Artículos de revistas
Anacardic Acid Derivatives From Brazilian Propolis And Their Antibacterial Activity
Registro en:
Ecletica Quimica. , v. 33, n. 3, p. 53 - 58, 2008.
1004670
10.1590/S0100-46702008000300008
2-s2.0-55849132173
Autor
Silva M.S.S.
De Lima S.G.
Oliveira E.H.
Lopes J.A.D.
Chaves M.H.
Reis F.A.M.
Cito A.M.G.L.
Institución
Resumen
Propolis is a sticky, gummy, resinous substance collected by honeybees (Apis mellifera L.) from various plant sources, which has excellent medicinal properties. This paper describes the isolation and identification of triterpenoids and anacardic acid derivatives from Brazilian propolis and their antibacterial activity. Their structures were elucidated by 1H and 13C NMR, including uni- and bidimensional techniques; in addition, comparisons were made with data from academic literature. These compounds were identified as: cardanols (1a + 1b), cardols (2a + 2b), monoene anacardic acid (3), α-amirine (4), β-amirine (5), cycloartenol (6), 24-methylene- cycloartenol (7) and lupeol (8). The determination of the position of the double bond after a reaction with Dimethyl disulfide (DMDS) is described for the phenol derivatives. The ethanolic extract was tested in vitro for antimicrobial activity by using the disc diffusion method and it showed significant results against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Shigella spp. 33 3 53 58 Ghisalbert, E.L., (1979) Bee World, 60, p. 59 Garcia-Viguera, C., Greenaway, W., Watley, F.R., (1992) Z. Naturforsch, 47 c, p. 634. , Tubigen Usia, T., Banskota, A.H., Tezuka, Y., Midorikawa, K., Matsushige, K., Kadota, S., (2002) J. Nat. Prod, 65, p. 673 Marcucci, M.C., (1995) Apidologie, 26, p. 83 Burdock, G.A., (1998) Food Chem. Toxicol, 36, p. 347 Banskota, A.H., Nagaoka, T., Sumioka, L.Y., Tezuka, Y., Awale, S., Midorikawa, K., Matsushige, K., Kadota, S.J., (2002) Ethnopharmacology, 80, p. 67 Bankova, V.S., Diulgerov, A., Popov, S.S.S., Evstatieva, L., Kuleva, L., Pureb, O., Zamjasan, Z., (1992) Apidologie, 23, p. 79 Bankova, V., Castro, S.L., Marcucci, M.C., (2000) Apidologie, 31, p. 3 Pereira, A.S., Nascimento, E.A., Aquino Neto, F.R., (2002) Z. Naturforsch, 57 c, p. 721 Silva, M.S.S., Citó, A.M.G.L., Chaves, M.H., Lopes, J.A.D., (2005) Quím. Nova, 28, p. 801 De Lima, S.G., (2005) Síntese e Identificação de Biomarcadores em Óleos da Bacia de Campos e Bacia Potiguar: Identificação de 3-alquil-esteranos, , Tese de Doutorado. Unicamp, Instituto de Química, Campinas-SP, Brasil, 350p Wang, C., (1998) The role of lipids in disease resistance and fruit ripening tomato, , Ph.D. Thesis. Rutgers University, New Brunswick, N.J FRANCIS, G.W., VELAND, K., (1981) J. Chromatogr, 219, pp. 379-384 Lizhi Zhu. Investigating The Biosynthesis Of Polyacetylenes: Synthesis of Deuterated Linoleic Acids & Mechanism Studies of DMDS Addition to 1,4-Enynes. Ph.D. Thesis. Miami University-The Graduate School, Usa. Oxford, Ohio, 2003, 104pMurray, P.R., Drew, W.L., Kobayasai, G.S., Thompson, J.R., (1990) Microbiologia Médica, , Guanabara Koogan, Rio de Janeiro Roque, N.F., Olea, R.S.G., (1990) Quim. Nova, 13, p. 278 Mahato, S.B., Kundu, A.P., (1994) Phytochemistry, 37, p. 1517 F. W. Wehrli, T. Nishida, The Use of Carbon-13 Nuclear Magnetic Resonance Spectroscopy in Natural Product Chemistry, in Zechmeister, L. et al. Progress in the Chemistry of Organic Natural Products. Wi Springer-Verlag, New York, 1979. p.93Radics, L., Kajtarperedy, M.C., Corsano, S., Standoli, L., (1975) Tetrahedron. Lett, 48, p. 4287 Gedam, P.H., Sampathkumaran, P.S., Sivasamban, M.A., (1972) Indian J. Chem, 10, p. 388 Pretsch, E., Clerc, T., Seibl, J., Simon, W., (1989) Tables of spectral data for structure determination of organic compounds, , 2nd ed, Springer-Verlag, New York Carballeira, N.M., Shalabi, F., Cruz, C., (1994) Tetrahedron Lett, 35, p. 5575 Christie, W.W., (1997) Lipid Technol, 9, p. 17 Tyman, J.H.P., Jacobs, N., (1971) J. Chromatogr, 54, p. 83 Christov, R., Trusheva, B., Papova, M., Bankova, V., Bertrand, M., (2005) Nat. Prod. Res, 19, p. 673 Kubo, I., Komatsu, S., Ochi, M.J., (1986) Agric. Food Chem, 34, p. 970 Itokawa, H., Totsuka, N., Nakahara, K., Takeya, K., Lepoittevin, J.P., Asakawa, Y., (1987) Chem. Pharm. Bull, 35, p. 3016 Itokawa, H., Totsuka, N., Nakahara, K., Maezuru, M., Takeya, K., Kondo, M., Inamatsu, M., Morita, H., (1989) Chem. Pharm. Bull, 37, p. 1619 Himejima, M., Kubo, I., (1991) J. Agric. Food Chem, 39, p. 418 Kubo, I., Muroi, H., Himejima, M., Yamagiwa, Y., Mera, H., Tokushima, K., Ohta, S., Kamikawa, T., (1993) J. Agric. Food Chem, 41, p. 1016 Kubo, I., Ochi, M., Vieira, P.C., Komatsu, S., (1993) J. Agric. Food Chem, 41, p. 1012 Muroi, H., Kubo, I., (1993) J. Agric. Food Chem, 41, p. 1780 Amorati, R., Pe dulli, G.F., Valgimgli, L., Attanasi, O.A., Filippone, P., Fiorucci, C., Saladino, R., (2001) J. Chem. Soc., Perkin Trans., 2, p. 2142 Masuoka, N., Kubo, I., (2004) Biochimi. Biophysi. Acta, 1688, p. 245 Siegers, C.P., (1999) Phytomedicine, 6, p. 281 Westendorf, J., Regan, J., (2000) Pharmazie, 55, p. 864 Hecker, H., Johannisson, R., Koch, E., Siegers, C.P., (2002) Toxicology, 177, p. 167 Trevisan, M.T.S., Pfundstein, B., Haubner, R., Wurtele, G., Spiegelhalder, B., Bartsch, H., Owen, R.W., (2006) Food Chem. Toxicol, 44, p. 188