2-Hydroxyemodin
(Synonyms: 2-羟基大黄素) 目录号 : GC64336
2-Hydroxyemodin 是肝微粒体中大黄素的活性代谢物。大黄素是一种存在于真菌代谢物和大黄成分中的蒽醌。在没有激活系统的情况下，2-Hydroxyemodin 对鼠伤寒沙门氏菌 TA1537 具有诱变作用。
Cas No.:641-90-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2-Hydroxyemodin is an active metabolite of emodin in the hepatic microsomes. Emodin is an anthraquinone present in fungal metabolites and constituent of rhubarb. 2-Hydroxyemodin proves to be mutagenic to Salmonella typhimurium TA1537 in the absence of activation system[1].
[1]. Masuda T, et al. 2-Hydroxyemodin, an active metabolite of emodin in the hepatic microsomes of rats. Mutat Res. 1985;149(3):327-332.
| Cas No. | 641-90-7 | SDF | Download SDF |
| 别名 | 2-羟基大黄素 | ||
| 分子式 | C15H10O6 | 分子量 | 286.24 |
| 溶解度 | 储存条件 | 4°C, away from moisture and light | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.4936 mL | 17.4679 mL | 34.9357 mL |
| 5 mM | 0.6987 mL | 3.4936 mL | 6.9871 mL |
| 10 mM | 0.3494 mL | 1.7468 mL | 3.4936 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
2-Hydroxyemodin, an active metabolite of emodin in the hepatic microsomes of rats
Mutat Res 1985 May;149(3):327-32.PMID:3887143DOI:10.1016/0027-5107(85)90148-4.
The hepatic microsomes derived from rats transformed emodin (1,3,8-trihydroxy-6-methyl-anthraquinone), an anthraquinone present in fungal metabolites and constituent of rhubarb, into at least 10 anthraquinoid metabolites. Metabolite d proved to be mutagenic to Salmonella typhimurium TA1537 in the absence of activation system. MS, NMR, UV and mutagenicity test analysis revealed that metabolite d was 2-Hydroxyemodin (1,2,3,8-tetrahydroxy-6-methyl-anthraquinone) and exhibited mutagenicity in doses of 2-20 micrograms/plate. In addition to this active metabolite, TLC analysis revealed the formation of 4-hydroxyemodin (metabolite a), 5-hydroxyemodin (metabolite b), 7-hydroxyemodin (metabolite d') and others. No mutagenicity of these monohydroxyemodins was demonstrated in the absence of activation system.
omega-Hydroxyemodin, a major hepatic metabolite of emodin in various animals and its mutagenic activity
Mutat Res 1987 Oct;180(2):147-53.PMID:3309636DOI:10.1016/0027-5107(87)90209-0.
The hepatic microsomes derived from various animal species transformed emodin (1,3,8-trihydroxy-6-methylanthraquinone), an anthraquinoid pigment present in fungal metabolites and a constituent of plant medicines, into an unidentified anthraquinone h, along with 2-hydroxy-, 4-hydroxy- and 7-hydroxyemodins. TLC, UV, MS and NMR clarified this unidentified major metabolite as omega-hydroxy-emodin (1,3,8-trihydroxy-6-hydroxymethylanthraquinone). Among 7 animal species, the highest activity to produce this omega-hydroxyemodin was observed in the hepatic microsomes of guinea pig and rat, followed by mouse and rabbit. The microsomal activity to convert emodin into omega-hydroxyemodin was accelerated by the pretreatment of animals with phenobarbital, and inhibited by SKF 525A. The microsomal hydroxylation reactions of the methyl residue and the anthraquinoid nucleus of emodin were presumed to be catalyzed regiospecifically by multiple forms of cytochrome P-450. omega-Hydroxyemodin was not mutagenic to Salmonella typhimurium in the absence of S9, but exhibited mutagenicity in the presence of an activating system. This genotoxic potential was comparable to 2-Hydroxyemodin, a direct-acting mutagen.
Comparative evaluation of antioxidant potential of alaternin (2-Hydroxyemodin) and emodin
J Agric Food Chem 2000 Dec;48(12):6347-51.PMID:11312806DOI:10.1021/jf000936r.
The antioxidant activities of alaternin (2-Hydroxyemodin) and emodin were compared for their respective potentials to inhibit lipid peroxidation in the linoleic acid system by the thiocyanate method, to inhibit total reactive oxygen species generation in kidney homogenates using 2',7'-dichlorodihydrofluorescein diacetate, to inhibit peroxynitrite formation by the 3-morpholinosydnonimine system, which generates superoxide radical and nitrogen monooxide, and to scavenge authentic peroxynitrites. Both alaternin and emodin were found to inhibit the peroxidation of linoleic acid by the thiocyanate method in a dose-dependent manner. Whereas the former shows inhibitory activities in reactive oxygen- and nitogen-mediated reactions, the latter does not. These results indicate that alaternin is a potentially effective and versatile antioxidant and can be used to protect biological systems and functions against various oxidative stresses.
Generation of free radical and hydrogen peroxide from 2-Hydroxyemodin, a direct-acting mutagen, and DNA strand breaks by active oxygen
Toxicol Lett 1987 Jul;37(2):149-56.PMID:3299878DOI:10.1016/0378-4274(87)90151-2.
Among several hydroxylated metabolites of emodin, a fungal anthraquinone and constituent of rhubarb, 2-Hydroxyemodin was a direct-acting mutagen showing a large electron-spin resonance (ESR) signal in the presence of DNA, especially at alkaline pH. Coupled with generation of free radical, hydrogen peroxide but not superoxide was formed. The active oxygen produced from 2-Hydroxyemodin induced strand breaks in phi X 174 replicative form I DNA (supercoiled covalently closed circular duplex DNA). These results suggest a possible role of active oxygen in the process of mutagenesis.
Emodin Derivatives as Multi-Target-Directed Ligands Inhibiting Monoamine Oxidase and Antagonizing Vasopressin V1A Receptors
ACS Omega 2020 Oct 5;5(41):26720-26731.PMID:33110998DOI:10.1021/acsomega.0c03649.
The brain neurotransmitter level is associated with the pathology of various neurodegenerative diseases, and age-dependent increase in the blood level of vasopressin, human brain monoamine oxidase (hMAO) level, oxidative stress, and imbalance in aminergic signaling are common disease-modifying factors leading to various neurodegenerative disorders. Based on the reports of emodin in hMAO inhibition and antagonist effect on the vasopressin V1A receptor, in this study we synthesized six emodin derivatives and evaluated their effects on MAO activity and G protein-coupled receptors. Among them, 4-hydroxyemodin and 5-hydroxyemodin were potent inhibitors of hMAO, and 2-Hydroxyemodin and 5-hydroxyemodin were good V1AR antagonists. In silico molecular docking simulation revealed that the hydroxyl group at C2, C4, and C5 of the respective compounds interacted with prime residues, which corroborates the in vitro effect. Likewise, these three derivatives were predicted to have good drug-like properties. Overall, our study demonstrates that the hydroxyl derivatives of emodin are multi-target-directed ligands that may act as leads for the design and development of a therapy for central nervous system disorders.