The Myxocoumarins A and B from Stigmatella Aurantiaca Strain MYX-030

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2013 Dec 25

PMID 24367422

Citations 5

Authors

Tobias A M Gulder

Snezana Neff

Traugott Schuz

Tammo Winkler

Rene Gees

Bettina Bohlendorf

Affiliations

Soon will be listed here.

Abstract

The myxobacterial strain Stigmatella aurantiaca MYX-030 was selected as promising source for the discovery of new biologically active natural products by our screening methodology. The isolation, structure elucidation and initial biological evaluation of the myxocoumarins derived from this strain are described in this work. These compounds comprise an unusual structural framework and exhibit remarkable antifungal properties.

Citing Articles

Synthesis and antibiotic potential of myxocoumarin-inspired chromene dione analogs.

Behnsen A, Hertrampf G, Vojnovic S, Nikodinovic-Runic J, Gulder T RSC Adv. 2024; 14(47):35215-35219.

PMID: 39502864 PMC: 11536209. DOI: 10.1039/d4ra05941g.

Epitope Mapping of Pathogenic Autoantigens on Sjögren's Syndrome-Susceptible Human Leukocyte Antigens Using In Silico Techniques.

Gupta S, Li D, Ostrov D, Nguyen C J Clin Med. 2022; 11(6).

PMID: 35330015 PMC: 8953074. DOI: 10.3390/jcm11061690.

Strong Antibiotic Activity of the Myxocoumarin Scaffold in vitro and in vivo.

Hertrampf G, Kusserow K, Vojnovic S, Pavic A, Muller J, Nikodinovic-Runic J Chemistry. 2022; 28(32):e202200394.

PMID: 35229915 PMC: 9321099. DOI: 10.1002/chem.202200394.

Myxobacteria as a Source of New Bioactive Compounds: A Perspective Study.

Bhat M, Mishra A, Bhat M, Banday M, Bashir O, Rather I Pharmaceutics. 2021; 13(8).

PMID: 34452226 PMC: 8401837. DOI: 10.3390/pharmaceutics13081265.

Biosynthesis of α-pyrones.

Schaberle T Beilstein J Org Chem. 2016; 12:571-88.

PMID: 27340449 PMC: 4901931. DOI: 10.3762/bjoc.12.56.

References

Cantrell C, Dayan F, Duke S . Natural products as sources for new pesticides. J Nat Prod. 2012; 75(6):1231-42. DOI: 10.1021/np300024u. View

Weissman K, Muller R . Myxobacterial secondary metabolites: bioactivities and modes-of-action. Nat Prod Rep. 2010; 27(9):1276-95. DOI: 10.1039/c001260m. View

Nett M, Konig G . The chemistry of gliding bacteria. Nat Prod Rep. 2007; 24(6):1245-61. DOI: 10.1039/b612668p. View

van Pee K, Ligon J . Biosynthesis of pyrrolnitrin and other phenylpyrrole derivatives by bacteria. Nat Prod Rep. 2000; 17(2):157-64. DOI: 10.1039/a902138h. View

Friedrich T, van Heek P, Leif H, Ohnishi T, Forche E, Kunze B . Two binding sites of inhibitors in NADH: ubiquinone oxidoreductase (complex I). Relationship of one site with the ubiquinone-binding site of bacterial glucose:ubiquinone oxidoreductase. Eur J Biochem. 1994; 219(1-2):691-8. DOI: 10.1111/j.1432-1033.1994.tb19985.x. View

Cragg G, Newman D, SNADER K . Natural products in drug discovery and development. J Nat Prod. 1997; 60(1):52-60. DOI: 10.1021/np9604893. View

Wenzel S, Muller R . The biosynthetic potential of myxobacteria and their impact in drug discovery. Curr Opin Drug Discov Devel. 2009; 12(2):220-30. View

Gerth K, Bedorf N, Hofle G, Irschik H, Reichenbach H . Epothilons A and B: antifungal and cytotoxic compounds from Sorangium cellulosum (Myxobacteria). Production, physico-chemical and biological properties. J Antibiot (Tokyo). 1996; 49(6):560-3. DOI: 10.7164/antibiotics.49.560. View

Reichenbach H, Hofle G . Discovery and development of the epothilones : a novel class of antineoplastic drugs. Drugs R D. 2007; 9(1):1-10. PMC: 7044396. DOI: 10.2165/00126839-200809010-00001. View

10.

Gerth K, Bedorf N, Irschik H, Hofle G, Reichenbach H . The soraphens: a family of novel antifungal compounds from Sorangium cellulosum (Myxobacteria). I. Soraphen A1 alpha: fermentation, isolation, biological properties. J Antibiot (Tokyo). 1994; 47(1):23-31. DOI: 10.7164/antibiotics.47.23. View

11.

Newman D, Cragg G, Snader K . Natural products as sources of new drugs over the period 1981-2002. J Nat Prod. 2003; 66(7):1022-37. DOI: 10.1021/np030096l. View

12.

Copping L, Duke S . Natural products that have been used commercially as crop protection agents. Pest Manag Sci. 2007; 63(6):524-54. DOI: 10.1002/ps.1378. View

13.

Wenzel S, Muller R . Myxobacterial natural product assembly lines: fascinating examples of curious biochemistry. Nat Prod Rep. 2007; 24(6):1211-24. DOI: 10.1039/b706416k. View

14.

Kunze B, Hofle G, Reichenbach H . The aurachins, new quinoline antibiotics from myxobacteria: production, physico-chemical and biological properties. J Antibiot (Tokyo). 1987; 40(3):258-65. DOI: 10.7164/antibiotics.40.258. View

15.

Gerth K, Irschik H, Reichenbach H, Trowitzsch W . Myxothiazol, an antibiotic from Myxococcus fulvus (myxobacterales). I. Cultivation, isolation, physico-chemical and biological properties. J Antibiot (Tokyo). 1980; 33(12):1474-9. DOI: 10.7164/antibiotics.33.1474. View

16.

Reichenbach H . Myxobacteria, producers of novel bioactive substances. J Ind Microbiol Biotechnol. 2002; 27(3):149-56. DOI: 10.1038/sj.jim.7000025. View

17.

Thierbach G, Reichenbach H . Myxothiazol, a new inhibitor of the cytochrome b-c1 segment of th respiratory chain. Biochim Biophys Acta. 1981; 638(2):282-9. DOI: 10.1016/0005-2728(81)90238-3. View

18.

Hofle G, Irschik H . Isolation and biosynthesis of aurachin P and 5-nitroresorcinol from Stigmatella erecta. J Nat Prod. 2008; 71(11):1946-8. DOI: 10.1021/np800325z. View

19.

Newman D, Cragg G . Natural products as sources of new drugs over the 30 years from 1981 to 2010. J Nat Prod. 2012; 75(3):311-35. PMC: 3721181. DOI: 10.1021/np200906s. View

20.

Tripathi R, Gottlieb D . Mechanism of action of the antifungal antibiotic pyrrolnitrin. J Bacteriol. 1969; 100(1):310-8. PMC: 315394. DOI: 10.1128/jb.100.1.310-318.1969. View