Astaxanthin

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Astaxanthin
Astaxanthin.svg
IUPAC name
Other names 3,3'-dihydroxy-ß-carotene-4,4'-dione
Identifiers
CAS number 472-61-7 Yes check.svgY
PubChem 5281224
SMILES
InChI
InChI key MQZIGYBFDRPAKN-QISQUURKBE
ChemSpider ID 4519704
Properties
Molecular formula C40H52O4
Molar mass 596.84 g/mol
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Astaxanthin (pronounced as-tuh-zan'-thin) is a carotenoid. It belongs to a larger class of phytochemicals known as terpenes. It is classified as a xanthophyll, which means "yellow leaves". Like many carotenoids, it is a colorful, lipid-soluble pigment. Astaxanthin is produced by microalgae, yeast, salmon, trout, krill, shrimp, crayfish, crustaceans, and the feathers of some birds.[1][2] Professor Basil Weedon was the first to map the structure of astaxanthin.

Astaxanthin, unlike some carotenoids, does not convert to Vitamin A (retinol) in the human body. Too much Vitamin A is toxic for a human, but astaxanthin is not. However, it is a powerful antioxidant; it is claimed to be 10 times more capable than other carotenoids.[3] However, other sources suggest astaxanthin has slightly lower antioxidant activity than other carotenoids.[4]

While astaxanthin is a natural nutritional component, it can be found as a food supplement. The supplement is intended for human, animal, and aquaculture consumption. The commercial production of astaxanthin comes from both natural and synthetic sources.

The U.S. Food and Drug Administration (FDA) approved astaxanthin (See: Regulations below) as a food coloring (or color additive) for specific uses in animal and fish foods[5]. The European Union (actually European Commission) considers it food dye within the E number system, E161j[6].

Contents

[edit] Natural sources

The following sources are being used for the commercial production of astaxanthin.

As a natural source, the following can be found in nature (or a production facility) with the approximate concentrations listed.

Amounts of astaxanthin found in different organisms[7]
Natural Astaxanthin Sources Astaxanthin Concentration(ppm)
Salmonids
Plankton
Krill
Arctic shrimp
Phaffia Yeast
Haematococcus pluvialis
 ~ 5
~ 60
~ 120
~ 1200
~ 8000
~40,000

Currently, the primary natural source for astaxanthin is Haematococcus pluvialis (microalgae)[8]. It seems to accumulate the highest levels of astaxanthin in nature[9]; commercially more than 40g of astaxanthin per kilo of dry biomass.[10] It has the advantage of the population doubling every week, which means scaling up is not an issue; simply open another plant. However, it does require some expertise to grow the algae with a high astaxanthin content. Specifically, the microalgae is grown in two phases. First, in the green phase, the cells are given an abundance of nutrients to promote proliferation of the cells. In the subsequent red phase, the cells are deprived of nutrients and subjected to intense sunlight to induce encystment, during which the cells produce high levels of astaxanthin as a protective measure against the environmental stress. The cells, with their high concentrations of astaxanthin, are then harvested.[11]

Xanthophyllomyces dendrorhous (a yeast) has similar advantages, but requires refrigeration once harvested (above freezing, <6 degrees Celsius/43 degrees Fahrenheit). It also has the problem of being low in nutritional value, unlike krill or shrimp. Since it is not ocean-based, it has the issue of not carrying those ocean-like traits[such as?]. Since its chief advantage is price, it will certainly be available for the cost-conscious consumer.[citation needed]

For obtaining astaxanthin from Euphausia superba (Antarctic krill), this report from aquafeed.com points to some of the issues:

Krill

The Krill fishing operation is complex. It is done in Antarctic waters, under extreme weather conditions and far away from ports with substantial operational complexities. Krill's fishing location and the difficult weather conditions in the main fishing area, together with the costs involved in the operation, have contributed to a slow development of the industry. Krill fishing is by far different to any other fishing operation today known. The knowledge to work with it belongs to very few people in the world.

P. borealis

[edit] Synthetic sources

Synthetic production of astaxanthin is generally not preferred because synthetic astaxanthin contains a mixture of stereoisomers, astaxanthin is fairly abundant and obtainable in certain natural sources, and consumers prefer natural products over synthetic ones.[12]

Today, essentially all commercial astaxanthin for aquaculture is produced synthetically from petrochemical sources, with an annual turnover of over $200 million, and a selling price of ~$2000 per kilo of pure astaxanthin. [10]

Producers of synthetic astaxanthin
Brand Name Producer Source
Carophyll Pink 10% CWS* DSF Carophyll Pink 10% CWS -
Lucantin Pink BASF Salmon farming: Ensuring transparency from the fish farm to the supermarket shelf -
  • Formerly Carophyll Pink - certified by AFAQ (1993/1015) - in use since 1985[14] - product purchased from HR in 2003.[13] [14]

[edit] Difference between natural and synthetic forms

Astaxanthin has two chiral centers, at the 3 and 3' positions. Therefore, there are three stereoisomers; (3-R,3'-R), (3-R,3'-S) (meso), and (3-S,3'-S). Synthetic astaxanthin contains a mixture of the three, in approximately 1:2:1 proportions. Naturally occurring astaxanthin varies considerably from one organism to another. The astaxanthin in fish is of whatever stereoisomer the fish ingested.[15] The astaxanthin produced by haematococcus pluvialis, which is commonly used in the feed of animals which are in turn consumed by humans, is the (3-S,3'-S) stereoisomer.[16]

[edit] Uses

In 1948, Nobel prizewinner George Wald surmized, "This could lead to an important new use of astaxanthin as a drug delivery for medicines that are insoluble in water, and give designers of new food colourants or dyestuffs an interesting new capability."[17]

Astaxanthin is used as a feed supplement for salmon, crabs, shrimp, chickens and egg production.[18] Regardless of the source, astaxanthin provides some important benefits beyond coloration. It also has been found to be essential for proper growth and survival.[10]

[edit] For seafood and animals

The primary use of synthetic astaxanthin today is as an animal feed additive to impart coloration, this includes farm-raised salmon and egg yolks.[10] In that, synthetic carotenoid (i.e., coloured yellow, red or orange) pigments represent about 15-25% of the cost of production of commercial salmon feed.[19] Today, essentially all commercial astaxanthin for aquaculture is produced synthetically from petrochemical sources, with an annual turnover of over $200 million, and a selling price of ~$2000 per kilo of pure astaxanthin. [10]

[edit] For humans

Currently, the primary use for humans is as a food supplement. Research shows that due to astaxanthin's potent antioxidant activity, it may be beneficial in cardiovascular, immune, inflammatory and neurodegenerative diseases.[9] Some sources have demonstrated its potential as an anti-cancer agent.[20] Research supports the assumption that it protects body tissues from oxidative damage.[21][22] It also crosses the blood-brain barrier, which makes it available to the eye, brain and central nervous system to alleviate oxidative stress that contributes to ocular, and neurodegenerative diseases such as glaucoma and Alzheimer's.[23]

[edit] The farm-raised salmon lawsuit

The class action lawsuits were filed against some major grocery store chains for not clearly labeling the salmon "color added".[24] The chains follow up quickly by labeling all such salmon as "color added". "However, Smith & Lowney persisted with the suit for damages, but a Seattle judge dismissed (...)(the case) , ruling that enforcement of the applicable food laws was up to government and not individuals."[25]

[edit] Astaxanthin in the food chain

It has been speculated that gulls are "flushed" pink when molting, especially in areas with farm-raised salmon.[26] However, those speculating admit they don't know why, not enough is known about[27] the relationship between astaxanthin and plumage.

[edit] Regulations

In April 2009, the US FDA approved astaxanthin as an additive to fish feed only as a component of a stabilized color additive mixture. Color additive mixtures for fish feed use made with astaxanthin may contain only those dilutents that are suitable.[5] The color additives astaxanthin, ultramarine blue, canthaxanthin, synthetic iron oxide, dried algae meal, Tagetes meal and extract, and corn endosperm oil are approved for specific uses in animal foods (see 21 CFR 73.35,73.50, 73.75, 73.200, 73.275, 73.295, 73.315, respectively). Haematococcus algae meal (21 CFR 73.185) and Phaffia yeast (21 CFR 73.355) for use in fish feed to color salmonoids were added in 7/6/2000.[28][29][30]

FDA ledger on applications for
New Dietary Ingredients in Dietary Supplements 1999-2001

In the European Union, astaxanthin containing food supplements, derived from sources which have no history of use as a source of food in Europe, fall under the remit of the Novel Food legislation, EC (No.) 258/97. Since 1997, there have been five novel food applications concerning products which contain astaxanthin extracted from these novel sources. In each case, these applications have been simplified or substantial equivalence applications, because astaxanthin itself is recognised as a food component in the EU diet.[31][32][33][34]

[edit] Trivia

  • There are over 600 known carotenoids. 100 different carotenoids are generally encountered in foods.[1] About half of the roughly 50 carotenoids in the human diet are absorbed into the blood stream.[35]
  • Astaxanthin has 100-500 times the antioxidant capacity of Vitamin E and 10 times the antioxidant capacity of beta-carotene. Many laboratory studies also indicate astaxanthin is a stronger antioxidant than lutein, lycopene and tocotrienols.[23] However, other studies have demonstrated the antioxidant capacity of astaxanthin to be comparable to or slightly less than that of other carotenoids.[36]
  • Synthetic astaxanthin fetches $2000 a kilogram on the market, while the natural product is sold for over $7000 a kilo.[37]
Salmon roe at the Shiogama seafood market in Japan
  • Lobsters, shrimp, and some crabs turn red when cooked because the astaxanthin, which was bound to the protein, unwinds.[38]
  • Cardinals seem to produce astaxanthin from carotenoids when molting, even when fed primarily seed with natural yellow dye.[39]
  • While it constitutes a tiny portion of salmon feed (50 to 100 parts per million), astaxanthin represents a major share of the cost, up to 20 percent.[24]

[edit] References

  1. ^ a b Carotenoid Introductory
  2. ^ Carotenoid - See: Astaxanthin
  3. ^ Phytochemicals: Astaxanthin
  4. ^ Mortensen, A.; Skibsted, L. H. (1997), "Importance of carotenoid structure in radical scavenging reactions", J. Agric. Food Chem. 1997, 45 (8): 2970−2977, doi:10.1021/jf970010s.
  5. ^ a b "Summary of Color Additives for Use in United States in Foods, Drugs, Cosmetics, and Medical Devices". http://www.fda.gov/ForIndustry/ColorAdditives/ColorAdditiveInventories/ucm115641.htm.  See Note 1.
  6. ^ - Currently unlisted. Will look for a better ref.
  7. ^ http://algatech.com/astax.htm
  8. ^ Haematococcus pluvialis
  9. ^ astafactor.com Algae
  10. ^ a b c d e astafactor.com Astax
  11. ^ Boussiba; Sammy, V.; Avigad, C.; et al. (2000) Procedure for large-scale production of astaxanthin from haematococcus. U. S. Patent 6,022,701.
  12. ^ Boussiba; Sammy, V.; Avigad, C.; et al. (2000) Procedure for large-scale production of astaxanthin from haematococcus. U. S. Patent 6,022,701.
  13. ^ "Did Good: Astaxanthin". 10 Oct 2006. http://www.didgood.com/recipes/information/salmon/astaxanthin/astaxanthin.html. 
  14. ^ "DSM Nutritional Products - History". http://www.dsm.com/en_US/html/dnp/about_history.htm. Retrieved 16 Oct 2009. 
  15. ^ US patent application 20050014824 (online here) (also EP patent 1442083)
  16. ^ Boussiba; Sammy, V.; Avigad, C.; et al. (2000) Procedure for large-scale production of astaxanthin from haematococcus. U. S. Patent 6,022,701.
  17. ^ Radford, Tim (30 July 2002). "Scientists find why lobsters turn red when cooked". The Guardian. http://www.guardian.co.uk/uk_news/story/0,3604,765263,00.html. Retrieved 18 July 2009. 
  18. ^ - just the egg part
  19. ^ Fisheries and Oceans Canada - Aquaculture Issues
  20. ^ Palozza, P.; Torelli, C.; Boninsegna, A.; Simone, R.; Catalano, A.; Mele, M. C.; Picci, N. (2009), "Growth-inhibitory effects of the astaxanthin-rich alga Haematococcus pluvialis in human colon cancer cells", Cancer Lett. 283, (1): 108-117, doi:10.1016/j.canlet.2009.03.031
  21. ^ NIH:PubMed
  22. ^ Guerin, Martin; Huntley, Mark E.; Olaizola, Miguel (2003), Haematococcus astaxanthin: applications for human health and nutrition, Trends in Biotechnology, pp. 210–212, http://www.cyanotech.com/pdfs/bioastin/batl09.pdf 
  23. ^ a b Astaxanthin - Frequently Asked Questions, 2005, http://www.beta-glucan-info.com/astaxanthin-questions-answers.htm, retrieved 16 May 2008 
  24. ^ a b Smith & Lowney - Farm-raised Salmon Coloring, 2003, http://www.smithandlowney.com/salmon/, retrieved 14 Oct 2009 
  25. ^ "Pigments in Salmon Aquaculture: How to Grow a Salmon-colored Salmon". Archived from the original on 13 Oct 2007}. http://web.archive.org/web/20071013221146/http://seafoodmonitor.com/sample/salmon.html. Retrieved 18 July 2009. 
  26. ^ McGraw, Kevin; Hardy, Lisa (2006) (pdf), Astaxanthin is responsible for the pink plumage flush in Franklin's and Ring-billed gulls, Tempe, AZ: School of Life Sciences, Arizona State University, pp. 5, http://www.public.asu.edu/~kjmcgraw/pubs/JFO2006.pdf 
  27. ^ "Notes on the effects of Astaxanthin on the plumage of birds". 2006. http://www.didgood.com/recipes/information/salmon/astaxanthin/research-Bird-Plumage/pdf.html. Retrieved 19 July 2009. 
  28. ^ Code of Federal Regulations Title 21 §73.35 FDA decision on Astaxanthin
  29. ^ http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=73.185 Code of Federal Regulations Title 21 §73.185 FDA decision on Haematococcus algae meal
  30. ^ Food Additive Status List 2009
  31. ^ UK novel food application
  32. ^ UK novel food application
  33. ^ UK novel food application
  34. ^ UK novel food application
  35. ^ http://www.benbest.com/nutrceut/phytochemicals.html#carotenoids
  36. ^ Mortensen, A.; Skibsted, L. H. (1997), "Importance of carotenoid structure in radical scavenging reactions", J. Agric. Food Chem. 1997, 45 (8): 2970−2977, doi:10.1021/jf970010s.
  37. ^ Leora Eren Frucht (8 May 2005). "Israel grows red algae in the desert to fight disease". http://www.israel21c.org/index.php?option=com_content&view=article&id=1068:israel-grows-red-algae-in-the-desert-to-fight-disease&catid=58:environment&Itemid=101. Retrieved 14 Oct 2009. 
  38. ^ http://www.ochef.com/718.htm
  39. ^ http://www.colorado.edu/chemistry/chem5181/HP_GCMS_Paper2.pdf

Note: Must align numbers.

[edit] External links

v • d • e
Carotenoids
Carotenes (C40)
Xanthophylls (C40)
Apocarotenoids (C<40)
Vitamin A retinoids (C20)
Retinoid drugs
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