is an oil crop that has been studied as a potential source of biodiesel. A high protein pie is produced as a byproduct of the biodiesel production, which could be used as animal feed. However, the pie has toxic compounds, as phorbol esters and other toxins, which prevents the use as animal feed. For this reason, Embrapa (Brazilian Agricultural Research Corporation) has been working in genetic breeding to develop non-toxic J. curcas genotypes. To evaluate this process, a simple and fast analytical technique was employed to obtain responses in a short time. Leaf spray (LS) is a recent ambient ionization mass spectrometry technique in which the sample itself serves as support and ion source. Here, toxic and non-toxic J. curcas leaves were differentiated by LS using a linear ion trap mass spectrometer and partial least squares discriminant analysis (PLS-DA) model chemometrics. It was possible to differentiate toxic and non-toxic leaves and to identify the m/z values that contribute to discrimination between the groups.

The species Astronium urundeuva (Allemao) Engl. and Astronium graveolens Jacq., which are used in Brazilian folk medicine to treat allergies, inflammation, diarrhea and ulcers, were investigated for their composition. The aim of this study was to define a rapid and reliable analytical approach, based on the flow-injection analysis–electrospray ionization–ion trap–tandem mass spectrometry (FIA-ESI-IT-MS-MS) and matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry (MALDI-ToF-MS), to investigate the full range of hydrolyzable tannins present in the extracts of these Astronium species. The MALDI-ToF-MS analysis allowed us to ascertain the presence of hydrolysable tannins in both Astronium species as a series of gallotannins with degrees of polymerization of 7 to 13 galloyl units. Moreover, the analysis by FIA-ESI-IT-MS-MS, as well as confirming this result and chemically defining gallotannins as galloylglucose compounds, highlighted the presence of further classes of hydrolysable tannins, such as hexahydrodiphenoyl esters of glucose and some gallic acid derivatives, providing information about their structure by a careful study of their fragmentation patterns. Finally, the evaluation of the number of positional isomers of gallotannins occurring in both Astronium species was obtained by high-performance liquid chromatography–electrospray ionization–ion trap mass spectrometry (HPLC/ESI-IT-MS). This is the first mass spectrometric evidence relating to the existence of gallotannins in Astronium genus.

Saccharum officinarum bagasse (common name: sugarcane bagasse) and Pennisetum purpureum (also known as Napier grass) are among the most promising feedstocks for bioethanol production in Argentina and Brazil. In this study, both biomasses were assessed before and after acid pretreatment and following hydrolysis with Nasutitermes aquilinus andCortaritermes fulviceps termite gut digestome. The chemical composition analysis of the biomasses after diluted acid pretreatment showed that the hemicellulose fraction was partially removed. The (hemi) cellulolytic activities were evaluated in bacterial culture supernatantsof termite gut homogenates grown in treated and untreated biomasses. In all cases, we detected significantly higher endoglucanase and xylanase activities using pretreated biomasses compared to untreated biomasses, carboxymethylcellulose and xylan. Several protein bands with (hemi) cellulolytic activity were detected in zymograms and two-dimensionalgel electrophoresis. Some proteins of these bands or spots were identified as xylanolytic peptides by mass spectrometry. Finally, the diversity of cultured cellulolytic bacterial endosymbionts associated to both Argentinean native termite species was analyzed. This study describes, for the first time, bacterial endosymbionts and endogenous (hemi) cellulases of two Argentinean native termites as well as their potential application in degradation of lignocellulosic biomass for bioethanol production. Fil: Ben Guerrero, Emiliano. Instituto Nacional de Tecnología Agropecuaria. Centro de Investigación en Ciencias Veterinarias y Agronómicas. Instituto de Biotecnología; Argentina Fil: Arneodo Larochette, Joel Demián. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Instituto Nacional de Tecnología Agropecuaria. Centro de Investigación en Ciencias Veterinarias y Agronómicas. Instituto de Microbiología y Zoología Agrícola; Argentina Fil: Bombarda Campanha, Raquel. Ministerio da Agricultura Pecuaria e Abastecimento de Brasil. Empresa Brasileira de Pesquisa Agropecuaria; Brasil Fil: Oliveira, Patrícia Abrão de. Ministerio da Agricultura Pecuaria e Abastecimento de Brasil. Empresa Brasileira de Pesquisa Agropecuaria; Brasil Fil: Labate, Mônica T. Veneziano. Universidade de Sao Paulo; Brasil Fil: Cataldi, Thaís Regiani. Universidade de Sao Paulo; Brasil Fil: Campos, Eleonora. Instituto Nacional de Tecnología Agropecuaria. Centro de Investigación en Ciencias Veterinarias y Agronómicas. Instituto de Biotecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Cataldi, Ángel Adrián. Instituto Nacional de Tecnología Agropecuaria. Centro de Investigación en Ciencias Veterinarias y Agronómicas. Instituto de Biotecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Labate, Carlos A.. Universidade de Sao Paulo; Brasil Fil: Rodrigues, Clenilson Martins. Ministerio da Agricultura Pecuaria e Abastecimento de Brasil. Empresa Brasileira de Pesquisa Agropecuaria; Brasil Fil: Talia, Paola Monica. Instituto Nacional de Tecnología Agropecuaria. Centro de Investigación en Ciencias Veterinarias y Agronómicas. Instituto de Biotecnología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina

Inflammation and haemorrhage are the main characteristics of tissue injury in botropic envenomation. Although some studies have shown that anti-venom prevents systemic reactions, it is not efficient in preventing tissue injury at the site of the bite. Therefore, this work was undertaken to investigate the anti-inflammatory effects of the methanolic extract and fractions from D. elliptica and to evaluate the role of matrix metalloproteinases (MMPs) in this process. Effects of the extract and fractions from D. elliptica were evaluated using a carrageenan-induced paw oedema model in rats, and leukocyte rolling was visualized by intravital. The quantification of MMPs activities (MMP-2 and MMP-9) extracted from the dermis of mice treated with extract and fractions alone or incubated with venom was determined by zymographic analyses. Our results show that intraperitoneal (i.p.) injection of fractions significantly reduced paw oedema after the carrageenan challenge. Treatment with the tannins fraction also resulted in considerable inhibition of the rolling of leukocytes and this fraction was able to decrease the activation of MMP-9. These results confirmed the anti-inflammatory activity of the methanolic extract and tannins fraction of D. elliptica and showed that the dermonecrosis properties of B. jararaca venom might be mediated through the inhibition of MMP-9 activity.

The methanolic extract of the leaves of the medicinal plant Byrsonima crassa (Malpighiaceae) contain flavonoids with antioxidant activity. They were separated in a preparative scale using high-speed counter-current chromatography. The optimum solvent system used was composed of a mixture of ethyl acetate– n -propanol–water (140:8:80 (v/v/v)) and led to a successful separation between monoglucosilated flavonoids (quercetin-3- O -α- l -arabinoside, quercetin-3- O -β- d -galactoside) and the biflavonoid amentoflavone in only 3.5 h. The purities of quercetin-3- O -α- l -arabinoside (95 mg), quercetin-3- O -β- d -galactoside (16 mg) and the biflavonoid amentoflavone (114 mg) were all isolated at purity over 95%. Identification was performed by 1 H NMR, 13 C NMR and UV analyses.

Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-27T11:28:37Z No. of bitstreams: 0Bitstream added on 2014-05-27T14:32:19Z : No. of bitstreams: 1 2-s2.0-84875582868.pdf: 425808 bytes, checksum: 6f3e208a2c35096d12d2ec866688f606 (MD5) Made available in DSpace on 2014-05-27T11:28:37Z (GMT). No. of bitstreams: 0 Previous issue date: 2013-03-01 The present study investigates the chemical composition of the African plant Parkia biglobosa (Fabaceae) roots and barks by Liquid Chromatography - Electrospray Ionization and Direct Injection Tandem Mass Spectrometry analysis. Mass spectral data indicated that B-type oligomers are present, namely procyanidins and prodelphinidins, with their gallate and glucuronide derivatives, some of them in different isomeric forms. The analysis evidenced the presence of up to 40 proanthocyanidins, some of which are reported for the first time. In this study, the antiradical activity of extracts of roots and barks from Parkia biglobosa was evaluated using DPPH method and they showed satisfactory activities. Department of Organic Chemistry Institute of Chemistry UNESP - Sao Paulo State University, 14800-900, Araraquara, Sao Paulo Department of Organic Chemistry Faculty of Science University of Yaounde i, PO Box 812, Yaounde Center of Chemical and Instrumental Analysis Embrapa Agroenergy PqEB, W3 North, 70770-901, Brasilia, Distrito Federal Experimental Campus of Sao Vicente UNESP - Sao Paulo State University, 11350-000, Sao Vicente, Sao Paulo Department of Organic Chemistry Institute of Chemistry UNESP - Sao Paulo State University, 14800-900, Araraquara, Sao Paulo Experimental Campus of Sao Vicente UNESP - Sao Paulo State University, 11350-000, Sao Vicente, Sao Paulo

Leaves from Carpolobia lutea (Polygalaceae) were screened to establish the antiulcer ethnomedicinal claim and to quantitatively isolate, elucidate the active compounds by semi-preparative HPLC. The anti-nociceptive effects of Carpolobia lutea (CL) G. Don (Polygalaceae) organic leaf extracts were tested in experimental models in mice. The anti-nociceptive mechanism was determined using tail-flick test, acetic acid-induced abdominal constrictions, formalin-induced hind paw licking and the hot plate test. The fractions (ethanol, ethyl acetate, chloroform, n-hexane) and crude ethyl acetate extract of CL (770 mg/kg, i.p.) produced significant inhibitions of both phases of the formalin-induced pain in mice, a reduction in acetic acid-induced writhing as well as and an elevation of the pain threshold in the hot plate test in mice. The inhibitions were greater to those produced by indomethacin (5 mg/kg, i.p.). Ethyl acetate fraction revealed cinnamic and coumaric acids derivatives, which are described for the first time in literature. These cinnamalglucosides polyphenols characterised from CL may in part account for the pharmacological activities. These findings confirm its ethnomedical use in anti-inflammatory pain and in pains from gastric ulcer-associated symptoms.

When catechins are found in plant extracts, they are almost always identified as catechin and/or epicatechin probably due to stereoselectivity of the enzymes involved in the biosynthesis of these substances. However, the lack of reports regarding to ent-catechin as well as ent-epicatechin does not necessarily mean that these compounds have not been produced. In fact, most of the previous reports used chromatographic conditions not suitable for such separation. This article describes a simple and reliable analytical HPLC-PAD-CD method for simultaneous determination of catechin diastereomers both in infusions and extracts from the leaves of Byrsonima species. The direct separation of catechin, ent-catechin, epicatechin, and ent-epicatechin was obtained in normal phase by HPLC-PAD-CD using Chiralcel OD-H as chiral stationary phase and n-hexane/ethanol with 0.1% of TFA as mobile phase. Chirality 22: 726-733, 2010. (C) 2010 Wiley-Liss, Inc.

Davilla nitida and Davilla elliptica (Dilleniaceae) are plants that occur predominantly in the cerrado region of South America. They are used in popular medicine to treat stomach diseases, diarrhea and swelling, particularly of the lymph nodes and testicles. Chemical investigation of these two plant species led to the identification of the compounds myricetin-3-O-α-l-rhamnoside (myricitrin), quercetin-3-O-α-l-rhamnoside (quercitrin), myricetin, quercetin and gallic acid derivatives in the leaves of D. nitida and D. elliptica. Therefore, it was concluded that the two species of Davilla possess qualitatively similar chemical profiles. In the present study, the mutagenic and genotoxic potential of these plants and of their isolated compounds was tested in the Salmonella typhimurium assay (Ames test) with strains TA100, TA98, TA102 and TA97a, in the micronucleus test with peripheral blood cells of mice treated in vivo, and in plasmid DNA to analyze DNA strand-breaks. In the assessment of mutagenic potential by the Ames test, extracts from both plant species and a D. nitida ethyl-acetate fraction induced positive responses. On the other hand, none of the extracts showed genotoxic activity in the mouse cells. In the presence of metal ion, D. nitida and D. elliptica aqueous and ethyl-acetate fractions, as well as their isolated compounds, induced single- and double-strand-breaks in plasmid DNA in a cell-free system.

Made available in DSpace on 2013-08-28T14:12:26Z (GMT). No. of bitstreams: 1 WOS000264565000014.pdf: 119866 bytes, checksum: 80217037ccfd8ca2d39ea1accf4c27bc (MD5) Made available in DSpace on 2013-09-30T19:10:41Z (GMT). No. of bitstreams: 2 WOS000264565000014.pdf: 119866 bytes, checksum: 80217037ccfd8ca2d39ea1accf4c27bc (MD5) WOS000264565000014.pdf.txt: 24181 bytes, checksum: 056565f08078e2cf0d624eb8c0faa588 (MD5) Previous issue date: 2009-03-01 Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-20T13:49:52Z No. of bitstreams: 2 WOS000264565000014.pdf: 119866 bytes, checksum: 80217037ccfd8ca2d39ea1accf4c27bc (MD5) WOS000264565000014.pdf.txt: 24181 bytes, checksum: 056565f08078e2cf0d624eb8c0faa588 (MD5) Made available in DSpace on 2014-05-20T13:49:53Z (GMT). No. of bitstreams: 2 WOS000264565000014.pdf: 119866 bytes, checksum: 80217037ccfd8ca2d39ea1accf4c27bc (MD5) WOS000264565000014.pdf.txt: 24181 bytes, checksum: 056565f08078e2cf0d624eb8c0faa588 (MD5) Previous issue date: 2009-03-01 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Around 20,000 snakebites are reported annually in Brazil and 90% of them are inflicted by species of the genus Bothrops. Intravenous administration of antibothropic antivenom neutralizes the systemic actions, but it is of little effect on the reversal of local symptoms and often induces adverse reactions, a context that drives the search for complementary treatments for snakebite accidents. Vegetable extracts with a range of antiophidian activities constitute an excellent alternative. In this study, we investigated the anti-hemorrhagic effects of Mouriri pusa Gardn. (Melastomataceae), Byrsonima crassa Niedenzu (Malpighiaceae), Davilla elliptica St. Hill. (Dilleniaceae) and Strychnos pseudoquina St. Hil. (Loganiaceae) against Bothrops jararaca venom. The methanolic extracts from M. pusa (leaves), B. crassa (leaves) and D. elliptica (leaves) showed total neutralization capacity against local hemorrhages. The amenthoflavone and quercetin fractions from B. crassa and the flavonoids fractions (quercetin and myricetin) from M. pusa and D. elliptica also showed total neutralization capacity. We conclude that flavonoids derived from myricetin, quercetin and amenthoflavone play an important role in the anti-hemorrhagic potential of these Brazilian vegetables species against B. jararaca venom. São Paulo State Univ, UNESP, Dept Physiol, Botucatu, SP, Brazil São Paulo State Univ, UNESP, Dept Organ Chem, Araraquara, SP, Brazil Ctr Appl Toxinol, Instituto Butantan, São Paulo, Brazil São Paulo State Univ, UNESP, Dept Physiol, Botucatu, SP, Brazil São Paulo State Univ, UNESP, Dept Organ Chem, Araraquara, SP, Brazil

Byrsonima basiloba A. Juss. species is a native arboreal type from the Brazilian "cerrado" (tropical American savanna), and the local population uses it to treat diseases, such as diarrhea and gastric ulcer. It belongs to the Malpighiaceae family, and it is commonly known as "murici." Considering the popular use of B. basiloba derivatives and the lack of pharmacological potential studies regarding this vegetal species, the mutagenic and antimutagenic effect of methanol (MeOH) and chloroform extracts were evaluated by the Ames test, using strains TA97a, TA98, TA100, and TA102 of Salmonella typhimurium. No mutagenic activity was observed in any of the extracts. To evaluate the antimutagenic potential, direct and indirect mutagenic agents were used: 4 nitro-o-phenylenediamine, sodium azide, mitomycin C, aflatoxin B(1), benzo[a]pyrene, and hydrogen peroxide. Both the extracts evaluated showed antimutagenic activity, but the highest value of inhibition level (89%) was obtained with the MeOH extract and strain TA100 in the presence of aflatoxin B(1). Phytochemical analysis of the extracts revealed the presence of n-alkanes, lupeol, ursolic and oleanolic acid, (+)-catechin, quercetin-3-O-alpha-L-arabinopyranoside, gallic acid, methyl gallate, amentoflavone, quercetin, quercetin-3-O-(2"-O-galloyl)-beta-D-galactopyranoside, and quercetin-3-O-(2"-O-galloyl)-alpha-L-arabinopyranoside.

Direct flow injection electrospray ionization ion trap tandem mass spectrometry (ESI-IT-MS/MS) was used to investigate the polyphenolic compounds present in an infusion from the barks of Hancornia speciosa Gom. (Apocynaceae), a native Brazilian plant popularly known as 'mangabeira', used as a source of nutrition and against gastric disorders. After a simple sample filtration pretreatment the characteristic fingerprint of the infusion was performed in negative ion ESI mode in a few minutes. At low capillary-voltage activation, the deprotonated molecules ([M--H]-) were observed and using collision-induced dissociation the product ion spectra showed the presence of a homologous series of B-type proanthocyanidins, as well as another series containing their respective C-glycosylated derivatives, with a degree of polymerization from 1 up to 6 units of interlinked catechins. Therefore, direct flow injection allowed us to identify the key compounds without preparative isolation of the components.

Submitted by Guilherme Lemeszenski (guilherme@nead.unesp.br) on 2013-08-22T18:48:37Z No. of bitstreams: 1 S0100-40422006000500011.pdf: 172804 bytes, checksum: 37748f06447925b80cf74b36f09a67bc (MD5) Made available in DSpace on 2013-08-22T18:48:37Z (GMT). No. of bitstreams: 1 S0100-40422006000500011.pdf: 172804 bytes, checksum: 37748f06447925b80cf74b36f09a67bc (MD5) Previous issue date: 2006-10-01 Made available in DSpace on 2013-09-30T19:10:46Z (GMT). No. of bitstreams: 2 S0100-40422006000500011.pdf: 172804 bytes, checksum: 37748f06447925b80cf74b36f09a67bc (MD5) S0100-40422006000500011.pdf.txt: 16020 bytes, checksum: 6ef9c793c210961b4642bf0707f967be (MD5) Previous issue date: 2006-10-01 Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-20T14:21:19Z No. of bitstreams: 2 S0100-40422006000500011.pdf: 172804 bytes, checksum: 37748f06447925b80cf74b36f09a67bc (MD5) S0100-40422006000500011.pdf.txt: 16020 bytes, checksum: 6ef9c793c210961b4642bf0707f967be (MD5) Made available in DSpace on 2014-05-20T14:21:19Z (GMT). No. of bitstreams: 2 S0100-40422006000500011.pdf: 172804 bytes, checksum: 37748f06447925b80cf74b36f09a67bc (MD5) S0100-40422006000500011.pdf.txt: 16020 bytes, checksum: 6ef9c793c210961b4642bf0707f967be (MD5) Previous issue date: 2006-10-01 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) High-speed counter-current chromatography (HSCCC) is a major tool for the fast separation of natural products from plants. It was used for the preparative isolation of the flavonoid monoglucosides present in the aerial parts of the Davilla elliptica St. Hill. (Dilleniaceae). This species is used in Brazilian folk medicine for the treatment of gastric disorders. The optimum solvent system used was composed of a mixture of ethyl acetate-n-propanol-water (140:8:80, v/v/v) and led to a successful separation of quercetin-3-O-alpha-L-rhamnopyranoside and myricetin-3-O-alpha-L-rhamnopyranoside in approximately 3.0 hours with purity higher than 95%. Identification was performed by ¹H NMR, 13C NMR and HPLC-UV-DAD analyses. Universidade Estadual Paulista Instituto de Química Departamento de Química Orgânica Universidade Estadual Paulista Instituto de Biociências Departamento de Fisiologia Universidade Estadual de Campinas Instituto de Biologia Departamento de Fisiologia e Biofísica Universidade Estadual Paulista Instituto de Química Departamento de Química Orgânica Universidade Estadual Paulista Instituto de Biociências Departamento de Fisiologia

Byrsonima intermedia is a native species of the cerrado formation (tropical American savannah). In Brazil, this plant has been used for the treatment of fever, in ulcers, as a diuretic, as antiasthmatics and in skin infections. Members of the genus Byrsonima (Malpighiaceae) are employed not only in the folk medicine but also as food to make juice, jellies and liquor. The aim of this work was to evaluate the mutagenic effects of Byrsonima intermedia, common name 'murici'. Phytochemical analysis of methanol extract furnished (+)-catechin, (-)-epicatechin, quercetin-3-O-beta-d-galactopyranoside, methyl gallate, gallic acid, quercetin-3-O-alpha-l-arabinopyranoside, amentoflavone, quercetin, quercetin-3-O-(2''-O-galloyl)-beta-galactopyranoside and quercetin-3-O-(2''-O-galloyl)-alpha-arabinopyranoside. Methanol, hydromethanol and chloroform extracts were evaluated in mutagenic assay with Salmonella typhimurium (Ames test) and mice (Micronucleus test). The methanolic extract presented signs of mutagenic activity for the strains TA98 and TA100 in the Ames assay. Mutagenicity was not observed in vivo.

The hydroethanolic extract of the leaves (HEL) and bark (HEB) obtained from Alchornea castaneaefolia (Euphorbiaceae) were investigated for their ability to prevent ulceration of the gastric mucosa in animal models. HEL (500 and 1000 mg/kg) and HEB (1000 mg/kg) significantly reduced the gastric injuries induced by the combination of HCl/ethanol and lowered the severity of gastric damage formation induced by indomethacin/bethanechol in mice. Further investigation showed that HEL also inhibited formation of ulcers in mice submitted to stress and pylorus ligature, but HEL did not modify gastric juice parameters in Shay mice. HEL was also effective in promoting the healing process in chronic gastric ulcer induced by acetic acid in rats. An enriched flavonoidic fraction (EFF at dose of 100 mg/kg) obtained from HEL reduced gastric lesions induced by HCl/ethanol and indomethacin/bethanechol in mice. Although EFF did not modify the amount of free mucus production by gastric mucosa, it was able to increase prostaglandin production. When administered to rats submitted to ethanol-induced gastric lesions, EFF increased the somatostatin serum levels, while the gastrin serum levels were proportionally decreased. Phytochemical investigation on HEL and EFF led to the isolation of flavonoids glycosides as the main compounds, thus suggesting that these substances may be involved in the observed antiulcer activity.

Background : The stem-bark extract of Carpolobia lutea (Polygalaceae), used in ethno-medicine as anti-diarrhea was pharmacologically evaluated. This was the first report of assessment of the ethanolic stem extract (ESE), of C. lutea as anti-diarrhoeal agent in rats. The anti-diarrhoeal effects, acute toxicity and ionic profile are investigated and reported. Materials and Methods : The acute toxicity was established using Lock’s method. The anti-diarrhoeal effects were demonstrated using castor oilinduced diarrheal and fluid accumulation and its effect on normal intestinal transit. The mechanism elucidated using yohimbine, isosorbide dinitrate, and diphenoxylate. The elemental and ionic profile of ESE was established using inductively coupled argon-plasma emission spectrometer and potentiometric titration respectively. The finger print of ESE was revealed by Jasco (Tokyo, Japan), HPLC and active compounds by phytochemical screening using standard procedure. Results : The LD 50 obtained is 866.025 mg/kg (i.p). The doses of 43.3, 86.6, and 173.2 mg/kg of ESE showed inhibition of castor oil–induced diarrheal (p

Liquid chromatography-electrospray ionization multistage ion trap mass spectrometry (LC-ESI-IT-MSn) was used to analyze the secondary metabolites in the methanol extract of the capitulae of Eriocaulon ligulatum. The major components were mono-and diglycosides of flavonoids and naphthopyranones. Eleven compounds, including four new flavonol glycosides, were identified based on their fragmentation patterns in MS experiments and on NMR analysis of the isolated compounds. The described data may contribute to a better understanding of the taxonomic classification of the Eriocaulaceae family.

Made available in DSpace on 2013-09-27T14:53:43Z (GMT). No. of bitstreams: 1 WOS000302437200001.pdf: 617476 bytes, checksum: a0fd9fa08cd1488bcbda7eae921bde96 (MD5) Previous issue date: 2012-03-27 Made available in DSpace on 2013-09-30T18:06:21Z (GMT). No. of bitstreams: 1 WOS000302437200001.pdf: 617476 bytes, checksum: a0fd9fa08cd1488bcbda7eae921bde96 (MD5) Previous issue date: 2012-03-27 Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-20T13:49:28Z No. of bitstreams: 1 WOS000302437200001.pdf: 617476 bytes, checksum: a0fd9fa08cd1488bcbda7eae921bde96 (MD5) Made available in DSpace on 2014-05-20T13:49:28Z (GMT). No. of bitstreams: 1 WOS000302437200001.pdf: 617476 bytes, checksum: a0fd9fa08cd1488bcbda7eae921bde96 (MD5) Previous issue date: 2012-03-27 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) Ethnopharmacological relevance: An ethnopharmacological survey indicated that the leaves of Byrsonima intermedia A. Juss. (Malpighiaceae), a medicinal species commonly found in the Brazilian Cerrado, can be used against gastroduodenal disorders, such as gastric ulcers and diarrhea.Aim of the study: The objective of this study was to evaluate the effects of a methanolic extract of Byrsonima intermedia (MBI) leaves on gastric and duodenal ulcers and to assess the antimicrobial and antidiarrheal effects of this extract.Material and methods: The anti-ulcerogenic effect of MBI was investigated with different ulcerogenic agents in rodents (mice and rats), including non-steroidal anti-inflammatory drug (NSAID). HCl/ethanol, pyloric ligature, absolute ethanol, cysteamine and ischemia-reperfusion. The gastroprotective effect of MBI was assessed by analysing the volume of gastric juice, pH, total acidity, mucus, NO, sulfhydryl compound, vanilloid receptor, glutathione (GSH) levels, and myeloperoxidase (MPO) activity in the gastric and duodenal mucosa. The gastric and duodenal healing effects of MBI were also evaluated during 7 or 14 days of treatment. The antidiarrheal action (measured by intestinal motility and diarrhea induced by castor oil) and anti-bacterial action of MBI against Staphylococcus aureus, Escherichia coli and Helicobacter pylon were also evaluated by microdilution methods.Results: The phytochemical profile from MBI indicated the presence of phenolic acids, flavan-3-ols, oligomeric proanthocyanidins, and flavonoids. MBI (500 mg/kg, p.o.) significantly inhibited totally gastric and duodenal lesions (69%) and healed gastric (49% on 14 days) and duodenal lesions (45% on 7 and 14 days). The MBI exert gastroprotective action by participation of endogenous sulfhydryl compounds, vanilloid receptors and increase in GSH level to effective gastric and duodenal protection. MBI also displayed curative (42%) and preventive (49%) antidiarrheal effects by involvement of opiate receptors and also antimicrobial effects in vitro.Conclusions: Byrsonima intermedia leaves present gastroprotective, healing and antidiarrheal activities, supporting previous claims that its traditional use can treat gastrointestinal disorders. (C) 2011 Elsevier B.V. All rights reserved. Univ Estadual Paulista, UNESP, Dept Fisiol, Inst Biociencias, BR-18618970 Botucatu, SP, Brazil Univ Estadual Paulista, UNESP, Dept Quim Organ, Inst Quim, BR-14801970 Araraquara, SP, Brazil São Paulo State Univ, USP Leste, Escola Artes Ciencias & Humanidades, BR-03828000 São Paulo, Brazil Univ Estadual Paulista, UNESP, Dept Ciencias Biol, BR-14801970 Araraquara, SP, Brazil Univ Estadual Campinas, UNICAMP, Dept Biol Vegetal, Inst Biol, BR-13083862 Campinas, SP, Brazil Univ. Estadual Paulista-UNESP – Departamento de Fisiologia, Instituto de Biociências, cp 510, CEP 18618-970, Botucatu, SP, Brazil Univ. Estadual Paulista-UNESP – Departamento de Química Orgânica, Instituto de Química, cp 355, CEP 14801-970, Araraquara, SP, Brazil Univ. Estadual Paulista-UNESP – Departamento de Ciências Biológicas, cp 970, CEP 14801-970, Araraquara, SP, Brazil Univ Estadual Paulista, UNESP, Dept Ciencias Biol, BR-14801970 Araraquara, SP, Brazil

The purpose of the present study was to investigate antitumour and anti-inflammatory activities of flavonoids isolated from Byrsonima crassa, Davilla elliptica and Mouriri pusa. The antitumour activity was measured by the MTT assay in murine mammary tumour cells (LM2) and the IC50 values of the flavonoids tested ranged from (31.5 ± 2.97) to (203.1 ± 5.9) μg/ml. The flavonoids 1 (myricetin-3-O-α-L-rhamnopyranoside) and 3 (quercetin-3-O-galactopyranoside) from D. elliptica were the most active ones against the tumour cells. The same samples were tested to determine the inhibition of the release of nitric oxide (NO) and of the tumour necrosis factor-alpha (TNF-α) in murine macrophages by the Griess and ELISA sandwich assay, respectively. Almost all the samples showed inhibitory activity to the release of NO but not of TNF-α. Of all substances tested, flavonoids 2 (quercetin) and 6 (myricetin) may show promising activity in the treatment of murine breast cancer by immunomodulatory and antiproliferative activities. Fil: Carli, Camila B. De A.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: De Matos, Djamile C.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: Lopes, Flávia C. M.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: Maia, Danielle C. G.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: Dias, Maristela B.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: Sannomiya, Miriam. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: Rodrigues, Clenilson M.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: Andreo, Marcio A.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: Vilegas, Wagner. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil Fil: Colombo, Lucas Luis. Universidad de Buenos Aires. Facultad de Medicina. Instituto de Oncología "Ángel H. Roffo"; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina Fil: Carlos, Iracilda Z.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil

The biodiversity of Brazil contains an extraordinary number of compounds from natural products with a wide and complex variety of molecular structures, therefore representing an economic potential in biomasses to be explored. Plant systems are the principal source of medicine and directly contribute to the development of new drugs in addition to agrochemicals, cosmetics, fine chemicals and nutraceuticals. Besides plants, other biomasses can be used as raw material, including marine organisms and microorganisms such as extremophilic and endophytic microbes. Interest in natural products for diverse uses is attributed to their different bioactivities, low toxicity and environmental sustainability. Based on these attributes, other non-biological applications of natural products from biomasses have been reported for use in textiles, antifouling coating in marine transportation, wood adhesives, industrial polymers and biofuel. After extractions of natural products of pharmaceutical interest or industrial application, such as polymers, or even of metabolites for biofuels, the residues (e.g., fibers) or other compounds (e.g., nutrients) are discarded generating unnecessary environmental pollution, but they could be used for the production of different value-added products. Some examples of residues that are being explored for added value by extracting other natural metabolites are olive and apple pomace, macauba and carnauba cakes, and cashew nut shell liquid. Residues and by-products derived from different biomasses in Brazil are a potential source of compounds of biological and industrial interest and therefore must be investigated in order to add value to the entire supply chain of natural product.

Submitted by Vitor Silverio Rodrigues (vitorsrodrigues@reitoria.unesp.br) on 2014-05-27T11:23:49Z No. of bitstreams: 0Bitstream added on 2014-05-27T14:46:22Z : No. of bitstreams: 1 2-s2.0-58849096287.pdf: 135167 bytes, checksum: 69e8a68599f9388948dd10918321b75c (MD5) Made available in DSpace on 2014-05-27T11:23:49Z (GMT). No. of bitstreams: 0 Previous issue date: 2008-12-01 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) The methanolic extract from the barks of the medicinal plant Qualea parviflora (Vochysiaceae) was fractionated by column chromatography over silica gel followed by gel permeation over Sephadex LH-20 to give 3,3′-di-O- methylellagic acid-4-O-β-D-glucopyranoside (1), 3-O-methylellagic acid-4′-O-α-L-rhamnopyranoside (2), 3,3′,4-tri-O-methylellagic acid-4′-O-β-D-glucopyranoside (3), and 3,3′-di-O-methylellagic acid (4), together with triterpenes and saponins. We also performed comparative analyses among this species and Q. grandiflora and Q. multiflora using high-pressure liquid chromatography. The biological assays showed that, when compared to the standard ellagic acid, compounds 1-4 are less cytotoxic but have a lower capacity of stimulating murine peritoneal macrophages to release nitric oxide and tumoural-α necrose factor. © 2008 Verlag der Zeitschrift für Naturforschung. UNESP - São Paulo State University Instituto de Química de Araraquara, C. Postal 355, 14801-970, Araraquara, SP UNESP - São Paulo State University Faculdade de Ciências Farmacêuticas, C. Postal 502, 14801-902, Araraquara, SP UNICAMP - Campinas State University Instituto de Química, 13083-970, Campinas, SP UNESP - São Paulo State University Departamento de Farmacologia Instituto de Biociências, 18618-000, Botucatu, SP UNESP - São Paulo State University Instituto de Química de Araraquara, C. Postal 355, 14801-970, Araraquara, SP UNESP - São Paulo State University Faculdade de Ciências Farmacêuticas, C. Postal 502, 14801-902, Araraquara, SP UNESP - São Paulo State University Departamento de Farmacologia Instituto de Biociências, 18618-000, Botucatu, SP FAPESP: 02/05503-6

Neea theifera Oerst. (Nyctaginaceae) is widely used in Brazilian folk medicine for the treatment of gastric ulcers and inflammation. Phytochemical investigation of the leaves of Neea theifera afforded the isolation of the new flavone luteolin-7-O-[2''-O-(5'''-O-feruloyl)- beta-D-apiofuranosyl]-b-D-glucopyranoside (1) besides the eight-known compounds vitexin, isovitexin, isoorientin, orientin, vicenin-2, chrysoeriol, apigenin and luteolin. Their chemical identification was established by NMR spectroscopic methods including 2D-NMR, as well as UV and ESI-MS analyses. Neea theifera Oerst. (Nyctaginaceae) é amplamente utilizada na medicina popular brasileira para tratamento de úlceras gástricas e inflamação. A investigação fitoquímica das folhas de Neea theifera permitiu o isolamento e identificação da nova flavona luteolina-7-O-[2''-O-(5'''-O-feruloil)- beta-D-apiofuranosil]-beta-D-glucopiranosídeo (1) além dos oito compostos conhecidos vitexina, isovitexina, isoorientina, orientina, vicenina-2, crisoeriol, apigenina e luteolina. A identificação química foi realizada por métodos espectroscópicos incluindo RMN-2D, bem como análises no UV e IES-EM.

Made available in DSpace on 2022-04-29T00:13:28Z (GMT). No. of bitstreams: 0 Previous issue date: 2007-01-01 A method for the isolation of three compounds from the infusion of leaves of Byrsonima basiloba A. Juss. by high-speed counter-current chromatography (HSCCC) was developed. This technique led to the separation of a novel compound, quercetin 3-O-α-L-rhamnopyranosyl-(1→3)-O-[α-L- rhamnopyranosyl-(1→6)]-β-D-allopyranoside, and two known compounds quercetin-3-O-α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranoside and (+)-catechin in 4 h with purities of over 92%. The structures of the compounds were determined by one- and two-dimensional NMR spectroscopy and HPLC. Departamento de Química Orgânica Instituto de Quimica UNESP, Rua Francisco Degni s/n, Bairro Quitandinha, CEP 14800-900 Araraquara, SP Departamento de Fisiologia e Biofisica Instituto de Biologia, Unicamp-Campinas - SP Departamento de Química Orgânica Instituto de Quimica UNESP, Rua Francisco Degni s/n, Bairro Quitandinha, CEP 14800-900 Araraquara, SP