Highly efficient synthesis and characterization of starch aldehyde-catechin conjugate with potent antioxidant activity

In this study, cassava starch aldehyde was functionalized with catechin through acid catalyzed condensation reaction. The structural characterization, stability and antioxidant activity of starch aldehyde-catechin conjugates were investigated. Thin layer chromatography revealed the conjugates did not contain free catechin. UV–vis spectra of the conjugates exhibited an absorption band at 280 nm, attributing to the B-ring of catechin moiety. Fourier-transform infrared and proton nuclear magnetic resonance spectroscopy demonstrated the conjugation occurred between the H–6/H–8 of catechin A-ring and the aldehyde groups of starch aldehyde. X-ray diffraction pattern indicated that the conjugates had an amorphous structure. Scanning electron microscopy showed the conjugates were fragmentary slices with rough surfaces. Notably, the conjugates were more stable than catechin in phosphate buffered saline (pH 7.4). In addition, the conjugates could not be digested in simulated saliva, gastric and small intestinal juices. The reducing power and free radical scavenging activity of starch aldehyde were remarkably elevated by conjugating with catechin. Meanwhile, the conjugates were non-cytotoxic to RAW264.7 mouse macrophage cells and possessed higher resistant starch contents than starch. Our results suggest starch aldehyde-catechin conjugates can be used as antioxidants in food industry.