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WO 2009/060024 Al (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43)eI.nternational Publication Date PCT (10) International Publication Number 14 May 2009 (14.05.2009) WO 2009/060024 Al (51) International Patent Classification: (74) Agents: SCHREIBER, Christoph et al.; P.O. Box 10 22 A61K 36/33 (2006.01) A61P 3/00 (2006.01) 41, 50462 Cologne (DE). A61P 1/04 (2006.01) (81) Designated States (unless otherwise indicated, for every (21) International Application Number: kind of national protection available): AE, AG, AL, AM, PCT/EP2008/065048 AO, AT,AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, (22) International Filing Date: EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, 6 November 2008 (06.1 1.2008) IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, (25) Filing Language: English LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, (26) Publication Language: English MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TJ, (30) Priority Data: TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, 07120081.0 6 November 2007 (06. 11.2007) EP ZW 61/002,058 6 November 2007 (06. 11.2007) US (84) Designated States (unless otherwise indicated, for every (71) Applicant (for all designated States except US): FINZEL- kind of regional protection available): ARIPO (BW, GH, BERG GMBH & CO. KG [DE/DE]; Koblenzer Str. GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, 48-54, 56626 Andernach (DE). ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), (72) Inventors; and European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, (75) Inventors/Applicants (for US only): PISCHEL, Ivo FR, GB, GR, HR, HU, IE, IS, IT, LT,LU, LV,MC, MT, NL, [DE/DE]; Lacher Weg 1, 53547 Rossbach (DE). FEIS- NO, PL, PT, RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, TEL, Bjδrn [DE/DE]; Im Boden 32, 56626 Andernach CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). (DE). WALBROEL, Bernd [DE/DE]; Flurgasse 48, Published: 53639 Konigswinter (DE). — with international search report [Continued on next page] (54) Title: EXTRACT FORMULATION OF OPUNTIA FICUS INDICA In vivo oral glucose tolerance test (n=6) -20 20 40 60 80 100 120 140 Time (min) Fig. 1 (57) Abstract: A process for the preparation of an opuntia extract formulation, comprising the steps of: a) - extracting plant parts selected from fruit, fruit parts, and mixtures thereof using an extractant containing water and from 0 to 70% by weight of alcohols; - at least partially removing the extractant; b) - extracting plant parts selected from cladodes, cladode parts and mixtures thereof using an extractant containing water and from 0 to 70% by weight of alcohols; - at least partially removing the extractant; c) - mixing together the extracts of step a) and b). before the expiration of the time limit for amending the claims and to be republished in the event of receipt of amendments Extract formulation of Opuntia ficus indica This invention relates t o cactus pear extract formulations, methods for their manufacture and their use. Cactus pear extract formulations have a positive effect on blood glucose levels and can be used for the treatment and preven- tion of diabetes mellitus II. The cactus pear (Opuntia spp., Opuntia ficus indica) has for centuries been used in traditional medicine in the New World, in South, Central and North America, and also in the countries of the Mediterranean, North Africa and other areas for treating illnesses, for alleviating symptoms and for preventing metabolic disorders. Stintzing FC and Carle R (Cactus stems (Opuntia spp.) A review on their chemistry, technology, and uses. MoI. Nutr. Food Res. 2005, 49, 175-194) describe a range of uses of cactus stems (cladodes), including anti-oxidant, anti-inflammatory (including in ulcers), analgesic, hypoglycaemic, anti-diabetic and blood lipid and cholesterol lowering effects. Due t o the pigmented betalain derivatives they contain, cactus pears, the edible fruit of Opuntia species, have been described as having uses as foodstuffs, in particular as food colour ing concentrates, and as therapeutic remedies. A review by Livrea MA and Tesoriere L (Health Benefit and Bioactive Components of the Fruits from Opun- tia ficus-indica. J. PACD 2006, 73-90) showed, in particular in the use of the edible parts of the fruit and fruit juice, anti-oxidant activity, cardio-protective, anti-ulcer and hepato-protective effects, as well as a protective effect on nerv ous tissue and cancer prophylaxis. Antioxidant betalain derivatives with free radical scavenging properties are cited as the bioactive substances. Traditional use of Opuntia in type 2 diabetes mellitus is limited t o the use of fresh cladodes (young cactus shoots), which are generally boiled, fried or grilled and eaten in quantities of up t o 500 grams (Frati AC, Xilotl Diaz N, Altamirano P, Ariza R, Lόpez-Ledesma R.; The effect of two sequential doses of Opuntia streptacantha upon glycemia. Arch Invest Med (Mex.), 1991, 333- 6). In 1933 Gruwell CE and Preene HE described an antidiabetic activity for an extract of fleshy branches of Opuntia phaeacantha (US 2,082,952). Neither active components nor purification steps had been mentioned. They disclosed the use of intense solar radiated plants as a need for effective and active products. Even in relatively high dosages, dried, powdered cladodes in pharmaceutical forms of administration such as tablets and capsules have a blood lipid reduc- ing effect only and are marketed solely for this purpose (www.neopuntia.com). Undefined cladode extracts produced using organic solvents have been de scribed in the literature as having a hypoglycaemic effect. (Trejo-Gonzalez A et al. A purified extract from prickly pear cactus (Opuntia fuliginosa) controls experimentally induced diabetes in rats. Journal of Ethnopharmacology, 1996, 27-33.) Galati EM et al. (Opuntia ficus indica (L.) Mill mucilages show cytoprotective effect on gastric mucosa in rat), Phytotherapy Research 2! (2007), 344-346 described an aqueous extraction of fresh cladodes, followed by a reprecipitation of the extract in ethanol to receive a small pectin-fraction and a mucilage fraction (each about 10%). A gastroprotective effect of the mucilage extract is described. No relation to a glucose- or lipid-metabolic activity is described. Other than the applications described above, the literature, including patent literature, describes the use of plant extracts from cladodes of prickly pears for alcohol-induced hangovers (KR 2004-0094173), as a neuroprotective agent (KR 2003-0035974), as an immune stimulant (KR 2002-0092021), for derma- tological problems (JP 2002-0072130; KR 2003-0023398) and as a microbi- cide (US 3,860,710; KR 2003-0023398). The fruits (cactus pears) are ex tracted and concentrated to obtain food colourings (betalain, etc.) (KR 2003- 0035974; Moβhammer MR, Stintzing FC, Carle R. Cactus Pear Fruits (Opuntia spp.) : A Review of Processing Technologies and Current Uses. 2006, J. PACD, 1-25). DE 103 50 194 discloses the plant's flowers as an extracted plant component which is neither cladode nor fruit. The ethanolic flower extract is reputed t o be neuroprotective. Wolfram RM et al. (Effect of prickly pear (Opuntia robusta) on glucose- and lipid-metabolism in non-diabetics with hyperlipidemia - A pilot study), Wiener klinische Wochenschrift 114 (2002), 804-846 describe pectin as the mode of action of metabolic activity from fruit pulp and stated an insulin-lowering side- effect after administration of about 25Og fruits per day. No synergistic anti-diabetic or hypoglycaemic activity has previously been ascribed t o any combination of fruits, fruit juice or fruit components with clad- odes or any extracts thereof. The object and purpose of the present invention is t o reproducibly manufac ture cactus pear extract preparations with improved characteristics, in part icu lar an increased hypoglycaemic effect. Further, it makes use of novel, inexpensive plant components which are read ily available and thus previously unused raw materials. Surprisingly, it was found that this object can be achieved using a method for manufacturing cactus pear extract preparation encompassing the steps a) - extracting plant parts selected from fruit, fruit parts, and mixtures thereof using an extractant containing water and from 0 t o 70% by weight of alcohols; - at least partially removing the extractant; b) - extracting plant parts selected from cladodes, cladode parts and m ix tures thereof using an extractant containing water and from 0 to 70% by weight of alcohols; at least partially removing the extractant; c) - mixing together the extracts of step a) and b). The fruits, fruit parts, cladodes and cladodes parts are plant parts from Opun- tia. I n one embodiment the method encompasses 1 . extraction from raw materials a) fresh or dried fruit skin (pomace or fruit residue following juice extraction) and/or fresh or dried cladodes or the resi due of same following pressing, b) mixing the raw material with a hydroalco- holic extraction medium in order t o obtain a raw extract, where the hydroalco- holic extraction medium contains 0 t o 70% vol alcohol; 2 . at least partial removal of the alcoholic component of the raw extract in order t o obtain a concentrated, primarily aqueous or almost water-free thick extract; The extract preparation obtained may be processed : a) immediately for the manufacture of liquid formulations (syrups, drops, drinks); b) for filling soft gelatine capsules or c) with or without carriers t o dried extracts.
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