Physicochemical properties of dihydromyricetin and the effects of ascorbic acid on its stability and bioavailability

Abstract

BACKGROUND Dihydromyricetin (DMY) is a natural dihydroflavonol with many bioactive effects. However, the physicochemical properties of DMY related to its bioavailability, especially its stability, are unclear. RESULTS The effects of pH, temperature, metal ions and ascorbic acid (AA) on the stability of DMY were studied using high‐performance liquid chromatography (HPLC). The bioavailability of DMY in the presence and absence of AA was compared. Dihydromyricetin was unstable in weak alkaline solutions, and the degradation was significantly accelerated in the presence of Cu2+ and Fe3+. The degradation process followed the first‐order kinetic model. The degradation rate constant (k) increased with increasing pH and temperature. The remaining DMY was only 49% of its initial concnentration after 4 h in simulated intestinal fluid (SIF) at 37 °C. However, by supplementing with AA, the degradation of DMY was rarely occured within 6 h. The solubility of DMY at pH 3–5 was about 750 μg mL−1, slightly increasing to 853 μg mL−1 at pH 6. Pharmacokinetic studies showed that the bioavailability of DMY increased from 0.122% to 0.341% by supplementing with AA (10% of DMY). CONCLUSION The degradation of DMY is one reason for its poor bioavailability. The presence of AA could significantly improve the stability of DMY, and further improve its bioavailability in rats. © 2020 Society of Chemical Industry

Mechanism of Dihydromyricetin on Inflammatory Diseases

“…In addition, DHM improved pyroptosis caused by NLRP-3 in chronic liver injury mice ( Cheng et al, 2020 ). DHM significantly inhibited cholesterol accumulation and foam cell formation, improved mitochondrial function, reduced oxidative stress as well as reduced the activation of NLRP3 in oxidized low-density lipoprotein (ox-LDL)-stimulated macrophages in Sirtuin3 (SIRT3) ko mice ( Sun et al, 2021 ). Studies have shown that NLRP-3 activation contributed to the development of cardiotoxicity.…”

A multifaceted review on dihydromyricetin resources, extraction, bioavailability, biotransformation, bioactivities, and food applications with future perspectives to maximize its value

“…DMY is a white needle-like crystal obtained from ethanol with very poor water-solubility and stability as well as powerful antioxidative activity [19]. DMY with 2-phenylchromogenone as the core structure belongs to the class IV based on the biopharmaceutical classification system (BCS) due to its low solubility and permeability [7].…”

“…DMY is highly unstable in solution and to degrade rapidly by decomposition and isomerization of DMY induced by the chiral inversion [16] . Furthermore, other factors affecting the stability of DMY include pH, temperature, metal ions, interaction with macromolecules and other components [7,25]. Among these factors, pH plays a critical role in the stability of DMY.…”

“…Likewise, DMY was also found to be rapidly degraded in DMEM supplemented with 10% fetal bovine serum at 37 • C, forming possible dimers of DMY, oxidation products, ring-cleavage products and isomers. Therefore, to improve the stability of DMY and avoid the artificial results in cell culture experiments, a few methods including low temperature and adding ascorbic acid were used [7,25].…”

LC‐ESI‐QTOF/MS characterization of antimicrobial compounds with their action mode extracted from vine tea (Ampelopsis grossedentata) leaves

“…Recent works have focused on various functional aspects of dihydromyricetin, such as antimicrobial properties (Cui, Li, et al., 2021; Wu et al., 2017; Xiao et al., 2019), antioxidant capacity (Xie et al., 2019), flavor infusion (Carneiro et al., 2020), stability and stereo‐specific action (Umair et al., 2020), pharmacological activities (Muhammad et al., 2018), the bioavailability of bioactive compounds (Sun et al., 2021), interaction with iron (Wang et al., 2020), and its optimized extraction (Muhammad et al., 2017) by using response surface methodology. The proposed antimicrobial mechanism of dihydromyricetin in previous reports (Farhadi et al., 2019; Liang et al., 2020; Shevelev et al., 2020; Zhang et al., 2018) is comprises on; the membrane permeability, functional changes in the cell membrane, cytoplasmic membrane damage, blockage in the energy metabolism, retardation in the nucleic acid synthesis process, porin inhibition on the cell membrane, and weakening of the pathogenicity (Farhadi et al., 2019; Xie et al., 2019; Xie et al., 2015).…”