Influence on dithiolopyrrolone antibiotic production by organic acids in Saccharothrix algeriensis NRRL B-24137

Bouras, Noureddine; Mathieu, Florence; Sabaou, Nasserdine; Lebrihi, Ahmed

doi:10.1016/j.procbio.2007.02.007

Cited by 19 publications

(19 citation statements)

References 33 publications

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“…The actinomycete S. algeriensis produces five dithiolopyrrolones in the basic medium (without precursors): thiolutin, iso‐butyryl‐pyrrothine, butanoyl‐pyrrothine, senecioyl‐pyrrothine and tigloyl‐pyrrothine (Lamari et al , 2002b). This actinomycete has a great ability to produce a wide range of dithiolopyrrolone derivatives that, depending on the composition of the culture medium, nature and concentration of precursors added and an enzymatic system, are involved in attaching a variety of radicals (R) into pyrrothine ring (Bouras et al , 2006a, b, 2007, 2008; Chorin et al , 2009). The data presented above show that the addition of sorbic acid at a concentration of 5 mM to the SSM as a precursor has induced the production of four new peaks, as revealed by HPLC analysis.…”

Section: Discussionmentioning

confidence: 99%

“…Furthermore, the addition of precursors to the culture medium led to the modification in production levels of known dithiolopyrrolones (Bouras et al , 2006a, b) and also to precursor‐directed biosynthesis of new dithiolopyrrolone analogues (Bouras et al , 2007, 2008). Consequently, S. algeriensis has the ability to produce a wide range of dithiolopyrrolones based on different acyl‐CoA depending on the precursors added (Bouras et al , 2007, 2008). Recently, Merrouche et al (2010) showed that the addition of valeric acid at a concentration of 5 mM induced the production of three new dithiolopyrrolone derivatives: formyl‐pyrrothine, valeryl‐pyrrothine and iso‐valeryl‐pyrrothine (Fig.…”

Section: Introductionmentioning

confidence: 99%

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New dithiolopyrrolone antibiotics induced by adding sorbic acid to the culture medium of Saccharothrix algeriensis NRRL B-24137

Merrouche

Bouras

Coppel

et al. 2011

FEMS Microbiology Letters

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Dithiolopyrrolone antibiotics, produced by several microorganisms, are known for their strong antimicrobial activities. This class of antibiotics generated new interest after the discovery of their anticancer and antitumor properties. In this study, four new antibiotics were purified from the fermentation broth of Saccharothrix algeriensis NRRL B-24137 and characterized as dithiolopyrrolone derivatives. These new dithiolopyrrolone antibiotics were induced by adding sorbic acid, as precursor, at a concentration of 5 mM to the semi-synthetic medium. The analysis of the induced antibiotics was carried out by HPLC. The maximal production of the antibiotics PR2, PR8, PR9 and PR10 was 0.08±0.04, 0.21±0.04, 0.13±0.03 and 0.09±0.00 mg L(-1) , respectively, obtained after 8 days of fermentation. The chemical structures of these antibiotics were determined by (1) H- and (13) C-nuclear magnetic resonance, mass and UV-visible data. The four new dithiolopyrrolone antibiotics - PR2, PR8, PR9 and PR10 - were characterized, respectively, as crotonyl-pyrrothine, sorbyl-pyrrothine, 2-hexonyl-pyrrothine and 2-methyl-3-pentenyl-pyrrothine. The minimum inhibitory concentrations of the new induced antibiotics were determined.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New dithiolopyrrolone antibiotics induced by adding sorbic acid to the culture medium of Saccharothrix algeriensis NRRL B-24137

Merrouche

Bouras

Coppel

et al. 2011

FEMS Microbiology Letters

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“…Furthermore, the addition of amino acids and organic acids as precursors to the basal semi‐synthetic (SS) medium containing glucose, yeast extract and several mineral sources permitted to modify the production levels of this known dithiolopyrrolones (Bouras et al . ,b, ). The so called precursor directed biosynthesis (PDB) method also permitted the production of several uncommon new analogues, among which seven of them were fully characterized by mass and RMN (Fig.…”

Section: Introductionmentioning

confidence: 99%

Effective biosynthesis of benzoyl-pyrrothine dithiolopyrrolone antibiotic by cinnamic acid-precursor addition in culture of Saccharothrix algeriensis NRRL B-24137

Merrouche

Yekkour

Coppel

et al. 2019

Lett Appl Microbiol

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Dithiolopyrrolone antibiotics, produced by several micro‐organisms, are known for their strong antimicrobial and antitumor activities. Among of this micro‐organisms, Saccharothrix algeriensis NRRL B‐24137, a rare actinobacterium, has the ability to produce several dithiolopyrrolones derivatives depending on precursors added in the culture medium. After 10 days of strain fermentation on semi‐synthetic medium supplemented with cinnamic acid and HPLC purification, biosynthesis of benzoyl‐pyrrothine dithiolopyrrolone was evidenced through complete spectroscopic (UV–visible and 1H and 13C NMR) and spectrometric (electron impact mass spectrum) analyses. The pure molecule showed appreciable minimum inhibitory concentration values against several Gram‐positive bacteria and filamentous fungi. Significance and Impact of the Study Dithiolopyrrolone antibiotics, known for their strong antimicrobial activities, gained greater interest after the discovery of their antitumor properties. Depending on precursors added, Saccharothrix algeriensis NRRL B‐24137 has the ability to produce several dithiolopyrrolones derivatives. Since biological activities of dithiolopyrrolones are related to their variable structure, discover of new natural analogues to be therapeutically explored remains a significant framework of research. In this study, a new dithiolopyrrolone derivative was purified from the fermentation broth of S. algeriensis NRRL B‐24137. This new antibiotic, characterized as benzoyl‐pyrrothine dithiolopyrrolone, was induced by adding cinnamic acid, as precursor, to a semi‐synthetic medium.

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“…[8][9][10][11][12][13][14] Dithiolopyrrolones have also been reported to have anticancer activity, [15][16][17] and shown potent membrane stabilization and platelet anti-aggregate activities. 18 We first reported that ZL-004 ( Figure 1) exhibited antileukopenia activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Dithiolopyrrolone Derivatives and Their Leukocyte-Increasing Activities

Li¹,

Sun²,

Wang³

et al. 2014

Bulletin of the Korean Chemical Society

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In search of new antileukopenia agents, twenty dithiolopyrrolone derivatives were synthesized and evaluated for their leukocyte-increasing activities in normal mice. Among the synthesized compounds 4-23, compounds 5 and 6 showed significant leukocyte-increasing activity ( p < 0.01), and compounds 4, 9 and 16 had a moderate effect ( p < 0.05). Compound 5 also displayed stronger leukocyte-increasing activity than that of the positive recombinant human granulocyte colony stimulating factor (rhG-CSF). Above all, compound 5 would be a potential antileukopenia agent which deserved further research.

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Influence on dithiolopyrrolone antibiotic production by organic acids in Saccharothrix algeriensis NRRL B-24137

Cited by 19 publications

References 33 publications

New dithiolopyrrolone antibiotics induced by adding sorbic acid to the culture medium of Saccharothrix algeriensis NRRL B-24137

New dithiolopyrrolone antibiotics induced by adding sorbic acid to the culture medium of Saccharothrix algeriensis NRRL B-24137

Effective biosynthesis of benzoyl-pyrrothine dithiolopyrrolone antibiotic by cinnamic acid-precursor addition in culture of Saccharothrix algeriensis NRRL B-24137

Synthesis of Dithiolopyrrolone Derivatives and Their Leukocyte-Increasing Activities

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