Characterization of antioxidant effect of procyanidins

Ursini, Fulvio; Rapuzzi, Ivan; Toniolo, Rosanna; Tubaro, Franco; Bontempelli, Gino

doi:10.1016/s0076-6879(01)35256-4

Cited by 45 publications

(37 citation statements)

References 14 publications

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“…The polymerized chains of catechin monomers that form procyanidin trimers usually have a lower ability to prevent radical damage in lipid system, than in aqueous phase (Plumb, De Pascual-Teresa, Santos-Buelga, Cheynier, & Williamson, 1998). Dimeric and oligomeric B-type procyanidins possess greater scavenging activity toward peroxyl radicals than catechins, which is probably due to the presence of interflavonoid linkage that increases the electron delocalization capacity of the phenyl radical (Ursini, Rapuzzi, Toniolo, Tubaro, & Bontempelli, 2001). In cranberry, anthocyanins are among the principal antioxidant constituents, although hydroxycinnamates such as chlorogenic acid, and hydrolyzable tannins and condensed tannins are also effective antioxidants.…”

Section: Free Radical-scavenging Activity Versus Lipid Peroxidation Imentioning

confidence: 99%

Antioxidant and antiradical properties of cranberry juice and extracts

Caillet

Côté

Doyon

et al. 2011

Food Research International

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Section: Free Radical-scavenging Activity Versus Lipid Peroxidation Imentioning

confidence: 99%

Antioxidant and antiradical properties of cranberry juice and extracts

Caillet

Côté

Doyon

et al. 2011

Food Research International

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“…The authors found that polymers with degree of polymerization > 10 constituted predominating subclass of procyanidins (542.6 mg per 100 g of fresh weight). According to Ursini et al (2001), procyanidins are considered to be superior antioxidants compared to their corresponding monomers. The content of flavonols (quercetin glycosides) ranged from 31.54 (Mn variant) to 40.88 mg per 100 g (Alkalin), and their participation in total polyphenol content was rather low compared to polymeric procyanidins, cyanidins, and chlorogenic acids.…”

Section: A G R I C U L T U R a L A N D F O O D S C I E N C E Phenolicmentioning

confidence: 99%

The effect of mineral fertilization on nutritive value and biological activity of chokeberry fruit

Skupień¹,

Oszmiański²

2008

AFSci

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The aim of the study was to assess whether an extra fertilization with manganese, commercial fertilizer Alkalin (N, K and Si), and combined treatment (manganese + Alkalin) affect the chemical composition of chokeberry fruits (Aronia melanocarpa (Michx) Elliot), especially sugar content and the quantity and profile of phenolics. Dry weight, soluble solids, titratable acidity, total sugar, reducing sugar, sucrose, vitamin C, total polyphenol (gallic acid equivalents); 2, 2-diphenyl-1-picrylhydrazyl radical scavenging activity; and phenolics profile were measured from the fruits harvested from different treatments. Chokeberries treated with manganese showed high content of non-identified phenolic acids [101.15 mg per 100 g fresh weight (FW), these compounds were not detected in fruit treated with Alkalin and manganese + Alkalin], and the highest content of cyanidin glycosides (813.75 mg per 100 g FW). The fruits treated with Alkalin displayed the highest content of quercetin derivatives (40.88 mg per 100 g FW) and eriodictyol 7-glucuronide (26.43 mg per 100g FW). Chokeberries in control treatments had the highest content of dry weight (30.76% FW), soluble solids (24.1% FW), total sugar (20.92% FW), vitamin C (8.4 mg 100 g -1 FW), total polyphenol (2377.1 mg gallic acid equivalents per 100 g FW), the highest 2, 2-diphenyl-1-picrylhydrazyl radical % inhibition (38.1%), highest content of chlorogenic acids (210.38 mg per 100 g FW), (-)epicatechin (32.18 mg per 100 g FW) and the highest degree of procyanidin polimerization (59). The results indicate that applied fertilization exerted differential influence on chemical composition of aronia fruits.

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“…7 The so-called 'French Paradox' stems from the observation that French people consuming as much as 1200 mg of flavonoids per liter of red wine with structures similar to 1 and 2 display lower incidences of coronary disease despite a higher intake of saturated fat. [8][9][10][11][12] In addition to these suppositious medical benefits, compounds 1 and 2 resemble antihyperglycemic components found within cinnamon, which have been studied for their ability to potentiate insulin, maintain normal blood sugar levels, and assist in fat metabolism. 13 Currently insulin resistance, which is referred to as metabolic syndrome X, affects 50 million people.…”

Section: Biological Relevancementioning

confidence: 99%

(±)-Diinsininone: made nature's way

Selenski

Pettus

2006

Tetrahedron

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We report the synthesis of diinsininone (33), the aglycone of (±)-diinsinin (2). Thereby, we complete the first construction of a proanthocyanidin (PA) type-A compound incorporating a [3.3.1]-bicyclic ketal as its characteristic core. Our strategy utilizes a coupling between a benzopyrilium salt and a flavanone that proves applicable to other PA type-A compounds. During this undertaking, treatment of naringenin (9) with 2-iodoxybenzoic acid (IBX) followed by reductive work-up affords eriodictyol (10). This reactivity mirrors that of catechol hydroxylase (F3H) found in the flavonoid pathway. Other interesting transformations include the formation of flavonoids through an ortho-quinone methide (o-QM) cycloaddition-oxidation sequence and regioselective β-glycosidations of several unprotected flavanones suggesting a likely synthesis of 2 from the aglycone 33.

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Characterization of antioxidant effect of procyanidins

Cited by 45 publications

References 14 publications

Antioxidant and antiradical properties of cranberry juice and extracts

Antioxidant and antiradical properties of cranberry juice and extracts

The effect of mineral fertilization on nutritive value and biological activity of chokeberry fruit

(±)-Diinsininone: made nature's way

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