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WO2021177660A1 - Composition de perte de poids comprenant des analogues de l'œnothéine b en tant que principe actif - Google Patents

Composition de perte de poids comprenant des analogues de l'œnothéine b en tant que principe actif Download PDF

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Publication number
WO2021177660A1
WO2021177660A1 PCT/KR2021/002392 KR2021002392W WO2021177660A1 WO 2021177660 A1 WO2021177660 A1 WO 2021177660A1 KR 2021002392 W KR2021002392 W KR 2021002392W WO 2021177660 A1 WO2021177660 A1 WO 2021177660A1
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formula
group
obesity
integer
oenotein
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English (en)
Korean (ko)
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하운환
전현식
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Metaimmunetech Inc
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Metaimmunetech Inc
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    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/163—Sugars; Polysaccharides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7024—Esters of saccharides
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • 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
    • A23V2200/00—Function of food ingredients
    • A23V2200/30—Foods, ingredients or supplements having a functional effect on health
    • A23V2200/332—Promoters of weight control and weight loss

Definitions

  • the present invention relates to a composition
  • a composition comprising an oenotein B analogue as an active ingredient, which has an effect on anti-obesity or weight loss, more preferably, body fat loss, and a use thereof.
  • Obesity refers to a state of excessive accumulation of adipose tissue, but excessive accumulation of adipose tissue increases the risk of metabolic syndrome such as hypertension and diabetes, and is also associated with the occurrence of cardiovascular diseases.
  • oriental medicine clinics treat not only general obesity but also partial obesity through prescription-based herbal medicine therapy, acupuncture treatment, acupuncture electrostimulation therapy, and medicinal acupuncture treatment. .
  • the effect of obesity treatment can be reliably obtained without side effects, and obesity treatment methods or novel anti-obesity methods that can be conveniently applied without special effort.
  • An object of the present invention is to provide a pharmaceutical composition for treating or preventing obesity, complications of obesity, or both, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof as an active ingredient.
  • Another object to be solved by the present invention is to provide a food composition for improving obesity, weight loss, or weight loss, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
  • Another object to be solved by the present invention is to provide an animal feed composition for alleviating or preventing obesity, obesity complications, or both, including an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
  • Another object to be solved by the present invention is to provide a low-fat-containing livestock feed composition comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
  • the present invention provides a pharmaceutical composition for the treatment or prevention of obesity, obesity complications, or both, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof as an active ingredient.
  • the pharmaceutical composition for the treatment or prevention of obesity, obesity complications, or both may be to reduce the amount of body fat.
  • the composition may reduce the amount of one or more fats selected from abdominal fat, visceral fat, intramuscular fat, and blood fat.
  • the present invention provides a food composition for improving obesity, weight loss, or reducing body fat, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
  • the food composition may be a health functional food, but is not limited thereto.
  • the present invention provides an animal feed composition for alleviating or preventing obesity, obesity complications, or both, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
  • the animal may be one or more animals selected from mammals and birds.
  • the present invention provides a low-fat-containing livestock feed composition
  • a low-fat-containing livestock feed composition comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
  • composition comprising an oenotein B analogue compound or a pharmaceutically acceptable salt thereof according to the present invention exhibited an effective weight loss effect in normal or obese animal models, and the weight loss can reduce fat without loss of muscle mass. Since it did not show side effects such as dehydration symptoms, stress, decreased physical strength or toxicity even after weight loss, it is used for weight loss, body fat loss, obesity treatment, improvement or prevention for pharmaceutical compositions, food compositions, feed compositions, etc. can be usefully applied.
  • the composition comprising the oenotein B analogue compound or a pharmaceutically acceptable salt thereof according to the present invention is applied to the livestock industry, the fat content can be reduced in edible livestock such as broilers in which the fat layer accumulated in the muscle is a problem, useful as
  • the present invention confirmed the pharmacological effect of an oenotein B analogue compound or a pharmaceutically acceptable salt thereof on anti-obesity. was completed.
  • the present invention provides a pharmaceutical composition for the treatment or prevention of obesity, obesity complications, or both, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof as an active ingredient.
  • the term "obesity complications” refers to various diseases having a prevalence due to excessive accumulation of fat, and the complications include metabolic syndromes such as hypertension, diabetes, and hyperlipidemia. Also included are herniated discs, osteoarthritis (eg, osteoarthritis of the ankle, knee joint, hip joint, etc.). Also included are gastroesophageal reflux disease, hernia, and stress incontinence due to abdominal obesity. Also included are sleep apnea and nonalcoholic fatty liver disease, which is caused by a decrease in the space in the throat due to obesity. Also included are cardiovascular diseases such as angina pectoris, myocardial infarction, and heart failure. Also included are cerebrovascular diseases such as stroke and cerebral infarction.
  • a decrease in neurological function due to an increase in oxidative stress is included.
  • various diseases such as early onset of menstruation, ovulation disorder, luteal phase defect, postmenopausal health, precocious puberty, menstrual irregularity, infertility, polycystic ovary syndrome and female hormone-dependent cancer caused by an increase in female hormones due to excessive body fat in women Included.
  • the obesity complication is hypertension; diabetes; hyperlipidemia;
  • the oenotein of the present invention has four benzoic acids attached to glucose as a basic monomer, and oenoteins A, B, C, D, F, and G exist, which are structurally very similar and In the present invention, it is included in the term “oenotein B analog” (Phytochemistry 40:555-561, 1995).
  • Oenotein B (CAS# 104987-36-2) is a dimeric ellagitannin composed of C68H48O44 having a molecular weight of 1569.08. It was first discovered in the leaves of Oenothera erythrosepala (J. Chem. Soc. Perkin Trans. 1, 2735-2743, 1990), may be represented by the following formula (3).
  • the oenotein B analog is a monomer or dimer compound of a compound represented by the following formula (1); or a pharmaceutically acceptable salt thereof:
  • R 2 is (CH 2 ) n , where n is an integer from 1 to 6,
  • R3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,
  • R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano to the furnace, halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, phenylmethoxy, etc. Any one selected from the group consisting of,
  • R 7 and R 8 are —OH.
  • R 7 and R 8 are condensed with R 4 , respectively.
  • R 7 and R 8 and R 4 and each condensation may be connected to any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) p -, where p is an integer from 1 to 6.
  • dimer compound of the compound of Formula 1 it may be a compound represented by the following Formula 2 or a pharmaceutically acceptable salt thereof:
  • R 2 is (CH 2 ) n , where n is an integer from 1 to 6,
  • R 3 is any one selected from the group consisting of -O-, -CH 2 - and -O(CH 2 ) m -, wherein m is an integer from 1 to 6,
  • R 4, R 4 ', R 5 and R 6 are the same or different from each other and each independently represents H, (C l-3) alkyl, (C l- 3) alkenyl, (C l- 3) alkynyl , cyano to the furnace, halo, nitro, alkylthio, phenyl, hydroxyl, (C l- 3) alkoxy, (C 2- 4) acyloxy, (C l- 3) carboxamide Mino, phenoxy, phenylmethoxy, etc. Any one selected from the group consisting of, and
  • R 7 ' and R 8 ' are each independently selected from the group consisting of -O-, -CH 2 -, and -O(CH 2 ) p -, wherein p is an integer of 1 to 6.
  • the compound according to the present invention may be a compound represented by the following formula (3) or a pharmaceutically acceptable salt thereof:
  • pharmaceutically acceptable salts refer to salts commonly used in the pharmaceutical industry, for example, inorganic ionic salts prepared from calcium, potassium, sodium and magnesium, hydrochloric acid, nitric acid, phosphoric acid, hydrobromic acid, and iodine.
  • Inorganic acid perchloric acid, tartaric acid and sulfuric acid, acetic acid, trifluoroacetic acid, citric acid, maleic acid, succinic acid, oxalic acid, benzoic acid, tartaric acid, fumaric acid, manderic acid, propionic acid, citric acid, lactic acid, glycolic acid, gluconic acid , galacturonic acid, glutamic acid, glutaric acid, glucuronic acid, aspartic acid, ascorbic acid, carbonic acid, vanillic acid, hydroiodic acid, etc.
  • organic acid salts methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p -There are sulfonic acid salts prepared from toluenesulfonic acid and naphthalenesulfonic acid, amino acid salts prepared from glycine, arginine, lysine, etc., and amine salts prepared from trimethylamine, triethylamine, ammonia, pyridine, picoline, etc. The types of salts in the present invention are not limited by these listed salts.
  • the composition may be to treat or prevent obesity by reducing the amount of body fat.
  • the composition may treat or prevent obesity, obesity complications, or both by reducing the amount of one or more fats selected from abdominal fat, visceral fat, intramuscular fat, and blood fat.
  • Abdominal obesity or visceral obesity is a symptom of the accumulation of fat in the subcutaneous or internal organs of the abdomen and is known to accompany various complications.
  • the composition according to the present invention can also be used for the treatment or prevention of the above-mentioned complications of obesity.
  • composition according to the present invention can selectively reduce fat without loss of muscle mass, and has very low cytotoxicity, so it is effective in treating or preventing obesity, obesity complications, or both.
  • composition according to the present invention has excellent effects in that it reduces the content of neutral triglycerides and lipids without toxicity in the human body, and exhibits a weight loss effect and an effect on reducing abdominal fat.
  • the term "treatment” refers to both the action of alleviating the symptoms caused by obesity and obesity complications by administering the composition, and the disease, the symptoms of the disease, the secondary disease of the disease or disease, or To a subject (human or animal) having a disease, a symptom of a disease, a secondary disease of the disease or disorder, or a predisposition thereto, for the purpose of treating, alleviating, alleviating, remedying, or ameliorating the predisposition It is defined as the application or administration of the composition.
  • the pharmaceutical composition of the present invention may contain 0.01 to 95% by weight, preferably 1 to 80% by weight of the oenotein B analog compound or a pharmaceutically acceptable salt thereof, based on the total weight of the composition.
  • the oenotein B analog compound or a pharmaceutically acceptable salt thereof is mixed with a conventional carrier, adjuvant or diluent and formulated in a conventional formulation method for oral or parenteral administration. It can be prepared in any suitable form.
  • the carrier, adjuvant or diluent may include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, poly vinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil.
  • conventional fillers, extenders, binders, wetting agents, disintegrants, surfactants, etc. may be further included, and lubricants such as magnesium stearate and talc may be further added.
  • oral administration it may be prepared in the form of tablets, capsules, solutions, syrups, suspensions, etc.
  • parenteral administration it is suitable for intravenous, intrauterine, intraperitoneal, subcutaneous, intramuscular, transdermal and intracerebrovascular injection. It can be prepared in the form of an injection for
  • the pharmaceutical composition of the present invention is an amount of an active ingredient or pharmaceutical composition that induces a biological or medical response in a tissue system, animal or human as considered by a researcher, veterinarian, physician or other clinician, that is, the amount of the symptom of the disease or disorder being treated. It can be administered in a therapeutically effective amount, which is an amount that induces remission. It is apparent to those skilled in the art that the therapeutically effective dosage and frequency of administration for the pharmaceutical composition of the present invention will vary depending on the desired effect.
  • the optimal dosage to be administered can be easily determined by those skilled in the art, and the type of disease, the severity of the disease, the content of active ingredients and other ingredients contained in the composition, the type of formulation, the age, weight, and general health of the patient , sex and diet, administration time, administration route and secretion rate of the composition, treatment period, and various factors including concurrently used drugs.
  • the pharmaceutical composition of the present invention may be administered to an individual by various routes. For example, intravenous, intraperitoneal, intramuscular, intraarterial, buccal, intracardiac, intramedullary, intrathecal, transdermal, enteral, subcutaneous, sublingual or topical administration may be administered, but not limited thereto.
  • the pharmaceutical composition of the present invention may be administered in an amount of 1 to 10,000 mg/kg/day, preferably 1 to 200 mg/kg/day, and may be administered once a day or divided into several administrations .
  • Another object to be solved by the present invention is to provide a food composition for improving obesity, weight loss or body fat loss, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
  • the present invention provides a food composition for improving obesity or reducing body fat containing oenotein B.
  • the food composition of the present invention can be used as a health functional food.
  • health functional food means a food manufactured and processed using raw materials or ingredients useful for the human body in accordance with the Health Functional Food Act, and "functionality” refers to the structure and function of the human body. It refers to ingestion for the purpose of obtaining useful effects for health purposes such as regulating nutrients or physiological effects.
  • the food composition of the present invention may contain conventional food additives, and the suitability as the "food additive” is determined according to the general rules and general test methods of food additives approved by the Ministry of Food and Drug Safety, unless otherwise specified. It is judged according to the standards and standards related to the item.
  • Food Additives Code include, for example, chemical compounds such as ketones, glycine, potassium citrate, nicotinic acid, and cinnamic acid; Mixed preparations such as sodium L-glutamate preparation, noodle-added alkali agent, preservative agent, and tar color agent can be mentioned.
  • the food composition of the present invention may contain 0.01 to 95% by weight, preferably 1 to 80% by weight of the oenotein B analog compound or a pharmaceutically acceptable salt thereof, based on the total weight of the composition.
  • the food composition of the present invention can be manufactured and processed in the form of tablets, capsules, powders, granules, liquids, pills, etc. for the purpose of improving obesity, weight loss or body fat loss.
  • the health functional food in the form of tablets is granulated with a mixture of oenotein B analogs, excipients, binders, disintegrants, and other additives in a conventional manner, and then compression-molded by adding a lubricant, etc.;
  • the mixture can be directly compression molded.
  • the health functional food in the form of tablets may contain a mating agent, etc., if necessary, and may be coated with a suitable skinning agent if necessary.
  • hard capsules can be prepared by filling conventional hard capsules with a mixture of oenotein B analogues and additives such as excipients, or granules thereof or coated granules. can be prepared by filling a mixture of an oenotein B analogue and an additive such as an excipient into a capsule base such as gelatin.
  • the soft capsule formulation may contain a plasticizer such as glycerin or sorbitol, a colorant, a preservative, and the like, if necessary.
  • a health functional food in the form of a ring can be prepared by molding a mixture of oenotein B analogues, excipients, binders, disintegrants, etc. in an appropriate way, and if necessary, the skin is coated with sucrose or other suitable skinning agent, or starch, talc, or You can also dress the gown with a suitable material.
  • a health functional food in granular form may be prepared in a granular form by a suitable method of a mixture of oenotein B analogues, excipients, binders, disintegrants, etc., and may contain flavoring agents, flavoring agents, etc. as needed.
  • For health functional foods in granular form use No. 12 (1680 ⁇ m), No. 14 (1410 ⁇ m) and No. 45 (350 ⁇ m) sieves to pass all the sieves No. 12 and the remaining in No. 14 sieves in the next particle size test. 5.0% or less and passing through No. 45 may be less than 15.0% of the total amount.
  • Examples of foods to which the oenotein B analogue of the present invention can be added include beverages, gums, vitamin complexes, drinks, and the like, and include all health functional foods in a conventional sense.
  • the food composition may contain food supplement additives, and the food products include, for example, beverages, gum, tea, vitamin complexes, health supplements, etc., capsules, tablets, powders, granules, liquids, pills, slices, pastes. It can be used in the form of phases, syrups, gels, beverages, jellies or vines.
  • the content of the oenotein B analogue may be contained in an amount of 0.01 to 15% by weight based on the total weight of the health functional food, and in the case of a health beverage composition, 0.02 to 10 g, preferably 0.3 to 1, based on a total of 100 g g may contain.
  • the food supplement additives include food additives conventional in the art, for example, flavoring agents, flavoring agents, coloring agents, fillers, stabilizers, and the like.
  • the health drink composition is an essential ingredient in the indicated ratio, and there is no particular limitation on the ingredients added other than the oenotein B analog, and it can contain various flavoring agents or natural carbohydrates as additional ingredients like conventional beverages.
  • the natural carbohydrate include monosaccharides such as glucose, fructose and the like; disaccharides such as maltose, sucrose and the like; polysaccharides such as dextrins, cyclodextrins; and sugar alcohols such as xylitol, sorbitol, and erythritol.
  • natural flavoring agents taumatin, stevia extract (eg rebaudioside A, glycyrrhizin, etc.)
  • synthetic flavoring agents sacharin, aspartame, etc.
  • food compositions, diet supplements, or health functional foods containing an oenotein B analogue compound or a pharmaceutically acceptable salt thereof include various nutrients, vitamins, minerals (electrolytes), synthetic flavors and natural flavors. Flavoring, coloring and thickening agents (cheese, chocolate, etc.), pectic acid and its salts, alginic acid and its salts, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohols, carbonates used in carbonated beverages It may contain topics and the like.
  • the present invention provides an animal feed composition for improving or preventing obesity and obesity complications, comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
  • the animal may be one or more selected from mammals and birds, and preferably, the wild habits defined in Article 2, No. 1 of the Livestock Livestock Act and Article 2 of the Enforcement Rule of the same Act, and are suitable for breeding. And it can be a livestock that can contribute to the income increase of the farmhouse.
  • the livestock may be cattle, horses, mules, donkeys, goats, goats, sheep, deer, pigs, rabbits, poultry, etc., and poultry includes chickens, turkeys, ducks, ostriches, geese, quails, etc., preferably chickens, If it is suitable for breeding and obtaining livestock products, it is not limited thereto.
  • livestock products are meat, milk, eggs, honey and their processed products, raw hides (including raw fur), raw wool, and other livestock products, which are defined by Article 2, 3 of the Livestock Act, as determined by the Ordinance of the Ministry of Agriculture and Forestry. means that In addition, it may be a dog, a cat, etc., including companion animals, but is not limited thereto.
  • feed in the present invention means any natural or artificial diet, meal, etc., or a component of said meal, intended for or suitable for being eaten, consumed, and digested by an animal.
  • the composition for feed containing the oenotein B analog compound of the present invention or a pharmaceutically acceptable salt thereof may include a concentrated feed, forage and/or special feed.
  • seed fruits containing grains such as wheat, oats, and corn, bran containing rice bran, bran, barley bran, etc.
  • Fish-soluble, meat powder which is a condensed product of fish meal, fish waste, and fresh liquid obtained from fish meal, fish waste, fish meal, fish meal , animal feed such as dried whey, yeast, chlorella, seaweed, etc., blood meal, feather meal, skim milk powder, cheese from milk, and whey, which is the remainder of the production of casein from skim milk.
  • silage which is a stored feed fermented with lactic acid after being filled, wild grasses, hay obtained by cutting and drying grass, straw for breeding crops, and leaves from legumes.
  • Special feed includes mineral feed such as oyster shells and rock salt, urea feed such as urea or its derivative diureide isobutane, supplementing ingredients that are easily lacking when only natural feed ingredients are blended, or added to formulated feed to increase feed storage.
  • feed additives which are substances added in trace amounts.
  • the present invention provides a low-fat-containing livestock feed composition
  • a low-fat-containing livestock feed composition comprising an oenotein B analog compound or a pharmaceutically acceptable salt thereof.
  • the oenotein B analog can be usefully applied as an additive to a low-fat-containing livestock fattening feed composition because it reduces the body fat content without loss of muscle mass.
  • the present invention provides the use of an oenotein B analog compound represented by Formula 1 or Formula 2, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment of obesity, obesity complications, or both.
  • the present invention relates to obesity, obesity complications, Methods for preventing or treating all of these are provided.
  • the term "subject" may refer to all animals, including humans, that have or are likely to develop obesity or obesity complications.
  • the animal may be a mammal, such as a cow, a horse, a sheep, a pig, a goat, a camel, an antelope, a dog, or a cat, in need of treatment for symptoms similar to those of humans as well as humans. It may also refer to animals other than humans, but is not limited thereto.
  • the prevention or treatment method of the present invention may include administering the composition in a pharmaceutically effective amount to an individual who has developed or is at risk of developing obesity or obesity complications.
  • the present invention provides a composition comprising an oenotein B analogue compound represented by Formula 1 or Formula 2 or a pharmaceutically acceptable salt thereof for use in the treatment of obesity, obesity complications, or both.
  • the definition of the oenotein B analog compound represented by Formula 1 or Formula 2, a pharmaceutically acceptable salt thereof, obesity or obesity complications is as described above.
  • reagents and solvents mentioned below were purchased from Sigma-Aldrich, TCI or Alfa aesar, unless otherwise specified, and HPLC grade was used.
  • Test Example 1 Weight loss effect of oenotein B in a normal-weight animal model
  • Oenotein B was dissolved in sterile distilled water to prepare a solution of 20 mg/mL. After diluting the prepared solution 20-fold with saline, 200 ⁇ L of oenotein B (1 mg/mL) was injected into the abdominal cavity of C57BL6/J mice with an average age of 13 weeks using a 1cc syringe on days 1 and 3 of the experiment. The injections were made at intervals of time, and body weight changes were measured daily for 5 days after injection, starting one day before the injection of oenotein B solution. Distilled water was used as a control, and normal feed and water with a fat content of 15% were provided during the experiment.
  • FIG. 1 shows a graph showing the weight loss effect of oenotein B.
  • Arrows indicate the time of injection of oenotein B. After the first injection of oenotein B, a weight loss effect was observed, and 1.5 to 8.5% of body weight was lost after the first injection, and 1.5 to 6% of body weight was lost after the second injection.
  • Test Example 2 Weight loss effect of oenotein B in obese animal model
  • the weight loss effect of oenotein B in an obese animal model was confirmed using overweight-induced mice.
  • C57BL/6J mice with an average age of 12 weeks were fed after changing the normal diet (fat content 15%) to a high-fat diet containing 45% fat, and the change in body weight was measured daily.
  • 200 ⁇ L of oenotein B (1 mg/mL) was injected into the abdominal cavity of the mice, and body weight changes were measured every day until the 27th day, and the control group was injected with distilled water.
  • Test Example 3 Weight loss effect of oenotein B in obese animal model
  • mice administered oenotein B compared to the control group, it was confirmed that the average abdominal fat was reduced by about 44%.
  • Oil red O is a dye used to stain neutral triglycerides and lipids.
  • A549 cells a cell line obtained from human lung cancer tissue, were mixed with 10% fetal bovine serum in RPMI-1640 medium and cultured at 37° C. and 5% CO 2 conditions.
  • lactate dehydrogenase (LDH) release assay was performed to quantitatively measure cytotoxicity, and the results are shown in FIG. 5 .
  • Hydrogen peroxide was used as a positive control, and phosphate-buffered saline was used as a negative control.
  • the composition comprising the oenotein B analog according to the present invention is a pharmaceutical composition, a food composition for weight loss, treatment, prevention or improvement of obesity and obesity complications, in particular, health for weight loss or body fat loss It can be usefully applied as a functional food, a feed composition, and further can be usefully used as a feed composition for fattening livestock containing low fat.

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  • Diabetes (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La présente invention concerne une composition pharmaceutique destinée à traiter ou prévenir l'obésité et/ou des complications de l'obésité, et une composition alimentaire ou une composition nutritionnelle destinée à la prévention de l'obésité, la perte de poids ou la perte de graisses, qui comprennent toutes des analogues de l'œnothéine B.
PCT/KR2021/002392 2020-03-05 2021-02-25 Composition de perte de poids comprenant des analogues de l'œnothéine b en tant que principe actif Ceased WO2021177660A1 (fr)

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KR10-2020-0027912 2020-03-05
KR1020200027912A KR102376806B1 (ko) 2020-03-05 2020-03-05 오에노테인 b 유사체를 유효성분으로 포함하는 체중 감량용 조성물

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WO2021177660A1 true WO2021177660A1 (fr) 2021-09-10

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JP2024069086A (ja) * 2022-11-09 2024-05-21 長岡香料株式会社 体脂肪蓄積抑制剤および体重抑制剤

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JPH07188275A (ja) * 1993-11-16 1995-07-25 Roussel Uclaf アンドロゲン過多症と関連した障害の治療用薬剤を得るためのイーノセインｂ、それを含有する製薬組成物及びエピロビウム・パルビフロラムからの製造法
US20030004131A1 (en) * 1999-09-10 2003-01-02 Warren Steck Oenothein medicaments
JP2009102288A (ja) * 2007-10-19 2009-05-14 Harunire Bio Kenkyusho:Kk 脂肪蓄積阻害剤
US20130030007A1 (en) * 2010-01-07 2013-01-31 Akron Molecules Gmbh Obesity Small Molecules

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KR20140021401A (ko) 2012-08-10 2014-02-20 코웨이 주식회사 정수기 동작 검사 장치 및 이를 이용한 정수기의 동작 검사 방법

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JPH07188275A (ja) * 1993-11-16 1995-07-25 Roussel Uclaf アンドロゲン過多症と関連した障害の治療用薬剤を得るためのイーノセインｂ、それを含有する製薬組成物及びエピロビウム・パルビフロラムからの製造法
US20030004131A1 (en) * 1999-09-10 2003-01-02 Warren Steck Oenothein medicaments
JP2009102288A (ja) * 2007-10-19 2009-05-14 Harunire Bio Kenkyusho:Kk 脂肪蓄積阻害剤
US20130030007A1 (en) * 2010-01-07 2013-01-31 Akron Molecules Gmbh Obesity Small Molecules

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YOSHIDA TAKASHI, YOSHIMURA MORIO, AMAKURA YOSHIAKI: "Chemical and Biological Significance of Oenothein B and Related Ellagitannin Oligomers with Macrocyclic Structure", MOLECULES, vol. 23, no. 3, pages 552, XP055847346, DOI: 10.3390/molecules23030552 *

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KR102376806B1 (ko) 2022-03-21

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