Keywords
antibacterial activity
triterpenoids
Brazilian propolis
alkylthiolation
How to Cite
Abstract
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.
References
E. L. Ghisalbert, Bee World. 60 (1979) 59.
C. Garcia-Viguera, W. Greenaway, F. R. Watley, Z.
Naturforsch., Tubigen. 47c (1992) 634.
T. Usia, A. H. Banskota, Y. Tezuka, K. Midorikawa, K.
Matsushige, S. Kadota, J. Nat. Prod. 65 (2002) 673.
M. C. Marcucci, Apidologie. 26 (1995) 83.
G. A. Burdock, Food Chem. Toxicol. 36 (1998) 347.
A. H. Banskota, T. Nagaoka, L. Y. Sumioka, Y. Tezuka, S.
Awale, K. Midorikawa, K. Matsushige, S. J. Kadota, Ethnopharmacology. 80 (2002) 67.
V. S. Bankova, A Diulgerov., S. S. S. Popov, , L. Evstatieva, L. Kuleva, O. Pureb, Z Zamjasan, Apidologie, 23 (1992) 79.
V. Bankova, S. L. Castro, M. C. Marcucci, Apidologie, 31
(2000) 3.
A. S. Pereira, E. A. Nascimento, F. R. Aquino Neto, Z.
Naturforsch., 57c (2002) 721.
M. S. S. Silva, A. M. G. L. Citó, M. H. Chaves, J. A. D.
Lopes, Quím. Nova, 28 (2005) 801.
S. G. De Lima “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, 2005, 350p.
C. Wang. The role of lipids in disease resistance and fruit
ripening tomato. Ph.D. Thesis. Rutgers University, New
Brunswick, N.J., 1998.
G. W. FRANCIS, K. VELAND, J. Chromatogr., 219 (1981) 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, 104p.
P. R. Murray, W. L. Drew, G. S. Kobayasai, J. R. Thompson, “Microbiologia Médica,”. Guanabara Koogan,
Rio de Janeiro, 1990.
N. F. Roque, R. S. G. Olea, Quim. Nova, 13 (1990) 278.
S. B. Mahato, A. P. Kundu, Phytochemistry, 37(1994)
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.93.
L. Radics, M. C. Kajtarperedy, S. Corsano, L. Standoli,
Tetrahedron. Lett., 48 (1975) 4287.
P. H. Gedam, P. S. Sampathkumaran, M. A. Sivasamban,
Indian J. Chem., 10 (1972) 388.
E. Pretsch, T. Clerc, J. Seibl, W. Simon, “Tables of spectral data for structure determination of organic compounds,” 2nd ed, Springer-Verlag, New York, 1989.
N. M. Carballeira, F. Shalabi, C. Cruz, Tetrahedron Lett.
, 35, 5575.
W. W. Christie, Lipid Technol., 9, (1997) 17.
J. H. P. Tyman, N. Jacobs, J. Chromatogr., 54 (1971) 83.
R. Christov, B. Trusheva, M. Papova, V. Bankova, M.
Bertrand, Nat. Prod. Res., 19 (2005) 673.
I. Kubo, S. Komatsu, M. J. Ochi, Agric. Food Chem., 34
(1986) 970.
H. Itokawa, N. Totsuka, K. Nakahara, K. Takeya, J. P.
Lepoittevin, Y. Asakawa, Chem. Pharm. Bull., 35 (1987) 3016.
H. Itokawa, N. Totsuka, K. Nakahara, M. Maezuru, K.
Takeya, M. Kondo, M. Inamatsu, H. Morita, Chem. Pharm.
Bull., 37 (1989) 1619.
M. Himejima, I. Kubo, J. Agric. Food Chem., 39 (1991) 418.
I. Kubo, H. Muroi, M. Himejima, Y. Yamagiwa, H. Mera,
K. Tokushima, S. Ohta, T. Kamikawa, J. Agric. Food Chem.,
(1993) 1016.
I. Kubo, M. Ochi, P. C. Vieira, S. Komatsu, J. Agric. Food Chem., 41 (1993) 1012.
H. Muroi, I. Kubo, J. Agric. Food Chem., 41 (1993) 1780.
R. Amorati, G. F. Pe dulli, L. Valgimgli, , O. A. Attanasi,
P. Filippone, C. Fiorucci, R. Saladino, J. Chem. Soc., Perkin
Trans., 2 (2001)2142.
N. Masuoka, I. Kubo, Biochimi. Biophysi. Acta, 1688
(2004) 245.
C. P. Siegers, Phytomedicine, 6 (1999) 281.
J. Westendorf, J. Regan, Pharmazie, 55 (2000) 864.
H. Hecker, R. Johannisson, E. Koch, C. P. Siegers,
Toxicology, 177 (2002) 167.
M. T. S. Trevisan, B. Pfundstein, R. Haubner, G. Wurtele,
B. Spiegelhalder, H. Bartsch, R.W. Owen, Food Chem. Toxicol., 44 (2006) 188.
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