Inhibition of human low-density lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivatives

Nardini, Mirella; D'Aquino, Massimo; Tomassi, G.; Gentili, Vincenzo; Felice, Maurizio Di; Scaccini, Cristina

doi:10.1016/0891-5849(95)00052-y

Cited by 420 publications

(272 citation statements)

References 38 publications

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“…It has in fact been widely observed that caffeic acid, a simple polyphenol with an ortho-diphenolic structure, can have pro-oxidant activity on LDL oxidation induced by Cu 2þ (Yamanaka et al 1997). However, this pro-oxidant activity has been found only in the propagation phase of oxidation, and not in the initiation phase, in which caffeic acid inhibits lipoprotein oxidation, as has been found in previous studies (Laranjinha et al 1994;Nardini et al 1995).…”

Section: The Antioxidant Activity Of the Polyphenolic Compoundsmentioning

confidence: 72%

The phenolic compounds of olive oil: structure, biological activity and beneficial effects on human health

et al. 2005

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The Mediterranean diet is rich in vegetables, cereals, fruit, fish, milk, wine and olive oil and has salutary biological functions. Epidemiological studies have shown a lower incidence of atherosclerosis, cardiovascular diseases and certain kinds of cancer in the Mediterranean area. Olive oil is the main source of fat, and the Mediterranean diet's healthy effects can in particular be attributed not only to the high relationship between unsaturated and saturated fatty acids in olive oil but also to the antioxidant property of its phenolic compounds. The main phenolic compounds, hydroxytyrosol and oleuropein, which give extra-virgin olive oil its bitter, pungent taste, have powerful antioxidant activity bothin vivoandin vitro. The present review focuses on recent works analysing the relationship between the structure of olive oil polyphenolic compounds and their antioxidant activity. These compounds' possible beneficial effects are due to their antioxidant activity, which is related to the development of atherosclerosis and cancer, and to anti-inflammatory and antimicrobial activity.

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Section: The Antioxidant Activity Of the Polyphenolic Compoundsmentioning

confidence: 72%

The phenolic compounds of olive oil: structure, biological activity and beneficial effects on human health

et al. 2005

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“…The results clearly showed that these phenolic compounds, without dialysis, readily increased the defense of the lipoparticle against the oxidative stress. The higher protection provided by caffeic acid (3,4-dihydroxy-cinnamic acid) as compared with sinapic and ferulic acids (4-hydroxy-3,5-dimethoxy-cinnamic and 4-hydroxy-3-methoxy-cinnamic acids, respectively) underlines the negative effect of the presence of methoxyl group(s) on the aromatic cycle near the phenyl hydroxyl in preventing oxidation (Rafat et al, 1987;Nardini et al, 1995) as well as the positive effect of the orthodiphenol con®guration. However, the antioxidative protection of phenolic compounds was totally lost after extensive LDL dialysis.…”

Section: Discussionmentioning

confidence: 99%

Supplementation with wine phenolic compounds increases the antioxidant capacity of plasma and vitamin E of low-density lipoprotein without changing the lipoprotein Cu2+-oxidizability: Possible explanation by phenolic location

Carbonneau¹,

Léger²,

Monnier

et al. 1997

Eur J Clin Nutr

101

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Objectives: To evaluate the effect of the red wine phenolic compound (RWPC) dietary supplementation without alcohol interference on: (1) some of the biochemical characteristics of LDL, (2) the oxidative susceptibility of LDL and (3) the antioxidant capacity of total plasma (Pl-AOC). In order to account for discrepancies between the three series of data, the in vitro stability of the association of phenolic compounds and LDL was tested. Design: An intervention study with 20 volunteers. Each served as his own control. Cu 2 -oxidizability of LDL and Pl-AOC were tested on blood samples before and after dietary supplementation. Cu 2 -oxidizability of LDL was also tested by co-incubation in the presence of RWPC or phenolic acids with or without extensive dialysis. Setting: The Laboratory of Lipid Biochemistry and Biology, School of Medicine, and the Laboratory of Metabolic Diseases, Lapeyronie Hospital, University of Montpellier, France. Subjects: Healthy males, nonsmokers and moderate drinkers, submitted to a dietary regimen deprived of vitamin E and C for a period of 10 d before supplementation. They also abstained from alcohol, wine, fruit juices, coffee, tea and cola beverages during this period. Intervention: Six 0.33 g capsulesad (namely two capsules at each meal) of a preparation of red wine phenolic compounds in a dry powder form were given to the volunteers over a period of two weeks. Blood samples were drawn in fasting conditions at day 0 and day 14 of the supplementation period. Results: Supplementation led to: (1) in LDL, a signi®cant increase in vitamin E content (n 20, P 0.01) or vitamin Eatotal fatty acid bis-allylic carbon number ratio (n 20, P 0.006) without modi®cation in the other biochemical characteristics or Cu 2 -oxidizability; (2) in plasma, a signi®cant increase in the antioxidant capacity (n 11, P 0.01). In vitro studies showed that RWPC or sinapic, caffeic or ferulic acids incubated in the presence of LDL increased the protection of the lipoparticle against oxidation (caffeic b sinapic b ferulic). This effect, however, was totally lost after extensive dialysis. Conclusions: The enhancing effect of the RWPC supplementation on Pl-AOC may be due to a phenoliccompound action both in the aqueous phase of plasma and at the surface of lipoprotein particles. Surface location possibly explains the enhancing-sparing effect of supplementation on LDL vitamin E and the absence of effect on dialysed-LDL oxidizability.

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“…Previously, attention has been focused on phenolic acids mainly owing to their in vitro (20,(48)(49)(50)(51)(52) and in vivo (27,(53)(54)(55)(56) antioxidant activity. Also, the main phenolic acids from barley (ferulic, p-coumaric and vanillic acids) have been mentioned as potent antioxidants in beer (51,(57)(58)(59).…”

Section: Resultsmentioning

confidence: 99%

Phenolic acids from malt are efficient acetylcholinesterase and butyrylcholinesterase inhibitors

Szwajgier

Borowiec

2012

J. Inst. Brew.

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Anticholinesterase activities of mashes produced using wheat ('Wheat Pale') or barley malts ('Pilsner', 'Pale Ale', 'Munich Light', 'Carahell' or 'Carared') were studied by spectrophotometric method. The highest inhibition of acetylcholinesterase and butyrylcholinesterase was observed at 52 C and/or 64 C, followed by a decrease or stabilization of the activity at 72 C. Changes in the total phenolics content in the test mashes were correlated with changes in the acetylcholinesterase and/or butyrylcholinesterase activities. Phenolic acids were singled out from phenolic compounds for more detailed studies owing to their simplicity and structural similarity to well-known cholinesterase inhibitors. The main phenolic acids in the test malts were ferulic, gallic, p-coumaric and vanillic acids followed by chlorogenic, caffeic, syringic, p-OH-benzoic, sinapic and protocatechuic acids. The anticholinesterase activities of the phenolic acids were studied using model standard solutions at concentrations similar to the maximal content of these compounds in the test mashes. Among the phenolic acids, p-coumaric acid had the largest share in the anticholinesterase activity, even though it was present in the test mashes at a significantly lower concentration (~0.38 mM L À1 ) than ferulic acid (~1.00 mM L À1 ). Sinapic acid and p-OH-benzoic acid (0.03 and 0.01 mM L À1 , respectively) were equally efficient inhibitors as ferulic acid at~1.00 mM L À1 . This preliminary study should be extended to other phenolic compounds from malt (wort) in the near future.

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Inhibition of human low-density lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivatives

Cited by 420 publications

References 38 publications

The phenolic compounds of olive oil: structure, biological activity and beneficial effects on human health

The phenolic compounds of olive oil: structure, biological activity and beneficial effects on human health

Supplementation with wine phenolic compounds increases the antioxidant capacity of plasma and vitamin E of low-density lipoprotein without changing the lipoprotein Cu2+-oxidizability: Possible explanation by phenolic location

Phenolic acids from malt are efficient acetylcholinesterase and butyrylcholinesterase inhibitors

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