Carotenoids astaxanthin

An excellent case in point is the coloration of the American lobster, Homarus americanus. The pigment associated with the typical greenish-brown outer layer of the lobster shell is the carotenoid, astaxanthin (Figure A), an oxygenated derivative of p-carotene, also known as the molecule that imparts the orange color to carrots. 

This work demonstrated that an airlift system was suitable for the cultivation of Haematococcus pluvialis, one of the most effective microorganisms that could produce high potential antioxidant carotenoid, astaxanthin. Aeration was shown to be crucial for a proper growth of the alga in the airlift bioreactor, but it must be maintained at low level, and the most appropriate superficial velocity was found to be at the lower limit of the pump, i.e. 0.4 cm s". ... 

Yokoyama, A. Shizuri, Y. Misawa, N. (1998) Production of new carotenoids, astaxanthin glucosides, by Escherichia coli transformants carrying carotenoid biosynthaic genes. Tetrahedron Lett., 39,3709-12. 

Goto, S. et al.. Efficient radical trapping at the surface and inside the phospholipid membrane is responsible for highly potent antiperoxidative activity of the carotenoid astaxanthin, Biochim. Biophys. Acta, 1512,251,2001. 

Tanaka, T. et al, Chemoprevention of mouse urinary bladder carcinogenesis by the naturally occurring carotenoid astaxanthin. Carcinogenesis, 15, 15, 1994. 

Tanaka, T., Morishita, Y., Suzui, M., Kojima, T., Okumura, A., and Mori, H. (1994). Chemo-prevention of mouse urinary bladder carcinogenesis by the naturally occurring carotenoid astaxanthin. Carcinogenesis 15,15-19. 

Lobster and shrimp dine on plankton that contain carotenoids, and the compounds become concentrated in their shells. There, they are bound up with protein molecules, and the carotenoid-protein complex is dark green. Cooking the shellfish heats the protein and denatures it. In other words, the protein breaks down and disassociates itself from the reddish carotenoid, astaxanthin, which then becomes visible. To a lesser extent, this process is also evident when we cook carrots — they become more orange than they were in their raw state. The effect is not as great as it is with shrimp and lobster, because carrots do not have much protein. 

Crustacean shells consist of 30-40% proteins, 30-50% calcium carbonate, and 20-30% chitin and also contain pigments of a lipidic nature such as carotenoids (astaxanthin, canthaxanthin, lutein, and p-carotene). These proportions vary with species and with season. On the other hand, chitin is associated with a higher protein content but lower carbonate concentration. Chitin is extracted by acid treatment to dissolve the calcium carbonate followed by alkaline extraction to dissolve the proteins and by a depigmentation step to obtain a colorless product mainly by removing the astaxanthin [102]. 

P, P-carotenoid astaxanthin (Table 8). p,p-Carotene and some other carotenoids are vitamin A active as they are degraded to vitamin A aldehyde in the human and mammal organism trans-cis isomerization of vitamin A aldehyde bound to the protein opsin in rhodopsin in the retina of the eyes is the key step of the visual process (section 4.2). As non-toxic natural compounds giving no cause for concern, P,P-carotene and some other carotenoids are used as coloring agents for foods and cosmetics, and/or as vitamin A precursors and antioxidants in medicines. 

Carotenoids astaxanthin beta-carotene canthaxanthin lutein zeaxanthin Chlorella sp. Dunaliella salina Haematococcus pluvialis Spirulina sp. antioxidant properties cancer prevention cardiovascular protection DNA damage protection eye and skin protection glycation inhibition immune system enhancement inflammation prevention neuroprotection 53, 54... 

Carotenoids (astaxanthin, d- and -carotene, lutein, and -cryptoxandiin) were separated on a C30 column (photodiode array detector, X = 250-600 nm in line with positive ion electrosprty MS) using a 60-min 85/15 10/90 medianoI/MlBE all... 

CCI3O2 reacts with ascorbic and uric acid [71], as well as bilirubin [72] and glutathione [73] via electron transfer. However, with tryptophan and carotenoids another reaction also occurs, suggested to be radical addition [74, 75]. For the carotenoids the proposed adduct decays to yield more radical cation and for the carotenoid, astaxanthin, the radical cation is not formed initially but is formed solely through the proposed addition radical [75]. The one electron reduction potential of astaxanthin radical cation has been shown to be higher than several other carotenoids [76], so it may be that it is very close to that of CCI3O2 so that electron transfer is very slow. 

Terpene hydroquinones which are well known as constituents of other marine organisms have been isolated from the ascidian Aplidium constellatum, (750). These compounds demonstrated activity as anticancer agents. In the case of A. constellatum, 2-methyl-2-(4-methylpent-3-enyl)-2/f-chromen-6-ol could be identified. Five new carotenoids have been obtained from tunicates, halocynthiaxanthin (1067) (751) and mytiloxanthinone (1068) (752) from Halocynthia roretzi, sidnyax-anthin (1069) from Sidnyum argus (755) and amarouciaxanthin A (1070) and B (1071) from Amaroucium pliciferum (733a). Halocynthia aurantium furnished two known carotenoids, astaxanthin and diatoxan-... 

Fig. 3. Commeicially important carotenoids P-caiotene (10), canthaxanthin [514-78-3] (11), astaxanthin [472-61-7] (12), P-apo-8 -caiotenal [1107-26-2] (13), P-apo-8 -caiotenoic acid ethyl ester [1109-11-1] (14), and citranaxanthin [3604-90-8] (15).

MISAWA N, SATOMI Y, KUNDON K, YOKOYAMA A, KAJIWARA S, SATO T, OHTANI T and MIKI W (1995) Strncture and functional analysis of a marine bacterial carotenoid biosynthetic gene clnster and astaxanthin biosynthetic pathway proposed at the gene eveV, J Bacteriol, 177, 6575-84. 

It has been established that carotenoid structure has a great influence in its antioxidant activity for example, canthaxanthin and astaxanthin show better antioxidant activities than 3-carotene or zeaxanthin. 3- 3 3-Carotene also showed prooxidant activity in oil-in-water emulsions evaluated by the formation of lipid hydroperoxides, hexanal, or 2-heptenal the activity was reverted with a- and y-tocopherol. Carotenoid antioxidant activity against radicals has been established. In order of decreasing activity, the results are lycopene > 3-cryptoxanthin > lutein = zeaxanthin > a-carotene > echineone > canthaxanthin = astaxanthin. ... 

Anon., 2002. Carotenoids What are carotenoids What do carotenoids do Astaxan-thin Biochemical Properties, Mera Pharmaceuticals, Inc. October 1, 2006. www.astaxanthin.org/carotenoids.htm. 

Higuera-Ciapara, L, Felix-Valenzuela, L., and Goycoolea, R, Astaxanthin a review of its chemistry and applications, Crit. Rev. Food Sci. Nutr. 46, 185, 2006. Voutilainen, S. et ah. Carotenoids and cardiovascular health. Am. J. Clin. Nutr. 83, 1265, 2006. 

Hussein, G. et ah, Astaxanthin, a carotenoid with potential in human health and nutrition, J. Nat. Prod. 69, 443, 2006. 

Some of the advantages of astaxanthin over other carotenoids include (1) better stability compared to other carotenoids, (2) high antioxidant potential (10 times... 

This pigment is recognized by the U.S. Food and Drug Administration (21 Code of Federal Regulations, Part 73) as a color additive exempted from certification (Subpart A, Foods, Section 73.35, Astaxanthin). Formulations containing astaxanthin include soft gelatin capsules containing 100 mg equivalents of total carotenoids, a skin care... 

Astaxanthin (3,3-dihydroxy-p,p-carotene-4,4-dione) is widely distributed in Nature and is the principal pigment in crustaceans and sahnonids. The carotenoid imparts distinctive orange-red coloration to the animals and contributes to consumer appeal in the market place. 

Since animals cannot synthesize carotenoids, the pigments must be supplemented in the feeds of farmed species. Salmon and trout farming is now a huge business and feeding studies have shown that astaxanthin is very effective as a flesh pigmenter ... 

Jyonouchi, H., Sun, S., and Gross, M., Effect of carotenoids on in vitro immunoglobulin production by human peripheral blood mononuclear cells astaxanthin, a carotenoid without vitamin A activity, enhances in vitro immunoglobulin production in response to a T-dependent stimulant and antigen, Nutr. Cancer, 23, 171, 1994. 

Jyonouchi, H. et al., Studies of immunomodulating actions of carotenoids. I. Effects of P-carotene and astaxanthin on murine lymphocyte functions and cell surface marker expression in in vitro culture system, Nutr. Cancer, 19, 93, 1991. 

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