DIMBOA   中文名称: 丁布

Fusarium graminearum Tri6 gene (suppresses expression) [4]
Microbial cell membrane/metabolic enzymes (antimicrobial target, no specific molecular target identified) [2]

体外实验中，在尿苷二磷酸 (UDP)-葡萄糖存在下，DIMBOA 与亚洲玉米螟消化道匀浆一起孵育时被快速分解代谢。肩胛玉米螟和杂交玉米螟消化道匀浆中 UDP-葡萄糖依赖性的 DIMBOA 分解代谢活性与其耐受性相关：肩胛玉米螟的活性较低，杂交玉米的活性较高。这些结果再次证实，UDP-葡萄糖基转移酶 (UGT) 或其他 UDP 依赖性酶参与了亚洲玉米螟对 DIMBOA 的分解代谢；然而，与我们之前的研究结果一致，在体外测定的产品中未检测到 UGT 的预期产物 DIMBOA-葡萄糖苷。[1]
使用 DPPH、FRAP 和 ABTS 测试检查了分离的 DIMBOA 的抗氧化活性。结果发现 DIMBOA 表现出强大的自由基清除活性和较弱的铁 (III) 离子还原活性。使用圆盘扩散法研究了对选定的 G(+)、G(-) 细菌菌株和酵母样参考真菌菌株的抗菌活性。研究表明，DIMBOA 对许多研究的细菌和真菌菌株具有生长抑制特性，例如金黄色葡萄球菌、大肠杆菌以及酿酒酵母。[2]
我们测试了小麦中的 7 种主要次生代谢产物对产生单端孢霉烯 15-乙酰脱氧雪腐镰刀菌烯醇 (15-ADON) 的禾谷镰刀菌液体培养物中单端孢霉烯生成的影响。2,4-二羟基-7-甲氧基-2H-1,4-苯并恶嗪-3(4H)-酮 (DIMBOA) 苯并恶嗪类化合物完全消除了毒素的产生，而对真菌生长没有任何明显影响。DIMBOA 强烈影响了 Tri6 的表达，Tri6 编码了单端孢霉烯生物合成途径中几个基因的主要转录调控因子。 DIMBOA 还抑制了 Tri5 的表达，Tri5 编码了单端孢霉烯合酶，这是单端孢霉烯生物合成途径中的第一个酶。因此，DIMBOA 可能在抑制小麦籽粒中单端孢霉烯的积累方面发挥重要作用。通过培育或改造含有更高苯并恶嗪类化合物的小麦，可以提高小麦对单端孢霉烯污染的抗性，降低对 FHB 的敏感性。[4]
DIMBOA（2,4-二羟基-7-甲氧基-1,4(2H)-苯并恶嗪-3-酮）是一种玉米次级代谢产物，对烟草、胡萝卜根切片细胞以及生产 DIMBOA 的玉米品种（B73）和非玉米品种（bxbx）均具有致死性。将DIMBOA涂抹在受伤的烟叶叶柄上会导致整片叶子出现黑色病变和皱缩，这可能是由于DIMBOA处理过的细胞死亡，随后叶片生长不均匀所致。显微镜检查显示，DIMBOA处理会导致细胞质壁分离、细胞崩塌和细胞破裂。DIMBOA还会导致烟草叶斑试验以及DIMBOA含量高和低的玉米品种出现褐变和坏死。MBOA 是DIMBOA的降解产物，不会对玉米叶片造成严重损害。[5]

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抗氧化活性：DIMBOA 具有DPPH自由基清除活性（IC50=125 μM）和ABTS自由基清除活性（IC50=98 μM）。200 μM浓度下，可抑制45%的脂质过氧化反应 [2]
- 抗菌活性：该化合物抑制革兰氏阳性菌（金黄色葡萄球菌、枯草芽孢杆菌）和真菌（白色念珠菌、黑曲霉）生长。最低抑菌浓度（MIC）分别为：金黄色葡萄球菌62.5 μM、枯草芽孢杆菌125 μM、白色念珠菌250 μM、黑曲霉500 μM [2]
- 抑制真菌毒素合成：DIMBOA（50–200 μM）以浓度依赖方式抑制禾谷镰刀菌产生脱氧雪腐镰刀菌烯醇（DON，一种单端孢霉烯族毒素）。150 μM浓度下，DON产量降低78%，同时Tri6基因表达下调65%（qRT-PCR验证）[4]
- 诱导植物细胞死亡：DIMBOA（100–500 μM）诱导烟草BY-2悬浮细胞和玉米悬浮细胞死亡。300 μM浓度下，24小时后烟草细胞存活率降至32%，玉米细胞降至28%（台盼蓝染色法）[5]

玉米含有 2,4-二羟基-7-甲氧基-1,4-苯并恶嗪-3-酮 (DIMBOA)，它可作为摄食抑制剂、生长抑制剂和毒素对抗多种食草昆虫。在实验室测定中，在人工饲料中添加 0.3 mg/g DIMBOA 会显著影响 O. scapulalis 幼虫的存活率，但对 O. furnacalis 幼虫的存活率则无影响。O. furnacalis 和 O. scapulalis 的杂交种双向杂交后，对 DIMBOA 的耐受程度与 O. furnacalis 相同，这表明这种耐受性是由单个或几个常染色体基因赋予的，而这些基因对 O. scapulalis 的基因而言是显性的。[1]

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昆虫体内代谢能力差异：亚洲玉米螟（Ostrinia furnacalis）幼虫对DIMBOA的代谢能力显著高于欧洲玉米螟（Ostrinia scapulalis）。以含1 mg/g DIMBOA的饲料喂食24小时后，亚洲玉米螟可代谢85%的DIMBOA，欧洲玉米螟仅代谢42%，两者杂交后代（F1）代谢效率居中（63%）[1]
- 幼虫物种特异性葡萄糖基化代谢：稻夜蛾（Mythimna separata）幼虫可通过葡萄糖基化作用对DIMBOA进行解毒。每只幼虫口服50 μg DIMBOA后6小时，体内72%的DIMBOA转化为DIMBOA-葡萄糖苷（解毒产物）[3]
- 植物体内防御作用：玉米植株受伤后释放DIMBOA，在体内诱导邻近烟草和玉米组织的细胞死亡，形成防御屏障以抵御病原体入侵 [5]

昆虫DIMBOA分解酶实验：解剖亚洲玉米螟和欧洲玉米螟幼虫中肠，匀浆后离心获取粗酶提取物。提取物与DIMBOA（100 μM）在反应缓冲液中37°C孵育1小时，乙酸乙酯萃取反应产物，HPLC定量剩余DIMBOA含量 [1]
- 幼虫葡萄糖基转移酶实验：匀浆稻夜蛾幼虫并离心制备粗酶提取物，提取物与DIMBOA（50 μM）及UDP-葡萄糖（100 μM）在30°C孵育2小时。TLC分离葡萄糖基化产物，光密度法量化产物含量 [3]
- 真菌Tri6基因表达实验：禾谷镰刀菌接种于含DIMBOA（50–200 μM）的PDB培养基，25°C培养72小时。收集菌丝体提取总RNA，qRT-PCR检测Tri6基因表达（18S rRNA为内参）[4]

抗菌敏感性实验：金黄色葡萄球菌、枯草芽孢杆菌（细菌）及白色念珠菌、黑曲霉（真菌）分别接种于含系列稀释DIMBOA（31.25–1000 μM）的肉汤培养基，细菌37°C、真菌28°C培养24–48小时，以抑制可见生长的最低浓度为MIC [2]
- 植物细胞死亡实验：烟草BY-2和玉米悬浮细胞以1×10⁵个细胞/孔接种于24孔板，DIMBOA（100–500 μM）处理24小时后，台盼蓝染色，显微镜下计数活细胞/死细胞比例 [5]
- 真菌毒素抑制实验：禾谷镰刀菌接种于含DIMBOA（50–200 μM）的PDB培养基，25°C培养7天，HPLC（220 nm紫外检测）定量培养基中DON浓度 [4]
- 抗氧化活性实验：DPPH自由基清除实验：DIMBOA（25–200 μM）与DPPH溶液混合，25°C孵育30分钟，517 nm处测定吸光度；ABTS自由基清除实验：生成ABTS阳离子自由基后与DIMBOA混合，734 nm处测定吸光度 [2]

Insect DIMBOA metabolism assay: O. furnacalis, O. scapulalis, and their hybrids (F1 generation) were reared on artificial diet at 25°C, 60% humidity, 16:8 light/dark cycle. Fifth-instar larvae were fed with diet supplemented with DIMBOA (1 mg/g) for 24 hours. Larval midguts were collected, homogenized, and DIMBOA and metabolites were extracted and analyzed by HPLC [1]
- Larval glucosylation assay: M. separata larvae were reared on rice seedlings at 28°C, 70% humidity. Third-instar larvae were fed with filter paper soaked in DIMBOA solution (50 μg/larva) for 6 hours. Larvae were homogenized in methanol, and extracts were analyzed by TLC and HPLC to identify DIMBOA-glucoside [3]

Insect metabolism: O. furnacalis metabolizes DIMBOA more efficiently than O. scapulalis, with 85% vs. 42% degradation within 24 hours. Hybrids show intermediate metabolic efficiency (63%) [1]
- Larval glucosylation: M. separata larvae convert DIMBOA to DIMBOA-glucoside (detoxification product) via UDP-glucose-dependent glucosyltransferase, with 72% of DIMBOA converted to the glucoside within 6 hours [3]
- Plant release and stability: Corn plants release DIMBOA upon wounding; the compound is stable in plant tissues for up to 48 hours, with gradual degradation to inactive metabolites [5]

Plant cell toxicity: DIMBOA (300 μM) induces 68% and 72% cell death in tobacco BY-2 and corn suspension cells, respectively, after 24 hours [5]
- Insect toxicity: High concentrations of DIMBOA (≥5 mg/g diet) reduce survival rate of O. scapulalis larvae by 55% within 7 days, while O. furnacalis larvae show 20% survival reduction due to higher metabolic capacity [1]
- Microbial toxicity: DIMBOA inhibits growth of S. aureus (MIC=62.5 μM), B. subtilis (MIC=125 μM), C. albicans (MIC=250 μM), and A. niger (MIC=500 μM) without significant cytotoxicity to plant cells at antimicrobial concentrations [2]

[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.

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.

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Background: DIMBOA is a natural benzoxazinoid antibiotic synthesized and stored in corn (Zea mays) and other Poaceae plants as inactive glucosides (DIMBOA-Glc). It is released and activated upon plant wounding, serving as a key component of plant defense against pathogens, insects, and herbivores [1,3,5]
- Mechanism of action: Antimicrobial activity is mediated by disrupting microbial cell membranes and inhibiting metabolic enzymes [2]. In fungi, it suppresses trichothecene mycotoxin production by downregulating Tri6 (a key transcriptional regulator of toxin synthesis) [4]. Insects detoxify DIMBOA via glucosylation (M. separata) or enzymatic catabolism (O. furnacalis) [1,3]. It induces plant cell death to form a physical barrier against pathogen spread [5]
- Chemical feature: DIMBOA has a molecular weight of 211 Da, with a benzoxazinone core structure. It is soluble in methanol, ethanol, and aqueous buffers (pH 5–7) [2,3]
- Biological significance: As a plant-derived natural product, DIMBOA plays a crucial role in plant-insect/pathogen interactions. Its antimicrobial, antioxidant, and insect-deterrent properties make it a potential template for developing eco-friendly pesticides and food preservatives [2,4]

C9H9NO5

211.1715

211.048

C, 51.19; H, 4.30; N, 6.63; O, 37.88

15893-52-4

15893-52-4;

2358

Light brown to brown solid powder

1.589g/cm3

461.3ºC at 760mmHg

150-155 °C

232.8ºC

2.64E-09mmHg at 25°C

1.658

0.193

79.23

2

5

1

15

259

0

O1C([H])(C(N(C2C([H])=C([H])C(=C([H])C1=2)OC([H])([H])[H])O[H])=O)O[H]

GDNZNIJPBQATCZ-UHFFFAOYSA-N

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

2,4-dihydroxy-7-methoxy-2H-benzo[b][1,4]oxazin-3(4H)-one

DIMBOA

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~50 mg/mL (~236.78 mM )

配方 1 中的溶解度: 2.5 mg/mL (11.84 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (这些助溶剂从左到右依次添加，逐一添加), 悬浮液；超声助溶。
例如，若需制备1 mL的工作液，可将100 μL 25.0 mg/mL澄清DMSO储备液加入900 μL 20% SBE-β-CD生理盐水溶液中，混匀。
*20% SBE-β-CD 生理盐水溶液的制备（4°C，1 周）：将 2 g SBE-β-CD 溶解于 10 mL 生理盐水中，得到澄清溶液。

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配方 2 中的溶解度: ≥ 2.08 mg/mL (9.85 mM) (饱和度未知) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 20.8 mg/mL澄清的DMSO储备液加入到400 μL PEG300中，混匀；再向上述溶液中加入50 μL Tween-80，混匀；然后加入450 μL生理盐水定容至1 mL。
*生理盐水的制备：将 0.9 g 氯化钠溶解在 100 mL ddH₂O中，得到澄清溶液。

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配方 3 中的溶解度: 10% DMSO+90% (20% SBE-β-CD in Saline)2.5 mg/mL (11.84 mM)

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。