Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Peptide containing doai
Reexamination Certificate
2000-08-28
2002-10-15
Carlson, Karen Cochrane (Department: 1653)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Peptide containing doai
C514S012200, C514S015800, C514S017400, C514S018700, C424S439000, C435S068100, C426S034000, C530S305000, C530S329000
Reexamination Certificate
active
06465432
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to antioxidant peptides and methods for isolating antioxidative peptides. More specifically, the present invention relates to antioxidant peptides derived from casein. These antioxidant peptides may be used as food supplements or food additives.
BACKGROUND
Oxidation of oils and fats in foods causes deterioration of flavor and degradation of oil/fat quality. Furthermore, the intake of peroxides produced form lipid oxidation exerts detrimental effects in vivo. Free radicals and active oxygen species generated in the course of oxidation reactions denature proteins in vivo, inactivate enzymes (Szweda et al., “Inactivation of glucose-6-phosphate dehydrogenase, by 4-hydroxy-2-nonene modification of an active-site lysine,”
J. Biol. Chem
. 268:3342 (1993)), bring about mutations in DNA (Reiss et al., “DNA-malonaldehyde reaction: Formation of fluorescent products,”
Biochem. Biophys. Res. Commun
. 48:921 (1972)), modify low density lipoproteins (Alaiz et al., “Modification of delipidated apoprotein B of low density lipoprotein by lipid oxidation products in relation to macrophage scavenger receptor binding,”
Biol. Phar. Bull
. 17:51 (1994)), and contribute to aging and various diseases such as cancer. Dietary antioxidants may help prevent cardiovascular diseases (Krinksy, N. I., “Action of carotenoids in biological systems,”
Annu. Rev. Nutri
. 13:561 (1993); Parthasarathy, S., “Mechanisms by which dietary antioxidants may prevent cardioscular diseases,”
J. Med. Food
1:45 (1998)).
Many substances have been identified which have antioxidative activity. These include glutathione, carnosine (Zhou et al., “Ability of carnosine and other skeletal muscle components to quench unsaturated aldehydic lipid oxidation products,”
J. Agric. Food Chem
. 47:51(1999)), certain amino acids (Marcuse et al.,
Nature
, (1960)), certain proteins, including lactoferrin (Gutteridge et al.,
Bioch. J
. 199:259 (1981)), casein (Laakso, “Inhibition of lipid peroxidation by casein. Evidence of molecular encapsulation of 1,4-pentadiene fatty acids,”
Biochim. Biophys. Acta
792:11 (1984)), and certain peptides (Tomita et al., “Antioxidant,” U.S. Pat. No. 5,804,555 (1998), Suetsuna et al., “Isolation and characterization of free radical scavenging activities peptides derived from casein,”
J. Nurt. Biochem
. 11:128 (2000)). However, because of the importance in preventing oxidation to biological processes and to improved stability of products subject to oxidation, there remains a need to identify new antioxidative compounds, such as antioxidant peptides. Furthermore, there remains a need for a general method that can be used to isolate antioxidative peptides from virtually any protein source.
Miclo et al, U.S. Pat. No. 5,846,939, described a decapeptide from alpha s1 casein with benzodiazepine-type activity which is useful for the treatment of convulsions and anxiety. However, Miclo et al. did not analyze the decapeptide, or fragments thereof, for antioxidative activity.
Shimamura et al., U.S. Pat. No. 5,952,193, described a method for producing a peptide mixture from whey protein utilizing hydrolysis carried out by a protease. In some embodiments, the peptides generated by hydrolysis are further purified. However, Shimamura et al., did not disclose phase separation of the peptides nor determine antioxidative activities of the peptide mixture.
Tomita et al., U.S. Pat. No. 5,804,555, described an antioxidant hydrolysate of lactoferrin. After cleaving lactoferrin with protease, the resulting peptides were purified by reverse phase HPLC. Tomita et al. did not disclose a method for isolating antioxidative peptide fractions that utilizes a separation step that does not result in purified peptide fractions, or that is used in combination with, or in place of, reverse phase HPLC or size-based separation. Additionally, Tomita et al. did not disclose antioxidative peptides of casein, whey, or soy protein. Finally, Tomita et al. did not disclose a phase separation step in isolating antioxidative peptide fragments.
Suestsuna et al. (“Isolation and characterization of free radical scavenging activities peptides [sic] derived from casein,”
J. Nutr. Biochem
., 11:128 (2000)) described peptides with antioxidative activity generated from proteolytic cleavage of casein. Peptides with sequence EL, YFYPEL, FYPEL, YPEL, and PEL were provided. The peptides were purified using a method including several column chromatography-steps.
Thus, there remains a need for additional anti-oxidative peptides and for easier to use, and more cost effective, methods for isolating anti-oxidative peptides. Additionally, there remains a need for a general method of anti-oxidative peptide isolation that can be utilized to isolate peptides from many protein sources.
The current invention provides antioxidative peptides from casein. Furthermore, the current invention includes methods that can be used to isolate antioxidative peptide fractions or antioxidative peptides from any protein source.
SUMMARY OF THE INVENTION
The current invention provides antioxidative peptide fractions. The invention includes antioxidative peptides comprising sequences SEQ ID NOS:1-5. The invention includes methods for making the antioxidative peptides, isolated nucleic acids encoding the antioxidative peptides, and expression vectors comprising these nucleic acids. The invention includes food additives for preventing oxidation in vivo. The invention includes stabilized products with improved storage characteristics which are oxidation resistant. Finally, the invention includes methods for isolating peptide fractions having antioxidative activity from protein samples.
In one aspect, the present invention is an isolated peptide comprising an amino acid sequence selected from the group consisting of SEQ ID NO:1, SEQ ID NO:2, SEQ ID NO:3, SEQ ID NO:4, and SEQ ID NO:5, wherein the peptide has antioxidative activity. In one embodiment, the amino acid sequence is SEQ ID NO:1. In another embodiment, the amino acid sequence is SEQ ID NO:3. In another embodiment, the amino acid sequence is SEQ ID NO:4. In another embodiment, the amino acid sequence is SEQ ID NO:5.
In one aspect, the present invention is an isolated antioxidative casein peptide consisting essentially of an amino acid sequence selected from the group consisting of SEQ ID NO:1, SEQ ID NO:2, SEQ ID NO:3, SEQ ID NO:4, and SEQ ID NO:5. In one embodiment, the antioxidative peptide consists essentially of the amino acid sequence of SEQ ID NO:1. In another embodiment, the antioxidative peptide consists essentially of the amino acid sequence of SEQ ID NO:2. In another embodiment, the antioxidative peptide consists essentially of the amino acid sequence of SEQ ID NO:3. In another embodiment, the antioxidative peptide consists essentially of the amino acid sequence of SEQ ID NO:4. In another embodiment, the antioxidative peptide consists essentially of the amino acid sequence of SEQ ID NO:5.
In another embodiment, the isolated antioxidative casein peptide consists of an amino acid sequence selected from the group consisting of SEQ ID NO:1, SEQ ID NO:2, SEQ ID NO:3, SEQ ID NO:4, and SEQ ID NO:5. In one embodiment, the antioxidative peptide consists of the amino acid sequence of SEQ ID NO:1. In another embodiment, the antioxidative peptide consists of the amino acid sequence of SEQ ID NO:2. In another embodiment, the antioxidative peptide consists of the amino acid sequence of SEQ ID NO:3. In another embodiment, the antioxidative peptide consists of the amino acid sequence of SEQ ID NO:4. In another embodiment, the antioxidative peptide consists of the amino acid sequence of SEQ ID NO:5.
In another aspect, the current invention is a food supplement comprising: an antioxidative peptide comprising an amino acid sequence selected from the group consisting of SEQ ID NQ.1, SEQ IN DO:2, SEQ ID NO:3, SEQ ID NO:4, and SEQ ID NO:5, said antioxidative peptide being present in an amount effective for preventing in vivo oxidation; and an orally-ingestible diluent or carrier. In o
Gao Song
Han Xiao-Qing
Lincourt Richard H.
Parkin Kirk L.
Carlson Karen Cochrane
Fitch Even Tabin & Flannery
Kam Chih-Min
Kraft Food Holdings, Inc.
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