Antimicrobial activity of the myrsinoic acid A from <i>Myrsine coriacea</i> and the semi-synthetic derivatives

Burger, Marcela Carmen de Melo; Terezan, Ana Paula; Cunha, Gracielle Silva de Oliveira; Fernandes, Joao Batista; Silva, Maria Fatima das Graças Fernandes da; Vieira, Paulo Cezar; Menezes, Antonio Carlos Severo

doi:10.1016/j.bjp.2015.07.023

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Original Articles • Rev. bras. farmacogn. 25 (5) • Oct 2015 • https://doi.org/10.1016/j.bjp.2015.07.023 copy

Antimicrobial activity of the myrsinoic acid A from Myrsine coriacea and the semi-synthetic derivatives

Authorship SCIMAGO INSTITUTIONS RANKINGS

ABSTRACT

The antimicrobial activity of the myrsinoic acid A isolated from Myrsine coriacea (Sw.) R.Br. ex Roem. & Schult., Primulaceae, and a two semi-synthetics derivatives was tested against Bacillus subtilis, Escherichia coli, Salmonella enterica subsp. enterica serovar typhi, Staphylococcus aureus, Streptococcus pyogenes, Pseudomonas aeruginosa, Micrococcus luteus, Candida albicans, Candida krusei and Candida tropicalis. The microdilution method was used for the determination of the minimum inhibitory concentration during evaluation of the antimicrobial activity. The myrsinoic acid A showed no activity against the selected microorganisms but the hydrogenated and acetylated derivatives were active against B. subtilis, E. coli, S. aureus and P. aeruginosa.

Keywords:
Myrsine coriace ; Antimicrobial activity; Primulaceae; Myrsinoic acid A

¹H NMR	1	1^a a Cruz et al. (2013).	1^b b Dong et al. (1999).	2	3	3^b b Dong et al. (1999).	¹³CNMR	1	1^a a Cruz et al. (2013).	1^b b Dong et al. (1999).	3^b b Dong et al. (1999).
1							1	120.9	121.0	123.8	125.9
2	7.68, s	7.77, s	7.77, s	7.76, s	7.83, s	7.84, s	2	130.0	130.5	130.5	134.5
3							3	127.0*	127.0	127.4*	127.0*
4							4	157.4	158.0	158.0	151.9
5							5	126.6*	127.0	127.0*	129.8*
6	7.68, s	7.77, s	7.77, s	7.76, s	7.83, s	7.83, s	6	130.0	130.5	130.5	134.5
1'	3.33, d, J = 7.2	3.38, t = 7.0	3.38, t = 7.0	2.62, m	3.23, d, J = 7.2*	3.24, d, J = 6.3	1'	29.0*	29.7	29.7*	28.9*
2'	5.25, brt, J = 7.2	5.32, t = 7.0	5.32, t = 6.8	1.10-1.68, m	5.25, brt, J = 7.2	5.25, brt, J = 7.1*	2'	120.8*	121.2	121.4*	120.9*
3'				1.10-1.68, m			3'	138.6	139.1	139.1	137.6
4'	2.04, m	2.11, m	2.09, m	1.10-1.68, m	2.08, m	2.10, m	4'	39.4	39.7	39.7	39.7
5'	2.04, m	2.11, m	2.14, m	1.10-1.68, m	2.08, m	2.10, m	5'	26.0	26.3	26.4	26.6
6'	5.01, brt, J = 7.2	5.08, m	5.08, brt, J = 6.4	1.10-1.68, m	5.11, brt, J = 7.2	5.11, brt, J = 6.7	6'	123.5	123.8	123.8	124.1
7'				1.10-1.68, m			7'	134.5	131.8	132.0	131.6
8'	1.61, s	1.69, s	1.68, s	0.87, d, J = 6.6	1.60, s	1.60, s	8'	25.3	25.7	25.7	25.7
9'	1.71, s	1.77, s	1.77, s	0.97, d, J = 6.6	1.70, s	1.69, s	9'	17.3	16.2	16.2	16.6
10'	1.53, s	1.60, s	1.60, s	0.96, d, J = 6.6	1.69, s	1.67, s	10'	15.9	17.9	17.7	17.7
1"	3.33, d, J = 7.2	3.38, t = 7.0	3.38, t = 7.0	2.62, m	3.24, d, J = 7.2*	3.24, d, J = 6.3	1"	29.3*	29.3	29.4*	28.8*
2"	5.25, brt, J = 7.2	5.32, t = 7.0	5.32, t = 6.8	1.10-1.68, m	5.25, brt, J = 7.2	5.24, brt, J = 7.2*	2"	121.0*	121.4	121.2*	120.8*
3"				1.10-1.68, m			3"	132.6	134.0	134.9	133.9
4"	1.71, s*	1.77, s	1.77, s	0.87, d, J = 6.6	1.70, s	1.70, s	4"	25.4	17.9	25.8	25.7
5"	1.70, s*	1.77, s	1.77, s	0.97, d, J = 6.6	1.76, s	1.76, s	5"	17.5	25.8	17.9	17.9
							COO	170.4	172.0	172.2	170.7
CH₃CO					2.33, s	2.33, s	CH₃CO				20.5
							CH₃CO				168.5

Compounds	Minimum inhibitory concentration (µg/ml)
	Bs	Ec	St	Sa	Sp	Pa	Ml	Ca	Ck	Ct
1	-	-	-	-	-	-	-	-		-
2	15.6	15.6	-	15.6	-	15.6	-	-	-	-
3	62.5	125	-	125	-	125	-	-	-	-
Vancomycin	0.047
Chloridrate of tetracycline		3.13	0.78	0.75	0.094	1.56	0.19
Nystatin								25.0	25.0	50.0

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[1] * Corresponding author. E-mail: djbf@ufscar.br (J.B. Fernandes).