Nitration reaction of lutein with peroxynitrite

Tsuboi, Makoto; Etoh, Hideo; Yomoda, Yuya; Kato, Katsuichi; Kato, Hideaki; Kulkarni, Aditya; Terada, Yukimasa; Maoka, Takashi; Mori, Haruhiko; Inakuma, Takahiro

doi:10.1016/j.tetlet.2009.11.099

Cited by 9 publications

(9 citation statements)

References 5 publications

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“…In the second one, lycopene directly reacts with ONOO − to produce a dioxetane that cleaves to apo-lycopenals or undergoes methanolysis to yield methoxy-lycopene [ 33 ]. Moreover, recently the formation of nitrocarotenoids as a result of the reaction between carotenoids and ONOO − was described [ 34 , 35 ].…”

Section: Discussionmentioning

confidence: 99%

Scavenging Capacity of Marine Carotenoids against Reactive Oxygen and Nitrogen Species in a Membrane-Mimicking System

2012

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Carotenoid intake has been associated with the decrease of the incidence of some chronic diseases by minimizing the in vivo oxidative damages induced by reactive oxygen (ROS) and nitrogen species (RNS). The carotenoids are well-known singlet oxygen quenchers; however, their capacity to scavenge other reactive species, such as peroxyl radical (ROO•), hydroxyl radical (HO•), hypochlorous acid (HOCl) and anion peroxynitrite (ONOO−), still needs to be more extensively studied, especially using membrane-mimicking systems, such as liposomes. Moreover, the identification of carotenoids possessing high antioxidant capacity can lead to new alternatives of drugs or nutritional supplements for prophylaxis or therapy of pathological conditions related to oxidative damages, such as cardiovascular diseases. The capacity to scavenge ROO•, HO•, HOCl and ONOO− of seven carotenoids found in marine organisms was determined in liposomes based on the fluorescence loss of a fluorescent lipid (C11-BODIPY581/591) due to its oxidation by these reactive species. The carotenoid-bearing hydroxyl groups were generally more potent ROS scavengers than the carotenes, whilst β-carotene was the most efficient ONOO− scavenger. The role of astaxanthin as an antioxidant should be highlighted, since it was a more potent scavenger of ROO•, HOCl and ONOO− than α-tocopherol.

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Section: Discussionmentioning

confidence: 99%

Scavenging Capacity of Marine Carotenoids against Reactive Oxygen and Nitrogen Species in a Membrane-Mimicking System

2012

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“…This may increase the antioxidant properties as well. Several studies are reported on the introduction of novel reactions to Lutein chemistry [12,13]. In recent years, attempts have been made to increase the hydrophilicity of Lutein due to its potential applications in the medicine and food industries.…”

Section: Discussionmentioning

confidence: 99%

“…Lutein is shown to possess pronounced free radical scavenging ability due to its polarity and number of conjugated double bonds [11], however chemical synthesis of their derivatives has proven to be better in their biological activity [12]. Lutein-6H-1,2-oxazine along with 14-s-cis-5-nitrolutein is reported to exhibit better scavenging activity of peroxynitrite and nitrogen radicals [13]. 15-nitroastaxanthin, derivative of astaxanthin is reported to inhibit invitro Epstein-Barr virus early antigen activation and twostage carcinogenesis in mouse skin papillomas.…”

Section: Introductionmentioning

confidence: 99%

Studies on Inhibition of H2O2 Induced TGF–β1 Expression in Peripheral Blood Mononuclear Cells by Novel Pyridine Appended Lutein Derivative

Chethankumar¹

2016

MOJCSR

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Lutein a hydroxy carotenoid belonging to xanthophyll group having a hydroxyl group attached to either end of the molecule, making it react more strongly with singlet oxygen than other carotenoids. In the present study, Lutein was modified by appending pyridine moiety for increased antioxidant activity and its ability to inhibit H 2 O 2 induced TGF-β1 expression in peripheral blood mononuclear cells was investigated. Lutein was treated with Isonicotinic acid (Pyridine-4-carboxylic acid) in the presence of DCC and DMF as solvent medium to obtain pyridine appended Lutein (2.28mg/ml). The pyridine appended Lutein was purified using silica gel-G (60-120mesh) column, further by HPLC and fractions were eluted at the rate of 1ml/min using water, acetonitrile, methanol and dichloromethane as mobile phase in the ratio 0.5:9.5:67.5:22.5. A major peak was obtained at 454nm with retention time of 1.60min. In dose dependent study, Pyridine appended Lutein at 0.42µmoles showed a maximum of 91.6% of DPPH radical scavenging activity in comparison to unmodified Lutein (80.76%). Unmodified Lutein showed maximum activity (86.18% at 1.25µmoles) with 2.97 folds higher than Pyridine appended Lutein. TGF-β1 expression in H 2 O 2 (3mM) treated peripheral blood mononuclear cells was inhibited by 83.14% (152.1pg/ml) and 76.21% (214.62pg/ml) at 0.92µmoles of Pyridine appended Lutein and unmodified Lutein respectively compared to H 2 O 2 treated cells (902.15pg/ml) without test samples. In conclusion, Pyridine appended Lutein showed higher DPPH radical scavenging activity and inhibited H 2 O 2 induced TGF-β1 expression in peripheral blood mononuclear cells at low concentrations than unmodified Lutein.

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“…12 Lutein-6H-1,2-oxazine along with 14-s-cis-5-nitrolutein is reported to exhibit better scavenging activity of peroxynitrite and nitrogen radicals. 13 15-nitroastaxanthin, derivative of astaxanthin is reported to inhibit in vitro Epstein-Barr virus early antigen activation and two-stage carcinogenesis in mouse skin papillomas. Similar results are reported for the 15-nitrolutein, a major reaction product of lutein with peroxynitrite.…”

Section: Introductionmentioning

confidence: 99%

“…Several studies are reported on the introduction of novel reactions to Lutein chemistry. 12,13 In recent years, attempts have been made to increase the hydrophilicity of Lutein due to its potential applications in the medicine and food industries. Pyridine is a heterocyclic organic compound with the chemical formula C 5 H 5 N. It is structurally related to benzene, with one CH group replaced by a nitrogen atom.…”

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confidence: 99%

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2016

MOJCSR

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Lutein a hydroxy carotenoid belonging to xanthophyll group having a hydroxyl group attached to either end of the molecule, making it react more strongly with singlet oxygen than other carotenoids. In the present study, Lutein was modified by appending pyridine moiety for increased antioxidant activity and its ability to inhibit H 2 O 2 induced TGF-β1 expression in peripheral blood mononuclear cells was investigated. Lutein was treated with Isonicotinic acid (Pyridine-4-carboxylic acid) in the presence of DCC and DMF as solvent medium to obtain pyridine appended Lutein (2.28mg/ml). The pyridine appended Lutein was purified using silica gel-G (60-120mesh) column, further by HPLC and fractions were eluted at the rate of 1ml/min using water, acetonitrile, methanol and dichloromethane as mobile phase in the ratio 0.5:9.5:67.5:22.5. A major peak was obtained at 454nm with retention time of 1.60min. In dose dependent study, Pyridine appended Lutein at 0.42µmoles showed a maximum of 91.6% of DPPH radical scavenging activity in comparison to unmodified Lutein (80.76%). Unmodified Lutein showed maximum activity (86.18% at 1.25µmoles) with 2.97 folds higher than Pyridine appended Lutein. TGF-β1 expression in H 2 O 2 (3mM) treated peripheral blood mononuclear cells was inhibited by 83.14% (152.1pg/ ml) and 76.21% (214.62pg/ml) at 0.92µmoles of Pyridine appended Lutein and unmodified Lutein respectively compared to H 2 O 2 treated cells (902.15pg/ml) without test samples. In conclusion, Pyridine appended Lutein showed higher DPPH radical scavenging activity and inhibited H 2 O 2 induced TGF-β1 expression in peripheral blood mononuclear cells at low concentrations than unmodified Lutein.Keywords: DPPH radical, isonicotinic acid, n,n'-dicyclohexylcarbodiimide, n,ndimethyl formamide, lutein, TGF-β1

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Nitration reaction of lutein with peroxynitrite

Abstract: The in vitro reactivity of lutein toward peroxynitrite was investigated, and the reaction products produced by scavenging with peroxynitrite were analyzed. A novel

Cited by 9 publications

References 5 publications

Scavenging Capacity of Marine Carotenoids against Reactive Oxygen and Nitrogen Species in a Membrane-Mimicking System

Scavenging Capacity of Marine Carotenoids against Reactive Oxygen and Nitrogen Species in a Membrane-Mimicking System

Studies on Inhibition of H2O2 Induced TGF–β1 Expression in Peripheral Blood Mononuclear Cells by Novel Pyridine Appended Lutein Derivative

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