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Loline Alkaloid Gene Clusters of the Fungal Endophyte Neotyphodium Uncinatum Christopher L

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Loline Alkaloid Gene Clusters of the Fungal Endophyte Neotyphodium Uncinatum Christopher L University of Kentucky UKnowledge Plant Pathology Faculty Patents Plant Pathology 2-27-2007 Loline Alkaloid Gene Clusters of the Fungal Endophyte Neotyphodium Uncinatum Christopher L. Schardl University of Kentucky, [email protected] Heather H. Wilkinson University of Kentucky Martin J. Spiering University of Kentucky Right click to open a feedback form in a new tab to let us know how this document benefits oy u. Follow this and additional works at: https://uknowledge.uky.edu/plantpath_patents Part of the Plant Pathology Commons Recommended Citation Schardl, Christopher L.; Wilkinson, Heather H.; and Spiering, Martin J., "Loline Alkaloid Gene Clusters of the Fungal Endophyte Neotyphodium Uncinatum" (2007). Plant Pathology Faculty Patents. 5. https://uknowledge.uky.edu/plantpath_patents/5 This Patent is brought to you for free and open access by the Plant Pathology at UKnowledge. It has been accepted for inclusion in Plant Pathology Faculty Patents by an authorized administrator of UKnowledge. For more information, please contact [email protected]. US007183098B2 (12) United States Patent (10) Patent N0.: US 7,183,098 B2 Schardl et a1. (45) Date of Patent: Feb. 27, 2007 (54) LOLINE ALKALOID GENE CLUSTERS OF M.R. Siegel et al., “Fungal Endophyte-Infected Grasses: Alkaloid THE FUNGAL ENDOPHYTE Accumulation and Aphid Response”, Journal of Chemical Ecology, NEOTYPHODIUM UNCINATUM vol. 16, No. 12, 1990, pp. 3301-3315. C.O. Miles et al., “High Levels of Ergonovine and Lysergic Acid (75) Inventors: Christopher L. Schardl, Lexington, Amide in Toxic Achnatherum inebrians infection by an KY (US); Heather H. Wilkinson, Acremonium-like Endophytic Fungus”, J. Agric Food Chem., 1996, College Station, TX (US); Martin J. 44, pp. 1285-1290. M.R. Tepaske et al., “Analyses of Selected Endophyte-Infected Spiering, Lexington, KY (US) Grasses for the Presence of Loline-Type and Ergot-Type Alkaloids”, J. Agric. Food Chem., 1993, 41, pp. 2299-2303. (73) Assignee: University of Kentucky Research K.D. Craven et al., “Hybrid fungal endophytes symbiotic with the Foundation, Lexington, KY (US) grass Lo/ium pratense”, Sydowia, 53(1), pp. 44-73. M.J. Christensen et al., Taxonomy of Acremonium endophytes of ( * ) Notice: Subject to any disclaimer, the term of this tall fescue (Festuca arundinacea), meadow fescue (E pratensis) patent is extended or adjusted under 35 and perennial rye-grass (Lolium perenne), Mycol. Res., 97, (9), U.S.C. 154(b) by 475 days. (1993), pp. 1053-1092. A. Leuchtmann et al., “Mating compatibility and phylogenetic (21) Appl. No.: 10/601,700 relationships among two new species of Epich/oe and other con generic European species”, Mycol. Res. 12, (10), (1998), pp. (22) Filed: Jun. 24, 2003 1169-1182. M.J. Spiering et al., “Expressed sequence tags and genes associated (65) Prior Publication Data with loline alkaloid expression by the fungal endophyte Neotyphodium uncinatum”, Fungal Genetics and Biology, (2000), US 2004/0139496 A1 Jul. 15, 2004 pp. 1-13. Z Lin et al.,“Rapid Mini-Scale Plasmid Isolation for DNA Sequenc Related US. Application Data ing and Restriction Mapping”, BioTechniques, vol. 29, Sep. 2000, (60) Provisional application No. 60/390,446, ?led on Jun. pp. 466-468. 24, 2002. T.H. Al-Samarrai et al., “A simple method for extraction of fungal genomic DNA”, Letters in Applied Microbiology, 2000, vol. 30, pp. (51) Int. Cl. 53-56. C12P 17/14 (2006.01) S.F. Altschul et al., “Gapped BLAST and PSI-BLAST: a new generation of protein database search programs”, Nucleic Acids C07H 21/04 (2006.01) Research, 1997, vol. 25, No. 17, pp. 3389-3402. A63B 69/36 (2006.01) J .D. Blankenship et al., “Production of loline alkaloids by the grass (52) US. Cl. .............. .. 435/252.3; 435/120; 435/320.1; endophyte, Neotyphodium uncinatum, in de?ned media”, Photo 435/252.33; 435/252.8; 435/254.11; 536/232 chemistry, Vvol. 58, (2001), pp. 395-401. (58) Field of Classi?cation Search ........... .. 435/252.2, 435/252.3, 252.8, 254.11, 252.33, 320.1; (Continued) 536/232 Primary ExamineriRebecca E. Prouty See application ?le for complete search history. Assistant ExamineriKagnew Gebreyesus (56) References Cited (74) Attorney, Agent, or F irmiMcDermott Will & Emery LLP OTHER PUBLICATIONS (57) ABSTRACT M. Arévalo-Rodriguez et al., “Mutations that Cause Threonine Sensitivity Identify Catalytic and Regulatory Regions of the Aspartate Kinase of Saccharomyces cerevisiae”, Yeast 15, (1999), Loline alkaloids (LA), which are l-aminopyrrolizidines with pp. 1331-1345. an oxygen bridge, are produced by Epichloe" L.P. Bush et al., “Chemistry, occurrence and biological effects of (anamOrphINeOtyphOdium) species, endophytes of grasses. saturated pyrroliZidine alkaloids associated with endophyte-grass LA are insecticidal, thus helping protect host plants from interations”, Agriculture, Ecosystems and Environment, 44, (1993), pp. 81-102. insect herbivory. Suppression subtractive hybridization PCR N.P. Keller, “Review: Metabolic Pathway Gene Clusters in Fila was used to isolate transcripts up-regulated during loline mentous Fungi”, Fungal Genetics and Biology, 21, (1997), pp. alkaloid production in cultures of Neotyphodium uncinatum. 17-29. Subtracted cDNAs were cloned, and a k-phage cDNA J .A. Seo, et al., Characterization of Four Clustered and Coregulated library from an LA-expressing N. uncinatum culture was Genes Associated with Fumonisin Biosynthesis in Fusarium screened with subtracted cDNA. In BLAST searches, sev verticillioides, Fungal Genetics and Biology, 34, (2001) pp. 155 eral cDNAs identi?ed had sequence similarities to aspartate 165. kinases, and another with O-acetylhomoserine-(thiol)lyase. P. TudZynski et al., “Evidence for an ergot alkaloid gene cluster in Di?ferential expression of these two genes in LA-producing Claviceps purpurea”, Mol. Gen. Genet, (1999), 261, pp. 133-141. cultures of N. uncinatum was con?rmed, and in a survey of A. Leuchtrnann et al., “Different Levels of Protective Alkaloids in 23 isolates from 21 Neotyphodium and Epichloé species Grasses with Stroma-Forming and Seed-Transmitted Epichloé/ these two genes strictly correlated with LA production. Two Neotyphodium Endophytes”, Journal of Chemical Ecology, vol. 26, nucleic acid molecules encoding two loline alkaloid gene No.4, 2000, pp. 1025-1036. clusters have been identi?ed. H.H. Wilkinson et al., “Contribution of Fungal Loline Alkaloids to Protection from Aphids in a Grass-Endophyte Mutualism”, MPMI, vol. 13, No. 10, 2000, pp. 1027-1033. 7 Claims, 6 Drawing Sheets US 7,183,098 B2 Page 2 OTHER PUBLICATIONS G. Nicolas et al., “Lack of hepcidin gene expression and severe tissue iron overload in upstream stimulatory factor 2 (USFZ) M.L. Bogush et al. “Identi?cation and localization of difference knockout mice”, PNAS, vol. 98, No. 15, Jul. 17, 2001, pp. 8780 between Escherichia coli and Salmonella lyphimurium genomes by 8785. suppressive subtractive hybridization”, Molecular and General J. Oscarrsson et al., “Pulsatile growth hormone secretion decreases Genetics, (1999), vol. 262, pp. 721-729. S-adenosylmethionine synthetase in rat liver” Am. J. Physiol. L.P. Bush et al., “Bioprotective Alkalids of Grass-Fungal Endophyte Endocrinol Metab., vol. 280, pp. E280-E286, 2001. Symbiosesl”, Plant Physiol., (1997), vol. 114, pp. 1-7. A. Paszewski et al, “Sulphur Metabolism”, Aspergillus: 50 years on, AD. Byrd et al., “The [5-tubulin gene of Epichloé typhina from vol. 29, pp. 299-319. perennial ryegrass (Lolium perenne) ”, Current Genetics, (1990), R.H. Proctor et al., “Tri6 Encodes an Unusual Zinc Finger Protein vol. 18, pp. 347-354. Involved in Regulation of Trichothecene Biosyntheses in Fusarium L. Diatchenko et al., “Suppression subtractive hybridization: A sporotrichioides”, Applied and Environmental Microbiology, vol. method for generating differentially regulated or tissue-speci?c 61, No. 5, May 1995, pp. 1923-1930. cDNA probes and libraries”, Proceedings of the National Academy D.V. Rebrikov et al., “Mirror orientation selection (MOS): a method of Sciences of the United States ofAmerica, Jun. 11, 1996, vol. 93, for eliminating false positive clones form libraries generated by No. 12, pp. 6025-6030. suppression subtractive hybridization”, Nucleic Acids Research, L. Diatchenko et al., “Suppression Subtractive Hybridization: A 2000, vol. 28, No. 20, e90, pp. 1-4. Versatile Method for Identifying Differentially Expressed Genes”, C.L. Schardl et al., “Review: Epichloé festucae and Related cDNA Preparation and Characterization, Methods in Enzyrnology, Mutualistic Symbionts of Grasses”, Fungal Genetics and Biology, vol. 303, pp. 349-380. vol. 33, pp. 69-82, (2001). Y. Wang et al., “A Rapid CTAB DNA Isolation Technique for RAPD M. Sienko et al., “Structure and reguation of cysD, the Fingerprinting and Other PCR Applications”, BioFeedback, vol. 14, homocysteine synthase gene of Aspergillus nidulans”, Current No. 5, (1993). Genetics, (1998), vol. 33, pp. 136-144. W.O. Endege et al., “Representative cDNA Libraries and Their B. Tofern et al., Occurrence of loline alkaloids in Argyreia mollis Utility in Gene Expression Pro?ling”, BioTechniques, vol. 26, No. (Convolvulaceae), Phytochemistry, vol. 51, (1999), pp. 1177-1180. 2, (Mar. 1999), pp. 542-550. T. Yasuta et al., “DNA Sequence and Mutational Analysis of F.S. Gimble et al., MiniReview, “Invasion of a multitude of genetic Rhizobitoxine Biosysnthesis Genes in Bradyrhizobium elkanii” niches by mobile endonuclease genes”, FEMS Microbiology Let Applied and Environmental Microbiology, vol. 67, No. 11, Nov. ters, vol. 185, (2000), pp. 99-107. 2001, pp. 4999-5009. P. Liang et al., “Differential Display of Eukaryotic Messenger RNA B. Zhumabayeva et al., “Use of SMARTTM- Generated cDNA for by Means of the Polymerase Chain Reaction”, Science, vol. 257, Gene Expression Studies in Multiple Human Tumors”, Aug. 14, 1992, pp. 987-971. BioTechniques, vol. 30, No. 1, Jan. 2001, pp. 158-163. Patent Feb. 27, 2007 Sheet 1 0f 6 US 7,183,098 B2 /H H N\ H’ O H N R H, Loline CH3 H Norloline H H N-Methylloline CH3 CH3 N-Forrnylloline CH3 CH0 N-Formylnorloline H CH0 N-Acetylloline CH3 COCH3 N-Acetylnorloline H COCH3 Figure 1 U.S. Patent Feb.
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