Drug – bio-affecting and body treating compositions – Antigen – epitope – or other immunospecific immunoeffector – Conjugate or complex
Reexamination Certificate
2000-01-12
2001-05-01
Weber, Jon P. (Department: 1651)
Drug, bio-affecting and body treating compositions
Antigen, epitope, or other immunospecific immunoeffector
Conjugate or complex
Reexamination Certificate
active
06224877
ABSTRACT:
FIELD
The present invention relates to a process for extraction of curcuminoids from curcuma species. The present invention particularly relates to extraction of curcumionids using aqueous hydroptrope solutions for the first time.
BACKGROUND
Curcumin (C
21
H
20
O
6
) has many industrial uses. Curcumin is obtained from plants mainly Curcuma. Curcumin, a major constituent of rhizomes of Curcuma species, is present in the form of two related compounds viz. demethoxycurcumin and bisdemethoxycurcumin (together known as curcuminoids). Curcuminoids are used extensively as a food-colouring agent, natural antioxidant, spice, and condiment and for medicinal purposes. It has shown potent anticancer activity [Kuttan, Ramadasan; et. al., Cancer Lett. (Shannon I rel.) 1985, 29(2), 197-202]. Curcuminoids also has potential as an antiviral agent. It has been proven as a modest inhibitor of HIV-1 and HIV-2 proteases [Sui, Z; et. al,. Biorg. Med. Chem. 1993, 6, 415-422].
PRIOR ART RELATING TO THE INVENTION
In the prior art, there are many processes for extraction of curcuminoids from curcuma species. The relevant prior art processes are indicated herebelow:
Sastry B. S. [Res. Ind. 1970, 15, (4), 258-60] described an extraction process for the extraction of curcuminoids from turmeric wherein the curcuminoids were extracted with acetone followed by petroleum ether. Other solvents used for extraction are ethanol, ethyl acetate and benzene. The extraction of curcuminoids into these organic solvents was not very selective, as other compounds like oleoresins were extracted reducing the purity of curcuminoids. This makes post-extraction processing cumbersome.
Myagi, Hisashige et al (Jpn. Kokai Tokyo Koho JP 06,69,479 [9409,479] (CL. C07C49/255), Jan. 18, 1994, Appl. 92/169,647, Jun. 26, 1992; 5pp.) patented a process for extraction of curcuminoids using supercritical carbon dioxide. The supercritical carbon dioxide was actually used for extracting essential oils and then curcuminoids were extracted from
Curcuma longa
using mixture of ethanol and water. This process using supercritical fluid extraction is not economical and curcuminoids extracted is then converted to a water soluble curcumin cyclodextrin complex. Chassagnez, A; et al [Cienc. Technol. Aliment. 1997, 17 (4), 399-404], carried out a pretreatment on
Curcuma longa
material before extraction, using supercritical carbon dioxide and determined that the curcuminoids extraction largely depends on this pretreatment.
Ran, Qiliang; and Zhou, Xianrong [Shipin Kexue (Beijing) 1988, 101, 12-15], extracted curcuminoids from Curcuma with alkaline water (pH~9). The curcuminoids was recovered by precipitation at pH 3-4. The product contained 82.5% curcuminoids. However, the curcuminoids were unstable in alkaline conditions and the degradation rate rapidly increases from pH 7.45 to a maximum of about 10.2.[Price Lisa C; and Buescher. R. W; J. Food Sci. 1997, 62 (2), 267-269].
Most of these prior art processes relate to the extraction of
Curcuma longa
oleoresin containing curcuminoids and other volatile oils. Curcuminoids containing oleoresin is then solvent extracted and recrystallised to obtain pure curcuminoids. These conventional processes are carried out using a number of steps that often present difficult operating conditions and result in high cost of production.
SUMMARY
The present invention relates to a process for extraction of curcuminoids from curcuma species using hydrotrope solutions.
OBJECTS
The main object of the present invention is to provide a very effective process for the extraction of curcuminoids from Curcuma species.
Another object is to provide a cost-effective process for the extraction of curcuminoids from Curcuma species in a substantially pure form using the phenomena of hydrotropy.
Yet another object relates to the use a suitable hydrotrope for selective extraction of curcuminoids from Curcuma species followed by dilution of the extract phase to precipitate curcuminoids in pure form.
Still another object is to provide a simple two step process for the selective extraction of phytochemicals like curcuminoids which successfully exploits the ability of hydrotropes to dissolve the otherwise water insoluble organic compounds in aqueous solution.
One more object is to provide a process for the extraction of curcuminoids from
Curcuma longa
in the first step without using an organic solvent or excessive temperature to retain the purity of curcuminoids.
DETAILED DESCRIPTION
To meet the above objects and the others, the present invention for the first time proposes a very efficient process for the extraction of curcuminoids from Curcuma species. In other words, the present invention provides a cost-effective process for the extraction of curcuminoids from Curcuma species in a substantially pure form using the phenomena of hydrotropy. The present approach is directed to find a suitable hydrotrope for selective extraction of curcuminoids from Curcuma species followed by dilution of the extract phase to precipitate curcuminoids in pure form.
Preferably, the object of the invention is to provide a simple two step process for the selective extraction of phytochemicals like curcuminoids which successfully exploits the ability of hydrotropes to dissolve the otherwise water insoluble organic compounds in aqueous solution. The first step involves the selective extraction of curcuminoids from Curcuma species and its solubilization in the aqueous hydrotrope solution. The second step involves the recovery of curcuminoids by simple dilution with water as most of the curcuminoids precipitates out.
In another embodiment of the invention, the extracted curcuminoids is recovered from the aqueous hydrotrope solution by extraction with an organic solvent followed by desolventisation.
In yet another embodiment, the present process provides extraction of curcuminoids from
Curcuma longa
in the first step without using an organic solvent or excessive temperature to retain the purity of curcuminoids.
The Curcumin of Formula 1, de-methoxy curcumin of Formula 2 and bis (de-methoxy ) curcumin of Formula 3 together known as curcuminoids have been extracted from the rhizomes of Curcuma species.
Accordingly, the present invention provides a process for the extraction of curcuminoids from Curcuma species, which comprises:
(i) contacting Curcuma species with an aqueous hydrotrope solution at a temperature in the range of 0-100° C. for preferential extraction of curcuminoids from the Curcuma species and separating the solution obtained from the solid, and
(ii) recovering the curcuminoids from the solution obtained at the end of step (i) by known methods.
In an embodiment, the methods for recovery of curcuminoids from the solution obtained at the end of step (i) are selected from extraction or dilution method.
The rhizomes of Curcuma species such as
Curcuma longa
and
Curcuma aromatica
in pulverized form, preferably in the mesh size of 5 to 300 are brought in intimate contact with an aqueous solution of hydrotrope in the form of a slurry in a stirred vessel. In the process of invention when the contacting is done in the stirred vessel the Curcuma species powder is added to the aqueous hydrotrope solution of concentration in the range of 0.1 mol/L to 5.0 mol/L. After the aforementioned components are brought together the mixture usually in the form of slurry is agitated for a period sufficient for the extraction of curcuminoids to take place. A typical mixing time is in the range of 15 minutes to 24 hours depending upon the concentration of hydrotrope and the speed of agitation. The mixing is conducted at a selected temperature from 0° C.-100° C. preferably at room temperature of 30° C. and atmospheric pressure.
In an embodiment of the invention the curcuminoids are recovered from the aqueous solution of hydrotrope obtained in step (i), after dilution with water or without dilution, by extraction with an organic solvent selected from the group of aromatic and aliphatic hydrocarbons such a
Dandekar Deepak Vijay
Gaikar Vilas Gajanan
Council of Scientific and Industrial Research
Patten Patricia
Perkins Coie LLP
Weber Jon P.
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