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(12) Patent Application Publication (10) Pub. No.: US 2013/0303470 A1 Smothers (43) Pub US 2013 0303470A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2013/0303470 A1 Smothers (43) Pub. Date: Nov. 14, 2013 (54) PLANT EXTRACTION METHOD AND Publication Classification COMPOSITIONS (51) Int. Cl. (71) Applicant: Nerium Biotechnology, Inc., San C7H I/08 (2006.01) Antonio, TX (US) A68/60 (2006.01) A613 L/7048 (2006.01) (72) Inventor: Donald L. Smothers, Terrell, TX (US) (52) U.S. Cl. CPC .............. C07H I/08 (2013.01); A61 K3I/7048 (21) Appl. No.: 13/944,720 (2013.01); A61K 8/602 (2013.01) USPC .............................................. 514/26:536/6.3 (22) Filed: Jul. 17, 2013 (57) ABSTRACT Related U.S. Application Data The present invention pertains to methods of extracting car (63) Continuation of application No. 12/578,436, filed on diac systs from arts gy sing play Oct. 13, 2009, now Pat. No. 8524286 material, such as Nerium oteanaer, t rougn use of aloe. It • - s s • L vs. 8 Y-sa-1 is a Y- a • further provides for compositions resulting from Such extrac (60) Provisional application No. 61/105,133, filed on Oct. tions, pharmaceutical compositions, cosmetic compositions, 14, 2008. and methods of treating skin conditions. US 2013/0303470 A1 Nov. 14, 2013 PLANT EXTRACTION METHOD AND bility of the cardiac glycosides to some extent. More recently, COMPOSITIONS U.S. Pat. No. 7,402.325, which is hereby incorporated by reference in its entirety, has described use of supercritical CROSS-REFERENCE TO RELATED CO as extracting higher yields of desired product from pow APPLICATIONS dered oleander leaves. Extraction with supercritical CO 0001. This application is a continuation of U.S. applica necessitates use of high pressure apparatus (above ca. 100 tion Ser. No. 12/578,436, filed Oct. 13, 2009, which claims atmospheres), with all of its attendant hazards. the benefit of U.S. Provisional Application No. 61/105,133, 0007 Accordingly, a need exists for a way to extract ole filed on Oct. 14, 2008. The disclosures of all the above are andrin and other cardiac glycosides more efficiently from incorporated herein by reference in their entireties for all various plant species such as Nerium without use of excessive purposes. heat or high pressure apparatus. SUMMARY OF THE INVENTION FIELD OF THE INVENTION 0008. The present invention provides a method to extract 0002 The present invention pertains to methods of cardiac glycosides from a cardiac glycoside-containing plant extracting materials from biological sources, and particularly species, such as a Nerium species, through use of aloe, such as from plant matter for cosmetic and medicinal applications. that derived from Aloe vera. It further provides compositions resulting from Such extraction. DESCRIPTION OF THE RELATED ART 0009 Specifically, it provides a method of performing an 0003 Biological sources have provided the bases for extraction of plant material derived from a cardiac glycoside medicines and cosmetics from the earliest days of mankind. containing plant species, such as a species from the genus Most such sources have been plants, which initially were used Nerium, comprising agitating the plant material in aloe muci as is. Oftentimes, however, it is desirable to extract materials lage and separating the extract from any remaining Solid from plants, as for example when the desired material con material. stitutes only a small proportion of a given plant, or when the 0010. The extraction method optionally involves heating material occurs in the presence of other, undesirable constitu the solution from about 40°C. to about 100° C., optionally entS. including use of extraction adjuvants such as alcohols, 0004 Glycosides represent an important class of com ketones, and esters. pounds extracted from plant sources. Cardiac glycosides, for 0011. An embodiment provides a method of extracting example, are glycosylated Steroids, i.e., steroids conjugated cardiac glycosides comprising intermixing a cardiac glyco to a carbohydrate moiety. Examples of cardiac glycosides side plant species with aloe under conditions selected to form include those useful in the production of Such drugs as an extraction mixture. digoxin and digitoxin. An important class of glycosides 0012. An embodiment further provides conditioning the comes from the genus Nerium, which includes such species as extraction mixture under conditions selected to extract car Nerium indicum, Nerium odorum, and Nerium Oleander, the diac glycosides from the cardiac glycoside plant species to last being the oleander plant native to Asia and the Mediter form a conditioned extraction mixture, wherein the condi ranean littoral and now found also in parts of the United tioned extraction mixture comprises residual cardiac glyco States. The various Nerium species afford Such glycosides as side plant species and a cardiac glycoside aloe mixture. oleandrin, which finds extensive use in medicine. 0013 An embodiment further provides separating at least 0005 Extraction of cardiac glycosides from Nerium ole a portion of the cardiac glycoside aloe mixture from the ander facilitates their use clinically by allowing administra residual cardiac glycoside plant species to form a cardiac tion of compositions of known potency and purity. Previous glycoside aloe extract, where the cardiac glycoside aloe methods of extracting these glycosides have employed hot extract comprises cardiac glycosides extracted from a cardiac water, as described in U.S. Pat. No. 5,135,745 and U.S. Pat. glycoside plant species, and where the cardiac glycoside aloe No. 6,565,897, as well as U.S. Patent Publication No. extract is Substantially free of the residual cardiac glycoside 20060188585, each of which is hereby incorporated by ref plant species. erence in its entirety. Owing to the large lipophilic steroidal 0014. In some embodiments the cardiac glycoside plant moiety, however, oleandrin has poor aqueous solubility, species belongs to a family selected from Apocynaceae, Bras which limits the effectiveness of aqueous extraction. Further sicaceae, Plantaginaceae, Ruscaceae, or Hyacinthaceae. more, plants generally have waxy cuticles Surrounding their 0015. In some embodiments the cardiac glycoside plant exterior Surfaces to minimize desiccation. This waxy cuticle belongs to the species Nerium indicuin or Nerium Oleander: not only limits the egress of water from the plant to the 0016. In some embodiments the conditioning comprises exterior, but also the ingress of water from the exterior into the heating the extraction mixture to a temperature in the range of plant, and thus further impedes efficientaqueous extraction of about 40°C. to about 100° C. to form the conditioned extrac the desired cardiac glycosides. Also, the desired cardiac gly tion mixture. cosides can hydrolyze or otherwise decompose on long expo 0017. In some embodiments the conditioning comprises sure to hot water. heating the extraction mixture for a heating time in the range 0006. One solution to these problems has been to perform of about 1 to about 10 hours. the extraction not with pure water, but with a mixture of water 0018. In some embodiments the separating comprises and a water-miscible alcohol. Such as methanol or ethanol, as Subjecting the conditioned extraction mixture to a separation described in U.S. Patent Publication No., 20070154573, method selected from the group consisting of filtration, cen which is hereby incorporated by reference in its entirety. Use trifugation, and decanting. of aqueous alcohol increases both the penetration of the 0019. In some embodiments the extraction mixture com extraction solvent into the interior of the plant and the solu prises an amount of the cardiac glycoside plant species in the US 2013/0303470 A1 Nov. 14, 2013 range of about one part to about 50 parts by weight and an 0033. In some embodiments, the extraction mixture com amount of the aloe in the range of about one part to about 100 prises an amount of cardiac glycoside plant species in the parts by weight, based on the total weight of extraction mix range of about one part to about 50 parts by weight and an ture. amount of aloe in the range of about one part to about 100 0020. In some embodiments the extraction mixture com parts by weight, based on total weight of the extraction mix prises an adjuvant selected from the group consisting of alco ture. hols, ketones, and esters. 0034. An embodiment further provides conditioning the 0021. An embodiment provides a cardiac glycoside aloe extraction mixture under conditions selected to extract car composition, comprising aloe and at least one cardiac glyco diac glycosides from cardiac glycoside plant species to form side. a conditioned extraction mixture, wherein the conditioned 0022. In some embodiments, the cardiac glycoside is a extraction mixture comprises residual cardiac glycoside plant cardiac glycoside aloe extract from a cardiac glycoside plant species and a cardiac glycoside aloe mixture. species. 0035 Examples of conditioning the extraction mixture 0023. In some embodiments, the cardiac glycoside aloe composition is a cardiac glycoside aloe extract wherein the under conditions selected to extract cardiac glycosides from cardiac glycoside plant species is Nerium Oleander: cardiac glycoside plant species, include heating the extraction 0024. An embodiment provides pharmaceutical composi mixture, agitating the extraction mixture, and heating the tions comprising aloe, at least one cardiac glycoside and a extraction mixture with agitation. pharmaceutically acceptable carrier. Another embodiment 0036. In some
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