Astragenol-3-O-β-D-xylopyranoside, an unusual triterpene type from Ouratea turnarea (Ochnaceae).

Some phytochemical investigations were carried on the roots of Ouratea turnarea. This work led to the isolation of menisdaurin, epicatechin, β-sitosterol-3-O-β-D-glucopyranoside and astragenol-3-O-β-D-xylopyranoside, the last compound is reported for the first time from the Ochnaceae family. Their structures were established by direct interpretation of their spectral data, mainly HRESI-MS, 1D and 2D NMR, and by comparison with literature.

Antifungal Activity of extracts from two Ouratea species on Candida albicans.

Plants are invaluable sources of pharmaceutical products and Brazil, in particular, has yielded an incredible array of plant and animal products that have drawn the attention of ethnopharmacologists from around the world. Ouratea is a genus of tropical plants within the Ochnaceae. Ouratea is widespread throughtout the tropics, with species in Costa Rica, Brazil, Jamaica, and Kenya. The search for compounds with antimicrobial activity is urgent and indispensable for the treatment of infectious diseases caused by microorganisms resistant to traditional antimicrobial drugs. A screening was conducted with organic extracts from two species, from roots and leaves of Ouratea hexasperma var. planchonii Engl. and leaves and branches of Ouratea parviflora Engl., to identify plant extracts with antifungal properties against Candida albicans. Initially, minimal inhibitory concentrations (MICs) were determined in C. albicans cellular suspension in Sabouraud medium, in a range of 0.060-3.0 mg/ml. Fractions OHRMWE (Ethyl acetate fraction) and OHLMWB (Buthanol fraction) obtained by solvents partition of methanol:water extract from Ouratea hexasperma with ethyl acetate from the roots and n-butanol from the leaves, respectively, showed a higher antifungal activity. The antifungal activity of these extracts was also compared in growth delay of C. albicans cultures.

Structure determination of betulinic acid from the leaves of Lophira lanceolata Van Tiegh. Ex Keay (Ochnaceae).

Cupressuflavone a biflavone was ealier isolated from the leaves of Lophira lanceolata. From this work Betulinic acid was also isolate from the leaves for the first time. The two compounds were identified on the basis of 1D NMR (1H, 13C and DEPT), 2D NMR (COSY, HSQC, HMBC and NOESY), IR, MS data and by comparison with reported data. Like that of Ouretia this recent isolation suggest that betulinic acid can be used as chemical markers in the Ochnaceae family.

Biflavones and triterpenoids isolated from Ouratea castaneifolia (DC.) Engl., Ochnaceae / Biflavonas e triterpenóides isolados de Ouratea castaneifolia (DC.) Engl., Ochnaceae

This paper presents the chemical investigation of the leaves and stems of Ouratea castaneifolia (DC.) Engl.. There are no chemical or pharmacological studies with this species. Classic phytochemical investigation of the organic extracts together with high pressure liquid chromatography (HPLC) procedures lead to the identification of seventeen metabolites: seven triterpenes (friedelin, 3β-friedelinol, α-amyrin, β-amyrin, lupeol, germanicol and taraxerol), four steroids (sitosterol, stigmasterol and the glycosides sitosteryl 3-O-β-D-glucopyranoside and stigmasteryl 3-O-β-D-glucopyranoside), one isoflavone (5,7,4'-trimethoxyisoflavone), one flavone (5,4'-dihydroxy-7,3',5'-trimethoxyflavone) and four biflavones (amenthoflavone, 7,7"-O-dimethylamenthoflavone, heveaflavone and tetramethylamenthoflavone). The structures of the compounds were established by the analysis of ¹H, 13C NMR spectra including bidimensional techniques. The classes of the identified metabolites are in agreement with previous studies of the Ouratea genus.

O presente trabalho trata da investigação química das folhas e caule da espécie Ouratea castaneifolia (DC.) Engl., sobre a qual não há registros de estudos químicos ou farmacológicos anteriores. O estudo fitoquímico clássico dos extratos orgânicos do caule e das folhas de O. castaneifolia foi aliado à técnica da cromatografia líquida de alta eficiência (CLAE) e resultou na identificação de dezessete metabólitos: sete triperpenos (friedelina, 3β-friedelinol, α-amirina, β-amirina, lupeol, taraxerol e germanicol), quatro esteróides (sitosterol, estigmasterol e os glucosídeos sitosteril 3-O-β-D-glicopiranosídeo e estigmasteril 3-O-β-D-glicopiranosídeo), uma isoflavona (5,7,4´-trimetoxiisoflavona), uma flavona (5,4´-diidroxi-7,3´,5´-trimetoxiflavona), quatro biflavonas (amentoflavona, 7,7"-O-dimetil-amentoflavona, heveaflavona e tetrametilamentoflavona). A identificação das substâncias foi feita com base na análise de espectros de RMN de ¹H, 13C e técnicas bidimensionais. As classes dos metabólitos identificados estão de acordo com aquelas citadas em estudos químicos do gênero Ouratea.

A new derivative of dihydroochnaflavone isolated from Luxemburgia species (Ochnaceae) and the complete ¹H and 13C NMR chemical shifts assignments / Um novo derivado da dihidroochnaflavona isolada de Luxemburgia species (Ochnaceae) e o completo assinalamento dos dados de RMN de ¹H e 13C

The biflavonoid 2",3"-dihydroochnaflavone, isolated from the Luxemburgia species (Ochanaceae), was treated with diazomethane to obtain the trimethyl-ether that was treated with pyridine/acetic anhydride to yield a new derivative, 5-acetil-7,4'-dimethyl-flavone-(3'→O-4'")-5"-acetil-7"-methyl-flavanone. The complete ¹H and 13C NMR data assignments of the new derivative were made by the one- and two-dimensional spectral analysis.

O biflavonóide 2",3"-diidroochnaflavona, isolada de espécies de Luxemburgia (Ochanaceae), foi tratada com diazometano e forneceu o éter trimetílico que, em seguida, foi tratado com anidrido acético/piridina obtendo-se um novo derivado, 5-acetil-7,4'-dimetil-flavona-(3'→O-4'")-5"-acetil-7"-metil-flavanona. Fez-se o completo assinalamento dos dados de RMN ¹H e 13C através da análise dos espectros uni- e bidimensionais do derivado.

Bioactive flavone dimers from Ouratea multiflora (Ochnaceae)

Chromatographic fractionation of the organic extract from leaves of Ouratea multiflora afforded the flavone dimers heveaflavone, amentoflavone-7'',4''''-dimethyl eter, podocarpusflavone-A and amentoflavone. Their structures were elucidated from spectral data, including 2D-NMR experiments of the natural substances. Biological activities of all isolates were evaluated, using antimicrobial assay against Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis, cytotoxicity assay against mouse lymphoma (L5178) and KB cell lines, TLC screening for acetylcholinesterase inhibitors and antioxidant activity measured by DPPH test.

O fracionamento cromatográfico do extrato orgânico das folhas de Ouratea multiflora forneceu os flavonóides diméricos, heveaflavona, 7'',4''''-dimetilamentoflavona, podocarpusflavona-A e amentoflavona. Suas estruturas foram elucidadas com base nos dados espectrais, incluindo experimentos bidimensionais de RMN, das substâncias naturais. A atividade antibiótica de todos os isolados foi avaliada, usando-se as bacterias Gram-positivas Staphylococcus aureus and Bacillus subtilis. Teste de citotoxicidade nas linhagens de linfoma de ratos (L5178) e KB também foram conduzidos para avaliar os extratos e os flavonóides isolados. a triagem biológica para a avaliação de atividade antioxidante e inibidora de acetil colinesterase foram conduzidas pela técnica da bioautografia com DPPH e teste pelo teste de Ellman respectivamente.

Ochnaceae endémicas del Perú

Esta es una de las familias que constituye una novedad para la flora endémica peruana. La familia Ochnaceae es reconocida en el Perú por presentar siete géneros y 25 especies (Brako & Zarucchi, 1993; Ulloa Ulloa et al., 2004), la mayoría arbustos y árboles. En este trabajo reconocemos tres especies endémicas en dos géneros. Las especies endémicas se encuentran en las regiones Bosques Muy Húmedos Premontanos y Bosques Húmedos Amazónicos, entre los 260 y 1380 m de altitud. Dos de las especies endémicas se encuentran dentro del Sistema Nacional de Áreas Naturales Protegidas por el Estado.

This family is one of the novelties for the Peruvian endemic flora. The Ochnaceae are represented in Peru by seven genera and 25 species (Brako & Zarucchi, 1993; Ulloa Ulloa et al., 2004), mostly shrubs and trees. Here we recognize three endemic species in two genera. These species grow in Humid Lowland Amazonian Forests and Very Humid Premontane Forests regions, between 260 and 1380 m elevation. Two species have been recorded in the Peruvian System of Protected Natural Areas.

Taxonomic studies on Philacra Dwyer (Ochnaceae) - DOI: 10.4025/actascibiolsci.v28i3.191 / Estudos taxonômicos em Philacra Dwyer (Ochnaceae) - DOI: 10.4025/actascibiolsci.v28i3.191

The species of Philacra are found mainly at the Brazil-Venezuela border. Among other Ochnaceae genera, this is the most closely related to Luxemburgia, which occurs only in Brazil, especially at the Espinhaço Range. The taxonomic analysis of Philacra species was based on the type material and herbarium specimens. This work aimed to redescribe the genus, to prepare a taxonomic key and to redescribe the species. The genus redescription and the geographical distribution, a key to the species and species redescription, are presented. Currently, four Philacra species are recognized: P. auriculata Dwyer, P. duidae (Gleason) Dwyer, P. longifolia (Gleason) Dwyer, and P. steyermarkii Maguire.

As espécies de Philacra são encontradas principalmente na fronteira Brasil- Venezuela, e dentre outros gêneros de Ochnaceae, é o mais próximo a Luxemburgia, cujas espécies ocorrem somente no Brasil, especialmente na Cadeia do Espinhaço. A análise taxonômica das espécies de Philacra foi realizada com base no material tipo e em espécimes depositados em herbários. O trabalho objetivou a redescrição do gênero, a elaboração da chave taxonômica e a redescrição das espécies. É apresentada a redescrição do gênero, sua distribuição geográfica, a chave de identificação e a redescrição das espécies. Atualmente, são reconhecidas quatro espécies de Philacra: P. auriculata Dwyer, P. duidae (Gleason) Dwyer, P. longifolia (Gleason) Dwyer e, P. steyermarkii Maguire.

Constituintes químicos e avaliação preliminar in vivo da atividade antimalárica de Ouratea nitida Aubl (Ochnaceae) / Chemical constituents and in vivo preliminary evaluation of antimalarial activity of Ouratea nitida Aubl. (Ochnaceae)

O presente trabalho descreve o isolamento de triterpenos (ácido 3,4-seco-friedelan-3-óico, friedelina e b-amirina) e outros compostos (éster etílico do ácido p-hidroxibenzóico e tetracosano), bem como a avaliação preliminar in vivo da atividade antimalárica de extratos das folhas de Ouratea nitida Aubl. Análise qualitativa através de CG-EM de uma fração apolar do extrato em hexano também foi efetuada. Ésteres metílicos e etílicos dos ácidos laúrico, mirístico, palmítico, esteárico e oléico, metílicos dos ácidos pentadecanóico, heptadecanóico, araquidônico, behênico e lignocérico e o etílico do ácido linoléico foram os componentes majoritários; enquanto que o estearato de n-butila, o tetracosano e a 6,10,14-trimetil-2-pentadecanona foram os minoritários. Os compostos isolados foram identificados com base na análise dos dados espectrais (IV, EM e RMN, incluindo DEPT) e estão sendo descritos pela primeira vez nesta espécie.

This work describes the isolation of triterpenes (3,4-seco-friedelan-3-oic acid, friedelin, and b-amyrin) and other compounds (p-hydroxybenzoic acid ethyl ester and tetracosane) as well as a preliminary evaluation of in vivo antimalarial activity of the extracts from the leaves of Ouratea nitida Aubl. Qualitative analysis by GC-MS of an apolar fraction from the hexane extract was also carried out. Methyl and ethyl esters of lauric, myristic, palmitic, stearic and oleic acids, methyl ester of pentadecanoic, heptadecanoic, arachidonic, beenic and lignoceric acids, and ethyl ester of linoleic acid were found to be the main constituents while n-butyl stearate, tetracosane and 6,10,14-trimetthyl-2-pentadecanone were the minor. All isolated compounds were identified on basis of the spectral data (IR, MS and NMR, including DEPT) and are being described for the first time in this specie.