Catalyst-free oxidative coupling of flavones in food grade alkaline water
Food scientists from the National University of Singapore (NUS) have developed a method to synthesize bioactive bi- and tri-flavones using molecular oxygen and food-grade alkaline water.
Flavonoids are bioactive compounds derived from plants that have a wide range of health benefits. This includes reducing the risk of non-communicable diseases such as hypertension, diabetes and chronic inflammation, as well as controlling infectious diseases such as urinary tract infections. While flavone monomers are relatively abundant in fruits and vegetables, the most potent flavonoid dimers and oligomers are often only present in trace amounts, making it impossible to extract them from natural sources. Due to their complex structures, it is also difficult to synthesize these molecules.
In an article published in Type of communicationProfessor Huang Dejian from the Department of Food Science and Technology, Faculty of Science, NUS, and his research team have developed a catalyst-free method to drive the coupling reaction between flavone monomers to create dimers and flavone oligomers. They discovered that molecular oxygen acts as a hydrogen acceptor in alkaline water, allowing the coupling reaction to take place at room temperature and, in the process, to generate a high yield. Using this method, researchers have synthesized more than 40 flavone dimers and trimers, some of which are completely new. This work is a research collaboration with Professor Kendall Houk of the University of California, Los Angeles.
Professor Huang said: “This reaction was developed from a chance discovery by my PhD student, Dr Yang Xin. Paying attention to details, especially unexpected results when researching, can lead to great discoveries.”
This discovery opens up an environmentally friendly and efficient way to synthesize flavone dimers and oligomers with potential applications in fighting disease and improving human health. These can potentially be used as active ingredients or pharmaceutical agents to fortify foods, produce nutritional supplements and treat disease.
With the small library of bi- and tri-flavones synthesized from their newly discovered method, Professor Huang and his research team screened the bioactivity of these flavonoids, including antiviral, anti-aging and inhibition of starch hydrolase, as well as studying the relationship between the structure and activity of these flavonoids. They are also working to expand the scope of the food-grade synthetic reaction to synthesize oligomers of other polyphenolic compounds.
“We welcome cooperation with interested partners in studying the bioactivities of bi- and tri-flavones. Our team believes that the unique library of bi- and tri-flavones will help promote human health and prevent disease,” Professor Huang added.
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