Prenylated Flavonoids From Roots Of Dahlstedtia Glaziovii (fabaceae)

A phytochemical study of roots of Dahlstedtia glaziovii (Fabaceae) furnished a new dibenzoylmethane (glaziovione), along with eighteen known compounds. Their structures were determined through 1D and 2D nuclear magnetic resonance (NMR) (heteronuclear single quantum coherence, HSQC, and heteronuclear multiple bond correlation, HMBC) and high-resolution mass spectrometry (HRMS) spectral analyses. The antiproliferative activity was investigated for the crude extracts, the dibenzoylmethanes 2'-methoxy-8-(a-a-dimethylallyl)-furano- [4",5":3',4']- dibenzoylmethane, 3,4-methylenedioxy-2'-methoxy-8-(a-a- dimethylallyl)-furano-[4",5":3',4']- dibenzoylmethane and pongamol, and the flavones lanceolatin B, karanjin, pongapin and 3',4'-methylenedioxy-2'', 2''-dimethylpyrano-[5'',6'':8,7]-flavone. The dibenzoylmethanes were more active than the flavones.The extracts were evaluated for their antimicrobial effects, but none was shown to be active. © 2014 Sociedade Brasileira de Química.2569951001Da Silva, M.J., Queiroz, L.P., Tozzi, A.M.G.A., Lewis, G.P., Souza, A.P., (2012) Taxon, 61, p. 93Garcez, F.R., Scramin, S., Do Nascimento, M., Mors, W.B., (1988) Phytochemistry, 27, p. 1079Pietta, P.G., (2000) J. Nat. Prod, 63, p. 1035Shirley, B.W., (1996) Trends Plant Sci, 11, p. 377Guaratini, T., Callejon, D.R., Pires, D.C., Lopes, J.N.C., Lima, L.M., Neto, D.G., Sustovich, C., Lopes, N.P., (2009) Quim. Nova, 32, p. 717Cushnie, T.P.T., Lamb, A.J., (2005) Int. J. Antimicrob. Agents, 26, p. 343Ko, H., Tsao, L.-T., Yu, K.-L., Liu, C.-T., Wang, J.-P., Lin, C.-N., (2003) Bioorg. Med. Chem, 11, p. 105Pan, L., Chai, H., Kinghorn, A.D., (2010) Phytochem. Lett, 3, p. 1Harborne, J.B., Williams, C.A., (2000) Phytochemistry, 55, p. 481Spencer, J.P.E., (2009) Chem. Soc. Rev, 38, p. 1152López, S., Castelli, M., Zacchino, S., Domínguez, J., Lobo, G., Charris-Charris, J., Cortes, G.J.C., Enriz, R.D., (2001) Bioorg. Med. Chem, 9, p. 1999Havsteen, B.H., (2002) Pharmacol. Ther, 96, p. 67Clinical and Laboratory Standards Institute (CLSI document M27-A2, , Método de Referência para Testes de Diluição em Caldo para Determinação da Sensibilidade de Leveduras à Terapia AntifúngicaNorma Aprovada, 2a ed.CLSI: Wayne, PA, 2002Clinical and Laboratory Standards Institute (CLSI document M7-A6, , Metodologia dos Testes de Sensibilidade a Agentes Antimicrobianos por Diluição para Bactéria de Crescimento AeróbicoNorma Aprovada, 6a ed.CLSI: Wayne, PA, 2003Monks, A., Scudeiro, D., Skehan, P., Shoemaker, R., Paull, K., Vistica, D., Hose, C., Boyd, M., (1991) J. Natl. Cancer Inst, 83, p. 757Magalhães, A.F., Tozzi, A.M.G.A., Magalhães, E.G., Blanco, I.S., Nogueira, M.A., (1997) Phytochemistry, 46, p. 1029Talapatra, S.K., Mallik, A.K., Talapatra, B., (1980) Phytochemistry, 19, p. 1199Magalhães, A.F., Tozzi, A.M.G.A., Magalhães, E.G., Sannomiya, M., Soriano, M.D.P.C., Perez, M.A.F., (2007) An. Acad. Bras. Cienc, 79, p. 351Sharma, P., Seshadri, T.R., Mukerjee, S.K., (1973) Indian J. Chem, 11, p. 985Pathak, V.P., Saini, T.R., Khanna, R.N., (1983) Phytochemistry, 22, p. 1303Do Nascimento, M., Mors, W.B., (1972) Phytochemistry, 11, p. 3023Gupta, R.K., Krishnamurti, M., (1976) Phytochemistry, 15, p. 2011Tanaka, T., Iinuma, M., Yuki, K., Fujii, Y., Mizuno, M., (1992) Phytochemistry, 31, p. 993Mahey, S., Sharma, P., Seshadri, T.R., Mukerjee, S.K., (1972) Indian J. Chem, 10, p. 585Khanna, R.N., Seshadri, T.R., (1963) Tetrahedron, 19, p. 219Mukerje, S.K., Sarkar, S.C., Sewadri, T.R., (1969) Tetrahedron, 25, p. 1063Vasconcelos, J.N., Santiago, G.M.P., Lima, J.Q., Mafezoli, J., De Lemos, T.L.G., Da Silva, F.R.L., Lima, M.A.S., Cesarin-Sobrinho, D., (2012) Quim. Nova, 35, p. 1097Magalhães, A.F., Tozzi, A.M.G.A., Sales, B.H.L.N., Magalhães, E.G., (1996) Phytochemistry, 42, p. 1459Magalhães, A.F., Tozzi, A.M.G.A., Magalhães, E.G., Blanco, I.S., Soriano, M.D.P.C., (2004) An. Acad. Bras. Cienc, 76, p. 65

Gas chromatography coupled to mass spectrometry (GC-MS) characterization and evaluation of antibacterial bioactivities of the essential oils from Piper arboreum Aubl., Piper aduncum L. e Piper gaudichaudianum Kunth

The objective of this study was to determine the chemical profile and to evaluate the antibacterial activity of the essential oils of Piper species and modulation of the antibiotic activity, using the microdilution method to determine the minimum inhibitory concentration. The chemical components were characterized by gas chromatography coupled to mass spectrometry, which revealed \u3b2-copaen-4-\u3b1-ol (31.38%), spathulenol (25.92%), and germacrene B (21.53%) as major constituents of the essential oils of Piper arboreum, Piper aduncum, and Piper gaudichaudianum, respectively. The essential oils analyzed in this study did not present a clinically relevant activity against standard and multiresistant Escherichia coli. However, in the case of multiresistant Staphylococcus aureus, there was a significant activity, corroborating with reports in the literature, where Gram-positive bacteria are more susceptible to antimicrobial activity. The essential oils modulated the effect of the antibiotics norfloxacin and gentamicin, having on the latter greater modulating effect; however, for erythromycin, no statistically significant effect was observed. In conclusion, the results obtained in this study demonstrated that the essential oils of the analyzed Piper species present an inhibitory effect against S. aureus and modulate antibiotic activity, most of which presents synergistic activity