Microbial transformation products of benzoxazolinone and benzoxazinone allelochemicals––a review

Fomsgaard, Inge S.; Mortensen, Alan; Carlsen, Sandra C.K.

doi:10.1016/j.chemosphere.2003.09.044

Cited by 112 publications

(123 citation statements)

References 37 publications

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“…However, interactive microbial activity was not considered relevant. As established here and by others (Gagliardo and Chilton 1992;Fomsgaard et al 2004;Fritz and Braun 2006), however, APO is an important microbial transformation product of AP, although the interactions are perhaps exceeding complexity as observed here and by others (Macias et al 2005;Knop et al 2007). Fig.…”

Section: Resultssupporting

confidence: 78%

“…2c), indicating that fungal growth and activity are required for the production of transformation products from BOA. It is established that the transformation of BOA follows several steps that lead first to 2-aminophenol (AP), which is a microbial transformation product (Nair et al 1990;Gagliardo and Chilton 1992;Glenn et al 2002;Fomsgaard et al 2004), and subsequently microbial transformations or natural oxidative processes lead to the formation of 10 aminophenoxazinones (Fomsgaard et al 2004). That B. mojavensis is required for the accumulation of APO is indicated in those cultures that showed a greater intensity of pigment accumulation over cultures that did not contain both the bacteria and fungi, and absent in nutrient broth without the addition of BOA (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…The identity of APO resulting from biotransformation of BOA by F. verticillioides was indicated by its bright red color (Anzai et al 1960;Gagliardo and Chilton 1992) and by comparing TLC R f values with standards, as well as by comparing the absorption spectra with authentic APO after eluting it with methanol from the silica gel (Glenn et al 2003;Fomsgaard et al 2004). Further, the confirmation of APO as the decomposition product was based on established published procedures by comparison to a standard of the authentic compound (Macias et al 2005;Fomsgaard 2006) by using absorption spectroscopy, and gas chromatography-mass spectroscopy (GS-MS), described earlier (Glenn et al , 2003Fomsgaard 2006).…”

Section: Fungal and Bacterial Strainsmentioning

confidence: 99%

“…These benzoxazinones are present in maize mainly as glycosides, but upon injury from insects or pathogens they are degraded to their unstable and highly toxic agluconic forms, which spontaneously decompose to the corresponding benzoxazolinones, such as MBOA (6-methoxy-2-benzoxazolinone) and BOA (benzoxazolin-2-one) (Niemeyer 1988). Thus, MBOA and BOA are found in plant debris and soil as stable degradation products of DIMBOA and DIBOA, and are considered potentially useful allelochemicals (Fomsgaard et al 2004).…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Resultssupporting

confidence: 78%

Section: Resultsmentioning

confidence: 99%

Section: Fungal and Bacterial Strainsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2007

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“…When the modification is prevented due to a genetic mutation (FDB2), nontoxic 2-acetamidophenol (HPAA) may accumulate as a result of acetylation (49). During the BOA detoxification process, 2AP can also be spontaneously oxidized to produce 2-amino-3H-phenoxazin-3-one (APO), which is highly toxic to F. verticillioides (50) and exhibits greater allelopathic phytotoxicity toward barnyard grass (Echinochloa crus-galli) than BOA (51,52). Doratomyces stemonitis can utilize APO as a sole carbon source, but the utilization of this product seems to have a high energy demand (53).…”

Section: Resultsmentioning

confidence: 99%

Metabolic Pathway Involved in 6-Chloro-2-Benzoxazolinone Degradation by Pigmentiphaga sp. Strain DL-8 and Identification of the Novel Metal-Dependent Hydrolase CbaA

Dong

Wang

Huang

et al. 2016

Appl Environ Microbiol

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ABSTRACT6-Chloro-2-benzoxazolinone (CDHB) is a precursor of herbicide, insecticide, and fungicide synthesis and has a broad spectrum of biological activity. Pigmentiphaga sp. strain DL-8 can transform CDHB into 2-amino-5-chlorophenol (2A5CP), which it then utilizes as a carbon source for growth. The CDHB hydrolase (CbaA) was purified from strain DL-8, which can also hydrolyze 2-benzoxazolinone (BOA), 5-chloro-2-BOA, and benzamide. The specific activity of purified CbaA was 5,900 U · mg protein ؊1for CDHB, with K m and k cat values of 0.29 mM and 8,500 s ؊1 , respectively. The optimal pH for purified CbaA was 9.0, the highest activity was observed at 55°C, and the inactive metal-free enzyme could be reactivated by Mg 2؉ , Ni 2؉ , Ca 2؉ , or Zn 2؉ . Based on the results obtained for the CbaA peptide mass fingerprinting and draft genome sequence of strain DL-8, cbaA (encoding 339 amino acids) was cloned and expressed in Escherichia coli BL21(DE3). CbaA shared 18 to 21% identity with some metal-dependent hydrolases of the PF01499 family and contained the signature metal-binding motif Q 127 XXXQ 131 XD 133 XXXH 137 . The conserved amino acid residues His288 and Glu301 served as the proton donor and acceptor. E. coli BL21(DE3-pET-cbaA) resting cells could transform 0.2 mM CDHB into 2A5CP. The mutant strain DL-8⌬cbaA lost the ability to degrade CDHB but retained the ability to degrade 2A5CP, consistent with strain DL-8. These results indicated that cbaA was the key gene responsible for CDHB degradation by strain DL-8. IMPORTANCE2-Benzoxazolinone (BOA) derivatives are widely used as synthetic intermediates and are also an important group of allelochemicals acting in response to tissue damage or pathogen attack in gramineous plants. However, the degradation mechanism of BOA derivatives by microorganisms is not clear. In the present study, we reported the identification of CbaA and metabolic pathway responsible for the degradation of CDHB in Pigmentiphaga sp. DL-8. This will provide microorganism and gene resources for the bioremediation of the environmental pollution caused by BOA derivatives. 6-Chloro-2-benzoxazolinone (CDHB) is the precursor of fenoxaprop-p-ethyl (FE) and metamifop synthesis (1). FE is a postemergence aryloxyphenoxy propionate (AOPP) herbicide that is used to control annual and perennial weeds in crops, such as soybean, turf, and wheat (2, 3). Many studies have demonstrated that FE can be hydrolyzed to fenoxaprop acid (FA) and further transformed into CDHB and 2-(4-hydroxyphenoxy)-propionic acid (HPP) by soil microorganisms (4-6). Recently, the hydrolysis of FE to FA by several esterases from different microorganisms has been reported (7-9). However, the underlying genes and the metabolic pathway responsible for the degradation of CDHB in microorganisms are unknown.CDHB is a type of 2-benzoxazolinone (BOA) derivative. BOA is widely used as a synthetic intermediate of related derivatives and is an important group of allelochemicals that respond to tissue damage or pathogen attack in gramineous plants, s...

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Silica‐immobilized enzymes for multi‐step synthesis in microfluidic devices

Luckarift

Dordick

et al. 2007

Biotech & Bioengineering

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The combinatorial synthesis of 2-aminophenoxazin-3-one (APO) in a microfluidic device is reported. Individual microfluidic chips containing metallic zinc, silica-immobilized hydroxylaminobenzene mutase and silica-immobilized soybean peroxidase are connected in series to create a chemo-enzymatic system for synthesis. Zinc catalyzes the initial reduction of nitrobenzene to hydroxylaminobenzene which undergoes a biocatalytic conversion to 2-aminophenol, followed by enzymatic polymerization to APO. Silica-immobilization of enzymes allows the rapid stabilization and integration of the biocatalyst within a microfluidic device with minimal preparation. The system proved suitable for synthesis of a complex natural product (APO) from a simple substrate (nitrobenzene) under continuous flow conditions.

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Microbial transformation products of benzoxazolinone and benzoxazinone allelochemicals––a review

Cited by 112 publications

References 37 publications

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

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

Metabolic Pathway Involved in 6-Chloro-2-Benzoxazolinone Degradation by Pigmentiphaga sp. Strain DL-8 and Identification of the Novel Metal-Dependent Hydrolase CbaA

Silica‐immobilized enzymes for multi‐step synthesis in microfluidic devices

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