天然アスタキサンチン   天然アスタキサンチン
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アスタキサンチンの概要
アスタキサンチンの化学
アスタキサンチンの製法
アスタキサンチンの抗酸化作用
生理活性
アスタキサンチンの代謝
安全性
産業への利用
特許その他
関連文献・研究
アスタキサンチンの概要
天然界での存在
アスタキサンチンの化学
アスタキサンチンの製法
活性酸素およびアスタキサンチンの抗酸化作用
生理活性
アスタキサンチンの代謝
安全性
産業への利用


アスタキサンチンの概要

関連文献・研究  (アスタキサンチンの概要)

総説

1) Kuhn, R., Soerensen, N.A. : The coloring matters of the lobster (Astacus gammarus L.), Z. Angew.
Chem.,1938, 51, 465-466.
2) 日本水産学会編 : 水産動物のカロテノイド, 水産学シリーズ25, 1978, 恒星社厚生閣,東京.
3) Kamata T. : Chemistry of astaxanthin, 鹿児島県立短期大学紀要 自然科学編, 1990, 41, 29-43.
4) 細川雅史 : アスタキサンチン, 水産食品栄養学ー基礎からヒトへー, 鈴木平光,和田俊,三浦理代編著, 2004, 技術堂出版,東京.
5) Johnson, E.A., An, G.-H. : Astaxanthin from microbial sources, Critical Reviews in Biotechnology, 1991, 11, 297-326.

 

天然界での存在

関連文献・研究 (天然界での存在)

水産物

1)幹渉 : 海洋生物のカロテノイド-代謝と生物活性, 水産学シリーズ[94],日本水産学会, 1993北水試、試験
研究は今、323号、漁業系廃棄物に関する共同研究について(1997.10.31).
 
アスタキサンチンの分布
1) Tischer, J. : Carotenoids of fresh-water algae V. The carotenoids of H. pluvialis, Z. Physiol. Chem., 1938, 252, 225-233.
2) Tischer, J. : Carotenoids of fresh-water algae VI. The epiphasic carotenoids and a colorless accompanying substance of some red Euglena species, Z. Physiol. Chem., 1939, 259, 163-170.
3) Kessler, E., Czygan, F. : Chlorela zofingiensis Donz, Isolerung neuer stamme und ihre physiologisch-
biochemischen eigenschaften, Ber. Deuts. Botani. Gesell., 1965, 78, 343-347.
4) Andrewes, A.G., Phaffia, H.J., Starr, M.P. : Carotenids of Phaffa rhodozyma, a red pigmented fermenting yeast, Phytochem., 1976, 15, 1003-1007.
5) Burgess, M.L., Barrow, K.D., Gao, C., Heard, G.M., Glenn, D. : Carotenoid glycoside esters from the
thermophilic bacterium Meiothermus ruber, J. Nat. Prod., 1999, 62, 859-863.
6) Manunta, C. : Astaxanthin and other terrestrrrial arthropods, Nature, 1948, 162, 298.
7) Cheesman, D.F. : Ovorubin, a chromoprotein from the eggs of the gastropod mollusc Pomacea
cancaliculata, Proc. Roy. Soc. B, 1958, 149, 571-587.
8) Czeczuga, B. : Astaxanthin ester, a dominating carotenoid in Taenia saginata (Cestoidea), Bull. Acad. Pol. Sci. Biol., 1975, 23, 829-832.
9) Czeczuga, B. : Astaxathin, a dominating carotenoid in four species of leeches, Bull. Acad. Pol. Sci. Biol., 1977, 25, 85-87.
10) Kuhn, R., Soerensen, N.A. : The coloring matters of the lobster (Astacus gammarus L.), Z. Angew. Chem., 1938, 51, 465-466.
11) Hartmann, M., Medem, F.G., Kuhn, R., Bielig, H.-J. : Investigation of gamones of the rainbow trout, Z.
Naturforsch., 1947, 2b, 330-349.
12) De Nicola, M. : Carotenoids of the carapace of the echinoderm, Ophidiaster ophidianus, Biochem. J., 1954, 56, 555-558.
13) De Nicola, M. : Astaxanthin in asteroid echinoderms Asterina panceri, Exp. Cell. Res., 1956, 10,
441-446.
14) Fox, D.L., Crozier, G.F. : Astaxanthin in the blue oceanic barnacle Lepas fascicularis, Experientia, 1967, 23, 12-13.
15) Grangaud, R., Massonet, R. : Research on the biogenesis of the vitamin A of fish. I. Astaxanthin,
provitamin A for Gambusia holbrooki Grd, Arch. Sci. Physiol. (Paris), 1955, 9, 245-256.
16) Hata, M., Hata, M. : Carotenoid pigments in goldfish IV. Carotenoid metabolism, 日水誌, 1972, 38, 331.
17) Hata, M., Hata, M. : Carotenoid metabolism in fancy red carp. Cyprinus carpio-I Administration od
carotenoids, 日水誌, 1975, 41, 653.
18) Khare, A., Moss, G.P., Weedon, B.C., Matthews, A.D. : Identification of astaxanthin in Scottish salmon, Comp. Biochem. Physiol. B, 1973, 45, 971-973.
19) Katayama, T., Miyahara, T., Tanaka, T., Sameshuma, S., Simpson, K.L., Chichester, C.O. : The
biosynthesis of Astaxanthin -XV. The carotenoids in Chidai, red sea bream, Eoynnis japonica Tanaka and the incorporation of labelled astaxanthin from the diet of the red sea bream} to their body astaxanthin, Bull. Jap. Soc. Sci. Fish., 1974, 40, 97-103.
20) Czeczuga, B. : Carotenoids in fish. 5. Anguilla anguilla(L), Acta Hydrobiol., 1975, 17, 311-317.
21) Miki, W., Yamaguchi, K., Konosu, S. : Comparison of cartenoides in the ovaries of marine fish and
shellfish, Comp. Biochem. Physiol. B, 1982, 71, 7-11.
22) Czeczuga, B. : Carotenoids in Fish. XXXII. Content of carotenoids in eggs utilized in the form of caviar, Folia Histochem. Cytochem.(Krakow), 1982, 20, 63-68.
23) Yamaguchi, K., Miki, W., Toriu, N., Kondo, Y., Murakami, M., Konosu, S., Satake, M., Fujita, T. : The
composition of carotenoid pigments in the antarctic krill Euphausia superba, Bull. Jap. Sos. Sci. Fish.,
1983, 49, 1411-1415.
24) Maoka, T.,Yokoi, S., Matsuno, T. : Comparative biochemical studies of carotenoids in nine species of cephalopoda, Comp. Biochem. Physiol., 1989, 92, 247-250.
25) Gv, Neumann, H.J., Loevenich, H.K. : The nature of the oil droplets and visual substance, Arch. ges.
Physiol., 1943, 246, 652-663.
26) Volker, O. : Isolation of lutein from feathers, and the detection of astaxanthin in the plumage of certain birds, Hoppe Seylers Z. Physiol. Chem., 1951, 288, 20-24.
27) Fox, D.L. : Astaxanthin in the American flamingo, Nature, 1955, 175, 942-943.
28) Goldsmith, T.H., Collins, J.S., Licht, S. : The cone oil droplets of avian retinas, Vision Res., 1984, 24,
1661-1671.
29) Grangaud, R., Garcia, I., Massoent, R. : Presentation of evidence for astaxanthin in Triton nodifer,
Compt. Rend., 1952, 235, 446-448.
30) Lipetz, L.E. : Pigment types, densities and concentrations in cone oil droplets of Emydoidea blandingii, Vision Res., 1984, 24, 605-612.
31) Seybold, A., Goodwin, T.W. : Occurrence of astaxanthin in the flower petals of Adonis annua L., Nature, 1959, 184, 1714-1715.

魚類
1) GOODWIN,T.W. : Biochemistry of the Carotenoids, vol 2, Animals (CHAPMAN and HALL, London,
244 pp (1984).
2) 幹渉,藤田孝夫 : 魚類のカロテノイド代謝, 化学と生物, 1985, 23, 640〜648.
3) Khare, A., Moss, G.P., Weedon, B.C., Matthews, A.D. : Identification of astaxanthin in Scottish salmon,
Comp. Biochem. Physiol. B, 1973, 45, 971-973.
4) Craik, Z.C.A. : Egg quality ans egg pigment content in salmonid fish, Aquaculture, 1985, 47, 61-68.
5) 松野隆男,幹渉 : 動物におけるカロテノイドの生理機能と生物活性, 化学と生物, 1990, 28, 219-227.
6) Katayama T. et al : The biosynthesis of Astaxanthin -XV. The carotenoids in Chidai, red sea bream,
Eoynnis japonica Tanaka and {the incorporation of labelled astaxanthin from the diet of the red sea bream} to their body astaxanthin, Bull. Jap. Soc. Sci. Fish, 1974, 40, 97-103.
7) Hata, M., Hata, M. : Carotenoid metabolism in fancy red carp. Cyprinus carpio-I Administration od
carotenoids, 日水誌, 1975, 41, 653.
8) Hata, M., Hata, M. : Carotenoid pigments in goldfish IV. Carotenoid metabolism, 日水誌, 1972, 38, 331.
9) 日本水産学会編 : 水産動物のカロテノイド, 水産学シリーズ25, 1978, 恒星社厚生閣,東京

甲殻類
1) Kuhn, R., Soerensen, N.A. : The coloring matters of the lobster (Astacus gammarus L.), Z. Angew. Chem.,1938, 51, 465-466.
2) De Nicola,M. : Carotenoids of the carapace of the echinoderm, Ophidiaster ophidianus, Biochem. J., 1954, 56, 555-558.
3) Yamaguchi,K., Miki,W., Toriu, N., Kondo,Y., Murakami,M., Konosu,S., Satake,M., Fujita,T. : The
composition of carotenoid pigments in the antarctic krill Euphausia superba, Bull. Jap. Sos. Sci. Fish,
1983, 49, 1411-1415.
4) Cheesman, D.F., Prebble, J. : Astaxanthin ester as a prosthetic group: a carotenoprotein from the hermit crab, Comp. Biochem. Physiol., 1966, 17, 929-935.
5) Katayama, T., Kamata, T., Shimaya, M., Deshimsru, O., Chichester, C.O. : The biosynthesis of
Astaxanthin -VIII. The conversion of labelled β-carotene-15 15'-3H2 into astaxanthin in Prawn, Penaeus japonicus Bate, Bull. Jap. Soc. Sci. Fish, 1972, 38, 1171-1172.
6) Coral-Hinostroza,G.N., Bjerkeng,B. : Astaxanthin from the red crab langostilla (Pleuroncodes planipes):
optical R/S isomers and fatty acid moieties of astaxanthin esters, Comp. Biochem. Physiol. B Biochem. Mol. Biol., 2002, 33, 437-444

無脊椎動物
1) Fox, D.L., Crozier, G.F. : Astaxanthin in the blue oceanic barnacle Lepas fascicularis, Experientia, 1967, 23, 12-13.
2) De Nicola,M. : Astaxanthin in asteroid echinoderms Asterina panceri, Exp. Cell Res., 1956, 10, 441-446.
3) Maoka,T.,Yokoi,S., Matsuno,T. : Comparative biochemical studies of carotenoids in nine species of
cephalopoda, Comp. Biochem. Physiol., 1989, 92, 247-250.
4) Cianci,M., Rizkallah,P.J., Olczak,A., Raftery,J., Chayen,N.E., Zagalsky,P.F., Helliwell,J.R. : Structure of
lobster apocrustacyanin A1 using softer X-rays, Acta Crystallogr. D Biol. Crystallogr., 2001, 57, 1219-1229.

Haematococcus pluvialis
1) Kakizono, T., Kobayashi, M., Nagai, S. : Effect of Carbon/Nitrogen Ratio on Encystment Accompanied with
Astaxanthin Formation in a Green Alga, Haematococcus pluvialis, J. Ferment. Bioeng., 1992, 74, 403-405.
2) Fan, L., Vonshak, A., Boussiba, S. : Effect of temperature and irradiance on growth of Haematococcus plubialis, J. Phycol.,1994, 30, 829-833.
3) Tischer,J. : Carotenoids of fresh-water algae V. The carotenoids of H. pluvialis, Z. Physiol. Chem., 1938, 252, 225-233.
4) Tischer,J. : Carotenoids of fresh-water algae IX. The carotenoids of H. pluvialis, Z. Physiol. Chem., 1911, 281, 143-155.
5) 山下栄次 : 緑藻類ヘマトコッカス藻によるアスタキサンチンの工業的生産とその利用, 農化, 2002, 76,
740-743
6) Misawa, N. : Carotenoid biosynthesis at the gene level, Dynamic Aspects of Natural Products Chemistry, ed. Ogura, K., Sankawa, U., 1997, p49-p72, Kodansha, Tokyo, Japan and Harwood Academic Publishers, Amsterdam, The Netherlands.

Phaffia rhodozyma
1) Phaff, H.J. : My life with yeasts, Annu. Rev. Microbiol., 1986, 40, 1-28.
2) Andrewes, A.G., Phaffia, H.J., Starr, M.P. : Phytochem., 1976, 15, 1003-1007.
3) Johnson EA, Villa TG, Lewis MJ, Phaff HJ. : Simple method for the isolation of astaxanthin from the basidiomycetous yeast Phaffia rhodozyma, Appl. Environ. Microbiol., 1978, 35, 1155-1159.
4) Ramirez, J., Gutierrez, H., Gschaedler, A. : Optimization of astaxanthin production by Phaffia rhodozyma through factorial design and response surface methodology, J. Biotechnol., 2001, 88, 259-268.
5) Andrewes, A.G., Starr, M.P. : (3R,3'R)-Asttaxanthin from the yeast Phaffa rhodozyma, Phytochem., 1976, 15, 1009-1011.
6) Andrewes, A.G., Phaffia, H.J., Starr, M.P. : Carotenids of Phaffa rhodozyma, a red pigmented fermenting yeast, Phytochem., 1976, 15, 1003-1007.

その他の微生物
1) Eric, S., Johnson, Gil-Hwan An : Astaxanthin from Microbial Sources, Critical Reviews in Biotechnology, 1991, 11, 297-326.
2) Tischer, J. : Carotenoids of fresh-water algae VI. The epiphasic carotenoids and a colorless accompanying substance of some red Euglena species, Z. Physiol. Chem., 1939, 259, 163-170
3) Yokoyama, A., Izumida, H., Miki, W. : Production of astaxanthin and 4-ketozeaxanthin by the marine
bacterium, Agrobacterium aurantiacum, Biosci. Biotechnol. Biochem., 1994, 58, 1842-1844.
4) Pane, L., Radin, L., Franconi, G., Carli, A. : The carotenoid pigments of a marine Bacillus firmus strain, Boll. Soc. Ital. Biol. Sper., 1996, 72, 303-308.
5) Yamaoka, Y., Carmona, M.L., Oota, S. : Growth and Carotenoid Production of Thraustochytrium sp.
CHN-1 Cultured under Superbright Red and Blue Light-emitting Diodes, Biosci. Biotechnol. Biochem.,
2004, 68, 1594-1597.
6) Tsuboura, A., Yoneda, H., Mizut, H. : A new aerobic Gram-negative astaxanthin-producing bacterium, Int. J. System. Bacteriol., 1999, 49, 277-282.
7) Lee, J.H., Kim, Y.S., Choi, T.J., Lee, W.J., Kim, Y.T. : Paracoccus haeundaensis sp. nov., a Gram-negative, halophilic, astaxanthin-producing bacterium, Int. J. Syst. Evol. Microbiol., 2004, 54, 1699-1702.

その他の生物
1) Sludnitz, Gv., Neumann, H.J., Loevenich HK : The nature of the oil droplets and visual substance, Arch. ges. Physiol., 1943, 246, 652-663.
2) Manunta, C. : Astaxanthin and other terrestrrrial arthropods, Nature, 1948, 162, 298.
3) Volker, O. : Isolation of lutein from feathers, and the detection of astaxanthin in the plumage of certain birds, Hoppe Seylers Z. Physiol. Chem., 1951, 288, 20-24.
4) Grengaud, R., Gaaarcia, I., Massoent, R. : Presentation of evidence for astaxanthin in Triton nodifer,
Compt. Rend., 1952, 235, 446-448.
5) Fox, D.L. : Astaxanthin in the American flamingo, Nature, 1955, 175, 942-943.
6) Seybold, A., Goodwin, T.W. : Occurrence of astaxanthin in the flower petals of Adonis annua L., Nature, 1959, 184, 1714-1715.
7) Czeczuga, B. : Astaxanthin ester, a dominating carotenoid in Taenia saginata (Cestoidea), Bull. Acad. Pol. Sci. Biol., 1975, 23, 829-832.
8) Czeczuga, B. : Astaxathin, a dominating carotenoid in four species of leeches, Bull. Acad. Pol. Sci. Biol., 1977, 25, 85-87.
9) Lipetz, L.E. : Pigment types, densities and concentrations in cone oil droplets of Emydoidea blandingii, Vision Res., 1984, 24, 605-612

 

アスタキサンチンの化学

関連文献・研究 (アスタキサンチンの化学)

化学構造・合成
1) Kuhn, R., Soerensen, N.A. : The coloring matters of the lobster (Astacus gammarus L.), Z. Angew. Chem.,1938, 51, 465-466.
2) Cheesman, D.F. : Ovorubin, a chromoprotein from the eggs of the gastropod mollusc Pomacea canaliculata, Proc. Roy. Soc. B, 1958, 149, 571-587.
3) Davies, B.H. : In “Chemistry and Biochemistry of Plant Pigments”, T. W. Goodwin ed., 2nd ed., 38-165, Academic Press, NY, 1976.
4) Yamaguchi,K., Miki,W., Toriu, N., Kondo,Y., Murakami,M., Konosu,S., Satake,M., Fujita,T. : The
composition of carotenoid pigments in the antarctic krill Euphausia superba, Bull. Jap. Sos. Sci. Fish.,
1983, 49, 1411-1415.
5) Renstrom, B., Liaaen-Jensen, S. : Fatty acids of some esterified carotenols, Comp. Biochem. Physiol. B, Comp. Biochem., 1981, 69, 625-627.
6) Andrewes, A.G., Starr, M.P. : (3R,3'R)-Asttaxanthin from the yeast Phaffa rhodozyma, Phytochem., 1976, 15, 1009-1011.
7) Andrewes, A.G., Phaffia, H.J., Starr, M.P. : Carotenids of Phaffa rhodozyma, a red pigmented fermenting yeast, Phytochem., 1976, 15, 1003-1007.
8) Surmatis, J.D., Thommen. R. : A total synthesis of astaxanthin dimethyl ether, J. Org. Chem., 1967, 32, 180-184.
9) Kienzle von, F., Mayer, H. : Synthesis of optically active natural carotenoids and structurally related
compounds. II. Syntheesis of(3S,3'S)-asthaxanthin, Helv. Chim. Acta, 1978, 61, 2609-2615.
10) Jacobs, P.B., LeBoeuf, R.D., McCommas, S.A., Tauber, J.D. : The cleavage of carotenoid ester by
cholesterol esterase, Comp. Biochem. Physiol., 1982, 72B, 157-160.
11) Liu, J., Colmenares, L.U., Liu, R.S.H. : Fluorinated Astaxanthins, Tetrahedron Lett., 1997, 38,
8495-8498.
12) Showalter,L.A., Weinman,S.A., OSterlie,M., Lockwood,S.F. : Plasma appearance and tissue accumulation of non-esterified, free astaxanthin in C57BL/6 mice after oral dosing of a disodium disuccinate diester of astaxanthin (Heptax trade mark ), Comp. Biochem. Physiol. C Toxicol. Pharmacol., 2004, 137, 227-36.
13) Coral-Hinostroza,G.N., Bjerkeng,B. : Astaxanthin from the red crab langostilla (Pleuroncodes planipes): optical R/S isomers and fatty acid moieties of astaxanthin esters, Comp. Biochem. Physiol. B Biochem.
Mol. Biol., 2002, 33, 437-444.

安定性
1) Christophersen, A.G., Jun, H., Jorgensen, K., Skibsted, L.H. : Photobleaching of astaxanthin and
canthaxanthin. Quantum-yields dependence of solvent, temperature, and wavelength of irradiation in
relation to packaging and storage of carotenoid pigmented salmonoids, Z. Lebensm. Unters Forsch., 1991, 192, 433-439.
2) Yuan,j.P.,Chen,F. : Isomerization of trans-astaxanthin to cis-isomers in organic solvents, J. Aagric. Food Chem., 1999, 47, 3656-3660.
3) Yuan, J.P., Chen, F. : Hydrolysis kinetics of astaxanthin esters and stability of astaxanthin of
Haematococcus pluvialis during saponification, J. Agric. Food Chem., 1999, 47, 31-35.
4) Yuan, j.P.,Chen, F. : Isomerization of trans-Astaxanthin to cis-Isomers in Organic Solvents, J. Agric. Food Chem., 1999, 47, 3656-3660.
5) Mortensen, A., Skibsted, L.H. : Kinetics and mechanism of the primary steps of degradation of carotenoids by acid in homogeneous solution, J. Agric. Food Chem., 2000, 48, 279-286.

色調・結合
1) 中川平介 : カロテノプロテン, 水産動物のカロテノイド,日本水産学会編, 1972, 90-107.
2) Cheesman, D.F. : Ovorubin, a chromoprotein from the eggs of the gastropod mollusc Pomacea
cancaliculata, Proc. Roy. Soc. B, 1958, 149, 571-587.
3) Cheesman, D.F., Prebble, J. : Astaxanthin ester as a prosthetic group: a carotenoprotein from the hermit crab, Comp. Biochem. Physiol., 1966, 17, 929-935.
4) Henmi, H., Hata, M., Takeuchi, M. : Studies on the carotenoids in the muscle of salmon--V. Combination of astaxanthin and canthaxanthin with bovine serum albumin and egg albumin, Comp Biochem Phsiol, 1991, 99, 609-612.

アスタキサンチン蛋白の構造
1) Lee, T.Y., Jung, J., Song, P. : Spectroscopic characterization of alpha-crustacyanin, J. Biochem. (Tokyo), 1980, 88, 663-668.
2) Merlin, J.C., Thomas, E.W., Shone, C.C., Britton, G. : Resonance Raman study of reconstituted
carotenoproteins incorporating astaxanthin and 15,15'-dide-hydro-astaxanthin, Biochim. Biophys. Acta,
1987, 913, 111-116.
3) Cianci,M., Rizkallah,P.J., Olczak,A., Raftery,J., Chayen,N.E., Zagalsky,P.F., Helliwell,J.R.: Structure of
lobster apocrustacyanin A1 using softer X-rays, Acta Crystallogr. D Biol. Crystallogr., 2001, 57, 1219-1229.
4) Krawczyk, S., Britton, G. : A study of protein-carotenoid interactions in the astaxanthin-protein
crustacyanin by absorption and Stark spectroscopy; evidence for the presence of three spectrally distinct species, Biochim. Biophys. Acta, 2001, 1544, 301-310.

アスタキサンチンの生合成
1)Misawa N:Carotenoid Biosynthesis at the Gene Level, Dynamic Aspects of Natural Products Chemistry,
Molecular Biological Approaches(ed. Ogura K and Sankawa U), Koddansha Ltd. Tokyo and Harword
Academic Publishers,The Netherland,1997, 49-72
2) Lotan,T., Hirschberg,J.: Cloning and expression in Escherichia coli of the gene encoding
beta-C-4-oxygenase, that converts beta-carotene to the ketocarotenoid canthaxanthin in Haematococcus pluvialis, FEBS Lett., 1995, 364, 125-128.
3) Misawa N, Satomi Y, Kondo K, Yokoyama A, Kajiwara S, Saito T, Ohtani T, Miki W.: Structure and
functional analysis of a marine bacterial carotenoid biosynthesis gene cluster and astaxanthin
biosynthetic pathway proposed at the gene level, J. Bacteriol., 1995, 177, 6575-6584.
4) Kajiwara,S., Kakizono,T., Saito,T., Kondo,K., Ohtani,T., Nishino,N., Nagai,S., Misawa,N. : Isolation and
functional identification of a novel cDNA for astaxanthin biosynthesis from Haematococcus pluvialis, and astaxanthin synthesis in Escherichia coli, Plant Mol. Biol., 1995, 29, 343-353.
5) Fraser,P.D., Miura,Y., Misawa ,N. : In Vitro Characterization of Astaxanthin Biosynthetic Enzymes, J. Biol. Chem., 1997, 272, 6128-6135.
6) Misawa,N., Shimada,H. : Metabolic engineering for the production of carotenoids in non-carotenogenic bacteria and yeasts, J. Biotechnol., 1997, 59, 169-181.
7) Linden,H. : Carotenoid hydroxylase from Haematococcus pluvialis: cDNA sequence, regulation and
functional complementation, Biochim. Biophys. Acta, 1999, 1446, 203-212.
8) Fraser,P.D., Shimada,H, Misawa,N. : Enzymic confirmation of reactions involved in routes to astaxanthin formation, elucidated using a direct substrate in vitro assay, Eur. J. Biochem., 1998, 252, 229-236.
9) Mann,V., Harker,M., Pecker,I., Hirschberg,J. : Metabolic engineering of astaxanthin production in tobacco flowers, Nature Biotechnol., 2000, 18, 888-892.

アスタキサンチンの測定
1) Sestak, Z., Baslerova, M. : Changes in chlorophylls and carotenoids in ageing culture of green algae as studied by paper chromatography, in Studies of microalgae and photosynthetic bacteriaed, by Japanese Society of Plant Physiologists.The Univ. of Tokyo, pp.423-429, 1963.
2) 桑野和民, 酒巻千波, 三田村敏男 : Separation of astaxanthin from the antarctic krill by HPLC, 東京家政学院大学紀要, 1988, 28, 53-56.
3) van Breemen, R.B., Hung, C.R., Tan, Y.C. : LC/MS of carotenoids using atmospheric pressure chemical ionization, J. Mass Spec., 1996, 31, 975-982.
4) Abu-Lafi, S., Turujamn, S.A. : A chiral HPLC method for the simultaneous separetion of configurational isomers of the predominant cis/trans forms of astaxanthin, Enantiomer, 1997, 2, 17-25.
5) Turujman, S.A., Wamer, W.G., Wei, R.R., Albert, R.H. : Rapid liquid chromatographic method to
distinguish wild salmon from aquacultured salmon fed synthetic astaxanthin, J AOAC Int ., 1997, 80,
622-632.
6) Careri, M., Elviri, L., Mangia, A. : Liquid chromatography-electrospry mass spectrometry of beta-carotene and xanthophylls. Validation of the analytical method, J. Chromatogr. A, 1999, 854, 233-244.
7) Dachtler, M., Glaser, T., Kohler, K., Albert, K. : Combined HPLC-MS and HPLC-NMR on-line coupling for the separation and determination of lutein and zeaxanthin stereoisomers in spinach and in retina, Anal. Chem., 2001, 73, 667-674.
8) Takaichi, S., Matsui, K., Nakamura, M., Muramatsu, M., Hanada, S. : Fatty acids of astaxanthin esters in krill determined by mild mass spectrometry, Comp. Biochem. Physiol. B Biochem. Mol. Biol., 2003, 136, 317-322.

 

アスタキサンチンの製法


関連文献・研究 (アスタキサンチンの製法)

Haematococcus pluvialis 
1) Osterlie, M., Bjerkeng, B., Liaaen-Jensen, S.:Plasma appearance and distribution of astaxanthin E/Z and R/S isomers in plasma lipoproteins of men after single dose administration of astaxanthin, J. Nutr. Biochem., 2000, 11, 482-490.
2) Renstrom, B., Borech, G., Skulberg, O., Liaaen-Jensen, S. : Optical purity of (3S,3′S)-astaxanthin fromHaematococcus pluvialis, Phytochemistry, 1981, 20, 2561-2564.
3) Andrewes, A.G., Starr, M.P. : (3R,3'R)-Asttaxanthin from the yeast Phaffa rhodozyma, Phytochem., 1976, 15, 1009-1011.
4) Bubrick, P. : Production of Astaxanthin from Haematococcus, Bioresour Technol., 1991, 38, 237-239.
5) Kobayashi, M., Kakizono, T., Yamaguchi, K., Nishio, N., Nagai, S. : Growth and astaxanthin formation of
Haematococcus pluvialis in heterotrophic and mixotrophic conditions, J. Ferment. Bioeng., 1992, 74,
17-20.
6) Kobayashi, M., Kakizono, T., Nishio, N., Nagai, S. : Effect of light intesity , light quality, and illumination cycle on astaxanthin formation in a green alga, Haematococcus pluvialis, J. Ferment. Bioeng., 1992, 74, 61-63.
7) Kakizono, T., Kobayashi, M., Nagai, S. : Effect of carbon/nitrogen ratio on encystment accompanied with astaxanthin formation in a green alga, Haematococcus pluvialis, J. Ferment. Bioeng., 1992, 74, 403-405.
8) Kobayashi, M., Kakizono, T., Nagai, S. : Enhanced carotenoid biosynthesis by oxdative stress in
acetate-induced cyst cells of a green unicellular alga, Haematococcus pluvialis, Appl. Environ. Microbiol., 1993, 59, 867-873.
9) Tjahjono, A.E., Hayama, Y., Kakizono, T., Terada, Y., Nishino, N., Nagai, S. : Hyper-accumulation of
astaxanthin in a green alga Haematococcus pluvialis at elevated temperatures, Biotechnol. Lett., 1994, 16, 133-138.
10) Tjahono, A.E., Kakizonnno, T., Hayama, Y., Nishino, N., Nagai, S. : Isolation of resistant mutants against carotenoid biosynthesis inhibitors for a green alga Haematococcus pluvialis, and their hybrid formation by protoplast fusion for breeding of higher astaxanthin producers, J. Ferment. Bioeng., 1994, 77, 352-357.
11) Chumpolkulwong, N., Kakizono, T., Handa, T., Nishio, N. : Isolation and characterization of compactin
resistant mutants of an astaxanthin synthesizing green alga Haematococcus pluvialis, Biotechnol Lett.,
1997, 19, 299-302.
12) Zhang, X.W., Gong, X., Chen, F. : Kinetic models for astaxanthin production by high density mixotrophic culture of the microalga Hematococcus pluvialis, J. Indust. Microbiol. Biotecnol., 1999, 23, 691-696.
13) Fabregas, J., Dominguez, A., Regueiro, M., Maseda, A., Otero, A. : Optimization of culture medium for the continuous cultivation of the microalga Haematococcus pluvialis, Appl. Microbiol. Biotechnol., 2000, 53, 530-535.
14) Fabregas, J., Otero, A., Maseda, A., Dominguez, A. : Tow-stage culture for the production of astaxanthin from Haematococcus pluvialis, J. Biotechnol., 2001, 89, 65-71.
15) Pirt, S.J., Lee, Y.K., Walch, M.R., Pirt, M.W., Balyuzi, H.H.M., Bazin, M.J. : A tubular bioreactor for
photosynthetic production of biomass from carbon dioxide: design and performance, J. Chem. Tech.
Biotecnol., 1983, 33, 35-58.
16) 平林征四郎 : 微細藻類培養装置, 日本特許, 2003, 第3462508号.

Phaffia rhodozyma 
1)ohnson, E.A., Villa, T.G., Lewis, M.J., Phaff, H.J. : Simple method for the isolation of astaxanthin from
the basidiomycetous yeast Phaffia rhodozyma, Appl. Environ. Microbiol., 1978, 35, 1155-1159.
2)An, G.H., Johnson, E.A. : Influence of light on growth and pigmentation of the yeast Phaffia rhodozyma,Antonie Van Leeuwenhoek, 1990, 57, 191-203.
3)Lewis, M.J., Ragot, N., Berlant, M.C., Miranda, M. : Selection of astaxanthin-overproducing mutants of
Phaffia rhodozyma with β-ionone, Appl. Environ. Microbiol., 1990, 56, 2944-2945.
4)An, G.H., Bielich, J., Auerbach, R., Johnson, E.A. : Isolation and characterization of carotenoid
hyperproducing mutants of yeast by flow cytometry and cell sorting, Biotechnology (N Y), 1991, 9, 70-73.
5)Fang, T.J., Cheng, Y.S. : Isolation of astaxanthin over-producing mutants of Phaffia rhodozyma and their fermentation kinetics, Zhonghua Min Guo Wei Sheng Wu Ji Mian Yi Xue Za Zhi, 1992, 25, 209-222.
6)Vazquez, M., Martin, A.M. : Optimization of Phaffia rhodozyma continuous culture through response
surface methodology, Biotechnol. Bioeng., 1998, 57, 314-320.
7)Parajo, J.C., Santos, V. V., Vazquez, M. : Production of carotenoids by Phaffia rhodozyma growing on
media made from hemicellulosic hydrolysates of eucalyptus globulus wood, Biotechnol. Bioeng., 1998, 59, 501-506.
8)Flores-Cotera, L.B., Maartin, R., Sanchez, S. : Citrate, a possible precursor of astaxantin in Phaffia
rhodozymea: influence of varying levels of ammonium, phosphate and citrate in a chemically defined
medium, Appl. Microbiol. Biotechnol., 2001, 55, 341-347.
9)An, G.H., Choi, E.S. : Preparation of the red yeast, Xanthophyllomyces dendrorhous, as feed additive
with increased availability of astaxanthin, Biotechnol. Lett., 203, 25, 767-771.
10) Dominguez-Bocanegra, A.R., Torres-Munoz, J.A. : Astaxanthin hyperproduction by Phaffia rhodozyma (now Xanthophyllomyces dendrorhous) with raw coconut milk as sole source of energy, Appl. Microbiol. Biotechnol., 2003, 66, 249-252.
11) Echavarri-Erasun, C., Johnson, E.A. : Stimulation of astaxanthin formation in the yeast
Xanthophyllomyces dendrorhous by the fungus Epicoccum nigrum, FEMS Yeast Res., 2004, 4, 511-519.
12) Johnson, E.A. : Phaffia rhodozyma: colorful odyssey, Int. Microbiol., 2003, 6, 169-174.

オキアミ Euphausia superba
1)Yamaguchi, K., Miki, W., Toriu, N., Kondo, Y., Murakami, M., Konosu, S., Satake, M., Fujita, T. : The
composition of carotenoid pigments in the antarctic krill Euphausia superba, Bull. Jap. Sos. Sci. Fish.,
1983, 49, 1411-1415.
2)山下栄次 : オキアミ由来スタキサンチンの色素沈着抑制効果, Fregnance J., 1995, 14, 180-185.
3)勝山政明, 谷敏文 : 日本特許, 1993, 特開平5-155739.

 

活性酸素およびアスタキサンチンの抗酸化作用

関連文献・研究 (活性酸素およびアスタキサンチンの抗酸化作用)

1)中野稔、浅田浩二、大柳善彦編:活性酸素 生物での生成・消去・作用の分子機構、新装版,1993、共立出版(株)、東京.

一重項酸素(1O2)
1) Di Mascio, P., Devasagayam, T.P., Kaiser, S., Sies, H. : Carotenoids, tocopherols and thiols as biological singlet molecular oxygen quenchers, Biochem. Soc. Trans., 1990, 18, 1054-1056.
2) Kobayashi, M., Sakamoto, Y. : Singlet oxygen quenching ability of astaxanthin esters from the green alga Haematococcus pluvialis., Biotechnol. Lett., 1999, 21, 265-269.
3)Tatuzawa, H., Maruyama, T., Misawa, N., Fujimori, K., Nakano, M. : Quenching of singlet oxygen by
carotenoids produced in Escherichia coli-attenuation of singlet oxygen-mediated bacteria killing by
rotenoids., FEBS Lett., 2000, 484, 280-284.

脂質過酸化
1) Terao, J. : Antioxidant activity of beta-carotene related carotenoids in solution, Lipids, 1989, 24, 659-662.
2) 幹渉,藤田孝夫:魚類のカロテノイド代謝, 化学と生物, 1985, 23, 640〜648.
3) Palozza, P., Krinsky, N.I. : Astaxanthin and canthaxanthin are potent antioxidantss in a membrane model, Arch. Biochem. Biophys., 1992, 297, 291-295.
4) Lim, B.P., Nagao, A., Terao, J., Tanaka, K., Suzuki, T., Takama, K.:Antioxidant activity of xantho-phylls on peroxyl radical-mediated phospholipid peroxidation, Biochim. Biophys. Acta, 1992, 1126, 178-184.
5) Jorgensen, K., Skibsted, L.H. : Carotenoid scavenging of radicals. Effect of carotenoid structure and
oxygen partial pressure on antioxidative activity, Z. Lebensm. Unters. Forsch., 1993, 196, 423-429.
6) Barros, M.P., Pinto, E., Colepicolo, P., Pedersen, M. : Astaxanthin and peridinin inhibit oxidative damage in Fe++-loaded liposomes:Scavenging oxyradicals or changing membrane permeability?, Biochem. Biophys. Res. Commun., 2001, 288, 225-232.
7) Goto, S., Kogure, K., Abe, K., Kimata, Y., Kitahama, K., Yamashita, E., Terada, H. : Efficient radical
trapping at the surface and inside the phospholipid membrane is responsible for highly potent antioxidative activity of the carotenoid astaxanthin, Biochim. Biophys. Acta, 2001, 1512, 251-258.
8) Shibata, A., Kiba, Y., Akati, N., Fukuzawa, K., Terada, H. : Molecular characteristics of astaxanthin and
beta-carotene in the phospholipid monolayer and their distributions in the phospholipid bilayer, Chem.
Phys. Lipids, 2001, 113, 11-22.

 

生理活性

関連文献・研究 (生理活性)

-基礎-
視覚系

1) Kirschfeld, K. : Carotenoid pigments-their possible role in protecting against photooxidation in eyes and photoreceptor cells, Proc. R. Soc. Lond. B, 1982, 216, 71-85.
2) Schalch, W. : Carotenoids in the retina - a review of their possible role in preventing or limiting damage caused by light and oxygen, Free radicals and Aging, ed. I. Emerit & B. Chance,1992, 280-298, Brikhaeuser Verlag, Basel, Switzerland.
3) Tso, M.O.M., Lam, T.-T. : Method of retarding and ameliorating central nervous system and eye damage, USPAT 5,527,533, 1996, June 18.
4) Yemelyanov, A.Y., Katz, N.B., Bernstein, P.S. : Ligand-binding characterization of xanthophyll carotenoids to solubilized membrane proteins derived from human retina, Exp. Eye Res., 2001, 72, 381-392.
5)Ohgami, K., Shiratori, K., Kotake, S., Nishida, T., Mizuki, N., Yazawa, K., Ohno, S. : Effects of
astaxanthin on lipopolysaccharide-induced inflammation in vitro and in vivo, Invest. Ophthalmol. Vis. Sci., 2003, 44, 2694-2701.

免疫・アレルギー
1) Tomita, Y., Jyonouchi, H., Engelman, R.W., Day, N.K., Good, R.A. : Preventive action of carotenoids on the development of lymphadenopathy and proteinuria in MRL-lpr/lpr mice, Autoimmunity, 1993, 16, 95-102.
2) Jyonouchi, H., Zhang, L., Tomita, Y. : Studies of immunomodulating actions of carotenoids. II. Astaxanthin enhances in vitro antibody production to T-dependent antigens without facilitating polyclonal B-cell, Nutr. Cancer, 1993, 19, 269-280.
3) Jyonouchi, H., Zhang, L., Gross, M., Tomita, Y. : Immunomodulating actions of carotenoids: enhancement of in vivo and in vitro antibody production to T-dependent antigens, Nutr. Cancer, 1994, 21, 47-58.
4) Jyonouchi, H., Sun, S., Tomota, Y., Gross, M. : Astaxanthin, a carotenoid without vitamin A activity,
augments antibody responses in culture including T-helper cell clones and suboptimal doses of antigen, J. Nutr., 1995, 125, 2483-2492.
5) Jyonouchi, H., Sun, S., 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, 1995, 23, 171-183.
6) Jyonouchi, H., Sun, S., Mizokami, M., Gross, M.D. : Effect of various carotenoids on cloned, effector-stage T-helper cell activity, Nutr. Cancer, 1996, 26, 313-324.
7) Bennedsen, M., Wang, X., Willen, R., Wadstroem, T., Andersen, L.P. : Treatment of H. pylori infected mice with antioxidant astaxanthin reduces gastric inflammation, bacterial load and modulated cytokine release by splenocytes, Immun. Letters, 1999, 70, 185-189.
8) Mahmoud, F.F., Haines, D.D., Abul, H.T., Abal, A.T., Onadeko, B.O., Wise, J.A. : In vitro effects of
astaxanthin combined with ginkgolide B on T lymphocyte activation in peripheral blood mononuclear cells from asthmatic subjects, J Pharmacol Sci., 2004, 94, 129-136.

がんに関連する作用
1)Tanaka, T., Morishita, Y., Suzuk, M., Kojima, T., Okumura, A., Mori, H. : Chemoprevention of mouse
urinary bladder carcinogenesis by the naturally occurring carotenoid astaxanthin, Carcinogenesis, 1994,
15, 15-19.
2) Tanaka, T., Makita, H., Ohnishi, M., Mori, H., Satoh, K., Hara, A. : Chemoprevention of rat oral
carcino-genesis by naturally occurring xanthophylls, astaxanthin and canthaxanthin, Cancer Res., 1995,
55, 4059-4064.
3) Tanaka, T., Kawamori, T., Ohnishi, M., Makita, H., Mori, H. Satoh, K., Hara, A. : Suppression of
azoxymethane-induced rat colon carcinogenesis by dietary administration of naturally occurring
xanthophylls astaxanthin and canthaxanthin during the postinitiation phase, Carcinogenesis, 1995, 16,
2957-2963.
4) Gradelet, S., Le Bon, A.M., Berg, R., Suschetet, M., Astorg, P. : Dietary carotenoids inhibit aflatoxin
B1-induced liver preneoplastic foci and DNA damage in the rat: role of the modulation of aflatoxin B1
metabolism, Carcinogenesis, 1998, 19, 403-411.
5) Nishino, H. : Cancer prevention by carotenoids, Mutat Res., 1998, 402, 159-163.
6) Chew, B.P., Park, J.S., Wong, M.W., Wong, T.S. : A comparison of the anticancer activities of dietary
β-carotene, canthaxanthin and astaxanthin in mice in vivo, Anticancer Res., 1999, 19, 1849-1853.
7) Jyonouchi, H., Sun,S. Iijima,K., Gross,M.D. : Antitumor activity of astaxanthin and its mode of action,
Nutr. Cancer, 2000, 36, 59-65.
8) Li, Z., Wang, Y., Mo, B. : The effects of carotenoides on the proliferation of human breastcancer cell
andgene expression of bcl-2, Zhonghua Yu Fang Yi Xue Za Zhi, 2002, 36, 254-257.

血圧、脂質、動脈硬化
1) Murillo, E. : Hypercholesterolemic effect of canthaxanthin and astaxanthin in rats, Arch. Latinoam Nutr., 1992, 42, 409-413.
2) Li, W., Hellsten, A., Jacobsson, L.S., Blomqvist, H.M., Olsson, A.G., Yuan, X.M. : Alpha-tocopherol and
astaxanthin decrease macrophage infiltration, apoptosis and vulnerability in atheroma of hyperlipidaemic rabbits, J. Mol. Cell Cardiol., 2004, 37, 969-978.
3) Gross, G.J., Lockwood, S.F. : Cardioprotection and myocardial salvage by a disodium disuccinate
astaxanthin derivative (Cardax), Life Sci., 2004, 75, 215-224.
4)Hussein, G., Nakamura, M., Zhao, Q., Iguchi, T., Goto, H., Sankawa, U., Watanabe, H. :
Antihypertensive and neuroprotective effects of astaxanthin in experimental animals, Biol. Pharm. Bull., 2005, 28, 47-52.

抗炎症
1) Kurashige, M., Okimura, E., Inoue, M., Utsumi, K. : Inhibition of oxidative injury of biological membranes by astaxanthin, Physiol. Chem. Phys., 1990, 22, 27-38.
2) Lingnell, A., Inborr, J. : Method of the prophylactic treatment of mastitis, WO 99/30701, 1999, June, 24.
3) Ohgami, K., Shiratori, K., Kotake, S., Nishida, T., Mizuki, N., Yazawa, K., Ohno, S.: Effects of astaxanthin
on lipopolysaccharide-induced inflammation in vitro and in vivo, Invest. Ophthalmol. Vis. Sci., 2003, 44,
2694-2701.
4) Lee, S.J., Bai, S.K., Lee, K.S., Namkoong, S., Na, H.J., Ha, K.S., Han, J.A., Yim, S.V., Chang, K., Kwon,
Y.G., Lee, S.K., Kim, Y.M. : Astaxanthin inhibits nitric oxide production and inflammatory gene expression by suppressing I(kappa)B kinase-dependent NF-kappaB activation, Mol. Cells, 2003, 16, 97-105.

抗ピロリ
1) Wang, X., Willen, R. and Wadstrom, T. : Astaxanthin-rich algal meal and vitamin C inhibit Helicobactor pylori infection in BALB/cA mice, Antimicrob. Agents Chemother., 2000, 44, 2452-2457.
2)Sjunnesson, H., Sturegard, E., Willen, R., Wadstrom, T. : High intake of selenium, beta-carotene, and
vitamins A, C, and E reduces growth of Helicobacter pylori in the guinea pig, Comp. Med., 2001, 51,
418-423.
3) Bennedsen, M., Wang, X., Willen, R., Wadstroem, T., Andersen, L.P. : Treatment of H. pylori infected
mice with antioxidant astaxanthin reduces gastric inflammation, bacterial load and modulated cytokine
release by splenocytes, Immun. Letters, 1999, 70, 185-189.

糖尿
1) ギュエン ヴァン チュエン, 藍物 南美, 新井 花恵, 山下 栄次:アスタキサンチン含有飲食物, 特許出願公開番号 特開平10-276721, 公開日1998年10月20日.
2) Uchiyama, K., Naito, Y., Hasegawa, G., Nakamura, N., Takahashi, J., Yoshikawa, T. : Astaxanthin
protects beta-cells against glucose toxicity in diabetic db/db mice, Redox. Rep., 2002, 7, 290-293.
3)Naito, Y., Uchiyama, K., Aoi, W., Hasegawa, G., Nakamura, N., Yoshida, N., Maoka, T., Takahashi, J.,
Yoshikawa, T. : Prevention of diabetic nephropathy by treatment with astaxanthin in diabetic db/db mice, Biofactors, 2004, 20, 49-59.

皮膚
1) 山下栄次:オキアミ由来スタキサンチンの色素沈着抑制効果, Fregnance J., 1995, 14, 180-185
2) Savoure, N., Briand, G., Amory-Touz, M.C., Combre, A., Maudet, M., Nicol, M. : Vitamin A status and
metabolism of cutaneous polyamines in the hairless mouse after UV irradiation: Action of β-carotene and astaxanthin, Int. J. Vitam. Nutr. Res., 1995, 65, 79-86.
3) Bohm, F., Edge, R., Lange, L., Truscott, T.G. : Enhanced protection of human cells against UV light by
antioxidant combinations involving dietary carotenoids, J. Photochem. Photobiol. B, 1998, 44, 211-215.
4) O' Connor, I., O'Brien, N. : Modulation of UVA light-induced oxidative stress by β-carotene, lutein and astaxanthin in culutured fibroblasts, J. Dermatol. Sci., 1998, 16, 226-230.
5)Lyons, N., O'Brien, N. : Modulatory effects of an algal extract containing astaxanthin on UVA-irradiated cells in culture, J. Dermatol. Sci., 2002, 30, 73.

運動系
1) 浅見純生:抗ストレス組成物、特許出願公開番号 特開平9-124470、公開日1997年5月13日.
2) Lignell, A. : Medicament for improvement of duration of muscle function or treatment of muscle disorders or diseases, WO 99/11251, 1998 , September, 4.
3) Aoi, W., Naito, Y., Sakuma, K., Kuchide, M., Tokuda, H., Maoka, T., Toyokuni, S., Oka, S., Yasuhara, M.,
Yoshikawa, T. : Astaxanthin limits exercise-induced skeletal and cardiac muscle damage in mice, Antioxid Redox Signal., 2003, 5, 139-144.

-臨床-
視覚系

1) Seddon, J.M., Ajani, U.A., Sperduto, R.D., Hiller, R., Blair, N., Burton, T.C., Farber, M.D., Gragoudas, E.S.,
Haller, J., Miller, D.T.: Dietary carotenoids, vitamins A, C, and E, and advanced age-related macular
degeneration, J. Am. Med. Assoc., 1994, 272, 1413-1420.
2) Snodderly, D.M.: Evidence for protection against age-related macular degeneration by carotenoids and antioxidant vitamins, Am. J. Clin. Nutr., 1995, 62, s1448-s1461.
3) Lyle, B.J., Mares-Perlman, J.A., Klein, B.E.K., Klein, R., Palta, M., Bowen, P.E., Greger, J.L. : Serum
carotenoids and tocopherols and incidence of age-related nuclear cataract, Am. J. Clin. Nutr., 1999, 69,
272-277.
4) Dagnelie, G., Zorge, I.S., McDonald, T.M. : Lutein improves visual function in some patients with retinal degeneration: a pilot study via the internet, Optometry, 2000, 71, 47-164.
5) 澤木啓祐、吉儀宏、青木和浩、鯉川なつえ、東根明人、金子今朝秋、山口正弘 : アスタキサンチンのスポーツパフォーマンスに及ぼす影響−運動選手の視機能と筋肉疲労回復に対する効果について−, 臨床医薬, 2002, 18, 1085-1099.
6) Nagaki, Y., Hayasaka, S., Yamada, T., Hayasaka, Y., Sanada, M., Uonomi, T.: Effects of astaxanthin on
accommodation, critical flicker fudion, and pattern visual evoked potential in visual display terminal
workers, J. Trad. Med., 2002, 19, 170-173.
7) 中村彰、磯部綾子、大高康博、あべ松泰子、中田大介、本間知佳、櫻井禅、島田佳明、堀口正之: アスタキサンチンによる視機能の変化, 臨床眼科, 2004, 58, 1051-1054.
8) 新田卓也、大神一浩、白取謙治、新明康弘、陳 進輝、吉田和彦、塚原寛樹、大野重昭 : アスタキサンチンの調節機能および疲れ眼に及ぼす影響− 健常成人を対象とした摂取量設定試験 −, 臨床医薬, 2005,
9)白取謙治、大神一浩、新田卓也、新明康弘、陳 進輝、吉田和彦、塚原寛樹、竹原功 、大野重昭 : アスタキサンチンの調節機能および疲れ眼に及ぼす影響− 健常成人を対象とした効果確認試験 −, 臨床医薬, 2005,

皮膚
1) 山下栄次 : オキアミ由来スタキサンチンの色素沈着抑制効果, Fregnance J., 1995, 14, 180-185.
2) Stahl, W., Heinrich, U., Jungmann, H., Sies, H., Tronnier, H. : Carotenoids and carotenoids plus vitamin E protect against ultraviolet light?induced erythema in humans, Am. J. Clin. Nutr., 2000, 71, 795-798.
3) Lee, J., Jiang, S., Levine, N., Watoson, R.R. : Carotenoid supplemantation reduces erythema in human
skin after simulated solar radiation exposure, Proc. Soc. Exp. Biol. Med., 2000, 223, 170-174.
4) Seki, T., Sueki, H., Kouno, H., Suganuma, K., Yamashita, E. : Effects of astaxanthin from Haematococcus pluvialis on human skin, Fragrance J., 2001, 29, 98-103.

運動系
1)Sawaki, K., Yoshigi, H., Aoki, K., Koikawwa, N., Azumane, A., Kaneko, K., Yamaguchi, M. : Sports
performance benefits from taking natural astaxanthin charaacterized by visual activity and muscle fatigue improvement in humans, J. Clin. Thrap. Med., 2002, 18, 1085-1099.
2)永田晟, 田島多恵子, 浜松ほづみ : アスタキサンチン投与による三段階運動負荷の疲労回復効果, 疲労と休養の科学, 2003, 18, 35-45.

その他の試験
1) 宮脇寛海、高橋二郎、塚原寛樹、竹原功 : アスタキサンチンの血液流動性に与える影響, 臨床医薬, 2005,
2) 長木泰典、三原美春、高橋二郎、北村晃利、堀田良晴、杉浦友梨、湊貞正 : アスタキサンチンの網膜血管血流量に及ぼす影響, 臨床医薬, 2005,

アスタキサンチンの代謝

関連文献・研究 (アスタキサンチンの代謝)

動態
1)Osterlie, M, Bjerkeng, B, Liaaen-Jensen, S. : Plasma appearance and distribution of astaxanthin E/Z
and R/S isomers in plasma lipoproteins of men after single dose administration of astaxanthin., J. Nutr. Biochem., 2000, 11, 482-490.
2)Showalter, L.A., Weinman, S.A., OSterlie, M., Lockwood, S.F. : Plasma appearance and tissue
accumulation of non-esterified, free astaxanthin in C57BL/6 mice after oral dosing of a disodium
disuccinate diester of astaxanthin (Heptax trade mark ), Comp. Biochem. Physiol. C Toxicol. Pharmacol., 2004, 137, 227-36.
3) Coral-Hinostroza, G.N., Ytrestoyl, T., Ruyter, B., Bjerkeng, B. : Plasma appearance of unesterified
astaxanthin geometrical E/Z and optical R/S isomers in men given single doses of a mixture of optical 3 and 3'R/S isomers of astaxanthin fatty acyl diesters, Comp. Biochem. Physiol. C Toxicol. Pharmacol., 2004, 139, 99-110.

吸収
1)安藤清一 : 魚類における体内移行,海洋生物のカロテノイド−代謝と生物活性,日本水産学会監修,幹渉編,水産学シリーズ 94,1993, p49−p58, 恒星社厚生閣, 東京.
2)Clark, R.M., Furr, H.C. : Absorption of canthaxanthin by the rat is influenced by total lipid in the
intestinal lumen, Lipids, 2001, 36, 473-475.
3)Mercke Odeberg, J., Lignell, A., Pettersson, A., Hoglund, P. : Oral bioavailability of the antioxidant
astaxanthin in humans is enhanced by incorporation of lipid based formulations, Eur J Pharm Sci., 2003, 19, 299-304.

魚類
1)Katsuyama, M, Komori, T, Matsuno, T. : Metabolism of three stereoisomers of astaxanthin in the fish,
rainbow trout and tilapia., Comp. Biochem. Physiol. B, 1987, 86, 1-5.
2) Aas, G.H., Bjerkeng, B., Storebakken, T., Ruyter, B. : Blood appearance, metabolic transformation and
plasma transport proteins of 14C-astaxanthin in Atlantic salmon (Salmon salar L.), Fish Physiol.
Biochem., 1999, 21, 325-334
3) Osterlie, M., Bjerkeng, B., Liaaen-Jensen, S. : Accumulation of astaxanthin all-E, 9Z and 13Z geometrical
isomers and 3 and 3' RS optical isomers in rainbow trout (Oncorhynchus mykiss) is selective, J. Nutr.,
1999, 129, 391-398.
4) Xu, Y., Ding, Z. : Traced studies on metabolism of astaxanthin in Atlantic salmon (salmo salar), J. Exp.Zool., 2004, 301A, 317-323.

動物 
1)Ershov, IuV., Dmitrovskii, A.A., Bykhovskii, VIa. : The character of the interaction of beta-carotene-15,15'-dioxygenase from rabbit small intestine with lycopene, 15,15'-dehydro-beta-carotene, lutein, and astaxanthine, Biokhimiia, 1993, 58, 733-739.
2) Astorg, P., Gradelet, S., Leclerc, J., Siess, M.H. : Effects of provitamin A or non-provitamin A carotenoids -on liver xenobiotic-metabolizing enzymes in mice. Nutr Cancer, 1997, 27, 245-249.
3) Wolz, E., Liechti, H., Notter, B., Oesterhelt, G., Kistler, A. : Characterization of metabolites of astaxanthin in primary cultures of rat hepatocytes, Drug Metab. Dispos., 1999 27, 456-462.
4)Kistler, A., Liechti, H., Pichard, L., Wolz, E., Oesterhelt, G., Hayes, A., Maurel, P. : Metabolism and
CYP-inducer properties of astaxanthin in man and primary human hepatocytes, Arch. Toxicol., 2002, 75, 665-675.

ヒト 
1) Osterlie, M, Bjerkeng, B, Liaaen-Jensen, S. : Plasma appearance and distribution of astaxanthin E/Z and R/S isomers in plasma lipoproteins of men after single dose administration of astaxanthin., J. Nutr. Biochem., 2000, 11, 482-490.
2)Kistler, A., Liechti, H., Pichard, L., Wolz, E., Oesterhelt, G., Hayes, A., Maurel, P. : Metabolism and
CYP-inducer properties of astaxanthin in man and primary human hepatocytes, Arch. Toxicol., 2002, 75, 665-675.

体内分布
1)Takahashi, K., Watanabe, M., Takimoto, T., Akiba, Y. : Uptake and distribution of astaxanthin in several tissues and plasma lipoproteins in male broiler chickens fed a yeast (Phaffia rhodozyma) with a high
concentration of astaxanthin, Br. Poult. Sci., 2004, 45, 133-138.
2)Coral-Hinostroza, G.N., Ytrestoyl, T., Ruyter, B., Bjerkeng, B. : Plasma appearance of unesterified
astaxanthin geometrical E/Z and optical R/S isomers in men given single doses of a mixture of optical 3 and 3'R/S isomers of astaxanthin fatty acyl diesters, Comp. Biochem. Physiol. C Toxicol. Pharmacol., 2004, 139, 99-110.

安全性


関連文献・研究 (安全性)

変異原性
1)高橋二郎、塚原寛樹、湊貞正 : ヘマトコッカス藻アスタキサンチンの毒性試験−Ames試験、ラット単回投与毒性試験、ラット90日反復経口投与亜慢性毒性試験―, 臨床医薬, 2004, 20, 876-881.

急性毒性
1)高橋二郎、塚原寛樹、湊貞正 : ヘマトコッカス藻アスタキサンチンの毒性試験−Ames試験、ラット単回投与毒性試験、ラット90日反復経口投与亜慢性毒性試験―, 臨床医薬, 2004, 20, 876-881.

亜慢性毒性
1) 西川善之, 峰中美治, 一村美香 : 実験動物に対するカロテノイド類(β-カロテン, アスタキサンチン)供与の生理・生化学的効果について, 甲子園大学紀要、栄養学部編, 1997, 25, 19-25.
2) 小野敦、関田清司、斉藤実、梅村隆志、小川幸男、降矢強、金子豊蔵、井上達 : ヘマトコッカス藻色素のF334ラットによる13週間反復混餌投与毒性試験, 国立医薬品食品衛生研究所報告, 1999, 117, 91-98.
3)高橋二郎、塚原寛樹、湊貞正 : ヘマトコッカス藻アスタキサンチンの毒性試験−Ames試験、ラット単回投与毒性試験、ラット90日反復経口投与亜慢性毒性試験―, 臨床医薬, 2004, 20, 876-881.

ヒトにおける安全性
1) 15消安第1321号に係る食品健康影響評価の結果の通知について : 食品安全委員会 委員長 寺田雅昭, 府食第281号の1 平成16年3月11日.
2) Seki,T., Sueki,H., Kouno,H., Suganuma,K., Yamashita,E.:Effects of astaxanthin from Haematococcus
pluvialis on human skin, Fragrance J., 2001, 29, 98-103.
3) Spiller,G.A., Dewell,A.: Safety of an Astaxanthin-Rich Haematococcus pluvialis Algal Extract : A
Randomized Clinical Trial, J. Med. Food, 2003, 6, 51-56.
4) 塚原寛樹、福原育夫、竹原功 : アスタキサンチン含有ソフトカプセル食品の健常成人に対する長期摂取における安全性の検討, 臨床医薬, 2005, 20, -.
5) 大神一浩、白取謙治、新田卓也、新明康弘、陳 進輝、吉田和彦、塚原寛樹、大野重昭: アスタキサンチンの過剰摂取による安全性の検討, 臨床医薬, 2005, 20, -.
6) 澤木啓祐、吉儀宏、青木和浩、鯉川なつえ、東根明人、金子今朝秋、山口正弘 : アスタキサンチのスポーツパフォーマンスに及ぼす影響−運動選手の視機能と筋肉疲労回復に対する効果について−, 臨床医薬, 2002, 18, 1085-1099.
7)中村彰、磯部綾子、大高康博、あべ松泰子、中田大介、本間知佳、櫻井禅、島田佳明、堀口正之 : アスタキサンチンによる視機能の変化, 臨床眼科, 2004, 58, 1051-1054.

古書などに見られる食経験
1)ヘマトコッカス藻色素(ヘマトコッカスの全藻から得られた、アスタキサンチンを主成分とするもの。):日本食品添加物協会技術委員会, 既存添加物名簿収載品目リスト注解書, 既存添加物名簿番号(403),平成11年,日本添加物協会.
2) サケ・マス : 食品大百科事典, (独)食品総合研究所編, p93-p94,(2001), 朝倉書店,東京.
3) 市川健夫 : 遺跡・資料にみられるサケ漁, 日本本土におけるサケ漁業史、NHKブックス294,日本のサケ その文化誌と漁,p70-p72,(昭和52年), 日本放送出版協会.
4) 小幡弥太郎 : 古代日本人の食物 サケとマス,日本人のたべもの,p143-147,(1961), 河出書房新社,東京.
5) 矢野研一 : 初穂と初尾,魚の文化史、p22-p23,(1983),講談社,東京.


安全性
色揚げ剤

1)森徹 : 養殖魚の体色改善、水産学シリーズ 94 海洋生物のカロテノイド−代謝と生物活性、幹渉編、日本水産学会監修、p59-p68、1993、恒星社厚生閣、東京.
2) Steven, D.M. : Studies on animal carotenoids, J. Exp. Biol., 1948, 25, 369-387.
3) Mori, T., Makabe, K., Yamaguchi, K., Konosu, S., Arai, S. : Comparison between krill astaxanthin diester and synthesized free astaxanthin suplemented to diets in their absorption and seposition by Juvenile Coho Salmon (Onchorynchus kisutch), 1989, 93B, 225-258.
4) Smith, B.E., Hardy, R.W., Torrissen, O.J. : Synthetic astaxanthin deposition in pan-size coho salmon
(Oncorhynchus kisutch), Aquaculture, 1992, 104, 105-119.
5) Fujita, T., Satake, M., Watanabe, T., Kitajima, C., Miki, W., Yamaguchi, K., Konosu, S. : Pigmentation of
cultured red sea breeam with sataxanthin diseter purified from krill oil, Bull. Jap. Sos. Sci. Fish., 1983, 49, 1855-1861.
6) 与賀田稔久 : マダイの養殖と体色調製, 長崎水試登録, 1968, 287, 1-17.
7) Johnson, E.A., Conklin, D.E., Lewis, M.J. : The yeast Phaffia rodozyma as a dietary pigment source for salmonids and crustaceans, J. Fish Res. Boad. Can.,1977, 34, 2427-2421.
8) Johnson, E.A. : Phaffia rhodozyma: colorful odyssey, Int. Microbiol. 2003, 6, 169-174.

ニワトリ
1)Lignell, A., Nicolin, C., Larsson, L.-K., Inborr, J. : Agent for increasing the production of/in breeding and production animals in the poultry industry, WO, 9608977A1, 1996, March, 28.
2) Ingorr, J., Waldenstedt, L. : Effect of astaxanthin-rich algal meal(H. pluvialis) on growth performance,
caecal Campylobacter and Clostridium counts and tissue astaxanthin concentration of broiler chickens, Proc. Aust. Poult. Sci. Sym., 2000. 12, 174-177.
3) Inborr, J., Lignell, A. : Effect of feeding astaxanthin-rich alge meal(Haematococcus pluvialis) on
perfor-mance and carotenoid concentration of different tissues of broiler chickens, Proc. 8th European
Symp. On the Quality of Poultry Meat, Poznan, Poland, 1997, Session M1, 39-43.
4)Elwinger, K., Inborr, J. : Composition and taste of eggs enriched with omega-3 fatty acids and natural
astaxanthin, Proc. 8th Europian Symp. On the Quality of Eggs and Egg Products, Bologna, Italy, 1999.
5) 秋葉征夫, 佐藤幹, 高橋和昭, 豊水正昭, 高橋洋子, 小梨茂, 恒川博, 早坂豊, 長尾秀則:Improved
Pigmentation of Egg Yolk by Feeding of Yeast Phaffia rhodozyma Containing High Concentration of
Astaxanthin in Laying Hens., J. Poult. Sci., 2000, 37, 162-170.


1) Lingnell, A., Inborr, J., Nicolin, C. : Method of increasing the production and improving the quality of
semen, WO, 99/29313, 1999, June, 17.
2)Lingnell, A., Inborr, J. : Agent for increasing the production of/in breeding and production mammals,
USPAT, 6,054,491, 2000, April, 25.


1) Lingnell, A., Inborr, J. : Method of the prophylactic treatment of mastitis, WO 99/30701, 1999,June, 24.

ミンク
1)Hansen, K.B., Tauson, A.H., Inborr, J. : Effect of supplementation with the antioxidant astaxanthin on
reproduction, preweaning growth performance of kits and daily milk intake in mink, J. Reprod. Fertil.
Suppl., 2001, 57, 331-334.


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