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. 2020 Feb 26;5(9):4626-4635.
doi: 10.1021/acsomega.9b04322. eCollection 2020 Mar 10.

An Indonesian Marine Bacterium, Pseudoalteromonas rubra, Produces Antimicrobial Prodiginine Pigments

Edi Setiyono  1 , Marcelinus Alfasisurya Setya Adhiwibawa  1 , Renny Indrawati  1 , Monika Nur Utami Prihastyanti  1 , Yuzo Shioi  1 , Tatas Hardo Panintingjati Brotosudarmo  1
Affiliations

An Indonesian Marine Bacterium, Pseudoalteromonas rubra, Produces Antimicrobial Prodiginine Pigments

Edi Setiyono et al. ACS Omega. .

Abstract

Red pigmented marine bacteria, Pseudoalteromonas rubra strains PS1 and SB14, were isolated from two sampling locations in different ecosystems on Alor Island, Indonesia, and cultured in the laboratory. We analyzed the 16S rRNA gene sequences and examined the pigment composition and found that both strains produced cycloprodigiosin (3), prodigiosin (4), and 2-methyl-3-hexyl-prodiginine (5) as major compounds. In addition, we detected three minor compounds: prodigiosin derivatives 2-methyl-3-propyl prodiginine (1), 2-methyl-3-butyl prodiginine (2), and 2-methyl-3-heptyl-prodiginine (6). To our knowledge, this is the first report that P. rubra synthesizes not only prodigiosin and cycloprodigiosin but also four prodigiosin derivatives that differ in the length of the alkyl chain. The antimicrobial activity of cycloprodigiosin, prodigiosin, and 2-methyl-3-hexyl-prodiginine was examined by a disk-diffusion test against Escherichia coli, Staphylococcus aureus, Salmonella typhi, and Candida albicans. We found that, at a concentration of 20 μg/mL, cycloprodigiosin showed the greatest inhibition (25.1 ± 0.55 mm) against S. aureus.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
(A) Sampling locations on Alor Island; inset shows the Indonesian Archipelago. (B) Two isolated strains, PS1 and SB14. (C) UV–Vis absorption spectra of their crude pigment extracts in methanol. (Photos were taken by E. Setiyono.)
Figure 2
Figure 2
(A) Differences in the color of prodiginine in acidic (pH 2), neutral (pH 7), and alkaline (pH 12) conditions. (B) Associated UV–Vis absorption spectra. (Photos were taken by E. Setiyono.)
Figure 3
Figure 3
(A) 16S rRNA gene PCR amplicons on 0.8% agarose gel of P. rubra strains PS1 and SB14. (B) Phylogeny of strains PS1 and SB14, the type strains of recognized species in the genus Pseudoalteromonas, and representatives of related taxa. Corallincola platygyrae was used as an outgroup. Only bootstrap values >50% (expressed as percentages of 1000 replications) are shown at branch points. Asterisks indicate that the corresponding nodes were also recovered in the trees generated with the maximum-likelihood and maximum-parsimony algorithms. Bar, 0.01 substitutions per nucleotide position.
Figure 4
Figure 4
HPLC chromatogram of the crude pigment extract of P. rubra strain PS1 and the UV–Vis spectra of the eluent peaks.
Figure 5
Figure 5
ESI-MS/MS analysis of the purified compounds. Full Q1 scan (left) and product ion scan (right) mass spectra of (A) cycloprodigiosin, (B) prodigiosin, (C) 2-methyl-3-hexyl-prodiginine, and (D) 2-methyl-3-heptyl-prodiginine.
Figure 6
Figure 6
Molecular structure and fragmentation of identified molecules at different CEs based on optimized product ions using MRM. For the optimum CE values, see Table 1. 1, 2-methyl-3-propyl prodiginine; 2, 2-methyl-3-butyl prodiginine; 3, cycloprodigiosin; 4, prodigiosin; 5, 2-methyl-3-hexyl prodiginine; 6, 2-methyl-3-heptyl prodiginine.
Figure 7
Figure 7
Antimicrobial activity of cycloprodigiosin (2), prodigiosin (3), and 2-methyl-3-hexyl prodiginine (4) compared to the standard antibiotic amoxicillin (5), ampicillin (6), and chloramphenicol (7). DMSO as a negative control is marked with number 1. (Photos were taken by E. Setiyono.)
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