Screening of potent α‐glucosidase inhibitory and antioxidant polyphenols in Prunella vulgaris L. by bioreaction–HPLC–quadrupole‐time‐of‐flight‐MS/MS and in silico analysis

Abstract

Prunella vulgaris L. is a well-known traditional Chinese medicine for blood glucose homeostasis and antioxidant potential. Ethyl acetate fraction of P. vulgaris L. demonstrated higher phenolic content (85.53 ± 6.74 mg gallic acid equivalents per gram dry weight), α-glucosidase inhibitory (IC 50 , 69.13 ± 2.86 μg/ml), and antioxidant (IC 50 , 8.68 ± 1.01 μg/ml) activities. However, the bioactive polyphenols responsible for the beneficial properties remain unclear.Here, bioreaction-HPLC-quadrupole-time-of-flight-MS/MS method was developed for rapid, accurate, and efficient screening and identification of polyphenols with α-glucosidase inhibitory and antioxidant activities from P. vulgaris L.Bioactive polyphenols can specifically bind with α-glucosidase or react with 1,1-diphenyl-2-picryl-hydrazyl radical, which was easily discriminated from nonactive compounds. Subsequently, 20 bioactive polyphenols (16 phenyl propionic acid derivatives and four flavonoids) were screened and identified. Furthermore, molecular docking analysis revealed that screened 20 polyphenols bind with the active sites of α-glucosidase through hydrogen bonding and π-π stacking. Density functional theory calculations demonstrated their electron transport ability and chemical reactivity. The in silico analysis confirmed the screened results. In summary, this study provided a valuable strategy for rapid discovering bioactive compounds from complex natural products and offered scientific evidence for further development and application of P. vulgaris L.

Analysis of the phytochemical components of Prunella vulgaris using high‐performance liquid chromatography quadrupole time‐of‐flight mass spectrometry combined with molecular networking and assessment of their antioxidant and anti‐α‐glucosidase activities

“…This difference may be associated with the growing conditions of P. vulgaris . The observed TPC values of P. vulgaris are consistent with those of previous findings (Cheng et al, 2022), showing that the ethyl acetate fraction of P. vulgaris had the highest TPC (85.53 ± 6.74 mg GAE/g DW).…”

“…The flavonoids present in P. vulgaris are thus able to inhibit α ‐glucosidase activity. However, studies have reported α ‐glucosidase inhibition by caffeic acid in P. vulgaris , shown by molecular docking and bioreaction ultrafiltration, as well as in alloxan‐induced diabetic mice (Cheng et al, 2022; Raafat et al, 2016).…”

Elution–extrusion counter‐current chromatographic separation and theoretical mechanism of antioxidant from Robinia pseudoacacia flower

“…The FMO theory subdivided the electron distributed around the kaempferol molecule into molecular orbitals with different energy levels, among which the HOMO ( E HOMO = −5.7579 eV) and LUMO ( E LUMO = −1.8939 eV) were mainly studied (Figure 4). The energy gap was 3.8640 eV, indicating the reaction may occur to some extent [42–44]. The small E gap was more favorable for the reaction.…”

Advances of responsive deep eutectic solvents and application in extraction and separation of bioactive compounds

“…Huber et al evaluated the molecular interactions between NADES and the sample by combining COSMO-RS and NMR experiments. 1 H NMR and NOESY spectra further showed that nonspecific and targeted intermolecular interactions were the driving force for the effective solubility enhancement of curcumin [99] the extraction is mainly contributed by hydrophobic interactions. The possible extraction mechanism of TRDES by density functional theory (DFT) calculation was proposed [84].…”

“…Bioactive compounds are physiologically active components that have regulatory functions such as antibacterial, antioxidant, anti-inflammatory, and anti-cancer activity [1][2][3]. Some extraction and separation techniques, such as liquid-liquid extraction, supercritical fluid extraction, Soxhlet extraction, reflux, steam distillation, percolation, and precipitation separation, are used in extraction and separation processes [4][5][6][7].…”