Cover Picture: 3,3′‐Dihydroxyisorenieratene, a Natural Carotenoid with Superior Antioxidant and Photoprotective Properties (Angew. Chem. Int. Ed. 2/2009)
Hans‐Dieter MartinSebastian KockRoger ScherrersKaya LutterTanja WagenerClaas HundsdörferSusanne FrixelKlaus SchaperHansgeorg ErnstWolfgang SchräderHelmut GörnerWilhelm Stahl
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Abstract:
The red smear cheeses shown on the cover obtain their color from bacteria such as Brevibacterium linens, which contain highly effective antioxidant and photoprotective phenolic carotenoids such as 3,3′-dihydroxyisorenieratene (DHIR). In their Communication on page 400 ff., H.-D. Martin, W. Stahl, and co-workers describe the synthesis of DHIR and their investigation of its antioxidative and photoprotective properties. Its quinoid oxidation product is blue in color.Keywords:
Brevibacterium
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Surprisingly, neither the precise pharmacological effect nor the toxicological profile is usually established for food components. Carotenoids are no exception in this regard. Only limited insight into the pharmacology and toxicology of carotenoids exists. It is known that the antioxidant action of carotenoids is determined by 1. electron transfer reactions and the stability of the antioxidant free radical, 2. the interplay with other antioxidants and 3. the reaction with active oxygen. Numerous metabolites of carotenoids are formed upon their action as an antioxidant. Most of these metabolites have an unknown biological activity. It is concluded that a severe lack of knowledge hampers adequate suggestions for human supplementation.
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Adequate photoprotection is essential to control UV-related disorders, including sunburn, photoaging and photocarcinogenisis. Sun avoidance, protection of skin with clothing, and sunscreens are presently the best way of photoprotection, assuming that they are used properly. However, new strategies, which are based on or make use of the endogenous protective response to UV light, may further improve currently used photoprotective means. The addition of repair enzymes and/or antioxidants has a positive effect on skin's recovery from UV-induced DNA-damage. Several botanical agents, mainly vitamins and polyphenols, have shown to influence signal transduction pathways leading to photoprotective effects. Also stimulation of endogenous UV-response pathways via irradiation with a low UV dose or via simulation of UV-induced DNA-damage results in photoprotective effects. Future research in this field and combination of different photoprotective strategies will hopefully lead to improved photoprotection.
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PCR-Based Methodology for the Determination of the Photoprotection Afforded by Sunscreen Application
We have applied a PCR-based methodology to study the DNA damage induced by UV-A, UV-B and sunlight itself. Our results, employing a cell-free system, indicate that UV-B (310 nm) is approximately 30-fold more potent at inhibiting DNA synthesis than UV-A (365 nm). We were also able to show that 20 min of sunlight exposure on a summer day induced DNA damage capable of inhibiting DNA synthesis. Hence, this methodology has a sensitivity suitable to detect biologically relevant doses of UV light. In addition, we propose that this technique may be suitable to assess the relative photoprotection of commercially available sunscreens. We present here preliminary data on the photoprotection afforded by the topical application of sunscreen. This photoprotection was measured by a reduction in the subsequent UV-B- and UV-A-induced DNA damage when sunscreen was applied. Our results demonstrate that the particular sunscreen tested was effective against both UVB and UV-A. However, the estimated photoprotective factor of the sunscreen (against both UV-A and UV-B) was approximately tenfold less than the stated Sun Protection Factor (SPF) of 25. This methodology may also be useful in identifying new photoprotective agents by assessing their relative value as UV-B and UV-A absorbing agents.
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Carotenoids are secondary plant constituents and more than 700 different compounds have been identified. They are synthesized by plants, where they serve as colorants for fruits and leaves, bacteria, fungi and algae. In nature carotenoids are important biological compounds due to their provitamin A activity, antioxidant properties and accessory functions in the light harvesting system of plants. Considerable amounts of carotenoids are ingested with the diet and accumulate in the human organism. α- and β- carotene, β- cryptoxanthin, lutein, zeaxanthin and lycopene are the major carotenoids in human blood and tissues. Based on their structural features carotenoids are suitable compounds for photoprotection in humans. They may act as ultraviolet (UV) absorbers and dietary antioxidants capable of scavenging reactive intermediates generated under the condition of photooxidative stress. Photooxidative stress is involved in processes of photoageing, photocarcinogenesis and plays a major role in the pathogenesis of photodermatoses. Intervention studies with β- carotene and lycopene supplements or diets rich in those carotenoids have shown that these molecules contribute to systemic photoprotection ameliorating UVinduced erythema. In- vitro data provide evidence that also other carotenoids are efficient photoprotectors, for example lutein and the structurally unusual phenolic polyene 3,3- dihydroxyisorenieratene. Keywords: Carotenoids, UV, photoprotection, skin, DHIR
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Carotenoids are well known for their contribution to the vibrant coloration of many animals and have been hypothesized to be important antioxidants. Surprisingly few examples of carotenoids acting as biologically relevant antioxidants in vivo exist, in part because experimental designs often employ dosing animals with carotenoids at levels that are rarely observed in nature. Here we use an approach that reduces carotenoid content from wild-type levels to test for the effect of carotenoids as protectants against an oxidative challenge. We used the marine copepod, Tigriopus californicus reared on a carotenoid-free or a carotenoid-restored diet of nutritional yeast and then exposed them to a prooxidant. We found that carotenoid-deficient copepods not only accumulated more damage, but also were more likely to die during an oxidative challenge than carotenoid-restored copepods. We suggest that carotenoid reduction, and not supplementation, better tests the proposed roles of carotenoids in other physiological functions in animals.
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ABSTRACT Adequate photoprotection is essential to control UV‐related disorders, including sunburn, photoaging and photocarcinogenisis. Sun avoidance, protection of skin with clothing, and sunscreens are presently the best way of photoprotection, assuming that they are used properly. However, new strategies, which are based on or make use of the endogenous protective response to UV light, may further improve currently used photoprotective means. The addition of repair enzymes and/or antioxidants has a positive effect on skin's recovery from UV‐induced DNA‐damage. Several botanical agents, mainly vitamins and polyphenols, have shown to influence signal transduction pathways leading to photo‐protective effects. Also stimulation of endogenous UV‐response pathways via irradiation with a low UV dose or via simulation of UV‐induced DNA‐damage results in photo‐protective effects. Future research in this field and combination of different photoprotective strategies will hopefully lead to improved photoprotection.
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Carotenoids are micronutrients present mainly in fruits and vegetables, and they are ingested from these sources with the diet. They exhibit specific antioxidant activity but also influence signaling and gene expression at the cellular level. β‐Carotene and lycopene, the colorants of carrots and tomatoes, respectively, are among the most prominent members of this group of lipids, and they are usually the dominating carotenoids in human blood and tissues. Both compounds modulate skin properties when ingested as supplements or as dietary products. There is evidence that they protect the skin against sunburn (solar erythema) by increasing the basal defense against UV light‐mediated damage. Their photoprotective efficacy, however, is not comparable to the use of a sunscreen. In vitro data show that also other carotenoids are efficient photoprotectors. Among them are lutein and structurally unusual phenolic polyenes like 3,3′‐dihydroxyisorenieratene.
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