Seven dihydrochalcone compounds were isolated from the leaves of Malus crabapples, cv. "Radiant", and their chemical structures were elucidated by UV, IR, ESI-MS, ¹H-NMR and (13)C-NMR analyses. These compounds, which include trilobatin (A1), phloretin (A2), 3-hydroxyphloretin (A3), phloretin rutinoside (A4), phlorizin (A5), 6''-O-coumaroyl-4'-O-glucopyranosylphloretin (A6), and 3'''-methoxy-6''...

A new phloretin derivative 1 3-[2-(4-hydroxy-phenyl)-ethyl]-benzo[d] isoxazole-4,6-diol (yield 63%) was synthesized from by carbonyl nucleophilic addition condensation reaction. Its structure characterized 1H NMR, 13C NMR and HR-MS. The phloretin, compound 1, resveratrol acetylated were determined comparing them with paclitaxel. Anti-tumor activity of alcohol on SPC-A1, EC109, A549, MCF-7 MDA-M...

In the exploration of potential therapeutic agents for rheumatoid arthritis (RA), DBA/1J mice are used as the RA model of collagen-induced arthritis (CIA). Phloretin, a flavonoid compound extracted from Prunus mandshurica, has been found to exhibit anti-inflammatory activity, making it a potential candidate for treatment of RA. The objective of this study was to evaluate the therapeutic effects...

An increase in the prevalence of the drug-resistant Mycobacteria tuberculosis necessitates developing new types of anti-tuberculosis drugs. Here, we found that phloretin, a naturally-occurring flavonoid, has anti-mycobacterial effects on H37Rv, multi-drug-, and extensively drug-resistant clinical isolates, with minimum inhibitory concentrations of 182 and 364 μM, respectively. Since Mycobacteri...

The phenolic compound phloretin is a prominent member of the chemical class of dihydrochalcones. Phloretin is specifically found in apple and apple juice and known for its biological properties. We were particularly interested in its potential dermo-cosmetic applications. However, practical limitations of phloretin do exist due to its poor water-solubility. Phloretin was sulfonated with sulfuri...

The submillisecond kinetics for phloretin binding to unilamellar phosphatidylcholine (PC) vesicles was investigated using the temperature-jump technique. Spectrophotometric studies of the equilibrium binding performed at 328 nm demonstrated that phloretin binds to a single set of independent, equivalent sites on the vesicle with a dissociation constant of 8.0 microM and a lipid/site ratio of 4....

Phloretin [3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan1-one] is a hydrophobic, dihydrochalcone, polyphenolic compound (MW 274.3 g/mol, XlogP 2.6) that has been identified in apples and other natural sources including Pieris japonica, Kalmia latifolia, Hoveniae Lignum, and Loiseleuria procumbens [1-6] (Figure 1). Phloridzin is the glycoside of phloretin (phloretin-2’-glucose) which has ...

Glycosylation of polyphenols may increase their aqueous solubility, stability, bioavailability and pharmacological activity. Herein, we used a mutant sucrose phosphorylase from Thermoanaerobacterium thermosaccharolyticum engineered to accept large (variant TtSPP_R134A) produce phloretin glucosides. The reaction was performed using 10% (v/v) acetone as cosolvent. selective formation monoglucosid...

Purpose: To evaluate the in vitro anti-proliferative activity and probable mechanism of phloretin in human gastric cancer BGC823 cell lines. Methods: Phloretin was isolated from apple tree leaves and identified by H-Nuclear Magnetic Resonance (NMR), C-NMR and electrospray ionization tandem mass spectrometry (ESI-MS). The inhibitory activity of the compound in BGC823 gastric cancer cells was det...

The antioxidant properties of two apple dihydrochalcones, namely phloretin and phloridzin, were evaluated and compared with those of alpha-tocopherol and butylated hydroxytoluene (BHT). The effects were studied in an oil-in-water emulsion system containing methyl linolenate (ML), methyl eicosapentaenoate (MEPA), and methyl docosahexaenoate (MDHA) in which oxidation was initiated by the peroxyl ...