Cis astaxanthin and especially 9-cis astaxanthin exhibits a higher antioxidant activity in vitro compared to the all-trans isomer

Liu, Xuebo; Osawa, Toshihiko

doi:10.1016/j.bbrc.2007.03.120

Cited by 197 publications

(143 citation statements)

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“…In the xanthophylls, oxygen may be present as hydroxyl groups, carbonyl groups or as a combination of both, as seen in astaxanthin 22 . The presence of hydroxyl (OH) and carbonyl (C=O) in each ionone ring (Figure 1) explains some of the features of astaxanthin, such as the ability to be esterified, a more polar nature and a high antioxidant capacity 5 .…”

Section: Chemical Structure Of Astaxanthinmentioning

confidence: 99%

“…Most carotenoids found in nature are trans isomers. Thermodynamically, the all-trans-astaxanthin is more stable than other cis isomers 24 but they may be isomerized from one form to another when exposed to light, heat, acid or metal ions 5 . Due to the presence of two stereogenic carbon atoms at the C3 and C3' position, there are three stereoisomers for astaxanthin: a pair of enantiomers (3R,3'R-and 3S,3'S-astaxanthin) and an optically inactive mesoform (3R,3'S-astaxanthin).…”

Section: Chemical Structure Of Astaxanthinmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…By belonging to the class of carotenoids called xanthophylls, astaxanthin shares many of the metabolic and physiological activities attributed to carotenoids; however, astaxanthin has other peculiar chemical properties owing to its molecular structure 5 . The presence of hydroxyl and carbonyl functional groups in ketocarotenoids, like astaxanthin, makes them excellent antioxidants 5,6 . The high antioxidant power of astaxanthin has shown beneficial effects on various diseases related to oxidative damage, such as hypertension 7 , obesity 8 , macular degeneration 9 and cancer 10,11 .…”

Section: Introductionmentioning

confidence: 99%

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Astaxanthin: structural and functional aspects

Seabra

Pedrosa

2010

Rev. Nutr.

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1 Article based on L.M.J. SEABRA' s thesis project entitled "Litopenaeus vannamei shrimp: components of nutritional importance in meat and processing waste. A B S T R A C TAstaxanthin, a carotenoid belonging to the xanthophyll class, has stirred great interest due to its antioxidant capacity and its possible role in reducing the risk of some diseases. Astaxanthin occurs naturally in microalgae, such as Haematococcus pluvialis and the yeast Phaffia rhodozyma, and has also been considered to be the major carotenoid in salmon and crustaceans. Shrimp processing waste, which is generally discarded, is also an important source of astaxanthin. The antioxidant activity of astaxanthin has been observed to modulate biological functions related to lipid peroxidation, having beneficial effects on chronic diseases such as cardiovascular disease, macular degeneration and cancer. Researches have shown that both astaxanthin obtained from natural sources and its synthetic counterpart produce satisfactory effects, but studies in humans are limited to natural sources. There is no established nutritional recommendation regarding astaxanthin daily intake but most studies reported beneficial results from a daily intake of 4mg. Thus, this review discusses some aspects of the carotenoid astaxanthin, highlighting its chemical structure and antioxidant activity, and some studies that report its use in humans.Indexing terms: Antioxidants. Astaxanthin. Carotenoids. Chronic diseases. R E S U M O

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Section: Chemical Structure Of Astaxanthinmentioning

confidence: 99%

Section: Chemical Structure Of Astaxanthinmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Astaxanthin: structural and functional aspects

Seabra

Pedrosa

2010

Rev. Nutr.

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“…It also exhibits anti-infl ammatory and immunostimulatory action [Goswami et al 2010, Pashkow et al 2008, Yuan et al 2011. The benefi cial effect of astaxanthin is related to the presence of coupled double bonds in the long hydrocarbon chain as well as polar hydroxyl and carbonyl groups in both ionone rings [Liu and Osawa 2007]. Due to its unique chemical structure: polarnonpolar-polar, astaxanthin can react with phospholipid head groups or water in the aqueous environment, quenching radicals from the surface of or inside the lipid bilayer of cell membrane [Pashkow et al 2008].…”

Section: Introductionmentioning

confidence: 99%

Astaxanthin synthesis by Xanthophyllomyces dendrorhous DSM 5626 and its astaxanthin overproducing mutants on xylose media under diferent illumination

Stachowiak

2014

Acta Sci Pol Technol Aliment

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Background. Astaxanthin is the most important and expensive carotenoid pigment used in aquaculture. Its commercial attractiveness is also related with its antioxidant potential. Xanthophyllomyces dendrorhous yeast is considered to be promising for commercial production of astaxanthin. The aim of this study was to investigate the possibility of the growth and astaxanthin production by X. dendrorhous strains on media containing xylose under different illumination. Material and methods. X. dendrorhous DSM 5626 and its mutants: 10BE and 26UV were used in this study. The cultures were carried out on hydrolysed rye stillage (HS) and YM medium with xylose (YM-K). Cell concentration, total carotenoid and astaxanthin yields were assessed in 5-day cultures. The effect of illumination in the range of 0-5,000 lx on growth and on astaxanthin production of yeasts in cultures run on YM-K medium was also examined. Results. For the tested yeast strains better growth parameters and astaxanthin yields were obtained on the YM-K medium, on which for all strains the highest pigment yields were recorded at 600-1,000 lx. The highest concentration of astaxanthin in cells was recorded for 26UV in a culture at 1,000 lx (0.51 g·kg -1 DCW). The volume yield of the pigment regardless of strain was highest in cultures at 600 lx. In this case 10BE was found to be the best astaxanthin producer with a yield of 2.15 mg·dm -3 . Conclusions. Astaxanthin synthesis in X. dendrorhous DSM 5626 and its mutants was better on YM-K medium comparing to hydrolysed rye stillage. Moreover, carotenogenesis in the studied yeast strains was subjected to marked photoregulation. Illumination within the range of 600-1,000 lx promotes carotenogenesis and astaxanthin production, while exceeding a certain light capacity results in microbial cell death.

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Ergothioneine: a potential antioxidative and antimelanosis agent for food quality preservation

Kitsanayanyong

Ohshima

2022

FEBS Letters

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The global population increase has increased the demand for food products. However, post-harvest deterioration because of oxidation and discoloration results in a drastic loss of food quality and supply. Thus, research has focused on developing strategies to minimize such losses. One of those strategies includes the application of ergothioneine (ET), a potent hydrophilic antioxidant, to several food products to overcome their short shelf-life. ET can be synthetic or derived from several species of edible mushrooms and their extracts, which are known sources of natural ET. Given the reported potential of ET in food quality preservation, this review compiles the recent applications of ET as a preservative for maintaining the quality of food commodities.

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Cis astaxanthin and especially 9-cis astaxanthin exhibits a higher antioxidant activity in vitro compared to the all-trans isomer

Cited by 197 publications

References 23 publications

Astaxanthin: structural and functional aspects

Astaxanthin: structural and functional aspects

Astaxanthin synthesis by Xanthophyllomyces dendrorhous DSM 5626 and its astaxanthin overproducing mutants on xylose media under diferent illumination

Ergothioneine: a potential antioxidative and antimelanosis agent for food quality preservation

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