Drug – bio-affecting and body treating compositions – Plant material or plant extract of undetermined constitution... – Containing or obtained from citrus
Reexamination Certificate
2001-07-24
2003-03-04
Barts, Samuel (Department: 1623)
Drug, bio-affecting and body treating compositions
Plant material or plant extract of undetermined constitution...
Containing or obtained from citrus
C424S744000, C424S725000, C514S027000, C514S449000
Reexamination Certificate
active
06528099
ABSTRACT:
FIELD OF THE INVENTION
The present invention generally relates to a method for selectively obtaining antioxidant rich aqueous extracts from citrus fruits. More specifically, the present invention relates to a method for obtaining a balanced enriched composition of simple phenols, polyphenols, bioflavonoids, flavones and flavonones, to control oxidation processes, from citrus aqueous extracts obtained from cells, core, membrane, frit and peels of citrus fruits.
BACKGROUND OF THE INVENTION
Citrus fruits are a growing industry with significant world importance. Citrus fruits (such as lime, lemons, tangerins, oranges and grapefruits) are utilized primarily for juice recovery.
The by-products industry has also a potential for growth since products like terpaneless oils, pectins, alcohol, wine, natural flavors and aromas, and vinegar have also been produced from citrus fruit residues. The peel residue is the primary by-product, amounting to up to 30% of the fruit mass. Cells, core, membrane and frit residues present additional 20% of by-products. In most cases, this huge amount of waste material is the source for cattle feed only, while in other cases products such as molasses, cold-pressed oils, d-limonene, pectin and flavanoids can be extracted and used. Another method for utilization of the by-products stream, practiced in the last decade by few companies, is concentrating the aqueous extract to obtain higher solid extract which may be sold as such, or upgrading the solid extracts, to improve the organoleptic properties by removal of the so called “undesirable compounds” on resin columns.
The protection that fruits and vegetables provide against diseases, including cancer and cardio- and cerebrovascular diseases, has been attributed to the various antioxidants, especially antioxidant vitamins or provitamins, including ascorbic acid and tocopherols. However, the majority of the antioxidative activity of a fruit or a vegetable may be from compounds other than vitamin C, vitamin E, or &bgr;-carotene. It was recently demonstrated (Pratt, D. F. and Hudson, B. J. F., “Natural Antioxidants in Foods”, Elsevier Applied Science, London (1990), p.171-198) that flavanoids, found in human diets, have also antioxidative activity.
In certain fruits some flavanoids have much stronger antioxidant activities against peroxide radicals than vitamins (vitamin E, vitamin C, glutatione).
Phenolics, in the present invention, are defined as substances possessing an aromatic ring, leaving one or more hydroxyl substituents including their functional derivatives.
The most ubiquitous phenols are polymeric and water-insoluble liquids that are found in vascular plants. However, many of the food phenolics are soluble in water. Phenolics found in feeds generally belong to a subclasses known as phenolic acids, flavonoids, lignans, stilbenes, coumarins and taunins.
When the phenolic skeleton is attached to a sugar glycoside moieties, through an OH group, the materials will be called “glycosyl-flavanoids” or, in short, “flavonoids”. The “glycosyl-flavanoids” are more water soluble and have a more complex structure than the phenolic skeleton materials.
In all phenolic compounds in general, and in most flavanoids and flavonoids, there can be found functional phenolic groups capable of quenching radicals or serving as transition metal scavengers. Also, it seems that certain combinations of phenolics exhibit better activities (synergism) than others.
Flavanones and flavanonols are found mainly in citrus fruits. Some citrus flavanones are naringenin, eriodictyol, hesperidin and isosakuranetin. Some of the most common citrus flavanone-glycosides are natrirutin, naringin, hesperedin and neohesperidin.
Citrus fruits consist mainly of 3-deoxy flavanols (differing from flavanols in position 3, flavanols have an hydroxy group) that are termed flavones. Some common flavones are tangeretin, nobitetin and sinensetin.
Simple phenols, (such as cinarnic and limoneic acid), polyphenols and glycosyl-flavanoids are found mainly in the aqueous fraction of the orange, while the flavanones and flavanonols are less water soluble and expected to reside in the “peel oils”. (naringin is water soluble whereas naringenin is more “oil soluble”).
Today's world is very aware of the health benefits offered by citrus fruits in terms of vitamins and other additives, and the consumption of citrus juice and drinks is increasing dramatically every year.
Naringin (in grapefruits) and hesperidin (in oranges) are the two major flavanoid-glycosides present in the citrus fruits, and are primarily concentrated in the peel and the tissue of the fruit. Attempts were made to extract and purify both flavanoids (Braddock, R. J., By-products of citrus fruit, Food Technology, 9,1995 p.74-77), but the anti oxidation capacity of orange, grapefruit, or any other specific citrus extracts, was not explored. Furthermore, no data is available regarding fractionation and enrichment of the possible active matter (bioflavonoides and/or simple and polyphenols) in each of the fruit fractions (cells, core, frit and peels). The existing debittering technology relates to recovery of bioflavenoids only (mainly naringin and hesperidin), by method of alkaline water extraction utilizing caustic solutions for pH control.
The present existing technologies are based on absorption/adsorption and resin extraction, and the removal/recovery of the products are not selectively done. Moreover, the alkaline conditions could change chemical structures, mainly by hydrolyzing the ester bonds between the sugars and the flavonoids and partially oxidizing the phenolic groups. In addition, the existing technology encounters environmental hazards.
Various attempts were made to obtain antioxidant materials from fruits. DE patent No. 2525590 teaches a process for obtaining, via solvent extraction of oil a non-specific segment, which contain (among other compounds) some bioflavonoids. However, DE patent No. 2525590 relates only to the oily phase of the citrus fruit and not to the aqueous (juice) fraction. EP patent No. 657169 describes a method for obtaining a fruit polyphenol from unripe fruits of Rosaceae by subjecting the unripe fruits of Rosaceae to pressing and/or extraction and then purifying the resulting juice or extract. However the invention relates only to the unripe fruits of Rosaceae and not to citrus fruits. Hence, the polyphenols obtained are of different structures and properties.
Up to this date no direct correlation between each of the above phenolic compounds in citrus fruits to their “antioxidant activity” was shown.
In the present invention it is shown, for the first time, that the composition of certain polyphenols, simple phenols and/or flavones and/or flavanoids derived from citrus fruit, can offer, in themselves and combined with each other, antioxidant capacities that are more attractive than many known synthetic or natural antioxidants from common vegetables or fruits.
As opposed to the work done up to this date, the present invention relates to an environment friendly method for selectively extracting unique and well-balanced synergistic compositions of phenolics (combinations of simple phenols, polyphenols and flavonoids) from citrus fruits, that exhibit strong antioxidant capacities, superior to the isolated flavanoids such as naringin or herperidin.
The method of the present invention also differs from the work done up to date in that, otherwise discarded compounds (“undesirable compounds”), are eluted from the resin, allowing for the possibility, during the elution process, to selectively enrich each of the fractions by its active matter. This additional elution step gives a significant advantage over the alkaline or acidic “water extracted fractions” of the methods used today, being “blind” to their internal product distribution and activity.
The present technology offers the additional advantage of selectivity of extraction/recovery by utilizing advanced citrus down stream engineering based on chromatographic selective separation that was not applied for the purpos
Agmon Gilad
Garti Nisim
Pintus Eli
Adumim Chemicals Ltd.
Barts Samuel
Khare Devesh
Lowe Hauptman & Gilman & Berner LLP
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