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At least 19 recordsLinked to original sources
PubMed1975

Prodigiosin-like pigments.

Prodigiosin, the bright red tripyrrole pigment from Serratia marcescens, has also been identified in Pseudomonas magnesiorubra, Vibrio psychroerythrus, and two Gram-negative rod-shaped mesophilic marine bacteria not members of the genus Serratia. Prodigiosin is sometimes bound to proteins; thus, extracts may require acid treatment before isolation of the pigment. Higher homologs of prodigiosin have been detected by mass spectroscopy. A mutant strain of S. marcescens produced nor-prodigiosin, in which the methoxy group of prodigiosin is replaced by a hydroxy group. Another mutant strain produced a blue tetrapyrrole pigment whose structure is a dimer of prodigiosin's rings A and B. Three novel biosynthetic analogs of prodigiosin have been obtained using a colorless mutant which does make rings A and B but not ring C and which can couple rings A and B with some added monopyrroles similar to ring C. The structures of three prodiginine (prodigiosin-like) pigments from streptomyces have been elucidated. All have the methoxytripyrrole aromatic nucleus of prodigiosin and all have an 11 carbon aliphatic side chain attached at carbon 2 of ring C. In two of the pigments the side chain is also linked to another carbon of ring C. The earlier literature about prodiginine pigments from actinomycetes has been interpreted and evaluated in light of the most recent findings. The structure elucidation of six prodiginine pigments from Actinomadurae (Nocardiae) has been completed. Only one, undecylprodiginine, is the same as from a streptomycete. For three of the six pigments, nine carbon side chains are observed and in four of them the side chain is attached to carbon 5 of ring A as well as carbon 2 of ring C so that a large ring is formed which includes the three pyrrole moieties. A section on identification summarized useful methods and presents information with which any known prodiginine pigment can be identified. The final step in the biosynthesis of prodigiosin was known to be the coupling of methoxybipyrrolecarboxaldehyde (rings A and B) with methylpentylpyrrole (ring C). Recent work using 13C-labeled precursors and Fourier transform 13C nuclear magnetic resonance has shown the pattern of incorporation for acetate, proline, glycine, serine alanine, and methionine into prodigiosin. Each pyrrole ring is constructed in a different way. Two of the streptomyces pigments have also been investigated; the pattern of incorporation is similar to that for prodigiosin. The biological activities of some prodiginine pigments are summarized. All show activity against several Gram-positive bacteria; some have anti-malarial activity. Prodigiosin has been tested clinically against coccidioidomycosis.

Actinomycetaceae↗
PubMed1976

Macromolecular syntheses during biosynthesis of prodigiosin by Serratia marcescens.

Amino acids that were utilized as sole sources of carbon and nitrogen for growth of Serratia marcescens Nima resulted in biosynthesis of prodigiosin in non-proliferating bacteria. Addition of alanine, proline, or histidine to non-proliferating cells incubated at 27 C increased the rate of protein synthesis and also caused biosynthesis of prodigiosin. No increase in the rate of protein synthesis was observed upon the addition of amino acids that did not stimulate prodigiosin biosynthesis. Increased rates of synthesis of ribonucleic acid (RNA) and of deoxyribonucleic acid (DNA) (a small amount) also occurred after addition of amino acids that resulted in biosynthesis of prodigiosin. After incubation of 24 h, the total amount of protein in suspensions of bacteria to which alanine or proline was added increased 67 and 98%, respectively. Total amounts of DNA and of RNA also increased before synthesis of prodigiosin. The amounts of these macromolecules did not increase after addition of amino acids that did not induce biosynthesis of progidiosin. However, macromolecular synthesis was not related only to prodigiosin biosynthesis because the rates of DNA, RNA, and protein synthesis also increased in suspensions of bacteria incubated with proline at 39 C, at which temperature no prodigiosin was synthesized. The quantities of DNA, RNA, and protein synthesized were lower in non-proliferating cells than in growing cells. The data indicated that amino acids causing biosynthesis of prodigiosin in non-proliferating cells must be metabolized and serve as sources of carbon and of nitrogen for synthesis of macromolecules and intermediates. Prodigiosin was synthesized secondarily to these primary metabolic events.

Amino Acids↗
PubMed1992

Immunomodulating properties of prodigiosin 25-C, an antibiotic which preferentially suppresses induction of cytotoxic T cells.

An antibiotic, prodigiosin 25-C, preferentially suppresses cytotoxic T lymphocytes (CTL) without affecting antibody production. Here, we investigated the effect of prodigiosin 25-C on delayed-type hypersensitivity (DTH), graft versus host reaction (GvHR) and allogeneic skin graft rejection. DTH reactions were markedly inhibited by ip treatment of the mice with prodigiosin 25-C. Cell transfer experiments indicated that prodigiosin 25-C exerted its suppressive effect on the late efferent phase rather than on the induction phase of DTH. Prodigiosin 25-C suppressed induction of anti-host CTL when GvHR was induced by iv inoculating splenocytes of parental C57BL/6 mice to adult unirradiated BDF1 mice. It had little effect on GvHR-induced splenomegaly observed 2 weeks after the inoculation, but significantly delayed the subsidence of splenomegaly as revealed 8 weeks later, suggesting that suppression of CTL converts immunosuppressive GvHR to immunostimulative one as reported by G. M. Shearer. However, reduction of interleukin-2 (IL-2) production and mitogen responses induced by GvHR were not rescued by prodigiosin 25-C treatment. Prodigiosin 25-C moderately prolonged survival of major histocompatibility (MHC)-mismatched skin grafts. Since the mode of action of prodigiosin 25-C is distinct from those of cyclosporin A and FK506, these results demonstrate potential usefulness of the antibiotic for a supplementary immunosuppressant.

Animals↗
PubMed1992

Effects of prodigiosin 25-C on cultured cell lines: its similarity to monovalent polyether ionophores and vacuolar type H(+)-ATPase inhibitors.

Prodigiosin 25-C inhibited the proliferation of various cultured cell lines more strongly when concanavalin A (Con A) was added to the cultures. The increase in sensitivity was most evident in T lymphoma YAC-1 cells. The combination of prodigiosin 25-C and Con A induced characteristic morphological changes in these cells. In the presence of Con A, monovalent polyether ionophores and vacuolar type H(+)-ATPase inhibitors induced effects similar to those of prodigiosin 25-C on YAC-1 cells. Prodigiosin 25-C had neither K+ionophore activity nor inhibitory effect on vacuolar type H(+)-ATPase. A Golgi mannosidase II inhibitor, swainsonine, inhibited the proliferation of YAC-1 cells only when Con A was added. Prodigiosin 25-C and swainsonine increased Con A binding receptors on the surface of YAC-1 cells. These results suggest that prodigiosin 25-C affects the intracellular transport and/or processing of glycoproteins.

Biological Transport↗
PubMed1976

Role of L-proline in the biosynthesis of prodigiosin.

Nonproliferating cells of Serratia marcescens, wild-type strain Nima, synthesized the pigment, prodigiosin, when saline suspensions were incubated with aeration at 27 degrees C in the presence of proline or alanine. Mutants PutS1 and PutS2 derived from strain Nima formed prodigiosin from alanine, but not from proline, unless alanine also was added. Strain Nima utilized proline as a sole source of carbon and of nitrogen for growth, whereas Put mutants did not. Investigation of enzymes degrading proline showed that the wild-type strain contained proline oxidase, which was absent in Put mutants. The wild type, as well as the mutants, utilized alanine as the sole source of carbon and nitrogen for growth. Although nonproliferating cells of Put mutants failed to synthesize prodigiosin from proline, addition of L-[U-14C]proline to suspensions metabolizing and synthesizing the pigment because of addition of alanine resulted in the incorporation of radioactive label into prodigiosin, as well as into cellular protein. Since Put mutants could not catabolize proline, the incorporation of [14C]proline into the prodigiosin molecule indicated that proline was incorporated directly into the pigment.

Alanine↗
PubMed1992

Enhancement by concanavalin A of the suppressive effect of prodigiosin 25-C on proliferation of murine splenocytes.

Proliferation of concanavalin A (Con A)-activated nylon-wool purified murine splenic T cells was increasingly suppressed by prodigiosin 25-C as higher concentrations of Con A were used for the activation. Enhancement of suppressive effect of prodigiosin 25-C was not observed when T cells were stimulated with phytohemagglutinin (PHA), anti-CD3 antibody, or allogeneic splenic adherent cells. The suppressive effect of prodigiosin 25-C was enhanced by the addition of Con A in various T cell subpopulations as well as in LPS-activated splenic B cells. Lectins that recognize mannose residue of biantennary-complex-type sugar chains significantly enhanced the suppressive effect of prodigiosin 25-C, whereas a lectin that binds to N-acetylglucosamine did not. These results suggest that binding of lectins to the mannose residue of biantennary-complex-type sugar chains on cell surface of both T and B lymphocytes plays a central role on the enhancement of the suppressive effect of prodigiosin 25-C.

Animals↗
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↗
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↗
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↗
PubMed1976

Incorporation of proline into prodigiosin by a Put mutant of Serratia marcesens.

A Put mutant of Serratia marcescens, deficient in proline oxidase and therefore unable to degrade proline, was used to assay for an enzymatic reaction responsible for incorporation of proline into prodigiosin. The reaction had a pH optimum of 7.5 and a Km of 1.1 X 10(-4) M at 27 C. At temperatures above 27 C, the velocity of the reaction decreased with increasing temperature and little activity was detected at 42 C. Activity of the enzyme was directly proportional to the quantity of pigment formed and was inhibited by thioproline, a substrate analog. These data suggested the presence of a unique and specific enzyme in the biosynthetic pathway for prodigiosin.

Alanine↗
PubMedDate not supplied

[Prodigiosin as a possible inhibitor of Serratia marcescens nuclease].

Preparations of prodigiosin inhibited the activity of nuclese of Serratia marcescens. The preparations were fractionated on an alumina column. The activity of nuclease was inhibited by both fractions containing pyrryldipyrrylmethene compounds and fractions in which these compounds were not found by spectrophotometry. The inhibitor was isolated also from the cells of a pigmentless strain. Therefore, the inhibition is exhibited by compounds that are extracted from the cells with acetone and petroleum ether, rather than by prodigiosin.

Deoxyribonucleases↗
PubMed1976

The reversal of glucose repressed prodigiosin production in Serratia marcescens by the cyclic 3'5'-adenosine monophosphate inhibitor theophylline.

Glucose was found to cause severe repression of prodigiosin production in Serratia marcescens and a dose related partial reversal was demonstrated by theophylline. It is suggested that this reversal is due to the inhibition of cAMP phosphodiesterase and the concomitant increase in cellular cAMP concentration.

Dose-Response Relationship, Drug↗
PubMedDate not supplied

[Correlation between the synthesis of extracellular proteases and the synthesis of the red pigment prodigiosin in Serratia marcescens].

A correlation has been established between synthesis of exocellular protease and synthesis of a red pigment prodigiosine by Serratia marcescens. Chloramphenicol, an inhibitor of protein synthesis, inhibits also synthesis of the pigment. Leucine, an inductor of synthesis of the exocellular protease by Serratia marcescens VI, induces also synthesis of the pigment. A mixture of 18 natural amino acids, asparagine and ammonium ions represses both synthesis of the enzyme and the pigment.

Chloramphenicol↗
PubMedDate not supplied

[Effect of the carbon/nitrogen ratio on the antibiotic activity of prodigiosin].

The antibacterical activity of prodigiosin varies according to the C/N ratio in the cultural media for S. marcescens. In organic media, as nutrient agar, peptone or soytone, the optimal ratio lies between 4 and 5, and higher values are required for "mineral media" where the nitrogen source is essentially an ammonium salt. The separate C source would be probably used as "acetate source" for the synthesis of the terminal alkylpyrrole.

Carbon↗
PubMed1976

Prodiginine (prodigiosin-like) pigments from Streptomyces and other aerobic Actinomycetes.

About 95 microorganisms, mainly streptomycetes, were examined for prodiginine pigments. The test methods, including some media for stimulating pigment production, are given. All nine strains which produced prodiginine pigments were characterized and the pigments identified. The results were used to propose structures for five prodigiosin-like pigments from actinomycetes reported in the literature between 1947 and 1964. Streptoverticillium sp. 26-1 furnished good yields of butylcycloheptylprodiginine (I), whose antimicrobial activity is given.

Actinomycetales↗