Myxochelin A, a new iron-chelating compound from Angiococcus disciformis (myxobacterales). Production, isolation, physico-chemical and biological properties.

Kunze, Brigitte; Bedorf, Norbert; Köhl, Werner; Höfle, Gerhard; Reichenbach, Hans

doi:10.7164/antibiotics.42.14

Cited by 94 publications

(76 citation statements)

References 8 publications

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“…The migration of colon 26-L5 cells was not inhibited by (S)-1 ( Fig. 4d), indicating that (S)-1 may act on the molecule(s) related to cell adhesion or Myxochelin A (1) has been reported to show antibacterial [5] and antioxidative [10] activities, and these activities are attributed to catecholate (2,3-dihydroxybenzoate) moiety. There are a number of microbial secondary metabolites containing the catecholate group(s), and many of them are classified as siderophores which function in the producing microorganism to acquire ferric ions from the environment.…”

Section: Bioactivitymentioning

confidence: 99%

“…Although 1 is found from myxobacterial strains such as Angiococcus [5] and Stigmatella [6], this is the first example of isolation of 1 from actinomycetes. In the original paper reported by Kunze et al [5], there is no description of specific rotation and absolute configuration, and to our knowledge no report on the absolute structure exists after the first publication. Inconsistently, the R configuration is indicated for 1 in the Dictionary of Natural Products although no literatures are cited for the determination of the absolute configuration.…”

Section: Screening and Structure Determinationmentioning

confidence: 99%

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Absolute Configuration and Antitumor Activity of Myxochelin A Produced by Nonomuraea pusilla TP-A0861†

et al. 2006

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In the screening of antitumor compounds from microbial secondary metabolites, myxochelin A was isolated from a culture broth of Nonomuraea pusilla TP-A0861. The absolute configuration was determined to be S by synthesizing both enantiomers from an L-or D-lysine derivative and comparing their specific rotations. Both enantiomers of myxochelin A showed remarkable inhibitory effects on the invasion of murine colon 26-L5 carcinoma cells at non-cytotoxic concentrations. Keywords myxochelin A, invasion, antitumor, Nonomuraea IntroductionTumor invasion is the major cause of treatment failure and death in cancer patients. The process of invasion into the basement membrane is a cascade of sequential complex steps, mainly consisting of tumor cell adhesion, enzymatic degradation of extracellular matrix proteins, and migration [1]. Compounds that inhibit any of these steps are expected to be candidates of anti-metastatic and/or anti-invasive agents. Hence, the clinical efficacy of such invasive inhibitors in cancer chemotherapy are extensively exploited [2,3].In the screening for anti-invasive compounds from natural products, myxochelin A (1) was found to inhibit the in vitro tumor cell invasion. Herein, we describe the isolation, structure determination, synthesis and biological properties of 1. Results and Discussion Screening and Structure DeterminationThe screening method employed in this study is based on the experimental model of tumor cell invasion using Transwell cell culture chamber and Matrigel, the reconstituted basement membrane [4]. This bioassay enables the detection of compounds that inhibit cell adhesion, enzymatic degradation of extracellular matrix, or migration. While screening for anti-invasive compounds from our natural products library, significant activity was shown by myxochelin A (1, Fig. 1

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Section: Bioactivitymentioning

confidence: 99%

Section: Screening and Structure Determinationmentioning

confidence: 99%

Absolute Configuration and Antitumor Activity of Myxochelin A Produced by Nonomuraea pusilla TP-A0861†

et al. 2006

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“…For example S. aurantiaca strain DW4/3-1 simultaneously produces the electron transport inhibitor myxothiazol [1], the dawenols [2], the myxochromides [3], and the iron chelators myxochelin A and B [4,5]. In culture extracts of S. aurantiaca, strain Sg a15 even five structurally entirely different groups of metabolites have been discovered, namely the inhibitors of the eukaryotic electron transport, the aurachins [6], stigmatellins [7,8], and myxalamids [7,9,10], and as in strain DW4/3-1 also the myxochelins [5] and minor amounts of myxochromides components [3].…”

Section: Introductionmentioning

confidence: 99%

Aurafuron A and B, New Bioactive Polyketides from Stigmatella aurantiaca and Archangium gephyra (Myxobacteria)

et al. 2005

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New antibiotic polyketides, named aurafuron A (1) and B (2) were isolated from culture extracts of myxobacteria of the species Stigmatella aurantiaca and Archangium gephyra, strain Ar 10844. By multi-step chromatography 1 and 2 were separated from a variety of other non-related co-metabolites, and their structures elucidated by spectroscopic methods as new 5-alkenyl-3 3(2H)-furanones. Aurafurons inhibited the growth of some filamentous fungi and additionally, aurafuron B was weakly active against few Gram-positive bacteria. Both compounds also showed cytotoxic activity against the mouse fibroblast cell line L929.

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“…It seems probable that enterobactin is biosynthesized in streptomycetes via a NRPS pathway, similar to the well-characterized Escherichia coli pathway, and that this pathway is distinct from that for desferrioxamine biosynthesis (48). A third potential example of multiple siderophore production by Streptomyces species has been uncovered through preliminary examination of the S. avermitilis genome sequence, which, in addition to a cluster of genes virtually identical to the des cluster of S. coelicolor, contains a gene cluster encoding a NRPS system predicted to produce a siderophore of similar structure to the myxobacterial siderophore myxochelin (11,49). Thus, the production of structurally diverse secondary nonribosomally synthesized peptide siderophores, in addition to the characteristic desferrioxamine siderophores, may be common in streptomycetes.…”

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confidence: 99%

Synergy and contingency as driving forces for the evolution of multiple secondary metabolite production by Streptomyces species

Challis

Hopwood

2003

Proc. Natl. Acad. Sci. U.S.A.

544

398

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In this article we briefly review theories about the ecological roles of microbial secondary metabolites and discuss the prevalence of multiple secondary metabolite production by strains of Streptomyces, highlighting results from analysis of the recently sequenced Streptomyces coelicolor and Streptomyces avermitilis genomes. We address this question: Why is multiple secondary metabolite production in Streptomyces species so commonplace? We argue that synergy or contingency in the action of individual metabolites against biological competitors may, in some cases, be a powerful driving force for the evolution of multiple secondary metabolite production. This argument is illustrated with examples of the coproduction of synergistically acting antibiotics and contingently acting siderophores: two well-known classes of secondary metabolite. We focus, in particular, on the coproduction of ␤-lactam antibiotics and ␤-lactamase inhibitors, the coproduction of type A and type B streptogramins, and the coregulated production and independent uptake of structurally distinct siderophores by species of Streptomyces. Possible mechanisms for the evolution of multiple synergistic and contingent metabolite production in Streptomyces species are discussed. It is concluded that the production by Streptomyces species of two or more secondary metabolites that act synergistically or contingently against biological competitors may be far more common than has previously been recognized, and that synergy and contingency may be common driving forces for the evolution of multiple secondary metabolite production by these sessile saprophytes.

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Myxochelin A, a new iron-chelating compound from Angiococcus disciformis (myxobacterales). Production, isolation, physico-chemical and biological properties.

Cited by 94 publications

References 8 publications

Absolute Configuration and Antitumor Activity of Myxochelin A Produced by Nonomuraea pusilla TP-A0861†

Absolute Configuration and Antitumor Activity of Myxochelin A Produced by Nonomuraea pusilla TP-A0861†

Aurafuron A and B, New Bioactive Polyketides from Stigmatella aurantiaca and Archangium gephyra (Myxobacteria)

Synergy and contingency as driving forces for the evolution of multiple secondary metabolite production by Streptomyces species

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