Jorge M. David

Fatty Acid Esters of Triterpenes from Erythroxylum passerinum

O extrato hexânico das folhas de Erythroxylum passerinum alem de sitosterol, β-amirina, lupeol e eritrodiol, forneceu palmitato de β-amirina, palmitato de 3β,28-diidroxi-olean-12-enila (eritrodiol); palmitato de 3β,11β-diidroxi-olean-12-enila; palmitato de 3β-hidroxi-11-oxo-olean-12-enila e palmitato de 3β-hidroxi-11,12-epoxi-friedoolean-14-enila. As estruturas das substâncias foram estabelecidas atraves da analise dos seus dados espectrometricos, bem como de seus derivados transesterificados, utilizando-se tecnicas de RMN de 1H e de 13C, infravermelho e espectrometria de massas.

Antinociceptive Properties of Bergenin

Bergenin (1) is a C-glucoside of 4-O-methylgallic acid with known antiarthritic activity attributed to modulation of cytokine production. The present study was undertaken to evaluate whether 1 has antinociceptive properties in models of inflammatory pain and to investigate its possible mechanisms of action. Pretreatment with 1 (12.5-100 mg/kg, ip) produced a dose-related inhibition of acetic acid-induced writhing in mice. Furthermore, treatment with 1 (50 and 100 mg/kg) inhibited both the early and late phases in a formalin test. In addition, 1 (50 and 100 mg/kg, ip) inhibited mechanical hyperalgesia, edema, and paw production of hyperalgesic cytokines (TNF-α and IL-1β) induced by complete Freunds adjuvant. However, the local production of IL-10, an anti-inflammatory cytokine, was not altered by 1 (100 mg/kg, ip). Treatment with 1 produced a similar profile of antinociception in wild-type and IL-10-deficient mice. Mice treated with 1 did not show any motor performance alterations or apparent systemic toxicity. The results presented herein demonstrate that bergenin has consistent antinociceptive and anti-inflammatory properties, acting by the inhibition of IL-1β and TNF-α production, and suggest its potential for the control of inflammatory pain.

Triterpenes esterified with fatty acid and triterpene acids isolated from Byrsonima microphylla

The hexane extract of leaves of B. microphylla afforded a mixture of triterpenes esterified with fatty acids. Analyses of spectral data of the mixture and of the derivatives obtained by a transesterification reaction with NaOMe/MeOH permitted to identify the composition of the mixtures as being 24-hydroxy-urs-12-enyl 3b-eicosanate, estearate and palmitate as well as of the 24-hydroxy-olean-12-enyl 3b-eicosanate, estearate and palmitate. From the choroform and ethyl acetate extracts were isolated the oleanolic and 3b,24-dihydroxy-urs-12-en-28-oic acids, quercetin and methyl galic ester, respectively. The compounds were identified through analysis of their spectral data.

Bioactive Oleanane, Lupane and Ursane Triterpene Acid Derivatives

Betulinic, ursolic and oleanolic acids isolated from the aerial parts of Eriope blanchetii (Lamiaceae) were subjected to different esterification reactions, yielding 12 C-3 position ester derivatives. All compounds were identified using spectroscopic techniques, such as IR, 1H-NMR and MS. The derivatives were further investigated for their antioxidant level, Artemia salina lethality and antimicrobial activity.

Biflavonoids and other phenolics from Caesalpinia pyramidalis (Fabaceae)

The chloroform extract of the leaves of Caesalpinia pyramidalis (Caesalpinioidea, Fabaceae) yielded the new biflavonoid named caesalflavone, as well as podocarpusflavone A, agathisflavone, apigenin and kaempferol. The chloroform extract of the trunk wood gave 4,4-dihydroxy-2-methoxychalcone, (-)-syringaresinol, and methyl gallate. Biflavonoids were not found in trunk wood. Until now, C. pyramidalis is the first species in the genus to present biflavonoids. The structural elucidation of the isolated compounds and their derivatives were based on MS, IR, UV, 1D and 2D NMR spectral analyses.

Neolignans from bark and leaves of Ocotea porosa

Abstract Among the 35 neolignans isolated from bark and leaves of Ocotea porosa , 20 (including eight new compounds) belong to 12 benzofuranoid types, 11 (including six new compounds) belong to eight bicyclo[3.2.1]octanoid types and four (including one new compound) belong to four 1,2-diaryl- and 1-aryl-2-cyclohexylpropanoid types. All compounds are considered to originate through oxidative coupling of isoeugenol and eugenol and, in some relatively rare cases, of two isoeugenol units.

Determination of Flavanones in Orange Juices Obtained from Different Sources by HPLC/DAD

Flavanones (hesperidin, naringenin, naringin, and poncirin) in industrial, hand-squeezed orange juices and from fresh-in-squeeze machines orange juices were determined by HPLC/DAD analysis using a previously described liquid-liquid extraction method. Method validation including the accuracy was performed by using recovery tests. Samples (36) collected from different Brazilian locations and brands were analyzed. Concentrations were determined using an external standard curve. The limits of detection (LOD) and the limits of quantification (LOQ) calculated were 0.0037, 1.87, 0.0147, and 0.0066u2009mg 100u2009g−1 and 0.0089, 7.84, 0.0302, and 0.0200u2009mg 100u2009g−1 for naringin, hesperidin, poncirin, and naringenin, respectively. The results demonstrated that hesperidin was present at the highest concentration levels, especially in the industrial orange juices. Its average content and concentration range were 69.85 and 18.80–139.00u2009mg 100u2009g−1. The other flavanones showed the lowest concentration levels. The average contents and concentration ranges found were 0.019, 0.01–0.30, and 0.12 and 0.1–0.17, 0.13, and 0.01–0.36u2009mg 100u2009g−1, respectively. The results were also evaluated using the principal component analysis (PCA) multivariate analysis technique which showed that poncirin, naringenin, and naringin were the principal elements that contributed to the variability in the sample concentrations.

Coumarins from Kielmeyera reticulata

Abstract Five new prenylated 4-phenylcoumarins were isolated from the hexane extract of the stems of Kielmeyera reticulata , 7-hydroxy-8-(4-cinnamoyl-3-methyl-1-oxobutyl)-4-phenyl-2′,2′-dimethyl 2H,6H-benzo[1,2-b:3,4-b′]-dipyran-2-one, 7-hydroxy-8-(4-hydroxy-3-methyl-1-oxobutyl)-4-phenyl-2′,2′-dimethyl-2H,6H-benzo [1,2-b:3,4-b′]-dipyran-2-one, 5-hydroxy-6-(4-cinnamoyl-3-methyl-1-oxobutyl)-4-phenyl-2′,2′-dimethyl-2H,6H-benzo [1,2-b:3,4-b′]-dipyran-2-one, 5,7-dihydroxy-6-(4-cinnamoyl-3-methyl-1-oxobutyl)-8-(3-methyl-2-butenyl)-4-phenyl-2H-1-benzopyran-2-one, and 5,7-dihydroxy-6-(4-hydroxy-3-methyl-1-oxobutyl)-8-(3-methyl-2-butenyl)-4-phenyl-2H-1-benzopyran-2-one, These compounds were identified from spectral evidence and compared with literature data.

Mikania glomerata: Phytochemical, Pharmacological, and Neurochemical Study

The present study primarily aims to identify the relative density and the fatty acids (methyl esters) content present in the standardized ethanol extract of leaves of M. glomerata (EPMG). Meanwhile, in a second moment, this study evaluated the effects of the EPMG on the levels of amino acids in the hippocampus, and the mechanism of sedative and anxiolytic action. Adult mice were treated with doses of 200, 300, and 400u2009mg/kg and evaluated in open field, elevated plus-maze, light dark, and rotarod tests. Moreover, in the behavioral tests diazepam (GABAergic anxiolytic, 2u2009mg/kg) as positive control and flumazenil (GABA antagonist, 2.5u2009mg/kg) were used to identify mechanism of sedative and anxiolytic action produced by EPMG. The EPMG is constituted by the following compounds: methyl cinnamate, 2H-1-benzopyran-2-one, (2-hydroxyphenyl)methyl propionate, (Z)-methyl-hexadec-7-enoate, methyl hexadecanoate, hexadecanoic acid, (Z)-methyl-octadec-9-enoate, octadecanoic acid, and squalene. This extract demonstrated anxiolytic effects, which may be mediated by GABAergic system, and was able to increase GABA levels and reduce of glutamate and aspartate concentrations in mice hippocampus, which can directly and/or indirectly assist in their anxiolytic effect. Although more studies are needed, the EPMG could represent an interesting therapeutical strategy in the treatment of anxiety.

Phenylpropanoid-catechins from bark of Ocotea porosa

Abstract In the bark of Ocotea porosa neolignans are accompanied by the sesquiterpenoid (+)-oplopanone, the flavonoid (−)-epicatechin and two novel compounds, the 4β- and 4α-forms of epicatechin-(7,8-bc)-4 (hydroxyphenyl)- dihydro-2(3H)-pyranone.