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Suresh Varsani; Sajjan Grover; Shaoqun Zhou; Kyle G. Koch; Pei-Cheng Huang; Michael V. Kolomiets; W. P. Williams; Tiffany Heng-Moss; Gautam Sarath; Dawn S. Luthe; Georg Jander; Joe Louis
... The corn leaf aphid (CLA; Rhopalosiphum maidis) is a phloem sap-sucking insect that attacks many cereal crops, including maize (Zea mays). We previously showed that the maize inbred line Mp708, which was developed by classical plant breeding, provides enhanced resistance to CLA. Here, using electrophysiological monitoring of aphid feeding behavior, we demonstrate that Mp708 provides phloem-mediate ...
... Fusarium head blight (FHB) is a devastating disease of wheat (Triticum aestivum L.) caused by a mycotoxigenic fungus Fusarium graminearum resulting in significantly decreased yields and accumulation of toxic trichothecenes in grains. We tested 7 major secondary metabolites from wheat for their effect on trichothecene production in liquid cultures of F. graminearum producing trichothecene 15-acetyl ...
... Allelopathy is a biochemical interaction between plants in which a donor plant releases secondary metabolites, allelochemicals, that are detrimental to the growth of its neighbours. Traditionally considered as bilateral interactions between two plants, allelopathy has recently emerged as a cross-kingdom process that can influence and be modulated by the other organisms in the plant’s environment. ...
... The contents of 1,4-benzoxazinone derivatives in wheat plants infected with Puccinia graminis Pers. f. sp. tritici Ericss. & Henn, race 32, and in uninfected controls were examined in four near-isogenic lines of different infection types: Triticum aestivum L., cultivar Prelude Sr5 (highly resistant), Sr24, Sr26 (moderately resistant), and srx (susceptible). In all infection types the contents of D ...
... Benzoxazinoids are highly studied compounds due to their biological activity and presence in several cereals. They include compound classes such as hydroxamic acids and lactams and usually occur as inactive glucosides in unstressed plants. Injury to the plant causes enzymatic hydrolysis of the inactive glucosides to the biologically active hydroxamic acid and lactam aglucones. The hydroxamic acids ...
... Natural toxins such as phytotoxins and mycotoxins have been studied in food and feed for decades, but little attention has yet been paid to their occurrence in the environment. Because of increasing awareness of the presence and potential relevance of micropollutants in the environment, phytotoxins and mycotoxins should be considered and investigated as part of the chemical cocktail in natural sam ...
... The ability of [1,2,3]triazolobenzoxazinones to act as a source of “hidden” diazo group was discovered. These diazo precursors can be easily prepared by the intramolecular cyclization of 2-(5-iodo-1,2,3-triazolyl)benzoic acids. The Cu-catalyzed capture of the hidden diazo group allows for further functionalization through the denitrogenative pathway. The transformations proceed via the formation o ...
... The Asian corn borer (Ostrinia furnacalis Guenée) is a destructive pest of maize (Zea mays L.). Despite large‐scale commercial maize production, little is known about the defensive responses of field‐grown commercial maize to O. furnacalis herbivory, and how these responses result in direct and indirect defence against this pest. To elucidate the maize transcriptome response to O. furnacalis feedi ...
... Two of major weeds affecting cereal crops worldwide are Avena fatua L. (wild oat) and Lolium rigidum Gaud. (rigid ryegrass). Thus, development of new herbicides against these weeds is required; in line with this, benzoxazinones, their degradation products, and analogues have been shown to be important allelochemicals and natural herbicides. Despite earlier structure–activity studies demonstrating ...
... To optimize fitness, plants must efficiently allocate their resources between growth and defense. Although phytohormone crosstalk has emerged as a major player in balancing growth and defense, the genetic basis by which plants manage this balance remains elusive. We previously identified a quantitative disease-resistance locus, qRfg2, in maize (Zea mays) that protects against the fungal disease Gi ...
Triticum aestivum; alkylresorcinols; antioxidant activity; benzoxazinoids; cultivars; free radicals; health promotion; phytochemicals; spring; value added; winter wheat; Poland
Abstract:
... The health-promoting properties of the grains of common wheat (Triticum aestivum L.) are associated with the presence of unique phytochemicals. This study determines the profile of alkylresorcinols (ARs) and benzoxazinoids (BXs) in T. aestivum spring and winter cultivars grown in Poland under the two different production systems: conventional and organic. Wheat grain extracts were subjected to qua ...
... Benzoxazinoids (BXs) are specialized metabolites with protective properties that are synthesized predominantly by Poaceae species, including rye (Secale cereale). Among factors known to influence BXs production, prolonged low temperature has not been studied previously. In this study, the influence of cultivation at 4 °C, which is essential for vernalization, on the concentration of BXs (HBOA, DIB ...
... Sweet broomweed (Scoparia dulcis) is an edible perennial medicinal herb widely distributed in tropical and subtropical regions of Asia, Africa, and the Americas. Four compounds, (2R)-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-O-β-galactopyranoside [(2R)-HMBOA-2-O-Gal], 3,6-dimethoxy-benzoxazolin-2(3H)-one (3,6-M2BOA), 3-hydroxy-6-methoxy-2-benzoxazolinone (3-OH-MBOA), and scutellarein 7-O-β-glucurona ...
... Rye bread contains high amounts of benzoxazinoids, and in vitro studies have shown suppressive effects of selected benzoxazinoids on prostate cancer cells. Thus, research into benzoxazinoids as possible suppressors of prostate cancer is demanded. A pilot study was performed in which ten prostate cancer patients received a rye-enriched diet 1 week prior to prostatectomy. Plasma and urine samples we ...
... The allelopathic potency of rye (Secale cereale L.) is due mainly to the presence of phytotoxic benzoxazinones—compounds whose biosynthesis is developmentally regulated, with the highest accumulation in young tissue and a dependency on cultivar and environmental influences. Benzoxazinones can be released from residues of greenhouse-grown rye at levels between 12 and 20 kg/ha, with lower amounts ex ...
... Cover crops provide many agroecosystem services, including weed suppression, which is partially exerted through release of allelopathic benzoxazinoid (BX) compounds. This research (1) characterizes changes in concentrations of BX compounds in shoots, roots, and soil at three growth stages (GS) of cereal rye (Secale cereale L.), and (2) their degradation in soil over time following termination. Con ...
Datasets:
Data from: Benzoxazinoids in roots and shoots of cereal rye (Secale cereale) and their fates in soil after cover crop termination
M. Iftikhar Hussain; Fabrizio Araniti; Margot Schulz; Scott Baerson; Yedra Vieites-Álvarez; Leonidas Rempelos; Paul Bilsborrow; Nuria Chinchilla; Francisco A. Macías; Leslie A. Weston; Manuel J. Reigosa; Adela M. Sánchez-Moreiras
... Allelopathic activity of wheat (Triticum aestivum L.) has previously been associated with the production of phenolic acids and flavonoids (PAF), benzoxazinones (BXZs) and phenoxazinones (PXZs). The biosynthesis of BXZs is closely regulated during cereal growth, with accumulation highest in young tissues with variation associated with genotype and environmental conditions. This review is focused on ...
Khem B. Adhikari; Fariha Tanwir; Per L. Gregersen; Stine K. Steffensen; Bettina M. Jensen; Lars K. Poulsen; Claus H. Nielsen; Søren Høyer; Michael Borre; Inge S. Fomsgaard
alkylresorcinols; animal models; benzoxazinoids; breads; breakfast cereals; central nervous system; functional foods; humans; in vitro studies; ingredients; lignans; medicinal plants; medicinal properties; phenolic acids; phytopharmaceuticals; reproductive system; small cereal grains; weight loss
Abstract:
... Benzoxazinoids (BXs) are a group of natural chemical compounds with putative pharmacological and health‐protecting properties. BXs were formerly identified in and isolated from selected dicot medicinal plants and young cereal plants. Recently, BXs were found to be present in mature cereal grains and bakery products, such that knowledge about the pharmacological properties of BXs, which until now h ...
aniline; benzoxazinoids; catalytic activity; chemical reactions; chemical structure; nitrophenols
Abstract:
... Benzoxazinones are easily prepared using Passerini–Smiles couplings of o-nitrophenol derivatives. Palladium-catalyzed flow-hydrogenation of adducts gives aniline derivatives that cyclize into benzoxazinones on treatment with trifluoroacetic acid. ...
atrazine; benzoxazinoids; chlorides; chromatography; soil pollution; spectroscopy; stoichiometry; water pollution; water resources
Abstract:
... The role of benzoxazinones (Bx, 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one) in triazine resistance in plants has been studied for over half a century. In this research, fundamental parameters of the reaction between DIBOA-Glc (2-β-d-glucopyranosyloxy-4-hydroxy-1,4-benzoxazin-3-one) and atrazine (ATR, 6-chloro-N-ethyl-N′-(1-methylethyl)-1,3,5-triazine-2,4-diamine) were examined. Through a series of expe ...
... Benzoxazinoids are a class of indole-derived plant metabolites that function in defense against numerous pests and pathogens. Due to their abundance in maize (Zea mays) and other important cereal crops, benzoxazinoids have been the subject of extensive research for >50 years. Whereas benzoxazinoids can account for 1% or more of the dry weight in young seedlings constitutively, their accumulation i ...
benzoxazinoids; bioactive properties; bioavailability; blood; breads; digestibility; high performance liquid chromatography; mass spectrometry; metabolism; rye; secondary metabolites; swine; urine
Abstract:
... Recently, bioactive benzoxazinoids were discovered in cereal grains and bakery products. In this study, we studied the uptake, distribution, and metabolism of these secondary metabolites using a pig model. Twelve benzoxazinoid compounds and their 4 transformation products were quantified in the pigs’ diets and biofluids using high-performance liquid chromatography coupled to electrospray ionizatio ...
... Whole wheat provides a rich source of bioactive phytochemicals namely, phenolic acids, carotenoids, tocopherols, alkylresorcinols, benzoxazinoids, phytosterols, and lignans. This review provides information on the distribution, extractability, analysis, and functional properties of bioactive phytochemicals present in wheat. Understanding the impact of processing on wheat phytochemicals allows us t ...
Stine K. Steffensen; Khem B. Adhikari; Bente B. Laursen; Claudia Jensen; Per L. Gregersen; Bina Bhattarai; Lovisa Martín Maraís; Heidi Schnorr; Bettina M. Jensen; Lars K. Poulsen; Claus H. Nielsen; Mette Borre; Michael Borre; Søren Høyer; Inge S. Fomsgaard
... The presence of bioactive benzoxazinoids (BXs) in mature whole grain and experimental bread products was recently shown. The aim of this study was to reveal the level of BXs in a broad range of commercial cereal products and discuss these findings in relation to ingredients and preparation processes. The concentrations of 11 BX compounds were determined by liquid chromatography–triple quadrupole m ...
benzoxazinoids; anti-inflammatory activity; lipopolysaccharides; 2,2-diphenyl-1-picrylhydrazyl; verbascoside; high performance liquid chromatography; carbon; Acanthus mollis; urinary tract; stable isotopes; inhibitory concentration 50; electrospray ionization mass spectrometry; macrophages; mucosa; superoxide anion; enzyme inhibition; leaves; traditional medicine; Toll-like receptor 4; cytotoxicity; linoleate 13S-lipoxygenase; bioactive compounds; in vitro studies; keratinocytes; antioxidant activity; ethanol; chemical structure; nuclear magnetic resonance spectroscopy; nitric oxide; therapeutics; chemical constituents of plants; analgesics; agonists; Mediterranean region
Abstract:
... Acanthus mollis is a plant native to the Mediterranean region, traditionally used as diuretic, anti-inflammatory and soothing of the mucous membranes of the digestive and urinary tract and externally as healing of wounds and burns, also demonstrating analgesic and anti-inflammatory activities. However, studies focused on its phytochemical composition as well as scientific proof of Acanthus mollis ...
NAD (coenzyme); NADP (coenzyme); benzoxazinoids; biomimetics; catalysts; chemical reactions; enantioselectivity; hydrogen bonding; models
Abstract:
... Using ureas as transfer catalysts through hydrogen bonding activation, biomimetic asymmetric reduction of benzoxazinones and quinoxalinones with chiral and regenerable NAD(P)H models was described, giving chiral dihydrobenzoxazinones and dihydroquinoxalinones with high yields and excellent enantioselectivities. A key dihydroquinoxalinone intermediate of a BRD4 inhibitor was synthesized using biomi ...
... Benzoxazinoids are secondary metabolites with plant defense properties and possible health-promoting effects in humans. In this study, the transcriptional activity of ScBx genes (ScBx1-ScBx5; ScBx6-like), involved in benzoxazinoid biosynthesis, was analyzed during germination and early seedling development in rye. Our results showed that ScBx genes had highest levels of expression at 24–30 h after ...
benzoxazinoids; catalysts; chemical reactions; chemical structure; density functional theory; gold; nuclear magnetic resonance spectroscopy; organic chemistry
Abstract:
... Metal catalyzed post-Ugi cyclization of bis-amides is reported in this study. Exposure of bis-amides to Pd(II) catalyst triggered the formation of seven-membered benzoxazepinones. This investigation established that changing the catalyst to a Echavarren’s gold(I) turned off cyclization to seven member ring and turned on 6-exo-dig annulations to afford family of six-membered benzoxazinones. To supp ...
... Rye bran is a rich source of phytochemicals, such as alkylresorcinols, benzoxazinoids, and phenolic acids, which likely are attributing to the positive health effects of whole-grain foods. In this study, we examined the effect of two types of bioprocessing of rye bran on the phytochemical profile as compared with non-processed rye bran, using a non-targeted LC–MS metabolomics method. The four brea ...
... Benzoxazinoids (BXs) are secondary metabolites synthesized mainly by gramineous plants, including rye (Secale cereale L.), that play an important role in stress resistance and allelopathy. In the present work, the influence of cocultivation of rye with berseem clover (Trifolium alexandrinum L.) on the expression of BX synthesis‐regulating genes (ScBx1–ScBx5, ScIgl, and ScGT) and the content of six ...
... Benzoxazinoids represent preformed protective and allelophatic compounds that are found in a multitude of species of the family Poaceae (Gramineae) and occur sporadically in single species of phylogenetically unrelated dicots. Stabilization by glucosylation and activation by hydrolysis is essential for the function of these plant defense compounds. We isolated and functionally characterized from t ...
... BACKGROUND: Young wheat plants are continuously exposed to herbivorous insect attack. To reduce insect damage and maintain their growth, plants evolved different defense mechanisms, including the biosynthesis of deterrent compounds named benzoxazinoids, and/or trichome formation that provides physical barriers. It is unclear whether both of these mechanisms are equally critical in providing an eff ...
... In maize (Zea mays ssp. mays), agriculturally damaging herbivores include lepidopteran insects, such as the European corn borer (Ostrinia nubilalis), and distantly related arthropods, like the two‐spotted spider mite (Tetranychus urticae). A small number of maize lines, including B96 and B75, are highly resistant to both herbivores, and B96 is also resistant to thrips. Using T. urticae as a repres ...
additives; benzoxazinoids; catalysts; chemical reactions; chemical structure; copper; indoles; oxidants; oxygen; solvents
Abstract:
... We developed an efficient method for the transformation of indoles by utilizing a copper catalyst and molecular oxygen as the oxidant. The transformation involves a tandem oxidative process of 2-arylindoles. Our reaction afforded a variety of N-benzoyl anthranilic acids and benzoxazinones. Our investigation revealed that the choice of solvent and additives is critical in these reactions. ...
... Fusarium infection in wheat causes Fusarium head blight, resulting in yield losses and contamination of grains with trichothecenes. Some plant secondary metabolites inhibit accumulation of trichothecenes. Eighteen Fusarium infected wheat cultivars were harvested at five time points and analyzed for the trichothecene deoxynivalenol (DON) and 38 wheat secondary metabolites (benzoxazinoids, phenolic ...
... Plants have sophisticated defense systems to fend off insect herbivores. How plants defend against herbivores in dicotyledonous plants, such as Arabidopsis and tobacco, have been relatively well studied, yet little is known about the defense responses in monocotyledons. Here, we review the current understanding of rice (Oryza sativa) and maize (Zea mays) defense against insects. In rice and maize, ...
... BACKGROUND: Plants can respond to insect attack via defense mechanisms that reduce insect performance. In this study, we examined the effects of several treatments applied to two maize genotypes (one resistant, one susceptible) on the subsequent growth and survival of Sesamia nonagrioides Lef. (Mediterranean corn borer, MCB) larvae. The treatments were infestation with MCB larvae, application of M ...
... The defense of plants against herbivores and pathogens involves the participation of an enormous range of different metabolites, some of which act directly as defensive weapons against enemies (toxins or deterrents) and some of which act as components of the complex internal signaling network that insures that defense is timed to enemy attack. Recent work reveals a surprising trend: The same compo ...
... Hydroxamic acid 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-one (DIMBOA) was isolated from maize phloem sap as a compound enhancing the degradation of isopentenyl adenine by maize cytokinin dehydrogenase (CKX), after oxidative conversion by either laccase or peroxidase. Laccase and peroxidase catalyze oxidative cleavage of DIMBOA to 4-nitrosoresorcinol-1-monomethyl ether (coniferron), which serves as a ...
... Phenolic compounds in beer have received considerable interest. Besides the more typical phenolic acids and flavonoids, beer contains also lesser-known compounds, such as hordatines, their agmatine precursors and other phenolamines. Current work shows that beers brewed from wheat or rye malts, in addition to barley malts, contain benzoxazinoids, a group of nitrogen containing secondary metabolites ...
Dres Damgaard; Bettina Margrethe Jensen; Yaseelan Palarasah; Michael Friberg Bruun Nielsen; Khem Bahadur Adhikari; Heidi Julius Schnoor; Nanna Juel‐Berg; Lars K. Poulsen; Inge S. Fomsgaard; Claus Henrik Nielsen
... SCOPE: To examine potentially immunomodulating effects of dietary benzoxazinoids (BXs), present in cereal grains. METHODS AND RESULTS: Nineteen healthy volunteers were randomly distributed into two groups, who received diets with high or low content of BXs for 3 wk. After a week's wash‐out, the groups switched diets. Peripheral blood mononuclear cells (PBMCs) were stimulated with Porphyromonas gin ...
Florent D. Lavergne; Corey D. Broeckling; Kitty J. Brown; Darren M. Cockrell; Scott D. Haley; Frank B. Peairs; Stephen Pearce; Lisa M. Wolfe; Courtney E. Jahn; Adam L. Heuberger
... Common wheat (Triticum aestivum L.) is a global staple crop, and insect pests can impact grain yield. The wheat stem sawfly (Cephus cinctus, WSS) is a major wheat pest, and while partial resistance has been deployed by breeding for a solid-stem trait, this trait is affected by environment. Here, a proteomics and metabolomics study was performed on four wheat cultivars to characterize a molecular r ...
... A new and easily regenerable NAD(P)H model 9,10-dihydrophenanthridine (DHPD) has been designed for biomimetic asymmetric hydrogenation of imines and aromatic compounds. This reaction features the use of hydrogen gas as terminal reductant for the regeneration of the DHPD under the mild condition. Therefore, the substrate scope is not limited in benzoxazinones; the biomimetic asymmetric hydrogenatio ...
... Collectively plants synthesise a diverse array of secondary metabolites. Secondary metabolites are well known as agents that mediate pollination and seed dispersal. They may also act as chemical defenses that ward off pests and pathogens or suppress the growth of neighbouring plants. The ability to synthesise particular classes of secondary metabolite is commonly restricted to selected plant group ...
... The Poaceae is a large taxonomic group consisting of approximately 12,000 species and is classified into 12 subfamilies. Gramine and benzoxazinones (Bxs), which are biosynthesized from the tryptophan pathway, are well-known defensive secondary metabolites in the Poaceae. We analyzed the presence or absence of garamine and Bxs in 64 species in the Poaceae by LC-MS/MS. We found that Hordeum brachyan ...
X-ray diffraction; aromatic compounds; benzoxazinoids; chemical reactions
Abstract:
... A new straightforward access to benzoxazinones based on a three-component coupling is presented here. The mechanism of the whole process involves a double aryl transfer as clearly underlined by the X-ray diffraction analysis of the products. ...
... The plant O-methyltransferases are dependent on S-Adenosyl-l-methionine, which can catalyze a variety of secondary metabolites. Here we identified different number of OMT genes from the respective grass genomes. Phylogenetic analysis showed that this OMT gene family is a grass-specific gene family that is different from COMT. Most of genes were expanded by tandem and segment duplication after the ...
... DIMBOA (3,4-dihydro-2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one), a major benzoxazinone of Poaceae plants, was isolated and purified from corn seedlings. The effect of isolated and purified DIMBOA on the degradation of atrazine [2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine], and its toxic breakdown products, desethylatrazine [2-chloro-4-amino-6-(isopropylamino)-s-triazine; DEA] and de ...
... There is a rotational cropping system of wheat and rice in many areas. Wheat plants contain significant amounts of glucopyranosides of 6-methoxy-benzoxazolin-2(3H)-one (MBOA) and benzoxazolin-2(3H)-one (BOA). After crop harvesting, MBOA and BOA are produced during the degradation process of wheat residues left in the field. The purpose of this study was evaluation for the effect of MBOA and BOA on ...
... Benzoxazinoids are constitutively produced secondary metabolites in maize that protect the plant from the negative effects of insect herbivores. In this study, we determined the effects of benzoxazinoids on the maize specialist Diabrotica virgifera virgifera and a congeneric generalist Diabrotica undecimpunctata howardi. We compared the survival, growth and development of larvae fed on maize line ...