Biotransformation of 2-Benzoxazolinone and 2-Hydroxy-1,4-Benzoxazin-3-one by Endophytic Fungi Isolated from
            <i>Aphelandra tetragona</i>

Zikmundová, Martina; Drandarov, Konstantin; Bigler, Laurent; Hesse, Manfred; Werner, Christa

doi:10.1128/aem.68.10.4863-4870.2002

Cited by 137 publications

(127 citation statements)

References 19 publications

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“…Several authors reported their presence in other systems in which these degradations take place (16,17). Their N-acetyl derivatives, 2-acetamidophenoxazin-3-one (AAPO) and 2-acetamido-7-methoxyphenoxazin-3-one (AAMPO) (Table 2, B), have been proposed as detoxification compounds produced by nonpathogenic organisms associated to Gramineae (15,18). APO has been already described as a potent phytotoxic agent for Echinochloa crus-galli (barnyardgrass) (16).…”

Section: Introductionmentioning

confidence: 99%

“…In general terms, natural 2,4-dihydroxybenzoxazin-3-ones (DIMBOA, DIBOA) ( In addition to this bioactivity research, the low stability of DIMBOA, DIBOA, and their related benzoxazolinones in several conditions, such as biotransformation by fungi (15), and degradation in crop soil (16,17) and in aqueous solution (8)(9)(10), has been investigated. We have recently developed a complete degradation study of these allelochemicals in wheat crop soil in which we observed and characterized the conversion dynamics of these compounds into several molecules carried out by soil microbial population (9,10).…”

Section: Introductionmentioning

confidence: 99%

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Structure−Activity Relationships (SAR) Studies of Benzoxazinones, Their Degradation Products and Analogues. Phytotoxicity on Standard Target Species (STS)

Macías

Marı́n

Oliveros‐Bastidas

et al. 2005

J. Agric. Food Chem.

106

140

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Benzoxazinones 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (DIMBOA) and 2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one (DIBOA) have been considered key compounds for understanding allelopathic phenomena in Gramineae crop plants such as corn (Zea mays L.), wheat (Triticum aestivum L.), and rye (Secale cereale L.). The degradation processes in the environment observed for these compounds, in which soil microbes are directly involved, could affect potential allelopathic activity of these plants. We present in this work a complete structure-activity relationships study based on the phytotoxic effects observed for DIMBOA, DIBOA, and their main degradation products, in addition to several synthetic analogues of them. Their effects were evaluated on standard target species (STS), which include Triticum aestivum L. . They showed high inhibitory activity over almost all species growth. The fact that APO is a degradation product from DIBOA with high phytotoxicity and stability makes it possible to assign an important ecological role regarding plant defense mechanisms. 2-Deoxy derivatives of natural benzoxazinones display a wide range of activities that allow proposing them as new leads for natural herbicide models with a 1,4-benzoxazine skeleton.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structure−Activity Relationships (SAR) Studies of Benzoxazinones, Their Degradation Products and Analogues. Phytotoxicity on Standard Target Species (STS)

Macías

Marı́n

Oliveros‐Bastidas

et al. 2005

J. Agric. Food Chem.

106

140

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“…Another maize pathogen, Gaumannomyces graminis var. tritici, transformed BOA to APO in liquid culture (Friebe et al 1998), and APO is now known to occur in cultures of several root endophytic fungi of tobacco, including F. sambucinum (Zikmundova et al 2002).…”

Section: Resultsmentioning

confidence: 99%

“…This ascomycetous fungus is consistently found in association with maize throughout the world as a symptomless endophyte (Kommedahl and Windels 1981;Marasas et al 1984;Bacon and Hinton 1996). The symptomless endophytic association with maize is apparently evolutionarily relevant, as it has been established that F. verticillioides and other endophytic fungi detoxify DIMBOA/MBOA and DIBOA/BOA by actively transforming them into the nontoxic components N-(2-hydroxy-4-methoxyphenyl) malonamic acid (HMPMA) and N-(2-hydroxyphenyl) malonamic acid (HPMA), respectively (Virtanen and Hietala 1955;Zikmundova et al 2002;Glenn et al 2003).…”

Section: Introductionmentioning

confidence: 99%

Interactions of Bacillus mojavensis and Fusarium verticillioides with a Benzoxazolinone (BOA) and its Transformation Product, APO

et al. 2007

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The benzoxazolinones, specifically benzoxazolin-2(3H)-one (BOA), are important transformation products of the benzoxazinones that can serve as allelochemicals providing resistance to maize from pathogenic bacteria, fungi, and insects. However, maize pathogens such as Fusarium verticillioides are capable of detoxifying the benzoxazolinones to 2-aminophenol (AP), which is converted to the less toxic N-(2-hydroxyphenyl) malonamic acid (HPMA) and 2-acetamidophenol (HPAA). As biocontrol strategies that utilize a species of endophytic bacterium, Bacillus mojavensis, are considered efficacious as a control of this Fusarium species, the in vitro transformation and effects of BOA on growth of this bacterium was examined relative to its interaction with strains of F. verticillioides. The results showed that a red pigment was produced and accumulated only on BOA-amended media when wild type and the progeny of genetic crosses of F. verticillioides are cultured in the presence of the bacterium. The pigment was identified as 2-amino-3H-phenoxazin-3-one (APO), which is a stable product. The results indicate that the bacterium interacts with the fungus preventing the usual transformation of AP to the nontoxic HPMA, resulting in the accumulation of higher amounts of APO than when the fungus is cultured alone. APO is highly toxic to F. verticillioides and other organisms. Thus, an enhanced biocontrol is suggested by this in vitro study.

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“…26 Endophytes have also been successfully used in the biotransformation of natural products. 27,28 These findings stimulated us to investigate about 20 endophytic strains from our collection of fungi 29 as biocatalyst systems and effective method for regio-and stereoselective production of novel and bioactive products. This procedure could convert unreactive methoxy groups to hydroxyl functions of a tetrahydrofuran lignan under mild conditions which may increase the solubility of 6.…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of a tetrahydrofuran lignan by the endophytic fungus Phomopsis Sp.

Verza¹,

Arakawa²,

Lopes³

et al. 2009

J. Braz. Chem. Soc.

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A biotransformação da lignana tetraidrofurânica, (-)-grandisina, pelo fungo endofítico Phomopsis sp, obtido de Viguiera arenaria, conduziu à formação de um novo metabólito caracterizado como 3,4-dimetil-2-(4'-hidróxi-3',5'-dimetóxifenil)-5-metóxi-tetraidrofurano. O metabólito foi analisado contra o parasita Trypanosoma cruzi, o agente causador da doença de Chagas, e mostrou uma atividade tripanocida (IC 50 9,8 µmol L -1 ) similar ao precursor natural (IC 50 3,7 µmol L -1 ).The biotrasformation of the tetrahydrofuran lignan, (-)-grandisin, by the endophitic fungus Phomopsis sp, obtained from Viguiera arenaria, led to the formation of a new compound determined as 3,4-dimethyl-2-(4'-hydroxy-3',5'-dimethoxyphenyl)-5-methoxy-tetrahydrofuran. The metabolite was evaluated against the parasite Trypanosoma cruzi, the causative agent of Chagas's disease, and showed a trypanocidal activity (IC 50 9.8 µmol L -1 ) similar to the natural precursor (IC 50 3.7 µmol L -1 ).Keywords: biotransformation, 2,5-diaryltetrahydrofuran, endophytic fungus, (-)-grandisin, trypanocidal activity IntroductionThe lignan family is a large group of natural products with noteworthy therapeutic activity as illustrated by podophyllotoxin derivatives (e. g. etoposide) with antitumoral activity. 1 In particular, the optically active tetrahydrofuran lignans display a wide range of pharmacological activities, including anti-parasite, 2-4 antibacterial, 5 antifungal, 6 antitumoral, 7 anti-inflammatory 8,9 and platelet-activating factor (PAF) inhibition. [10][11][12] Several non-symmetrical 2,5-diaryltetrahydrofuran lignans, shown in Table 1, have been isolated from Piper species (Piperaceae) containing either piperonyl, veratryl or 3,4,5-trimethoxyphenyl substituent at 2 and 5 positions and methyl groups at 3 and 4 positions attached to the tetrahydrofuran ring, as illustrated by (+)-calopiptin P. futokadsura, P. hancei, P. puberculum, P.wallichii), (-)-galbelgin (5, P. attenuatum, P. futokadsura, P. thomsoni, P. wightii), (+)-grandisin (6, P. polysyphorum), (+)-machilin G (7, P. schmidtii, P. wightii), (+)-veraguensin (8, P. cuneifolium, P. futokadsura, P. puberculum) and (-)-zuonin A (9, P. schmidtii). 13 Other bis-tetrahydrofuran lignans have also been described from Achillea lingulata (Asteraceae). 14 In previous reports, Martins et al. 3 described the isolation of (-)-grandisin (6) from Piper solmsianum and Lopes and co-workers 4,15 from Virola surinamensis (Rol.) Warb, which belong to Piperaceae and Myristicaceae, respectively. The tetrahydrofuran lignan (-)-grandisin (6) showed a potent trypanocidal activity against the trypomastigote form of Trypanosoma cruzi, responsible for Chagas´s disease in Latin America, at 5 µg mL -1 leading to a total parasite lysis after 24 h, without hematiae damage. 4 Furthermore, veraguensin (8) also isolated from Virola surinamensis 4 preserved this anti-parasite pattern along with a potent platelet-activating factor (PAF) inhibitory activity that may be involved in the mechanisms of the parasite growing and diffe...

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Biotransformation of 2-Benzoxazolinone and 2-Hydroxy-1,4-Benzoxazin-3-one by Endophytic Fungi Isolated from Aphelandra tetragona

Cited by 137 publications

References 19 publications

Structure−Activity Relationships (SAR) Studies of Benzoxazinones, Their Degradation Products and Analogues. Phytotoxicity on Standard Target Species (STS)

Structure−Activity Relationships (SAR) Studies of Benzoxazinones, Their Degradation Products and Analogues. Phytotoxicity on Standard Target Species (STS)

Interactions of Bacillus mojavensis and Fusarium verticillioides with a Benzoxazolinone (BOA) and its Transformation Product, APO

Biotransformation of a tetrahydrofuran lignan by the endophytic fungus Phomopsis Sp.

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