Benzoxazinone biosynthesis

Last updated
Enzymes, biosynthetic intermediates and subcellular location of the pathway are indicated. Benzoxazinoid biosynthesis in maize.png
Enzymes, biosynthetic intermediates and subcellular location of the pathway are indicated.

The biosynthesis of benzoxazinone, a cyclic hydroxamate and a natural insecticide, has been well-characterized in maize and related grass species. [1] In maize, genes in the pathway are named using the symbol bx. Maize Bx-genes are tightly linked, a feature that has been considered uncommon for plant genes of a biosynthetic pathways. Especially notable are genes encoding the different enzymatic functions BX1, BX2 and BX8 and which are found within about 50 kilobases. [1] [2] Results from wheat and rye indicate that the cluster is an ancient feature. [3] In wheat the cluster is split into two parts. The wheat genes Bx1 and Bx2 are located in close proximity on chromosome 4 and wheat Bx3, Bx4 and Bx5 map to the short arm of chromosome 5; an additional Bx3 copy was detected on the long arm of chromosome 5B. [3] Recently, additional biosynthetic clusters have been detected in other plants for other biosynthetic pathways and this organization might be common in plants. [4]

Maize genes

The bx1 gene encodes a protein, BX1, that forms indol from indol-3-glycerol phosphate in the plastid. It is the first step in the pathway and determines much of the natural variation in levels of DIMBOA in maize. [5] The next steps in the pathway occur in the endoplasmic reticulum, also referred to as the microsomes in cell fractionation experiments, and are carried by proteins encoded by genes bx2, bx3, bx4, and bx5.

Related Research Articles

Lysine α-amino acid

Lysine (symbol Lys or K) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO form under biological conditions), and a side chain lysyl ((CH2)4NH2), classifying it as a basic, charged (at physiological pH), aliphatic amino acid. It is encoded by the codons AAA and AAG. Like almost all other amino acids, the α-carbon is chiral and lysine may refer to either enantiomer or a racemic mixture of both. For the purpose of this article, lysine will refer to the biologically active enantiomer L-lysine, where the α-carbon is in the S configuration.

Protoporphyrinogen oxidase

Protoporphyrinogen oxidase or protox is an enzyme that in humans is encoded by the PPOX gene.

Apolipoprotein C-I

Apolipoprotein C-I is a protein component of lipoproteins that in humans is encoded by the APOC1 gene.

Coproporphyrinogen III oxidase

Coproporphyrinogen-III oxidase, mitochondrial is an enzyme that in humans is encoded by the CPOX gene. A genetic defect in the enzyme results in a reduced production of heme in animals. The medical condition associated with this enzyme defect is called hereditary coproporphyria.

DIMBOA Chemical compound

DIMBOA (2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one) is a naturally occurring hydroxamic acid, a benzoxazinoid. DIMBOA is a powerful antibiotic present in maize, wheat, and related grasses,

MYB (gene)

Myb genes are part of a large gene family of transcription factors found in animals and plants. In humans, it includes Myb proto-oncogene like 1 and Myb-related protein B in addition to MYB proper. Members of the extended SANT/Myb family also include the SANT domain and other similar all-helical homeobox-like domains.

In enzymology, an ent-copalyl diphosphate synthase is an enzyme that catalyzes the chemical reaction:

In enzymology, an indole-3-glycerol-phosphate lyase is an enzyme that catalyzes the chemical reaction

Zwittermicin A is an antibiotic that has been identified from the bacterium Bacillus cereus UW85. It is a molecule of interest to agricultural industry because it has the potential to suppress plant disease due to its broad spectrum activity against certain gram positive and gram negative prokaryotic micro-organisms. The molecule is also of interest from a metabolic perspective because it represents a new structural class of antibiotic and suggests a crossover between polyketide and non-ribosomal peptide biosynthetic pathways. Zwittermicin A is linear aminopolyol.

Phlobaphene

Phlobaphenes are reddish, alcohol-soluble and water-insoluble phenolic substances. They can be extracted from plants, or be the result from treatment of tannin extracts with mineral acids. The name phlobaphen come from the Greek roots φλoιὀς (phloios) meaning bark and βαφή (baphe) meaning dye.

Chlorophyllide-a oxygenase

Chlorophyllide-a oxygenase (EC 1.14.13.122), chlorophyllide a oxygenase, chlorophyll-b synthase, CAO) is an enzyme with systematic name chlorophyllide-a:oxygen 7-oxidoreductase. This enzyme catalyses the following chemical reactions

Indole-2-monooxygenase (EC 1.14.13.137, BX2 (gene), CYP71C4 (gene)) is an enzyme with systematic name indole,NAD(P)H:oxygen oxidoreductase (2-hydroxylating). This enzyme catalyses the following chemical reaction

Indolin-2-one monooxygenase (EC 1.14.13.138, BX3 (gene), CYP71C2 (gene)) is an enzyme with systematic name indolin-2-one,NAD(P)H:oxygen oxidoreductase (3-hydroxylating). This enzyme catalyses the following chemical reaction

3-hydroxyindolin-2-one monooxygenase (EC 1.14.13.139, BX4 (gene), CYP71C1 (gene)) is an enzyme with systematic name 3-hydroxyindolin-2-one,NAD(P)H:oxygen oxidoreductase (2-hydroxy-2H-1,4-benzoxazin-3(4H)-one-forming). This enzyme catalyses the following chemical reaction

2-Hydroxy-1,4-benzoxazin-3-one monooxygenase (EC 1.14.13.140, BX5 (gene), CYP71C3 (gene)) is an enzyme with systematic name 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one,NAD(P)H:oxygen oxidoreductase (N-hydroxylating). This enzyme catalyses the following chemical reaction

2,4-dihydroxy-1,4-benzoxazin-3-one-glucoside dioxygenase (EC 1.14.20.2, BX6 (gene), DIBOA-Glc dioxygenase) is an enzyme with systematic name (2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside:oxygen oxidoreductase (7-hydroxylating). This enzyme catalyses the following chemical reaction

2,4,7-trihydroxy-1,4-benzoxazin-3-one-glucoside 7-O-methyltransferase is an enzyme with systematic name S-adenosyl-L-methionine:(2R)-4,7-dihydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl β-D-glucopyranoside 7-O-methyltransferase. This enzyme catalyses the following chemical reaction

4-Hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase (EC 3.2.1.182, DIMBOAGlc hydrolase, DIMBOA glucosidase) is an enzyme with systematic name (2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside beta-D-glucosidase. This enzyme catalyses the following chemical reaction

Function Maize gene for first step in biosynthesis of benzoxazin, which aids in resistance to insect pests, pathogenic fungi and bacteria.

Plant–fungus horizontal gene transfer is the movement of genetic material between individuals in the plant and fungus kingdoms. Horizontal gene transfer is universal in fungi, viruses, bacteria, and other eukaryotes. Horizontal gene transfer research often focuses on prokaryotes because of the abundant sequence data from diverse lineages, and because it is assumed not to play a significant role in eukaryotes.

References

  1. 1 2 Frey, M; Chomet, P; Glawischnig, E; Stettner, C; Grün, S; Winklmair, A; Eisenreich, W; Bacher, A; Meeley, RB; Briggs, SP; Simcox, K; Gierl, A (Aug 1, 1997). "Analysis of a chemical plant defense mechanism in grasses". Science. 277 (5326): 696–9. doi:10.1126/science.277.5326.696. PMID   9235894.
  2. Frey, M; Kliem, R; Saedler, H; Gierl, A (Jan 6, 1995). "Expression of a cytochrome P450 gene family in maize". Molecular & General Genetics. 246 (1): 100–9. doi:10.1007/bf00290138. PMID   7823905. S2CID   29908288.
  3. 1 2 Nomura, T; Ishihara, A; Imaishi, H; Ohkawa, H; Endo, TR; Iwamura, H (Sep 2003). "Rearrangement of the genes for the biosynthesis of benzoxazinones in the evolution of Triticeae species". Planta. 217 (5): 776–82. doi:10.1007/s00425-003-1040-5. PMID   12734755. S2CID   28300768.
  4. Osbourn, A (Oct 2010). "Gene clusters for secondary metabolic pathways: an emerging theme in plant biology". Plant Physiology. 154 (2): 531–5. doi:10.1104/pp.110.161315. PMC   2949040 . PMID   20921179.
  5. Butrón, A; Chen, YC; Rottinghaus, GE; McMullen, MD (Feb 2010). "Genetic variation at bx1 controls DIMBOA content in maize" (PDF). TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik. 120 (4): 721–34. doi:10.1007/s00122-009-1192-1. hdl: 10261/24875 . PMID   19911162. S2CID   33310126.