The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids

Rezk, Bashir M.; Haenen, Guido R.M.M.; Vijgh, W.J.F. van der; Bast, Aalt

doi:10.1016/s0006-291x(02)00618-6

Cited by 263 publications

(196 citation statements)

References 11 publications

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“…Rezk et al reported the effect of an intramolecular hydrogen bridge on LPO inhibition for 2,4,6-trihydroxyacetophenone, phloretin, and phloroglucinol. 14) In accordance with our findings, they reported that the hydrogen bond in 2,4,6-trihydroxyacetophenone (IC 50 ; 106 mM) and phloretin (IC 50 ; 24 mM) is important for the potent LPO inhibitory activity. However, phloroglucinol (IC 50 ; 624 mM), which do not form an intramolecular hydrogen bond, had a low LPO inhibitory activity.…”

Section: Resultssupporting

confidence: 90%

Antioxidant Activity of Two Phloroglucinol Derivatives from Dryopteris crassirhizoma

Lee

et al. 2003

Biological & Pharmaceutical Bulletin

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The MeOH extracts from approximately 200 Korean plants were investigated in an ongoing search for natural products with potent antioxidant activity. Among them, the MeOH extract of the rhizome of Dryopteris crassirhizoma NAKAI (Aspidiaceae) had a significant antioxidant effect on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity. D. crassirhizoma is a pteridophyte and its rhizome is a well known Chinese crude drug, which has been used clinically in Korea, Japan, and China as a vermicide. 1) In addition, phloroglucinol derivatives (albaspidin, aspidin, flavaspidic acids, and dryocrassin) and kaempferol acetyl rhamnosides (crassirhizomosides A-C and sutchuenoside A) have been isolated from this plant source previously. 2,3) The phloroglucinol derivatives possessed antibacterial, 4) antitumor promoting, 5) nitric oxide inhibitory, 6) and anti-reverse transcriptase activities. 7) More recently, we reported the antibacterial activity of the phloroglucinol derivatives from this plant. 8) However, the antioxidant activity of the phloroglucinol derivatives isolated from D. crassirhizoma has not been reported. The aim of this study was to evaluate the antioxidant activity of the compounds isolated from D. crassirhizoma. MATERIALS AND METHODSPlant Rhizome of Dryopteris crassirhizoma was collected in Mt. Sulak, Korea in July 2002 and identified by Prof. Ki-Hwan Bae, College of Pharmacy, Chungnam National University, Korea. A voucher specimen (CNU 1011) was deposited in the herbarium of the College of Pharmacy, Chungnam National University, Korea.Isolation of Flavaspidic Acids PB (1) and AB (2) The dried rhizome (1 kg) of D. crassirhizoma was extracted with MeOH (3 l, 48 hϫ2) at room temperature and the MeOH solution was then concentrated to dryness in vacuo to afford a dark brown syrupy residue (150 g). The MeOH extract was suspended in H 2 O (1 l) and then shaken with EtOAc (1 lϫ2). The EtOAc-soluble fraction (80 g) was subjected to column chromatography on silica gel and eluted with hexane (10% acetone) and increasing amount of acetone to 80% acetone. Eight fractions (each 1 l) were collected. These fractions were tested in DPPH radical scavenging assay in vitro as a model for antioxidant activity. The fractions 5 and 6 showed antioxidant activity. A combined fraction of fractions 5 and 6 (8 g) was subjected to column chromatography on Sephadex LH-20 using MeOH to afford two compounds: flavaspidic acid PB (1, 300 mg), and flavaspidic acid AB (2, 150 mg).Flavaspidic Acid PB (1 DPPH Radical Scavenging Activity DPPH radical scavenging activity was measured according to the procedure described by Takao et al. 9) Ten microliters of each sample, dissolved in DMSO, was prepared in a 96 well plate and then 190 ml of 200 mM ethanolic DPPH solution was added. The mixture was incubated at room temperature for 30 min and the absorbance of the reaction mixture was measured at 517 nm. DPPH radical scavenging activity (%) is expressed as follows:DPPH radical scavenging activity (%)ϭ(A control ϪA sample )/A control ϫ...

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Section: Resultssupporting

confidence: 90%

Antioxidant Activity of Two Phloroglucinol Derivatives from Dryopteris crassirhizoma

Lee

et al. 2003

Biological & Pharmaceutical Bulletin

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“…Phlorizin has multiple pharmacological activities, such as anti-oxidative, estrogenic and anti-estrogenic activities, memory improvement and cardioprotective activities (8)(9)(10)(11). Reports show that phlorizin inhibits intestinal glucose uptake and renal glucose reabsorption by inhibiting the sodium D-glucose cotransporter (10,12).…”

Section: Introductionmentioning

confidence: 99%

Quantitative proteomics study on the protective mechanism of phlorizin on hepatic damage in diabetic db/db mice

Gao

2012

Mol Med Report

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Abstract. Although phlorizin has been used in the treatment of diabetes mellitus for over 100 years, the underlying molecular mechanisms have not been fully elucidated. This study investigated the effect of phlorizin on body weight, blood glucose, blood triglycerides (TG), blood total cholesterol (TC), as well as overall changes in protein expression in db/db diabetic mouse liver. Phlorizin significantly decreased body weight gain and the levels of glucose, TC and TG in blood. Isobaric tag for relative and absolute quantitation (iTRAQ) quantitative proteomics profiling revealed that phlorizin interfered with the processes of carbohydrate metabolism, fatty acid biosynthesis and β-oxidation, cholesterol biosynthesis, and free radical scavenging by affecting the expression of key proteins in these processes. Ingenuity Pathway Analysis successfully established several pathway networks, in which many differentially expressed proteins were involved. The differential expression of several proteins was validated by western blotting. Our study offers important information on the mechanism of phlorizin treatment in diabetes mellitus, particularly in the liver. IntroductionType 2 diabetes is one of the most common endocrine diseases in developed countries, which is caused by absolute or relative deficiencies in insulin secretion or insulin action (1). Chronic hyperglycemia is the major biochemical alteration in type 2 diabetes. Moreover, individuals with type 2 diabetes usually display a marked disruption of lipid metabolism, with an abnormal accumulation of fat in various tissues including the liver (2). Hyperglycemia and hyperlipidemia not only impair β-cell function and increase insulin resistance in peripheral tissues, such as the muscle, liver, and adipose tissue (3,4), but also induce oxidative stress reactions, which cause initiation and progression of diabetes-related diseases (5,6). Consequently, regulation of dyslipidemia and reduction in oxidative stress have been regarded as important treatment methods for alleviating diabetes and its complications.Phlorizin (glucose,1-[2-(β.D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone) is a member of the chalcone class of organic compounds and is mainly distributed in the plants of the genus Malus (7). Phlorizin has multiple pharmacological activities, such as anti-oxidative, estrogenic and anti-estrogenic activities, memory improvement and cardioprotective activities (8-11). Reports show that phlorizin inhibits intestinal glucose uptake and renal glucose reabsorption by inhibiting the sodium D-glucose cotransporter (10,12). Phlorizin has been reported to normalize the effects of insulin on glucose metabolism in the liver and other peripheral tissues (13). However, little is known regarding the effect of phlorizin on hepatic damage associated with type 2 diabetes.The rapidly emerging field of quantitative proteomics provides a powerful technique -isobaric tag for relative and absolute quantitation (iTRAQ) labeling combined with liquid chromatograph...

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“…Several studies indicate that dihydrochalcones exhibit particularly potent antioxidant properties [23,118,151]. Phloretin (7) and its glucoside phloridzin (8), two naturally occurring dihydrochalcones isolated from apples, displayed strong scavenging potential against peroxynitrite [151].…”

Section: Effect Of Chalcones On Tumor Initiationmentioning

confidence: 99%

“…Phloretin (7) and its glucoside phloridzin (8), two naturally occurring dihydrochalcones isolated from apples, displayed strong scavenging potential against peroxynitrite [151]. Moreover, phloridzin (8) possesses a remarkable antioxidant activity against superoxide radical, hydrogen peroxide, and hypochlorous acid [23].…”

Section: Effect Of Chalcones On Tumor Initiationmentioning

confidence: 99%

Dietary chalcones with chemopreventive and chemotherapeutic potential

et al. 2011

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Chalcones are absorbed in the daily diet and appear to be promising cancer chemopreventive agents. Chalcones represent an important group of the polyphenolic family, which includes a large number of naturally occurring molecules. This family possesses an interesting spectrum of biological activities, including antioxidative, antibacterial, anti-inflammatory, anticancer, cytotoxic, and immunosuppressive potential. Compounds of this family have been shown to interfere with each step of carcinogenesis, including initiation, promotion and progression. Moreover, numerous compounds from the family of dietary chalcones appear to show activity against cancer cells, suggesting that these molecules or their derivatives may be considered as potential anticancer drugs. This review will focus primarily on prominent members of the chalcone family with an 1,3-diphenyl-2-propenon core structure. Specifically, the inhibitory effects of these compounds on the different steps of carcinogenesis that reveal interesting chemopreventive and chemotherapeutic potential will be discussed.

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The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids

Cited by 263 publications

References 11 publications

Antioxidant Activity of Two Phloroglucinol Derivatives from Dryopteris crassirhizoma

Antioxidant Activity of Two Phloroglucinol Derivatives from Dryopteris crassirhizoma

Quantitative proteomics study on the protective mechanism of phlorizin on hepatic damage in diabetic db/db mice

Dietary chalcones with chemopreventive and chemotherapeutic potential

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