Drug – bio-affecting and body treating compositions – Antigen – epitope – or other immunospecific immunoeffector – Conjugate or complex
Reexamination Certificate
2000-05-24
2002-02-26
Owens, A (Department: 1625)
Drug, bio-affecting and body treating compositions
Antigen, epitope, or other immunospecific immunoeffector
Conjugate or complex
C549S407000, C549S408000
Reexamination Certificate
active
06350453
ABSTRACT:
BACKGROUND OF THE INVENTION
Tocotrienols generally are classified as farsnesylated chromanols (FC) and mixed terpenoids. Tocopherol and tocotrienol are believed to have beneficial effects because they act as antioxidants. Tocotrienols, in particular, have been documented to possess hypocholesterolemic effects as well as an ability to reduce atherogenic apolipoprotein B and lipoprotein plasma levels. Further, tocotrienols are believed to be useful in the treatment of cardiovascular disease and cancer. See, for example, Theriault, A., et al., “Tocotrienol: A Review of its Therapeutic Potential,”
Clinical Biochemistry
, 32:309-319 (July 1999); and “Tocotrienols: Biological and Health Effects,” in
Antioxidant Status, Diet, Nutrition, and Health
, Pappas, ed. (CRC Press), pp. 479-496 (1999). &dgr;-tocotrienol and &ggr;-tocotrienol, in particular, have been identified as effective suppressants of cholesterol activity, Qureshi, et al., “Response of Hypercholesterolemic Subjects to Administration of Tocotrienols,”
Lipids
, 30(12) (1995), and in inducing apoptosis of breast cancer cells, Yu, et al., “Induction of Apoptosis in Human Breast Cancer Cells by Tocopherols and Tocotrienols,”
Nutrition and Cancer
, 33(1):26-32 (1999).
Tocols, which includes tocopherols and tocotrienols, have several sources, including several vegetable oils, such as rice bran, soybean, sesame and palm oils. Tocotrienols have been discovered in the seeds of
Bixa orellana Linn
, otherwise known as the achiote tree. See, Jondiko, I.S., et al., “Terpenoids and an Apocarotenoid from Seeds of
Bixa Orellana,” Phytochemistry
, 28(11):3159-3162 (1989). However, each source of tocotrienols and tocopherols generally contains more than a single tocol homolog. For example, palm oil and rice bran oil generally include both tocotrienols and tocopherols. Further, &agr;-tocopherol has been reported to attenuate certain effects of tocotrienols, such as the cholesterol-suppressive activity of &ggr;-tocotrienol. See, for example, Qureshi, et al., supra. In addition, because of their structural similarity, tocotrienols and tocopherols can be difficult to separate.
Geranylgeraniol includes acyclic diterpene alcohols (ADA) and geranylgeraniated terpenoids (GGT), and occurs naturally in linseed oil and cedrela toona wood and tomato fruit. Geranylgeraniol also has been discovered to exist in the seeds of
Bixa orellana
. See Craveiro, et al., “The Presence of Geranylgeraniol in
Bixa Orellana Linn,” Quimica Nova
, 12(3):297-298 (1989). Potential uses for geranylgeraniol include synthesis of co-enzyme Q
10
, vitamin K and tocotrienols. It is believed to inhibit esterification of retinol into inactive retinyl esters and, therefore, may be used to improve skin desquamation and epidermal differentiation. See U.S. Pat. No. 5,756,109, issued to Burger, et al. on May 26, 1998. Geranylgeraniol has been employed in conjunction with HMG-CoA reductase inhibitors in treatment of elevated blood cholesterol. See WO 99/66929 by Scolnick, published Dec. 29, 1999. Geranylgeraniol also is suspected to be useful for treatment of human prostate cancer. See U.S. Pat. No. 5,602,184, issued to Myers, et al. on Feb. 11, 1997. As with isolation of specific tocotrienols, geranylgeraniol must be separated from terpenoid compounds having similar structures when derived from natural sources. Separation of geranylgeraniol from these related compounds can be difficult.
Therefore, a need exists to find a method for recovery of &dgr;- and &ggr;-tocotrienols, and of geranylgeraniol, that minimizes or overcomes the above-referenced problems.
SUMMARY OF THE INVENTION
A source of material known as a byproduct solution of
Bixa orellana
seed components, which is obtained as an oily material after removing the bulk of annatto color, is removed from either the aqueous extract or solvent extract of annatto seeds. Further, this byproduct contains a tocotrienol component and a geranylgeraniol component and can be used as a source for the recovery of a tocotrienol component and a geranylgeraniol component.
The present invention generally is directed to a method of forming a tocotrienol composition.
The method includes volatilizing solvent from a byproduct solution of
Bixa orellana
seed components to form thereby a tocotrienol composition.
In one embodiment, the method further includes the step of distilling a geranylgeraniol component of the tocotrienol composition. At least a portion of the geranylgeraniol component is separated thereby from the tocotrienol composition to form a geranylgeraniol distillate.
In another embodiment, the method of forming a tocotrienol composition includes extracting at least a portion of an annatto component from
Bixa orellana
seeds, whereby an aqueous fraction is formed. The aqueous fraction includes the annatto component, a tocotrienol component and a geranylgeraniol component. The annatto component is precipitated from the aqueous fraction to form an annatto precipitate and a byproduct solution of
Bixa orellana
seed components. Water then is volatilized from the byproduct solution of
Bixa orellana
seed components to form the tocotrienol composition.
In still another embodiment, the method includes distilling tocotrienol components of the tocotrienol composition to form a tocotrienol distillate.
The present invention has many advantages. For example, the amount of &dgr;-tocotrienol present in the byproduct solution of
Bixa orellana
seed components employed by the method is very high (500-700 times higher) relative to that found in other common sources, such as palm oil or rice bran oil. Further, and also in contrast to palm and rice bran oils, there is essentially no &agr;-tocopherol present in the byproduct solution of
Bixa orellana
seed components employed by the method of the present invention. Therefore, the tocotrienol composition formed and, optionally, the tocotrienol distillate formed, generally does not require separation of &dgr;-tocotrienol from &agr;-tocopherol which, as discussed above, can have a mitigating effect on the therapeutic properties of &dgr;-tocotrienol. Further, the byproduct solution of
Bixa orellana
seed components is a convenient source of geranylgeraniol. Therefore, relatively high concentrations of geranylgeraniol also can be obtained by the method of the invention.
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Pearce, B. C., et al., “Hypocholesterolemic Activity of Synthetic and Natural Tocotrienols,”J. Med. Chem., 35(20):3595-606 (Oct. 2, 1992).
Jondiko, I. J. O. and Pattenden, G., “Terpenoids and an Apocarotenoid from Seeds ofBixa Orellana,” Phytochemistry, 28(11):3159-3162 (1989).
“Amazing Grain, How Sweet It Is,”Harvard Health Letter, pp. 6-7 (Mar. 1997).
Theriault, A., et al., “Tocotrienol: A Review of Its Therapeutic Potential,”Clinical Biochemistry, 32(5):309-319 (1999).
Yu, W., et al., “Induction of Apoptosis in Human Breast Cancer Cells by Tocopherols and Tocotrienols,”Nutrition and Cancer, 33(1):26-32 (1999).
He, L., et al., “Isoprenoids Suppress the Growth of Murine B16 melanomas In Vitro and In Vivo,”American Society for Nutritio
Foley John
Tan Barrie
American River Nutrition, Inc.
Hamilton Brook Smith & Reynolds P.C.
Owens A
LandOfFree
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