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Chemical Compound Review

DIMBOA     8,10-dihydroxy-4-methoxy-7- oxa-10...

Synonyms: AGN-PC-00GJIJ, BEN215, SureCN912624, AG-K-98696, CHEBI:18048, ...
 
 
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Disease relevance of DIMBOA

  • Addition of DIMBOA to Al-containing nutrient solution protected the sensitive maize against Al toxicity as shown by bioassays using callose and haematoxylin staining of root tips as stress indicators [1].
 

High impact information on DIMBOA

  • DIMBOA at 0.1 mM concentration completely inhibited vir gene induction by 100 microM AS and reduced growth rate by 50% [2].
  • Bx8 is included in the cluster of DIMBOA biosynthesis genes located on the short arm of chromosome 4 [3].
  • Using this method, the characterization, separation, and quantitative detection of a mixture of six naturally occurring 1,4-benzoxazin-3(4H)-one derivatives, including the hydroxamic acids (DIMBOA, DIBOA), lactams (HBOA, and HMBOA), benzoxazilinones (BOA, MBOA), and two synthetic methoxylated variations of DIBOA and HBOA, was achieved [4].
  • Corn (Zea mays) is the primary host for F. verticillioides, and we have investigated the impact of the plant's antimicrobial compounds (DIMBOA, DIBOA, MBOA, and BOA) on fungal virulence and systemic colonization [5].
  • Activity tests confirmed that pure DIMBOA from other sources sustained auxin-induced elongation of short maize coleoptile segments [6].
 

Biological context of DIMBOA

  • The valuable genetic material with high levels of DIMBOA in the shoots or roots identified in the present research could be used to breed for wheat cultivars with elevated allelopathic activity [7].
 

Anatomical context of DIMBOA

  • HMBOA (3,4-dihydro-2-hydroxy-7-methoxy-2H-1,4-benzoxazin-3-one), the lactam precursor of DIMBOA, and a tentatively identified derivative of MBOA (2,3-dihydro-6-methoxy-benzoxazol-2-one) were detected in the corn root exudates [8].
  • Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA), two naturally occurring benzoxazinones contained in sprouts of Gramineae are potent aneugens in human-derived liver cells (HepG2) [9].
 

Associations of DIMBOA with other chemical compounds

 

Gene context of DIMBOA

  • Effects of DIMBOA on detoxification enzymes of the aphid Rhopalosiphum padi (Homoptera: aphididae) [10].
  • In cereals, therefore, DIMBOA may act by interfering with esterase- or GST-mediated detoxification of xenobiotics by aphids [10].
 

Analytical, diagnostic and therapeutic context of DIMBOA

  • The total amount of DIBOA and DIMBOA exuded showed a significant correlation to the growth inhibition in bioassay with a statistically estimated contribution to the overall allelopathic effect of 48-72% [11].

References

  1. A role for cyclic hydroxamates in aluminium resistance in maize? Poschenrieder, C., Tolrà, R.P., Barceló, J. J. Inorg. Biochem. (2005) [Pubmed]
  2. Corn metabolites affect growth and virulence of Agrobacterium tumefaciens. Sahi, S.V., Chilton, M.D., Chilton, W.S. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  3. Two glucosyltransferases are involved in detoxification of benzoxazinoids in maize. von Rad, U., Hüttl, R., Lottspeich, F., Gierl, A., Frey, M. Plant J. (2001) [Pubmed]
  4. Development of a liquid chromatography-electrospray-tandem mass spectrometry method for the quantitative determination of benzoxazinone derivatives in plants. Bonnington, L., Eljarrat, E., Guillamón, M., Eichhorn, P., Taberner, A., Barceló, D. Anal. Chem. (2003) [Pubmed]
  5. Fdb1 and Fdb2, Fusarium verticillioides loci necessary for detoxification of preformed antimicrobials from corn. Glenn, A.E., Gold, S.E., Bacon, C.W. Mol. Plant Microbe Interact. (2002) [Pubmed]
  6. Auxin-induced elongation of short maize coleoptile segments is supported by 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one. Park, W.J., Schäfer, A., Prinsen, E., van Onckelen, H., Kang, B.G., Hertel, R. Planta (2001) [Pubmed]
  7. Allelochemicals in wheat (Triticum aestivum L.): production and exudation of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one. Wu, H., Haig, T., Pratley, J., Lemerle, D., An, M. J. Chem. Ecol. (2001) [Pubmed]
  8. Effect of corn root exudates on the degradation of atrazine and its chlorinated metabolites in soils. Wenger, K., Bigler, L., Suter, M.J., Schönenberger, R., Gupta, S.K., Schulin, R. J. Environ. Qual. (2005) [Pubmed]
  9. Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA), two naturally occurring benzoxazinones contained in sprouts of Gramineae are potent aneugens in human-derived liver cells (HepG2). Buchmann, C.A., Nersesyan, A., Kopp, B., Schauberger, D., Darroudi, F., Grummt, T., Krupitza, G., Kundi, M., Schulte-Hermann, R., Knasmueller, S. Cancer Lett. (2007) [Pubmed]
  10. Effects of DIMBOA on detoxification enzymes of the aphid Rhopalosiphum padi (Homoptera: aphididae). Mukanganyama, S., Figueroa, C.C., Hasler, J.A., Niemeyer, H.M. J. Insect Physiol. (2003) [Pubmed]
  11. Differential exudation of two benzoxazinoids--one of the determining factors for seedling allelopathy of Triticeae species. Belz, R.G., Hurle, K. J. Agric. Food Chem. (2005) [Pubmed]
 
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