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24-Methylenecycloartanyl ferulate Sale

(Synonyms: gamma-谷维素) 目录号 : GC64670

24-Methylenecycloartanyl ferulate 是一种 γ-谷维素化合物。24-Methylenecycloartanyl ferulate 能促进人乳腺癌细胞中的 parvin-beta 的表达。24-Methylenecycloartanyl ferulate 是潜在的 ATP 竞争性的 Akt1 抑制剂 (EC50= 33.3μM)。

24-Methylenecycloartanyl ferulate Chemical Structure

Cas No.:469-36-3

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产品描述

24-Methylenecycloartanyl ferulate is a γ-oryzanol compound. 24-Methylenecycloartanyl ferulate promotes parvin-beta expression in human breast cancer cells. 24-Methylenecycloartanyl ferulate is a potential ATP-competitive Akt1 inhibitor (EC50= 33.3μM)[1].

[1]. Heon Woong Kim, et al. 24-Methylenecycloartanyl ferulate, a major compound of γ-oryzanol, promotes parvin-beta expression through an interaction with peroxisome proliferator-activated receptor-gamma 2 in human breast cancer cells. Biochem Biophys Res Commun. 2015 Dec 25;468(4):574-9.

Chemical Properties

Cas No. 469-36-3 SDF Download SDF
别名 gamma-谷维素
分子式 C41H60O4 分子量 616.91
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Research Update

24-Methylenecycloartanyl ferulate, a major compound of γ-oryzanol, promotes parvin-beta expression through an interaction with peroxisome proliferator-activated receptor-gamma 2 in human breast cancer cells

Biochem Biophys Res Commun 2015 Dec 25;468(4):574-9.PMID:26549231DOI:10.1016/j.bbrc.2015.10.147.

Parvin-β is an adaptor protein that binds to integrin-linked kinase (ILK) and is significantly downregulated in breast tumors and breast cancer cell lines. We treated the breast cancer cell line MCF7 with 24-Methylenecycloartanyl ferulate (24-MCF), a γ-oryzanol compound. We observed upregulation of parvin-β (GenBank Accession No. AF237769) and peroxisome proliferator-activated receptor (PPAR)-γ2 (GenBank Accession No. NM_015869). Among γ-oryzanol compounds, only treatment with 24-MCF led to the formation of reverse transcription-PCR products of parvin-β (650 and 500 bp) and PPAR-γ2 (580 bp) in MCF7 cells, but not in T47D, SK-BR-3, or MDA-MB-231 cells. 24-MCF treatment increased the mRNA and protein levels of parvin-β in MCF7 cells in a dose-dependent manner. We hypothesized that there is a correlation between parvin-β expression and induction of PPAR-γ2. This hypothesis was investigated by using a promoter-reporter assay, chromatin immunoprecipitation, and an electrophoretic mobility shift assay. 24-MCF treatment induced binding of PPAR-γ2 to a peroxisome proliferator response element-like cis-element (ACTAGGACAAAGGACA) in the parvin-β promoter in MCF7 cells in a dose-dependent manner. 24-MCF treatment significantly decreased anchorage-independent growth and inhibited cell movement in comparison to control treatment with dimethyl sulfoxide. 24-MCF treatment reduced the levels of GTP-bound Rac1 and Cdc42. Evaluation of Akt1 inhibition by 24-MCF revealed that the half maximal effective concentration was 33.3 μM. Docking evaluations revealed that 24-MCF binds to the ATP-binding site of Akt1(PDB ID: 3OCB) and the compound binding energy is -8.870 kcal/mol. Taken together, our results indicate that 24-MCF treatment increases parvin-β expression, which may inhibit ILK downstream signaling.

Definitive evidence of the presence of 24-Methylenecycloartanyl ferulate and 24-methylenecycloartanyl caffeate in barley

Sci Rep 2019 Aug 29;9(1):12572.PMID:31467350DOI:10.1038/s41598-019-48985-6.

γ-Oryzanol (OZ), which has a lot of beneficial effects, is a mixture of ferulic acid esters of triterpene alcohols (i.e., triterpene alcohol type of OZ (TTA-OZ)) and ferulic acid esters of plant sterols (i.e., plant sterol type of OZ (PS-OZ)). Although it has been reported that OZ is found in several kinds of cereal typified by rice, TTA-OZ (e.g., 24-Methylenecycloartanyl ferulate (24MCA-FA)) has been believed to be characteristic to rice and has not been found in other cereals. In this study, we isolated a compound considered as a TTA-OZ (i.e., 24MCA-FA) from barley and determined the chemical structure using by HPLC-UV-MS, high-resolution MS, and NMR. Based on these results, we proved for the first time that barley certainly contains 24MCA-FA (i.e., TTA-OZ). During the isolation and purification of 24MCA-FA from barley, we found the prospect that a compound with similar properties to OZ (compound-X) might exist. To confirm this finding, the compound-X was also isolated, determined the chemical structure, and identified as a caffeic acid ester of 24-methylenecycloartanol (24MCA-CA), which has rarely been reported before. We also quantified these compounds in various species of barley cultivars and found for the first time the existence of 24MCA-FA and 24MCA-CA in various barley. Through these findings, it opens the possibility to use barley as a new source of 24MCA-FA and 24MCA-CA.

Author Correction: Definitive evidence of the presence of 24-Methylenecycloartanyl ferulate and 24-methylenecycloartanyl caffeate in barley

Sci Rep 2020 Jan 17;10(1):974.PMID:31949253DOI:10.1038/s41598-020-57690-8.

An amendment to this paper has been published and can be accessed via a link at the top of the paper.

Isolation and Structure Determination of 24-Methylenecycloartanyl ferulate from Indian Rice Bran and Its Quantitative Analysis

Pharmacogn Mag 2016 May;12(Suppl 3):S307-14.PMID:27563217DOI:10.4103/0973-1296.185722.

Background: γ-oryzanol is a major bioactive constituent in rice. Most of the literature reports isolation of 24-Methylenecycloartanyl ferulate (24-mCAF) from rice bran oil (RBO) of other than Indian variety. Current research has successfully applied high-performance thin layer chromatography (HPTLC) method for isolation of 24-mCAF from Indian variety (Indrayani) of RBO. Materials and methods: HPTLC method was developed for standard γ-oryzanol using tinidazole as an internal standard. The proposed HPTLC method was optimized and validated as per the guidelines stated by the International Conference on Harmonization Q2 R1 recommendations. The mobile phase composed of toluene:ethyl acetate:methanol (15.0:1.7:3.3, (v/v/v) was selected because well-resolved peaks were obtained. The optimum wavelength chosen for detection and quantitation was 317 nm. Results: The retention factors for tinidazole, 24-mCAF, and CAF were found to be 0.27 ± 0.02, 0.72 ± 0.02, and 0.79 ± 0.02, respectively. The percent content of 24-mCAF in ethanol fraction was found to be 1.02%. The 24-mCAF was isolated from RBO using HPTLC method. Conclusion: The characterization data of 1D, 2D spectral analysis confirm that the isolated compound 1 is 24-mCAF. Summary: HPTLC method was developed for standard γ-oryzanol using tinidazole as an internal standardThe proposed HPTLC method was optimized and validated as per the guidelines stated by the ICH Q2 R1 recommendationsThe characterization data of 1D, 2D spectral analysis confirms that the isolated compound is 24-methylenecycloartanyl ferulateIn this work, high purity 24-mCAF was successfully isolated from crude RBO using HPTLC with a solvent system composed toluene: ethyl acetate: methanol (15.0:1.7:3.3, v/v/v) Abbreviations used: RBO: Rice Bran Oil, CAF: Cycloartenol ferulic acid, 24-mCAF: 24-Methylcycloartenol ferulic acid, HPLC: High-Performance Liquid Chromatography, HPTLC: High-Performance Thin Layer Chromatography, 1H: Proton nuclear magnetic resonance spectroscopy, 13C: Carbon-13 nuclear magnetic resonance spectroscopy, COSY: Correlation spectroscopy, NOESY: Nuclear overhauser effect spectroscopy, HMBC: Heteronuclear multiple bond correlation nuclear magnetic resonance spectroscopy, HSQC: heteronuclear single quantum coherence nuclear magnetic resonance spectroscopy.

Functional Profiling and Future Research Direction of Rice Bran Oil in Bangladesh

J Oleo Sci 2021;70(11):1551-1563.PMID:34732634DOI:10.5650/jos.ess21212.

Rice bran oil (RBO) has been demonstrated to affect complex malfunctioned conditions such as oxidative stress, hyperlipidemia, hyperglycemia, hypertension, inflammation, abnormal cell growth (cancer), ulceration, immune and cognitive modulation. This unique effect of RBO is due to the presence of well-balanced fatty acid composition and several bioactive compounds, γ- oryzanol (cycloartenyl ferulate, 24-Methylenecycloartanyl ferulate, campesterol ferulate, and β-sitosteryl ferulate), vitamin E (tocopherol and tocotrienol), phytosterols (β-sitosterol, campesterol and stigmasterol) and other nutrients. The RBO composition of bioactive compounds varied geographically, thus the clear-cut mechanisms of action on complex disease cascades are still required. This review article summarized the RBO compositional profiling and compared it with other edible oils. This article also summarized Bangladesh RBO profiling and their proposed mechanism of action as well as the first line of defense in the prevention, management, and control of complex disease conditions. This review indicates how Bangladesh RBO increase their opportunity to be functional food for 21st century's ailment.