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γ-Linolenic Acid ethyl ester

(Synonyms: γ-亚麻酸乙酯) 目录号 : GC40787

Esterified form of γ-linolenic acid

γ-Linolenic Acid ethyl ester Chemical Structure

Cas No.:31450-14-3

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50mg
¥377.00
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产品描述

α-Linolenic acid (ALA) is an essential fatty acid found in leafy green vegetables. ALA, as part of a low saturated fat diet, helps prevent cardiovascular disease. ALA decreases blood pressure, serum cholesterol levels, and platelet aggregation. Linolenic acid ethyl ester (LAEE) is a neutral, more lipophilic form of the free acid that can be used as an exogenous source of α-linolenic acid. This ethanol metabolite may contribute to ethanol-induced hepatic fibrogenesis through stimulation of intracellular signaling pathways in hepatic stellate cells (HSC). LAEE increases cyclin E expression and Cdk2 activity as well as increases ERK and JNK activity.

Chemical Properties

Cas No. 31450-14-3 SDF
别名 γ-亚麻酸乙酯
Canonical SMILES CC/C=C\C/C=C\C/C=C\CCCCCCCC(OCC)=O
分子式 C20H34O2 分子量 306.5
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1 mM 3.2626 mL 16.3132 mL 32.6264 mL
5 mM 0.6525 mL 3.2626 mL 6.5253 mL
10 mM 0.3263 mL 1.6313 mL 3.2626 mL
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Research Update

The ethanol metabolite, Linolenic Acid ethyl ester, stimulates mitogen-activated protein kinase and cyclin signaling in hepatic stellate cells

Life Sci 2003 Jul 18;73(9):1083-96.PMID:12818718DOI:10.1016/s0024-3205(03)00383-7.

Chronic ethanol consumption can result in hepatic fibrosis and cirrhosis. In addition to oxidative metabolism, ethanol can be metabolized by esterification with fatty acids to form fatty acid ethyl esters (FAEE) such as Linolenic Acid ethyl ester (LAEE). We have previously demonstrated that LAEE has promitogeinc and activating effects on hepatic stellate cells (HSC), but the mechanisms of these actions are not known. Intracellular signaling through MAP kinase pathways, including extracellular signal-regulated kinase (ERK) and c-Jun N-terminal kinase (JNK) can influence the activity of the transcription factor AP-1, while cell-cycle regulatory proteins such as cyclin E and cyclin-dependent kinase (CDK), play an important role in cell proliferation. In this study, we demonstrate that treatment of HSC with LAEE increases cyclin E expression and cyclin E/CDK2 activity, which may underlie the promitogenic effects of this compound. In addition, LAEE increases ERK and JNK activity, and these pathways play an important role in the activation of AP-1-dependent gene expression by LAEE. The stimulation of intracellular signaling pathways in HSC by this well-characterized ethanol metabolite may contribute to ethanol-induced hepatic fibrogenesis.

Folium nelumbinis (Lotus leaf) volatile-rich fraction and its mechanisms of action against melanogenesis in B16 cells

Food Chem 2020 Nov 15;330:127030.PMID:32535311DOI:10.1016/j.foodchem.2020.127030.

This study was aimed at determining the influence of Folium nelumbinis (Lotus leaf) extracts on melanogenesis in vitro models of melanoma cell line. The anticancer activity of four fractions, including petroleum ether (PEE), n-hexane (HE), ethanol (EE), and ethyl acetate (EAE) from F. nelumbinis on B16 cell lines (C57BL/6J melanoma cell), were evaluated after 24 and 48 h treatment. Results showed that PEE as well as volatile-rich fractions of linolenic acid and Linolenic Acid ethyl ester significantly (p < 0.05) reduced tyrosinase activity and melanin content in B16 melanoma cells model. Meanwhile, PEE and its primarily contained compound triggered apoptosis of B16 cells in a dose-dependent way. These results demonstrated that PEE possessed effective activities against melanin and tyrosinase generations through the induction of apoptosis. Moreover, a relation between the volatile-rich fractions of F. nelumbinis and the anticancer effects was demonstrated as well.

Antidiabetic properties of oral treatment of hexane and chloroform fractions of Morus nigra leaves in streptozotocin-induced rats

An Acad Bras Cienc 2021 Dec 8;93(suppl 4):e20210744.PMID:34909830DOI:10.1590/0001-3765202120210744.

Morus nigra L. has been widely used in Brazilian folk medicine for the treatment of diabetes. We evaluate the chemical composition and antidiabetic properties of the hexane (Hex-Mn) and chloroform (Chlo-Mn) fractions obtained by partition of the crude ethanolic extract from the leaves in rats. Chemical composition analysis of Hex-Mn and Chlor-Mn was performed by gas chromatography-mass spectrometry (CG-MS). In vivo and in vitro studies were carried out to compare the antidiabetic activities of the Hex-Mn and Chlor-Mn fractions. Most of the compounds identified in Hex-Mn were α-linolenic acid, stigmast-5-en-3-ol and Linolenic Acid ethyl ester, while in Chlor-Mn, stigmast-5-en-3-ol, palmitic acid and α-linolenic acid were mainly identified. Only Hex-Mn treatment reduced both fasting and postprandial hyperglycemia. Additionally, Hex-Mn preserved body weight gain, preserved the hepatic glycogen content, and also reduced the thiobarbituric acid reactive substances and nitrite levels, as well as restored the superoxide dismutase. Furthermore, digestion of complex carbohydrates and intestinal glucose absorption was prevented by Hex-Mn treatment. Our results suggest that the antidiabetic activity of Hex-Mn may be explained, at least in part, by the insulin sensitivity increase, antioxidant properties and reduction in carbohydrate absorption in the small intestine.

Exploring the mechanism of Yixinyin for myocardial infarction by weighted co-expression network and molecular docking

Sci Rep 2021 Nov 19;11(1):22567.PMID:34799616DOI:10.1038/s41598-021-01691-8.

Yixinyin, the traditional Chinese medicine, has the effects of replenishing righteous qi, and promoting blood circulation to eliminate blood stagnation. It is often used to treat patients with acute myocardial infarction (MI). The purpose of our study is to explore the key components and targets of Yixinyin in the treatment of MI. In this study, we analyzed gene expression data and clinical information from 248 samples of MI patients with the GSE34198, GSE29111 and GSE66360 data sets. By constructing a weighted gene co-expression network, gene modules related to myocardial infarction are obtained. These modules can be mapped in Yixinyin PPI network. By integrating differential genes of healthy/MI and unstable angina/MI, key targets of Yixinyin for the treatment of myocardial infarction were screened. We validated the key objectives with external data sets. GSEA analysis is used to identify the biological processes involved in key targets. Through molecular docking screening, active components that can combine with key targets in Yixinyin were obtained. In the treatment of myocardial infarction, we have obtained key targets of Yixinyin, which are ALDH2, C5AR1, FOS, IL1B, TLR2, TXNRD1. External data sets prove that they behave differently in the healthy and MI (P < 0.05). GSEA enrichment analysis revealed that they are mainly involved in pathways associated with myocardial infarction, such as viral myocarditis, VEGF signaling pathway and type I diabetes mellitus. The docking results showed that the components that can be combined with key targets in YixinYin are Supraene, Prostaglandin B1, isomucronulatol-7,2'-di-O-glucosiole, angusifolin B, Linolenic Acid ethyl ester, and Mandenol. For that matter, they may be active ingredients of Yixinyin in treating MI. These findings provide a basis for the preliminary research of myocardial infarction therapy in traditional Chinese medicine and provide ideas for the design of related drugs.