Occurrence of biflavones in leaves of Caesalpinia pyramidalis specimens

Abstract

Recebido em 17/9/09; aceito em 2/2/10; publicado na web em 18/6/10The chloroform partition of methanol extract of leaves of Caesalpinia pyramidalis was submitted to different chromatographic procedures which afforded besides agathisflavone and taxifolin, the minor biflavones loniflavone, amentoflavone, 5'-hydroxyamentoflavone and podocarpusflavone A. The structures of the compounds were established on the basis of NMR and MS data analysis. Besides, the content of biflavones of different specimens of C. pyramidalis, which are collected in different habitats of the Brazilian semi-arid region, was determinated by LC-APCI-MS analysis. These analysis demonstrated that only the specimens harvested in Bahia state showed collectively the presence of agathisflavone, amentoflavone, sequoiaflavone and podocarpusflavone A.Keywords: Caesalpinia pyramidalis; biflavones; flavonoid analysis. INTRODUCTIONCaesalpinia pyramidalis Tul. is a tree belonging to the family Leguminosae-Caesalpinoideae, which is endemic of Brazilian northeastern, especially in the caatinga. It is popularly known as "catingueira" or "pau-de-rato" and its leaves are used in the preparation of infusions and decocts, which are used by the local population as diuretic, antidispeptic, stomach aches and for fever. 1 Species of this genus are known to present different biological activities. For instance, the extract of seeds of C. bonducella showed antimicrobial activities 2 and they are also employed in the treatment of diabetes. 3 Extracts of C. volkensii and C. pluviosa presents antimalarial activity 4 and C. pulcherrima antiviral activity. 5 The extract of C. pyramidalis is responsible for antibacterial, 6 larvicidal and moluscicidal 7 activities.The presence of diterpenes and flavonoids besides other phenolics is characteristic of this genus as well as the subfamily. 8 From the previous studies regarding with C. pyramidalis were isolated phenylpropanoids, biflavonoids, lignan, flavonoids besides gallic acid. 9 In the present study it was reported the isolation and characterization of the minor biflavonoids loniflavone (1), amentoflavone (2), 5¢-hydroxyamentoflavone (3) and podocarpusflavone A (5), besides agathisflavone (4) and taxifolin (6) from the leaves of C. pyramidalis (Figure 1). It was also evaluated by LC-MS the composition of biflavonoids present in leaves of specimens of C. pyramidalis collected in different habitats of Brazilian semi-arid region. EXPERIMENTAL General proceduresThe NMR spectra were obtained in Varian Gemini 2000, Inova 500 and Bruker AMX500 spectrometers operating at 300 and 500 MHz ( 1 H) and, 75 and 125 MHz ( 13 C), employing CD 3 OD, C 5 D 5 N and (CD 3 ) 2 CO as solvents and TMS as internal standard. The MS and the LC-MS analysis were carried out in a Shimadzu chromatographer mod. Bahia et al. 1298 Quim. Nova LCMS-2310, with autosampler 5 mL loop. The detection of biflavonoids was obtained in positive and negative APCI mode. The chromatograms were obtained using a VP-ODS (RP18 -5 mm; 3.9 x 150 mm) column and as mobile pha...

Antimicrobial activity and bioautographic study of antistaphylococcal components from Caesalpinia pyramidalis Tull.

“…The presence of gallic acid and ellagic acid was also evidenced in the flower extract in methanol . Other components identified were polyphenols (phenolic acid) in the fruit, and ursolic acid and quercetin from the bark of the stem and peel of the root (root and bark of the stem) thus confirming data from the literature (Bahia et al, 2010;Bahia et al, 2005).…”

“…A large number of metabolites have been isolated from `catingueira`, such as: phenylpropanoids, lupeol, β-sitosterol, bioflavonoids (agastiflavone, amentoflavone, sequoiaflavone and podocarpusflavone), chalcone, kaempferol, apigenin, lignane, stigamasterol and methyl gallate (Mendes et al, 2000;Bahia et al, 2010;Novais et al, 2003). Crude ethyl acetate from the leaves and roots of C. pyramidalis Tull.…”

Thermal Degradation Kinetics of Kaempferol and Quercetin in the Pre-Formulated of the Standardized Extracts of Poincianella Pyramidalis (Tul.) L. P. Queiroz Obtained by Spray Dryer

“…L. P. Queiroz is an arboreal species belonging to the family Fabaceae, endemic to the northeastern region of Brazil, mainly in the caatinga biome, popularly known as "catingueira", "pau de porco", "catinga de porco", "pau de rato", "mussilaba" e "catingueira-das-folhas-largas" [1]. It is used in tradicional medicine for the treatment of gastritis, colic, diarrhea, asthma, bronchitis, diabetes, as an expectorant, cicatrizant, antiinflammatory and diuretic [2][3][4][5].…”

Development and Validation of High-Performance Liquid Chromatography With Diode Array Detector Method to Analysis of Kaempferol Marker From Extracts of Poincianella Pyramidalis (Tul) L.P Queiroz

“…Phytochemical investigations showed the presence of terpenes, lignans, tannins, flavonoids, and mainly bioflavonoids [9,10]. The kaempferol was isolated from the chloroformic extract of the leaves of P. pyramidalis, and several studies have demonstrated pharmacological potential of this compound, especially its anti-inflammatory properties [2,11].…”