Enzymatic alcoholysis was performed in an organic medium to synthesize 2-monoacylglycerol (2-MAG) rich in arachidonic acid. The results showed that solvent type and water activity () significantly affected the 2-MAG yield. Under the optimum conditions, 33.58% 2-MAG was produced in the crude product in -butanol system. Highly pure 2-MAG was obtained after two-stage extraction using 85% ethanol aqueous solution and hexane at first stage and dichloromethane and water at second stage. Isolated 2-MAG was used as substrate to investigate the effect of solvent type and on 2-MAG acyl migration in a lipase-inactivated system. The results indicated that non-polar solvents accelerated the acyl migration of 2-MAG, whereas isomerization was inhibited in polar solvent systems. The exhibited the strongest inhibition effect on 2-MAG isomerization at 0.97, but also affected the hydrolysis of glycerides and lipase selectivity.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9601288PMC
http://dx.doi.org/10.3390/foods11203213DOI Listing

Publication Analysis

Top Keywords

acyl migration
12
enzymatic alcoholysis
8
water activity
8
2-mag
8
solvent type
8
2-mag isomerization
8
preparation 2-arachidonoylglycerol
4
2-arachidonoylglycerol enzymatic
4
alcoholysis effects
4
solvent
4

Similar Publications

2-arachnadoyl glycerol (2-AG) is one of the most common endocannabinoid molecules with anti-proliferative, cytotoxic, and pro-proliferative effects on different types of tumors. Typically, it induces cell death via cannabinoid receptor 1/2 (CB1/CB2)-linked ceramide production. In breast cancer, ceramide is counterbalanced by the sphingosine-1-phosphate, and thus the mechanisms of 2-AG influence on proliferation are poorly understood.

View Article and Find Full Text PDF

Acyl-CoA oxidase 1 (ACOX1), a member of the acyl-coenzyme A oxidase family, is considered a crucial regulator whose dysregulation is implicated in the occurrence and progression of various cancers. This study aims to elucidate the impact of ACOX1 in CRC, shedding light on its potential as a therapeutic target. Through analysis of the GEO dataset, it was found that ACOX1 is significantly downregulated in colorectal cancer (CRC), and this lower expression level is associated with a worse prognosis.

View Article and Find Full Text PDF

DNA methylation of ACADS promotes immunogenic cell death in hepatocellular carcinoma.

Cell Biosci

January 2025

Division of Hepatobiliary and Pancreatic Surgery, Department of Surgery, First Affiliated Hospital, School of Medicine, Zhejiang University, Hangzhou, 310003, Zhejiang, China.

Background: Altered metabolism has become an important characteristic of cancer, and acyl-CoA dehydrogenase short-chain (ACADS), a regulator of lipid synthesis, is involved in carcinogenesis-associated metabolic pathways. DNA methylation is an important mechanism for silencing ACADS in various malignancies. However, the specific role of ACADS in hepatocellular carcinoma (HCC) pathogenesis remains poorly understood.

View Article and Find Full Text PDF

Complementary methods toward the selective functionalization of indole and oxindole frameworks employing an alternative strategy in heteroaryl C-H functionalizations are presented herein. This work focuses on a catalyst-controlled, site selective C-H activation/functionalization of 3-acyl indoles, wherein an amide serves as a robust and versatile directing group capable of undergoing concomitant 1,2-acyl translocation/C-H functionalization in the presence of a Rh/Ag co-catalysts to provide the cross-coupled adducts in high yields. In contrast, the use of Ir/Ag catalysts subverted the 1,2-acyl migration to afford the corresponding C2-functionalized products in good to excellent yields.

View Article and Find Full Text PDF

Clinical Significance of Acyl-CoA Dehydrogenase Short Chain and Its Anti-tumor Role in Hepatocellular Carcinoma by Inhibiting Canonical Wnt/β-Catenin Pathway.

Dig Dis Sci

January 2025

Department of General Surgery, The Fifth People's Hospital of Shanghai, Fudan University, No. 801 Heqing Road, Minhang District, Shanghai, 200240, China.

Background: The pathogenesis of hepatocellular carcinoma (HCC) emphasizes metabolic disorders. HCC patients showed abnormally low expression of Acyl-CoA dehydrogenase short chain (ACADS).

Objectives: This study aimed to elucidate the clinical significance and mechanistic role of ACADS in HCC.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!