Substituent Effects on in Vitro Antioxidizing Properties, Stability, and Solubility in Flavonoids

• Published in: Journal of agricultural and food chemistry Vol. 62; no. 15; pp. 3321 - 3333
• Main Authors: Plaza, Merichel, Pozzo, Tania, Liu, Jiayin, Gulshan Ara, Kazi Zubaida, Turner, Charlotta, Nordberg Karlsson, Eva
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 16.04.2014; American Chemical Society, Books and Journals Division
• Subjects: acylation; additives; Agricultural Science, Forestry and Fisheries; Agricultural Sciences; antioxidant; antioxidant activity; antioxidants; Antioxidants - chemistry; dietary supplements; enzyme substrates; enzymes; flavonoid; flavonoids; Flavonoids - chemistry; glycosylation; humans; Lantbruksvetenskap och veterinärmedicin; Lantbruksvetenskap, skogsbruk och fiske; methylation; Molecular Structure; Oxidation-Reduction; Solubility; stability; sulfation; antioxidant; methylation; solubility; enzymes; glycosylation; sulfation; flavonoid; acylation; stability
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf405570u

Antioxidants are widely used by humans, both as dietary supplements and as additives to different types of products. The desired properties of an antioxidant often include a balance between the antioxidizing capacity, stability, and solubility. This review focuses on flavonoids, which are naturally occurring antioxidants, and different common substituent groups on flavonoids and how these affect the properties of the molecules in vitro. Hydroxyl groups on flavonoids are both important for the antioxidizing capacity and key points for further modification resulting in O-methylation, -glycosylation, -sulfation, or -acylation. The effects of O-glycosylation and acylation are discussed as these types of substitutions have been most explored in vitro concerning antioxidizing properties as well as stability and solubility. Possibilities to control the properties by enzymatic acylation and glycosylation are also reviewed, showing that depending on the choice of enzyme and substrate, regioselective results can be obtained, introducing possibilities for more targeted production of antioxidants with predesigned properties.