Stephen O Duke

United States Department of Agriculture, Fort Collins, CO, USA

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Publications (99)180.18 Total impact

  • Source
    Article: Aminomethylphosphonic acid accumulation in plant species treated with glyphosate.
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    ABSTRACT: Aminomethylphosphonic acid (AMPA) is the most frequently detected metabolite of glyphosate in plants. The objective of this study was to determine if there is any correlation of metabolism of glyphosate to AMPA in different plant species and their natural level of resistance to glyphosate. Greenhouse studies were conducted to determine the glyphosate I 50 values (rate required to cause a 50% reduction in plant growth) and to quantify AMPA and shikimate concentrations in selected leguminous and nonleguminous species treated with glyphosate at respective I 50 rates. Coffee senna [ Cassia occidentalis (L.) Link] was the most sensitive ( I 50 = 75 g/ha) and hemp sesbania [ Sesbania herbacea (P.Mill.) McVaugh] was the most resistant ( I 50 = 456 g/ha) to glyphosate. Hemp sesbania was 6-fold and Illinois bundleflower [ Desmanthus illinoensis (Michx.) MacM. ex B.L.Robins. & Fern.] was 4-fold more resistant to glyphosate than coffee senna. Glyphosate was present in all plant species, and its concentration ranged from 0.308 to 38.7 microg/g of tissue. AMPA was present in all leguminous species studied except hemp sesbania. AMPA concentration ranged from 0.119 to 4.77 microg/g of tissue. Shikimate was present in all plant species treated with glyphosate, and levels ranged from 0.053 to 16.5 mg/g of tissue. Non-glyphosate-resistant (non-GR) soybean accumulated much higher shikimate than glyphosate-resistant (GR) soybean. Although some leguminous species were found to be more resistant to glyphosate than others, and there was considerable variation between species in the glyphosate to AMPA levels found, metabolism of glyphosate to AMPA did not appear to be a common factor in explaining natural resistance levels.
    Journal of Agricultural and Food Chemistry 03/2008; 56(6):2125-30. · 2.82 Impact Factor
  • Article: A functional genomics investigation of allelochemical biosynthesis in Sorghum bicolor root hairs.
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    ABSTRACT: Sorghum is considered to be one of the more allelopathic crop species, producing phytotoxins such as the potent benzoquinone sorgoleone (2-hydroxy-5-methoxy-3-[(Z,Z)-8',11',14'-pentadecatriene]-p-benzoquinone) and its analogs. Sorgoleone likely accounts for much of the allelopathy of Sorghum spp., typically representing the predominant constituent of Sorghum bicolor root exudates. Previous and ongoing studies suggest that the biosynthetic pathway for this plant growth inhibitor occurs in root hair cells, involving a polyketide synthase activity that utilizes an atypical 16:3 fatty acyl-CoA starter unit, resulting in the formation of a pentadecatrienyl resorcinol intermediate. Subsequent modifications of this resorcinolic intermediate are likely to be mediated by S-adenosylmethionine-dependent O-methyltransferases and dihydroxylation by cytochrome P450 monooxygenases, although the precise sequence of reactions has not been determined previously. Analyses performed by gas chromatography-mass spectrometry with sorghum root extracts identified a 3-methyl ether derivative of the likely pentadecatrienyl resorcinol intermediate, indicating that dihydroxylation of the resorcinol ring is preceded by O-methylation at the 3'-position by a novel 5-n-alk(en)ylresorcinol-utilizing O-methyltransferase activity. An expressed sequence tag data set consisting of 5,468 sequences selected at random from an S. bicolor root hair-specific cDNA library was generated to identify candidate sequences potentially encoding enzymes involved in the sorgoleone biosynthetic pathway. Quantitative real time reverse transcription-PCR and recombinant enzyme studies with putative O-methyltransferase sequences obtained from the expressed sequence tag data set have led to the identification of a novel O-methyltransferase highly and predominantly expressed in root hairs (designated SbOMT3), which preferentially utilizes alk(en)ylresorcinols among a panel of benzene-derivative substrates tested. SbOMT3 is therefore proposed to be involved in the biosynthesis of the allelochemical sorgoleone.
    Journal of Biological Chemistry 03/2008; 283(6):3231-47. · 4.77 Impact Factor
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    Article: Identification of molecular pathways affected by pterostilbene, a natural dimethylether analog of resveratrol.
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    ABSTRACT: Pterostilbene, a naturally occurring phenolic compound produced by agronomically important plant genera such as Vitis and Vacciunium, is a phytoalexin exhibiting potent antifungal activity. Additionally, recent studies have demonstrated several important pharmacological properties associated with pterostilbene. Despite this, a systematic study of the effects of pterostilbene on eukaryotic cells at the molecular level has not been previously reported. Thus, the aim of the present study was to identify the cellular pathways affected by pterostilbene by performing transcript profiling studies, employing the model yeast Saccharomyces cerevisiae. S. cerevisiae strain S288C was exposed to pterostilbene at the IC50 concentration (70 muM) for one generation (3 h). Transcript profiling experiments were performed on three biological replicate samples using the Affymetrix GeneChip Yeast Genome S98 Array. The data were analyzed using the statistical methods available in the GeneSifter microarray data analysis system. To validate the results, eleven differentially expressed genes were further examined by quantitative real-time RT-PCR, and S. cerevisiae mutant strains with deletions in these genes were analyzed for altered sensitivity to pterostilbene. Transcript profiling studies revealed that pterostilbene exposure significantly down-regulated the expression of genes involved in methionine metabolism, while the expression of genes involved in mitochondrial functions, drug detoxification, and transcription factor activity were significantly up-regulated. Additional analyses revealed that a large number of genes involved in lipid metabolism were also affected by pterostilbene treatment. Using transcript profiling, we have identified the cellular pathways targeted by pterostilbene, an analog of resveratrol. The observed response in lipid metabolism genes is consistent with its known hypolipidemic properties, and the induction of mitochondrial genes is consistent with its demonstrated role in apoptosis in human cancer cell lines. Furthermore, our data show that pterostilbene has a significant effect on methionine metabolism, a previously unreported effect for this compound.
    BMC Medical Genomics 02/2008; 1:7. · 3.69 Impact Factor
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    Article: Phytotoxic Eremophilanes from Ligularia macrophylla.
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    ABSTRACT: Systematic bioassay-guided fractionation of the methylene chloride extract of the roots from Ligularia macrophylla was performed to identify both phytotoxic and antifungal compounds. Four phytotoxic eremophilanes (furanoeremophilan-14beta,6alpha-olide, 6beta-angeloyloxy-10beta-hydroxyfuranoeremophilane, eremophil-7(11)-ene-12,8alpha;14beta,6alpha-diolide, and 3alpha-angeloyloxybakkenolide A) and two antifungal fatty acids (linoleic acid and alpha-linolenic acid) were isolated. The X-ray crystal structure determination of 6beta-angeloyloxy-10beta-hydroxyfuranoeremophilane is reported here for the first time. All four eremophilanes substantially inhibited growth of the monocot Agrostis stolonifera (bentgrass) while demonstrating little activity against the dicot Lactuca sativa (lettuce) at 1000 microM. In a dose-response screening of all compounds for growth inhibitory activity against Lemna paucicostata, 6beta-angeloyloxy-10beta-hydroxyfuranoeremophilane was the most active with an IC50 of 2.94+/-0.16 microM. This compound also caused the greatest reduction of photosynthetic electron flow; however, its mode of action remains to be determined. Evaluation of isolated compounds for activity against the Formosan subterranean termite, Coptotermes formosanus, is also reported. At a concentration of 0.5% (wt/wt), 6beta-angeloyloxy-10beta-hydroxyfuranoeremophilane significantly reduced the consumption of filter paper by C. formosanus.
    Journal of Agricultural and Food Chemistry 01/2008; 55(26):10656-63. · 2.82 Impact Factor
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    Article: Mini-review Glyphosate: a once-in-a-century herbicide
    Stephen O Duke, Stephen B Powles
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    ABSTRACT: Since its commercial introduction in 1974, glyphosate [N-(phosphonomethyl)glycine] has become the dominant herbicide worldwide. There are several reasons for its success. Glyphosate is a highly effective broad-spectrum herbicide, yet it is very toxicologically and environmentally safe. Glyphosate translocates well, and its action is slow enough to take advantage of this. Glyphosate is the only herbicide that targets 5-enolpyruvyl-shikimate-3-phosphate synthase (EPSPS), so there are no competing herbicide analogs or classes. Since glyphosate became a generic compound, its cost has dropped dramatically. Perhaps the most important aspect of the success of glyphosate has been the introduction of transgenic, glyphosate-resistant crops in 1996. Almost 90% of all transgenic crops grown worldwide are glyphosate resistant, and the adoption of these crops is increasing at a steady pace. Glyphosate/glyphosate-resistant crop weed management offers significant environmental and other benefits over the technologies that it replaces. The use of this virtually ideal herbicide is now being threatened by the evolution of glyphosate-resistant weeds. Adoption of resistance management practices will be required to maintain the benefits of glyphosate technologies for future generations.  2008 Society of Chemical Industry 1 INTRODUCTION The era of weed management with synthetic herbicides began in earnest after World War II with the introduction of 2,4-D. So the title of this paper is perhaps presumptuous, considering we are only 60 years into this era. Nevertheless, the simple molecule glyphosate [N-(phosphonomethyl)glycine] is the most important herbicide of this period. This review will discuss why glyphosate more closely approximates to a perfect herbicide than any other, and considers how the advent of transgenic crops has catapulted glyphosate to the dominant herbicide of this time. The review concludes by discussing how the combination of glyphosate overreliance and the evolutionary potential of weed species threatens glyphosate's efficacy and sustainability as a precious herbicide resource for world agriculture. There are other, more encyclopaedic reviews and books on glyphosate 1 – 4 and glyphosate-resistant (GR) crops, 5 – 7 but there is none that approaches this topic from the viewpoint that is taken in this short review.
    Pest Management Science Pest Manag Sci. 01/2008; 64:319-325.
  • Chapter: Genomic Approaches to Understanding Allelochemical Effects on Plants
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    ABSTRACT: Little is known concerning the mode of action of allelochemicals or plant defense responses mounted against them. Theoretically, changes in the expression of genes encoding the primary target or other proteins in the same pathway should occur soon after phytotoxin exposure. Defense responses, such as the induction of genes involved in chemical detoxification, may occur later, depending on the nature of the chemosensors which presumably exist in plant cells. We first used yeast (Saccharomyces cerevisiae) to test the concept of transcriptome profiling of toxicant modes of action. Characteristic gene induction profiles related to specific molecular target sites were verified with several fungicides. A battery of xenobiotic defense-associated genes were found to be dramatically induced in Arabidopsis following exposure to an array of structurally unrelated xenobiotics, including a herbicide, an allelochemical, and herbicide safeners. These genes are unlikely to be strongly linked to the mode of action of a specific phytotoxin, but rather constitute a coordinately-controlled xenobiotic defense gene network. Transcriptional profiling experiments using microarrays are being conducted to examine the effects of various herbicides and natural phytotoxins on the Arabidopsis transcriptome.
    12/2007: pages 157-167;
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    Article: p-Hydroxyphenylpyruvate dioxygenase is a herbicidal target site for beta-triketones from Leptospermum scoparium.
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    ABSTRACT: p-Hydroxyphenylpyruvate dioxygenase (HPPD) is a key enzyme in tyrosine catabolism and is the molecular target site of beta-triketone pharmacophores used to treat hypertyrosinemia in humans. In plants, HPPD is involved in the biosynthesis of prenyl quinones and tocopherols, and is the target site of beta-triketone herbicides. The beta-triketone-rich essential oil of manuka (Leptospermum scoparium), and its components leptospermone, grandiflorone and flavesone were tested for their activity in whole-plant bioassays and for their potency against HPPD. The achlorophyllous phenotype of developing plants exposed to manuka oil or its purified beta-triketone components was similar to that of plants exposed to the synthetic HPPD inhibitor sulcotrione. The triketone-rich fraction and leptospermone were approximatively 10 times more active than that of the crude manuka oil, with I50 values of 1.45, 0.96 and 11.5 microg mL(-1), respectively. The effect of these samples on carotenoid levels was similar. Unlike their synthetic counterpart, steady-state O2 consumption experiments revealed that the natural triketones were competitive reversible inhibitors of HPPD. Dose-response curves against the enzyme activity of HPPD provided apparent I50 values 15.0, 4.02, 3.14, 0.22 microg mL(-1) for manuka oil, triketone-rich fraction, leptospermone and grandiflorone, respectively. Flavesone was not active. Structure-activity relationships indicate that the size and lipophilicity of the side-chain affected the potency of the compounds. Computational analysis of the catalytic domain of HPPD indicates that a lipophilic domain proximate from the Fe2+ favors the binding of ligands with lipophilic moieties.
    Phytochemistry 08/2007; 68(14):2004-14. · 3.35 Impact Factor
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    Article: Glyphosate-resistant and -susceptible soybean (Glycine max) and canola (Brassica napus) dose response and metabolism relationships with glyphosate.
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    ABSTRACT: Experiments were conducted to determine (1) dose response of glyphosate-resistant (GR) and -susceptible (non-GR) soybean [Glycine max (L.) Merr.] and canola (Brassica napus L.) to glyphosate, (2) if differential metabolism of glyphosate to aminomethyl phosphonic acid (AMPA) is the underlying mechanism for differential resistance to glyphosate among GR soybean varieties, and (3) the extent of metabolism of glyphosate to AMPA in GR canola and to correlate metabolism to injury from AMPA. GR50 (glyphosate dose required to cause a 50% reduction in plant dry weight) values for GR (Asgrow 4603RR) and non-GR (HBKC 5025) soybean were 22.8 kg ae ha-1 and 0.47 kg ha-1, respectively, with GR soybean exhibiting a 49-fold level of resistance to glyphosate as compared to non-GR soybean. Differential reduction in chlorophyll by glyphosate was observed between GR soybean varieties, but there were no differences in shoot fresh weight reduction. No significant differences were found between GR varieties in metabolism of glyphosate to AMPA, and in shikimate levels. These results indicate that GR soybean varieties were able to outgrow the initial injury from glyphosate, which was previously caused at least in part by AMPA. GR50 values for GR (Hyola 514RR) and non-GR (Hyola 440) canola were 14.1 and 0.30 kg ha-1, respectively, with GR canola exhibiting a 47-fold level of resistance to glyphosate when compared to non-GR canola. Glyphosate did not cause reduction in chlorophyll content and shoot fresh weight in GR canola, unlike GR soybean. Less glyphosate (per unit leaf weight) was recovered in glyphosate-treated GR canola as compared to glyphosate-treated GR soybean. External application of AMPA caused similar injury in both GR and non-GR canola. The presence of a bacterial glyphosate oxidoreductase gene in GR canola contributes to breakdown of glyphosate to AMPA. However, the AMPA from glyphosate breakdown could have been metabolized to nonphytotoxic metabolites before causing injury to GR canola. Injury in GR and non-GR canola from exogenous application of AMPA was similar.
    Journal of Agricultural and Food Chemistry 06/2007; 55(9):3540-5. · 2.82 Impact Factor
  • Chapter: BIOCONTROL OF WEEDS WITH ALLELOPATHY: CONVENTIONAL AND TRANSGENIC APPROACHES
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    ABSTRACT: Growing highly allelopathic crops has the potential to significantly reduce our reliance on synthetic herbicides for weed management. Specific phytotoxins have been found in allelopathic rice, wheat, and rye varieties, but this information has not been used in breeding varieties that can be marketed on the basis of their weed management properties. Although such a conventional approach is viable, transgenic strategies may be better. For example, genes encoding enzymes of the highly potent phytotoxin sorgoleone in Sorghum spp. might be transgenically manipulated to enhance the allelopathic properties of sorghum crops. This potent phytotoxin is exclusively synthesized and secreted by root hairs. The sorgoleone pathway has been elucidated and putative genes encoding them have been identified and partially verified.
    05/2007: pages 75-85;
  • Article: Functional characterization of desaturases involved in the formation of the terminal double bond of an unusual 16:3Delta(9,12,150) fatty acid isolated from Sorghum bicolor root hairs.
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    ABSTRACT: Sorgoleone, produced in root hair cells of sorghum (Sorghum bicolor), is likely responsible for much of the allelopathic properties of sorghum root exudates against broadleaf and grass weeds. Previous studies suggest that the biosynthetic pathway of this compound initiates with the synthesis of an unusual 16:3 fatty acid possessing a terminal double bond. The corresponding fatty acyl-CoA serves as a starter unit for polyketide synthases, resulting in the formation of 5-pentadecatrienyl resorcinol. This resorcinolic intermediate is then methylated by an S-adenosylmethionine-dependent O-methyltransferase and subsequently dihydroxylated, yielding the reduced (hydroquinone) form of sorgoleone. To characterize the corresponding enzymes responsible for the biosynthesis of the 16:3 fatty acyl-CoA precursor, we identified and cloned three putative fatty acid desaturases, designated SbDES1, SbDES2, and SbDES3, from an expressed sequence tag (EST) data base prepared from isolated root hairs. Quantitative real-time RT-PCR analyses revealed that these three genes were preferentially expressed in sorghum root hairs where the 16:2 and 16:3 fatty acids were exclusively localized. Heterologous expression of the cDNAs in Saccharomyces cerevisiae revealed that recombinant SbDES2 converted palmitoleic acid (16:1Delta(9)) to hexadecadienoic acid (16:2Delta(9,12)), and that recombinant SbDES3 was capable of converting hexadecadienoic acid into hexadecatrienoic acid (16:3Delta(9,12,15)). Unlike other desaturases reported to date, the double bond introduced by SbDES3 occurred between carbons 15 and 16 resulting in a terminal double bond aliphatic chain. Collectively, the present results strongly suggest that these fatty acid desaturases represent key enzymes involved in the biosynthesis of the allelochemical sorgoleone.
    Journal of Biological Chemistry 03/2007; 282(7):4326-35. · 4.77 Impact Factor
  • Article: Tentoxin effects on infrastructure and greening of ivyleaf morningglory (Ipomoea hederacea var. hederacea) cotyledons
    STEPHEN O. DUKE, REX N. PAUL, JAMES L. WICKLIFF
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    ABSTRACT: The effects of 20 μM tentoxin on mesophyll chloroplast ultra-structural development, chlorophyll organization and accumulation, and pigment transformations in cotyledons of dark-grown, 4-day-old ivyleaf morningglory [Ipomoea hederacea (L.) Jacq. var. hederacea]were monitored. After 6 h of white light (200 μEm−2T.s−1), many plastids of tentoxin-treated tissues contained prolamellar bodies or inconsistent internal membrane orientation in contrast to the uniform internal membrane orientation and absence of prolamellar bodies in controls. Grana stacking did not progress beyond three to four disc loculi in tentoxin-treatments, and fret membranes were usually discontinuous and reduced. Cylindrical or cupped grana appeared in many chloroplasts after 3 days of light, while other chloroplasts in which disruption was more pronounced had few grana except for remnants, but usually did possess vesicles or structures resembling prolamellar bodies. Tentoxin had no apparent effect on stroma density or plastoglobuli size and number. No starch grains appeared in any of the tentoxin treatments, whereas they appeared after 24 h in controls. Initial protochlorophyllide content and its photoconversion to chlorophyllide and subsequent Shibata shift were not affected by tentoxin. Chlorophyll accumulation rates in tentoxin-treated cotyledons were about 10% of control rates during the first 24 h of greening and about 20% of controls from 48 to 72 h of greening. Chlorophyll alb ratio and PSU size (total Chl/P700) were not significantly affected by tentoxin.
    Physiologia Plantarum 04/2006; 49(1):27 - 36. · 3.11 Impact Factor
  • Article: Tentoxin does not cause chlorosis in greening mung bean leaves by inhibiting photophosphorylation
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    ABSTRACT: Effects of the fungal toxin, tentotoxin, on development and chlorophyll accumulation of plastids of primary leaves of mung bean [Vigna radiata (L.) Wilczek cv. Berken] were studied using spectrophotometric, electrophoretic, and microscopic procedures. In etioplasts of control tissues both prolamellar bodies and prothylakoids occurred, whereas small vesicles were associated with structurally distinct prolamellar bodies in tentoxin-affected etioplasts. As determined by in vivo spectrophotometry, tentoxin-affected etioplasts had 25% less phototransformable protochlorophyll(ide) and 35% less non-phototransformable protochlorophyll(ide) than had control etioplasts after 5 days of dark seedling growth. Tentoxin had no effect on the rate of the Shibita shift. Protochlorophyll(ide) resynthesis in the dark immediately after protochlorophyll(ide) phototransformation was five to six times slower in tentoxintreated than in control tissues. Effects on chlorophyll(ide) content were observed within 30 min of the beginning of continuous white light exposure. In vivo measurement of cytochrome f redox activity revealed that this cytochrome was linked to light-driven electron flow in control tissues within 20 min of the beginning of continuous white light, whereas in the tentoxin-treated tissues there was no linkage (despite the presence of cytochromef) at any time. Coupling factor 1 was present and had potential ATPase activity in both control and tentoxin-affected plastids. There was about sixteen times more chlorophyll in control than in tentoxin-treated tissues in continuous as well as in intermittent (2 min light/118 min dark) light. These data are consistent with the view that tentoxin disrupts normal etioplast and chloroplast development through a mechanism unrelated to photophosphorylation.
    Physiologia Plantarum 04/2006; 56(4):387 - 398. · 3.11 Impact Factor
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    Article: Antifungal activity of thiophenes from Echinops ritro.
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    ABSTRACT: Extracts from 30 plants of the Greek flora were evaluated for their antifungal activity using direct bioautography assays with three Colletotrichum species. Among the bioactive extracts, the dichloromethane extract of the radix of Echinops ritro (Asteraceae) was the most potent. Bioassay-guided fractionation of this extract led to the isolation of eight thiophenes. Antifungal activities of isolated compounds together with a previously isolated thiophene from Echinops transiliensis were first evaluated by bioautography and subsequently evaluated in greater detail using a broth microdilution assay against plant pathogens Colletotrichum acutatum, Colletotrichum fragariae, Colletotrichum gloeosporioides, Botrytis cinerea, Fusarium oxysporum, Phomopsis viticola, and Phomopsis obscurans. 5'-(3-Buten-1-ynyl)-2,2'-bithiophen (1), alpha-terthienyl (2), and 2-[pent-1,3-diynyl]-5-[4-hydroxybut-1-ynyl]thiophene (5) at 3 and 30 microM were active against all three Colletotrichum species, F. oxysporum, P. viticola, and P. obscurans.
    Journal of Agricultural and Food Chemistry 04/2006; 54(5):1651-5. · 2.82 Impact Factor
  • Chapter: Clues in the search for new herbicides
    Franck E. Dayan, Stephen O. Duke
    12/2005: pages 63-83;
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    Article: Algicidal and antifungal compounds from the roots of Ruta graveolens and synthesis of their analogs.
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    ABSTRACT: Bioassay-guided fractionation of the ethyl acetate extract of Ruta graveolens roots yielded rutacridone epoxide with potent selective algicidal activity towards the 2-methyl-isoborneol (MIB)-producing blue-green alga Oscillatoria perornata, with relatively little effect on the green alga Selenastrum capricornutum. The diol-analog of rutacridone epoxide, gravacridondiol, which was also present in the same extract, had significantly less activity towards O. perornata. Rutacridone epoxide also showed significantly higher activity than commercial fungicides captan and benomyl in our micro-bioassay against the agriculturally important pathogenic fungi Colletotrichum fragariae, C. gloeosporioides, C. acutatum, and Botrytis cineara and Fusarium oxysporium. Rutacridone epoxide is reported as a direct-acting mutagen, precluding its use as an agrochemical. In order to understand the structure-activity relationships and to develop new potential biocides without toxicity and mutagenicity, some analogs containing the (2-methyloxiranyl)-dihydrobenzofuran moiety with an epoxide were synthesized and tested. None of the synthetic analogs showed comparable activities to rutacridone epoxide. The absolute stereochemistry of rutacridone was determined to be 2'(R) and that of rutacridone epoxide to be 2'(R), 3'(R) by CD and NMR analysis.
    Phytochemistry 12/2005; 66(22):2689-95. · 3.35 Impact Factor
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    Article: Phytotoxic and antifungal compounds from two Apiaceae species, Lomatium californicum and Ligusticum hultenii, rich sources of Z-ligustilide and apiol, respectively.
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    ABSTRACT: The seeds of two Apiaceae species, Ligusticum hultenii and Lomatium californicum, were investigated. Preliminary bioassays indicated that methylene chloride extracts of seeds of both species contained selective phytotoxic activity against monocots and antifungal activity against Colletotrichum fragariae. Active constituents were isolated by bioassay-guided fractionation, and the structures were elucidated by NMR and GC-MS as apiol and Z-ligustilide, isolated from L. hultenii and L. californicum, respectively. Apiol and Z-ligustilide had I50 values of about 80 and 600 microM, respectively, for inhibition of the growth of Lemna paucicostata. The methylene chloride (CH2Cl2) extracts of the seeds and the isolated and purified compounds were tested against the 2-methylisobomeol-producing cyanobacterium (blue-green alga) Oscillatoria perornata, and the green alga Selenastrum capricornutum. The CH2Cl2 extracts of both Apiaceae species and apiol were weakly toxic to both species of phytoplankton, while Z-ligustilide was toxic to both with a lowest complete inhibitory concentration (LCIC) of 53 microM. Seeds of L. californicum and L. hultenii were found to be rich sources of Z-ligustilide (97 mg/g of dry seed) and apiol (40 mg/g of dry seed), respectively.
    Journal of Chemical Ecology 08/2005; 31(7):1567-78. · 2.66 Impact Factor
  • Article: Detoxification and transcriptome response in Arabidopsis seedlings exposed to the allelochemical benzoxazolin-2(3H)-one.
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    ABSTRACT: Benzoxazolin-2(3H)-one (BOA) is an allelochemical most commonly associated with monocot species, formed from the O-glucoside of 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one by a two-step degradation process. The capacity of Arabidopsis to detoxify exogenously supplied BOA was analyzed by quantification of the major known metabolites BOA-6-OH, BOA-6-O-glucoside, and glucoside carbamate, revealing that detoxification occurs predominantly through O-glucosylation of the intermediate BOA-6-OH, most likely requiring the sequential action of as-yet-unidentified cytochrome P450 and UDP-glucosyltransferase activities. Transcriptional profiling experiments were also performed with Arabidopsis seedlings exposed to BOA concentrations, representing I(50) and I(80) levels based on root elongation inhibition assays. One of the largest functional categories observed for BOA-responsive genes corresponded to protein families known to participate in cell rescue and defense, with the majority of these genes potentially associated with chemical detoxification pathways. Further experiments using a subset of these genes revealed that many are also transcriptionally induced by a variety of structurally diverse xenobiotic compounds, suggesting they comprise components of a coordinately regulated, broad specificity xenobiotic defense response. The data significantly expand upon previous studies examining plant transcriptional responses to allelochemicals and other environmental toxins and provide novel insights into xenobiotic detoxification mechanisms in plants.
    Journal of Biological Chemistry 07/2005; 280(23):21867-81. · 4.77 Impact Factor
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    Article: Taking stock of herbicide-resistant crops ten years after introduction.
    Stephen O Duke
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    ABSTRACT: Since transgenic, bromoxynil-resistant cotton and glufosinate-resistant canola were introduced in 1995, planting of transgenic herbicide-resistant crops has grown substantially, revolutionizing weed management where they have been available. Before 1995, several commercial herbicide-resistant crops were produced by biotechnology through selection for resistance in tissue culture. However, non-transgenic herbicide-resistant crops have had less commercial impact. Since the introduction of glyphosate-resistant soybean in 1996, and the subsequent introduction of other glyphosate-resistant crops, where available, they have taken a commanding share of the herbicide-resistant crop market, especially in soybean, cotton and canola. The high level of adoption of glyphosate-resistant crops by North American farmers has helped to significantly reduce the value of the remaining herbicide market. This has resulted in reduced investment in herbicide discovery, which may be problematic for addressing future weed-management problems. Introduction of herbicide-resistant crops that can be used with selective herbicides has apparently been hindered by the great success of glyphosate-resistant crops. Evolution of glyphosate-resistant weeds and movement of naturally resistant weed species into glyphosate-resistant crop fields will require increases in the use of other herbicides, but the speed with which these processes compromise the use of glyphosate alone is uncertain. The future of herbicide-resistant crops will be influenced by many factors, including alternative technologies, public opinion and weed resistance. Considering the relatively few recent approvals for field testing new herbicide-resistant crops and recent decisions not to grow glyphosate-resistant sugarbeet and wheat, the introduction and adoption of herbicide-resistant crops during the next 10 years is not likely to be as dramatic as in the past 10 years.
    Pest Management Science 04/2005; 61(3):211-8. · 2.25 Impact Factor
  • Article: The potential for advances in crop allelopathy
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    ABSTRACT: The authors outline the known cases of crop allelopathy and point the way forward to using this technology commercially.
    Outlooks on Pest Management 03/2005; 16(2):64-68.
  • Article: Structural activity relationship studies of zebra mussel antifouling and antimicrobial agents from verongid sponges.
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    ABSTRACT: Several dibromotyramine derivatives including moloka'iamine were selected as potential zebra mussel (Dreissena polymorpha) antifoulants due to the noteworthy absence of fouling observed on sponges of the order Verongida. Sponges of the order Verongida consistently produce these types of bromotyrosine-derived secondary metabolites. Previously reported antifouling data for the barnacle Balanus amphitrite(EC50 = 12.2 microM) support the results reported here that the compound moloka'iamine may be a potential zebra mussel antifoulant compound (EC50 = 10.4 microM). The absence of phytotoxic activity of the compound moloka'iamine toward Lemna pausicostata and, most importantly, the compound's significant selectivity against macrofouling organisms such as zebra mussels suggest the potential utility of this compound as a naturally derived antifoulant lead.
    Journal of Natural Products 01/2005; 67(12):2117-20. · 3.13 Impact Factor

Institutions

  • 2000–2013
    • United States Department of Agriculture
      • Agricultural Research Service (ARS)
      Fort Collins, CO, USA
  • 2003–2011
    • University of Mississippi
      • Department of Pharmacognosy
      University, MS, USA
    • Second University of Naples
      • Dipartimento di Matematica e Fisica
      Napoli, Campania, Italy
  • 2010
    • Spanish National Research Council
      Madrid, Madrid, Spain
  • 2009
    • Kinki University
      Ōsaka-shi, Osaka-fu, Japan
  • 2008
    • University of Western Australia
      • School of Plant Biology
      Perth, Western Australia, Australia
  • 2006
    • University of Arkansas
      Fayetteville, AR, USA