15893-52-4
Chemical Structure
DIMBOA
- CAS No.: 15893-52-4
- Formula:C9H9NO5
- Molecular Weight:211.17
IUPAC Name: 2,4-dihydroxy-7-methoxy-2H-benzo[b][1,4]oxazin-3(4H)-one
InChIKey: GDNZNIJPBQATCZ-UHFFFAOYSA-N
SMILES: O=C1C(O)OC2=CC(OC)=CC=C2N1O
Biological Activity: DIMBOA, an antibiotic, has antibacterial properties and inhibits bacteria such as Staphylococcus aureus and the mycotoxin-producing fungus Fusarium graminearum (which causes scab). DIMBOA exhibits strong free radical scavenging activity and weak iron(III) ion reducing activity, and has antioxidant activity. DIMBOA inhibits the biosynthesis and accumulation of toxic trichothecenes by affecting the expression of Tri6 and Tri5. DIMBOA reduces plant susceptibility to scab. DIMBOA also exhibits cytotoxicity to plant cells, causing plasmolysis, cell collapse, and cell rupture[1][2][3][4][5].
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DIMBOA | 99.81% | DIMBOA, an antibiotic, has antibacterial properties and inhibits bacteria such as Staphylococcus aureus and the mycotoxin-producing fungus Fusarium graminearum (which causes scab). DIMBOA exhibits strong free radical scavenging activity and weak iron(III) ion reducing activity, and has antioxidant activity. DIMBOA inhibits the biosynthesis and accumulation of toxic trichothecenes by affecting the expression of Tri6 and Tri5. DIMBOA reduces plant susceptibility to scab. DIMBOA also exhibits cytotoxicity to plant cells, causing plasmolysis, cell collapse, and cell rupture. | ||||||||||||||||||||
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DIMBOA (Standard) | 97.12% | DIMBOA (Standard) is the analytical standard of DIMBOA. This product is intended for research and analytical applications. DIMBOA, an antibiotic, has antibacterial properties and inhibits bacteria such as Staphylococcus aureus and the mycotoxin-producing fungus Fusarium graminearum (which causes scab). DIMBOA exhibits strong free radical scavenging activity and weak iron(III) ion reducing activity, and has antioxidant activity. DIMBOA inhibits the biosynthesis and accumulation of toxic trichothecenes by affecting the expression of Tri6 and Tri5. DIMBOA reduces plant susceptibility to scab. DIMBOA also exhibits cytotoxicity to plant cells, causing plasmolysis, cell collapse, and cell rupture. | ||||||||||||||||||||
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- [1]. Phuong, T.T.T., Yamamoto, M., Fujii, T. et al. Comparison of the ability to catabolize DIMBOA, a maize antibiotic, between Ostrinia furnacalis and Ostrinia scapulalis(Lepidoptera: Crambidae), with reference to their hybrids. Appl Entomol Zool 51, 143–149 (2016).
- [2]. Gleńsk M, et al. In vitro evaluation of the antioxidant and antimicrobial activity of DIMBOA [2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one]. Nat Prod Res. 2016;30(11):1305-1308. [Content Brief]
- [3]. Sasai H, et al. Species-specific glucosylation of DIMBOA in larvae of the rice Armyworm. Biosci Biotechnol Biochem. 2009;73(6):1333-1338. [Content Brief]
- [4]. Etzerodt T, et al. 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA) inhibits trichothecene production by Fusarium graminearum through suppression of Tri6 expression. Int J Food Microbiol. 2015 Dec 2;214:123-128. [Content Brief]
- [5]. Sahi S V, et al. The corn wound metabolite DIMBOA causes cell death in tobacco and corn[J]. Plant Science, 1995, 108(1): 31-40.
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