Effect of 5-Caffeoylquinic Acid in the Presence of Metal Chelators on Soybean Oil Oxidative Stability

Luzia, M.R.; Trugo, L.C.; Paixão, Karla C. C. Da; Marcílio, Roberto; María, Carlos; Quinteiro, L.M.C.

doi:10.1006/fstl.1997.0294

Cited by 15 publications

(11 citation statements)

References 11 publications

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“…The 3- O -caffeoylquinic acid and 5- O -caffeoylquinic acid possess ideal structure chemistry for free radical scavenging activities because they have phenolic hydroxyl groups that are prone to donate a hydrogen atom or an electron to a free radical and also extended conjugated aromatic system to delocalize an unpaired electron. According to Luzia et al [ 27 ], 5- O -caffeoylquinic acid could act as a metal chelator due to presence ortho -hydroxy groups in its chemical structure. The fewer the number OH groups, the lower the probability of hydrogen loss and the lower the probability of oxidation of the flavonoid and the reduction of the metal [ 27 ].…”

Section: Discussionmentioning

confidence: 99%

“…According to Luzia et al [ 27 ], 5- O -caffeoylquinic acid could act as a metal chelator due to presence ortho -hydroxy groups in its chemical structure. The fewer the number OH groups, the lower the probability of hydrogen loss and the lower the probability of oxidation of the flavonoid and the reduction of the metal [ 27 ]. Quercetin is a known iron chelator and has iron stabilizing properties.…”

Section: Discussionmentioning

confidence: 99%

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The Antioxidant and Xanthine Oxidase Inhibitory Activity of Plumeria rubra Flowers

Isa¹,

Ablat

Mohamad

2018

Molecules

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Plumeria rubra Linn of the family Apocynaceae is locally known in Malaysia as “Kemboja”. It has been used by local traditional medicine practitioners for the treatment of arthritis-related disease. The LCMS/MS analysis of the methanol extract of flowers (PR-ME) showed that it contains 3-O-caffeyolquinic acid, 5-caffeoquinic acid, 1,3-dicaffeoquinic acid, chlorogenic acid, citric acid, 3,3-di-O-methylellagic acid, kaempferol-3-O-glucoside, kaempferol-3-rutinoside, kaempferol, quercetin 3-O-α-l-arabinopyranoside, quercetin, quinic acid and rutin. The flower PR-ME contained high amounts of phenol and flavonoid at 184.632 mg GAE/g and 203.2.2 mg QE/g, respectively. It also exhibited the highest DPPH, FRAP, metal chelating, hydrogen peroxide, nitric oxide superoxide radical scavenging activity. Similarly, the XO inhibitory activity in vitro assay possesses the highest inhibition effects at an IC50 = 23.91 μg/mL. There was no mortality or signs of toxicity in rats at a dose of 4 g/kg body weight. The administration of the flower PR-ME at doses of 400 mg/kg to the rats significantly reduced serum uric acid 43.77%. Similarly, the XO activity in the liver was significantly inhibited by flower PR-ME at doses of 400 mg/kg. These results confirm that the flower PR-ME of P. rubra contains active phytochemical compounds as detected in LCMS/MS that contribute to the inhibition of XO activity in vitro and in vivo in reducing acid uric level in serum and simultaneously scavenging the free radical to reduce the oxidative stress.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

The Antioxidant and Xanthine Oxidase Inhibitory Activity of Plumeria rubra Flowers

Isa¹,

Ablat

Mohamad

2018

Molecules

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“…[22] Analyzing the isolated compounds, flavones (1, 2) presented a low activity, less than 32 % Tx activity. However, chlorogenic acid derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were more active than flavones showing higher ability to trapping DPPH radicals. CQAs are already known for their potent antioxidant capacity because they have a greater capacity to stabilize radicals due to the presence of catechol group in their structures.…”

Section: Antiradical Assaymentioning

confidence: 99%

Caffeoylquinic Acids: Separation Method, Antiradical Properties and Cytotoxicity

Tamayose

Santos

Roque

et al. 2019

Chemistry & Biodiversity

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Twelve chlorogenic acid derivatives and two flavones were isolated from Moquiniastrum floribundum (Asteraceae, other name: Gochnatia floribunda). Compounds were evaluated in relation to their cytotoxicity and antiradical properties. Cytotoxicity was not observed for compounds, however, chlorogenic acid derivatives showed antiradical activity and were more active than the Trolox standard. Quinic acid esterified with caffeoyl group at C‐4 position showed higher antiradical activity compared to acylation at C‐3 or C‐5 positions. Additional caffeoyl groups esterified in quinic acid increase the antiradical activity observed for 4‐caffeoylquinic acid. Excepted to 3,4‐dicaffeoylquinic acid methyl ester, methyl ester derivatives show higher capacity of trapping radicals than their respective acids. Consequently, the presence of caffeoyl group at C‐4 position of quinic acid is suggested as fundamental to obtain the highest antiradical activity.

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“…O ácido clorogênico faz parte do grupo de ácidos fenólicos que se caracterizam por ter um anel benzênico, um grupo carboxílico e um ou mais grupos de hidroxila e/ou metoxila na molécula, o que lhes confere propriedades antioxidantes, tanto para os alimentos como para o organismo (SOARES, 2002). A ação antioxidante do ácido clorogênico atribui-se à presença de um grupo orto-di-hidroxila no anel aromático do ácido cafeico, que atuaria como um receptor de radicais livres (LUZIA et al, 1998).…”

Section: Compostos Fenólicos Nos Extratosunclassified

Capacidade antioxidante em resíduos da indústria cafeeira

García

Bianchi

2015

Braz. J. Food Technol.

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ResumoEste trabalho teve como objetivo a recuperação de compostos fenólicos a partir de resíduos da indústria cafeeira e a avaliação de sua capacidade antioxidante. Os resíduos (casca, polpa e borra de café) foram obtidos de diferentes etapas do processamento industrial do café. Os extratos fenólicos foram obtidos usando-se uma mistura de acetona e água. O teor de compostos fenólicos variou entre 72,88 e 159,50 mg AG g -1 resíduo. Mediante cromatografia líquida de alta eficiência foi detectado e quantificado o ácido clorogênico na casca e na polpa de café. Foi avaliada a capacidade antioxidante dos extratos fenólicos, verificando-se sua capacidade sequestrante de radicais DPPH e sua ação redutora sobre radicais peroxila. O resíduo com maior capacidade antioxidante foi a casca de café. Esses resultados sugerem a possibilidade de reutilização dos resíduos da indústria do café para a obtenção de compostos antioxidantes, pois tais compostos têm inúmeras aplicações nas áreas de alimentos, cosméticos e farmacêutica. Palavras-chave: Resíduos de café; Compostos fenólicos; Ácido clorogênico; Radical livre DPPH; Radical peroxila. SummaryThe aim of this study was to recover the phenolic compounds from coffee industry residues and evaluate their antioxidant capacity. The residues (husk, pulp and spent coffee) were obtained from different steps of the industrial processing of coffee. The phenolic extracts were obtained using a mixture of acetone and water and the phenolic compound contents ranged between 72.88 and 159.50 mg GA g -1 residue. Chlorogenic acid was detected and quantified in the coffee husk and pulp by high performance liquid chromatography (HPLC). The antioxidant capacity of the phenolic extracts was evaluated and they showed DPPH radical scavenging ability and reducing action against peroxyl radicals. The residue with the highest antioxidant capacity was the coffee husk. The results suggest the possibility of reusing the coffee industry residues to obtain antioxidant compounds, since these compounds have numerous applications in the food, cosmetic and pharmaceutical industries.

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Effect of 5-Caffeoylquinic Acid in the Presence of Metal Chelators on Soybean Oil Oxidative Stability

Cited by 15 publications

References 11 publications

The Antioxidant and Xanthine Oxidase Inhibitory Activity of Plumeria rubra Flowers

The Antioxidant and Xanthine Oxidase Inhibitory Activity of Plumeria rubra Flowers

Caffeoylquinic Acids: Separation Method, Antiradical Properties and Cytotoxicity

Capacidade antioxidante em resíduos da indústria cafeeira

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