WO2008046521A1 - Préparation à usage oral (ii) - Google Patents
Préparation à usage oral (ii) Download PDFInfo
- Publication number
- WO2008046521A1 WO2008046521A1 PCT/EP2007/008596 EP2007008596W WO2008046521A1 WO 2008046521 A1 WO2008046521 A1 WO 2008046521A1 EP 2007008596 W EP2007008596 W EP 2007008596W WO 2008046521 A1 WO2008046521 A1 WO 2008046521A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- esters
- extracts
- contain
- preparations according
- sterols
- Prior art date
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- 239000003755 preservative agent Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
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- 229920002414 procyanidin Polymers 0.000 description 1
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- OXGUCUVFOIWWQJ-HQBVPOQASA-N quercitrin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OXGUCUVFOIWWQJ-HQBVPOQASA-N 0.000 description 1
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- 238000011084 recovery Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- IKGXIBQEEMLURG-NVPNHPEKSA-N rutin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-NVPNHPEKSA-N 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- CZDNLUMNELLDDD-JAIJEDJZSA-N salicortin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1COC(=O)[C@@]1(O)C(=O)CCC=C1 CZDNLUMNELLDDD-JAIJEDJZSA-N 0.000 description 1
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- 150000003873 salicylate salts Chemical class 0.000 description 1
- YHBIHSCTXBGAIK-UHFFFAOYSA-N salicyloylsalicylin Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=CC=C1COC(=O)C1=CC=CC=C1O YHBIHSCTXBGAIK-UHFFFAOYSA-N 0.000 description 1
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- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- NIABBGMPPWXWOJ-UHFFFAOYSA-N schaftoside Natural products OC1C(O)C(O)C(CO)OC1OC1=C(O)C(OC2C(C(O)C(O)CO2)O)=C(OC(=CC2=O)C=3C=CC(O)=CC=3)C2=C1O NIABBGMPPWXWOJ-UHFFFAOYSA-N 0.000 description 1
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- 239000011669 selenium Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
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- 229940032094 squalane Drugs 0.000 description 1
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- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 229940094908 stearyl myristate Drugs 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 1
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- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
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- 235000013616 tea Nutrition 0.000 description 1
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- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- HBPNTDBLHQHPLH-UHFFFAOYSA-N tetradecyl 16-methylheptadecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C HBPNTDBLHQHPLH-UHFFFAOYSA-N 0.000 description 1
- AVKVDDQTHIQFSC-UHFFFAOYSA-N tetradecyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC AVKVDDQTHIQFSC-UHFFFAOYSA-N 0.000 description 1
- DHZWALZKPWZSMA-UHFFFAOYSA-N tetradecyl oleate Natural products CCCCCCCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC DHZWALZKPWZSMA-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
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- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid group Chemical group C(\C(\C)=C\C)(=O)O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- AQWHMKSIVLSRNY-UHFFFAOYSA-N trans-Octadec-5-ensaeure Natural products CCCCCCCCCCCCC=CCCCC(O)=O AQWHMKSIVLSRNY-UHFFFAOYSA-N 0.000 description 1
- UOGHEBWTVNXYEN-UHFFFAOYSA-N tremulacin Natural products OCC1OC(Oc2ccccc2COC(=O)C3(O)CC(=O)CC=C3)C(OC(=O)c4ccccc4)C(O)C1O UOGHEBWTVNXYEN-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- CSNXTSWTBUEIJB-UHFFFAOYSA-N vicenin-II Natural products OC1C(O)C(O)C(CO)OC1OC1=C(O)C(OC2C(C(O)C(O)C(CO)O2)O)=C(OC(=CC2=O)C=3C=CC(O)=CC=3)C2=C1O CSNXTSWTBUEIJB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/27—Asclepiadaceae (Milkweed family), e.g. hoya
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
- A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
- A61K31/585—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin containing lactone rings, e.g. oxandrolone, bufalin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the invention is in the field of nutritional supplements and relates to new preparations for oral intake containing specific sterols or sterol esters together with Hoodia extracts.
- Hypocholesterolemic agents are understood to mean agents which lead to a reduction of the cholesterol content in the serum of warm-blooded animals, without this resulting in an inhibition or reduction of the formation of cholesterol in the blood.
- Peterson et al. in J. Nutrit. 50, 191 (1953) Phytostenols, so vegetable stenols, and their esters with fatty acids proposed.
- the patents US Pat. No. 3,089,939, US Pat. No. 3,203,862 and German Laid-Open Application DE-OS 2035069 (Procter & Gamble) also point in the same direction.
- the active ingredients are usually added to cooking or edible oils and then absorbed through the diet, but the amounts used are usually low and usually below 0.5 wt .-%, to prevent the edible oils cloud or stenols when added to be precipitated by water.
- storage-stable emulsions of styrene esters in sugar or polyglycerol esters are proposed in European Patent Application EP 0289636 A1 (Ashai).
- sitostanol esters for reducing the blood cholesterol content in margarine, butter, mayonnaise, salad dressings and the like is proposed in European Patent EP 0594612 Bl (Raision).
- the object of the present invention has therefore been to provide new preparations for oral intake, which allow to reduce the concentration of undesired cholesterol in the blood faster with equal amounts of active ingredient or to achieve a corresponding effect with a reduced amount of active ingredient.
- the invention relates to preparations for oral administration, containing
- Sterols - sometimes referred to as sterols - are steroids characterized by a single hydroxyl group in the C3 position. Furthermore, sterols, which usually have from 27 to 30 carbon atoms, may also have a double bond, which is preferably in the 5/6 position. The hydrogenation of this double bond - also called hardening - leads to special sterols, which are referred to as conditions.
- the following figure shows the structure of the most prominent member of the group of sterols, cholesterol, which belongs to the group of zoosterols.
- plant sterols Due to their superior physiological properties, plant sterols, the so-called phytosterols such as ergosterol, stigmasterol and especially sitosterol and its hydrogenation product sitostanol are the preferred types of sterols.
- their esters can also be used with saturated and / or unsaturated fatty acids in which the acyl radicals can then have 6 to 22 carbon atoms and 0 or 1 to 6 double bonds.
- Typical examples are the esters of ⁇ -sitosterol or ⁇ -sitostanol with caproic, caprylic, 2-ethylhexanoic, capric, lauric, isotridecanoic, myristic, palmitic, palmitic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, linolenic Arachin acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures, eg occur in the pressure splitting of natural fats and oils, in the reduction of aldehydes from the Roelen oxosynthesis or the dimerization of unsaturated fatty acids.
- CLA conjugated linoleic acid
- Hoodia specifically Hoodia gordonü
- Hoodia gordonü is a cactus plant native to South Africa that has long been known to the indigenous people as a means to combat hunger. It is reported that in earlier times Bushmen on their hunting expeditions were practically out of food for several weeks only by chewing Hoodia roots. In recent years it has been found that the amazing properties of this plant are related to its high content of specific active steroid glycosides. In 2001/2002, it was possible for the first time to isolate and characterize one of these species; it has since been referred to in the literature as substance P57:
- the oral preparations may contain as optional component (c) further plant extracts which have advantageous physiological properties.
- these are selected from the group formed by Ginkgo biloba, Camellia sinensis, Oleacea europensis, Glycyrhiza glabra, Vaccinium myrtulus, Trifolium pratense, Litchi sinensis, Vitis vinifera, Brasica oleracea, Punica granatum, Petroselinium crispum, Centella asiatica, Passiflora incarnata, Medicago sativa, Valeriana officinalis, Castanea sativa, Salix alba and Hapagophytum procumbens.
- the active ingredients of the extracts obtained from the leaves of the ginkgo tree are flavonoid glycosides which include (iso) quercitin glycosides, kaempferol, kaempferol-3 rhamnoside, isorhamnetin, luteoline glycosides, siterolactyl glycosides, and especially hexacyclic Terpene lactones, the so-called ginkgolides A, B, C, J, M and bilobalides.
- the leaves of green tea contain a variety of substances, such as e.g. Polysaccharides, volatile oils, vitamins, minerals, purines and in addition to alkaloids, such as caffeine, in particular polyphenols, which are usually catechins and flavonoids and are also referred to as "tea tannins”.
- substances such as e.g. Polysaccharides, volatile oils, vitamins, minerals, purines and in addition to alkaloids, such as caffeine, in particular polyphenols, which are usually catechins and flavonoids and are also referred to as "tea tannins”.
- the main constituent of the leaves of the olive tree ⁇ Oleacea europensis is the antioxidant oleuropein, which is also the main source of hydroxytyrosol.
- the main constituent of the extract of the sweet root Glyzyrrhiza glabra is glycyrrhetinic acid.
- Extracts of the common blueberry ⁇ Vaccinium myrtillus contain a mixture of at least 15 different anthocyanosides, such as the following:
- the extracts contain from 20 to 25% by weight of anthocyanosides, from 5 to 10% by weight of tannins and small amounts of various alkaloids, e.g. Myrtin and epimyrtin,
- Phenolic acids and glycosides of quercitrin, isoquercitrin and hyperoside are listed.
- the main constituents of the extracts of the red clover ⁇ Trifolium pratense are isoflavones, such as e.g. Daidzein, genestein, formononentin and biochanin A, as well as their glucosides, e.g. Ononine or sissostrine:
- Extracts derived from the shells of the Litchi fruit have high levels of flavone derivatives, e.g. 2-phenyl-4H-1-benzopyrans, flavanes, flavan-3-ols (catechins, catechol oligomers), flavan-3,4-diols (leucoanthocyanides), flavones, flavonols and flavonones.
- the main component is made up of condensed tannins, so-called procyanodols (OPC).
- PPC procyanodols
- Procyanidin, proanthocyanin, procyanidols, oligoprocyanidine, leucoanthocyanidin, leucodelphinin, leucocyanine and anthocyanogen preferably proanthocyanidin A2 (OPC A2) behave like vitamin P, especially with regard to the inhibition of matrix metalloproteinases.
- Extracts of leaves, roots and in particular grapevines are polyphenols of the OPC type described above.
- the main constituents of cauliflower extracts are amino acids, in particular methionine and cysteine, and glucosinolates, e.g. Glucoraphaine.
- pomegranate (Punica granatum) are found in addition to sugars and citric acid in particular delphinidin-l, 2-glycosides and their aglycones.
- the main constituent of the parsley fat oil (Petroselinium crispum) is the petroselinic acid.
- the extracts show high levels of apiol (l-allyl-2,5-dimethoxy-3,4- (methylenedioxy) benzene,), as well as apiin, myristicin, pinene and selenium.
- the main constituents of the extracts of Centella asiatica are highly condensed naphthenic acids, especially asiatic acid, madecassic acid and their glycosides.
- Extracts of passion fruit ⁇ Passiflora incarnata) are rich in flavones of the type of apigenin and luteolin and their C-glycosides.
- Extracts of alfalfa are rich in isoflavones, e.g. Daidzein, genestein, formononetin, biochanin A and tricine:
- the main constituents of extracts of Valeriana officinalis are valeric acid, valerianone and borneol esters.
- Horse chestnut extracts (Castanea sativa) contain mainly saponins and escin, which is the mixture of two glycosides whose aglycones are derived from proteoscenin, while the sugars are either glucuronic acid or two molecules of D-glucose.
- the two glycosides differ in the nature of the acyl groups in the C22 position.
- R tiglic acid or angelic acid
- beta-escin is an amorphous powder which melts at 225-227 0 C is readily soluble in water
- beta-escin which is also referred to as Flogencyl
- the main constituents of the Salix alba extracts are phenol glycosides and, in particular, salicylates, such as, for example, Salicin, salicortin and tremulacin:
- the main constituents of Devil's Claw Extracts are iridoid glucosides, harpagosides, harpagids and procumbides.
- glycosylated phytosterols e.g., ⁇ -sitosterol
- flavonoids e.g., kaempferol, luteolin
- phenolic acids e.g., phenolic acids
- glycosidic phenylpropanoic acid esters e.g., verbacosides, isoactosides.
- the preparation of the stearic glycoside-containing Hoodia extracts can be carried out in a manner known per se, ie, for example, by aqueous, alcoholic or aqueous-alcoholic extraction of the plants or plant parts or of the leaves or fruits. Suitable are all conventional extraction methods such as maceration, remaering, digestion, agitation, vortex extraction, ultrasound extraction, countercurrent extraction, percolation, repercolation, evacuation (extraction under reduced pressure), diaclation or solid-liquid extraction under continuous reflux. For the industrial use advantageous is the percolation method. As a starting material, fresh plants or plant parts can be used, but usually is based on dried plants and / or plant parts, which can be mechanically comminuted prior to extraction.
- solvents for carrying out the extractions may be organic solvents, water (preferably hot water at a temperature of about 80 ° C and especially of above 95 ° C) or mixtures of organic solvents and water, in particular low molecular weight alcohols with more or less high Water contents, to be used.
- solvents for carrying out the extractions may be organic solvents, water (preferably hot water at a temperature of about 80 ° C and especially of above 95 ° C) or mixtures of organic solvents and water, in particular low molecular weight alcohols with more or less high Water contents, to be used.
- Particularly preferred is the extraction with methanol, ethanol, pentane, hexane, heptane, acetone, propylene glycols, polyethylene glycols and ethyl acetate and mixtures thereof and their aqueous mixtures.
- the extraction is generally carried out at 20 to 100 0 C, preferably at 30 to 90 0 C, in particular at 60 to 80 0 C.
- the extraction is carried out under an inert gas atmosphere to avoid the oxidation of the active ingredients of the extract. This is particularly important for extractions at temperatures above 40 0 C is important.
- the extraction times are set by the skilled person depending on the starting material, the extraction method, the extraction temperature, the ratio of solvent to raw material and others.
- the resulting crude extracts may optionally be subjected to further conventional steps such as purification, concentration and / or decolorization. If desired, the extracts so prepared may be subjected to, for example, selective separation of individual undesired ingredients.
- the extraction can be done to any degree of extraction, but is usually done to exhaustion.
- the present invention encompasses the finding that the extraction conditions and the yields of the final extracts can be selected by the person skilled in the art according to the desired field of use.
- the extracts can also serve as starting materials for the recovery of the above-mentioned pure active ingredients, as long as they can not be synthesized more easily and inexpensively. Accordingly, the active ingredient content in the extracts may be 5 to 100, preferably 50 to 95 wt .-%.
- the extracts themselves may be present as aqueous and / or dissolved in organic solvents preparations and as spray- or freeze-dried, anhydrous solids.
- Suitable organic solvents in this context include, for example, the aliphatic alcohols having 1 to 6 carbon atoms (eg ethanol), ketones (eg acetone), halogenated hydrocarbons (eg chloroform or methylene chloride), lower esters or polyols (eg glycerol or glycols).
- aliphatic alcohols having 1 to 6 carbon atoms eg ethanol
- ketones eg acetone
- halogenated hydrocarbons eg chloroform or methylene chloride
- lower esters or polyols eg glycerol or glycols
- the components (a) and (b) are preferably used in a weight ratio of 99: 1 to 80:20, special synergistic effects being observed in the range from 98: 2 to 85:15 and in particular 95: 5 to 90:10.
- the optional plant extracts of component (c) may constitute from 1 to 25, preferably from 5 to 20 and especially from 8 to 12,% by weight.
- the oral preparations are used in encapsulated form-for example in the form of conventional gelatin macrocapsules-but preferably in microencapsulated form.
- a typical gelatin capsule may contain, for daily ingestion, 3 g CLA and 150 mg hoodia extract.
- microcapsule is understood by those skilled spherical aggregates having a diameter in the range of about 0.0001 to about 5 mm, containing at least one solid or liquid core, which is enclosed by at least one continuous shell. More specifically, it is finely dispersed liquid or solid phases coated with film-forming polymers, in the preparation of which the polymers precipitate on the material to be enveloped after emulsification and coacervation or interfacial polymerization.
- molten waxes are taken up in a matrix ("microsponge") which, as microparticles, can additionally be enveloped by film-forming polymers.
- microscopically small capsules also called nanocapsules, can be dried like powders.
- Alongside mononuclear microcapsules are also multinuclear aggregates Also known as microspheres, which contain two or more cores distributed in the continuous shell material, mononuclear or multinucleated microcapsules may also be enclosed by an additional second, third, etc.
- Shell materials are, for example, gum arabic, agar-agar, agarose, maltodextrins, alginic acid or its salts, for example sodium or calcium alginate, fats and fatty acids, cetyl alcohol, collagen, chitosan, lecithins, gelatin, albumin, shellac, polysaccharides, such as starch or dextran , Polypeptides, protein hy drolysate, sucrose and waxes.
- Semisynthetic shell materials include chemically modified celluloses, especially cellulose esters and ethers, e.g.
- Synthetic envelope materials are, for example, polymers such as polyacrylates, polyamides, polyvinyl alcohol or polyvinylpyrrolidone.
- microcapsules of the prior art are the following commercial products (in each case the shell material is indicated in brackets): Hallcrest microcapsules (gelatine, gum arabic), Coletica thalaspheres (marine collagen), Lipotec millicapsules (alginic acid, agar-agar), induchem Unispheres (Lactose, microcrystalline cellulose, hydroxypropyl methylcellulose); Unicerin C30 (lactose, microcrystalline cellulose, hydroxypropyl methylcellulose), Kobo Glycospheres (modified starch, fatty acid esters, phospholipids), Softspheres (modified agar agar) and Kuhs Probiol Nanospheres (phospholipids) as well as Primaspheres and Primasponges (chitosan, alginates) and Primasys (phospholipids).
- Chitosan microcapsules and processes for their preparation are the subject of prior patent applications by the Applicant [WO 01/01926, WO 01/01927, WO 01/01928, WO 01/01929].
- Microcapsules with average diameters in the range of 0.0001 to 5, preferably 0.001 to 0.5 and in particular 0.005 to 0.1 mm, consisting of an enveloping membrane and a matrix containing the active ingredients can be obtained, for example, by
- the active ingredient is alternately coated with layers of differently charged polyelectrolytes (layer-by-layer technology).
- those substances which have the property of forming gels in aqueous solution at temperatures above 40 ° C. are preferably considered as gelling agents.
- Typical examples are heteropolysaccharides and proteins.
- Preferred thermogelling heteropolysaccharides are agaroses which, in the form of the agar agar to be obtained from red algae, may also be present together with up to 30% by weight of non-gel-forming agaropectins.
- the main constituent of the agaroses are linear polysaccharides of D-galactose and 3,6-anhydro-L-galactose, which are linked alternately to ⁇ -1,3- and ⁇ -1,4-glycosidically.
- the heteropolysaccharides preferably have a molecular weight in the range of 110,000 to 160,000 and are both colorless and tasteless.
- Pectins, xanthans (including xanthan gum) as well as their mixtures come into consideration as alternatives. There are also those types are preferred, the aqueous solution still form gels in l-wt .-%, which do not melt below 80 0 C and solidify again above 40 ° C. From the
- thermogeling proteins are exemplified by the different types of gelatin.
- Chitosans are biopolymers and are counted among the group of hydrocolloids. Chemically, they are partially deacetylated chitins of different molecular weight containing the following - idealized - monomer unit:
- chitosans are cationic biopolymers under these conditions.
- the positively charged chitosans can interact with oppositely charged surfaces and are therefore used in cosmetic hair and body care products and pharmaceutical preparations used.
- For the production of chitosans is based on chitin, preferably the shell remains of crustaceans, which are available as cheap raw materials in large quantities available.
- the chitin is thereby used in a process first described by Hackmann et al. has been described, usually initially deproteinized by the addition of bases, demineralized by the addition of mineral acids and finally deacetylated by the addition of strong bases, wherein the molecular weights may be distributed over a broad spectrum.
- the chitosans are generally used in the form of their salts, preferably as glycolates.
- the matrix may optionally be dispersed in an oil phase prior to the formation of the membrane.
- oils for this purpose for example, Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C 6 -C 22 fatty acids with linear C 6 -C 22 fatty alcohols, esters of branched C 6 -Co -
- Carboxylic acids with linear C 6 -C 22 -fatty alcohols such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate , Stearylisostearat, stearyl oleate, stearyl behenate, Stearylerucat, isostearyl, isostearyl palmitate, Isostearylstearat, I- sostearylisostearat, Isostearyloleat, isostearyl behenate
- C 2 2 fatty acids with branched alcohols in particular 2-ethylhexanol, esters of hydroxycarboxylic acids with linear or branched C 6 -C 22 fatty alcohols, in particular dioctyl malates, esters of linear and / or branched fatty acids with polyhydric Alcohols (such as, for example, propylene glycol, dimerdiol or trimer triol) and / or guerbet alcohols, triglycerides based on C 6 -C 10 fatty acids, liquid mono- / di- / triglyceride mixtures based on C 6 -C 18 fatty acids, esters of C 6 -C 22 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, in particular benzoic acid, esters of C 2 -C 2 dicarboxylic acids with linear or branched alcohols having 1 to 22 carbon atoms or polyols having 2 to 10 carbon atoms and 2 to 6 to
- the anionic polymers have the task of forming membranes with the chitosans. Salts of alginic acid are preferably suitable for this purpose.
- Alginic acid is a mixture of carboxyl-containing polysaccharides with the following idealized monomer unit:
- the average molecular weight of the alginic acids or alginates is in the range of 150,000 to 250,000.
- Salts of alginic acid are to be understood as meaning both their complete and their partial neutralization products, in particular the alkali salts and, preferably, the sodium alginate ("algin") and the ammonium and alkaline earth salts, particularly preferred are mixed alginates, such as, for example, sodium / magnesium
- anionic chitosan derivatives such as, for example, carboxylating and, in particular, succinylation products
- poly (meth) acrylates having average molecular weights in the range of 5,000 to 50,000 daltons and the various carboxymethylcelluloses in question.
- anionic polymers it is also possible to use anionic surfactants or low molecular weight inorganic salts, such as, for example, pyrophosphates, for the formation of the enveloping membrane.
- aqueous solution of the gelling agent preferably the agar agar ago and heated them under reflux.
- a second aqueous solution is added, which contains the cationic polymer, preferably the chitosan in amounts of 0.1 to 2, preferably 0.25 to 0.5 wt .-% and the active ingredients in amounts of 0.1 to 25 and in particular 0.25 to 10 wt .-%; this mixture is called a matrix.
- the loading of the microcapsules with active ingredients can therefore also amount to 0.1 to 25% by weight, based on the capsule weight.
- water-insoluble constituents for example inorganic pigments, can also be added at this time to adjust the viscosity, these being added as a rule in the form of aqueous or aqueous / alcoholic dispersions. It may also be useful to emulsify or disperse the active ingredients of the matrix
- the matrix of gelling agent, cation polymer and active ingredients can optionally be very finely dispersed in an oil phase under high shear in order to produce the smallest possible particles in the subsequent encapsulation. It has proved to be particularly advantageous to heat the matrix to temperatures in the range of 40 to 60 0 C while cooling the oil phase to 10 to 20 0 C.
- the actual encapsulation takes place, ie the formation of the enveloping membrane by contacting the cationic polymer in the matrix with the anionic polymers.
- the optionally dispersed in the oil phase matrix at a temperature in the range of 40 to 100, preferably 50 to 60 ° C with an aqueous, about 1 to 50 and preferably 10 to 15 wt .-% aqueous solution of the anion - To treat polymers and thereby - if necessary - at the same time or subsequently to remove the oil phase.
- the resulting aqueous preparations generally have a microcapsule content in the range of 1 to 10 wt .-%.
- the solution of the polymers contains other ingredients, such as emulsifiers or preservatives.
- microcapsules After filtration, microcapsules are obtained, which on average have a diameter in the range of preferably about 0.01 to 1 mm. It is advisable to sieve the capsules in order to Ensures uniform size distribution.
- the microcapsules thus obtained may have any shape in the production-related framework, but they are preferably approximately spherical.
- the encapsulation can also be carried out using cationic polymers exclusively, taking advantage of their property of coagulating at pH values above the pKa value.
- an O / W emulsion is initially prepared for producing the microcapsules according to the invention, which contains an effective amount of emulsifier in addition to the oil body, water and the active ingredients.
- this preparation is mixed with vigorous stirring with an appropriate amount of an aqueous anionic polymer solution.
- the membrane formation takes place by adding the chitosan solution.
- the pH is raised to 5 to 6, for example by addition of triethanolamine or another base. This leads to an increase in the viscosity, which can be increased by adding further thickening agents, such as e.g.
- polysaccharides especially xanthan gum, guar guar, agar, alginates and Tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, high molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyacrylamides and the like can still be supported.
- the microcapsules of the aqueous phase for example by decantation, filtration or
- the formation of the microcapsules takes place around a preferably solid, for example, crystalline core, by coating it in layers with oppositely charged polyelectrolytes.
- a preferably solid, for example, crystalline core by coating it in layers with oppositely charged polyelectrolytes.
- compositions according to the invention exhibit an improved excretion of undesired cholesterol from the blood when taken orally.
- a further subject of the invention therefore relates to the use of mixtures containing
- suitable foods are butter, margarine, edible oils, frying oils and frying fats, spreads, sausage, cheese, mayonnaise, yoghurt, pudding, milk and milk drinks, but also baked goods, biscuits and biscuit bars, and sweets in which the inventive preparations in quantities of 0.01 to 10, preferably 0.1 to 5 and in particular 1 to 2 wt .-% may be included.
- agar-agar were dissolved in 200 ml of water in the boiling heat.
- the mixture was then stirred for about 30 minutes with vigorous stirring first with a solution of 10 g glycerol 90 ml water and then with a preparation of 2.5 g sodium alginate in the form of a 10 wt .-% aqueous solution, 1 g ß- Sitosterol, 1 g of dried Hoodia gordonii extract, 0.5 g of Phenonip® and 0.5 g of polysorbate-20 (Tween® 20, ICI) in 64 g of water.
- the resulting matrix was filtered, heated to 60 ° C and added dropwise to a 1% by weight solution of chitosan glycolate in water. To obtain microcapsules of the same diameter, the preparations were then sieved.
- agar-agar were dissolved in 200 ml of water in the boiling heat. Subsequently, the mixture was stirred for about 30 minutes with vigorous stirring, first with a solution of 10 g of glycerol, 90 ml of water and then with a preparation of 2.5 g of sodium alginate in the form of a 10% strength by weight aqueous solution, 1 g of an ester from ⁇ -sitosterol and CLA, 1 g of dried Hoodia gordonii extract, 0.5 g of Ginkgo biloba extract, 0.5 g of Phenonip® and 0.5 g of polysorbate-20 (Tween® 20, ICI) in 64 g of water. The resulting matrix was filtered, warmed to 60 ° C. and placed in a 1 % By weight solution of chitosan glycolate in water. To obtain microcapsules of the same
- agar-agar were dissolved in 200 ml of water in the boiling heat.
- the mixture was then stirred for about 30 minutes with vigorous stirring first with a solution of 10 g glycerol 90 ml water and then with a preparation of 2.5 g sodium alginate in the form of a 10 wt .-% aqueous solution, 1 g ß- Sitosterol palmitate, 1 g dried Hoodia gordonii extract, 0.5 g dried Vitis vinifera extract, 0.5 g Phenonip® and 0.5 g polysorbate-20 (Tween® 20, ICI) in 64 g of water.
- the resulting matrix was filtered, heated to 60 ° C and added dropwise to a 1% by weight solution of chitosan glycolate in water. To obtain microcapsules of the same diameter, the preparations were then sieved.
- agar-agar were dissolved in 200 ml of water in the boiling heat.
- the mixture was then stirred for about 30 minutes with vigorous stirring first with a solution of 10 g glycerol 90 ml water and then with a preparation of 2.5 g sodium alginate in the form of a 10 wt .-% aqueous solution, 1 g ß- Sitosterol palmitate, 1 g of dried Hoodia gordonii extract, 0.5 g of dried Camellia sinensis extract, 0.5 g of Phenonip® and 0.5 g of polysorbate-20 (Tween® 20, ICI) in 64 g of water.
- the matrix obtained was filtered, heated to 60 0 C and poured into a 1% by weight solution of chitosan glycolate dropped into water. To obtain microcapsules of the same diameter, the preparations were then sieved.
- Gelatine capsules (weight about 1.5 g) containing ⁇ -sitosterol or ⁇ -sitosterol esters and Hoodia and optionally other plant extracts and 0.5% by weight of radiolabeled cholesterol were prepared.
- male rats (individual weight about 200 g) were fasted overnight. The following day, the test animals were each introduced a crushed gelatin capsule with a little saline water via a nasogastric tube. After 3, 6, 12, 24 and 48 h, the animals were bled and the content of radioactive cholesterol was determined. Which he- results, which represent the mean of the measurements of 10 experimental animals, are summarized in Table 1.
- the data on the decrease in radioactivity are in each case with reference to a dummy group of experimental animals to which only gelatin capsules containing 20% by weight of vitamin E and a corresponding amount of radioactively labeled cholesterol had been administered.
- the mixtures 5 to 9 are according to the invention, the mixtures Vl to V3 are for comparison.
- This effect is tended to be reversed by replacing up to 20% by weight of the ⁇ oodia portion with other plant extracts, e.g. Gingko or red clover improved.
Abstract
L'invention concerne des préparations à usage oral contenant (a) des stérols ou des esters de stérols et (b) des extraits de Hoodia ou les glycosides stéroïdiens qui peuvent en être tirés. Elle concerne également l'utilisation de (a) avec (b) pour préparer des produits alimentaires et des médicaments hypocholestérolémiants.
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WO2009045837A1 (fr) * | 2007-09-28 | 2009-04-09 | Zomanex, Llc | Procédés et formulations pour convertir des médicaments intraveineux et injectables en des formes de dosage orales |
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US20040265398A1 (en) * | 2002-04-25 | 2004-12-30 | Fleischner Albert M. | Herbal composition for weight control |
WO2005099737A1 (fr) * | 2004-04-07 | 2005-10-27 | Rutgers, The State University Of New Jersey | Compositions et méthodes coupe-faim |
US20050276869A1 (en) * | 2004-06-14 | 2005-12-15 | Century Systems | Appetite-suppressing, lipase-inhibiting herbal composition |
WO2006051334A1 (fr) * | 2004-11-15 | 2006-05-18 | Phyto Research Ltd | Cellules de plantes et utilisations desdites cellules |
WO2006079056A1 (fr) * | 2005-01-20 | 2006-07-27 | Stephen Holt | Compositions vegetales a base d'hoodia |
WO2007096239A1 (fr) * | 2006-02-23 | 2007-08-30 | Unilever N.V. | Préparations coupe-faim |
-
2006
- 2006-10-13 DE DE102006048530A patent/DE102006048530A1/de not_active Withdrawn
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US20040265398A1 (en) * | 2002-04-25 | 2004-12-30 | Fleischner Albert M. | Herbal composition for weight control |
WO2005099737A1 (fr) * | 2004-04-07 | 2005-10-27 | Rutgers, The State University Of New Jersey | Compositions et méthodes coupe-faim |
US20050276869A1 (en) * | 2004-06-14 | 2005-12-15 | Century Systems | Appetite-suppressing, lipase-inhibiting herbal composition |
WO2006051334A1 (fr) * | 2004-11-15 | 2006-05-18 | Phyto Research Ltd | Cellules de plantes et utilisations desdites cellules |
WO2006079056A1 (fr) * | 2005-01-20 | 2006-07-27 | Stephen Holt | Compositions vegetales a base d'hoodia |
WO2007096239A1 (fr) * | 2006-02-23 | 2007-08-30 | Unilever N.V. | Préparations coupe-faim |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2009045837A1 (fr) * | 2007-09-28 | 2009-04-09 | Zomanex, Llc | Procédés et formulations pour convertir des médicaments intraveineux et injectables en des formes de dosage orales |
AU2008309010B2 (en) * | 2007-09-28 | 2012-07-19 | Zomanex, Llc | Methods and formulations for converting intravenous and injectable drugs into oral dosage forms |
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