Flavonoids From the Leaves of Kalmia latifolia

El-Naggar, Sha'aban F.; El‐Feraly, Farouk S.; Foos, J. S.; Doskotch, Raymond W.

doi:10.1021/np50012a008

Cited by 25 publications

(24 citation statements)

References 15 publications

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confidence: 99%

“…10) In recent studies, there were several reports about improve the solubility and stability in aqueous solution and another research group evaluated neohesperidin-rich plant to get a source of NHDC. 8,11) Some dihydrochalcones including phloridzin and myrigalone B have been found to occur naturally 12,13) and to possess an antioxidant activity.14,15) Several chalcones inhibit various enzymes involved in the generation of reactive oxygen species and many of their pharmacological properties are supposed to be related to their antioxidant effect.16) Recently, 2Ј,5Ј-dihydroxychalcones have been reported as potent anti-inflammatory chemicals. 17,18) Although a large number of antioxidants, including most types of flavonoids, have been reported in the literature, there are few systematic studies of dihydrochalcones on biological activities such as an antioxidant effect.…”

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Antioxidant Properties of Neohesperidin Dihydrochalcone: Inhibition of Hypochlorous Acid-Induced DNA Strand Breakage, Protein Degradation, and Cell Death

Choi

Yoon

Lee

et al. 2007

Biological & Pharmaceutical Bulletin

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Reactive oxygen species (ROS) and free radicals induce membrane damages, DNA strand breaks, and protein alterations. Oxidative stress, induced by oxygen radicals, is believed to be a primary factor in various degenerative diseases as well as in the normal process of aging. The ROS are involved in the course of aging, cancer, cardiovascular disease, diabetes, neurodegenerative disease, osteoporosis, etc. 1,2) Among the various reactive species, superoxide radical ( · O 2 Ϫ ), hydroxyl radical ( · OH), hydrogen peroxide (H 2 O 2 ), and hypochlorous acid (HOCl) play important roles in the pathophysiologies as mentioned above, which make them potential targets for the chemotherapy of inflammatory diseases. 3)Neohesperidin dihydrochalcone (NHDC) is an intense sweetener which is produced by hydrogenation of neohesperidin first prepared by Horowitz and Gentili in 1963. 4) Citrus fruits are rich sources of neohesperidin; the peels of oranges, lemons, and grapefruit contain bitter taste of neohesperidin. [5][6][7][8][9] Dihydrochalcones are a family of the bicyclic flavonoids, defined by the presence of two benzenoid rings joined by a three-carbon bridge. NHDC, the most familiar among these compounds, is permitted for commercial use as a food additive in Europe on the basis of its safety assessed by the EU Scientific Committee for Food. 10) In recent studies, there were several reports about improve the solubility and stability in aqueous solution and another research group evaluated neohesperidin-rich plant to get a source of NHDC. 8,11) Some dihydrochalcones including phloridzin and myrigalone B have been found to occur naturally 12,13) and to possess an antioxidant activity.14,15) Several chalcones inhibit various enzymes involved in the generation of reactive oxygen species and many of their pharmacological properties are supposed to be related to their antioxidant effect.16) Recently, 2Ј,5Ј-dihydroxychalcones have been reported as potent anti-inflammatory chemicals. 17,18) Although a large number of antioxidants, including most types of flavonoids, have been reported in the literature, there are few systematic studies of dihydrochalcones on biological activities such as an antioxidant effect. In recent studies, NHDC can inhibit DPPH stable radical, lipid peroxidation, and xanthine oxidase activity. 19,20) However, there are few reports to evaluate NHDC as an antioxidant or specific radical scavenger.In this study, to evaluate NHDC as a novel antioxidant material for a pharmaceutical agent or a food additive, its stable radical scavenging activity and inhibitory effect on the major inflammation-related ROS including · O 2 Ϫ , H 2 O 2 , · OH, and HOCl were elaborated. Also, the inhibitory effect of NHDC on protein degradation, DNA strand cleavage, and cellular damage from HOCl attack were determined to verify the specific ROS scavenging function. In addition, the ROS scavenging effect of the structurally related compounds including neohesperidin and phloridzin was also estimated to explore the structure-activity rel...

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confidence: 99%

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confidence: 99%

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Antioxidant Properties of Neohesperidin Dihydrochalcone: Inhibition of Hypochlorous Acid-Induced DNA Strand Breakage, Protein Degradation, and Cell Death

Choi

Yoon

Lee

et al. 2007

Biological & Pharmaceutical Bulletin

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“…The J value (7.0 xbHz) of the anomeric proton concluded the β-configuration of the glucose moiety. These NMR features were resembled to those of compound 2 , phloretin-4'-O-β-D-glucopyranoside [5], except for the existence of an additional set of signals arising from one α-L-rhamnopyranosyl [δ 5.04, (1H, br s, H-1'") and 1.25 (3H, d, J = 6.2 Hz , H-6'")], a methoxyl groups [δ 3.70 (3H, s)] reduced from 1 H NMR, 13 C NMR and HMQC-TOCSY in 1 . In addition, 1, 3, 4-trisubstituted phenyls in A-ring compound 1 , instead of 1, 4-disubstituted aromatic A-rings in the above-mentioned glycoside.…”

Section: Resultsmentioning

confidence: 92%

Dihydrochalcone glycosides from Oxytropis myriophylla

She

Wang

Liu

2011

Chemistry Central Journal

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Chemical investigations of the 70% alcohol extract of Oxytropis myriophylla (Pall.) DC. (Leguminosae) have afforded the new natural product neohesperidin dihydrochalcone (1) and the known phloretin-4'-O-β-D-glucopyranoside (2), which was the first reported from the genus Oxytropis. This paper reports the isolation and full spectroscopic characterization of compounds 1 and 2 by NMR, UV, IR and MS data.

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“…Identification of the target compound was carried out by UV, IR, MS, 1 H NMR and 13 C NMR analysis as follows: [16].…”

Section: Structural Identificationmentioning

confidence: 99%

High-speed counter-current chromatography preparative separation and purification of phloretin from apple tree bark

Kai

Lü

et al. 2010

Separation and Purification Technology

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Flavonoids From the Leaves of Kalmia latifolia

Cited by 25 publications

References 15 publications

Antioxidant Properties of Neohesperidin Dihydrochalcone: Inhibition of Hypochlorous Acid-Induced DNA Strand Breakage, Protein Degradation, and Cell Death

Antioxidant Properties of Neohesperidin Dihydrochalcone: Inhibition of Hypochlorous Acid-Induced DNA Strand Breakage, Protein Degradation, and Cell Death

Dihydrochalcone glycosides from Oxytropis myriophylla

High-speed counter-current chromatography preparative separation and purification of phloretin from apple tree bark

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