Simmondsin processing methods and products

Details Simmondsin processing methods and products Simmondsin processing methods and products

2001-08-24

2003-09-16

Tate, Christopher R. (Department: 1651)

Drug, bio-affecting and body treating compositions

Plant material or plant extract of undetermined constitution...

C424S776000, C514S023000, C514S025000, C536S017900

Reexamination Certificate

active

06620442

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to simmondsin extracts, and particularly, to a process of reducing odour, bitterness, astringency and pungency of a simmondsin extract.
BACKGROUND OF THE INVENTION
Jojoba has a unique wax ester oil, which is widely used in cosmetics and lubricants. After oil extraction, the de-fatted and partially de-fatted jojoba meals contain several compounds such as simmondsin and its analogues, phytic acid, trypsin and tannin.
Simmondsins and its analogues are unique components of jojoba and have been the subject of scientific studies for about 30 years. The structures of simmondsins have been elucidated and their chemical properties defined. In this document, the term “Simmondsins” (capitalised, plural) is used to indicate three analogues of simmondsin, which include simmondsin, didemethyl simmondsin and simmondsin ferulate.
An important property of simmondsin and simmondsin ferulate is their reported ability to cause a significant food intake reduction in animals. Didemethyl simmondsin is thought not to have such efficacy. Currently, the reduction of food intake induced by simmondsin and simmondsin ferulate is attributed to the stimulation of satiation, probably through the stimulation of cholecystokinin production (Cokelaere, et al.,
Proceedings of the Ninth International Conference on Jojoba and Its Uses and of the Third International Conference on New Industrial Crops and Products,
135-136, 1996; Flo et al.
Proceedings of the Ninth International Conference on Jojoba and Its Uses and of the Third International Conference on New Industrial Crops and Products,
135-136, 1996). Simmondsin ferulate is reported to have about 67% efficacy compared to simmondsin in tests involving rats (Cokelaere, et al., 1996). The food intake reduction induced by simmondsin and simmondsin ferulate may be useful in weight control of animals. Simmondsin and simmondsin ferulate may be extracted from jojoba meal, or any other plant containing Simmondsins, and may be used for the purpose of weight control in animals and humans.
Simondsin and its analogues may be extracted with organic solvents (i.e. acetone, methanol, ethanol and ethyl acetate) from de-fatted jojoba meal and purified by chromatographic techniques such as high performance liquid chromatography (Booth et al.,
Life Science
15: 1115-1120, 1974; Verbiscar and Banigan,
Journal of Agricultural and Food Chemistry
26: 1456-1459, 1987; Dangreau and Cokeraere, Duch Patent No. 8901639, 1991; Van Boven at al.,
Journal of Agricultural and Food Chemistry
41: 1606-1607, 1993; Van Boven at al.,
Journal of Agricultural and Food Chemistry
41: 1118-1121, 1994a; Decuypere and Cokelaere, U.S. Pat. No. 9,425,035, 1994; Van Boven et. al.,
Proceedings of the Ninth International Conference on Jojoba and Its Uses and of the Third International Conference on New Industrial Crops and Products,
135-136, 1996; Abbot at al., U.S. Pat. No. 9,962,530, 1999). However, the technique of high performance liquid chromatography may be too costly to be economically feasible for industrial scale production of simmondsin products.
Erhan et al. (
Industrial Crops and Products
6: 147-154, 1997) prepared a concentrate of Simmondsins in a pilot scale operation using the technique of water extraction, which was followed by ultrafiltration and spray drying. The final powdery concentrate reportedly contained about 41.3% Simmonsins.
Problematically, crude extracts or concentrates of Simmondsins generated through organic solvent or water extraction of de-fatted jojoba meal may contain odour and bitter components, and may have a strong astringent and pungent taste. Without further purification, the extract of Simmondsins may therefore not be palatable.
SUMMARY OF THE INVENTION
It has now been unexpectedly discovered that simmondsin ferulate may be significantly responsible for the unpalatability of Simmondsins extracts that have been extracted using prior art processes. It has further been unexpectedly discovered that simmondsin ferulate may be selectively reduced or removed from the extracts during the extraction processes, or at any time thereafter, by treatment with a carbonaceous adsorbent, such as activated carbon, in accordance with the processes of the present invention.
In an embodiment of the present invention, there is provided a process for reducing odour, bitterness, astringency or pungency of a Simmondsins extract by dissolving the Simmondsins extract in a solvent (if the Simmondsins extract is in a dry form), reacting the liquid Simmondsins extract with a carbonaceous adsorbent, for example activated carbon, to obtain a mixture, separating the adsorbent from the mixture to obtain a purified liquid extract, and drying the purified liquid extract. A carbonaceous adsorbent is any adsorbent which is comprised of molecules that are made up substantially of carbon atoms and which exhibits adsorbent characteristics like activated carbon.
In another embodiment of the present invention there is provided a process for preparing a Simmondsins extract having improved organoleptic characteristics, for example, reduced odour, bitterness, astringency or pungency, comprising the steps of eluting plant material containing Simmondsins with a polar organic solvent to dissolve the Simmondsins, separating the eluent containing the Simmondsins and the solvent from the plant material to obtain a dilute crude Simmondsins extract, concentrating the crude Simmondsins extract, removing oils from the concentrated crude Simmondsins extract, reacting the concentrated crude Simmondsins extract with a carbonaceous adsorbent to obtain a mixture, separating the adsorbent from the mixture to obtain a purified liquid extract, and drying the purified liquid extract.
In some embodiments, the crude Simmondsins extract may be enriched to increase the total simmondsin content. This may be achieved by extraction with a solvent system of ethanol and ethyl acetate mixture at various ratios.
In an another embodiment, the invention provides a feed containing a Simmondsins extract of the invention.
In alternative embodiments, the purified Simmondsins extract of the invention may be blended into feed as a food intake suppressant.


REFERENCES:
patent: 4148928 (1979-04-01), Sodini et al.
patent: 5672371 (1997-09-01), D'Oosterlynck
patent: 6007823 (1999-12-01), Abbott et al.
patent: 02053896 (1990-02-01), None
Van Boven et al. J. Chrom. B: Biomed. Appl. 1994, vol. 655, pp. 281-285.

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