The Bioavailability, Extraction, Biosynthesis and Distribution of Natural Dihydrochalcone: Phloridzin

Tian, Lei; Cao, Jun; Zhao, Ting; Liu, Yaping; Khan, Afsar; Cheng, Guiguang

doi:10.3390/ijms22020962

Cited by 54 publications

(35 citation statements)

References 106 publications

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“…From natural sources, dihydrochalcones are isolated as aglycones and their glycosides.Most extensively described dihydrochalcones are phloretin and its 2 -O-glucoside named phloridzin, isolated from a genus of small trees and shrubs Malus. Many studies proved numerous biological activities of phloridzin, such as anti-diabetic, anti-inflammatory, anti-oxidant, antihyperglycemic, antimicrobial, cardio-and hepatoprotective, anti-obesity and others [18][19][20][21][22]. Similar activities have been reported for phloretin [23].…”

Section: Introductionsupporting

confidence: 55%

New Glycosylated Dihydrochalcones Obtained by Biotransformation of 2′-Hydroxy-2-methylchalcone in Cultures of Entomopathogenic Filamentous Fungi

Krawczyk-Łebek

Dymarska

Janeczko

et al. 2021

IJMS

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Flavonoids, including chalcones, are more stable and bioavailable in the form of glycosylated and methylated derivatives. The combined chemical and biotechnological methods can be applied to obtain such compounds. In the present study, 2′-hydroxy-2-methylchalcone was synthesized and biotransformed in the cultures of entomopathogenic filamentous fungi Beauveria bassiana KCH J1.5, Isaria fumosorosea KCH J2 and Isaria farinosa KCH J2.6, which have been known for their extensive enzymatic system and ability to perform glycosylation of flavonoids. As a result, five new glycosylated dihydrochalcones were obtained. Biotransformation of 2′-hydroxy-2-methylchalcone by B. bassiana KCH J1.5 resulted in four glycosylated dihydrochalcones: 2′-hydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside, 2′,3-dihydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside, 2′-hydroxy-2-hydroxymethyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside, and 2′,4-dihydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside. In the culture of I. fumosorosea KCH J2 only one product was formed—3-hydroxy-2-methyldihydrochalcone 2′-O-β-d-(4″-O-methyl)-glucopyranoside. Biotransformation performed by I. farinosa KCH J2.6 resulted in the formation of two products: 2′-hydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside and 2′,3-dihydroxy-2-methyldihydrochalcone 3′-O-β-d-(4″-O-methyl)-glucopyranoside. The structures of all obtained products were established based on the NMR spectroscopy. All products mentioned above may be used in further studies as potentially bioactive compounds with improved stability and bioavailability. These compounds can be considered as flavor enhancers and potential sweeteners.

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Section: Introductionsupporting

confidence: 55%

New Glycosylated Dihydrochalcones Obtained by Biotransformation of 2′-Hydroxy-2-methylchalcone in Cultures of Entomopathogenic Filamentous Fungi

Krawczyk-Łebek

Dymarska

Janeczko

et al. 2021

IJMS

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“…Although the DHCs could be found in flesh and peel, the highest concentration is located in the seeds, ranging from 24.1 to 86.4 mg/100 g FW [ 8 ]. Numerous studies have shown that both phloridzin and phloretin exert antibacterial, anti-inflammatory, antihyperglycemic, anti-diabetic and anticancer activities, and cardioprotective, neuroprotective hepatoprotective, and immunomodulatory properties [ 81 , 82 , 83 ].…”

Section: Effects Of Processing and Storage Conditions On The Stability Of Polyphenolsmentioning

confidence: 99%

High–Pressure Processing vs. Thermal Treatment: Effect on the Stability of Polyphenols in Strawberry and Apple Products

Salazar-Orbea

Garcı́a-Villalba

Tomás-Barberán

et al. 2021

Foods

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Polyphenols are important bioactive compounds that are affected by processing. The consumer’s demand for minimally processed products contributes to the increase in non-thermal technologies such as high-pressure processing (HPP) in the food industry. This review is aimed at critically discussing the positive and negative effects of thermal treatment (TT) and HPP on the stability of different polyphenol families in agro-food products obtained from strawberry and apple, two of the most used fruits in food processing. Our findings show that the phenolic content was affected by processing, fruit type, polyphenol family, and storage conditions (time and temperature) of the final product. To increase shelf life, manufacturers aiming to preserve the natural content of polyphenols need to find the sweet spot between polyphenol stability and product shelf-life since the residual enzyme activity from HPP can affect polyphenols negatively.

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“…Phlorizin is a natural dihydrochalcone found in a number of fruitful trees, mainly the Malus genus. It produces renal glycosuria and blocks intestinal and renal glucose reabsorption by inhibiting the sodium-glucose symporters located there [ 11 , 12 ]. Recently, ertugliflozin arrived as the newest synthetic GLT-2 (glucose transporter-2) inhibitor to receive FDA approval for the treatment of diabetes [ 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

Plants Secondary Metabolites as Blood Glucose-Lowering Molecules

2021

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Recently, significant advances in modern medicine and therapeutic agents have been achieved. However, the search for effective antidiabetic drugs is continuous and challenging. Over the past decades, there has been an increasing body of literature related to the effects of secondary metabolites from botanical sources on diabetes. Plants-derived metabolites including alkaloids, phenols, anthocyanins, flavonoids, stilbenoids, saponins, tannins, polysaccharides, coumarins, and terpenes can target cellular and molecular mechanisms involved in carbohydrate metabolism. In addition, they can grant protection to pancreatic beta cells from damage, repairing abnormal insulin signaling, minimizing oxidative stress and inflammation, activating AMP-activated protein kinase (AMPK), and inhibiting carbohydrate digestion and absorption. Studies have highlighted many bioactive naturally occurring plants’ secondary metabolites as candidates against diabetes. This review summarizes the current knowledge compiled from the latest studies published during the past decade on the mechanism-based action of plants-derived secondary metabolites that can target various metabolic pathways in humans against diabetes. It is worth mentioning that the compiled data in this review will provide a guide for researchers in the field, to develop candidates into environment-friendly effective, yet safe antidiabetics.

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The Bioavailability, Extraction, Biosynthesis and Distribution of Natural Dihydrochalcone: Phloridzin

Cited by 54 publications

References 106 publications

New Glycosylated Dihydrochalcones Obtained by Biotransformation of 2′-Hydroxy-2-methylchalcone in Cultures of Entomopathogenic Filamentous Fungi

New Glycosylated Dihydrochalcones Obtained by Biotransformation of 2′-Hydroxy-2-methylchalcone in Cultures of Entomopathogenic Filamentous Fungi

High–Pressure Processing vs. Thermal Treatment: Effect on the Stability of Polyphenols in Strawberry and Apple Products

Plants Secondary Metabolites as Blood Glucose-Lowering Molecules

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