Drug – bio-affecting and body treating compositions – Plant material or plant extract of undetermined constitution... – Containing or obtained from a flower or blossom
Reexamination Certificate
2002-01-30
2004-02-10
Page, Thurman K. (Department: 1615)
Drug, bio-affecting and body treating compositions
Plant material or plant extract of undetermined constitution...
Containing or obtained from a flower or blossom
C424S439000, C424S489000, C424S400000, C210S660000, C210S669000, C210S732000
Reexamination Certificate
active
06689400
ABSTRACT:
BACKGROUND OF THE INVENTION
Lutein is a carotenoid found in fruits and vegetables which has begun to acquire importance as a nutraceutical because of its antioxidant and immunomodulating/immunostimulating actions. These actions are manifested in its ability to reduce oxidative stress and/or depression of the immune system, in conditions such as age-related macular degeneration, cataracts, atherosclerosis, and some forms of cancer. Also, because of its yellow to red coloration and natural occurrence in human foods, lutein also is used as a food colorant.
Lutein suitable for nutraceutical and cosmetic uses can be found in the chromoplasts of flowers, fruits and roots (such as, but not limited to, carrots and yellow potatoes). Lutein is typically present in plant chromoplasts as long chain fatty esters, typically diesters, of acids such as palmitic and myristic acids, e.g. lutein dipalminate, lutein dimyristate and lutein monomyristate. It has also been noted that once lutein is isolated from the plant, the lutein is biologically active in either the ester form or in the free form.
Additionally, the highly unsaturated unconjugated chain of caroteinoids that makes up lutein is very sensitive to air, oxidizing agents, reducing agents, and structural alterations. Therefore, the loss of lutein during storage is well known. Further, lutein loss has been shown to begun as early as the raw material handling stage of the process. It has been documented that under carefully controlled conditions exposure to white fluorescent light resulted in the degradation of lutein in the range of 0.8-10.7% per day (please see Nahrung, 44, 38-41). However, ascorbic acid, an alkaline pH, low temperature (4° C.) and darkness were found to retard the degradation of carotenoids, including lutein (please see Akad. Nauk. SSSR., 127, 1128-1131; Chem Abstr., 54, 11162). It has also been discovered that lutein and lutein esters are not stable compounds at room temperature or higher, and that free lutein is especially vulnerable to chemical and biological deterioration.
The preparation of stable and biologically active lutein and/or its esters from natural sources, such as Marigold petals, presents a challenging task. As seen in the following discussion, many patents have been issued on a method of obtaining such esters and the composition of the same.
U.S. Pat. No. 5,382,714 (hereinafter the “'714 patent”) discloses a method of isolating, purifying and recrystallizing substantially pure lutein, preferably from saponified marigold oleoresin in its pure free form, apart from chemical impurities and other carotenoids. It also discloses that as of the filing of the '714 patent, pure lutein suitable for human use had not been commercially available for use as a chemopreventative agent in clinical trials. It was also noted that pure lutein which is free of chemical contaminant is necessary to design and conduct proper human intervention studies.
The '714 patent noticed that esterified luteins are found with fatty acids in marigold petals, and that lutein could be produced upon saponification of the marigold lutein esters. However, the resulting lutein product was impure as it was contaminated with numerous chemical impurities.
The '714 patent disclosed a method of removing the lutein from the marigold petals without the chemical impurities. This method is disclosed as comprising the purification, preferably of a saponified marigold extract through the use of a series of filtrations and water/alcohol washes to obtain crude lutein crystals. These crystals are then dissolved in a halogenated organic solvent in which lutein is strongly soluble and then in a second organic solvent in which lutein is only partly soluble. This mixture is then cooled and the lutein is recrystallized in a high purity and it is then filtered and dried under vacuum.
U.S. Pat. No. 5,648,564 (hereinafter the “'564 patent”) discloses a process for forming, isolating and purifying xanthophyll crystals, preferably lutein, from marigold flower petals. It further disclosed that a xanthophyll diester-containing plant extract is saponified in a composition of propylene glycol and aqueous alkali to form xanthophyll crystals. It was also stated that the crystallization is achieved without the use of added organic solvents. The resulting crystals are then isolated and purified to produce substantially pure xanthophyll crystals suitable for human consumption.
The '564 patent also noted that the claimed method had several advantages over the prior art, including its ability to produce luteins suitable for human consumption without using relatively toxic organic solvents during the isolation or crystallization steps. Additionally, the method does not require a recrystallization step.
U.S. Pat. No. 4,048,203 (hereinafter the “'203 patent”) discloses a process for the purification of lutein-fatty acid esters from marigold flower petals or marigold petal oleoresins based on alkanol precipitation.
U.S. Pat. No. 6,007,856 (hereinafter the “'856 patent”) discloses oil-in-water dispersions of &bgr;-carotene and other carotenoids that are stable against oxidation. The dispersions are prepared from water-dispersible beadlets comprising higher concentrations of colloidal &bgr;-carotene.
U.S. Pat. No. 3,998,753 (hereinafter the “'753 patent”) discloses water dispersible carotenoid compositions in liquid or powder form which can be incorporated into pharmaceuticals, cosmetic preparations or animal foodstuffs. It also discloses the processes of preparing these dispersible cartenoid compositions.
U.S. Pat. No. 4,929,774 (hereinafter the “'774 patent”) discloses a stable mixture of an oxidation-sensitive compound which also comprises triglycerides, complexing agents and coating substances.
U.S. Pat. No. 5,536,504 (hereinafter the “'504 patent”) discloses methods for treating tumors with ultramicroemulsions from spontaneously dispersible concentrates containing xanthophyll esters, and new esters with xanthophyll compounds. Further, methods for the production of the concentrates are also disclosed.
SUMMARY OF THE INVENTION
This invention relates to methods of producing lutein and lutein derivatives in a stable form as well as the individual compounds. Additionally, the invention is directed towards specific lutein derivatives which possess a long storage life.
DETAILED DISCLOSURE
Prior to the discoveries of this invention, those of ordinary skill used antioxidant vitamins and/or beadlets to stabilize lutein. These previously used methods primarily prevented the oxidation and the chemical and biological degradation of the lutein. One way in which the present invention is novel is that its stabilization of lutein and its esters goes beyond preventing oxidation. The present invention not only prevents oxidation of lutein and lutein esters, it also protects the lutein compound from destabilizing factors such as oxidants, temperature, humidity, daylight, and UV rays (hereinafter “other factors”) by obtaining lutein and lutein esters which protect against the other factors. It is also noted that these factors effect the stability of lutein and lutein esters during the extraction process, as well as the industrial processing of the same for use in final products. Finally, it was noted that vitamin-based antioxidants can prevent the deterioration of lutein, but it was not known whether they would be effective against the other factors.
The present invention provides a method of protecting lutein against direct and indirect physical, chemical, and biological factors which contribute to the deterioration of lutein and lutein esters. This method protects lutein and lutein esters from both xenobiotic compounds and the environmental elements. The totality of the protective action of the method is referred to hereinafter as XENOGARD (see Table I). The method of the present invention is two-fold. It is based on a unique process of isolation, which provides lutein and lutein esters chemically and less physically stressed in their isolat
Arent Fox Kintner & Plotkin & Kahn, PLLC
Oh Simon J.
Sabinsa Corporation
LandOfFree
Process of obtaining compositions of stable lutein and... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process of obtaining compositions of stable lutein and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process of obtaining compositions of stable lutein and... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3279555