Esterification of Lutein from Japanese Knotweed Waste Gives a Range of Lutein Diester Products with Unique Chemical Stability.

A valorization strategy for an aggravating type of plant waste is put to the test herein. It envisions the use of Japanese knotweed green leaves as a sustainable source of free lutein, from which bioactive diesters could be prepared as potential value-added products with improved properties. To this end, 13 structurally distinct model lutein diesters were synthesized and the relationships between their structure and stability were systematically determined. The forced degradation data show that the stability of a particular lutein diester may depend to a large extent on the type of exposure (elevated temperature, light, oxidant, or acidic environment) and, more importantly, not every esterification attempt necessarily leads to an enhancement of lutein's chemical stability. However, three branched and bulky products-lutein di(2,2-dimethylpropanoate), lutein di(2-methylpropanoate), and lutein di(3-methylbutanoate)-proved to be particularly relevant, as they consistently exhibited 1.5-21-fold higher stability compared to free lutein, regardless of the stress conditions used. Finally, we show that the Japanese knotweed plant matrix had a significant negative or positive effect on pigment degradation kinetics that could not be easily predicted. Thus, the proposed valorization strategy is quite feasible, but the esterification approach should be tailored to the intended use of a lutein diester.