Process for the preparation of xanthophyll crystals

Details Process for the preparation of xanthophyll crystals Process for the preparation of xanthophyll crystals

2002-10-28

2004-06-01

Shippen, Michael L. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

Reexamination Certificate

active

06743953

ABSTRACT:

This invention relates to a process for the preparation of xanthophyll crystals. This invention particularly relates to a process for the preparation of xanthophyll crystals containing high content of trans-lutein and/or zeaxanthin. This invention more particularly relates to a process for the preparation of xanthophyll crystals containing at least 85% total xanthophylls out of which the trans-lutein content is at least 90%, the remaining being zeaxanthin, trace amounts of cis-lutein and other carotenoids.
The xanthophyll crystals' prepared by the process of the present invention are useful as antioxidant, as agents for prevention of cataract and macular degeneration, lung cancer preventive agent, as agents for the absorption of harmful ultra-violet light from sun rays and quencher of photo-induced free radical and reactive oxygen species. The crystals can also be used for the coloration of food and animal/poultry feed.
It is known from various studies that a higher dietary intake of carotenoids is associated with a lower risk for AMD (Age-related Macular Degeneration). The specific carotenoids, lutein and zeaxanthin, which are primarily obtained from dark green leafy vegetables, were most strongly associated with a reduced risk for AMD. Individuals consuming the highest levels of carotenoids had a statistically significant 43% lower risk for AMD. A significant trend was seen for a lower risk for AMD with increasing amounts of carotenoids in the diet. (JM Seddon et al.
Dietary Carotenoids, Vitamins A, C, and E, and Advanced Age
-
Related Macular Degeneration
, Journal of the American Medical Association, Vol. 272, No. 9, pages 1413-1420, (1994))
There is a strong inverse association between higher consumption of dark green vegetables, which contain xanthophylls which are rich in lutein and zeaxanthin, and a decreased risk for oxidative stress related diseases such as cataract and cancer as well. Both lutein and zeaxanthin are reported to possess strong anti-tumor promoting properties. (L Packer, M Hiramatsu, T Oshikawa, (Editors),
Antioxidant Food Supplements in Human Health
, Academic Press, NY, 1999, Pp 223 and Pp 226) Recent studies also reveal that lutein and zeaxanthin can play a useful role in combating conditions which lead to cardiovascular disease, atherosclerosis, skin cancer, ovarian cancer, etc.
Although dark green vegetables are excellent dietary sources of lutein, the isolation and purification of this compound in large quantities from green vegetables is time-consuming and costly due to the high level of chlorophyll pigments. 25 g of a fresh, dark green vegetable such as kale would theoretically provide 10 mg of lutein. (F. Khachik et al, “
Lutein, Lycopene, and Their Oxidative Metabolites in Chemo
-
prevention of Cancer
,” Journal of Cellular Biochemistry, Supplement 22, 236-246, (1995)). Consistent bio-availability and absorption of carotenoids from foods is not as high as supplementation with pure carotenoids.
Extracts from the petals of marigold flowers (also called marigold oleoresin) are an excellent source of lutein esters in large quantities and contain no significant levels of other carotenoids. Lutein and zeaxanthin being fat-soluble nutrients, can be delivered in consistent doses through soft gelatin capsule based supplements, or in stabilized tablets, and other nutritional preparations to overcome deficiencies of diet and improve levels of serum lutein/zeaxanthin, and thereby, the levels of lutein/zeaxanthin in the macula.
BACKGROUND OF THE INVENTION
Carotenoids are yellow, red and orange pigments which are widely distributed in nature Although specific carotenoids have been identified in various fruits and vegetables, bird feathers, egg-yolk, poultry skin, crustaceans and macular eye region, they are especially abundant in marigold petals, corn and leafy vegetables. The correlation between dietary carotenoids and carotenoids found in human serum and plasma indicate that only selected groups of carotenoids make their way into the human blood stream to exert their effect.
Carotenoids absorb light in the 400-500 nm region of the visible spectrum. This physical property imparts the characteristic yellow/red color to the pigments. Carotenoids contain a conjugated backbone composed of isoprene units, which are usually inverted at the center of the molecule, imparting symmetry. Changes in geometrical configuration about the double bonds result in the existence of many cis- and trans-isomers. Mammalian species do not synthesize carotenoids and therefore these have to be obtained from dietary sources such as fruits vegetables and egg yolks. In the recent years, carotenoids have been attributed several health benefits, which include prevention and or protection against serious health disorders.
Carotenoids are non-polar compounds classified into two sub-classes, namely more polar compounds called xanthophylls or oxy-carotenoids and non-polar hydrocarbon carotenes like &bgr;-carotene, lycopene, etc. Both the sub-classes have at least nine conjugated double bonds responsible for the characteristic colors of the carotenoids. Xanthophylls have ring structures at the end of the conjugated double bond chain with polar functions like hydroxyl or keto group. The examples for xanthophylls include lutein, zeaxanthin, capsanthin, canthaxanthin, &bgr;-cryptoxanthin, astaxanthin, etc. As natural colorants and also for their role in human health, xanthophylls containing lutein and zeaxanthin have attracted the renewed attention of scientists and researchers in the biomedical, chemical and nutritional field in recent years.
Lutein and zeaxanthin contribute to yellow and orange-yellow color respectively. Lutein and zeaxanthin can be present in plant material in free form and also in ester form. Lutein is present in green leafy vegetables like spinach, kale and broccoli in the free form while fruits like mango, orange, papaya, red paprika, algae and yellow corn contain lutein in the form of its esters etc. It is also present in the blood stream and various tissues in human body and particularly the macula, lens and retina of the eye.
Marigold (Tagetes erecta) flower petals are a rich source of lutein in its ester form containing fatty acids. Dried marigold flowers contain approximately 1-1.6% carotenoids by weight and lutein esters content accounts for 90% of the total carotenoids (J. I. X Antony & M. L. Shankaranarayana,
Lutein—A Natural Colorant and a Phytonutrient For Eye Health Protection
, The World of Food Ingredients, April/May 64-67, (2001)). The xanthophyll fatty acid esters composition in marigold oleoresin chiefly consists of lutein in its ester form as di-palmitate, myristate-palmitate, palmitate-stearate, dimyristate and monoesters. (W Gau, H. J. Ploschke and C. Wünsche,
Mass Spectrometric Identification of Xanthophyll Fatty Acid Esters from Marigold Flowers
(
Tagetes erecta
)
Obtained by High Performance Liquid Chromatography and Craig Counter
-
current Distribution
, J. Chromatogr., 262,277-284, (1983)).
Lutein obtained by the hydrolysis of lutein esters from marigold have been found to be identical to the lutein found in fruits, vegetables and in human plasma and the macular region. After absorption, the human body cannot distinguish the source of lutein (F. Khachik, A. Steck and H. Pfander,
Isolation and Structural Elucidation of
(13Z, 13′Z, 3R, 3′R, 6′R)-lutein From Marigold
Flowers, Kale, and Human Plasma
, J. Agric. Food. Chem, 47, 455-461 (1999)). Therefore, a widely cultivated and commercially processed raw material like marigold, which is already used by the food and feed industry, is an attractive source for lutein in view of abundant availability and cost considerations.
Essentially, lutein esters and lutein in the free form are commercially important nutraceuticals obtained from marigold flowers. Dried flowers are used for obtaining marigold extract or oleoresin. By subjecting the extract/oleoresin to saponification, xanthophylls in the free form are obtained. The resultant alkali salts of fatty acids obtained from th

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