Acyl migration of 2-monoacylglycerols (2-MAGs) rich in DHA is a universal reaction occurring during storage and structural lipid synthesis, and affects their nutritional value. In this study, their acyl migration was investigated under different systems and temperatures. The enhanced temperature promoted acyl migration, leading to a 5.6-fold increase from 20 °C to 50 °C. The kinetic study indicated rate constants followed the order: hexane > solvent-free > dichloromethane > ethanol ≈ acetone ≈ acetonitrile > t-butanol, and positively correlated with log P of solvent. During acyl migration in ethanol, acetone, acetonitrile and t-butanol at 40 °C, DHA content in 2-MAGs was higher than in 1-MAGs, indicating slow acyl migration of DHA; while at 50 °C, the difference of DHA distribution was small, due to increasing acyl migration rate. The results suggest that acyl migration of different fatty acids can be regulated by changing conditions to enrich DHA at sn-2 position.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.foodchem.2023.135501 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Two-Step Cell Death Induction by the New 2-Arachidonoyl Glycerol Analog and Its Modulation by Lysophosphatidylinositol in Human Breast Cancer Cells.
Int J Mol Sci
January 2025
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, 117997 Moscow, Russia.
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 PDFACOX1 activates autophagy via the ROS/mTOR pathway to suppress proliferation and migration of colorectal cancer.
Sci Rep
January 2025
Department of General Surgery, The First Affiliated Hospital of Soochow University, Suzhou, 215006, Jiangsu, China.
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 PDFDNA 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 PDFCatalyst-controlled directing group translocation in the site selective C-H functionalization of 3-carboxamide indoles and metallocarbenes.
Nat Commun
January 2025
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN, 46556, USA.
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 PDFClinical 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.
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!