DIMBOA, is a novel and potent antibiotic and benzoxazinoid, it is a part of the chemical defense system of graminaceous plants .
Physicochemical Properties
| Molecular Formula | C9H9NO5 |
| Molecular Weight | 211.1715 |
| Exact Mass | 211.048 |
| Elemental Analysis | C, 51.19; H, 4.30; N, 6.63; O, 37.88 |
| CAS # | 15893-52-4 |
| Related CAS # | 15893-52-4; |
| PubChem CID | 2358 |
| Appearance | Light brown to brown solid powder |
| Density | 1.589g/cm3 |
| Boiling Point | 461.3ºC at 760mmHg |
| Melting Point | 150-155 °C |
| Flash Point | 232.8ºC |
| Vapour Pressure | 2.64E-09mmHg at 25°C |
| Index of Refraction | 1.658 |
| LogP | 0.193 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 1 |
| Heavy Atom Count | 15 |
| Complexity | 259 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O1C([H])(C(N(C2C([H])=C([H])C(=C([H])C1=2)OC([H])([H])[H])O[H])=O)O[H] |
| InChi Key | GDNZNIJPBQATCZ-UHFFFAOYSA-N |
| InChi Code | 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 |
| Chemical Name | 2,4-dihydroxy-7-methoxy-2H-benzo[b][1,4]oxazin-3(4H)-one |
| Synonyms | DIMBOA |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro |
In vitro, DIMBOA was rapidly catabolized when incubated with the homogenate of the digestive tract of O. furnacalis in the presence of uridine diphosphate (UDP)-glucose. The UDP-glucose-dependent DIMBOA-catabolizing activities of the homogenate of the digestive tracts of O. scapulalis and hybrids correlated with their tolerance; low in O. scapulalis and high in the hybrids. These results reconfirmed that UDP-glucosyltransferase (UGT) or other UDP-dependent enzymes are involved in the catabolism of DIMBOA in O. furnacalis; however, consistent with our previous findings, DIMBOA-glucoside, the expected product of UGT, was not detected in the products of in vitro assays.[1] Antioxidant activity of the isolated DIMBOA was examined using DPPH, FRAP and ABTS tests. It was found that DIMBOA exhibits a potent free-radical scavenging activity and a weaker iron (III) ions reducing activity. Antimicrobial activity against selected G(+), G(-) bacterial strains and against yeasts-like reference strains of fungi was investigated using disk-diffusion method. It has been shown that DIMBOA possess growth inhibitory properties against many strains of studied bacteria and fungi, such as Staphylococcus aureus, Escherichia coli as well as against Saccharomyces cerevisiae.[2] We tested 7 major secondary metabolites from wheat for their effect on trichothecene production in liquid cultures of F. graminearum producing trichothecene 15-acetyldeoxynivalenol (15-ADON). 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA) benzoxazinoid completely abolished toxin production without any apparent effect on fungal growth. DIMBOA strongly affected the expression of Tri6, encoding a major transcriptional regulator of several genes of the trichothecene biosynthesis pathway. DIMBOA also repressed expression of Tri5, encoding trichodiene synthase, the first enzyme in the trichothecene biosynthesis pathway. Thus, DIMBOA could play an important role against the accumulation of trichothecenes in wheat grain. Breeding or engineering of wheat with increased levels of benzoxazinoids could provide varieties with increased resistance against trichothecene contamination of grain and lower susceptibility to FHB.[4] DIMBOA (2,4-dihydroxy-7-methoxy-1,4(2H)-benzoxazin-3-one), a corn (maize) secondary metabolite, is lethal to the cells of tobacco, carrot root slices and to both DIMBOA-producing (B73) and non-producing (bxbx) varieties of corn. Application of DIMBOA to wounded tobacco leaf petioles causes a black lesion and shrivelling of the whole leaf, presumably resulting from death of DIMBOA-treated cells and subsequently uneven growth of the leaf blade. Microscopic examination reveals that DIMBOA treatment causes plasmolysis, cell collapse and disruption of cells. DIMBOA also causes browning and necrosis in the leaf-spot assay on tobacco and on high- and low-DIMBOA varieties of corn. MBOA, a degradation product of DIMBOA, does not cause significant damage to the corn leaf.[5] |
| ln Vivo | Maize contains 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), which functions as a feeding deterrent, growth inhibitor, and toxin against many herbivorous insects. In laboratory assays, the addition of 0.3 mg/g of DIMBOA to an artificial diet markedly affected the survival of O. scapulalis larvae but not that of O. furnacalis larvae. Hybrids of O. furnacalis and O. scapulalis, crossed in both directions, tolerated DIMBOA to the same extent as O. furnacalis, indicating that this tolerance was conferred by a single or a few autosomal genes that are dominant to those of O. scapulalis.[1] |
| References |
[1]. 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]. 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. [3]. Species-specific glucosylation of DIMBOA in larvae of the rice Armyworm. Biosci Biotechnol Biochem. 2009;73(6):1333-1338. [4]. 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. [5]. The corn wound metabolite DIMBOA causes cell death in tobacco and corn. Plant Science, 1995, 108(1): 31-40. |
| Additional Infomation |
DIMBOA is a lactol that is DIBOA in which the hydrogen at position 7 is replaced by a methoxy group. It has been isolated from the maize plants. It has a role as a plant metabolite and an allelochemical. It is a lactol, a benzoxazine, an aromatic ether and a cyclic hydroxamic acid. It is functionally related to a DIBOA. 2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one has been reported in Trichoderma virens with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~50 mg/mL (~236.78 mM ) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (11.84 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (9.85 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 3: 10% DMSO+90% (20% SBE-β-CD in Saline)2.5 mg/mL (11.84 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.7355 mL | 23.6776 mL | 47.3552 mL | |
| 5 mM | 0.9471 mL | 4.7355 mL | 9.4710 mL | |
| 10 mM | 0.4736 mL | 2.3678 mL | 4.7355 mL |