Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Reexamination Certificate
2002-07-30
2004-05-18
Carr, Deborah D. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
C554S020000
Reexamination Certificate
active
06737535
ABSTRACT:
INTRODUCTION
The present invention relates to a novel trans-lutein enriched xanthophyll ester concentrate and a process for its preparation. The present invention, more particularly, provides a novel trans-lutein enriched xanthophyll ester concentrate, in which the xanthophyll esters comprise 90-95% of trans-lutein esters, 0-5% of cis-lutein esters and 3.5-6% of zeaxanthin esters. The novel trans-lutein enriched xanthophyll esters concentrate of the present invention is useful for human consumption, either as nutraceuticals, as nutritional supplements, as food additives and also for colouring feeds. As nutraceuticals, the concentrate of the present invention has particular use as an agent for protecting against eye diseases due to aging, cataract and macular degeneration and for reducing the risk of developing certain diseases like cancer, cardiovascular diseases, etc., as well as for use as an antioxidant. The concentrate of the present invention also has better stability and bio-availability.
The invention also provides a process for the preparation of the above novel translutein enriched xanthophyll ester concentrate from oleoresin, especially from marigold oleoresin.
BACKGROUND OF THE INVENTION
Carotenoids are one of the most abundant kind of pigments widely distributed among plants and are considered to be non-toxic to human consumption. Xanthophyll esters are included as a group of these carotenoids. They essentially are di- or mono-fatty acid esters of the carotenoids consisting chiefly of di-palmitate, di-myristate, di-stearate as lutein and zeaxanthin. Zeaxanthin ester is a pigment contained in berries such as those of genus Lycium chinense (Chinese wolfberries) and Physalis. Lutein esters are pigments that give the yellow/red color to fruits, such as oranges, peaches, papayas, mangoes, etc. Lutein esters also are present in many floral parts particularly marigold flowers of genus Tagetes. Xanthophyll esters are generally found in nature as tran-sxanthophyll isomers and also in cis-isomeric form in trace amounts mainly formed due to adverse conditions of heat and light. Lutein esters of higher purity and naturally preserved trans-isomeric form are preferred for use in human requirements because of their better stability and bioavailability.
The above carotenoids mainly being fat-soluble have limited applications in foods. Dihydroxy carotenoids (xanthophylls), lutein and zeaxanthin are compounds valued as poultry feed colourant and as a health nutritional supplement. Xanthophyll esters form the major colouring component in marigold flowers and its extracts.
Marigold flowers are one of the richest sources of trans-lutein esters found in nature. Dried and ground marigold flowers have been used commercially for more than three decades as a pigmenting agent in poultry and animal feeds and as a food coloring agent. For many years, it has been used as the starting material for the production of marigold extracts containing xanthophyll esters, which is a commercially important ingredient. Reference in this context may be made to U.S. Pat. No 3,539,686, (1970) and German Patent No 1,224,597.
Recently, these and other carotenoid esters both in mono-and di-ester forms have been reported to be naturally occurring in several fruits and vegetables (D. E. Breithaupt and A. Bamedi;
Journal of Agricultural Food Chemistry
, Vol. 49, 2064-2070, (2001); F. Khachik, G. R. Beecher and W. R. Lusby,
Journal of Agricultural Food Chemistry
, Vol. 36,938-946, 1988). Xanthophyll esters with higher amounts of trans-lutein content have gained importance, and are preferred because of their natural occurrence in foods, better stability and bio-availability (Bowen and Clark, U.S. Pat. No. 6,313,169, November 2001; Herbst et al.
FASEB Journal Abstract No
. 11, 2587, (1997); A. Subagio, H. Wakaki and N. Morita,
Biosci.Biotechnol.Biochem
., 63 (10), 1784-1786, (1999)). Further, the colouring power of trans-lutein (absorption maximum at 474 nm) is superior to cis-lutein (absorption maximum at 468 nm)(W. L. Hadden, R. H. Watkins, L. W. Levy, E. Regalado, D. M. Rivadeneira, R. B. van Breemen and S. J. Schwartz,
Journal of Agricultural Food Chemistry
, Vol. 47,4182-4194 (1999)).
U.S. Pat. No. 4,048,203, (1977) (Philip) describes a process for the extraction of lutein esters starting from marigold extract prepared by treating dried and ground marigold petals (1 kg) with petroleum ether at room temperature. The extract was obtained by removal of the solvent under vacuum at 50° C. The oleoresin (65 g) obtained through this process was dissolved in hot isopropanol at 75° C. and the solution was filtered through a sintered glass funnel to remove undissolved materials. The filtrate was then cooled to 15° C. and the precipitated lutein fatty acid esters were recovered by filtration through a sintered glass funnel. The esters were dried under a vacuum at 30° C. to yield 21 g lutein fatty acid esters with a 51% lutein esters content.
However, in this patent there is no indication of the content of trans and/or cis-isomeric forms. Further, due to alkanol precipitation at a high temperature, a considerable amount of trans-lutein esters is converted into cis-isomeric form, which is considered undesirable for use as human nutritional supplements. Further, the tinctorial shade/hue of the cis-isomeric form is relatively poor.
Tycozkowski and Hamilton (
Poultry Science
, 70, 651-654 (1991)) reported a process for the preparation of trans-lutein di-esters by reacting free lutein (prepared from marigold oleoresin after saponification) with an acyl chloride. In this process, a saponified extract of marigold petals containing 14.70 mg lutein per gram was the starting material. 1 g of the material was added with 10 ml of a solvent mixture HAET (hexane: acetone: toluene: absolute alcohol in the ratio 10:7:7:6 respectively). The mixture was stirred well followed by the addition of 10 ml of hexane and then 7 ml of 10% aqueous sodium sulfate. After allowing the mixture to stand for 1 hour, the clear top layer was separated, condensed under nitrogen atmosphere to one-third its initial volume, and placed at a temperature of 4° C. until crystals were formed. The crystals were filtered, washed with cold hexane, and dissolved in a minimal amount of warm hexane: acetone (80:20 v/v) for recrystallization. The final crystals were stored under nitrogen gas in the dark.
Lutein di-esters were prepared by reaction of free lutein with acyl chloride. In one example, 20 mg of lutein was dissolved in 15 ml pyridine followed by the addition of 1 ml of palmitoyl chloride (99+%), and the mixture was incubated at 50° C. for 2 hours. Later the reaction mixture was transferred to a separatory funnel with the addition of 30 ml of HAET solution and hexane. The mixture was then washed twice with equal volumes of 10% aqueous sodium sulfate (Na
2
SO
4
) and twice with distilled water. After drying the upper layer with anhydrous sodium sulfate (Na
2
SO
4
), the solvent was evaporated under nitrogen gas and lutein di-ester residue was stored under nitrogen gas in the dark at −20° C.
However, this synthesis-based method is not preferred because of the presence of associated impurities and non-availability of the naturally occurring lutein di-esters (xanthophyll esters). Therefore, the product resulting from the method is not equivalent to the similar product produced or derived from a natural source, such as marigold flowers or their extracts.
Recently, U.S. Pat. No. 6,191,293; (2001) to Levy described a method for the preparation of trans-xanthophyll ester concentrates having a trans-xanthophyll esters content at least 4 times greater and preferably at least nine times greater than the cis-xanthophyll esters content. The patent reports that xanthophyll esters concentrates having a total xanthophyll esters content of at least 40% by weight and preferably greater than about 55% by weight are obtained by the process disclosed therein.
The method of preparation comprises contacting plant material containing xanthophyll esters with a hydrocarbon so
Carr Deborah D.
Kancor Flavours and Extracts Limited
Merchant & Gould P.C.
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