Coprostanol
(Synonyms: 粪甾烷-3-醇,Coprosterol) 目录号 : GC40514A cholesterol derivative
Cas No.:360-68-9
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Coprostanol is a cholesterol derivative formed in mammals by intestinal microorganisms and is the odorous compound in feces. [1]It is formed via conversion of cholesterol to cholestenone then coprostanone intermediates or by direct reduction of the 5,6 double bond. Coprostanol is commonly used as a marker of sewage contamination in soil and watersheds.[2][3]
Reference
[1]. Ren, D., Li, L., Schwabacher, A.W., et al. Mechanism of cholesterol reduction to coprostanol by Eubacterium coprostanoligenes ATCC 51222. Steroids 61(1), 33-40 (1996).
[2]. von der Lühe, B., Dawson, L.A., Mayes, R.W., et al. Investigation of sterols as potential biomarkers for the detection of pig (S. s. domesticus) decomposition fluid in soils. Forensic Sci. Int. 230(1-3), 68-73 (2013).
[3]. Nichols, P.D., Leeming, R., Rayner, M.S., et al. Comparison of the abundance of the fecal sterol coprostanol and fecal bacterial groups in inner-shelf waters and sediments near Sydney, Australia. J. Chromatogr. 643(1-2), 189-195 (1993).
| Cas No. | 360-68-9 | SDF | |
| 别名 | 粪甾烷-3-醇,Coprosterol | ||
| 化学名 | (5β)-cholestan-3β-ol | ||
| Canonical SMILES | C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C | ||
| 分子式 | C27H48O | 分子量 | 388.7 |
| 溶解度 | 30 mg/ml in Chloroform, 2mg/mL in DMF, 0.1mg/mL in DMSO, 20mg/mL in Ethanol | 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 2.5727 mL | 12.8634 mL | 25.7268 mL |
| 5 mM | 0.5145 mL | 2.5727 mL | 5.1454 mL |
| 10 mM | 0.2573 mL | 1.2863 mL | 2.5727 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。
Correlation between caffeine and Coprostanol in contrasting Amazonian water bodies
Chemosphere 2023 Jun;326:138365.PMID:36906004DOI:10.1016/j.chemosphere.2023.138365.
The evaluation of contamination by domestic sewage is relevant in the Amazon region; however, it has neither been well-developed nor accompanied by research or monitoring programs. In this study, caffeine and Coprostanol as indicators of sewage were investigated in water samples from Amazonian water bodies that crisscross the city of Manaus (Amazonas state, Brazil) and cover regions with distinct main land uses such as high-density residential, low-density residential, commercial, industrial, and environmental protection areas. Thirty-one water samples were studied based on their dissolved and particulate organic matter (DOM and POM) fractions. Quantitative determination of both caffeine and Coprostanol was carried out using LC-MS/MS with APCI in the positive ionization mode. The streams of the urban area of Manaus had the highest concentrations of caffeine (1.47-69.65 μg L-1) and Coprostanol (2.88-46.92 μg L-1). Samples from the peri-urban Tarumã-Açu stream and from the streams in the Adolpho Ducke Forest Reserve showed much lower concentrations of caffeine (20.20-165.78 ng L-1) and Coprostanol (31.49-120.44 ng L-1). Samples from the Negro River showed a wider range of concentrations of caffeine (20.59-873.59 ng L-1) and Coprostanol (31.72-706.46 ng L-1), with the highest values found in the outfalls of the urban streams. Levels of caffeine and Coprostanol were significantly positively correlated in the different organic matter fractions. The Coprostanol/(Coprostanol + cholestanol) ratio proved to be a more suitable parameter than the Coprostanol/cholesterol one in low-density residential areas. Proximity to densely populated areas and the flow of water bodies appear to influence the caffeine and Coprostanol concentrations, which was observed in their clustering in the multivariate analysis. The results indicate that caffeine and Coprostanol can be detected even in water bodies that receive very low domestic sewage input. Therefore, this study revealed that both caffeine in DOM and Coprostanol in POM represent viable alternatives for use in studies and monitoring programs even in remote areas of the Amazon, where microbiological analyses are often unfeasible.
Cholesterol Metabolism by Uncultured Human Gut Bacteria Influences Host Cholesterol Level
Cell Host Microbe 2020 Aug 12;28(2):245-257.e6.PMID:32544460DOI:10.1016/j.chom.2020.05.013.
The human microbiome encodes extensive metabolic capabilities, but our understanding of the mechanisms linking gut microbes to human metabolism remains limited. Here, we focus on the conversion of cholesterol to the poorly absorbed sterol Coprostanol by the gut microbiota to develop a framework for the identification of functional enzymes and microbes. By integrating paired metagenomics and metabolomics data from existing cohorts with biochemical knowledge and experimentation, we predict and validate a group of microbial cholesterol dehydrogenases that contribute to Coprostanol formation. These enzymes are encoded by ismA genes in a clade of uncultured microorganisms, which are prevalent in geographically diverse human cohorts. Individuals harboring coprostanol-forming microbes have significantly lower fecal cholesterol levels and lower serum total cholesterol with effects comparable to those attributed to variations in lipid homeostasis genes. Thus, cholesterol metabolism by these microbes may play important roles in reducing intestinal and serum cholesterol concentrations, directly impacting human health.
Mechanism of cholesterol reduction to Coprostanol by Eubacterium coprostanoligenes ATCC 51222
Steroids 1996 Jan;61(1):33-40.PMID:8789734DOI:10.1016/0039-128x(95)00173-n.
The mechanism of reduction of cholesterol to Coprostanol by Eubacterium coprostanoligenes ATCC 51222 was studied by incubating the bacterium with a mixture of alpha- and beta-isomers of [4-3H,4-14C]cholesterol. Coprostanol, isolated after incubation of [4-3H,4-14C]cholesterol in a growth medium under anaerobic conditions, retained 97% of the tritium originally present in cholesterol. The majority of this tritium (64%), however, was in the C-6 position in Coprostanol, which showed that the conversion of cholesterol into Coprostanol by E. coprostanoligenes involved the intermediate formation of 4-cholesten-3-one followed by the reduction of the latter to Coprostanol. In resting cell assays in which washed bacterial cells were incubated with micellar cholesterol in phosphate buffer at 37 degrees C, both 4-cholesten-3-one and coprostanone were produced in addition to Coprostanol. Furthermore, 5-cholesten-3-one, 4-cholesten-3-one, and coprostanone were converted efficiently to Coprostanol by E. coprostanoligenes. These results support the hypothesis that the major pathway for reduction of cholesterol by E. coprostanoligenes involves the intermediate formation of 4-cholesten-3-one followed by reduction of the latter to Coprostanol through coprostanone as an intermediate.
Methyl Ether-Derivatized Sterols and Coprostanol Produced via Thermochemolysis Using Tetramethylammonium Hydroxide (TMAH)
Molecules 2019 Nov 7;24(22):4040.PMID:31703423DOI:10.3390/molecules24224040.
Sterols are widely distributed in nature from lipids in organisms to sediments. As a conventional method, extraction and derivatization with TMS have been applied for sterol analysis, requiring a long preparation time for gas chromatography-mass spectrometry analysis. In this study, for sterol analysis, thermochemolysis using tetramethylammonium hydroxide (TMAH) was applied. This method performs hydrolysis and methylation simultaneously; thus, free and ether-bonding sterols can be analyzed as sterol methyl ethers in a relatively short time period. A sediment sample from a tideland (the Yatsu tideland, Japan) was analyzed using the TMAH method, and we detected more than 10 sterols, which include cholest-5-en-3β-ol (cholesterol), 24-ethylcholest-5-en-3β-ol (sitosterol), 24-methylcholesta-5,22E-3β-ol (brassicasterol), 24-ethylcholesta-5,24(28)Z-dien-3β-ol (isofucosterol), 4α,23,24-trimethyl-5α(H)-cholest-22E-en-3β- ol (dinosterol), and 5β(H)-cholestan-3β-ol (Coprostanol). The detection of the various sterols can be attributed to multiple natural and artificial sources around the Yatsu tideland. In this paper, the mass spectra of these sterols are provided together with an interpretation of their fragmentation patterns. Additionally, the fecal pollution in the Yatsu tideland is discussed in the context of the detection of Coprostanol.
Evidence of Coprostanol estrogenicity to the freshwater mussel Elliptio complanata
Environ Pollut 2001;115(1):97-106.PMID:11586778DOI:10.1016/s0269-7491(01)00089-6.
Coprostanol (5 beta (H)-cholestan-3 beta ol) is a reduced metabolite of cholesterol produced by micro-organisms found in the intestinal tract of mammals. This substance abounds in urban effluents and is accumulated by organisms living in the vicinity of municipal effluent outfalls. In an earlier study, freshwater mussels exposed to contaminated river water for 62 days accumulated large quantities of Coprostanol (Cop) in their soft tissues (16 micrograms/g dry wt.). Moreover, these mussels were found to have elevated levels of vitellin in their hemolymphs, suggesting estrogenic effects. Although municipal wastewaters are known to contain other estrogenic compounds capable of inducing Vn synthesis in mussels, the estrogenic potential of Coprostanol was singled out for examination. To this end, mussels were first injected with concentrations of Coprostanol via the abductor muscle route, and allowed to stand in aerated water for 72 h at 15 degrees C. The levels of Vn in mussel hemolymph were assayed using the organic alkali-labile phosphate method. A competitive estradiol-binding assay was then devised to measure the ability of Coprostanol to compete in the binding of fluorescein-labeled estradiol-albumin to cytosolic proteins. Coprostanol partially reversed the binding of labeled estradiol-albumin to cytosolic proteins with an EC50 of 1 mM. In addition, injections of Coprostanol and estradiol-17 beta led to increased levels of vitellins in the hemolymph of treated mussels. Moreover, incubation of cop in gonad homogenate extracts in the presence of NADPH led to the formation of two compounds, as determined by high-performance thin-layer chromatography. One of these compounds appears to be the C17 oxidation product of Coprostanol, whose polarity is similar to that of estradiol. The results present evidence that Coprostanol is estrogenic to freshwater mussels.