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PubMed1995

Prodigiosin 25-C perturbs permeation of acetate in a cultured cell line.

Prodigiosin 25-C had little effect on DNA, RNA, and protein synthesis, and cellular ATP content, but the drug markedly inhibited the incorporation of acetate into lipid fractions. Under the same conditions, the incorporation of other lipid precursors including glycerol, mevalonate, palmitate, and oleate was not affected. A decrease in the incorporation of acetate was not due to the inhibition of fatty acid biosynthesis, because prodigiosin 25-C did not affect the activity of acetyl-CoA synthetase, acetyl-CoA carboxylase or fatty acid synthase in cell-free assay systems prepared from rat liver cytosol. In contrast, prodigiosin 25-C strongly inhibited the rapid uptake of acetate into acid-soluble fraction in intact cells. The results suggest that prodigiosin 25-C specifically perturbs the permeation of acetate through plasma membranes.

Acetate-CoA Ligase↗
PubMed1978

[Effect of glucose concentration on the biosynthesis of prodigiosin by serratia marcescens (author's transl)].

Serratia marcescens is an enterobacteria which produces a characteristic red pigment denominated prodigiosin. To study the effect of glucose on the kinetics of this secondary metabolite, cultures of Serratia marcescens S10 were incubated at 30 degrees C in the mineral medium GL, with glucose (2 g/l) as the carbon source. Prodigiosin production in relation to glucose consumption is studied, and parallel-wise, the effect of various concentrations of glucose on prodigiosin production. The kinetics data show the close correlation between glucose consumption and the synthesis of prodigiosin. This substrate inhibits the synthesis of pigment in cultures grown on solid medium GL with concentrations of glucose up to 15 g/l.

Animals↗
PubMed2003

Chemistry and biology of roseophilin and the prodigiosin alkaloids: a survey of the last 2500 years.

The pyrrole alkaloids of the prodigiosin family make up an unusual chapter in the chemistry of natural products. Owing to the characteristic red color of these secondary metabolites, colonies of the Gram-negative-producing bacteria may strikingly resemble droplets of blood. This phenomenon caused considerable confusion in the past and was likely responsible for many seemingly miraculous (prodigious) events. After the eventual transition from superstition to science, the prodigiosins started to attract considerable attention because of their promising physiological properties. Most interesting are the immunosuppressive activities at doses that are not cytotoxic, in particular since in vivo studies suggest that the prodigiosins act synergistically with cyclosporine A or FK 506, which are presently the dominant drugs in clinical immunosuppressive regimens. Furthermore, the chemistry of the closely related and structurally rather unique alkaloid roseophilin is summarized, a cytotoxic agent that recently became the focal point of many innovative total syntheses.

Alkaloids↗
PubMed1995

Prodigiosin 25-C uncouples vacuolar type H(+)-ATPase, inhibits vacuolar acidification and affects glycoprotein processing.

Prodigiosin 25-C inhibited the accumulation of 3-(2,4-dinitroanilino)-3'-amino-N-methyldipropylamine and acridine orange in the acidic compartments of baby hamster kidney cells with little perturbation of cellular ATP levels. In rat liver lysosomes, prodigiosin 25-C inhibited the proton pump activity with an IC50 of approximately 30 nM, but did not affect ATPase activity up to 1 microM. It also delayed the transport of vesicular stomatitis virus G protein and induced a drastic swelling of Golgi apparatus and mitochondria. These results indicate that prodigiosin 25-C raises the pH of acidic compartments through inhibition of the proton pump activity of vacuolar type H(+)-ATPase, thereby causing the functional and morphological changes to the Golgi apparatus.

Adenosine Triphosphate↗
PubMed2000

Synthesis and immunosuppressive activity of novel prodigiosin derivatives.

Prodigiosins (Ps) represent a family of naturally occurring red pigments characterized by a common pyrrolylpyrromethene skeleton. Some members of this family have been shown to possess interesting immunosuppressive properties exerted with a novel mechanism of action, different from that of currently used drugs. In fact, Ps inhibit phosphorylation and activation of JAK-3, a cytoplasmic tyrosine kinase associated with a cell surface receptor component called common gamma-chain, which is exclusive of all IL-2 cytokine family receptors. Blocking common gamma-chain transduction activity results in a potent and specific immunosuppressive activity. With respect to the interesting and unexploited immunomodulating properties of this family of compounds we initiated a medicinal chemistry program aimed at finding novel prodigiosin derivatives with improved immunosuppressive activity and lower toxicity. Utilizing an unprecedented and flexible way of assembling the prodigiosin frame, a number of new derivatives have been prepared and tested leading to the choice of 4-benzyloxy-5-[(5-undecyl-2H-pyrrol-2-ylidene)methyl]-2, 2'-bi-1H-pyrrole (PNU-156804, 16) as a lead immunosuppressant.

Animals↗
PubMed1985

Decrease in respiration activity related to prodigiosin synthesis in Serratia marcescens.

Variation in the cell respiration rate of pigmented and nonpigmented strains of Serratia marcescens was exhibited. The respiration rate of a pigmented strain decreased earlier than that of nonpigmented strains in the late exponential or early stationary phase. However when prodigiosin synthesis was not induced by exchange of carbon sources in the medium, the decrease in the respiration rate of the pigmented strain was the same as that of nonpigmented strains. Measurement of the oxygen consumption rate in the sonicated cell membrane by adding NADH solution showed that the rate in the pigmented strain was lower than that in nonpigmented strains. Furthermore, the cell membrane of prodigiosin-induced organisms was more sensitive to respiration inhibitors than that of pigment-noninduced organisms of the pigmented strain. These results showed that the respiration activity was decreased by prodigiosin synthesis in S. marcescens.

Cell Fractionation↗
PubMed2004

Identification and characterization of the pswP gene required for the parallel production of prodigiosin and serrawettin W1 in Serratia marcescens.

Serratia marcescens mutants defective in production of the red pigment prodigiosin and the biosurfactant serrawettin W1 in parallel were isolated by transposon mutagenesis of strain 274. Cloning of the DNA fragment required for production of these secondary metabolites with different chemical structures pointed out a novel open reading frame (ORF) named pswP. The putative product PswP (230 aa) has the distinct signature sequence consensus among members of phosphopantetheinyl transferase (PPTase) which phosphopantetheinylates peptidyl carrier protein (PCP) mostly integrated in the nonribosomal peptide synthetases (NRPSs) system. Since serrawettin W1 belongs to the cyclodepsipeptides, which are biosynthesized through the NRPSs system, and one pyrrole ring in prodigiosin has been reported as a derivative of L -proline tethered to phosphopantetheinylated PCP, the mutation in the single gene pswP seems responsible for parallel failure in production of prodigiosin and serrawettin W1.

Bacterial Proteins↗
PubMed2006

Transcriptional downregulator hexS controlling prodigiosin and serrawettin W1 biosynthesis in Serratia marcescens.

Serratia marcescens has been known as a temperature-dependent producer of two chemically different exolipids (red pigment prodigiosin and biosurfactant serrawettin W1) in parallel. During genetic investigation of such control mechanisms, mini-Tn 5 insertional mutant Tan1 overproducing these exolipids was isolated. The gene concerning such disregulation was identified as hexS by DNA cloning followed by sequencing and homology analysis of the presumed product with 314 amino-acids. The product HexS was the homologue of HexA of Erwinia carotovora ssp. carotovora and classified as a transcriptional regulator belonging to LysR family. By RT-PCR analysis, the hexS mutant was shown to over-transcribe the pigA gene (the first gene of the pig cluster involved in prodigiosin synthesis) and the swrW gene encoding serrawettin W1 synthetase belonging to the nonribosomal peptide synthetase family. In contrast, transcription of the pswP gene encoding phosphopantetheinyl transferase in Tan1 was in the level of parent strain 274. Purified protein encoded in his(6)-hexS demonstrated binding activity to DNA fragments of the upstream region of pigA and swrW genes and not to that of the pswP gene. S. marcescens strain 274 transformed with a low-copy plasmid carrying hexS demonstrated reduced production of prodigiosin and serrawettin W1, and reduced activity of exoenzymes (protease, chitinase, and DNase) except phospholipase C. Possible generation of virulent S. marcescens by derepression or mutation of the hexS gene in infected tissues or ex vivo environments was suggested.

Amino Acid Sequence↗
PubMed1979

New prodigiosin-like pigment from Alteromonas rubra.

The red prodigiosin-like pigment from Alteromonas rubra was shown to be a mixture of prodigiosin (pigment 1) and a new cyclic isomer (pigment 2). The new structure was elucidated by mass and nuclear magnetic resonance spectra. Careful examinations of the prodigiosins produced by Serratia marcescens, Vibrio psychoerythrus, and an unidentified red bacterium (LL-100-6) failed to disclose any of the new pigment, pigment 2.

Bacteria↗
PubMed1985

Droplet enrichment factors of pigmented and nonpigmented Serratia marcescens: possible selective function for prodigiosin.

Drops produced by bursting bubbles provide a mechanism for the water-to-air transfer and concentration of matter. Bacteria can adsorb to air bubbles rising through bacterial suspensions and enrich the drops formed by the bubbles upon breaking, creating atmospheric biosols which function in dispersal. This bacterial enrichment can be quantified as an enrichment factor (EF), calculated as the ratio of the concentration of bacteria in the drop to that of the bulk bacterial suspension. Bubbles were produced in suspensions of pigmented (prodigiosin-producing) and nonpigmented cultures of Serratia marcescens. EFs for pigmented cultures were greater than EFs for nonpigmented cells. Pigmented cells appeared hydrophobic based on their partitioning in two-phase systems of polyethylene glycol 6000 and dextran T500. The surface hydrophobicity of pigmented cells may result from the hydrophobic nature of prodigiosin and could account for the greater ability of these bacteria to adsorb to air bubbles and enrich airborne droplets. Enhancement of the aerosolization of S. marcescens may be a selective function of the bacterial secondary metabolite prodigiosin.

Aerosols↗
PubMed1969

Prodigiosin-like pigments from Actinomadura (Nocardia) pelletieri and Actinomadura madurae.

Thirteen red strains of Actinomadura (Nocardia) pelletieri and three of A. madurae were shown to produce prodigiosin-like pigments. Both of the two major pigments which were observed on thin-layer chromatograms had R(F) values significantly greater than prodigiosin. The main pigment from A. madurae 953 was shown by mass and nuclear magnetic resonance spectroscopies to be nonylprodigiosin. The major pigment from A. pellitieri had a C(11)H(22) side chain in a ring form, but it was distinctly different from metacycloprodigiosin. "Prodiginine" was proposed as a name for the invariant aromatic portion of the prodigiosin structure.

Anti-Bacterial Agents↗
PubMed1973

Defects in prodigiosin formation by L-forms of Serratia marcescens.

An L-form of Serratia marcescens has previously been shown incapable of producing the red pigment, prodigiosin, characteristic of the parent bacteria. Mutants of S. marcesens, unable to form one or the other of the two prodigiosin precursors, 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde or 2-methyl-3-n-amylpyrrole, were used to test the nature of the L-form defect. The L-forms failed to form sufficient amounts of either precursor to be detected by the appropriate mutant, and, when furnished the precursors, failed to couple them to form prodigiosin.

Cell Count↗
PubMed1974

Isolation and purification of prodigiosin from Vibrio psychroerythrus.

The red pigment of Vibrio psychroerythrus (formerly marine psychrophile NRC 1004) was identified as prodigiosin by comparison of its mass spectrum, absorption spectrum in the visible range, and chromatographic behavior with prodigiosin isolated from Serratia marcescens. The properties of the V. psychroerythrus pigment were clearly distinguishable from five other prodigiosin-like compounds isolated from three different microorganisms.

Chemical Phenomena↗
PubMed1977

Biosynthesis of prodigiosin by non-proliferating wild-type Serratia marcescens and mutants deficient in catabolism of alanine, histidine, and proline.

Mutants of Serratia marcescens Nima, designated as Aut, Hut, or Put, did not utilize L-alanine, L-histidine, or L-proline, respectively, as a sole carbon source but did utilize other amino acids or glycerol as carbon sources. The bacteria were permeable to alanine, histidine, and proline but lacked the enzymes responsible for degradation of these amino acids. The Aut mutant contained no L-alanine dehydrogenase activity, whereas the Hut and Put mutants contained only 7 and 4% of the histidase and proline oxidase activities, respectively, found in the wild-type strain. Rates of oxygen uptake and protein synthesis were significantly lower when the mutants were incubated in the presence of amino acids they could not degrade. Studies of L-[14C]alanine, L-[14C]histidine, and L-[14C]proline incorporation into prodigiosin synthesized by these mutants and the wild-type strain revealed that proline was incorporated intact, whereas all of alanine except the carboxyl group was incorporated into the pigment molecule. Histidine did not enter prodigiosin directly. These data suggested that the presence of unique biosynthetic pathways, independent of primary metabolism, leads to formation of prodigiosin from specific amino acids.

Alanine↗
PubMed1984

Cloning and expression in Escherichia coli of Serratia marcescens genes encoding prodigiosin biosynthesis.

Prodigiosin, the bright red pigment produced by many strains of Serratia marcescens, is synthesized by a bifurcated pathway that terminates in the enzymatic condensation of the two final products, a monopyrrole and a bipyrrole . Sau3A fragments of S. marcescens ( Nima ) DNA were introduced into a strain of Escherichia coli K-12 by use of the cosmid vector pHC79 , and transformed clones were selected based on resistance to ampicillin. Among 879 transformants screened, 2 could be induced to synthesize prodigiosin when supplied with either one or both terminal products of the bifurcated pathway. Data are presented to support the idea that production of prodigiosin is not usually mediated by a plasmid.

Bacteriophage lambda↗
PubMed1966

Prodigiosin synthesis in mutants of Serratia marcesens.

Morrison, D. A. (Harvard College, Cambridge, Mass.). Prodigiosin synthesis in mutants of Serratia marcescens. J. Bacteriol. 91:1509-1604. 1966.-Exchange of biosynthetic intermediates through the culture medium was used to characterize several hundred new color mutants of Serratia marcescens. The general scheme of prodigiosin synthesis as a bifurcated pathway, in which monopyrrole and bipyrrole precursors are synthesized separately and then coupled to form pigment, was confirmed and extended. Mutants of one new class excreted a product likely to be a new intermediate in monopyrrole synthesis, those of a second excreted a new product in the bipyrrole pathway, and those of a third were blocked at early steps in both pathways. Two novel classes of mutants were isolated, in each of which a lack of some product present in Serratia and Escherichia cultures resulted in loss of all steps in prodigiosin biosynthesis.

In Vitro Techniques↗
PubMed2006

Cytotoxic proteins combined with prodigiosin obtained from Serratia marcescens have both broad and selective cytotoxic activity on tumor cells.

Cytotoxic proteins and prodigiosin obtained from Serratia marcescens strains are known to induce tumor cell death, nevertheless its combination has not been studied. In this paper we evaluate the combined effects of these molecules in a panel of tumor cell lines. The results showed a marked inhibitory effect on the growth of tumor cell lines derived from tumors (i.e., melanoma) which are highly resistant to conventional anticancer drugs, while normal cells were less sensitive than tumor cells. TUNEL (TdT-mediated dUTP nick end labeling) and electrophoresis of HEp-2 cell DNA treated with MG2327 preparation [containing the P50 protein belonging to the serralysins and prodigiosin, from S. marcescens CMIB4202] showed a pattern of DNA fragments typically associated with apoptosis. Interestingly, prodigiosin enhanced by 1.6-fold the cytotoxic effect of P50 when acting in combination on HEp-2 cells. The broad cytotoxic activity of the combination on tumor cells as well as its selectivity open new frontiers in cancer therapy.

Anti-Bacterial Agents↗
PubMed2006

Purification and characterization of prodigiosin produced by integrated bioreactor from Serratia sp. KH-95.

To date, prodigiosin and its analogues which have been shown to have anticancer, cytotoxic and immunosuppressive activities have been isolated from Serratia, Pseudomonas and Streptomyces species, and chemically synthesized. In a previous study, the red pigment content in Serratia sp. KH-95 was enhanced using a casein-enriched medium. Recently, an integrated bioreactor with an internal adsorbent has been developed to increase the production yield and allow easy recovery of the pigment. Thus, this study focused on both purifying and identifying a single red pigment from several pigments attached to the adsorbent in an integrated bioreactor. The red pigment was extracted directly from the internal adsorbent using acidified methanol and phase separation. Subsequently, it was purified by silica gel chromatography and high performance liquid chromatograph (HPLC). As a result, pure prodigiosin was identified by structural studies as a pigment. Also, this downstream procedure that uses the integrated bioreactor can be applied to the direct production and purification of other prodigiosin analogues and hydrophobic alkaloid compounds from several microorganisms.

Bioreactors↗