Novel oxidized derivatives of antifungal pyrrolnitrin from the bacterium Burkholderia cepacia K87

Journal of Antibiotics

Volumn 61, Issue 7, 2008, Pages 420-425

  Sultan, Md Zakir ^a   Park, Kyungseok ^b   Lee, Sang Yeob ^b   Park, Jung Kon ^c   Varughese, Titto ^a   Moon, Surk Sik ^a  

^a Kongju National University   (South Korea)

^b National Institute of Animal Science   (South Korea)

^c Arysta Life Science Korea   (South Korea)

Author keywords

3 chloro 4 (3 chloro 2 nitrophenyl) 5 methoxy 3 pyrrolin 2 one; 4 chloro 3 (3 chloro 2 nitrophenyl) 5 methoxy 3 pyrrolin 2 one; Burkholderia cepacia K87; Metabolite; Pyrrolnitrin

Indexed keywords

3 CHLORO 4 (3 CHLORO 2 NITROPHENYL) 5 METHOXY 3 PYRROLIN 2 ONE; 4 CHLORO 3 (3 CHLORO 2 NITROPHENYL) 5 METHOXY 3 PYRROLIN 2 ONE; ANTIFUNGAL AGENT; PYRROLE DERIVATIVE; PYRROLNITRIN; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; BURKHOLDERIA CEPACIA; DRUG SCREENING; NONHUMAN; OXIDATION; PRIORITY JOURNAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HYPHOMYCETES; ISOLATION AND PURIFICATION; MICROBIOLOGICAL EXAMINATION; MICROBIOLOGY;

BACTERIA (MICROORGANISMS); BURKHOLDERIA CEPACIA; THANATEPHORUS CUCUMERIS;

ANTIFUNGAL AGENTS; BURKHOLDERIA CEPACIA; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PYRROLNITRIN; RHIZOCTONIA; SOIL MICROBIOLOGY;

EID: 55449087150     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2008.58     Document Type: Article

References (21)

1. Ōmura S. The search for bioactive compounds from microorganisms; Springer-Verlag, New York, pp. 1-107 and 213-223 (1992)
2. van Veen JA, van Overbeek LS, van Elsas JD. Fate and activity of microorganisms introduced into soil. Microbiol Mol Biol Rev 61: 121-135 (1997)
3. Whipps JM. Microbial interactions and biocontrol in the rhizosphere. J Exp Bot 52: 487-511 (2001)
4. Thomashow LS. Biological control of plant root pathogens. Curr Opin Biotechnol 7: 343-347 (1996)
5. Leisinger T, Margraff R. Secondary metabolites of the fluorescent pseudomonads. Microbiol Rev 43: 422-442 (1979)
6. Moon SS, Kang PM, Park KS, Kim CH. Plant growth promoting and fungicidal 4-quinolinones from Pseudomonas cepacia. Phytochemistry 42: 365-368 (1996)
7. Moon SS, Kang PM, Kim BS, Hwang BK. Spectral evidence of 1,2-linkage in antifungal rhamnolipid produced by Pseudomonas aeruginosa. Bull Korean Chem Soc 17: 291-293 (1996)
8. Coenye T, Vandamme P, Govan JRW, Lipuma JJ. Taxonomy and identification of the Burkholderia cepacia complex. J Clin Microbiol 39: 3427-3436 (2001)
9. Arima K, Imanaka H, Kousaka M, Fukuda A, Tamura G. Studies on pyrrolnitrin, a new antibiotic. I. Isolation and properties of pyrrolnitrin. J Antibiot 18: 201-204 (1965)
10. Burkhead KD, Schisler DA, Slininger PJ. Pyrrolnitrin production by biological control agent Pseudomonas cepacia b37w in culture and in colonized wounds of potatoes. Appl Environ Microbiol 60: 2031-2039 (1994)
11. El-Banna N, Winkelmann G. Pyrrolnitrin from Burkholderia cepacia: antibiotic activity against fungi and novel activities against streptomycetes. J Appl Microbiol 85: 69-78 (1998)
12. Morimoto Y, Hashimoto M, Hattori K. The crystal structure of pyrrolnitrin. Tetrahedron Lett 9: 209-211 (1968)
13. Cain CC, Lee D, Waldo III RH, Henry AT, Casida EJ Jr, Wani MC, Wall ME, Oberlies NH, Falkinham III JO. Synergistic antimicrobial activity of metabolites produced by a nonobligate bacterial predator. Antimicrob Agents Chemother 47: 2113-2117 (2003)
14. Levenfors JJ, Hedman R, Thaning C, Gerhardson B, Welch CJ. Broad-spectrum antifungal metabolites produced by the soil bacterium Serratia plymuthica A 153. Soil Biol Biochem 36: 677-685 (2004)
15. Hwang J, Chilton WS, Benson DM. Pyrrolnitrin production by Burkholderia cepacia and biocontrol of rhizoctonia stem rot of poinsettia. Biol Control 25: 56-63 (2002)
16. Murphy PJ, Williams TL. Biological inactivation of pyrrolnitrin. Identification and synthesis of pyrrolnitrin metabolites. J Med Chem 15: 137-139 (1972)
17. Godfrey CRA. Agrochemicals from natural products; Marcel Dekker, Inc., New York, pp. 322-324 (1994)
18. Sako M, Kihara T, Tanisaki M, Maki Y, Miyamae A, Azuma T, Kohda S, Masugi T. Novel photodegradation of the antifungal antibiotic pyrrolnitrin in anhydrous and aqueous aprotic solvents. J Org Chem 67: 668-673 (2002)
19. Greatrex BW, Kimber MC, Taylor DK, Fallon G, Tiekink ERT. 1,2-dioxines as masked cis γ-hydroxy enones and their versatility in the synthesis of highly substituted γ-lactones. J Org Chem 67: 5307-5314 (2002)
20. Herz W, Juo RR. Photooxygenation of 1-vinylcycloalkenes. The competition between "ene" reaction and cycloaddition of singlet oxygen. J Org Chem 50: 618-627 (1985)
21. II- tetraphenylporphyrin-catalyzed decomposition of bicyclic endoperoxides: a new approach to substituted furofuran systems. Eur J Org Chem 2000: 1359-1363 (2000)