Semi-preparative separation of dihydromyricetin enantiomers by supercritical fluid chromatography and determination of anti-inflammatory activities

Lin, Yuemei; Fan, Jun; Ruan, Lifang; Bi, Jingjie; Yan, Yilun; Wang, Tai; Gao, Hao; Yao, Xin‐Sheng; Cheng, Kui; Zhang, Weiguang

doi:10.1016/j.chroma.2019.460386

Cited by 18 publications

(11 citation statements)

References 30 publications

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“…Similar to other flavonoids, DHM has received great attention due to its pharmacological characteristics, such as antioxidant, antitumor, , memory amelioration, hepatoprotective, , and neuroprotective effects, emphasizing its importance in food, health, and medical industry applications . Some products related to DHM have been made; for example, health products using DHM as the main active ingredient are popular in the US market due to its function of relieving dry drunk syndrome. , Traditional extraction is being gradually replaced because of its growing demand in the market. Hence, an efficient and economical DHM production method is necessary.…”

Section: Introductionmentioning

confidence: 99%

“…Some researchers also tried using nonenzymatic and enzymatic methods to produce target flavonoids based on the chemical reaction or cell cultures and crude enzyme extraction from callus, which proved to be inefficient . Traditionally, DHM is mainly extracted from Ampelopsis grossedentata, some technologies have been developed for the extraction and separation of DHM, such as supercritical fluid chromatography and high-speed countercurrent chromatography, and approximately 3 g of DHM can be extracted from 1 kg of dry weight plant . However, in addition to complex separation processes, massive biomass is required by plant extraction, which means taking up a lot of land resources and time.…”

Section: Introductionmentioning

confidence: 99%

“…8 Some products related to DHM have been made; for example, health products using DHM as the main active ingredient are popular in the US market due to its function of relieving dry drunk syndrome. 9,10 Traditional extraction is being gradually replaced because of its growing demand in the market. Hence, an efficient and economical DHM production method is necessary.…”

Section: Introductionmentioning

confidence: 99%

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Enhanced Biosynthesis of Dihydromyricetin in Saccharomyces cerevisiae by Coexpression of Multiple Hydroxylases

Lyu

et al. 2020

J. Agric. Food Chem.

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Dihydromyricetin (DHM) is a traditional plant-extracted flavonoid with some health benefits. This study aimed to metabolically engineer the strains for DHM bioproduction. Two strains of BK-11 and BQ-21 were integrated with flavonoid 3hydroxylase (F3H) or both F3H and flavonoid 3′-hydroxylase (F3′H). The resulting strains have expressed the enzymes of GmCPR and SlF3′5′H, and then, the promoters of INO1p and TDH1p were used to enhance further the DHM production from naringenin in Saccharomyces cerevisiae. Through multiple-copy integration, 709.6 mg/L DHM was obtained by adding 2.5 g/L naringenin in a 5 L bioreactor, implying that the synergistic effect between F3′H and flavonoid 3′5′-hydroxylase is likely to promote the DHM production. An yield of 246.4 mg/L DHM was obtained from glucose by deleting genes for branch pathways and integrating PhCHS, MsCHI, Pc4CL, and FjTAL. To our knowledge, this is the highest production reported for the de novo biosynthesis of DHM.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Enhanced Biosynthesis of Dihydromyricetin in Saccharomyces cerevisiae by Coexpression of Multiple Hydroxylases

Lyu

et al. 2020

J. Agric. Food Chem.

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“…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.…”

Section: Chiral Separationmentioning

confidence: 99%

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

Zhang

Caprioli²,

Hussain

et al. 2021

eFood

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Natural bioactive compounds present a better alternative to prevent and treat chronic diseases owing to their lower toxicity and abundant resources. (+)-Dihydromyricetin (DMY) is a flavanonol, possessing numerous interesting bioactivities with abundant resources. This review provides a comprehensive overview of the recent advances in DMY natural resources, stereoisomerism, physicochemical properties, extraction, biosynthesis, pharmacokinetics, and biotransformation. Stereoisomerism of DMY should be considered for better indication of its efficacy. Biotechnological approach presents a potential tool for the production of DMY using microbial cell factories. DMY high instability is related to its powerful antioxidant capacity due to pyrogallol moiety in ring B, and whether preparation of other analogues could demonstrate improved properties. DMY demonstrates poor bioavailability based on its low solubility and permeability with several attempts to improve its pharmacokinetics and efficacy. DMY possesses various pharmacological effects, which have been proven by many in vitro and in vivo experiments, while clinical trials are rather scarce, with underlying action mechanisms remaining unclear. Consequently, to maximize the usefulness of DMY in nutraceuticals, improvement in bioavailability, and better understanding of its actions mechanisms and drug interactions ought to be examined in the future along with more clinical evidence.

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“…Chiral recognition and its interaction among other molecules is a significant step in natural biological processes. A recent development for enantiomers has highlighted the impact of specific stereochemistry of enantiomers and its configuration difference (due to repulsive forces between overlapping electron clouds) on the biological, metabolic, pharmacological, and toxicological activities in vitro and vivo (Lin et al., 2019; Zhou, Yu, & Zeng, 2014). It is also reported that enantiopure could play an essential role in drug discovery due to its effective biological compound coordination with receptor molecules, which can result in the desired effect with fewer side effects and more efficacious (Pinto et al, , 2020).…”

Section: Introductionmentioning

confidence: 99%

Chirality of the biomolecules enhanced its stereospecific action of dihydromyricetin enantiomers

Umair

Jabbar

Sultana

et al. 2020

Food Science & Nutrition

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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.

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Semi-preparative separation of dihydromyricetin enantiomers by supercritical fluid chromatography and determination of anti-inflammatory activities

Cited by 18 publications

References 30 publications

Enhanced Biosynthesis of Dihydromyricetin in Saccharomyces cerevisiae by Coexpression of Multiple Hydroxylases

Enhanced Biosynthesis of Dihydromyricetin in Saccharomyces cerevisiae by Coexpression of Multiple Hydroxylases

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

Chirality of the biomolecules enhanced its stereospecific action of dihydromyricetin enantiomers

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