WO2015086811A1 - Methods and compositions for increasing energy expenditure using cinnamaldehyde - Google Patents
Methods and compositions for increasing energy expenditure using cinnamaldehyde Download PDFInfo
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- WO2015086811A1 WO2015086811A1 PCT/EP2014/077544 EP2014077544W WO2015086811A1 WO 2015086811 A1 WO2015086811 A1 WO 2015086811A1 EP 2014077544 W EP2014077544 W EP 2014077544W WO 2015086811 A1 WO2015086811 A1 WO 2015086811A1
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- cinnamaldehyde
- composition
- food product
- energy expenditure
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- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 title claims abstract description 76
- 229940117916 cinnamic aldehyde Drugs 0.000 title claims abstract description 76
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 title claims abstract description 76
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Classifications
-
- 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
- A61K31/11—Aldehydes
-
- 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
-
- 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
- A23L33/30—Dietetic or nutritional methods, e.g. for losing weight
-
- 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)
- A61K36/54—Lauraceae (Laurel family), e.g. cinnamon or sassafras
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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 present disclosure generally relates to methods and compositions for increasing energy expenditure. More specifically, the present disclosure relates to compositions comprising cinnamaldehyde in an amount that increases energy expenditure and fat oxydation while being suitable for oral consumption.
- TRPVl transient receptor potential VI
- TRPA1 transient receptor potential Al
- TRPVl agonist capsaicin is well known as increasing energy expenditure and fat oxidation, but the efficient doses are intermediate to high (20 mg and more). See, e.g.,
- capsaicin is a particularly pungent and toxic compound. Physiological effects associated with oral administration of capsaicin include a burning sensation of heat from the mid-tongue to the throat, shortness of breath, fainting, nausea, and spontaneous vomiting. As a result, only small quantities of capsaicin may be administered without causing discomfort to the individual. Food products containing capsaicin are frequently not accepted by the consumer because such products provide a very unpleasant mouth feeling. In particular, the burning effects are considered to be very unsavory, affecting the consumption of the food product.
- capsaicin the only spice-derived ingredient showing an impact on human metabolism is capsaicin.
- Gregersen et al. "Acute effects of mustard, horseradish, black pepper and ginger on energy expenditure, appetite, ad libitum energy intake and energy balance in human subjects," Br. J. Nutr., 5:1 -8 (July 2012).
- the effective dosage of capsaicin is too intense to be included in a food product, due to spicy taste, or to be ingested, due to gastrointestinal intolerance.
- Cinnamaldehyde is a ⁇ , ⁇ -unsaturated aldehyde that activates TRPA1, but not TRPV I or TRPM8, with an EC 0 of approximately 60 ⁇ . Cinnamaldehyde interacts with TRPA 1 in a covalent manner.
- the present inventors surprisingly and unexpectedly found that cinnamaldehyde obtained a significantly higher impact on energy expenditure and sympathetic nervous system activity and an equivalent effect on fat oxidation compared to capsaicin, at a flavoring level of cinnamaldehyde judged significantly less intense than capsaicin. Consequently, unlike the spicy ingredient capsaicin, cinnamaldehyde can impact energy expenditure, sympathetic nervous system activity, and fat oxidation at concentrations in food that are tolerable both in flavor/taste and in the gastrointestinal tract.
- the present disclosure provides a method for weight maintenance.
- the method comprises administering to a mammal in need thereof a composition comprising cinnamaldehyde.
- the cinnamaldehyde is administered in an amount of about 1.25 mg/kg body weight per day.
- the cinnamaldehyde is present in the composition in an amount of 17.48 ppm to 6191.0 ppm. [0010] In an embodiment, the composition comprising cinnamaldehyde is administered once daily.
- the composition comprises cinnamon essential oil extract that provides at least a portion of the cinnamaldehyde.
- At least a portion of the cinnamaldehyde is selected from the group consisting of isolated cinnamaldehyde and synthesized cinnamaldehyde.
- the present disclosure provides a method for promoting weight loss.
- the method comprises administering to a mammal in need thereof a composition comprising cinnamaldehyde.
- the present disclosure provides a method for preventing obesity or overweight.
- the method comprises administering to a mammal at risk thereof a composition comprising cinnamaldehyde.
- the present disclosure provides a method for treating obesity or overweight.
- the method comprises administering to a mammal in need thereof a composition comprising cinnamaldehyde.
- the present disclosure provides a composition comprising cinnamaldehyde in an amount that is orally tolerable and effective to increase at least one of energy expenditure, sympathetic nervous system activity, or fat oxidation.
- the composition is a food product in which the cinnamaldehyde is present in an amount of 17.48 ppm to 6191.0 ppm.
- the composition is a food product comprising a component selected from the group consisting of protein, carbohydrate, fat and combinations thereof.
- the composition is selected from the group consisting of a medicament, a food product, and a supplement to a food product.
- the composition further comprises an additional ingredient in a therapeutically effective amount to promote weight maintenance or weight loss.
- the present disclosure provides a method for promoting weight loss.
- the method comprises administering a composition comprising cinnamaldehyde to an individual on a weight loss program.
- An advantage of the present disclosure is to increase energy expenditure. [0023] Another advantage of the present disclosure is to increase sympathetic nervous system activity.
- Still another advantage of the present disclosure is to increase fat oxidation.
- Yet another advantage of the present disclosure is to increase energy expenditure, sympathetic nervous system activity, and fat oxidation with a compound that can be easily and safely used in food products.
- An additional advantage of the present disclosure is to increase energy expenditure, sympathetic nervous system activity, and fat oxidation with a naturally-occurring compound that can be found in spices.
- Another advantage of the present disclosure is to increase energy expenditure, sympathetic nervous system activity, and fat oxidation with tolerable side effects or no side effects.
- Yet another advantage of the present disclosure is to support weight management, promote weight loss, and/or treat or prevent obesity or overweight.
- Still another advantage of the present disclosure is to increase energy expenditure, sympathetic nervous system activity, and fat oxidation with a compound that has increased acceptability, reduced pungency, and improved tolerance in the gastrointestinal tract relative to capsaicin.
- Fig. 1 shows the chemical structure of cinnamaldehyde.
- Fig. 2 shows a proposed mechanism by which cinnamaldehyde can increase energy expenditure, sympathetic nervous system activity, and fat oxidation.
- Fig. 3 shows a graph of energy expenditure as a function of time elapsed after ingestion of various compounds.
- Fig. 4 shows a graph of energy expenditure based on AUC after ingestion of various compounds.
- Fig. 5 shows a graph of postprandial fat oxidation as a function of time elapsed after ingestion of various compounds.
- Fig. 6 shows a graph of postprandial fat oxidation based on AUC after ingestion of various compounds.
- Fig. 7 shows a graph of nose temperature increases experienced after ingestion of various compounds.
- Fig. 8 shows a graph and a table of chin temperature, relative to baseline, as a function of time elapsed after ingestion of various compounds.
- Fig. 9 shows taste testing results comparing 4.88 ppm of capsaicin and 350 ppm of cinnamaldehyde.
- prevention includes reduction of risk and/or severity of a condition or disorder.
- treatment includes both prophylactic or preventive treatment (that prevent and/or slow the development of a targeted pathologic condition or disorder) and curative, therapeutic or disease-modifying treatment, including therapeutic measures that cure, slow down, lessen symptoms of, and/or halt progression of a diagnosed pathologic condition or disorder; and treatment of patients at risk of contracting a disease or suspected to have contracted a disease, as well as patients who are ill or have been diagnosed as suffering from a disease or medical condition.
- the term does not necessarily imply that a subject is treated until total recovery.
- treatment also refer to the maintenance and/or promotion of health in an individual not suffering from a disease but who may be susceptible to the development of an unhealthy condition.
- treatment also intended to include the potentiation or otherwise enhancement of one or more primary prophylactic or therapeutic measure.
- treatment also intended to include the dietary management of a disease or condition or the dietary management for prophylaxis or prevention a disease or condition.
- a treatment can be patient- or doctor-related.
- Weight loss is a reduction of the total body weight. Weight loss may, for example, refer to the loss of total body mass in an effort to improve fitness, health, and/or appearance.
- Weight management or “weight maintenance” relates to maintaining a total body weight. For example, weight management may relate to maintaining a BMI in the area of 18.5-25 which is considered to be normal.
- an "effective amount” is an amount that prevents a deficiency, treats a disease or medical condition in an individual or, more generally, reduces symptoms, manages progression of the diseases or provides a nutritional, physiological, or medical benefit to the individual.
- Animal includes, but is not limited to, mammals, which includes but is not limited to, rodents, aquatic mammals, domestic animals such as dogs and cats, farm animals such as sheep, pigs, cows and horses, and humans. Where “animal,” “mammal” or a plural thereof is used, these terms also apply to any animal that is capable of the effect exhibited or intended to be exhibited by the context of the passage.
- the term “patient” is understood to include an animal, especially a mammal, and more especially a human that is receiving or intended to receive treatment, as treatment is herein defined. While the terms “individual” and “patient” are often used herein to refer to a human, the present disclosure is not so limited.
- the terms “individual” and “patient” refer to any animal, mammal or human, that can benefit from the treatment.
- the present inventors surprisingly and unexpectedly found that cinnamaldehyde obtained a significantly higher impact on energy expenditure and sympathetic nervous system activity and an equivalent effect on fat oxidation compared to capsaicin, at a flavoring level of cinnamaldehyde judged significantly less intense than capsaicin. Consequently, unlike the spicy ingredient capsaicin, cinnamaldehyde can impact energy expenditure, sympathetic nervous system activity, and fat oxidation at concentrations in food that are tolerable both in flavor/taste and in the gastrointestinal tract.
- a low dose (1.25mg kg body weight per day) of cinnamaldehyde at a flavoring range can provide an effect after a single ingestion.
- the dose of cinnamaldehyde was about 250 mg kg body weight per day, with chronic ingestion (effect on body weight gain and insulin sensitivity).
- the composition provided by the present disclosure comprises an amount of cinnamaldehyde that is orally tolerable, for example does not cause an unpleasant mouth feeling, and is effective to increase at least one of energy expenditure, sympathetic nervous system activity, or fat oxidation, relative to an otherwise identical composition lacking cinnamaldehyde.
- the concentration of cinnamaldehyde is from 17.48 ppm to 6191.0 ppm, preferably about 350 ppm.
- Cinnamaldehyde is available commercially.
- the cinnamaldehyde in the composition can be provided in a cinnamon essential oil extract, for example an extract from steam distillation of the oil of cinnamon bark; can be isolated cinnamaldehyde, for example isolated from cinnamon essential oil; or can be synthesized cinnamaldehyde, for example the product of aldol condensation of benzaldehyde and acetaldehyde.
- the composition comprising cinnamaldehyde can be used in a method to support weight management or promote weight loss.
- the composition can be administered to a mammal managing their weight or undergoing a weight loss program, such as a weight loss diet (e.g., one or more of a low-fat diet, a low-carbohydrate diet, a low-calorie diet and a very low-calorie diet) and/or a weight loss training regimen (e.g. endurance and/or strength training).
- a weight loss diet e.g., one or more of a low-fat diet, a low-carbohydrate diet, a low-calorie diet and a very low-calorie diet
- a weight loss training regimen e.g. endurance and/or strength training.
- the composition comprising cinnamaldehyde can be used in a method for preventing obesity or overweight by administering the composition to a mammal at risk thereof.
- the composition comprising cinnamaldehyde can be used in a method for treating obesity or overweight by administering the composition to a mammal in need thereof.
- the composition comprising cinnamaldehyde is administered to a human.
- the composition comprising cinnamaldehyde can be administered in an amount of about 1.25 mg/kg body weight/day in a single dose, although multiple doses are also encompassed by the present disclosure.
- the composition can also comprise an additional weight loss ingredient.
- the composition comprising cinnamaldehyde may be a medicament, a food product, a medical food, an oral nutritional supplement, a nutritional composition, an oral cosmetics or a supplement to a food product and is preferably orally administered.
- a medical food product is specially formulated and intended for the dietary management of diseases or medical conditions (e.g., prevent or treat diseases or undesirable medical conditions).
- a medical food product can provide clinical nutrition, for example fulfilling special nutritional needs of patients with a medical condition or other persons with specific nutritional needs.
- a medical food product can be in the form of a complete meal, part of a meal, as a food additive, or a powder for dissolution.
- a food product, medical food or nutritional composition includes any number of optional additional ingredients, including conventional food additives, for example one or more proteins, carbohydrates, fats, acidulants, thickeners, buffers or agents for pH adjustment, chelating agents, colorants, emulsifiers, excipients, flavor agents, minerals, osmotic agents, a pharmaceutically acceptable carrier, preservatives, stabilizers, sugars, sweeteners, texturizers and/or vitamins.
- the optional ingredients can be added in any suitable amount.
- a food product, medical food or nutritional composition can be in any oral nutritional form, e.g. as a health drink, as a ready-made drink, optionally as a soft drink, including juices, milk-shake, yogurt drink, smoothie or soy-based drink, in a bar, or dispersed in foods of any sort, such as baked products, cereal bars, dairy bars, snack-foods, soups, breakfast cereals, muesli, candies, tabs, cookies, biscuits, crackers (such as a rice crackers), and dairy products.
- any oral nutritional form e.g. as a health drink, as a ready-made drink, optionally as a soft drink, including juices, milk-shake, yogurt drink, smoothie or soy-based drink, in a bar, or dispersed in foods of any sort, such as baked products, cereal bars, dairy bars, snack-foods, soups, breakfast cereals, muesli, candies, tabs, cookies, biscuits, crackers (such as a rice crackers), and dairy products
- a supplement may be in the form of tablets, capsules, pastilles or a liquid, for example.
- the supplement may further contain protective hydrocolloids (such as gums, proteins, modified starches), binders, film forming agents, encapsulating agents/materials, wall/shell materials, matrix compounds, coatings, emulsifiers, surface active agents, solubilizing agents (oils, fats, waxes, lecithins or the like), adsorbents, carriers, fillers, co-compounds, dispersing agents, wetting agents, processing aids (solvents), flowing agents, taste masking agents, weighting agents, jellifying agents and gel forming agents.
- protective hydrocolloids such as gums, proteins, modified starches
- binders film forming agents
- encapsulating agents/materials, wall/shell materials such as binders, film forming agents, encapsulating agents/materials, wall/shell materials, matrix compounds, coatings, emulsifiers, surface active agents, solub
- the supplement may also contain conventional pharmaceutical additives and adjuvants, excipients and diluents, including, but not limited to, water, gelatin of any origin, vegetable gums, ligninsulfonate, talc, sugars, starch, gum arabic, vegetable oils, polyalkylene glycols, flavoring agents, preservatives, stabilizers, emulsifying agents, buffers, lubricants, colorants, wetting agents, fillers, and the like.
- conventional pharmaceutical additives and adjuvants, excipients and diluents including, but not limited to, water, gelatin of any origin, vegetable gums, ligninsulfonate, talc, sugars, starch, gum arabic, vegetable oils, polyalkylene glycols, flavoring agents, preservatives, stabilizers, emulsifying agents, buffers, lubricants, colorants, wetting agents, fillers, and the like.
- the supplement can be added in a product acceptable to the consumer as an ingestible carrier or support.
- Such carriers or supports are a pharmaceutical, a food composition, and a pet food composition.
- Non-limiting examples for food and pet food compositions are milks, yogurts, curds, cheeses, fermented milks, milk-based fermented products, fermented cereal based products, milk-based powders, human milks, preterm formulas, infant formulas, oral supplements, and tube feedings.
- FIG. 3 shows a graph of energy expenditure as a function of time elapsed after ingestion of the various compounds.
- Fig. 4 shows a graph of energy expenditure based on AUC after ingestion of the various compounds. Figs. 3 and 4 demonstrate that energy expenditure is increased after cinnamaldehyde ingestion compared to placebo.
- Fig. 5 shows a graph of postprandial fat oxidation as a function of time elapsed after ingestion of the various compounds.
- Fig. 6 shows a graph of postprandial fat oxidation based on AUC after ingestion of various compounds. Figs. 5 and 6 demonstrate that postprandial fat oxidation is maintained at higher levels after cinnamaldehyde ingestion compared to placebo.
- Fig. 7 shows a graph of the nose temperature increases that were experienced after ingestion of the various compounds.
- Fig. 7 demonstrates that capsaicin and cinnamaldehyde increase nose temperatures for the fifteen minutes following ingestion, suggesting stimulation of the same autonomic thermoregulation pathway.
- Fig. 8 shows a graph and a table of the chin temperature, relative to baseline, as a function of time elapsed after ingestion of the various compounds.
- Fig. 8 demonstrates that cinnamaldehyde increases chin temperature for a prolonged time after ingestion, indicating increased blood flow, probably reflecting sympathetic autonomic activity.
- capsaicin and cinnamaldehyde might induce the same short term autonomic thermoregulation response by inducing a vasodilator reflex on the capillary of the nose.
- the increased sympathetic activity identified by measuring the facial temperature might explain the increased energy expenditure measured by indirect calorimetry.
- Fig. 9 shows a graph of the comparative taste testing results. 87.9% of the participants judged capsaicin intense to very intense, compared to only 20.5% for cinnamaldehyde.
- the dose of capsaicin is about 1.5 times less than the maximum that can be used as a flavor (7 ppm according to Fenaroli's Handbook), and the dose of cinnamaldehyde is about 17.5 times less than the maximum that can be used as a flavor (6191.0 ppm according to Fenaroli's Handbook).
Abstract
Description
Claims
Priority Applications (11)
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CA2929067A CA2929067C (en) | 2013-12-12 | 2014-12-12 | Methods and compositions for increasing energy expenditure using cinnamaldehyde |
US15/103,458 US10159653B2 (en) | 2013-12-12 | 2014-12-12 | Methods and compositions for increasing energy expenditure using cinnamaldehyde |
BR112016012233A BR112016012233A8 (en) | 2013-12-12 | 2014-12-12 | compositions comprising cinnamaldehyde, and its uses |
CN201480064893.4A CN105792819A (en) | 2013-12-12 | 2014-12-12 | Methods and compositions for increasing energy expenditure using cinnamaldehyde |
AU2014363403A AU2014363403A1 (en) | 2013-12-12 | 2014-12-12 | Methods and compositions for increasing energy expenditure using cinnamaldehyde |
CN202211653153.7A CN116077474A (en) | 2013-12-12 | 2014-12-12 | Methods and compositions for increasing energy expenditure using cinnamaldehyde |
EP14815643.3A EP3079678A1 (en) | 2013-12-12 | 2014-12-12 | Methods and compositions for increasing energy expenditure using cinnamaldehyde |
JP2016537463A JP6629732B2 (en) | 2013-12-12 | 2014-12-12 | Methods and compositions for increasing energy consumption using cinnamaldehyde |
AU2020202020A AU2020202020A1 (en) | 2013-12-12 | 2020-03-20 | Methods and compositions for increasing energy expenditure using cinnamaldehyde |
AU2021273560A AU2021273560A1 (en) | 2013-12-12 | 2021-11-24 | Methods and compositions for increasing energy expenditure using cinnamaldehyde |
AU2024200698A AU2024200698A1 (en) | 2013-12-12 | 2024-02-06 | Methods and compositions for increasing energy expenditure using cinnamaldehyde |
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US10548936B2 (en) * | 2017-04-27 | 2020-02-04 | Nanzheng Cheng | Method for reducing weight |
CN108713755A (en) * | 2018-06-07 | 2018-10-30 | 苟春虎 | Quinoa weight reducing nutrition milk shake |
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JP4742204B2 (en) | 2005-01-21 | 2011-08-10 | 財団法人ヒューマンサイエンス振興財団 | Adipocyte differentiation regulator |
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CA2929067C (en) | 2022-08-30 |
BR112016012233A8 (en) | 2021-06-29 |
AU2020202020A1 (en) | 2020-04-09 |
JP2017500301A (en) | 2017-01-05 |
BR112016012233A2 (en) | 2017-08-08 |
AU2021273560A1 (en) | 2021-12-16 |
AU2014363403A1 (en) | 2016-05-05 |
CN116077474A (en) | 2023-05-09 |
US10159653B2 (en) | 2018-12-25 |
CN105792819A (en) | 2016-07-20 |
CA2929067A1 (en) | 2015-06-18 |
EP3079678A1 (en) | 2016-10-19 |
JP6629732B2 (en) | 2020-01-15 |
US20160303055A1 (en) | 2016-10-20 |
AU2024200698A1 (en) | 2024-02-22 |
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