Astaxanthin: Difference between revisions
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'''Astaxanthin''' is a keto-carotenoid within a group of chemical compounds known as terpenes.{{pmid|15823009}} Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups. It is a lipid-soluble pigment with red coloring properties, which result from the extended chain of conjugated (alternating double and single) double bonds at the center of the compound. The presence of the hydroxyl functional groups and the hydrophobic hydrocarbons render the molecule amphiphilic.{{pmid|34371336}} | '''Astaxanthin''' is a keto-carotenoid within a group of chemical compounds known as terpenes.{{pmid|15823009}} Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups. It is a lipid-soluble pigment with red coloring properties, which result from the extended chain of conjugated (alternating double and single) double bonds at the center of the compound. The presence of the hydroxyl functional groups and the hydrophobic hydrocarbons render the molecule amphiphilic.{{pmid|34371336}} | ||
Astaxanthin is produced naturally in the freshwater microalgae ''Haematococcus pluvialis'' and the yeast fungus ''Xanthophyllomyces dendrorhous'' (also known as ''Phaffia rhodozyma'').<ref>{{cite web|title=''Phaffia rhodozyma'' M.W. Mill., Yoney. & Soneda - Names Record|url=http://www.speciesfungorum.org/Names/NamesRecord.asp?RecordID=319694|website=www.speciesfungorum.org|publisher=Species Fungorum|access-date=9 September 2022}}</ref> This vibrant red-orange pigment is synthesized in algae in response to environmental stress factors such as lack of nutrients, increased salinity, or excessive sunlight. In this context, astaxanthin is considered a xenohormetic compound, as its production is a direct response to stress conditions in the microalgae. Animals who feed on the algae, such as salmon, red trout, red sea bream, flamingos, and crustaceans (shrimp, krill, crab, lobster, and crayfish), subsequently reflect the red-orange astaxanthin pigmentation. | Astaxanthin is produced naturally in the freshwater microalgae ''Haematococcus pluvialis'' and the yeast fungus ''Xanthophyllomyces dendrorhous'' (also known as ''Phaffia rhodozyma'').<ref>{{cite web|title=''Phaffia rhodozyma'' M.W. Mill., Yoney. & Soneda - Names Record|url=http://www.speciesfungorum.org/Names/NamesRecord.asp?RecordID=319694|website=www.speciesfungorum.org|publisher=Species Fungorum|access-date=9 September 2022}}</ref> This vibrant red-orange pigment is synthesized in algae in response to environmental stress factors such as lack of nutrients, increased salinity, or excessive sunlight. In this context, astaxanthin is considered a [[Xenohormetic Compounds|xenohormetic compound]], as its production is a direct response to stress conditions in the microalgae. Animals who feed on the algae, such as salmon, red trout, red sea bream, flamingos, and crustaceans (shrimp, krill, crab, lobster, and crayfish), subsequently reflect the red-orange astaxanthin pigmentation. | ||
Astaxanthin is used as a dietary supplement for human, animal, and aquaculture consumption. | Astaxanthin is used as a dietary supplement for human, animal, and aquaculture consumption. | ||
Revision as of 03:58, 13 December 2023
Astaxanthin is a keto-carotenoid within a group of chemical compounds known as terpenes.[1] Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups. It is a lipid-soluble pigment with red coloring properties, which result from the extended chain of conjugated (alternating double and single) double bonds at the center of the compound. The presence of the hydroxyl functional groups and the hydrophobic hydrocarbons render the molecule amphiphilic.[2]
Astaxanthin is produced naturally in the freshwater microalgae Haematococcus pluvialis and the yeast fungus Xanthophyllomyces dendrorhous (also known as Phaffia rhodozyma).[3] This vibrant red-orange pigment is synthesized in algae in response to environmental stress factors such as lack of nutrients, increased salinity, or excessive sunlight. In this context, astaxanthin is considered a xenohormetic compound, as its production is a direct response to stress conditions in the microalgae. Animals who feed on the algae, such as salmon, red trout, red sea bream, flamingos, and crustaceans (shrimp, krill, crab, lobster, and crayfish), subsequently reflect the red-orange astaxanthin pigmentation.
Astaxanthin is used as a dietary supplement for human, animal, and aquaculture consumption.
Legal Status
US
The US Food and Drug Administration has approved astaxanthin as a food color additive for specific uses in animal and fish foods.[4] Astaxanthin from algae, synthetic and bacterial sources is generally recognized as safe in the United States.[5]
EU
The European Commission considers it as a food color additive with E number E161j.[6] The European Food Safety Authority has set an Acceptable Daily Intake of 0.2 mg per kg body weight, as of 2019.[7]
Todo
- 2023, Astaxanthin and meclizine extend lifespan in UM-HET3 male mice; fisetin, SG1002 (hydrogen sulfide donor), dimethyl fumarate, mycophenolic acid, and 4-phenylbutyrate do not significantly affect lifespan in either sex at the doses and schedules used [8]
References
- ↑ Choi S & Koo S: Efficient syntheses of the keto-carotenoids canthaxanthin, astaxanthin, and astacene. J Org Chem 2005. (PMID 15823009) [PubMed] [DOI] Three keto-carotenoids were prepared by the oxidation of the stable C(40) trisulfone 6, which has been used as the key compound in our beta-carotene synthesis. The first allylic oxidation to the unsaturated ketone and the second oxidation to the alpha-hydroxyketone produced the C(40) trisulfones 7 and 10, respectively. The Ramberg-Backlund reaction of the oxidized C(40) trisulfone was efficiently effected by the use of a mild base, NaOMe, in the presence of CCl(4) as a halogenating agent to give the C(40) disulfones 8 and 11. Base-promoted dehydrosulfonation reaction of the disulfone compounds produced the fully conjugated polyenes of canthaxanthin (1), astaxanthin (2), and astacene (3).
- ↑ Ahirwar A et al.: "Light modulates transcriptomic dynamics upregulating astaxanthin accumulation in Haematococcus: A review". Bioresour Technol 2021. (PMID 34371336) [PubMed] [DOI] Haematococcus pluvialis is a green alga that can accumulate high astaxanthin content, a commercially demanding market keto food. Due to its high predicted market value of about 3.4 billion USD in 2027, it is essential to increase its production. Therefore, it is crucial to understand the genetic mechanism and gene expressions profile during astaxanthin synthesis. The effect of poly- and mono-chromatic light of different wavelengths and different intensities have shown to influence the gene expression towards astaxanthin production. This includes transcriptomic gene analysis in H. pluvialis underneath different levels of illumination stress. This review has placed the most recent data on the effects of light on bioastaxanthin production in the context of previous studies, which were more focused on the biochemical and physiological sides. Doing so, it contributes to delineate new ways along the biotechnological process with the aim to increase bioastaxanthin production while decreasing production costs.
- ↑ Phaffia rhodozyma M.W. Mill., Yoney. & Soneda - Names Record, http://www.speciesfungorum.org/Names/NamesRecord.asp?RecordID=319694
- ↑ Summary of Color Additives for Use in United States in Foods, Drugs, Cosmetics, and Medical Devices, https://www.fda.gov/ForIndustry/ColorAdditives/ColorAdditiveInventories/ucm115641.htm See Note 1.
- ↑ Astaxanthin wins full GRAS status. Nutraingredients-usa.com. Retrieved on April 25, 2013.
- ↑ E-numbers : E100- E200 Food Colours. Food-Info.net. Retrieved on April 25, 2013.
- ↑ Safety and efficacy of astaxanthin-dimethyldisuccinate (Carophyll Stay-Pink 10%-CWS) for salmonids, crustaceans and other fish European Food Safety Authority. Retrieved on August 24, 2020.
- ↑ Harrison DE et al.: Astaxanthin and meclizine extend lifespan in UM-HET3 male mice; fisetin, SG1002 (hydrogen sulfide donor), dimethyl fumarate, mycophenolic acid, and 4-phenylbutyrate do not significantly affect lifespan in either sex at the doses and schedules used. Geroscience 2023. (PMID 38041783) [PubMed] [DOI] [Full text] In genetically heterogeneous (UM-HET3) mice produced by the CByB6F1 × C3D2F1 cross, the Nrf2 activator astaxanthin (Asta) extended the median male lifespan by 12% (p = 0.003, log-rank test), while meclizine (Mec), an mTORC1 inhibitor, extended the male lifespan by 8% (p = 0.03). Asta was fed at 1840 ± 520 (9) ppm and Mec at 544 ± 48 (9) ppm, stated as mean ± SE (n) of independent diet preparations. Both were started at 12 months of age. The 90th percentile lifespan for both treatments was extended in absolute value by 6% in males, but neither was significant by the Wang-Allison test. Five other new agents were also tested as follows: fisetin, SG1002 (hydrogen sulfide donor), dimethyl fumarate, mycophenolic acid, and 4-phenylbutyrate. None of these increased lifespan significantly at the dose and method of administration tested in either sex. Amounts of dimethyl fumarate in the diet averaged 35% of the target dose, which may explain the absence of lifespan effects. Body weight was not significantly affected in males by any of the test agents. Late life weights were lower in females fed Asta and Mec, but lifespan was not significantly affected in these females. The male-specific lifespan benefits from Asta and Mec may provide insights into sex-specific aspects of aging.