Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing compound containing a carotene nucleus
Reexamination Certificate
2001-02-26
2004-08-31
Tate, Christopher R. (Department: 1654)
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing compound containing a carotene nucleus
C424S093100
Reexamination Certificate
active
06783951
ABSTRACT:
BACKGROUND OF THE INVENTION
Carotenoids are a class of biochemicals consisting of the carotenes. Xanthophylls are a related class of biochemicals and are the oxygenated derivatives of carotenoids. The prefix “apo” with an associated number or locant, signifies that all of the carotene molecule beyond that indicated part has been replaced by hydrogen atoms. Because these molecules contain a long series of conjugated double bonds, they often are highly colored, most often with red-to-yellow pigmentation. The most familiar carotenoid is &bgr;-carotene, which is commonly found in carrots, in sweet potatoes and other yellow vegetables, and in green, leafy vegetables such as spinach and kale. The carotenoids, xanthophylls and apo-carotenoids have value as both colorants and nutritional dietary supplements.
&bgr;-carotene is used as a food additive both as a colorant and a dietary supplement (Bauerfeind, J. C., et al. (1971) “Use of carotenoids.” In:
Carotenoids
. O. Isler et al. (eds.), Halsted Press, New York, pp.743-770.). In these applications, the usual chemical form of &bgr;carotene is the all-trans configuration, which is the isomer found in root vegetables and in the synthetic material produced by the principal manufacturing technologies.
&bgr;-carotene has been indicated to play a role in the prevention of cancer (Hennekens, et al., (1986)
Cancer
58: 1837-1841; Krinsky, N. I. (1971) “Function.” In:
Carotenoids
, O. Isler et al. (eds.), Halsted Press, New York, pp. 669-716.; Krinsky, N. I. (1988)
Clin. Nutr.
7: 107-112; Mathews-Roth, M. M., and Krinsky, N. I. (1987)
Photochem. and Photobiol.
40(4): 507-509; Krinsky et al., (1982)
J. Natl. Cancer Institute
69: 205-210; Menkes, M., et al. (1986)
New England J. of Med.
315: 1250-1254). Carotenoids such as &bgr;-carotene, and xanthophylls such astaxanthin, have also been shown to play central roles in the metabolism of the eye's macula and retina and in maintaining healthy vision (Handelman, G. J., and Dratz, E. A. (1986) “The role of antioxidants in the retina and retinal pigment epithelium and the nature of prooxidant-induced damage.”
Adv. in Free Radical Biology and Medicine,
Vol. 2, pp. 1-89). Most Americans do not receive what is regarded by some as an optimal minimum dosage of approximately 75,000 I. U. (International Units) per day (Taylor, R. F., and Little. A. D. (1990) “Carotenoids: products, applications, and markets.”
SPECTRUM Food Industry, pp.
1-11).
The xanthophyll pigment astaxanthin is widely distributed in nature and is the predominant pigment in shrimp, crab, lobster, and salmonids. Additionally, it produces the red coloration of some birds such as flamingos and the scarlet ibis (Weedon, B. C. L. (1971) “Occurrence.” In:
Carotenoids,
O. Isler et al. (eds.), Halsted Press, New York, pp. 29-60.). There is evidence that xanthophylls function as chemo-protectives. In addition, other xanthophylls, such as adonirubin and astaxanthin, may also act as nutraceuticals that prevent carcinogenesis through anti-oxidative, anti-free radical, or other mechanisms. The beneficial nutraceutical functions of the carotenes and xanthophylls extend to the prevention of heart attacks and strokes).
One of the most important uses of the xanthophylls is in animal feed. Astaxanthin provides the distinctive coloration for many multicellular organisms and generally must be obtained from a dietary source. When fish such as salmon, rainbow trout, red sea bream, or yellowtail are aquacultured, this pigment must be included as a dietary supplement in order to produce the coloration necessary for effective marketing (Committee on Animal Nutrition, National Research Council (1983)
Nutrient Requirements of Warmwater Fishes and Shellfishes.
National Academy of Science, pp. 55-57; Foss, P., et al., (1984)
Aquaculture
41: 213-226; Foss, P., et al., (1987)
Aquaculture
65: 293-305; Meyers, S. P., and Chen., H-M. (1982) “Astaxanthin and its role in fish culture,” In:
Proceedings of the Warmwater Fish Culture Workshop,
Special Publication No. 3, World Mariculture Society, Charleston, S.C.; Torrissen, O. J. (1986)
Aquaculture
53: 271-278; Torrissen., O. J., et al., (1987) “Pigmentation of salmonids-carotenoid deposition and metabolism.” Northwest and Alaska Fisheries Center). Pigmentation has been achieved using arctic krill as a dietary supplement (Arai, S., et al., (1987)
Aquaculture
66: 255-264), but this is expensive.
Canthaxanthin is also used as a food colorant, principally in pink grapefruit juice cocktail mixtures and in poultry, eggs, and aquacultured fish, where it is introduced through the feeds. There are no industrial microbial processes for the production of canthaxanthin, although it is found in the fungus that provides its name,
Cantharellus cinnabarinns.
A recent study estimates that twenty percent of the carotene and xanthophyll supplement markets are dedicated to the natural form as opposed to synthetic materials (Taylor, R. F., and Little. A. D. (1990) “Carotenoids: products, applications, and markets.”
SPECTRUM Food Industry,
pp. 1-11). The principal source of natural microbial &bgr;carotene has been photoautotrophic microalgae
Dunaliella salinas
and
Dunaliella bardawil
(Ben-Amotz ET AL., (1990)
Tibtech
76(5): 121-126; Ben-Amotz, A. (1986). “&bgr;-carotene enhancement and its role in protecting
Dunaliella bardawil
against injury by high irradiance.” In:
Algal Biomass Technologies,
W. R. Barclay and R. P. McIntosh (eds.), J. Cramer, Berlin, pp. 132-147). Approximately one-third of the natural &bgr;-carotene produced by Dunaliella is the 9-cis isomer. The differentiation between the 9-cis and all-trans form of &bgr;-carotene has been claimed to be nutritionally important (Ben-Amotz et al., (1989)
J. Nutrition
119: 1013-1019). A commercial obstacle to using Dunaliella as a source for &bgr;-carotene is the difficulty of extracting the pigments from the organisms. This difficulty in extraction correlates with a difficulty in bioexpression of the pigments (defined as the amount of pigment absorbed as a percentage of the amount consumed) when the Dunaliella organism is fed to an animal as a pigment source (Nonomura (1987) U.S. Pat. No. 4,680,314).
A recent comprehensive review (Johnson, E. A., and An, G-W. (1991)
Critical Reviews in Biotechnology
11(4): 297-326) cites only two microbial species that are producers of astaxanthin. One is the green microalga Haematococcus, and the other is the yeast
Phaffia rhodozyma.
Production using Haematococcus has been attempted in photo-autotrophic cultivation in open, fresh-water ponds. Unlike Dunaliella, Haematococcus cannot grow in highly-saline culture conditions, and the fresh-water ponds contaminate easily. Otherwise, production is in closed systems and is very costly.
Astaxanthin is also produced in the Phaffia yeast (An, et al., (1990)
Applied and Environmental Microbiology,
55: 116-124; An, et al.(1991)
Bio/Technology
9: 70-73). One difficulty that has limited the appeal of both Haematococcus and Phaffia as sources of astaxanthin is very low bioavailability and bioexpression of the astaxanthin in the intact organism, which is attributed to the strong cell walls.
The Thraustochytriales are a relatively obscure order of unicellular organisms rarely described in biology textbooks (Bahnweg, G., and Jackle, I. (1986) “A new approach to taxonomy of the Thraustochytriales and Lybrinthulales.” In:
The Biology of Marine Fungi,
S. T. Moss (ed.), Cambridge University Press, London, pp. 131-140). Thraustochytriales are saprobs, feeding on plant detritus, and are common in marine and estuarine waters, growing naturally at a variety of salinities. Thraustochytriales are known to occur on marine macroalgae as well, and they are found in environments stretching from tropical waters to arctic and Antarctic environments. Reproduction is vegetative or involves the formation of zoospores, which escape through a variety of cleavage mechanisms to produce new sporangia.
Thraustochytriales are described as “eucarpic and monocentric, with an endobiotic rhizoi
Ali Janann Y.
Farrell Kevin M.
Pierce Atwood
Tate Christopher R.
Winston Randall
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