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.
Highlights
Gastrodin, namely p-hydroxymethy-lphenyl-b-D-glucopyranoside (Figure 1), is one of the major active ingredient obtained from Gastrodia elata Blume with extensive pharmacological activities
We previously investigated the enzymatic regioselective acylation of arbutin (Figure 1), whose chemical structure is same as gastrodin except for benzylic alcohol
Gastrodin and undecylenic acid vinyl ester were from TCI, Japan
Summary
Namely p-hydroxymethy-lphenyl-b-D-glucopyranoside (Figure 1), is one of the major active ingredient obtained from Gastrodia elata Blume with extensive pharmacological activities. It has been clinically used due to its sedative, hypnotic, anticonvulsion and neuroprotective effect, while no side effects and toxicities in patients have been observed so far [1,2]. Gastrodin usually suffers from low oral bioavailability because it is difficult to penetrate cell membrane. It has been demonstrated that glucoside ester compounds could be good glyco-drugs [3] and improve bioavailablity of some drugs [4]. Gastrodin bioavailability might be enhanced significantly by acylation with the fatty acid. It was reported that some gastrodin analogues bearing lipophilic groups in glycosyl moiety had higher antiinfluenza activities [5], presumably due to their improved membrane penetration
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