Acremonium zeae, a protective endophyte of maize, produces dihydroresorcylide and 7-hydroxydihydroresorcylides

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 9, 2008, Pages 3006-3009

  Poling, Stephen M ^a   Wicklow, Donald T ^a   Rogers, Kristina D ^b   Gloer, James B ^b  

^a NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

^b University of Iowa   (United States)

Author keywords

7 hydroxydihydroresorcylide; Acremonium zeae; Dihydroresorcylide; Maize; Pyrrocidine

Indexed keywords

2 PYRROLIDONE DERIVATIVE; 7 HYDROXYDIHYDRORESORCYLIDE; 7-HYDROXYDIHYDRORESORCYLIDE; BRIDGED COMPOUND; DIHYDRORESORCYLIDE; FUNGICIDE; MACROLIDE; PYRROCIDINE A; PYRROCIDINE B;

ACREMONIUM; ARTICLE; CHEMISTRY; MAIZE; METABOLISM; MICROBIOLOGY; PLANT SEED; STEREOISOMERISM;

ACREMONIUM; BRIDGED COMPOUNDS; FUNGICIDES, INDUSTRIAL; MACROLIDES; PYRROLIDINONES; SEEDS; STEREOISOMERISM; ZEA MAYS;

ACREMONIUM (ASCOMYCOTA); ACREMONIUM ZEAE; FUNGI; ZEA MAYS;

EID: 44349149466     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf073274f     Document Type: Article

References (16)

1. Wicklow, D. T.; Roth, S.; Deyrup, S. T.; Gloer, J. B. A protective endophyte of maize: Acremonium zeae antibiotics inhibitory to Aspergillus flavus and Fusarium verticillioides. Mycol. Res. 2005, 109, 610-618.
2. Bigelis, R.; He, H.; Yang, H. Y.; Chang, L. P.; Greenstein, M. Production of fungal antibiotics using polymeric solid supports in solid-state and liquid fermentation. J. Ind. Microbiol. Biotechnol. 2006, 33, 815-826.
3. He, H.; Yang, H. Y.; Bigelis, R.; Solum, E. H.; Greenstein, M.; Carter, G. T. Pyrrocidines A and B, new antibiotics produced by a filamentous fungus. Tetrahedron Lett. 2002, 43, 1633-1636.
4. Wicklow, D. T.; Poling, S. M. Antimicrobial activity of pyrrocidines from Acremonium zeae against endophytes and pathogens of maize. Phytopathology 2006, 96, S122.
5. Mudur, S. V.; Gloer, J. B.; Wicklow, D. T. Sporminarins A and B: antifungal metabolites from a fungicolous isolate of Sporormiella minimoides. J. Antibiot. 2006, 59, 500-506.
6. Sugawara, F.; Strobel, G.; Fisher, L. E.; Van Duyne, G. D.; Clardy, J. Bipolaroxin, a selective Phytotoxin produced by Bipolaris cynodontis. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 8291-8294.
7. Godoy, G.; Steadman, J. R.; Dickman, M. B.; Dam, R. Use of mutants to demonstrate the role of oxalic acid in pathogenicity of Sclerotinia sclerotiorum on Phaseolus vulgaris. Physiol. Mol. Plant Pathol. 1990, 37, 179-191.
8. Ghisalberti, E. L.; Hockless, D. C. R.; Rowland, C. Y.; White, A. H. Structural study of curvularin, a cell division inhibitor. Aust. J. Chem. 1993, 46, 571-575.
9. Oyama, H.; Sassa, T.; Ikeda, M. Structures of new plant growth inhibitors trans- and cis-resorcylide. Agric. Biol. Chem. 1978, 42, 2407-2409.
10. Couladouros, E. A.; Mihou, A. P.; Bouzas, E. A. First total synthesis of trans- and cis-resorcylide: remarkable hydrogen-bond-controlled, stereospecific ring-closing metathesis. Org. Lett. 2004, 6, 977-980.
11. Barrow, C. J. New macrocyclic lactones from a Penicillium species. J. Nat. Prod. 1997, 60, 1023-1025.
12. Lai, S.; Shizuri, Y.; Yamamura, S.; Kawai, K.; Terada, Y.; Furukawa, H. Novel curvularin-type metabolites of a hybrid strain ME 005 derived from Penicillium citreo-viride B. IFO 6200 and 4692. Tetrahedron Lett. 1989, 30, 2241-2244.
13. Nukina, M.; Sassa, T.; Oyama, H.; Ikeda, M. Structures and biological activities of fungal macrolides, pyrenolide and resorcylide. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 22nd 1979, 36, 2-9 (in Japanese).
14. Fu, Y. Isolation and characterization of novelphytotoxins from pathogenic fungi. Ph.D. thesis, Cornell University, Ithaca, NY, 1989.
15. West, R. R.; Martinez, T.; Franklin, H. R.; Bishop, P. D.; Rassing, B. R. Factor XIIIA inhibitor. U.S. Patent 5,710,174, 1998.
16. Sassa, T.; Nukina, M.; Ikeda, M. Electrophilic reactivities and biological activities of trans- and cis-resorcylides. Nippon Kagaku Kaishi 1981, 883, 885.