fbpx
Wikipedia

DIMBOA

February 15, 2024

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
Names
Preferred IUPAC name
2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
Identifiers
  • 15893-52-4 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 2268 N
  • 2358
UNII
  • TI783RU0DR Y
  • DTXSID90936021
  • 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 N
    Key: GDNZNIJPBQATCZ-UHFFFAOYSA-N N
  • 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).
N verify (what is YN ?)

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]

References edit

  1. ^ a b c 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. ^ . 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. ^ a b 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. ^ a b 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. ^ a b c 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. ^ a b 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.

February 15, 2024
dimboa, dihydroxy, methoxy, benzoxazin, naturally, occurring, hydroxamic, acid, benzoxazinoid, powerful, antibiotic, present, maize, wheat, related, grasses, namespreferred, iupac, name, dihydroxy, methoxy, benzoxazin, oneidentifierscas, number, 15893, model, . 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 NamesPreferred IUPAC name 2 4 Dihydroxy 7 methoxy 2H 1 4 benzoxazin 3 4H oneIdentifiersCAS Number 15893 52 4 Y3D model JSmol Interactive imageChemSpider 2268 NPubChem CID 2358UNII TI783RU0DR YCompTox Dashboard EPA DTXSID90936021InChI 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 NKey GDNZNIJPBQATCZ UHFFFAOYSA N NSMILES ON C1 CC C OC C C1OC2O C2 OPropertiesChemical formula C 9H 9N O 5Molar mass 211 173 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references 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 References edit a b c 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 Hamilton RH Bandurski RS Reusch WH 1962 Isolation and characterization of a cyclic hydroxamate from Zea mays Cereal Chemistry 39 107 113 Frey Monika Chomet Paul Glawischnig Erich Stettner Cornelia Grun 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 Richter Annett Powell Adrian F Mirzaei Mahdieh Wang Lucy J Movahed Navid Miller Julia K Pineros 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 G7113 European Corn Borer A Multiple Crop Pest in Missouri MU Extension Archived from the original on 2009 01 16 Retrieved 2007 11 04 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 a b 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 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 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 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 a b Butron 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 a b c 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 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 Zheng L McMullen MD Bauer E Schon 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 Maag D Kohler 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 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 a b Hu L Mateo P Ye M Zhang X Berset J D Handrick V Radisch D Grabe V Kollner 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 Retrieved from https en wikipedia org w index php title DIMBOA amp oldid 1193452700, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.