O-Desmethylangolensin
(Synonyms: O-DMA) 目录号 : GC61150
A phytoestrogen and an active metabolite of diadzein
Cas No.:21255-69-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
O-Desmethylangolensin (O-DMA) is a phytoestrogen and an active metabolite of daidzein .1 It is formed from daidzein by gut microbiota. O-DMA (2.5-50 ?M) is cytotoxic to MDA-MB-231 cells.2
1.Frankenfeld, C.L.O-desmethylangolensin: The importance of equol's lesser known cousin to human healthAdv. Nutr.2(4)317-324(2011) 2.Magee, P.J., McGlynn, H., and Rowland, I.R.Differential effects of isoflavones and lignans on invasiveness of MDA-MB-231 breast cancer cells in vitroCancer Lett.208(1)35-41(2004)
| Cas No. | 21255-69-6 | SDF | |
| 别名 | O-DMA | ||
| Canonical SMILES | CC(C1=CC=C(O)C=C1)C(C2=CC=C(O)C=C2O)=O | ||
| 分子式 | C15H14O4 | 分子量 | 258.27 |
| 溶解度 | DMSO : 62.5 mg/mL (241.99 mM; ultrasonic and warming and heat to 60°C) | 储存条件 | Store at -20°C |
| 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 | 3.8719 mL | 19.3596 mL | 38.7192 mL |
| 5 mM | 0.7744 mL | 3.8719 mL | 7.7438 mL |
| 10 mM | 0.3872 mL | 1.936 mL | 3.8719 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。
O-Desmethylangolensin: the importance of equol's lesser known cousin to human health
Adv Nutr 2011 Jul;2(4):317-24.PMID:22332073DOI:10.3945/an.111.000539.
The objective for this paper was to review human studies of O-Desmethylangolensin (O-DMA) concentrations and of O-DMA producers compared with nonproducers in the context of results from in vitro studies. O-DMA is an intestinal bacterial metabolite of daidzein, an isoflavone compound observed to have phytoestrogenic properties. Not all individuals harbor bacteria capable of metabolizing daidzein to O-DMA, and individuals can be classified as O-DMA producers and nonproducers. O-DMA is less structurally similar to 17β-estradiol than its parent compound, daidzein; thus, it may exhibit different biological actions than daidzein. Evidence from in vitro studies suggests that O-DMA has several cancer-related biological actions. However, results from human metabolic studies and observational studies of disease risk suggest that these actions may not be physiologically relevant in vivo due to the amount and form (primarily glucuronide) of circulating O-DMA. Apart from circulating O-DMA concentrations, the underlying bacteria may have a distinct physiological role. Urinary excretion of O-DMA in humans is a marker of harboring intestinal bacteria capable of C-ring cleavage. Bacterial C-ring cleavage reactions are relevant to other phytochemicals that may exert biological actions in vivo that are stronger than the actions of O-DMA; thus, the role of the phenotype may extend beyond daidzein metabolism. There are a limited number of studies that have evaluated disease risk factors in relation to being an O-DMA producer, with mixed results. Further research evaluating disease risk in relation to the O-DMA-producer phenotype from the perspective of intestinal microbial composition is recommended.
Production of O-Desmethylangolensin, tetrahydrodaidzein, 6'-hydroxy-O-desmethylangolensin and 2-(4-hydroxyphenyl)-propionic acid in fermented soy beverage by lactic acid bacteria and Bifidobacterium strains
Food Chem 2020 Jul 15;318:126521.PMID:32151927DOI:10.1016/j.foodchem.2020.126521.
Isoflavones intake is associated with health benefits. The metabolism of isoflavones by bacteria plays a key role in their biotransformation. Therefore, commercial soy drink was fermented by 11 lactic acid bacteria (LAB) and 9 bifidobacteria strains. The majority of the strains showed deglycosylation of the isoflavone glycosides present in soy drink and appearance of the aglycones daidzein, genistein and glycitein. Moreover, we observed the further transformation of daidzein into O-Desmethylangolensin (O-DMA) and tetrahydrodaidzein, alongside with dihydrodaidzein (DHD) and a putative isomer of DHD. On the other hand, genistein was transformed by nearly all strains into 6-hydroxy-O-desmethylangolensin (6-hydroxy-O-DMA), but no dihydrogenistein production was registered. A high concentration of 2-(4-hydroxyphenyl)-propionic acid was observed, suggesting the degradation of O-DMA and 6-hydroxy-O-DMA. The potential of LAB and Bifidobacterium strains to produce functional soy drink enriched with bioactive isoflavones is demonstrated in this work.
R(-)-O-desmethylangolensin is the main enantiomeric form of daidzein metabolite produced by human in vitro and in vivo
J Chromatogr B Analyt Technol Biomed Life Sci 2014 Mar 15;953-954:30-7.PMID:24561352DOI:10.1016/j.jchromb.2014.01.048.
After ingestion, human intestinal bacteria transform daidzein into dihydrodaidzein, which can be further metabolised to O-Desmethylangolensin. This metabolite, unlike daidzein, has a chiral centre and can therefore occur as two distinct enantiomers; however, it is unclear which enantiomer is present in humans. The aim of this study was to define in vitro and in vivo the structure of O-Desmethylangolensin and then to evaluate its pharmacokinetic parameters. Daidzein metabolism was preliminarily investigated in anaerobic batch cultures inoculated with mixed faecal bacteria from O-Desmethylangolensin producer volunteers. The transformation was monitored by liquid chromatography-mass spectrometry and a chiral column was used to distinguish dihydrodaidzein and O-Desmethylangolensin enantiomers. These were purified, analysed by circular dichroism and the results established R(-)-O-desmethylangolensin as the main product (enantiomer excess 91%). However, both dihydrodaidzein enantiomers were detected. Similar results were obtained by in vivo trials. The in vitro formation of O-Desmethylangolensin seems to be directly correlated with the number of transforming microorganisms. This correlation was found in vivo for tmax but not for other pharmacokinetic indexes. The pharmacokinetics of daidzein, dihydrodaidzein and O-Desmethylangolensin were then evaluated in 11 healthy adult O-Desmethylangolensin producers after the single administration of soy milk containing 100mg daidzein. The conjugated forms of daidzein, dihydrodaidzein and O-Desmethylangolensin represent more than 90 and 95% of the plasmatic and urinary forms, respectively. The Cmax, tmax and half-life of O-Desmethylangolensin in plasma were 62±53nM, 28±11 and 15±6h, respectively. Relevant inter-individual variations were observed as indicated by the high standard deviations.
Stereochemical determination of O-Desmethylangolensin produced from daidzein
Food Chem 2015 Mar 15;171:153-6.PMID:25308655DOI:10.1016/j.foodchem.2014.08.122.
We had isolated an O-Desmethylangolensin (O-DMA)-producing bacterium, Clostridium rRNA cluster XIVa strain SY8519. According to chiral separation using HPLC, the SY8519-produced O-DMA exhibited high optical purity. To determine the absolute stereochemistry of O-DMA, we prepared 2-(4-hydroxyphenyl)propionic acid (2-HPPA) from the O-DMA using the Baeyer-Villiger reaction. From chiral analysis of the product, the major peak had the same stereochemistry to that of 2-HPPA produced from genistein by the same bacteria. As we have determined the stereochemistry of SY8519-produced 2-HPPA to have an R configuration, by the chemical synthesis of (S)-2-HPPA, the SY8519-produced O-DMA must also possess R stereochemistry at the 2-position. To study the stereoselective metabolism, we applied racemic dihydrodaidzein to SY8519. The O-DMA was isolated from the culture media and starting material was also recovered. The O-DMA produced was optically active in a similar manner to that produced from daidzein. However, the remaining dihydrodaidzein exhibited no difference between the enantiomers. These results suggested that SY8519 produces (R)-O-DMA from both enantiomers of dihydrodaidzein.
O-Desmethylangolensin inhibits the proliferation of human breast cancer MCF-7 cells by inducing apoptosis and promoting cell cycle arrest
Oncol Lett 2013 Dec;6(6):1784-1788.PMID:24260076DOI:10.3892/ol.2013.1601.
The aim of the present study was to investigate the anticancer effect of O-Desmethylangolensin (O-DMA) by assessing cell proliferation, apoptosis and cell cycle distribution, as well as exploring the mechanisms underlying these effects in breast carcinoma MCF-7 cells. The cells were exposed to O-DMA (5-200 μM) for 24, 48 and 72 h. The results revealed that cell proliferation was significantly inhibited in a dose-dependent manner following treatment for 48 and 72 h, but not after 24 h, and resulted in the significant induction of apoptosis and the promotion of cell cycle arrest at the G1/S and G2/M phases. To elucidate these effects of O-DMA, the expression levels of cell cycle regulators were measured in the cells exposed to O-DMA at 150 μM for 72 h. Of the G1/S phase-related proteins, O-DMA modulated the cyclin-dependent kinases (CDKs), with a decrease in CDK2 and CDK4 and an increase in CDK6, and downregulated cyclin D and E. With respect to the G2/M-related proteins, O-DMA caused a reduction in CDK1, together with a slight increase in cyclin A and B. In addition, O-DMA downregulated p21Cip1 and p27Kip1, but not p16INK4a and p15INK4b, and interacted with the CDK6-cyclin D and CDK1-cyclin B complexes. In conclusion, these results indicate for the first time that the regulation of the CDK4/6-cyclin D and CDK1-cyclin B complexes may participate in the anticancer activity pathway of O-DMA in MCF-7 cells.