Abstract
Enzymatic conjugation with fatty acids including omega-3 polyunsaturated fatty acids (ω-3 PUFAs) derived from fish oil to three citrus fruit-derived flavonoids: grapefruit extract, naringin, and neohesperidin dihydrochalcone were investigated. The conversions were achieved over 85% under the catalysis of lipase Novozyme 435 in acetone at 45°C at semi-preparative scale. The conjugates were purified via solvent partition and silica gel chromatography and achieved 90–98% in purity. The NMR analysis of the conjugates confirmed that the fatty acid carbon chain was linked onto the primary –OH group on the glucose moiety of the flavonoids. The purified flavonoid conjugates alongside their original flavonoids were analyzed for antioxidant activities via 2,2-diphenyl-1-picrylhydrazyl scavenging assay, and anti-peroxidation test via peroxide values measured during a 1-week fish oil storage trial. Vascular endothelial growth factor (VEGF) assay was conducted with 1, 10, and 100 μM of naringin and grapefruits and their conjugates, respectively, and total VEGF levels were measured at 24 and 48 h, respectively, using ELISA and dot blot analysis. The results from these functionality experiments demonstrated that flavonoid FA conjugates have at least comparable (if not higher) antioxidant activity, anti-peroxidation activity, and anti-angiogenic activity.
Highlights
Bioactive natural compounds are produced in plants and animals for various metabolic purposes and have been consumed as functional foods or used in indigenous medicine throughout human civilization
These extracts, might be restricted to the variety of applications, due to unsuitable physical properties in the downstream product development phase, i.e., polyunsaturated fatty acids (PUFAs) is sensitive to heat and has limited shelf life due to prone to oxidation; flavonoids have moderate polarity and propensity to interact with biological materials (Hidari et al, 2009; Dasilva et al, 2017)
This study aimed to attach selected individual fatty acids and a omega-3 (ω-3) PUFA rich mixture of fatty acids derived from fish oil to three citrus fruit-derived flavonoids: grapefruit extract, naringin, and Neohesperidin dihydrochalcone (NHDC), under lipase catalysis
Summary
Bioactive natural compounds are produced in plants and animals for various metabolic purposes and have been consumed as functional foods or used in indigenous medicine throughout human civilization Among these bioactives, flavonoids and polyunsaturated fatty acids (PUFAs) are two groups of compounds that have attracted worldwide scientific interest in the past 30 years. Natural sources that are rich in flavonoids and PUFA have been (or have the potential to be) utilized as bioactive ingredients in nutraceutical and pharmaceutical products These extracts, might be restricted to the variety of applications, due to unsuitable physical properties in the downstream product development phase, i.e., PUFA is sensitive to heat and has limited shelf life due to prone to oxidation; flavonoids have moderate polarity and propensity to interact with biological materials (Hidari et al, 2009; Dasilva et al, 2017). Post extraction modification, aiming to overcome the limitations of the natural extracts, is an option for maximizing their applications
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