Caesalpinioflavone, a New Cytotoxic Biflavonoid Isolated from Caesalpinia pluviosa var ...

Caesalpinioflavone, a New Cytotoxic Biflavonoid Isolated from Caesalpinia pluviosa var ...

6 Pages · 2015 · 438 KB · English

After attachment (24 h), the cells were treated for 48 h with caesalpinioflavone at different concentrations (5 - 160 µmol L-1). The Promega non- radioactive cell proliferation assay was used to determinate .. through grants and subsidies. References. 1. Srinivas, K. V. N. S.; Rao, Y. K.; Das, I.

Caesalpinioflavone, a New Cytotoxic Biflavonoid Isolated from Caesalpinia pluviosa var ... free download

J Braz Chem Soc , Vol 26, No 4, 804809, 2015 Printed in Brazil ©2015 Sociedade Brasileira de Química0103 5053 $600+000 *email: [email protected] Caesalpinioflavone, a New Cytotoxic Biflavonoid Isolated from Caesalpinia pluviosa var peltophoroides João L B Zanin, a Murilo Massoni, a Marcelo H dos Santos, a Giovana C de Freitas, b Evandro L O Niero, c Renata R Schefer, b João H G Lago, d Marisa Ionta e and Marisi G Soares* ,a aInstituto de Química and eInstituto de Ciências Biomédicas, Universidade Federal de Alfenas, 37130000 AlfenasMG, Brazil bInstituto de Química and cInstituto de Ciências Biomédicas, Universidade de São Paulo, 05508000 São PauloSP, Brazil dInstituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, 09920000 São PauloSP, Brazil The present study aimed to investigate the presence of compounds with antitumor activity in the plant Caesalpinia pluviosa var peltophoroides From bioactivity guided studies it was possible to isolate a new biflavonoid, named caesalpinioflavone, whose chemical structure was determined by spectroscopic ( 1H and 13C nucler magnetic ressonace, homonuclear correlation spectroscopy and heteronuclear multiplebond correlation spectroscopy) and spectrometric (high resolution electrospray ionization mass) methods According to in vitro assays, caesalpinioflavone was effective in reducing the cell viability of tumor cell lines A549, MCF7, Hst578T and HTC This effect was consequent of cell cycle arrest in G1/S transition (A549 and MCF7) and cytotoxic activity (Hs578T and HTC) Taken together, these data indicate that caesalpinioflavone has a promising antitumor activity Keywords: Caesalpinia pluviosa var peltophoroides , biflavonoid, antiproliferative activity, cancer Introduction Caesalpinia L is a genus of Fabaceae plants belonging to the Caesalpinioideae subfamily, which is found in tropical and subtropical zones, and includes about 500 species, most of which have not been investigated in relation to their chemical compositions and biological properties Caesalpinia pulcherrima presents emmenagogue and abortifacient effects, 1 Caesalpinia bonduc (L) Roxb displays anthelmintic, anticancer and antimalarial properties, 2 and Caesalpinia sappan has been used as an antiinflammatory agent 24 In addition, it has been described that sappanchalcone, extracted from C sappan, suppresses oral cancer cell growth and induces apoptosis in oral squamous cell carcinoma 5 Several classes of natural compounds have been isolated from the Caesalpinia genus, including flavonoids, diterpenes, steroids, organic acids and sugars 6 Additionally, hydrolysable tannins were isolated from Caesalpinia pluviosa (synonym Poincianella pluviosa )7 Considering that Caesalpinia represents a valuable source for identifying new chemical compounds with therapeutic potential, in this meaning, this study aimed the identification of cytotoxic compounds from the stem bark methanol extract of Caesalpinia pluviosa var peltophoroides using a bioguided fractionation procedure Experimental General All solvents and reagents used were analytically pure Silica gel (Merck, 230400 mesh) and sephadex LH20 (SigmaAldrich) were used for column chromatographic (CC) separations while silica gel plates (025 mm) 60 PF 254 (Merck) were used for analytical thin layer Article A http://dxdoiorg/105935/0103505320150043 805 chromatography (TLC) Plates were revealed using iodine vapor, vanillinH 2SO 4 (3%), 1% FeCl 3 in ethanol or using ultraviolet radiation ( λ = 254 and 356 nm) Ultraviolet (UV) measurements were performed using an UVspectrophotometer model UVvis2550 (Shimadzu) Melting point was determined using a PFM II Aaker apparatus Infrared (IR) spectrum was obtained on Shimadzu IRPrestig21 and manipulated with the software IRSolution 1H (500 MHz) and 13C (125 MHz) nuclear magnetic resonance (NMR) spectra were recorded on a Bruker 500 MHz apparatus DRX spectrometer (Bruker BioSpin, Germany) using CD 3OD as solvent High resolution electrospray ionization mass (HRESIMS) was obtained using a Bruker MicroTOF II spectrometer (Bruker Daltonics, Germany) in negative mode Optical rotation measurement was recorded at 25 °C on a Perkin Elmer model 343 polarimeter High pressure liquid chromatography (HPLC) chromatograms were obtained on a UFLC Shimadzu 20 A, with a diode array detector (DAD) and a VPODS (Shimadzu) C18 column (150 × 46 mm, 5 mm particle size) Plant

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