DIMBOA

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DIMBOA
DIMBOA.png
DIMBOA-ballstick.png
Names
Preferred IUPAC name
2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C9H9NO5/c1-14-5-2-3-6-7(4-5)15-9(12)8(11)10(6)13/h2-4,9,12-13H,1H3 X mark.svgN
    Key: GDNZNIJPBQATCZ-UHFFFAOYSA-N X mark.svgN
  • ON(C1=CC=C(OC)C=C1OC2O)C2=O
Properties
C9H9NO5
Molar mass 211.173 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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, [1]

DIMBOA was first identified in maize in 1962 as the "corn sweet substance". [2] Etiolated maize seedlings have a very sweet, almost saccharin-like taste due to their high DIMBOA content.

The biosynthesis pathway from leading from maize primary metabolism to the production of DIMBOA has been fully identified. [3] [4] DIMBOA is stored as an inactive precursor, DIMBOA-glucoside, which is activated by glucosidases in response to insect feeding, [1]

In maize, DIMBOA functions as natural defense against European corn borer (Ostrinia nubilalis) larvae, [5] [6] beet armyworms ( Spodoptera exigua ), [7] corn leaf aphids ( Rhopalosiphum maidis ), [8] other damaging insect pests, and pathogens, including fungi and bacteria. [1] [9] [10] The exact level of DIMBOA varies between individual plants, [11] [12] but higher concentrations are typically found in young seedlings and the concentration decreases as the plant ages. [13] Natural variation in the Bx1 gene influences the DIMBOA content of maize seedlings. [11] [14] In adult maize plants, the DIMBOA concentration is low, but it is induced rapidly in response to insect feeding. [15] The methyltransferases Bx10, Bx11, and Bx12 convert DIMBOA into HDMBOA (2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one), which can be more toxic for insect herbivores. [12] [7]

In addition to serving as a direct defensive compound due to its toxicity, DIMBOA can also function as a signaling molecule, leading to the accumulation of callose in response to treatment with chitosan (a fungal elicitor) and aphid feeding. [12] [16]

DIMBOA can also form complexes with iron in the rhizosphere and thereby enhance maize iron supply. [17]

Specialized insect pests such as the western corn rootworm ( Diabrotica virgifera virgifera) can detect complexes between DIMBOA and iron and use these complexes for host identification and foraging. [17]

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<span class="mw-page-title-main">Western corn rootworm</span> Subspecies of beetle

The Western corn rootworm, Diabrotica virgifera virgifera, is one of the most devastating corn rootworm species in North America, especially in the midwestern corn-growing areas such as Iowa. A related species, the Northern corn rootworm, D. barberi, co-inhabits in much of the range and is fairly similar in biology.

<span class="mw-page-title-main">Plant defense against herbivory</span> Plants defenses against being eaten

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<i>Maize dwarf mosaic virus</i> Species of plant pathogenic virus

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

<span class="mw-page-title-main">Maize</span> Genus of grass cultivated as a food crop

Maize ; Zea mays subsp. mays, also known as corn in North American and Australian English, is a cereal grain first domesticated by indigenous peoples in southern Mexico about 10,000 years ago. The leafy stalk of the plant gives rise to inflorescences which produce pollen and separate ovuliferous inflorescences called ears that when fertilized yield kernels or seeds, which are botanical fruits. The term maize is preferred in formal, scientific, and international usage as the common name because it refers specifically to this one grain whereas corn refers to any principal cereal crop cultivated in a country. For example, in North America and Australia corn is often used for maize, but in England and Wales it can refer to wheat or barley, and in Scotland and Ireland to oats.

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<i>Rhopalosiphum maidis</i> Species of true bug

Rhopalosiphum maidis, common names corn leaf aphid and corn aphid, is an insect, and a pest of maize and other crops. It has a nearly worldwide distribution and is typically found in agricultural fields, grasslands, and forest-grassland zones. Among aphids that feed on maize, it is the most commonly encountered and most economically damaging, particularly in tropical and warmer temperate areas. In addition to maize, R. maidis damages rice, sorghum, and other cultivated and wild monocots.

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

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

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

<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.

<span class="mw-page-title-main">Tritrophic interactions in plant defense</span> Ecological interactions

Tritrophic interactions in plant defense against herbivory describe the ecological impacts of three trophic levels on each other: the plant, the herbivore, and its natural enemies. They may also be called multitrophic interactions when further trophic levels, such as soil microbes, endophytes, or hyperparasitoids are considered. Tritrophic interactions join pollination and seed dispersal as vital biological functions which plants perform via cooperation with animals.

<span class="mw-page-title-main">Georg Jander</span> American plant biologist

Georg Jander is an American plant biologist at the Boyce Thompson Institute in Ithaca, New York. He has an adjunct appointment in the Plant Biology Section of the School of Integrative Plant Sciences at Cornell University. Jander is known for his molecular research identifying genes for biochemical compounds of ecological and agricultural importance, particularly those plant traits involved in resistance to insect pests.

References

  1. 1 2 3 Niemeyer HM (1988). "Hydroxamic acids (4-hydroxy-1,4-benzoxazin-3-ones), defence chemicals in the gramineae". Phytochemistry. 27 (11): 3349–3358. doi:10.1016/0031-9422(88)80731-3.
  2. ↑ Hamilton RH, Bandurski RS, Reusch WH (1962). "Isolation and characterization of a cyclic hydroxamate from Zea mays". Cereal Chemistry. 39: 107–113.
  3. ↑ Frey, Monika; Chomet, Paul; Glawischnig, Erich; Stettner, Cornelia; Grün, Sebastian; Winklmair, Albert; Eisenreich, Wolfgang; Bacher, Adelbert; Meeley, Robert B.; Briggs, Steven P.; Simcox, Kevin; Gierl, Alfons (1997). "Analysis of a Chemical Plant Defense Mechanism in Grasses". Science. 277 (5326): 696–699. doi:10.1126/science.277.5326.696. ISSN   0036-8075. PMID   9235894.
  4. ↑ Richter, Annett; Powell, Adrian F.; Mirzaei, Mahdieh; Wang, Lucy J.; Movahed, Navid; Miller, Julia K.; Piñeros, Miguel A.; Jander, Georg (2021). "Indole‐3‐glycerolphosphate synthase, a branchpoint for the biosynthesis of tryptophan, indole, and benzoxazinoids in maize". The Plant Journal. 106 (1): 245–257. doi:10.1111/tpj.15163. ISSN   0960-7412. PMID   33458870. S2CID   231635326.
  5. ↑ "G7113 European Corn Borer: A Multiple-Crop Pest in Missouri, MU Extension". Archived from the original on 2009-01-16. Retrieved 2007-11-04.
  6. ↑ Klun JA, Guthrie WD, Hallauer AR, Russell WA (1970). "Genetic Nature of the Concentration of 2,4-dihydroxy-7-methoxy 2H-l,4-benzoxazin- 3(4H)-one and Resistance to the European Corn Borer in a Diallel Set of Eleven Maize Inbreds1". Crop Science. 10 (1): 87–90. doi:10.2135/cropsci1970.0011183X001000010032x.
  7. 1 2 Tzin V, Hojo Y, Strickler SR, Bartsch LJ, Archer CM, Ahern KR, et al. (July 2017). "Rapid defense responses in maize leaves induced by Spodoptera exigua caterpillar feeding". Journal of Experimental Botany. 68 (16): 4709–4723. doi:10.1093/jxb/erx274. PMC   5853842 . PMID   28981781.
  8. ↑ Betsiashvili M, Ahern KR, Jander G (February 2015). "Additive effects of two quantitative trait loci that confer Rhopalosiphum maidis (corn leaf aphid) resistance in maize inbred line Mo17". Journal of Experimental Botany. 66 (2): 571–8. doi:10.1093/jxb/eru379. PMC   4286405 . PMID   25249072.
  9. ↑ Meihls LN, Kaur H, Jander G (2012). "Natural variation in maize defense against insect herbivores". Cold Spring Harbor Symposia on Quantitative Biology. 77: 269–83. doi: 10.1101/sqb.2012.77.014662 . PMID   23223408.
  10. ↑ Jackson D (2009). "Vegetative Shoot Meristems". In Bennetzen JL, Hake SC (eds.). Handbook of Maize: Its Biology . Springer New York. pp.  1–12. doi:10.1007/978-0-387-79418-1_1. ISBN   9780387794174.
  11. 1 2 Butrón A, Chen YC, Rottinghaus GE, McMullen MD (February 2010). "Genetic variation at bx1 controls DIMBOA content in maize". Theoretical and Applied Genetics. 120 (4): 721–34. doi:10.1007/s00122-009-1192-1. hdl: 10261/24875 . PMID   19911162. S2CID   33310126.
  12. 1 2 3 Meihls LN, Handrick V, Glauser G, Barbier H, Kaur H, Haribal MM, et al. (June 2013). "Natural variation in maize aphid resistance is associated with 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside methyltransferase activity". The Plant Cell. 25 (6): 2341–55. doi:10.1105/tpc.113.112409. PMC   3723630 . PMID   23898034.
  13. ↑ Cambier V, Hance T, de Hoffmann E (January 2000). "Variation of DIMBOA and related compounds content in relation to the age and plant organ in maize". Phytochemistry. 53 (2): 223–9. doi:10.1016/S0031-9422(99)00498-7. PMID   10680175.
  14. ↑ Zheng L, McMullen MD, Bauer E, Schön CC, Gierl A, Frey M (July 2015). "Prolonged expression of the BX1 signature enzyme is associated with a recombination hotspot in the benzoxazinoid gene cluster in Zea mays". Journal of Experimental Botany. 66 (13): 3917–30. doi:10.1093/jxb/erv192. PMC   4473990 . PMID   25969552.
  15. ↑ Maag D, Köhler A, Robert CA, Frey M, Wolfender JL, Turlings TC, et al. (December 2016). "Highly localized and persistent induction of Bx1-dependent herbivore resistance factors in maize". The Plant Journal. 88 (6): 976–991. doi: 10.1111/tpj.13308 . PMID   27538820.
  16. ↑ Ahmad S, Veyrat N, Gordon-Weeks R, Zhang Y, Martin J, Smart L, et al. (September 2011). "Benzoxazinoid metabolites regulate innate immunity against aphids and fungi in maize". Plant Physiology. 157 (1): 317–27. doi:10.1104/pp.111.180224. PMC   3165881 . PMID   21730199.
  17. 1 2 Hu, L.; Mateo, P.; Ye, M.; Zhang, X.; Berset, J. D.; Handrick, V.; Radisch, D.; Grabe, V.; Köllner, T. G. (2018-08-17). "Plant iron acquisition strategy exploited by an insect herbivore". Science. 361 (6403): 694–697. Bibcode:2018Sci...361..694H. doi: 10.1126/science.aat4082 . ISSN   0036-8075. PMID   30115808.
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