DIMBOA (2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one) is a benzoxazinoid (BX), is a secondary metabolite in grasses [1]. DIMBOA act as antibiotic and allelochemical, part of the chemical defense system of graminaceous plants such as maize, wheat, and rye [1,2]. 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]. Once released, BXs degrade relatively quickly in aqueous environments with a half-life of less than 24 hours [1].
DIMBOA is weak bacterial mutagens and furthermore caused aneuploidy in human-derived liver cells (HepG2 cells) [3]. DIMBOA showed genotoxic effects in HepG2 cell line [4].
DIMBOA showed the antibacterial activity against Ralstonia solanacearum with minimum inhibitory concentrations (MICs) of 50, 100 and 200 mg/L. DIMBOA also significantly affect bacterial growth, reduce biofilm formation, and inhibit swarming motility within 24 h [5].
References:
[1]. Neal A L, Ahmad S, Gordon-Weeks R, et al. Benzoxazinoids in root exudates of maize attract Pseudomonas putida to the rhizosphere[J]. PloS one, 2012, 7(4): e35498.
[2]. Gleńsk M, Gajda B, Franiczek R, et al. In vitro evaluation of the antioxidant and antimicrobial activity of DIMBOA [2, 4-dihydroxy-7-methoxy-2 H-1, 4-benzoxazin-3 (4 H)-one][J]. Natural product research, 2016, 30(11): 1305-1308.
[3]. Buchmann C A, Nersesyan A, Kopp B, et al. Dihydroxy-7-methoxy-1, 4-benzoxazin-3-one (DIMBOA) and 2, 4-dihydroxy-1, 4-benzoxazin-3-one (DIBOA), two naturally occurring benzoxazinones contained in sprouts of Gramineae are potent aneugens in human-derived liver cells (HepG2)[J]. Cancer letters, 2007, 246(1-2): 290-299.
[4]. Buchmann C, Nersesyan A, Kopp B, et al. DIMBOA and DIBOA, two naturally occuring benzoxazinoides, cause aneuploidy in a human-derived liver cell line (HepG2)[C]//BMC Pharmacology. BioMed Central, 2007, 7(2): 1-1.
[5]. Guo B, Zhang Y, Li S, et al. Extract from maize (Zea mays L.): antibacterial activity of DIMBOA and its derivatives against Ralstonia solanacearum[J]. Molecules, 2016, 21(10): 1397.