9(S)-HpODE
目录号 : GC40357
A 5-LO product derived from linoleic acid
Cas No.:29774-12-7
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
9(S)-HpODE is produced by the action of arachidonate 5-LO on linoleic acid. It can be further metabolized by potato hydroperoxide dehydratase to colneleic acid.
| Cas No. | 29774-12-7 | SDF | |
| Canonical SMILES | CCCCC/C=C\C=C\[C@@H](OO)CCCCCCCC(O)=O | ||
| 分子式 | C18H32O4 | 分子量 | 312.4 |
| 溶解度 | DMF: >50 mg/ml (per Rao Maddipati),DMSO: >50 mg/ml (per Rao Maddipati),Ethanol: >50 mg/ml (per Rao Maddipati),PBS pH 7.2: >1 mg/ml (from 13(S)-HODE) | 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 | 3.201 mL | 16.0051 mL | 32.0102 mL |
| 5 mM | 0.6402 mL | 3.201 mL | 6.402 mL |
| 10 mM | 0.3201 mL | 1.6005 mL | 3.201 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。
Biosynthesis and isomerization of 11-hydroperoxylinoleates by manganese- and iron-dependent lipoxygenases
Lipids 2004 Apr;39(4):319-23.PMID:15357019DOI:10.1007/s11745-004-1235-1.
Manganese lipoxygenase (Mn-LO) oxygenates linoleic acid (LA) to a mixture of the hydroperoxides--11 (S)-hydroperoxy-9Z,12Z-octadecadienoic acid [11(S)-HPODE] and 13(R)-hydroperoxy-9Z,11 E-octadecadienoic acid [13(R)-HPODE]-- and also catalyzes the conversion of 11 (S)-HPODE to 13(R)-HPODE via oxygen-centered (LOO-) and carbon-centered (L.) radicals [Hamberg, M., Su, C., and Oliw, E. (1998) Manganese Lipoxygenase. Discovery of a Bis-allylic Hydroperoxide as Product and Intermediate in a Lipoxygenase Reaction, J. Biol. Chem. 273, 13080-13088]. The aims of the present work were to investigate whether 11-HPODE can also be produced by iron-dependent lipoxygenases and to determine the enzymatic transformations of stereoisomers of 11-HPODE by lipoxygenases. Rice leaf pathogen-inducible lipoxygenase, but not soybean lipoxygenase-1 (sLO-1), generated a low level of 11-HPODE (0.4%) besides its main hydroperoxide, 13(S)-HPODE, on incubation with LA. Steric analysis revealed that 11-HPODE was enriched with respect to the R enantiomer [74% 11(R)]. In agreement with previous results, 11 (S)-HPODE incubated with Mn-LO provided 13(R)-HPODE, and the same conversion also took place with the methyl ester of 11(S)-HPODE. 11(R,S)-HPODE was metabolized biphasically in the presence of Mn-LO, i.e., by a rapid phase during which the 11(S)-enantiomer was converted into 13(R)-HPODE and a slow phase during which the 11(R)-enantiomer was converted into 9(R)-HPODE. sLO-1 catalyzed a slow conversion of 11 (S)-HPODE into a mixture of 13(R)-HPODE (75%), 9(S)-HpODE (10%), and 13(S)-HPODE (10%), whereas 11(R,S)-HPODE produced a mixture of nearly racemic 13-HPODE (approximately 70%) and 9-HPODE (approximately 30%). The results showed that 11HPODE can also be produced by an iron-dependent LO and suggested that the previously established mechanism of isomerization of 11(S)-HPODE involving suprafacial migration of O2 is valid also for the isomerizations of 11(R)-HPODE by Mn-LO and of 11(S)-HPODE by sLO-1.
Analysis of serum polyunsaturated fatty acid metabolites in allergic bronchopulmonary aspergillosis
Respir Res 2020 Aug 5;21(1):205.PMID:32758241DOI:10.1186/s12931-020-01471-4.
Background: The importance of lipid mediators in allergic diseases has been long recognized, whereas little is known about their role in allergic bronchopulmonary aspergillosis (ABPA). We investigated whether lipid mediators are associated with ABPA. Methods: We recruited 12 ABPA patients, 23 asthma patients and 12 healthy control in our study. Serum of 11 ABPA patients were collected before and following treatment. 36 polyunsaturated fatty acid metabolites were measured in serum samples by using liquid chromatography-mass spectrometry. This study was approved by the Ethics Committee of the First Affiliated Hospital of Guangzhou Medical University, with ethics number GYFYY-2016-73. Results: Levels of arachidonic acid (AA), 15(S)-hydroxyeicosatetraenoic acid (HETE), 12(S)-HETE, 8(S)-HETE, 5(S)-HETE, LTB4, PGB2, 12(S)-hydroxyeicosapentaenoic acid (HEPE), 12-hydro-xyheptadecatrienoic acid (HHTrE) were significantly higher in ABPA patients than that in HC groups. Compared with asthma group, ABPA group expressed lower levels of 15(S)-hy-droperoxyeicosatetraenoic acid (HPETE), 5(S)-HPETE, 13(S)-hydroperoxyoctadecadienoic acid (HPODE) and 9(S)-HpODE. In APBA patients, AA level was positively correlated with serumtotal IgE (tIgE). The levels of 12(S)-HPETE, 15(S)-HEPE and 12(S)-HEPE correlated with Asp-ergillus fumigatus specific IgE(A. fumigatus sIgE) positively. Peripheral blood eosinophilia correlated with high levels of 12(S)-HETE and 15(S)-HETE. In addition, the serum levels of15(S)-HETE and 12(S)-HETE in ABPA subjects both declined with the decrease of tIgE, A. fumigatus sIgE and sIgG concentrations after treatment. Conclusions: We present data regarding the role of polyunsaturated fatty acid metabolites in APBA for the first time. Most of the tested metabolites increased in ABPA when co-mpared with healthy controls and 15(S)-HETE and 12(S)-HETE may play a role in the pat-hogenesis of ABPA. These findings can provide new ideas for diagnosis, therapy and mon-itor of ABPA.
Rat Hair Metabolomics Analysis Reveals Perturbations of Unsaturated Fatty Acid Biosynthesis, Phenylalanine, and Arachidonic Acid Metabolism Pathways Are Associated with Amyloid-β-Induced Cognitive Deficits
Mol Neurobiol 2023 Apr 25.PMID:37095368DOI:10.1007/s12035-023-03343-6.
Hair is a noninvasive valuable biospecimen for the long-term assessment of endogenous metabolic disturbance. Whether the hair is suitable for identifying biomarkers of the Alzheimer's disease (AD) process remains unknown. We aim to investigate the metabolism changes in hair after β-amyloid (Aβ1-42) exposure in rats using ultra-high-performance liquid chromatography-high-resolution mass spectrometry-based untargeted and targeted methods. Thirty-five days after Aβ1-42 induction, rats displayed significant cognitive deficits, and forty metabolites were changed, of which twenty belonged to three perturbed pathways: (1) phenylalanine metabolism and phenylalanine, tyrosine, and tryptophan biosynthesis-L-phenylalanine, phenylpyruvate, ortho-hydroxyphenylacetic acid, and phenyllactic acid are up-regulated; (2) arachidonic acid (ARA) metabolism-leukotriene B4 (LTB4), arachidonyl carnitine, and 5(S)-HPETE are upregulation, but ARA, 14,15-DiHETrE, 5(S)-HETE, and PGB2 are opposite; and (3) unsaturated fatty acid biosynthesis- eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), FA 18:3 + 1O, and FA 18:3 + 2O are downregulated. Linoleic acid metabolism belonging to the biosynthesis of unsaturated fatty acid includes the upregulation of 8-hydroxy-9,10-epoxystearic acid, 13-oxoODE, and FA 18:2 + 4O, and downregulation of 9(S)-HpODE and dihomo-γ-linolenic acid. In addition, cortisone and dehydroepiandrosterone belonging to steroid hormone biosynthesis are upregulated. These three perturbed metabolic pathways also correlate with cognitive impairment after Aβ1-42 stimulation. Furthermore, ARA, DHA, EPA, L-phenylalanine, and cortisone have been previously implicated in the cerebrospinal fluid of AD patients and show a similar changing trend in Aβ1-42 rats' hair. These data suggest hair can be a useful biospecimen that well reflects the expression of non-polar molecules under Aβ1-42 stimulation, and the five metabolites have the potential to serve as novel AD biomarkers.
Quality changes in perilla seed powder related to storage duration and temperature
J Food Sci Technol 2020 Jan;57(1):263-273.PMID:31975729DOI:10.1007/s13197-019-04056-2.
Perilla seed powder (PSP) was stored at 25 °C, 35 °C, and 45 °C for 8 weeks. Changes in the metabolite profiles of the powders, including fatty acids, were monitored. Correlations between these changes and quality parameters, including lipid oxidation, color, and antioxidant activity, were analyzed to evaluate the effects of storage duration and temperature on PSP quality. Acid values increased significantly with the duration of storage, but not with temperature. Multivariate statistical analysis was performed to identify differences among the metabolite profiles. The PSP sample stored for 1 week at 45 °C and all samples stored at 25 °C and 35 °C were grouped separately from the control and samples stored at 45 °C for more than 4 weeks. Among the many metabolites associated with these differences, lysophosphatidylethanolamines, tocopherol, sitosterol, tryptophan, 12-hydroxyjasmonic acid glucoside, and maltose correlated negatively with quality parameters with the exception of L* and antioxidant activity. Luteolin, apigenin, luteolin 4'-methyl ester, citric acid, isocitric acid, 9(S)-HpODE, and 3,5-octadien-2-one correlated positively with quality. Although the quantities of some antioxidants and lipids decreased during storage, the results suggested that the quality of PSP samples stored at 25 °C, 35 °C, and 45 °C for 8 weeks was acceptable. This was because lipid oxidation promoted by the storage environment was limited by antioxidants in the samples. These metabolites could be useful for monitoring changes in PSP quality.
Characterization of Metabolites in a Zebrafish Model of Alzheimer's Disease Supplemented with Mussel-Derived Plasmalogens by Ultraperformance Liquid Chromatography Q-Exactive Orbitrap Mass Spectrometry-Based Unbiased Metabolomics
J Agric Food Chem 2021 Oct 20;69(41):12187-12196.PMID:34623133DOI:10.1021/acs.jafc.1c03247.
Plasmalogens (Pls) are bioactive substances enriched in the brain with a regulatory effect on Alzheimer's disease (AD), while their metabolomic influence accompanying AD and the underlying mechanisms remain unclear. Here, we extracted and purified Pls (purity of ≥90%) from mussels and applied unbiased metabolomics using ultraperformance liquid chromatography Q-Exactive Orbitrap mass spectrometry to analyze the variation of metabolites in the major metabolic pathways of AD and revealed the cognitive improvement effect of Pls using an experimental AD zebrafish model. The results showed that 37 differential endogenous metabolites were identified, among which glycerophosphocholine, choline, S-adenosylmethionine (SAM), l-glutamine, linoleic acid, 9(S)-HpODE, methionine, and creatine were the major abnormally regulated metabolites, and the first four metabolites were viewed as potential endogenous markers. This study suggested that systemic metabolic profiling could reveal the potential metabolic networks of AD and illuminated the protective effect of Pls on AD through biochemistry mechanisms and metabolic pathways.