Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – C-o-group doai
Reexamination Certificate
2003-01-31
2004-01-27
Richter, Johann (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
C-o-group doai
C514S164000, C514S179000, C514S707000, C514S925000, C568S840000, C568S913000, C568S918000, C568S877000, C568S923000, C568S920000
Reexamination Certificate
active
06683116
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates generally to a method for the generation of a composition of matter comprised of a unique profile of primary aliphatic alcohols, having 24 to 30 carbon atoms, from a novel natural source—a wax secreted by the Chinese wax soft scale insect,
Ericerus pela
, which belongs to the family Coccidae. The present invention includes the composition of matter, referred to herein as “polycosanol(s)” produced by the method of the invention. The polycosanol composition produced according to the method of this invention is comprised of primarily four primary aliphatic alcohols, tetracosanol, hexacosanol, octacosanol and triacontanol. The invention also includes the use of this composition of matter for the prevention and treatment of obesity, syndrome X, diabetes, hypercholesterolemia, atherosclerotic complications, ischemia and thrombosis.
BACKGROUND OF THE INVENTION
Polycosanols are a class of primary aliphatic alcohols having 20 to 40 (C20-C40) carbon atoms. They are widely distributed in germs, kernels and other components of nuts, seeds, fruits and cereals (Kawanishi et al. (1991) J. Amer. Oil Chemist Soc. 68:869-872), in Greek olive oils (Dimitrios et al. (1983) Grasas Aceites 34:402-404) and in apple wax (Belding et al. (1993) Hertscience 28:90). Polycosanols are also present, in very small amounts (less than 0.1%), in wheat grain, in the form of the long chain alkyl esters of fatty acids. The major compounds present in wheat grain include, palmitoyl hexacosanol and arachidoyl, palmitoyl and behenoyl tetracosanol (Ohnishi et al. (1986) Cereal Chem 63:193-196).
Polycosanols, both as the free alcohols and the esters of fatty acids, have been isolated from many different genera and species of plants, including from the species
Achillea biebersteinii
(Oskay and Yeslada (1984) J. Nat. Prod. 47:742),
Calamagrostis arundinacea
(Solberg (1976) Acta Chem. Scand Ser. B. Org. Chem. Bioche. 30:786-787),
Emilia sonchifolia
(Srinivasan and Subramanian, (1980) Fitoterapia 51:241-244),
Heliotropium digynum
(Ismail et al. (1984) Fitoterapia 55:110-112),
Hypericum perforatum
(Brondze (1983) J. Nat. Prod. 46:940-941),
Tragopogon orientalis
(Krzaczek et al. (1988) Acta Soc. Bot. Pol. 57:85-92), and from the genera of Triceae (Tulloch (1981) Can. J. Bot. 58:2602-2615). Polycosanols have also been isolated from various parts of many different genera and species of plants, including from the bark of various Acacia species (Banerji and Nigram (1980) J. Indian Chem. Soc. 57:1043-1044); from the stem of
Anisomeles indica
(Dobhal et al. (1988) Fitoterapia 59:155); from the leaves of
Cordia rothii
(Behari et al. (1980) Acta Cienc. Indica Chem. 6:226-228),
Hibiscus cannabinus
(Makhsudova (1979) Chem. Nat. Compd. 15:186) and
Holigarna arnottiana
(Prakash and Banerji (1979) Fitoterapia 50:265-266); from the roots of
Talinum paniculatum
(Komatsu et al. (1982) Yakugaku Zasshi 102:499-502); from the leaves and roots of
Gymnosporia Montana
(Kumar and Srimannarayana (1981) J. Nat. Prod. 44:625-628); from the aerial parts of
Cymbopogon citrates
(Olaniyi et al. (1975) Planta Medica 28:186-189),
E. merifolia
(Baslas and Agarwal (1980) Indian J. Pharm. Sci. 42:66-67) and
E. Peplus
(Rizk et al. (1980) Fitoterapia 51:223-228),
Portulaca suffruticosa L.
(Joshi et al. (1987) Herba Pol. 33:71-74) and
Youngia denticulate
(Arai et al. (1982) J. Pharm. Soc. Jp. 102:1089-1091); and from the heartwood of
Melia birmanica
(Banerji and Nigam, (1981) Fitoterapia 52:3-4). Polycosanols have also been isolated from carnauba wax from exudates of the leaves of the palm tree
Copernicia cerifera
(Pinto and Bento (1986) Rev Soc Bras Med Trop 19:243-5), from the leaf wax of
Eulphorbia helioscopia
(Nazir et al. (1993) Xeischrift fur Naturforschung. Section C Biosciences 48:5-9), from epicuticular waxes of genera of Gramineae (Tulloch (1981) Can. J. Bot. 59:1213-1221), and from and the latex of
Euphorbia pseusocactus
(Awad et al. (1993) Fitoterapia 64:553) and
Euphorbia thymifolia
(Agarwal and Maslas (1981) Indian J. Pharma. Sci. 43:182-183). Finally, polycosanols have been isolated from the Korean indigenous plant
Echinosophora koreensis
(Kang and Kim (1987) Arch Pharmacal Res. 10:67-68).
Bertholet has described a method for preparing polycosanol compositions by means of the saponification of plant wax from rice bran wax, carnauba wax and jojoba oil. (Bertholet, U.S. Pat. No. 5,159,124 (1991)). In the method described by Bertholet, the plant wax was first dissolved in an organic water immiscible solvent, such as butanol or pentanol, and then hydrolyzed using an aqueous solution of an alkaline earth metal hydroxide. The fatty acid by products of the saponification reaction are soluble in the alkaline aqueous layer and the polycosanol alcohol product remains in the organic layer, which contains <10% fatty acids and >90% alcohols. The overall yield of the reaction was approximately 50%. The composition of the polycosanol product is dependent on the origin of the plant wax.
N-hexacosanol has been isolated from wool wax hydrosylate mixtures using gel permeation chromatography (Steel et al. (1999) International Publication No. WO 99/48853).
Polycosanol compositions isolated from rice bran wax have been formulated with phytosterol from vegetable oil and used for reducing cholesterol levels. The aliphatic alcohol profile of this material is approximately 23-33% total polycosanol. Triacontanol is the major compound (8-9%), followed by octacosanol (5-6%) and tetracontanol, hexacosanol, dotriacontanol and tetratriacosanol (2-5% each). (Sorkin Jr. (1999) U.S. Pat. No. 6,197,832, and Sorkin Jr. (1998) U.S. Pat. No. 5,952,393). Octacosanol isolated from Sinach has been formulated with other ingredients as a nutritional powder for boosting energy. (Gaynor U.S. Pat. No. 5,744,187 (1996)).
Sugar cane provides a major natural source of commercial polycosanol products (Ali et al. (1979) Egypt J. Pharm. Sci. 18:93-99). The long chain aliphatic alcohols are located primarily in the wax layer of sugar cane, with octacosanol being the predominant compound (Nagata et al. (1994) Breeding Sci. 44:427-429) (See Table 1, below). Aliphatic alcohols from sugar cane wax can be extracted directly with a supercritical fluid, an organic solvent or an alcohol to obtain a mixture with octacosanol (7-10%) and triacontanol (0.4-1%) as the major components (Inada et al. (1986) U.S. Pat. No. 4,714,791). A mixture of higher primary aliphatic alcohols, having from 24 to 34 carbon atoms has been obtained by saponification of sugar cane wax. (Laguna et al. (1996) U.S. Pat. No. 5,856,316). The saponification reaction described included melting the sugar cane wax, forming a homogeneous phase with an alkaline earth hydroxide (5-30%), extracting with an organic solvent and recrystallizing from an organic solvent. The profile of the material included octacosanol as the major component (60-70% content), followed by triacontanol (10-15%), hexacosanol (5.5-8.5%), dotriacontanol (4-6%), heptacosanol (2-3.5%), tetratriacontanol (0.4-2.0%), nonacontanol (0.4-1.2%) and tetracosanol (0.5-1.0%). This material has been formulated with acetylsalicylic acid and used for the treatment of hypercholesterolemia, atherosclerotic complications, gastric ulcers and to improve male sexual activity. (Laguna et al. (1996) U.S. Pat. No. 5,856,316).
Ericerus pela
, which belongs to the family Coccidae (Ben-Dov and Hodgson, (1997) Soft scale insects; their biology, natural enemies and control. Vol. 7A. Elsevier Science Publishers, Amsterdam), is an insect indigenous to southern China, having the common name white wax scale. (Zhang (1987) Scientia Silvae Sinica 23:383-385, Cen and Ji (1988) Insect Knowledge 25:230-232). This insect has a high economic value in China (Chen (1999) World Forest Res. 12:46-52), due to its ability to produce wax and its high nutritional value (Zhao et al. (2001) Entomological Knowledge 38:216-218). The female lays over 7000 eggs on average (Park et al. (1998) Korea J. Applied Entomology 3
Jia Qi
Zhao Ji-Fu
Price Elvis O.
Richter Johann
Swanson & Bratschun L.L.C.
Unigen Pharmaceuticals, Inc.
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