204:
33:
321:
24:
422:
and the concentration decreases as the plant ages. Natural variation in the Bx1 gene influences the DIMBOA content of maize seedlings. In adult maize plants, the DIMBOA concentration is low, but it is induced rapidly in response to insect feeding. The methyltransferases Bx10, Bx11, and Bx12 convert
394:
The biosynthesis pathway from leading from maize primary metabolism to the production of DIMBOA has been fully identified. DIMBOA is stored as an inactive precursor, DIMBOA-glucoside, which is activated by glucosidases in response to insect feeding,
647:
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".
519:
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).
418:), other damaging insect pests, and pathogens, including fungi and bacteria. The exact level of DIMBOA varies between individual plants, but higher concentrations are typically found in young
334:
243:
426:
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
968:
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".
921:"Natural variation in maize aphid resistance is associated with 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside methyltransferase activity"
567:
Richter, Annett; Powell, Adrian F.; Mirzaei, Mahdieh; Wang, Lucy J.; Movahed, Navid; Miller, Julia K.; Piñeros, Miguel A.; Jander, Georg (2021).
622:
1005:"Prolonged expression of the BX1 signature enzyme is associated with a recombination hotspot in the benzoxazinoid gene cluster in Zea mays"
729:"Additive effects of two quantitative trait loci that confer Rhopalosiphum maidis (corn leaf aphid) resistance in maize inbred line Mo17"
842:
218:
105:
861:
Butrón A, Chen YC, Rottinghaus GE, McMullen MD (February 2010). "Genetic variation at bx1 controls DIMBOA content in maize".
569:"Indole‐3‐glycerolphosphate synthase, a branchpoint for the biosynthesis of tryptophan, indole, and benzoxazinoids in maize"
341:
1145:
Hu, L.; Mateo, P.; Ye, M.; Zhang, X.; Berset, J. D.; Handrick, V.; Radisch, D.; Grabe, V.; Köllner, T. G. (2018-08-17).
161:
182:
500:
Hamilton RH, Bandurski RS, Reusch WH (1962). "Isolation and characterization of a cyclic hydroxamate from Zea mays".
1218:
423:
DIMBOA into HDMBOA (2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one), which can be more toxic for insect herbivores.
1208:
473:
Niemeyer HM (1988). "Hydroxamic acids (4-hydroxy-1,4-benzoxazin-3-ones), defence chemicals in the gramineae".
451:) can detect complexes between DIMBOA and iron and use these complexes for host identification and foraging.
1213:
441:
1158:
446:
414:
45:
199:
437:
DIMBOA can also form complexes with iron in the rhizosphere and thereby enhance maize iron supply.
399:
71:
1054:"Highly localized and persistent induction of Bx1-dependent herbivore resistance factors in maize"
626:
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Ahmad S, Veyrat N, Gordon-Weeks R, Zhang Y, Martin J, Smart L, et al. (September 2011).
1052:
Maag D, Köhler A, Robert CA, Frey M, Wolfender JL, Turlings TC, et al. (December 2016).
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919:
Meihls LN, Handrick V, Glauser G, Barbier H, Kaur H, Haribal MM, et al. (June 2013).
680:"Rapid defense responses in maize leaves induced by Spodoptera exigua caterpillar feeding"
357:
125:
203:
1162:
678:
Tzin V, Hojo Y, Strickler SR, Bartsch LJ, Archer CM, Ahern KR, et al. (July 2017).
568:
1119:
1094:
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1004:
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920:
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728:
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312:
1095:"Benzoxazinoid metabolites regulate innate immunity against aphids and fungi in maize"
981:
1202:
819:
608:
486:
900:
817:
Jackson D (2009). "Vegetative Shoot
Meristems". In Bennetzen JL, Hake SC (eds.).
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32:
874:
384:
361:
297:
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DIMBOA was first identified in maize in 1962 as the "corn sweet substance".
1188:
1128:
1079:
1038:
989:
954:
936:
892:
803:
762:
713:
623:"G7113 European Corn Borer: A Multiple-Crop Pest in Missouri, MU Extension"
600:
227:
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
1110:
553:
1020:
744:
695:
431:
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356:(2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one) is a naturally occurring
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427:
137:
1070:
1053:
1003:
Zheng L, McMullen MD, Bauer E, Schön CC, Gierl A, Frey M (July 2015).
584:
311:
Except where otherwise noted, data are given for materials in their
1147:"Plant iron acquisition strategy exploited by an insect herbivore"
377:
369:
365:
104:
94:
23:
778:"Natural variation in maize defense against insect herbivores"
373:
187:
522:"Analysis of a Chemical Plant Defense Mechanism in Grasses"
329:
398:
In maize, DIMBOA functions as natural defense against
727:
Betsiashvili M, Ahern KR, Jander G (February 2015).
782:
Cold Spring Harbor
Symposia on Quantitative Biology
149:
80:
391:-like taste due to their high DIMBOA content.
8:
387:maize seedlings have a very sweet, almost
202:
124:
15:
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944:
882:
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703:
662:10.2135/cropsci1970.0011183X001000010032x
169:
360:, a benzoxazinoid. DIMBOA is a powerful
460:
434:(a fungal elicitor) and aphid feeding.
248:
223:
198:
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914:
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910:
856:
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440:Specialized insect pests such as the
230:Key: GDNZNIJPBQATCZ-UHFFFAOYSA-N
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776:Meihls LN, Kaur H, Jander G (2012).
673:
671:
468:
466:
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140:
14:
863:Theoretical and Applied Genetics
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31:
22:
315:(at 25 °C , 100 kPa).
1009:Journal of Experimental Botany
825:. Springer New York. pp.
821:Handbook of Maize: Its Biology
733:Journal of Experimental Botany
684:Journal of Experimental Botany
430:in response to treatment with
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272:
1:
982:10.1016/S0031-9422(99)00498-7
538:10.1126/science.277.5326.696
487:10.1016/0031-9422(88)80731-3
835:10.1007/978-0-387-79418-1_1
406:) larvae, beet armyworms (
251:ON(C1=CC=C(OC)C=C1OC2O)C2=O
1245:
795:10.1101/sqb.2012.77.014662
875:10.1007/s00122-009-1192-1
309:
259:
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214:
64:
50:2,4-Dihydroxy-7-methoxy-2
44:
39:
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1172:10.1126/science.aat4082
937:10.1105/tpc.113.112409
1111:10.1104/pp.111.180224
442:western corn rootworm
412:), corn leaf aphids (
447:Diabrotica virgifera
415:Rhopalosiphum maidis
46:Preferred IUPAC name
1163:2018Sci...361..694H
400:European corn borer
305: g·mol
54:-1,4-benzoxazin-3(4
18:
1021:10.1093/jxb/erv192
745:10.1093/jxb/eru379
696:10.1093/jxb/erx274
404:Ostrinia nubilalis
342:Infobox references
16:
1219:Resorcinol ethers
1157:(6403): 694–697.
1071:10.1111/tpj.13308
1058:The Plant Journal
690:(16): 4709–4723.
585:10.1111/tpj.15163
573:The Plant Journal
532:(5326): 696–699.
481:(11): 3349–3358.
409:Spodoptera exigua
350:Chemical compound
348:
347:
183:CompTox Dashboard
106:Interactive image
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1209:Hydroxamic acids
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925:The Plant Cell
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475:Phytochemistry
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653:
650:Crop Science
649:
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631:. Retrieved
627:the original
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65:Identifiers
55:
51:
884:10261/24875
364:present in
260:Properties
1203:Categories
788:: 269–83.
633:2007-11-04
508:: 107–113.
455:References
362:antibiotic
298:Molar mass
171:TI783RU0DR
117:ChemSpider
93:3D model (
82:15893-52-4
72:CAS Number
1181:0036-8075
609:231635326
593:0960-7412
546:0036-8075
449:virgifera
420:seedlings
389:saccharin
385:Etiolated
1189:30115808
1129:21730199
1080:27538820
1039:25969552
990:10680175
955:23898034
901:33310126
893:19911162
804:23223408
763:25249072
714:28981781
601:33458870
432:chitosan
1229:Lactams
1224:Lactols
1159:Bibcode
1151:Science
1120:3165881
1030:4473990
946:3723630
754:4286405
705:5853842
554:9235894
526:Science
428:callose
378:grasses
335:what is
333: (
303:211.173
138:PubChem
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354:DIMBOA
330:verify
327:
244:SMILES
40:Names
897:S2CID
829:–12.
605:S2CID
370:wheat
366:maize
219:InChI
95:JSmol
58:)-one
1185:PMID
1177:ISSN
1125:PMID
1076:PMID
1035:PMID
986:PMID
951:PMID
889:PMID
839:ISBN
800:PMID
759:PMID
710:PMID
597:PMID
589:ISSN
550:PMID
542:ISSN
162:UNII
151:2358
126:2268
1167:doi
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1115:PMC
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1103:157
1066:doi
1025:PMC
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879:hdl
871:doi
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