Synthesis of potentially bioactive PABA-related N-(aminoalkyl)lactamic amino acids and esters via selective SNAr reactions

Potentially bioactive N-(aminoalkyl)lactamic amino acids and esters were synthesized in satisfactory to good yields by SNAr reactions of aromatic acids with N-(3-aminopropyl)lactams followed by esterification with tertiary amino alcohols. The addition-elimination SNAr mechanism was confirmed by NMR and MS measurements.

Production of alcoholic beverage from ginger: study of fermentation process and final product quality

Introduction: In Brazil part of the production of ginger is of inadequate quality for export. The production of spirit from felt-over rhizomes is an alternative of great interest to producers of these rhizomes. Aim: Aiming to increase the value of felt-over rhizomes, this work aimed to study the use of ginger as a raw material for alcoholic beverage production. It was evaluated the effect of fermentation conditions on the components of fermented alcoholic, as well as, the quality of alcoholic distilled beverage of ginger. Methods: Dehydrated ginger passed by enzymatic hydrolysis-saccharification processes. The hydrolysate obtained was analyzed for sugar profile in HPLC. The alcoholic fermentation process followed the central composite rotational design for three factors: fermentation temperature (23 to 37ºC), time of fermentation (17 to 33 h) and concentration of inoculum (0.22 to 3.00%). The fermented alcoholic obtained was analyzed in HPLC for the contents of ethanol, methanol, glycerol and residual sugars. The distillated alcoholic beverage of ginger was analyzed for ethanol, methanol, acetaldehyde, ethyl acetate and higher alcohols in the gas chromatography (GC). In addition, copper content and acidity were analyzed Results: Sugar profile of the ginger hydrolysate revealed the presence of 77.8% of glucose. Data analysis of fermentation process showed influence of temperature on ethanol and methanol content of the fermented alcoholic of ginger. Time of fermentation had effect on glycerol content. All parameters of process had influence on residual sugars contents. The HPLC analysis has shown presence of methanol, ethyl acetate, aldehyde, acids, higher alcohols and esters in distilled alcoholic beverage of ginger. Conclusion: Fermented alcoholic of ginger with higher levels of ethanol can be obtained under the conditions of 1.5% w/w of inoculum, 30°C of temperature and 24 hours of fermentation time. In this condition of fermentation process the beverage of ginger had good quality.

Degradation of the antibiotic amoxicillin by photo-Fenton process - Chemical and toxicological assessment

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Constituintes químicos de Hyptidendron canum (Pohl ex Benth.) R. Harley (Lamiaceae)

Chemical investigation of Hyptidendron canum stems resulted in the isolation of betulinic, ursolic and euscaphic acids. From the leaves were isolated 3β-O-β-galactopiranosilsitosterol, ursolic aldehyde, and mixtures of maslinic acid and 2α-hydroxyursolic acid, α and β-amyrin, uvaol and erythrodiol, sitosterol and stigmasterol, spathulenol and globulol. Hexane and chloroform leave fractions as well as ursolic and betulinic acids showed antifungal activities against the yeast form of Paracoccidioides brasiliensis.

Influência do material do alambique na composição química das aguardentes de cana-de-açúcar

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

2,3-Dihydrobenzofuran neolignans from Aristolochia pubescens

From a hexane extract of stems and roots of Aristolochia pubescens, the new neolignans (2S,3S,1'R,2'R)- and (2S,3S, 1'S,2'R)-2,3-dihydro-5-(1',2'-dihydroxypropyl)-2-(4-hydroxy-3-methylbenzofuran) and (2S,3S,1'R,2'R)- and (2S,3S,1'S,2'R)-2,3-dihydro-5-(1',2'-dihydroxypropyl)-2-(3,4-dimethoxyphenyl)-7-methoxy-3-methyl-benzofuran were isolated, together with the known neolignan licarin A, and its bisnor-neolignan aldehyde and acid derivatives. In addition, sitosterol, 8R,9R-oxide-beta-caryophyllene, kobusone, ent-kauran-16 alpha, 17-diol, vanillin, vanillic acid, (+)-sesamin, (+)eudesmin, and (-)-cubebin were isolated. The structures of the new compounds have been elucidated by spectroscopic methods and by chemical transformation using Mosher's acid chloride. (C) 1999 Elsevier B.V. Ltd. All rights reserved.

Ácido cafeico e seus ésteres: inibição do burst oxidativo de neutrófilos e efeito anti-Helicobacter pylori

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Structural characterization of diastereoisomeric ethano adducts derived from the reaction of 2'-deoxyguanosine with trans,trans-2,4-decadienal

Background levels of exocyclic DNA adducts have been detected in rodent and human tissues. Several studies have focused on bifunctional electrophiles generated from lipid peroxidation as one of the endogenous sources of these lesions. We have previously shown that the reaction of 2'-deoxyguanosine (dGuo) with trans,trans-2,4-decadienal (DDE), a highly cytotoxic aldehyde generated as a product of lipid peroxidation in cell membranes, results in the formation of a number of different base derivatives. Three of these derivatives have been fully characterized as 1,N-2-etheno-2'-deoxyguanosine adducts. In the present work, four additional adducts, designated A3-A6, were isolated from in vitro reactions by reversed-phase HPLC and fully characterized on the basis of spectroscopic measurements. Adducts A3-A6 are four diastereoisomeric 1,N-2-hydroxyethano-2'-deoxyguanosine derivatives possessing a carbon side chain with a double bond and a hydroxyl group. The systematic name of these adducts is 6-hydroxy3-(2'-deoxy-beta-D-erythro-pentafuranosyl)-7-((E)-1-hydroxy-oct-2-enyl)-3,5,6,7-tetrahydro-imidazo- [1,2-a]purin-9-one. The proposed reaction mechanism yielding adducts A3-A6 involves DDE epoxidation at C2, followed by nucleophilic addition of the exocyclic amino group of dGuo to the C1 of the aldehyde and cyclization, via nucleophilic attack, on the C2 epoxy group by N-1. The formation of adducts A1-A6 has been investigated in acidic, neutral, and basic pH in the presence of H2O2 or tent-butyl hydroperoxide. Neutral conditions, in the presence of H2O2, have favored the formation of adducts A1 and A2, with minor amounts of A3-A6, which were prevalent under basic conditions. These data indicate that DDE can modify DNA bases through different oxidative pathways involving its two double bonds. It is important to structurally characterize DNA base derivatives induced by alpha,beta-unsaturated aldehydes so that the genotoxic risks associated with the lipid peroxidation process can be assessed.

Constituintes Químicos de Hyptidendron canum R. Harley (Lamiaceae)

CHEMICAL CONSTITUENTS OF Hyptidendron canum (Pohl ex Benth.) R. Harley (LAMIACEAE). Chemical investigation of Hyptidendron canum stems resulted in the isolation of betulinic, ursolic and euscaphic acids. From the leaves were isolated 3β-O- β-galactopiranosilsitosterol, ursolic aldehyde, and mixtures of maslinic acid and 2α-hydroxyursolic acid, α and β-amyrin, uvaol and erythrodiol, sitosterol and stigmasterol, spathulenol and globulol. Hexane and chloroform leave fractions as well as ursolic and betulinic acids showed antifungal activities against the yeast form of Paracoccidioides brasiliensis.

Produção, imobilização e aplicação de lipase de Fusarium verticillioides

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Mortality of Bemisia tabaci biotype B (sternorrhyncha: aleyrodidae) adults by aliphatic and aromatic synthetic sucrose esters

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Inhibitory Effect of Gallic Acid and Its Esters on 2,2 '-Azobis(2-amidinopropane)hydrochloride (AAPH)-Induced Hemolysis and Depletion of Intracellular Glutathione in Erythrocytes

The protective effect of gallic acid and its esters, methyl, propyl, and lauryl gallate, against 2,2'-azobis(2-amidinopropane)hydrochloride (AAPH)-induced hemolysis and depletion of intracellular glutathione (GSH) in erythrocytes was studied. The inhibition of hemolysis was dose-dependent, and the esters were significantly more effective than gallic acid. Gallic acid and its esters were compared with regard to their reactivity to free radicals, using the DPPH and AAPH/pyranine free-cell assays, and no significant difference was obtained. Gallic acid and its esters not only failed to inhibit the depletion of intracellular GSH in erythrocytes induced by AAPH but exacerbated it. Similarly, the oxidation of GSH by AAPH or horseradish peroxidase/H(2)O(2) in cell-free systems was exacerbated by gallic acid or gallates. This property could be involved in the recent findings on proapoptotic and pro-oxidant activities of gallates in tumor cells. We provide evidence that lipophilicity and not only radical scavenger potency is an important factor regarding the efficiency of antihemolytic substances.

Effects of two estradiol esters (benzoate and cypionate) on the induction of synchronized ovulations in Bos indicus cows submitted to a timed artificial insemination protocol

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Structure Elucidation and Absolute Stereochemistry of Isomeric Monoterpene Chromane Esters

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Suppression of TNF- induced NFB activity by gallic acid and its semi-synthetic esters: possible role in cancer chemoprevention

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)