Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Reexamination Certificate
2003-02-07
2004-05-25
Killos, Paul J. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C562S498000
Reexamination Certificate
active
06740778
ABSTRACT:
This application claims priority under 35 U.S.C. §§ 119 and/or 365 to 2000-240347 filed in Japan on Aug. 8, 2000; the entire content of which is hereby incorporated by reference.
TECHNICAL FIELD
The present invention relates to a method for the preparation of oleanolic acid and/or maslinic acid as well as physiologically acceptable salts thereof and, in particular, to a method for the preparation of oleanolic acid and/or maslinic acid from olive plant (
Olea europaea
L.) and/or products derived from the olive oil-manufacturing processes.
BACKGROUND OF THE INVENTION
Olive is a plant belonging to genus olive of family Oleaceae, which has habitually been used as a raw material for foods. Olive is a plant widely cultivated for a long time and has presently and typically been grown on a large scale in the districts along the shore of the Mediterranean. Regarding the applications thereof, it is quite important and is not only used as oil stuffs such as olive oil in almost all the countries of the world including Japan and the United States, not to speak of the European countries, but also used as salt-preserved foods or materials for cosmetics and even as a herb (a medical plant). In addition, the olive oil cake has widely been used as a fertilizer, a feed and/or a fuel. In other words, it would be concluded that the olive is a vegetable material relatively stably available and highly safe for the human body.
Recently, the olive oil obtained through the oil expression of olive plant has been known as vegetable oil relatively hardly oxidized. Moreover, polyphenols present in the olive oil in trace amounts have attracted special interest and a variety of studies concerning, for instance, the physiological effects thereof have been conducted (see, for instance, International Olive Oil Council, New Food Industry, 1992, Vol.34, No. 4, pp. 28-52).
As another component of olive plant, it has been known that leaves of olive plant contain oleanolic acid and there have been elucidated, for instance, physiological effects thereof.
Oleanolic acid is a kind of oleanane type triterpenes and a compound present in, for instance,
Swertia japonica
Makino,
Eugenia caryophyllata
Thumb. (Clove), the rind of grapes and leaves of olive plant in its free state and in
Panax japonicus
C. A. Meyer,
Daucus carota
L. and
Beta vulgaris
L. in the form of saponin. Moreover, it may likewise be commercially available. There have conventionally been conducted a variety of studies concerning, for instance, physiological effects of oleanolic acid and it has been known that oleanolic acid possesses various effects such as a carcinogenic promoter-inhibitory effect (Japanese Un-Examined Patent Publication (hereunder referred to as “J.P. KOKAI”) Sho 63-57519), an anti-inflammatory effect and an effect of promoting wound-healing (Japanese Examined Patent Publication (hereunder referred to as “J.P. KOKOKU”) Hei 4-26623), an effect of inhibiting alcohol-absorption (J.P. KOKAI Hei 7-53385) and an effect of promoting new hair growing (J.P. KOKAI Hei 9-157139).
On the other hand, maslinic acid is a kind of oleanane type triterpenes and is a compound present in
Olea europaea
L. (olive),
Humulus lupulus
L. (hops),
Mentha arvensis
L. var.
piperascens
Holmes (Japanese mint),
Punica granatum
L.,
Eugenia caryophyllata
Thumb. (Clove),
Salvia officinalis
L. (sage) and
Zizyphus vulgaris
Lam. Var.
inermis
Bunge, but it is not distributed so widely in the nature. Maslinic acid has been known to have an anti-inflammatory effect and anti-histamic effect.
As has been discussed above, oleanolic acid and maslinic acid are useful substances and therefore, it would be necessary to ensure the stable supply of these triterpenes. Regarding, in particular, maslinic acid, however, naturally occurring plant materials containing the same are deficient and there has not yet been established any effective method for preparing the same. Accordingly, a problem arises such that these compounds cannot stably be supplied and that they require high production coat.
Moreover, there has not yet been known any method for preparing either or both of oleanolic acid and maslinic acid from the same natural raw substances in highly purified states and any method for industrially mass-producing these substances in high efficiency.
DISCLOSURE OF THE INVENTION
Accordingly, it is an object of the present invention to provide a method for preparing oleanolic acid and/or maslinic acid and, in particular, to a method for industrially mass-producing these compounds from olive plant and/or products obtained from olive oil expression processes.
The inventors of this invention have conducted various investigations of methods for preparing oleanolic acid and/or maslinic acid and physiologically acceptable salts thereof starting from olive plant for achieving the foregoing object, have found a method for quite efficiently preparing these compounds and have thus completed the present invention.
The present invention thus relates to a method for preparing oleanolic acid and/or maslinic acid and physiologically acceptable salts thereof, which comprises the steps of extracting olive plant and/or products obtained in the olive oil-manufacturing processes with water and/or an organic solvent and then concentrating and/or conducting fractionation-purification treatment of, the resulting extract.
In this respect, oleanolic acid and maslinic acid as subjects of the present invention are substances represented by the following structural formulas (I) and (II), respectively. Moreover, the physiologically acceptable salts thereof are those derived from the —COOH groups in the structural formulas (I) and (II) and include those contained in olive plant and products obtained in the olive oil-manufacturing processes and those formed by treating oleanolic acid and/or maslinic acid prepared by the method of the present invention with basic mediums and/or basis substances. The kinds of salts are not restricted to specific ones inasmuch as they are currently used in, for instance, cosmetics or pharmaceutical composition and foods and beverages.
The present invention preferably relates to a method for preparing oleanolic acid and/or maslinic acid, which comprises the steps of extracting olive plant and/or products obtained in the olive oil-manufacturing processes with water and/or an organic solvent and then treating the resulting extracted substance and/or extracted liquid with an acidic medium and/or an acidic substance; and a method for preparing physiologically acceptable salts of oleanolic acid and/or maslinic acid, which comprises the steps of extracting olive plant and/or products obtained in the olive oil-manufacturing processes with water and/or an organic solvent and then treating the resulting extracted substance and/or extracted liquid with a basic medium and/or a basic substance.
According to preferred embodiments of the present invention, the olive plant preferably used in the foregoing method is at least one member selected from the group consisting of fruits, seeds, rinds, leaves, stems and buds or germs of olive and dried products, pulverized products and defatted products of these ingredients and the products obtained in the olive oil-manufacturing processes preferably used in the foregoing method are at least one member selected from the group consisting of strained lees, extraction residues, squeezed oil, extracted oil, degummed oil scum, deacidified oil scum, dark oil, waste decoloring agent, deodorized scum, oil-expressed juice, waste water and waste filter mediums.
The organic solvent used in the extraction step is a hydrophilic organic solvent, in particular, a water-containing hydrophihc organic solvent because of its industrial advantages such as good ability of penetrating into plant's tissues and achievement of high extraction efficiency. More specifically, the organic solvent is preferably at least one member selected from the group consisting of mixed solvents comprising chloroform and methanol and/or ethanol, pyridine, ethanol, dimethyls
Kuno Noriyasu
Shinohara Gou
Killos Paul J.
The Nisshin Oillio, Ltd.
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