Lipase-catalyzed synthesis of laurate esters from puerarin and its β-D-fructofuranosyl-(2→6)-puerarin derivative

Abstract

This study investigates the transesterification of isoflavones puerarin and β-D-fructofuranosyl-(2→6)-puerarin to enhance their lipophilicity for specific pharmacological applications. The process achieved high yields (80-100%) in the isoflavones conversion when commercial lipases from Candida antarctica (CALB) and Thermomyces lanuginosus (TL IM) were used. The acylation patterns between CALB and TL IM varied depending on the substrate; both enzymes yielded principally monoacylated products from puerarin and β-D-fructofuranosyl-(2→6)-puerarin. However, TL IM also produced di- and triacylated derivatives of β-D-fructofuranosyl-(2→6)-puerarin in substantial amounts. Structural characterization by NMR identified puerarin-6ʹʹ-O-laurate and β-D-fructofuranosyl-(2→6)-puerarin-6ʹʹʹ-O-laurate as the primary products in CALB and TL IM reactions. These acyl derivatives presented improved lipophilicity (Log P from −1.0 − 0.16 to 3.26 − 3.58) and antioxidant activity (67.2-97.3 to 102.5-131.4 µM TE/mmol). Therefore, these compounds have potential pharmacological applications.

Keywords:

• Acylation
• lipase
• isoflavone
• puerarin
• β-D-fructofuranosyl-(2→6)-puerarin
• vinyl laurate

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

Thanks for the financial support of CONACYT (Mexico) through the Ph.D. scholarship 268290 for ACV. This work was supported in Mexico by the CONACYT project CONACYT-SENER 250014. In Spain, this work was supported by the Spanish Ministry of Science and Innovation (Grant PID2019-105838RB-C31 and PDC2022-133134-C21).