Pumilacidins A-E from Sediment-Derived Bacterium Bacillus sp. 4040 an Their Antimicrobial Activity Evaluation

Oliveira, Josiane A. M. de; Williams, David E.; Andersen, Raymond J.; Sarragiotto, Maria H.; Baldoqui, Debora C.

doi:10.21577/0103-5053.20190188

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Journal of the Brazilian Chemical Society

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Articles • J. Braz. Chem. Soc. 31 (2) • Feb 2020 • https://doi.org/10.21577/0103-5053.20190188 copy

Pumilacidins A-E from Sediment-Derived Bacterium Bacillus sp. 4040 an Their Antimicrobial Activity Evaluation

Authorship SCIMAGO INSTITUTIONS RANKINGS

Marine strains of Bacillus are known to produce secondary metabolites different from that accumulated by their terrestrial counterparts, for example, lipopeptides such as surfactins, iturins and fengycins, which exhibit a variety of biological activities. Another important class of lipopeptides are pumilacidins, identified specially from Bacillus pumilus strains, usually by using liquid chromatography-mass spectrometry (LC-MS) techniques. In this work, five knowns pumilacidins were isolated from the solid culture of the marine-derived bacterium Bacillus sp. 4040. The structures of compounds, pumilacidins A-E, were determined using a combination of mass spectrometry, nuclear magnetic resonance (NMR) spectroscopy and comparison with reported data. The ¹H and ¹³C NMR data of pumilacidin B is being described here for the first time. All compounds were evaluated against five microorganisms, but no antimicrobial activity was detected.

Keywords:
Bacillus sp.; cyclic lipopeptides; pumilacidins; antimicrobial activity

Position	No.	δ_C / ppm	δ_H / ppm (mult., J / Hz)
Glu	1	171.1	-
	2	52.1	4.15 (m)
	3	27.4	1.70/1.87 (m)
	4	30.0	2.18 (t, 7.8)
	5	174.0	-
	NH		7.84 (d, 6.6)
	-OH
Leu-1	1	172.2	-
	2	51.9	4.14 (m)
	3	39.7	1.46 (m)
	4	24.4	1.46 (m)
	5	23.0	0.79 (m)
	6	22.5	0.79 (m)
	NH		7.97 (bs)
Leu-2	1	172.1	-
	2	51.8	4.09 (m)
	3	39.7	1.49 (m)
	4	24.2	1.49 (m)
	5	23.0	0.79 (m)
	6	22.6	0.79 (m)
	NH		8.16 (m)
Leu-3	1	171.8	-
	2	51.3	4.20 (m)
	3	40.8	1.38 (m)
	4	23.9	1.53 (m)
	5	21.7	0.77 (m)
	6	23.2	0.82 (m)
	NH		8.01 (d, 6.6)
Asp	1	170.0	-
	2	49.7	4.45 (m)
	3	36.0	2.64 (dd, 4.8. 17.4)/ 2.56 (dd, 9.0. 16.2)
	4	171.7	-
	NH		8.10 (d, 7.2)
Leu-4	1	171.7	-
	2	50.6	4.44 (m)
	3	41.3	1.38
	4	24.2	1.48
	5	23.0	0.77
	6	21.6	0.82
	NH		7.66 (d, 8.4)
Val	1	170.7	-
	2	57.4	4.05 (m)
	3	29.4	2.03 (m)
	4	18.1	0.80 (m)
	5	19.2	0.81 (m)
	NH		8.14 (m)
Fatty acid (anteiso-)	1'	169.6	-
	2'	40.6	2.38 (m)
	3'	71.6	4.97 (m)
	4'	33.3	1.50 (m)
	5'	24.1	1.17 (m)
	6'-10'	28.6-29.3	1.18 (m)
	11'	36.0	1.02/1.20 (m)
	12'	33.7	1.23 (m)
	13'	26.5	1.18 (m)
	14'	11.2	0.79 (m)
	15'	19.2	0.83 (m)

Position	No.	δ_C / ppm	δ_H / ppm (mult., J / Hz)
Glu	1	171.1	-
	2	52.0	4.14 (m)
	3	27.4	1.71/1.87 (m)
	4	29.9	2.17 (t, 7.8)
	5	174.0	-
	NH		7.86 (d, 6.6)
	-OH
Leu-1	1	172.1	-
	2	52.1	4.12 (m)
	3	38.5	1.42 (m)
	4	23.9	1.46 (m)
	5	23.0	0.78 (m)
	6	22.5	0.78 (m)
	NH		7.97 (bs)
Leu-2	1	172.1	-
	2	51.7	4.08 (m)
	3	39.7	1.46 (m)
	4	24.2	1.51 (m)
	5	23.0	0.82 (m)
	6	22.7	0.82 (m)
	NH		8.19 (d, 6.0)
Leu-3	1	171.6	-
	2	51.3	4.22 (m)
	3	40.8	1.39 (m)
	4	234.0	1.53 (m)
	5	21.8	0.75 (m)
	6	23.0	0.83 (m)
	NH		7.98 (bs)
Asp	1	170.0	-
	2	49.7	4.45 (m)
	3	36.1	2.64 (dd, 4.8. 17.4)/ 2.56 (dd, 9.0. 16.2)
	4	171.7	-
	NH		8.10 (d, 7.2)
Leu-4	1	171.8	-
	2	50.5	4.44 (m)
	3	41.3	1.39
	4	24.4	1.47
	5	23.0	0.82
	6	22.5	0.82
	NH		7.66 (d, 8.4)
Ile	1	170.7	-
	2	56.5	4.10 (m)
	3	35.8	1.79 (m)
	4	24.6	1.25 (m)
	5	11.2	0.76 (m)
	6	15.5	0.79 (m)
	NH		8.14 (d, 7.8)
Fatty acid (anteiso-)	1'	169.5	-
	2'	40.8	2.38 (m)
	3'	71.7	4.95 (m)
	4'	33.3	1.52 (m)
	5'	24.2	1.17 (m)
	6'-10'	28.9-29.4	1.16 (m)
	11'	36.0	1.00/1.21 (m)
	12'	33.8	1.21 (m)
	13'	26.5	1.18 (m)
	14'	11.2	0.77 (m)
	15'	19.1	0.76 (m)

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[1] *e-mail: mhsarragiotto@uem.br dcbaldoqui@uem.br