Ether bridge formation in loline alkaloid biosynthesis

Phytochemistry

Volumn 98, Issue , 2014, Pages 60-68

  Pan, Juan ^a   Bhardwaj, Minakshi ^a   Faulkner, Jerome R ^a,c   Nagabhyru, Padmaja ^a   Charlton, Nikki D ^b   Higashi, Richard M ^a   Miller, Anne Frances ^a   Young, Carolyn A ^b   Grossman, Robert B ^a   Schardl, Christopher L ^a  

^a UNIVERSITY OF KENTUCKY   (United States)

^b PLANT BIOLOGY DIVISION   (United States)

^c USDA NRCS   (United States)

Author keywords

Clavicipitaceae; Epichlo spp.; exo 1 Acetamidopyrrolizidine; Genome sequencing; Grass symbionts; Loline alkaloids; lolO; Oxoglutarate iron dependent dioxygenase; Pyrrolizidines

Indexed keywords

CLAVICIPITACEAE; EPICHLOE; FUNGI; POACEAE;

ALKALOID; ETHER DERIVATIVE; IRON(II) OXYGENASE; LOLINE; OXYGENASE;

BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM;

ALKALOIDS; ETHERS; MOLECULAR STRUCTURE; OXYGENASES;

EID: 84892928323     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2013.11.015     Document Type: Article

References (32)

1. Z.-Q. An, M.R. Siegel, W. Hollin, H.-F. Tsai, D. Schmidt, and C.L. Schardl Relationships among non-Acremonium sp. fungal endophytes in five grass species Appl. Environ. Microbiol. 59 1993 1540 1548 (Pubitemid 23141168)
2. R.M. Andrie, J.P. Martinez, and L.M. Ciuffetti Development of ToxA and ToxB promoter-driven fluorescent protein expression vectors for use in filamentous ascomycetes Mycologia 97 2005 1152 1161 (Pubitemid 43345375)
3. A. Bacetty, M. Snook, A. Glenn, J. Noe, P. Nagabhyru, and C. Bacon Chemotaxis disruption in Pratylenchus scribneri by tall fescue root extracts and alkaloids J. Chem. Ecol. 35 2009 844 850
4. J.D. Blankenship, M.J. Spiering, H.H. Wilkinson, F.F. Fannin, L.P. Bush, and C.L. Schardl Production of loline alkaloids by the grass endophyte, Neotyphodium uncinatum, in defined media Phytochemistry 58 2001 395 401 (Pubitemid 32851726)
5. J.D. Blankenship, J.B. Houseknecht, S. Pal, L.P. Bush, R.B. Grossman, and C.L. Schardl Biosynthetic precursors of fungal pyrrolizidines, the loline alkaloids ChemBioChem 6 2005 1016 1022 (Pubitemid 40825342)
6. T.L. Bultman, G. Bell, and W.D. Martin A fungal endophyte mediates reversal of wound-induced resistance and constrains tolerance in a grass Ecology 85 2004 679 685 (Pubitemid 38398281)
7. N.D. Charlton, K.D. Craven, S. Mittal, A.A. Hopkins, and C.A. Young Epichloë canadensis, a new interspecific epichloid hybrid symbiotic with Canada wildrye (Elymus canadensis) Mycologia 104 2012 1187 1199
8. C. Christine, K. Ikhiri, A. Ahond, A.A. Mourabit, C. Poupat, and P. Potier Synthèse des 1-amidopyrrolizidines naturelles, absouline et laburnamine, de dérivés et d'analogues pyrrolidinoimidazoliques Tetrahedron 56 2000 1837 1850 (Pubitemid 30176425)
9. K.R. Chung, and C.L. Schardl Vegetative compatibility between and within Epichloë species Mycologia 89 558-565 1997 976
10. P. Dominguez de Maria, R.W. van Gemert, A.J. Straathof, and U. Hanefeld Biosynthesis of ethers: unusual or common natural events? Nat. Prod. Rep. 27 2010 370 392
11. J.R. Faulkner, S.R. Hussaini, J.D. Blankenship, S. Pal, B.M. Branan, R.B. Grossman, and C.L. Schardl On the sequence of bond formation in loline alkaloid biosynthesis ChemBioChem 7 2006 1078 1088 (Pubitemid 44049443)
12. C. Hoveland Importance and economic significance of the Acremonium endophytes to performance of animals and grass plants Agric. Ecosyst. Environ. 44 1993 3 12 (Pubitemid 24411074)
13. J.G. Jensen, A.J. Popay, and B.A. Tapper Argentine stem weevil adults are affected by meadow fescue endophyte and its loline alkaloids N. Z. Plant Prot. 62 2009 12 18
14. B.L. Kutil, C. Greenwald, G. Liu, M.J. Spiering, C.L. Schardl, and H.H. Wilkinson Comparison of loline alkaloid gene clusters across fungal endophytes: predicting the co-regulatory sequence motifs and the evolutionary history Fungal Genet. Biol. 44 2007 1002 1010 (Pubitemid 47321238)
15. G.C.M. Latch, and M.J. Christensen Artificial infections of grasses with endophytes Ann. Appl. Biol. 107 1985 17 24
16. M. Omacini, E.J. Chaneton, C.M. Ghersa, and C.B. Muller Symbiotic fungal endophytes control insect host-parasite interaction webs Nature 409 2001 78 81 (Pubitemid 32098627)
17. D.G. Panaccione, R.D. Johnson, J. Wang, C.A. Young, P. Damrongkool, B. Scott, and C.L. Schardl Elimination of ergovaline from a grass-Neotyphodium endophyte symbiosis by genetic modification of the endophyte Proc. Natl. Acad. Sci. U.S.A. 98 2001 12820 12825 (Pubitemid 33020028)
18. A.J. Popay, B.A. Tapper, and C. Podmore Endophyte-infected meadow fescue and loline alkaloids affect Argentine stem weevil larvae N. Z. Plant Prot. 62 2009 19 27
19. W.E. Riedell, R.E. Kieckhefer, R.J. Petroski, and R.G. Powell Naturally occurring and synthetic loline alkaloid derivatives: insect feeding behavior modification and toxicity J. Entomol. Sci. 26 1991 122 129
20. J.A. Rudgers, and K. Clay An invasive plant-fungal mutualism reduces arthropod diversity Ecol. Lett. 11 2008 831 840 (Pubitemid 351991468)
21. C.L. Schardl A global view of metabolites Chem. Biol. (Oxford, UK) 13 2006 5 6 (Pubitemid 43099917)
22. C.L. Schardl, A. Leuchtmann, and M.J. Spiering Symbioses of grasses with seedborne fungal endophytes Annu. Rev. Plant Biol. 55 2004 315 340 (Pubitemid 38940935)
23. C.L. Schardl, R.B. Grossman, P. Nagabhyru, J.R. Faulkner, and U.P. Mallik Loline alkaloids: currencies of mutualism Phytochemistry 68 2007 980 996 (Pubitemid 46415759)
24. C.L. Schardl, C.A. Young, J.R. Faulkner, S. Florea, and J. Pan Chemotypic diversity of epichloae, fungal symbionts of grasses Fungal Ecol. 5 2012 331 344
25. C.L. Schardl, C.A. Young, U. Hesse, S.G. Amyotte, K. Andreeva, P.J. Calie, D.J. Fleetwood, D.C. Haws, N. Moore, B. Oeser, D.G. Panaccione, K.K. Schweri, C.R. Voisey, M.L. Farman, J.W. Jaromczyk, B.A. Roe, D.M. O'Sullivan, B. Scott, P. Tudzynski, Z. An, E.G. Arnaoudova, C.T. Bullock, N.D. Charlton, L. Chen, M. Cox, R.D. Dinkins, S. Florea, A.E. Glenn, A. Gordon, U. Güldener, D.R. Harris, W. Hollin, J. Jaromczyk, R.D. Johnson, A.K. Khan, E. Leistner, A. Leuchtmann, C. Li, J. Liu, J. Liu, M. Liu, W. Mace, C. Machado, P. Nagabhyru, J. Pan, J. Schmid, K. Sugawara, U. Steiner, J.E. Takach, E. Tanaka, J.S. Webb, E.V. Wilson, J.L. Wiseman, R. Yoshida, and Z. Zeng Plant-symbiotic fungi as chemical engineers: multi-genome analysis of the Clavicipitaceae reveals dynamics of alkaloid loci PLoS Genet. 9 2013 e1003323
26. M.J. Spiering, C.D. Moon, H.H. Wilkinson, and C.L. Schardl Gene clusters for insecticidal loline alkaloids in the grass-endophytic fungus Neotyphodium uncinatum Genetics 169 2005 1403 1414 (Pubitemid 40547452)
27. M.J. Spiering, J.R. Faulkner, D.X. Zhang, C. Machado, R.B. Grossman, and C.L. Schardl Role of the LolP cytochrome P450 monooxygenase in loline alkaloid biosynthesis Fungal Genet. Biol. 45 2008 1307 1314
28. H.F. Tsai, M.R. Siegel, and C.L. Schardl Transformation of Acremonium coenophialum, a protective fungal symbiont of the grass Festuca arundinacea Curr. Genet. 22 1992 399 406
29. H.H. Wilkinson, M.R. Siegel, J.D. Blankenship, A.C. Mallory, L.P. Bush, and C.L. Schardl Contribution of fungal loline alkaloids to protection from aphids in a grass-endophyte mutualism Mol. Plant Microbe Interact. 13 2000 1027 1033
30. S.G. Yates, J.C. Fenster, and R.J. Bartelt Assay of tall fescue seed extracts, fractions, and alkaloids using the large milkweed bug J. Agric. Food Chem. 37 1989 354 357
31. Z. Zhang, J. Ren, D.K. Stammers, J.E. Baldwin, K. Harlos, and C.J. Schofield Structural origins of the selectivity of the trifunctional oxygenase clavaminic acid synthase Nat. Struct. Biol. 7 2000 127 133 (Pubitemid 30082510)
32. D.X. Zhang, A.J. Stromberg, M.J. Spiering, and C.L. Schardl Coregulated expression of loline alkaloid-biosynthesis genes in Neotyphodium uncinatum cultures Fungal Genet. Biol. 46 2009 517 530