Singlet Oxygen Quenching Abilities of Carotenoids

Baltschun, Dietmar; Beutner, Stefan; Briviba, Karlis; Martin, Hans‐Dieter; Paust, Joachim; Peters, M.; Röver, Stephan; Sies, Helmut; Stahl, Wilhelm; Steigel, Alois; Stenhorst, Frank

doi:10.1002/jlac.199719970913

Cited by 58 publications

(59 citation statements)

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“…___________________________________________________________________________ FULL PAPER Synthesis, characterization, and properties of the carotenoids are described in several published articles [7][8][9], all other compounds will be introduced in this publication (see Experimental). β-Carotene (1a), canthaxanthin (4a), zeaxanthin (3a), astaxanthin (5a), lycopene (2a), tetrahydrolycopene (2c), 13-cis-Phytoene (2e) and all-trans-Phytoene (2d) were provided by BASF AG.…”

Section: Scheme 1 Structures Of All Investigated Carotenoid Compoundsmentioning

confidence: 99%

Anti- and Prooxidant Properties of Carotenoids

Martin¹,

Jäger²,

Ruck³

et al. 1999

J. prakt. Chem.

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302Carotenoids are widely distributed in nature where they play an important role in cell protection [1]. Oxygen species including 1 O 2 , 3 O 2 and O 2 · -are capable to damage lipid membranes as well as DNA, and become the cause of mutation of cell material. Carotenoids can play the role of versatile antioxidants because they are effective biological quenchers as well as radical chain breaking agents [2]. Many studies including in vitro, in vivo and epidemiological tests were carried out to investigate these properties of carotenoids [3 -5]. β-Carotene (1a), as the best known carotenoid compound, shows the remarkable effect of changing its antioxidant to a prooxidant behaviour at high concentrations of β-carotene and in the presence of high oxygen partial pressures [2]. Since epidemiological studies can show contradictory and confounding results [3 -5], a more thorough inspection of the anti-and prooxidant functions of carotenoids is needed. Carotenoids with antioxidative properties better than β-carotene (1a), like astaxanthin (5a), have attracted special interest [6a,c].In this study we present an approach to a better understanding of these anti-and prooxidant properties of carotenoids and describe carotenoids, both natural and synthetic, with sole antioxidant efficiency approaching that of α-tocopherol. Anti-and Prooxidant Properties of CarotenoidsHans-Dieter Martin*, Claudia Jäger, Christoph Ruck, and Marcus Schmidt Düsseldorf, Institute of Organic Chemistry and Macromolecular Chemistry, University Robin WalshReading/UK, Department of Chemistry, University Joachim PaustLudwigshafen, BASF AG Received Februar 8th, 1999 Dedicated to Professor Fritz Vögtle on the Occasion of his 60th BirthdayKeywords: Autoxidation, Carotenoids, Oxygen, Antioxidant, Prooxidant Abstract. Carotenoids can be effective singlet oxygen quenchers and inhibit free-radical induced lipid peroxidation. A remarkable property of β-carotene (1a) is the change from an antioxidant to a prooxidant depending on oxygen pressure and concentration. In the present study a considerable number of carotenoids (1a, 2c, 2d, 2e, 3a, 4a, 5a, 6a, 7a, 8a, 8h, 8i, 8j, 9f, 10a, 11a, 12g) was investigated using two independent approaches: 1. Comparison of their effects on inhibition of the free-radical oxidation of methyl linoleate, and 2. The direct study of the effect of oxygen partial pressure upon their rates of oxidation. It is shown that some carotenoids (7a, 8a) are even more effective than the well-known compounds β-carotene (1a) and astaxanthin (5a) and are powerful antioxidants without any prooxidative property. Different carotenoids display different behaviour depending on chain length and end groups. The influence of these functional groups on the antioxidative reactivity is discussed.Scheme 1 Structures of all investigated carotenoid compounds 1-12

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Section: Scheme 1 Structures Of All Investigated Carotenoid Compoundsmentioning

confidence: 99%

Anti- and Prooxidant Properties of Carotenoids

Martin¹,

Jäger²,

Ruck³

et al. 1999

J. prakt. Chem.

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“…13,20±22 b-Carotene 1b, canthaxanthin 2b, astaxanthin 3b and lycopene 14b were provided by BASF AG. Rhodoxanthin 15 was generously supplied by Dr A Ru È ttimann, Hoffmann-La Roche.…”

Section: Singlet Oxygen Quenchingmentioning

confidence: 99%

“…10,11 The underlying mechanisms are yet unknown, but the importance of the carotenoids is at least partially discussed in terms of their antioxidant activity. 12 Polyenes and carotenoids are the best known among the compounds that quench 1 O 2 by ef®cient energy transfer: 13 1 O 2 Q → 3 O 2 3 Q. A large number of modi®ed, synthetic analogues and derivatives have been synthesised in order to prepare even better quenchers than the natural carotenoids b-carotene, canthaxanthin and astaxanthin.…”

Section: Introductionmentioning

confidence: 99%

Quantitative assessment of antioxidant properties of natural colorants and phytochemicals: carotenoids, flavonoids, phenols and indigoids. The role of β‐carotene in antioxidant functions

Beutner¹,

Bloedorn²,

Frixel³

et al. 2001

J Sci Food Agric

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216

151

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Reactive oxygen species are potentially damaging molecules. An important function of antioxidants is to intercept harmful triplet states, in order to prevent the formation of singlet oxygen, or to quench singlet oxygen directly. However, antioxidants are also reactive towards other active oxygen species such as the hydroxyl radical, the superoxide anion and the non-excited oxygen ground state in the presence of radical initiators. It is well known that¯avonoids and carotenoids show strong antioxidant properties. Polyenes and carotenoids are the best known among the compounds that quench singlet oxygen by ef®cient energy transfer. A large number of modi®ed, synthetic analogues and derivatives have been synthesised to prepare even better quenchers than the natural carotenoids. Phenols are also excellent chain-breaking antioxidants. Recently, many indigoid dyes (including bacterial indigoids) were studied, with the remarkable result that most, but not all, members of this class of chromophores quench singlet oxygen at the diffusion limit and some of them are excellent radical traps. It has been shown in this study that a quantitative assessment of antioxidant properties of avonoids, carotenoids, phenols and natural indigoids can be achieved using the following three assays: (1) oxygen pressure dependence; (2) peroxide formation; (3) singlet oxygen quenching. Reactivities towards both excited states and ground state radicals can be properly described by these assays. The remarkable role of b-carotene as an`unusual antioxidant' (Burton GW and Ingold KU, Science 224: 569±573 (1984)) in reactions using various oxygen pressures becomes clearer. The socalled`pro-oxidant effects' concern primarily the antioxidant itself and its degradation, since no or very little damage to the substrate occurs in this type of experiment. Three main categories of antioxidants may be classi®ed: (1) excellent antioxidants that perfectly quench excited states as well as ground state radicals (eg actinioerythrol, astaxanthin); (2) good antioxidants that strongly inhibit peroxide formation but are less ef®cient in quenching excited states (eg¯avonols, tocopherols) or lead to considerable degradation of the antioxidant itself (eg b-carotene, lycopene); (3) moderate antioxidants that fail to excel in both reactivities (eg z-carotene,¯avone).

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“…The quenching rate constant depends on the number of conjugated double bonds present in the molecule. An empirical correlation exists between the , * excitation energy and the carotenoid structure; the quenching ability of carotenoids depends on the excitation energy of their transition at longer wavelengths [14]. Chemical quenching contributes less than 0.05% to the overall quenching of 1 O 2 ; this process is responsible for the final decomposition of carotenoids called bleaching.…”

Section: Introductionmentioning

confidence: 99%

Carotenoids and Protection against Solar UV Radiation

Stahl

Sies²

2002

Skin Pharmacol Physiol

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150

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Upon exposure to UV light photooxidative reactions are initiated which are damaging to biomolecules and affect the integrity of cells and tissues. Photooxidative damage plays a role in pathological processes and is involved in the development of disorders affecting the skin. When skin is exposed to UV light, erythema is observed as an initial reaction. Carotenoids like β-carotene or lycopene are efficient antioxidants scavenging singlet molecular oxygen and peroxyl radicals generated in during photooxidation. When β-carotene was applied as such or in combination with α-tocopherol for 12 weeks, erythema formation induced with a solar light simulator was diminished from week 8 on. Similar effects were also achieved with a diet rich in lycopene. Ingestion of tomato paste corresponding to a dose of 16 mg lycopene/ day over 10 weeks led to increases in serum levels of lycopene and total carotenoids in skin. At week 10, erythema formation was significantly lower in the group that ingested the tomato paste as compared to the control group. No significant difference was found at week 4 of treatment. Thus, protection against UV light-induced erythema can be achieved by ingestion of a commonly consumed dietary source of lycopene. Such protective effects of carotenoids were also demonstrated in cell culture. The in-vitro data indicate that there is an optimal level of protection for each carotenoid.

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Singlet Oxygen Quenching Abilities of Carotenoids

Cited by 58 publications

References 35 publications

Anti- and Prooxidant Properties of Carotenoids

Anti- and Prooxidant Properties of Carotenoids

Quantitative assessment of antioxidant properties of natural colorants and phytochemicals: carotenoids, flavonoids, phenols and indigoids. The role of β‐carotene in antioxidant functions

Carotenoids and Protection against Solar UV Radiation

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