@article{mitchell_alejos-gonzalez_gracz_danehower_daub_chilton_2003, title={Xanosporic acid, an intermediate in bacterial degradation of the fungal phototoxin cercosporin}, volume={62}, ISSN={["0031-9422"]}, DOI={10.1016/S0031-9422(02)00517-4}, abstractNote={The red fungal perylenequinone phototoxin cercosporin is oxidized by Xanthomonas campestris pv zinniae to a non-toxic, unstable green metabolite xanosporic acid, identified via its lactone as 1,12-bis(2′R-hydroxypropyl)-4,9-dihydroxy-6,7-methylenedioxy-11-methoxy-3-oxaperylen-10H-10-one-2-carboxylic acid. Xanosporolactone was isolated in approximately 2:1 ratio of M:P atropisomers.}, number={5}, journal={PHYTOCHEMISTRY}, author={Mitchell, TK and Alejos-Gonzalez, F and Gracz, HS and Danehower, DA and Daub, ME and Chilton, WS}, year={2003}, month={Mar}, pages={723–732} } @article{mitchell_chilton_daub_2002, title={Biodegradation of the polyketide toxin cercosporin}, volume={68}, ISSN={["0099-2240"]}, DOI={10.1128/AEM.68.9.4173-4181.2002}, abstractNote={ABSTRACTCercosporin is a non-host-specific polyketide toxin produced by many species of plant pathogens belonging to the genusCercospora. This red-pigmented, light-activated toxin is an important pathogenicity determinant forCercosporaspecies. In this study, we screened 244 bacterial isolates representing 12 different genera for the ability to degrade cercosporin. Cercosporin degradation was determined by screening for the presence of cleared zones surrounding colonies on cercosporin-containing culture medium and was confirmed by assaying the kinetics of degradation in liquid medium. Bacteria belonging to four different genera exhibited the cercosporin-degrading phenotype. The isolates with the greatest cercosporin-degrading activity belonged toXanthomonas campestrispv. zinniae andX. campestrispv. pruni. Isolates of these pathovars removed over 90% of the cercosporin from culture medium within 48 h. Bacterial degradation of red cercosporin was accompanied by a shift in the color of the growth medium to brown and then green. The disappearance of cercosporin was accompanied by the appearance of a transient green product, designated xanosporic acid. Xanosporic acid and its more stable lactone derivative, xanosporolactone, are nontoxic to cercosporin-sensitive fungi and to plant tissue and are labile in the presence of light. Detailed spectroscopic analysis (to be reported in a separate publication) of xanosporolactone revealed that cercosporin loses one methoxyl group and gains one oxygen atom in the bacterial conversion. The resulting chromophore (4,9-dihydroxy-3-oxaperlylen-10H-10-one) has never been reported before but is biosynthetically plausible via oxygen insertion by a cytochrome P-450 enzyme.}, number={9}, journal={APPLIED AND ENVIRONMENTAL MICROBIOLOGY}, author={Mitchell, TK and Chilton, WS and Daub, ME}, year={2002}, month={Sep}, pages={4173–4181} } @article{drehmel_chilton_2002, title={Characterization and toxicity of Amanita cokeri extract}, volume={28}, ISSN={["0098-0331"]}, DOI={10.1023/A:1017986108720}, abstractNote={The nonprotein amino acids 2-amino-3-cyclopropylbutanoic acid and 2-amino-5-chloro-4-pentenoic acid were isolated from the mushroom Amanita cokeri. The cyclopropyl amino acid is toxic to the fungus Cercospora kikuchii, the arthropod Oncopeltus fasciatus (milk weed bug), and the bacteria Agrobacterium tumefaciens, Erwinia amylovora, and Xanthomonas campestris. Toxicity to bacteria was reversible by addition of isoleucine to the medium. No toxicity was observed for 2-amino-5-chloro-4-pentenoic acid.}, number={2}, journal={JOURNAL OF CHEMICAL ECOLOGY}, author={Drehmel, DC and Chilton, WS}, year={2002}, month={Feb}, pages={333–341} } @article{hwang_chilton_benson_2002, title={Pyrrolnitrin production by Burkholderia cepacia and biocontrol of Rhizoctonia stem rot of poinsettia}, volume={25}, ISSN={["1049-9644"]}, DOI={10.1016/S1049-9644(02)00044-0}, abstractNote={Pyrrolnitrin production by Burkholderia cepacia strain 5.5B was closely related to suppression of stem rot of poinsettia caused by Rhizoctonia solani. Selected strains RR 13-1 and UV 19-4, which produced significantly less pyrrolnitrin than the parent strain 5.5B, lost the ability to control stem rot completely. Selected strain RR 21-2 produced the same level of pyrrolnitrin as strain 5.5B and was as effective as strain 5.5B in stem rot control. The effect of medium type and initial pH of medium on pyrrolnitrin production by B. cepacia was investigated to improve efficacy of biocontrol. More pyrrolnitrin was accumulated when the initial pH was adjusted to 5.8 than 6.8. With an initial pH of 5.8, strains of B. cepacia produced more pyrrolnitrin in a nutrient broth medium than in a minimum salts medium. Pyrrolnitrin was the major factor in biocontrol of Rhizoctonia stem rot of poinsettia by B. cepacia. Improvement in biocontrol efficacy may be possible by adjusting culture conditions to optimize pyrrolnitrin production.}, number={1}, journal={BIOLOGICAL CONTROL}, author={Hwang, J and Chilton, WS and Benson, DM}, year={2002}, month={Sep}, pages={56–63} } @article{chilton_drehmel_2001, title={Cyclopropyl amino acids of Amanita}, volume={29}, number={8}, journal={Biochemical Systematics and Ecology}, author={Chilton, W. S. and Drehmel, D. C.}, year={2001}, pages={853–855} } @article{chilton_petit_chilton_dessaux_2001, title={Structure and characterization of the crown gall opines heliopine, vitopine and rideopine}, volume={58}, ISSN={["0031-9422"]}, DOI={10.1016/S0031-9422(01)00166-2}, abstractNote={The crown gall opines heliopine from tumors induced by octopine type Agrobacterium tumefaciens strains A6, A136(pTiB6-806), E9, A652 and 1590-1 and vitopine from tumor induced by grapevine strains S4 and T2 are identical to synthetic N 2-(1′R-carboxyethyl)-l-glutamine. Tumors produced by strains S4 and T2 do not contain octopine or lysopine, but they do contain heliopine and the new opine ridéopine identified as N-(4′-aminobutyl)-d-glutamic acid. Grapevine strains S4 and T2 grow normally on tumor heliopine or synthetic heliopine and on tumor and synthetic ridéopine as well as on ridéopine lactam as sole carbon source. While octopine strains A6 and A136(pTiB6-806) do not grow on heliopine, mutant colonies do appear after a few weeks. Heliopine catabolism by octopine strains is not induced by octopine.}, number={1}, journal={PHYTOCHEMISTRY}, author={Chilton, WS and Petit, A and Chilton, MD and Dessaux, Y}, year={2001}, month={Sep}, pages={137–142} } @article{gamboa-leon_chilton_2000, title={Isobutylamide numbing agents of toothache grass, Ctenium aromaticum}, volume={28}, ISSN={["1873-2925"]}, DOI={10.1016/S0305-1978(00)00011-9}, abstractNote={Fourteen compounds were isolated from the 95% ethanol reflux extract of Asarum sieboldii Miq. var. Seoulense Nakai, including five phenanthrene derivatives (1–5), three isobutyl amides (6–8), three phenylpropanoids (9–11) and three lignins (12–14). The structures of these compounds were identified by spectroscopic methods and by comparison with the reported spectroscopic data. Among them, compounds 6 and 11 were firstly reported from the family Aristolochiaceae, and compounds 3 and 4 were reported for the first time from the genus Asarum. Additionally, compounds 1, 2 and 8 were isolated from A. sieboldii Miq. var. Seoulense Nakai for the first time. These compounds have shown chemical relationships between A. sieboldii Miq. var. Seoulense Nakai and other species of Asarum as well as those found in the genus Aristolochia in the family Aristolochiaceae.}, number={10}, journal={BIOCHEMICAL SYSTEMATICS AND ECOLOGY}, author={Gamboa-Leon, R and Chilton, WS}, year={2000}, month={Dec}, pages={1019–1021} } @article{vaudequin-dransart_petit_chilton_dessaux_1998, title={The cryptic plasmid of Agrobacterium tumefaciens cointegrates with the Ti plasmid and cooperates for opine degradation}, volume={11}, ISSN={["1943-7706"]}, DOI={10.1094/MPMI.1998.11.7.583}, abstractNote={ We crossed the Agrobacterium tumefaciens chrysanthemum strain ANT4, which harbors four plasmids, with the plasmid-free recipient C58.00RS. Transconjugants degrading the Amadori-opines chrysopine and deoxy-fructo-syl-oxo-proline (dfop) harbored the Ti plasmid of ANT4, termed pAtANT4b. Upon transfer to the recipient strain C58.00RS, pAtANT4b (pTiANT4) and pANT4a (the largest of the four plasmids of ANT4) could cointegrate. The cointegration of the two plasmids occurs at various places of the pTiANT4, a feature that may affect several functions of the Ti plasmid (e.g., opine degradation). Transcon-jugants utilizing the opine deoxy-fructosyl-glutamine (dfg) always harbored the large pAtANT4a. Other Agrobacterium strains, including nonpathogenic strains such as C58C1, naturally degraded dfg. Remarkably, strain C58C1 carries a large cryptic plasmid termed pAtC58 that also encodes dfg degradation. A screening of physiological traits additionally revealed that this plasmid allows utilization of octopine as sole nitrogen source after mutation. All these results demonstrate that the larger plasmid of A. tumefaciens is a catabolic plasmid and that both the “cryptic” plasmid and Ti plasmid cooperate for opine degradation. }, number={7}, journal={MOLECULAR PLANT-MICROBE INTERACTIONS}, author={Vaudequin-Dransart, V and Petit, A and Chilton, WS and Dessaux, Y}, year={1998}, month={Jul}, pages={583–591} } @article{melanson_chilton_mastersmoore_chilton_1997, title={A deletion in an indole synthase gene is responsible for the DIMBOA-deficient phenotype of bxbx maize}, volume={94}, ISSN={["0027-8424"]}, DOI={10.1073/pnas.94.24.13345}, abstractNote={The biosynthesis of DIMBOA, a pesticidal secondary metabolite of maize, branches off the tryptophan pathway. We have previously demonstrated that indole is the last intermediate common to both the tryptophan and hydroxamic acid pathways. The earliest discovered mutant in the DIMBOA pathway,bxbx(benzoxazineless), is deficient in the production of DIMBOA and related compounds. This paper presents evidence that a gene identified by Kramer and Koziel [Kramer, V. C. & Koziel, M. G. (1995)Plant Mol. Biol.27, 1183–1188] as maize tryptophan synthase α (TSA) is the site of the genetic lesion in the DIMBOA-deficient mutant maize linebxbx. We demonstrate that theTSAgene has sustained a 924-bp deletion inbxbxcompared with its counterpart in wild-type maize. We report that theTSAgene maps to the same location as thebxbxmutation, on the short arm of chromosome 4. We present evidence that the very early and very high level of expression ofTSAcorresponds to the timing and level of DIMBOA biosynthesis but is strikingly different from the expression of the maize tryptophan synthase β (TSB) genes. We show that feeding indole tobxbxseedlings restores their ability to synthesize DIMBOA. We conclude that the maize enzyme initially named tryptophan synthase α in fact is a DIMBOA biosynthetic enzyme, and we propose that it be renamed indole synthase. This work confirms and enlarges upon the findings of Freyet al.[Frey, M. Chomet, P., Glawischniq, E., Stettner, C., Grün, S., Winklmair, A., Eisenreich, W., Bacher, A., Meeley, R. B., Briggs, S. P., Simcox, K. & Gierl, A. (1997)Science277, 696–699], which appeared while the present paper was in review.}, number={24}, journal={PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA}, author={Melanson, D and Chilton, MD and MastersMoore, D and Chilton, WS}, year={1997}, month={Nov}, pages={13345–13350} } @article{loubens_chilton_dion_1997, title={Detection of activity responsible for induction of the Agrobacterium tumefaciens virulence genes in bacteriological agar}, volume={63}, number={11}, journal={Applied and Environmental Microbiology}, author={Loubens, I. and Chilton, W. S. and Dion, P.}, year={1997}, pages={4578–4580} } @article{moore_chilton_canfield_1997, title={Diversity of opines and opine-catabolizing bacteria isolated from naturally occurring crown gall tumors}, volume={63}, number={1}, journal={Applied and Environmental Microbiology}, author={Moore, L. W. and Chilton, W. S. and Canfield, M. L.}, year={1997}, pages={201–207} } @article{chilton_1996, title={The potential for manipulating inherent chemical defenses in plants: DIMBOA in maize}, volume={24}, number={3}, journal={Revista Latinoamericana de Qui?mica}, author={Chilton, W. S.}, year={1996}, pages={223} } @article{chilton_stomp_beringue_bouzar_vaudequindransart_petit_dessaux_1995, title={THE CHRYSOPINE FAMILY OF AMADORI-TYPE CROWN GALL OPINES}, volume={40}, ISSN={["0031-9422"]}, DOI={10.1016/0031-9422(93)00283-L}, abstractNote={Crown gall tumours induced by four groups of Agrobacterium tumefaciens isolates, derived from galls from four different locations in North and South America and Europe, were found to contain mannityl opine-related metabolites derived from condensation of glucose with glutamine followed by Amadori rearrangement. The opines were characterized spectroscopically as N-(1′-deoxy-d-fructos-1′-yl)-5-oxo-l-proline, Nα-(1′-deoxy-d-fructos-1′-yl)-l-glutamine and its spiropyranosyl lactone, chrysopine. Tumours induced by A. tumefaciens strain 2788 and by Ficus strains also contained nopaline, while those induced by A. tumefaciens K224, K289 and Chry9 contained l, and an unidentified opine, pseudo-nopaline.}, number={3}, journal={PHYTOCHEMISTRY}, author={CHILTON, WS and STOMP, AM and BERINGUE, V and BOUZAR, H and VAUDEQUINDRANSART, V and PETIT, A and DESSAUX, Y}, year={1995}, month={Oct}, pages={619–628} }