3-hydroxyindolin-2-one monooxygenase

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3-hydroxyindolin-2-one monooxygenase
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EC no. 1.14.13.139
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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). [1] [2] [3] This enzyme catalyses the following chemical reaction

3-hydroxyindolin-2-one + NAD(P)H + H+ + O2 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one + NAD(P)+ + H2O

3-hydroxyindolin-2-one monooxygenase is involved in the biosynthesis of protective and allelopathic benzoxazinoids in some plants.

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<span class="mw-page-title-main">DIMBOA</span> 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, rye, and related grasses,

In enzymology, a hydroxylamine reductase (NADH) (EC 1.7.1.10) is an enzyme that catalyzes the chemical reaction.

The enzyme indole-3-glycerol-phosphate lyase catalyzes the chemical reaction

<span class="mw-page-title-main">Loline alkaloid</span> Class of chemical compounds

A loline alkaloid is a member of the 1-aminopyrrolizidines, which are bioactive natural products with several distinct biological and chemical features. The lolines are insecticidal and insect-deterrent compounds that are produced in grasses infected by endophytic fungal symbionts of the genus Epichloë. Lolines increase resistance of endophyte-infected grasses to insect herbivores, and may also protect the infected plants from environmental stresses such as drought and spatial competition. They are alkaloids, organic compounds containing basic nitrogen atoms. The basic chemical structure of the lolines comprises a saturated pyrrolizidine ring, a primary amine at the C-1 carbon, and an internal ether bridge—a hallmark feature of the lolines, which is uncommon in organic compounds—joining two distant ring carbons. Different substituents at the C-1 amine, such as methyl, formyl, and acetyl groups, yield loline species that have variable bioactivity against insects. Besides endophyte–grass symbionts, loline alkaloids have also been identified in some other plant species; namely, Adenocarpus species and Argyreia mollis.

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

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

2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-D-glucosyltransferase is an enzyme with systematic name UDP-alpha-D-glucose:2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-beta-D-glucosyltransferase. This enzyme catalyses the following chemical reaction

The enzyme 1,4-dihydroxy-2-naphthoyl-CoA hydrolase (EC 3.1.2.28; systematic name 1,4-dihydroxy-2-naphthoyl-CoA hydrolase) catalyses the following 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

Aldos-2-ulose dehydratase (EC 4.2.1.110, pyranosone dehydratase, AUDH, 1,5-anhydro-D-fructose dehydratase (microthecin-forming)) is an enzyme with systematic name 1,5-anhydro-D-fructose hydro-lyase (microthecin-forming). This enzyme catalyses the following chemical reaction

<span class="mw-page-title-main">Benzoxazinone biosynthesis</span>

The biosynthesis of benzoxazinone, a cyclic hydroxamate and a natural insecticide, has been well-characterized in maize and related grass species. 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. Results from wheat and rye indicate that the cluster is an ancient feature. 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. Recently, additional biosynthetic clusters have been detected in other plants for other biosynthetic pathways and this organization might be common in plants.

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

References

  1. Glawischnig E, Grün S, Frey M, Gierl A (March 1999). "Cytochrome P450 monooxygenases of DIBOA biosynthesis: specificity and conservation among grasses". Phytochemistry. 50 (6): 925–30. Bibcode:1999PChem..50..925G. doi:10.1016/s0031-9422(98)00318-5. PMID   10385992.
  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 (August 1997). "Analysis of a chemical plant defense mechanism in grasses". Science. 277 (5326): 696–9. doi:10.1126/science.277.5326.696. PMID   9235894.
  3. Spiteller P, Glawischnig E, Gierl A, Steglich W (June 2001). "Studies on the biosynthesis of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) from 3-hydroxyindolin-2-one in Zea mays". Phytochemistry. 57 (3): 373–6. Bibcode:2001PChem..57..373S. doi:10.1016/s0031-9422(01)00037-1. PMID   11393516.