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DIMBOA Sale

(Synonyms: 丁布) 目录号 : GC60138

DIMBOA(2,4-二羟基-7-甲氧基- 2h -1,4-苯并恶嗪-3(4H)- 1)是一种苯并恶嗪类化合物(BX),是禾本科植物的次生代谢物。

DIMBOA Chemical Structure

Cas No.:15893-52-4

规格 价格 库存 购买数量
10mM (in 1mL DMSO)
¥618.00
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1mg
¥235.00
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5mg
¥534.00
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10mg
¥896.00
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25mg
¥1,792.00
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50mg
¥2,867.00
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100mg
¥4,488.00
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Sample solution is provided at 25 µL, 10mM.

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Description

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.

实验参考方法

Cell experiment [1]:

Cell lines

Pseudomonas putida KT2440

Preparation Method

P. putida KT2440 cells were grown to mid-exponential phase in 100 mL M9 medium before DIMBOA was added to a final concentration of 5 µg mL-1. After 1 hour of exposure, cells were harvested by centrifugation at 4°C.

Reaction Conditions

5 µg mL-1, 1h

Applications

P. putida KT2440 appears relatively tolerant to DIMBOA in comparison to other soil bacteria. For all subsequent experiments, DIMBOA was employed at concentrations of 5 µg mL-1 (0.023 mM).

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.

化学性质

Cas No. 15893-52-4 SDF
别名 丁布
Canonical SMILES O=C1C(O)OC2=CC(OC)=CC=C2N1O
分子式 C9H9NO5 分子量 211.17
溶解度 DMSO: 125 mg/mL (591.94 mM) 储存条件 Store at -20°C
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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 9.471 mL
10 mM 0.4736 mL 2.3678 mL 4.7355 mL
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