Flavonóides glicosilados das folhas e flores de Bauhinia forficata (Leguminosae)

Pizzolatti, Moacir Geraldo; Cunha, Anildo; Szpoganicz, Bruno; Sousa, Eliandra de; Braz-Filho, Raimundo; Schripsema, Jan

doi:10.1590/s0100-40422003000400003

Cited by 80 publications

(54 citation statements)

References 5 publications

(7 reference statements)

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“…and m/z 287 (aglycone) in the MS (relative abundance proportions: 27:39:100, respectively). 1 H and 13 C NMR (400 MHz and 100 MHz respectively, DMSO-d 6 /drops D 2 O) analyses with the help of the correlation on the COSY, HMQC and HMBC spectra and comparison of their spectral data with those already reported, 20,21 confirmed the structure of kaempferol-3,7-O-(α)-dirhamnoside (kaempferitrin) (Figure 1) for this compound.…”

Section: Resultssupporting

confidence: 63%

Kaempferitrin from Uncaria guianensis (Rubiaceae) and its potential as a chemical marker for the species

Valente¹,

Bizarri²,

Liechocki³

et al. 2009

J. Braz. Chem. Soc.

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Uncaria tomentosa (Willd.) DC. e U. guianensis (Aubl.) Gmel., conhecidas como unha-de-gato, são trepadeiras lenhosas nativas das florestas tropicais amazônica e central-americana. As espécies contêm, em diferentes proporções, alcalóides indólicos e oxindólicos, triterpenóides glicosilados, esteróides e proantocianidinas. U. tomentosa é quimicamente identificada pelo perfil e conteúdo de alcalóides oxindólicos, ao passo que U. guianensis não possui um marcador químico efetivo. Nesse trabalho descreve-se o isolamento de canferol-3,7-O-(α)-dirramnosídeo (canferitrina) pela primeira vez em espécies do gênero Uncaria. A triagem para essa substância em folhas, galhos ou cascas das duas espécies por CCD e CLAE-DAD-EM demonstrou a presença de canferitrina apenas nas folhas e galhos de U. guianensis, numa proporção cerca de trinta e seis vezes maior nas folhas do que nos galhos. Estes resultados revelaram a seletividade da U. guianensis em produzir o flavonóide glicosilado, sugerindo esta substância como um marcador químico potencial para a espécie.Uncaria tomentosa (Willd.) DC. and U. guianensis (Aubl.) Gmel., known as cat's claw, are large woody vines native to the Amazonian and Central American rainforests. The species contain, in different proportions, indole and oxindole alkaloids, triterpenoid glycosides, sterols and proanthocyanidins. U. tomentosa can be chemically identified by its oxindole alkaloid profile and content, whereas U. guianensis has no satisfactorily established chemical markers. This work describes, for the first time, the isolation of kaempferol-3,7-O-(α)-dirhamnoside (kaempferitrin) in Uncaria species. Screening for this compound in leaves, stems or bark of both species through TLC and HPLC-DAD-MS showed the presence of kaempferitrin only in the leaves and stems of U. guianensis, at a ratio almost thirty six times greater in the leaves than in the stems. These results reveal the selectivity of U. guianensis to produce this bioactive flavonoid glycoside, and suggest this compound as a potential chemical marker for the species.

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Section: Resultssupporting

confidence: 63%

Kaempferitrin from Uncaria guianensis (Rubiaceae) and its potential as a chemical marker for the species

Valente¹,

Bizarri²,

Liechocki³

et al. 2009

J. Braz. Chem. Soc.

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“…The IR spectrum displayed O-H stretching bands at 3350 cm -1 for 4 and 3375 cm -1 for 5, and conjugated carbonyl group absorptions at 1675 cm -1 and 1667 cm -1 , respectively. The 1 H NMR spectra of compounds 4 and 5 showed two meta-coupled doublets for A-ring, at δ H 6.55 (d, J=2.2 Hz, H-6), 6.13 (d, J=2.2 Hz, H-8) for 4 and 6.35 (d, J=2.0 Hz, H-6), 6.44 (d, J=2.0 Hz, H-8) for 5 and two orto-coupled doublets, for B-ring, at δ H 8.02 (d, J=8.8 Hz, H-2'/6') and 6.99 (d, J=8.8 Hz, H-3'/5') for 4 and 8.08 (d, J=7.9 Hz, H-2'/6'), 7.02 (d, J=7.8 Hz, H-3'/5') for 5, commonly observed in the kaempferol nucleus (Pizzolatti et al, 2003). Also, one signal for a chelated hydroxyl (OH-5) was observed at δ H 12.76 for 4 and 12.53 for 5.…”

Section: Resultsmentioning

confidence: 94%

Chemical constituents from three medicinal plants: Piper renitens, Siparuna guianensis and Alternanthera brasiliana

Facundo¹,

Azevedo²,

Rodrigues³

et al. 2012

Rev. bras. farmacogn.

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Chemical study of three medicinal plants: from leaves of Piper renitens (Miq.) Yunck, Piperaceae, and Siparuna guianensis Aubl., Siparunaceae, and from flowers of Alternanthera brasiliana (L.) Kuntze, Amaranthaceae, resulted in isolation of nine compounds: three steroids, β-sitosterol, stigmasterol from P. renitens and sitosterol-3-O-β-D-glucopyranoside from A. brasiliana, the diterpene kaurane ent-kauran-16α,17-diol from P. renitens, two derivatives kaempferolmethylether, kumatakenine (kaempferol-3,7-dimethylether) and kaempferol-3,7,3'-trimethylether from S. guianensis and three flavones, crysoeriol (5,7,4'-trihydroxy-3'-methoxyflavone), tricin (5,7,4'-trihydroxy-3',5'-dimethoxyflavone) and 7-O-β-D-glucopyranoside-5,4'-dihydroxy-3'-methoxyflavone from A. brasiliana. Compounds structures were determinate using 1D and 2D 1 H NMR and 13 C spectral data, mass and IR spectra, comparing with literature data.

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“…The signals in C 158.66 and C 135.63 were attributed, after comparison with literature (Pizzolatti et al, 2003;Rastrelli et al, 1995), to the carbons C-2 and C-3 respectively, fact that strengthened the suggestion of 1 being a fl avone. ' .…”

Section: Structure Determination Ofmentioning

confidence: 54%

“…The characterization and the location of the diglucoside unit (rutinoside) in C-3 was based on the following observations: a) the chemical shift of C-2 ( C 158.99), revealed by the 13 C NMR spectrum, suggested the presence of glycoside in C-3; b) the long-distance correlation between the glucose anomeric hydrogen H-1 '' ( H 5.23,d,J=7.8 Hz) and the carbon C-3 ( C 133.53; 3 J CH ), observed in the HMBC spectrum, permitted to defi ne the bond -O rutinoside; c) the chemical shift of the glucose methylene carbon ( C 67.56) permitted the location of the rhamnose unit in this carbon atom, since the signal of hydroxymethylene group free of a glycoside unit appears around C 62.12 (Pizzolatti et al, 2003); d) the HMBC spectrum revealed the correlation between the rhamnose anomeric hydrogen H-1 ''' ( H 4.54, d, J=1.1) and the glucose methylene carbon C-6 '' . Through the two-bond correlations ( 2 J CH ) of H-6 ( H 6.21) with C-7 ( C 166.51) and H-6 ( H 6.21) with C-5 ( C 163.15) it was possible to determine that C-5 and C-7 sustain hydroxyl.…”

Section: Structure Determination Ofmentioning

confidence: 99%

Secondary metabolites isolated from Richardia brasiliensis Gomes (Rubiaceae)

Pinto¹,

Tomaz²,

Tavares³

et al. 2008

Rev. bras. farmacogn.

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RESUMO: "Metabólitos secundários isolados de Richardia brasiliensis Gomes (Rubiaceae)".A família Rubiaceae compreende cerca de 637 gêneros e aproximadamente 10700 espécies, ocorrendo essencialmente nas regiões tropicais do Brasil. Richardia brasiliensis Gomes, popularmente conhecida por "poaia branca", é uma planta nativa da região sul do Brasil, utilizada na medicina popular como anti-emética e no tratamento de diabetes. Este trabalho reporta o isolamento e identifi cação estrutural de um fl avonóide glicosilado, um triterpeno, uma cumarina e dois derivados de ácido benzóico, objetivando contribuir para quimiotaxonomia do gênero Richardia. Através deste estudo foi possível isolar e identifi car os metabólitos isorametina-3-O-rutinosídeo, ácido oleanólico, a cumarina escopoletina e os ácidos p-hidroxibenzóico e m-metoxi-p-hidroxi-benzóico, todos isolados pela primeira vez no gênero, exceto o último, apresentando, portanto, relevante importância quimiotaxonômica para o mesmo. As estruturas foram identifi cadas com o uso de técnicas espectroscópicas de IV, RMN 1 H e 13 C uni e bidimensionais e comparação com dados da literatura.Unitermos: Rubiaceae, Richardia brasiliensis, isorametina-3-O-rutinosídeo, ácido oleanólico, escopoletina. ABSTRACT:The family Rubiaceae comprises around 637 genera and approximately 10,700 species, occurring essentially in tropical regions of Brazil. Richardia brasiliensis Gomes, known popularly as "poaia branca", is native to Brazil south region, used in folk medicine as anti-emetic and in the treatment of diabetes. This work reports the isolation and structural identifi cation of a fl avonoid glycoside, a triterpene, a coumarin and two benzoic acid derivatives, aiming at contributing to the chemotaxonomy of the genus Richardia, through a phytochemical study of Richardia brasiliensis. By means of this study the metabolites isorhamnetin-3-O-rutinoside, oleanolic acid, the coumarin scopoletin and p-hydroxy-benzoic and m-methoxy-p-hydroxybenzoic acids were isolated and identifi ed. All of them, but the latter, were isolated for the fi rst time in the genus, thereby presenting relevant chemotaxonomic importance to it. The structures were identifi ed using spectroscopic techniques such as IR, one and two-dimensional 1 H and 13 C NMR besides comparison with literature data.

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Flavonóides glicosilados das folhas e flores de Bauhinia forficata (Leguminosae)

Abstract: Recebido em 5/4/02; aceito em 6/2/03 FLAVONOIDS GLYCOSIDES FROM LEAVES AND FLOWERS OF Bauhinia forficata (LEGUMINOSAE). From the leaves of Bauhinia forficata kaempferol and four flavonoid glycosides, 3,

Cited by 80 publications

References 5 publications

Kaempferitrin from Uncaria guianensis (Rubiaceae) and its potential as a chemical marker for the species

Kaempferitrin from Uncaria guianensis (Rubiaceae) and its potential as a chemical marker for the species

Chemical constituents from three medicinal plants: Piper renitens, Siparuna guianensis and Alternanthera brasiliana

Secondary metabolites isolated from Richardia brasiliensis Gomes (Rubiaceae)

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