Chirality of the biomolecules enhanced its stereospecific action of dihydromyricetin enantiomers

Abstract

The present study explores the effect of chirality of the biological macromolecules, its functional aspects, and its interaction with other food components. Dihydromyricetin (DHM) is a natural novel flavonol isolated from the vine tea (Ampelopsis grossedentata) leaves. However, limited progress in enantiopure separation methods of such compounds hinder in the development of enantiopure functional studies. This study is an attempt to develop a simple, accurate, and sensitive extraction method for the separation of the enantiopure DHM from vine tea leaves. In addition, the identification and purity of the extracted enantiopure (−)‐DHM were further determined by the proton nuclear magnetic resonance (1H‐NMR) and the carbon nuclear magnetic resonance (13C‐NMR). The study further evaluates the antimicrobial activity of isolated (‐)‐DHM in comparison with racemate (+)‐DHM, against selected foodborne pathogens, whereas the action mode of enantiopure (−)‐DHM to increase the integrity and permeability of the bacterial cell membrane was visualized by confocal laser scanning microscopy using green fluorescence nucleic acid dye (SYTO‐9) and propidium iodide (PI). Moreover, the morphological changes in the bacterial cell structure were observed through field emission scanning electron microscope. During analyzing the cell morphology of B. cereus (AS11846), it was confirmed that enantiopure (−)‐DHM could increase the cell permeability that leads to the released of internal cell constituents and, thus, causes cell death. Therefore, the present study provides an insight into the advancement of enantiopure isolation along with its antimicrobial effect which could be served as an effective approach of biosafety.

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

“…The (+) DMY and (±) DMY in solidstate were distinguished using spectroscopic analyses, i.e., 1 H NMR and chiral HPLC [16]. Several separation and purification methods reported include high-speed countercurrent chromatography [48,49], supercritical fluid chromatography [50], recrystallization [17] found successful to yield homochiral DMY.…”

“…For extraction, separation and purification of DMY from A. grossedentata leaves, several methods including reflux, ultrasound, microwave, supercritical fluid chromatography, high‐speed countercurrent chromatography, crystallization and microporous resin adsorption are commonly used alone or in combination. Whereas, for structural identification of DMY, proton nuclear magnetic resonance ( 1 H‐NMR), single‐crystal X‐ray diffraction (XRD), infrared radiation, UV‐Vis spectrum and Fourier‐transform infrared spectroscopy are used [13, 17, 38]. Identification of exact stereoisomer should be determined using techniques, such as chiral column chromatography and circular dichroism.…”

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

“…Previous research has shown that hydroxylation at the fifth and seventh sites is important for flavonol antibacterial activity against bacteria (Echeverría et al., 2017; Umair et al., 2020; Zapadka et al., 2019). Furthermore, another study examined the link between flavonoid structure and antibacterial properties, finding a similar hydroxylation site to be associated with antimicrobial activity (Farhadi et al., 2019) and antibiotic resistance (Abdelgader et al., 2018).…”

“…It has been shown that 2R, 3R‐dihydromyricetin (DHM), a flavonoid isolated from vine tea, had good inhibitory action against S. aureus (Umair et al., 2020). In terms of the structure–activity connection of flavonoids, very little research has been conducted on the role of the C‐ring in antibacterial activity (Cushnie & Lamb, 2011).…”

“…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).…”