2. Academic Validation
  3. Oxygen-Driven Thermal Degradation of Isorhamnetin in Boiling Water: Product Profiling, Energetics, and Antiobesity Mechanisms in Caenorhabditis elegans

Oxygen-Driven Thermal Degradation of Isorhamnetin in Boiling Water: Product Profiling, Energetics, and Antiobesity Mechanisms in Caenorhabditis elegans

  • J Agric Food Chem. 2026 Mar 11;74(9):7636-7651. doi: 10.1021/acs.jafc.5c16629.
Shiye Lin 1,  Wenqi Huang 1,  Haolin Zhang 2,  Kefeng Zhai 3,  Shengxiong Chen 1,  Xincheng Wu 1,  Haoming Wu 1,  Pengren Zou 1,  Mohamed A Farag 4,  Jesús Simal-Gándara 1,  Jianbo Xiao 1,  Hui Cao 1
Affiliations

Affiliations

  • 1 Nutrition and Bromatology Group, Department of Analytical and Food Chemistry, Faculty of Sciences, Universidade de Vigo, Ourense 32004, Spain.
  • 2 College of Food Science and Technology, Guangdong Ocean University, Zhanjiang 524088, China.
  • 3 School of Biological and Food Engineering, Engineering Research Center for Development and High Value Utilization of Genuine Medicinal Materials in North Anhui Province, Suzhou University, Suzhou, Anhui 234000, China.
  • 4 Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, Cairo 11562, Egypt.
PMID: 41738067 DOI: 10.1021/acs.jafc.5c16629
Abstract

Dietary Flavonoids readily undergo structural transformations upon heating, and it remains unclear whether their postheat bioactivity is driven by the parent compounds or its degradation products. Here, we constructed a time-resolved three-dimensional product-structure-activity network of isorhamnetin (ISO) in boiling water. A total of 12 products were identified and classified as phenolic acids, hydroxylated adducts, and dimers. Density functional theory calculations supported a degradation mechanism involving quinone formation, hydroxide attack at the C2 position, and C-ring cleavage. Further biological evaluation revealed that ISO and its key degradation products, phloroglucinol and 2,4,6-trihydroxybenzoic acid, mitigated glucose-induced metabolic reprogramming, and lipid accumulation in Caenorhabditis elegans through a DAF-16/FOXO-dependent mechanism associated with H3K4me3/H3K27me3. Overall, this work presents a structural landscape of ISO under cooking-like conditions and provides new insight into the retention of bioactivity during the thermal transformation of Polyphenols.

Keywords

antiobesity; degradation; isorhamnetin; phenolic acid; ring-cleavage.

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