Drug – bio-affecting and body treating compositions – Plant material or plant extract of undetermined constitution... – Containing or obtained from zingiberaceae
Reexamination Certificate
1996-10-28
2002-08-27
Tate, Christopher R. (Department: 1651)
Drug, bio-affecting and body treating compositions
Plant material or plant extract of undetermined constitution...
Containing or obtained from zingiberaceae
C424S725000, C514S824000, C514S825000
Reexamination Certificate
active
06440468
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The present invention fits in the technical field of the obtainment of plant extracts with different medicinal, cosmetic, dietetic applications, etc.
More especially, the present invention provides a method for obtaining apolar and polar extracts of Curcuma that have important applications as catchers of free radicals and antiageing agents.
PRIOR ART OF THE INVENTION
Curcumin and other curcuminoids, such as the essential oils obtained from plant extracts of the Curcuma and in general of the Zingiberaceae family, are useful for the treatment and prophylaxis of different diseases. For example, one can cite: EP568,001 (antiviral agents), EP440,885 (antiinflammatory agents), EP319,058 (against loss of hair), EP256,353 (treatment of malabsorption syndromes), U.S. Pat. No. 5,108,750 U.S. Pat. No. 4,906,471, U.S. Pat. No. 4,842,859 platelet antiaggregation agents and anticholesterol agents); WO88/05304 (against hepatitis B and AIDS), WO88/08713 (treatment of neurological disorders), U.S. Pat. No. 4,568,546 (antivenin agent). The antioxodizing and dyeing properties of curcumin and of the derivatives thereof are also known, thus, they are widely used in the food and cosmetic industries as natural preservatives (U.S. Pat. No. 5,266,344, KK KOBE SEIKO SHO).
On the other hand, it is known that the excess of reactive oxygen and free radicals in tissues produces alterations that can lead to premature ageing of cells and the onset of different diseases. Giving the growing concern for this phenomenon, it is not surprising that there are numerous documents about the preparation of plant extracts with antioxidizing effects, catchers of free radicals and therefore useful in the prevention of ageing of cells. However, in the specific case of
Curcuma longa
extracts the number of documents found is not very large and for the most part they are not patent literature.
Among the bibliographic references of the most interesting patents existing in the data banks, application FR2,655,054 (PACIFIC CHEMICAL) about the cellular protection agents contained in curcuminoids (curcumin, 4-hydroxycinnamoyl (pheruloly)methane, bis (-hydroxycinnamoyl) methane, etc.) obtained from
Curcuma longa,
ascorbic acid and/or dismutase superoxide (DSO) stands out. Curcuminoids have a known antioxidizing effect, as well as ascorbic acid and DSO that carry out a synergic effect.
On the other hand, the antiinflammatory activity of curcuminoids can also result from their antioxidizing activity. In this sense, application EP550,807 (STEIGERWALD ARINEIMITTELWERK) describes
Curcuma longa
preparations useful for the treatment of inflammatory diseases associated with the excess production of leukotrienes and prostagalins (Crohn's disease, bronchial asthma, psoriasis, etc.) According to this document, curcumin carries out its antiinflammatory action on the one hand participating in the reactions of elimination of active oxygen and free radicals and on the other hand by inhibiting the cyclooxygenase and lipooxygenase, enzymes responsible for the synthesis of prostaglandins and leukotrienes respectively.
In connection with the methods of extraction of the polar and apolar fractions of the
Curcuma longa
rhizomes, they are conventional methods that use usual solvents (liquids in normal conditions) or else liquid CO
2
or NO
2
or in supercritical conditions, which is likewise usual for the extraction of fragrances and essential from plants “Carbon dioxide extracted ingredients for fragrances”, Flavours & Fragrances O-5M385P, North Albert Road, Reigate, Surrey RH2 9ER, England.)
However, it is a field of noteworthy interest in which it is still desirable to obtain pure extracts, to discover possible new applications of the same in the medical-pharmaceutical fields, in cosmetics, dietetics, etc.
Along these lines, the present invention provides apolar and polar extracts of
Curcuma longa
with important properties as catchers of free radicals and, consequently, antiageing agents of cells. Likewise, these extracts have shown the capacity to reduce plasma levels of lipid peroxides in humans.
On the other hand, according to the bibliographic data it is known that oxygenated radicals generated in cells are controlled by the cell defense system. The excess generation of such radicals can exceed the protective capacity of the defense system and lead to oxidation of the cell components, proteins, lipids and DNA. These oxidative processes are relevant in the pathogenesis of diseases such as arteriosclerosis and rheumatoid arthritis.
DETAILED DESCRIPTION OF THE INVENTION
Just as it is indicated in the title, the present invention refers to a method for obtaining apolar and polar extracts of Curcuma and the applications of these extracts.
Plants of the Curcuma genus and, especially,
Curcuma longa
are tropical plants known from ancient times that belong to the Zingiberaceae family and they originated in Asia. Dried Curcuma rhizomes were already used in Asia as a spice and textile dye. They were also used in popular medicine to treat stomach ailments.
In the last few years, new pharmacological applications have appeared in the scientific literature: antibacterial activity, antiinflammatory activity, lipid peroxidation capacity, antihepatoxic capacity and antitumorigenic capacity.
Curcuma extracts are yellow pigments called curcuminoids, basically comprised of: curcumin (dipheruloylmethane), demethoxycurcumin (hydroxycinnamoylpheruloyl-methane) and bisdeoxycurcimin (dihydroxycinnamoylmethane).
The method of the present invention, for obtaining the apolar extract of
Curcuma longa
is characterized in that it comprises the following operations:
a) subjecting the previously cut, dried and powdered Curcuma rhizomes to a continuous extraction process for 48 hours, using an organic solvent in a rhizome:solvent ratio of 1:7 weight/volume, carrying out the process in a stationary system to prevent losses of the solvent, for which purpose the temperature of the extraction boiler is adjusted;
b) filtering the extraction mixture resulting from step (a) and evaporating the solvent from the filtrate obtained at reduced pressure obtaining a characteristic brown colored oleoresin as a dry residue;
c) dissolving the oleoresin resulting from step (b) in hot ethyl acetate, in a proportion of 50% w/w and then letting the solution cool down to room temperature for about 24 hours. An orange-colored precipitate that is separated by filtration appears;
d) drying the filtrate coming from the previous step at reduced pressure to obtain a second oleoresin darker than the previous one, whose curcuminoid content is from 20 to 25%;
e) recrystallizing the resulting precipitate in ethyl acetate 50% (w/w) to obtain a solid with a purity in curcuminoids higher than 90%.
On its part, the method of the present invention for obtaining the polar extract of
Curcuma longa
is characterized in that it comprises the following operations:
a) subjecting the previously cut, dried and powdered
Curcuma longa
rhizomes to an extraction process with water, keeping them in maceration for about 24 hours at a temperature between 50 and 70° C.;
b) filtering the extraction mixture resulting from step (a) and evaporating the water from the filtrate this obtained at reduced pressure to obtain a residue that is a hygroscopic solid corresponding to the polar extract of
Curcuma longa.
Likewise, the method of the present invention is carried out by supercritical extraction, for which purpose the Curcuma rhizome, previously cut, dried and powdered is extracted with ethanol/CO
2
and at a pressure of about 260 bar, to obtain the corresponding apolar extract with a purity in curcuminoids of 90%. The apolar extract thus obtained is identical to the one obtained by extraction with solvents according to what is shown by the spectroscopic and chromatographic data thereof. In the same way, but using water as a cosolvent, the polar extract, whose fine layer chromatography totally coincides with that of the extract obtained by maceration in water indicated above, is o
Diaz Alperi Joaquin
Quintanilla Almagro Eliseo
A.S.A.C. Pharmaceutical International, A.I.E.
Klauber & Jackson
Tate Christopher R.
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