Highly Efficient and Enzymatic Regioselective Undecylenoylation of Gastrodin in 2-Methyltetrahydrofuran-Containing Systems

Abstract

Highly efficient and regioselective acylation of pharmacologically interesting gastrodin with vinyl undecylenic acid has been firstly performed through an enzymatic approach. The highest catalytic activity and regioselectivity towards the acylation of 7′-hydroxyl of gastrodin was obtained with Pseudomonas cepacia lipase. In addition, it was observed the lipase displayed higher activity in the eco-friendly solvent 2-methyltetrahydrofuran-containing systems than in other organic solvents. In the co-solvent mixture of tetrahydrofuran and 2-methyltetrahydrofuran (3/1, v/v), the reaction rate was 60.6 mM/h, substrate conversion exceeded 99%, and 7′-regioselectivity was 93%. It was also interesting that the lipase-catalyzed acylation couldn’t be influenced by the benzylic alcohol in gastrodin. However, pseudomonas cepacia lipase displayed different regioselectivity towards gastrodin and arbutin.

Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives

“…Their applications range from oleochemistry (Abdelmoez and Mustafa, 2014;Hama and Noda, 2018), detergent (Jurado et al, 2011;Soleimani et al, 2017) and food industries (Ferreira-Dias et al, 2013), to the preparation of chiral intermediates (de Miranda, 2015;Seddigi et al, 2017). Relevant to the scope of this work, lipases were also demonstrated to perform regioselective acylation (Lee et al, 2019;Wang et al, 2018;Yang et al, 2014) as well as hydrolysis (Carey and McCann, 2019). As a catalyst of choice for the esterification of marchantin A, Novozym® 40086 was selected.…”

Acute embryo toxicity and teratogenicity of three potential biofuels also used as flavor or solvent

“…Beside their promising potential as biofuels, they can also be used as (co-)solvents (Shanmuganathan et al, 2010;Winter, 2010;Geilen et al, 2011;Yang et al, 2014) and EL also as flavor in food (The Good Scents Company, 2015). EL is used as a solvent for cellulose acetate, starch and flavorings (Winter, 2010) and 2-MTHF is a promising candidate to substitute petrochemical solvents in industrial processes (Shanmuganathan et al, 2010;Geilen et al, 2011).…”