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MetaCyc Pathway: DIMBOA-glucoside biosynthesis

Enzyme View:

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: DIMBOA biosynthesis

Superclasses: Biosynthesis Secondary Metabolites Biosynthesis

Some taxa known to possess this pathway include ? : Aphelandra squarrosa , Coix lacryma-jobi , Triticum aestivum , Zea mays

Expected Taxonomic Range: Magnoliophyta

Summary:
General Background

Benzoxazinoids were identified in the early 1960s as secondary metabolites of the grasses (including the major agricultural crops maize (Zea mays), wheat (Triticum aestivum), and rye (Secale cereale)) that function as natural pesticides and exhibit allelopathic properties [Barnes87, Sicker00]. Benzoxazinoids are synthesized in two subfamilies of the Poaceae and sporadically in single species of the dicots [Frey09]. They play an important role in defense against pests such as insects, pathogenic fungi and bacteria [Niemeyer88]. The most common benzoxazinoids are DIBOA and DIMBOA.

Since the aglycone benzoxazinoids are autotoxic, they are stored in glucosylated forms that have reduced chemical reactivity [Sicker00]. The glucosides are stored in the vacuoles [Osbourn96]. This allows the plants to store the toxic compounds in anticipation of pathogen attacks, prompting the suggestion to name these compounds "phytoanticipins".

For the sythesis of DIBOA-β-D-glucoside, please see DIBOA-glucoside biosynthesis.

About This Pathway

While DIBOA is the main benzoxazinoid in some plants, including barley, in most other benzoxazinoid-producing plants, such as maize, DIBOA-β-D-glucoside is further converted to DIMBOA-β-D-glucoside [Frey09] by a two-step hydroxylation/methylation at position C7, catalyzed by Bx6 and Bx7, respectively [Jonczyk08].

In addition, DIMBOA-β-D-glucoside has been reported to be further methylated in maize into HMDBOA-glucoside [Oikawa02]. HMDBOA-glucoside is relatively lipophilic amongst benzoxazinoid glucosides, a property that may affect its absorption by pathogens at the site of interaction [Oikawa02]. A number of defense reaction elicitors (chitin and chitosan fragments, heavy metal ions such as copper and jasmonic acid) have been shown to lead to the production of HDMBOA-glucoside in wheat, maize and Job's Tears plants [Oikawa01, Oikawa02].

Superpathways: superpathway of benzoxazinoid glucosides biosynthesis

Credits:
Created 28-Oct-2011 by Caspi R , SRI International


References

Barnes87: Barnes J.P., Putnam A.R. "Role of benzoxazinones in allelopathy by rye (Secale cereale L.)." J. Chem. Ecol. (1987) 13 : 889-906.

Frey09: Frey M, Schullehner K, Dick R, Fiesselmann A, Gierl A (2009). "Benzoxazinoid biosynthesis, a model for evolution of secondary metabolic pathways in plants." Phytochemistry 70(15-16);1645-51. PMID: 19577780

Jonczyk08: Jonczyk R, Schmidt H, Osterrieder A, Fiesselmann A, Schullehner K, Haslbeck M, Sicker D, Hofmann D, Yalpani N, Simmons C, Frey M, Gierl A (2008). "Elucidation of the final reactions of DIMBOA-glucoside biosynthesis in maize: characterization of Bx6 and Bx7." Plant Physiol 146(3);1053-63. PMID: 18192444

Niemeyer88: Niemeyer H.M. (1988). "Hydroxamic acids (4-hydroxy-1,4-benzoxazin-3-ones), defence chemicals in the gramineae." Phytochemistry 27(11) : 3349-3358.

Oikawa01: Oikawa A, Ishihara A, Hasegawa M, Kodama O, Iwamura H (2001). "Induced accumulation of 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one glucoside (HDMBOA-Glc) in maize leaves." Phytochemistry 56(7);669-75. PMID: 11314951

Oikawa02: Oikawa A, Ishihara A, Iwamura H (2002). "Induction of HDMBOA-Glc accumulation and DIMBOA-Glc 4-O-methyltransferase by jasmonic acid in poaceous plants." Phytochemistry 61(3);331-7. PMID: 12359519

Osbourn96: Osbourn AE (1996). "Preformed Antimicrobial Compounds and Plant Defense against Fungal Attack." Plant Cell 8(10);1821-1831. PMID: 12239364

Sicker00: Sicker D, Frey M, Schulz M, Gierl A (2000). "Role of natural benzoxazinones in the survival strategy of plants." Int Rev Cytol 198;319-46. PMID: 10804466

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Frey03: Frey M, Huber K, Park WJ, Sicker D, Lindberg P, Meeley RB, Simmons CR, Yalpani N, Gierl A (2003). "A 2-oxoglutarate-dependent dioxygenase is integrated in DIMBOA-biosynthesis." Phytochemistry 62(3);371-6. PMID: 12620350

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Dec 19, 2014, BIOCYC14B.