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Taxifolin stability: In silico prediction and in vitro degradation with HPLC-UV/UPLCe ESI-MS monitoring

Journal of Pharmaceutical Analysis 2021年第2期11卷 232-240页

作者： Fernanda Cristina Stenger Moura Carmem Lúciados Santos Machado Favero Reisdorfer Paula Angelica Garcia Couto Maurizio Ricci Valdir Cechinel-Filho Tiago J.Bonomini Louis P.Sandjo Tania Mari Belle Bresolin Pharmaceutical Sciences Graduate Program School of Health SciencesCourse of PharmacyUniversidade do Vale do ItajaíItajaíSC88302-202Brazil Laboratory of Research and Development of Drugs Pharmaceutical Sciences Graduate ProgramSchool of Health SciencesCourse of PharmacyUniversidade Federal do PampaUruguaianaRS97500-970Brazil Department of Pharmaceutical Science Universita degli Studi di PerugiaPerugiaPG06123Italy Chemistry Department Universidade Federal de Santa CatarinaTrindadeFlorian opolisSC88040-900Brazil

Taxifolin has a plethora of therapeutic activities and is currently isolated from the stem bark of the tree Larix gmelinni(Dahurian larch). It is a flavonoid of high commercial interest for its use in supplements or in antioxidant-rich functional foods. However, its poor stability and low bioavailability hinder the use of flavonoid in nutritional or pharmaceutical formulations. In this work, taxifolin isolated from the seeds of Mimusops balata, was evaluated by in silico stability prediction studies and in vitro forced degradation studies(acid and alkaline hydrolysis, oxidation, visible/UV radiation, dry/humid heating) monitored by high performance liquid chromatography with ultraviolet detection(HPLC-UV) and ultrahigh performance liquid chromatography-electrospray ionization-mass spectrometry(UPLC-ESI-MS). The in silico stability prediction studies indicated the most susceptible regions in the molecule to nucleophilic and electrophilic attacks, as well as the sites susceptible to oxidation. The in vitro forced degradation tests were in agreement with the in silico stability prediction, indicating that taxifolin is extremely unstable(class 1) under alkaline hydrolysis. In addition, taxifolin thermal degradation was increased by *** the other hand, with respect to photosensitivity, taxifolin can be classified as class 4(stable).Moreover, the alkaline degradation products were characterized by UPLC-ESI-MS/MS as dimers of taxifolin. These results enabled an understanding of the intrinsic lability of taxifolin, contributing to the development of stability-indicating methods, and of appropriate drug release systems, with the aims of preserving its stability and improving its bioavailability.

关键词： Dihydroquercetin in silico stability prediction Forced degradation

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