Abstract
A slightly halophilic myxobacterial strain, SMH-27-4, was isolated from nearshore soil and shown to belong to a new myxobacterium genus based on phylogenetic analysis. This slowly-growing myxobacterium produced the novel antibiotic depsipeptides miuraenamides A and B. Their physico-chemical properties and molecular formulas, C34H42N3O7Br and C34H42N3O7I, were determined. Miuraenamides A exhibited potent and selective inhibition against a phytopathogenic microorganism, Phytophthora sp., and moderate inhibition against some fungi and yeasts, but was ineffective against bacteria. Both of the metabolites inhibited NADH oxidase at IC50 values of 50 μM, suggesting, like β-methoxyacrylate-type antibiotics, the electron transfer system of the mitochondrial respiratory chain as the cellular target.
Similar content being viewed by others
Article PDF
References
Reichenbach H, Höfle G . Production of Bioactive Secondary Metabolites. In: Dworkin M, Kaiser D (eds). Myxobacteria II. American Society for Microbiology, Washington DC, pp. 347–397 ( 1993)
Reichenbach H, Gerth K, Irschik H, Kunze B, Höfle G . Myxobacteria: a source of new antibiotics. Trends Biotechnol 6: 115–121 ( 1988)
Reichenbach H, Höfle G . Myxobacteria as Producers of Secondary Metabolites. In: Grabley S, Thiericke R (eds). Drug Discovery from Nature. Springer, Berlin, pp. 149–179 ( 1999)
Gerth K, Pradella S, Perlova O, Beyer S, Müller R . Myxobacteria: proficient producers of novel natural products with various biological activities—past and future biotechnological aspects with the focus on the genus Sorangium. J Biotechnol 106: 233–253 ( 2003)
Iizuka T, Jojima Y, Fudou R, Yamanaka S . Isolation of myxobacteria from the marine environment. FEMS Microbiol Lett 169: 317–322 ( 1998)
Fudou R, Iizuka T, Yamanaka S . Haliangicin, a novel antifungal metabolite produced by a marine myxobacterium. 1. Fermentation and biological characteristics. J Antibiot 54: 149–152 ( 2001)
Fudou R, Iizuka T, Sato S, Ando T, Shimba N, Yamanaka S . Haliangicin, a novel antifungal metabolite produced by a marine myxobacterium. 2. Isolation and structural elucidation. J Antibiot 54: 153–156 ( 2001)
Kundim BA, Itou Y, Sakagami Y, Fudou R, Iizuka T, Yamanaka S, Ojika M . New haliangicin isomers, potent antifungal metabolites produced by a marine myxobacterium. J Antibiot 56: 630–638 ( 2003)
Ojika M, Suzuki Y, Tsukamoto A, Sakagami Y, Fudou R, Yoshimura T, Yamanaka S . Cystothiazoles A and B, new bithiazole-type antibiotics from the myxobacterium Cystobacter fuscus. J Antibiot 51: 275–281 ( 1998)
Suzuki Y, Ojika M, Sakagami Y, Fudou R, Yamanaka S . Cystothiazoles C~F, new bithiazole-type antibiotics from the myxobacterium Cystobacter fuscus. Tetrahedron 54: 11399–11404 ( 1998)
Akita H, Sasaki T, Kato K, Suzuki Y, Kondo K, Sakagami Y, Ojika M, Fudou R, Yamanaka S . (+)-Cystothiazole G: isolation and structural elucidation. Tetrahedron 60: 4735–4738 ( 2004)
Kundim BA, Itou Y, Sakagami Y, Fudou R, Yamanaka S, Ojika M . Novel antifungal polyene amides from the myxobacterium Cystobacter fuscus: isolation, antifungal activity and absolute structure determination. Tetrahedron 60: 10217–10221 ( 2004)
Thierbach G, Reichenbach H . Myxothiazol, a new inhibitor of the cytochrome b-c1 segment of the respiratory chain. Biochim Biophys Acta 638: 282–289 ( 1981)
Fang J, Beattie DS . External alternative NADH dehydrogenase of Saccharomyces cervisiae: a potential source of superoxide. Free Radic Biol Med 34: 478–488 ( 2003)
Iizuka T, Jojima Y, Fudou R, Hiraishi A, Ahn J-W, Yamanaka S . Plesiocystis pacifica gen. nov., sp. nov., a marine myxobacterium that contains dihydrogenated menaquinone, isolated from the Pacific coasts of Japan. Int J Syst Evol Microbiol 53: 189–195 ( 2003)
Iizuka T, Jojima Y, Fudou R, Tokura M, Hiraishi A, Yamanaka S . Enhygromyxa salina gen. nov., sp. nov., a slightly halophilic myxobacterium isolated from the coastal areas of Japan. Syst Appl Microbiol 26: 189–196 ( 2003)
Sauter H, Steglich W, Anke T . Strobilurins: evolution of a new class of active substances. Angew Chem Int Ed 38: 1328–1349 ( 1999)
Sasse F, Leibold T, Kunze B, Höfle G, Reichenbach H . Cyrmenins, new β-methoxyacrylate inhibitors of the electron transport. Production, isolation, physico-chemical and biological properties. J Antibiot 56: 827–831 ( 2003)
Leibold T, Sasse F, Reichenbach H, Höfle G . Cyrmenins, novel antifungal peptides containing a nitrogen-linked β-methoxyacrylate pharmacophore: Isolation and structural elucidation. Eur J Org Chem 431–435 ( 2004)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Iizuka, T., Fudou, R., Jojima, Y. et al. Miuraenamides A and B, Novel Antimicrobial Cyclic Depsipeptides from a New Slightly Halophilic Myxobacterium: Taxonomy, Production, and Biological Properties. J Antibiot 59, 385–391 (2006). https://doi.org/10.1038/ja.2006.55
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/ja.2006.55
Keywords
This article is cited by
-
Highlights of marine natural products having parallel scaffolds found from marine-derived bacteria, sponges, and tunicates
The Journal of Antibiotics (2020)
-
Actin stabilizing compounds show specific biological effects due to their binding mode
Scientific Reports (2019)
-
Transcriptional effects of actin-binding compounds: the cytoplasm sets the tone
Cellular and Molecular Life Sciences (2018)
-
Persistent inhibition of pore-based cell migration by sub-toxic doses of miuraenamide, an actin filament stabilizer
Scientific Reports (2017)
-
Molecular and functional characterization of myxobacteria isolated from soil in India
3 Biotech (2017)