Synthesis and characterization of synthetic analogs of cinnacidin, a novel phytotoxin from <i>Nectria</i> sp.

Irvine, Nicholas M.; Yerkes, Carla N.; Graupner, Paul R.; Roberts, Roben E; Hahn, Don R; Pearce, Cedric J.; Gerwick, Ben C.

doi:10.1002/ps.1579

Cited by 30 publications

(31 citation statements)

References 11 publications

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“…For the 1H/1H COSY, 256 experiments consisting of 1 K data points were collected with 96 transients collected per experiment. 13 C data were acquired using a 2D inverse-detected HMQC experiment. For this data set, 256 experiments were acquired over 2 K data points, with 160 transients per experiment.…”

Section: Nmr Sectroscopymentioning

confidence: 99%

“…13 Whole plant activity was assessed on the following species using one or both of the above means of application: Gossypium hirsutum (GOSHI), Brassica napus (BRSNN), Glycine max (GLXMA), Beta vulgaris (BEAVA), Stellaria media (STEME), Xanthium strumarium (XANST), Chenopodium album (CHEAL), Ipomoea hederacea (IPOHE), Amaranthum retroflexus (AMARE), Abutilon theophrasti (ABUTH), Viola arvensis (VIOAR), Polygonum convolvulus (POLCO), Zea mays (ZEAMX), Orysa sativa (ORYSA), Triticum aestivum (TRZAX), Alopecurus myosuroides (ALOMY), E. crus-galli (ECHCG), Digitaria sanguinalis (DIGSA), Sorghum vulgare (SORVU), Avena fatua (AVEFA), Cyperus esculentus (CYPES) and H. annuus (HELAN). Plants were seeded in sandy loam soil (preemergence testing) or a commercial potting mix containing 30% organic matter (post-emergence testing).…”

Section: Biological Activitymentioning

confidence: 99%

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Albucidin: a novel bleaching herbicide from Streptomyces albus subsp. chlorinus NRRL B-24108

et al. 2009

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A novel nucleoside phytotoxin, albucidin (1), was isolated from the culture broth of Streptomyces albus subsp. chlorinus NRRL B-24108 using bioassay directed fractionation. The structure of the new natural product, albucidin, was determined by NMR and MS; however, the compound has been reported earlier in the literature following synthetic modification of oxetanocin. This is the first report of herbicidal activity for compounds of this structural type. Albucidin shows high levels of broad spectrum activity following post-emergence applications as well as moderate levels of pre-emergence activity. Accordingly, albucidin could be an important new lead for herbicide discovery.

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Section: Nmr Sectroscopymentioning

confidence: 99%

Section: Biological Activitymentioning

confidence: 99%

Albucidin: a novel bleaching herbicide from Streptomyces albus subsp. chlorinus NRRL B-24108

et al. 2009

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“…These include several analogues of AAL toxin and fumonisin [67,68,69,70] (Figure 8). AAL toxins are produced by Alternaria alternata tomato pathovars and fumonisins are produced by Fusarium spp.…”

Section: Lipid Metabolismmentioning

confidence: 99%

Modes of Action of Microbially-Produced Phytotoxins

Duke

Dayan

2011

Toxins

108

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Some of the most potent phytotoxins are synthesized by microbes. A few of these share molecular target sites with some synthetic herbicides, but many microbial toxins have unique target sites with potential for exploitation by the herbicide industry. Compounds from both non-pathogenic and pathogenic microbes are discussed. Microbial phytotoxins with modes of action the same as those of commercial herbicides and those with novel modes of action of action are covered. Examples of the compounds discussed are tentoxin, AAL-toxin, auscaulitoxin aglycone, hydantocidin, thaxtomin, and tabtoxin.

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“…Foliar application of cinnacidin causes stunting and chlorosis. Both coronatine and cinnacidin act by mimicking the role of jasmonic acid (Irvine et al, 2008).…”

Section: Jasmonate Mimicsmentioning

confidence: 99%