WO2005004630A1 - Composition with antioxidant activity for pharmaceutical or dietary or cosmetic use - Google Patents
Composition with antioxidant activity for pharmaceutical or dietary or cosmetic use Download PDFInfo
- Publication number
- WO2005004630A1 WO2005004630A1 PCT/EP2004/007506 EP2004007506W WO2005004630A1 WO 2005004630 A1 WO2005004630 A1 WO 2005004630A1 EP 2004007506 W EP2004007506 W EP 2004007506W WO 2005004630 A1 WO2005004630 A1 WO 2005004630A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- caffeic acid
- catechin
- resveratrol
- molar ratio
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
-
- 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
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
Definitions
- the present invention relates to a composition with antioxidant activity for pharmaceutical or dietary or cosmetic use.
- red wine is associated with a reduction in the incidence of cardiovascular events (More, Medicine 1986:65:245-67; Graziano, N Engl J Med 1993:329:1829-34).
- Components of red wine such as flavonoids are thought to be beneficial to the cardiovascular system by virtue of their capacity to inhibit platelet function.
- composition with antioxidant activity for pharmaceutical or dietary or cosmetic use characterised by comprising as active principle a combination of the flavonoids catechin and quercetin, which exhibit synergistic activity, when associated in reciprocal molar ratios selected within a critical range, extending from 6:1 to 3:1 moles of catechin:quercetin.
- Oxidative stress favours numerous pathologies. It is also noted that there are various pathological conditions in the pathogenesis of which oxidative stress appears to play an important role. Oxidative events are particularly notable in various conditions such as: hypoxia, inflammation, irradiation by ultraviolet light, alcohol abuse, ageing.
- oxidative stress is implicated: atherosclerosis, ischemic cardiopathy, cerebral vascular insufficiency, complications of diabetes, hypertension, nephropathy, retinopathy, cataracts, chronic hepatopathies, neurodegenerative pathologies (Alzheimer, Parkinson), tumours, immunodeficiencies, chronic colitises.
- the present invention proposes as its object the prevention and treatment of oxidative stress in general and of all consequent pathologies, in particular chronic inflammatory pathologies and cardiovascular diseases.
- a selected combination of the three flavonoids resveratrol, catechin and caffeic acid is able to develop antioxidant activity with synergistic action.
- the invention provides a composition with antioxidant activity for pharmaceutical or dietary or cosmetic use, characterised by comprising as active principle a combination of resveratrol, catechin and caffeic acid.
- the molar ratio of caffeic acid to catechin is preferably within the range from about 1 :2 to 1 :6, respectively.
- the molar ratio of caffeic acid to catechin is about 1 :4, respectively.
- the molar ratio of resveratrol to caffeic acid in the composition of the invention is preferably within the range from about 1 :3 to 1 :9, respectively.
- the molar ratio of resveratrol to caffeic acid is about 1 :6, respectively.
- the invention here described has its origin in experimental observations gained by a study, hereinafter reported as an example to better describe the action of said active principle and in no way limiting the scope of the invention, conducted with the initial aim of investigating if a moderate daily consumption of wine influences oxidative stress and platelet function.
- Study plan 20 healthy volunteers not presenting signs of cardiovascular diseases and without risk factors for atherosclerosis such as hypertension, diabetes, dyslipidemia, obesity, or a smoking habit, were examined.
- a bottle of wine (750 ml) was delivered to each subject every two days and the amount remaining in each bottle was measured to verify compliance.
- One of the subjects randomly assigned to the white wine group followed the protocol for two weeks but then refused to return for testing for blood changes.
- the laboratory study consisted of measuring the latent period of collagen-induced platelet aggregation, collagen- induced H 2 0 2 formation and plasma flavonoid concentration.
- the platelet suspension (2 x 10 8 cells/ml) was incubated (15 minutes at 37°C) with DCFH-DA (40 ⁇ mol/L) and activated with 2 ⁇ g/ml of collagen.
- the reaction was interrupted after one minute with EGTA 2mmol/L All the samples were analysed using a Coulter XL-MCL flow cytometer (Hialeah, USA) equipped with an argon laser (480 nm emission).
- the instrument was calibrated for measuring logarithmic forward light scatter (LFS) which is a measure of particle size, logarithmic 90° light scatter (LSS) which is a measure of cell granularity, and green fluorescence (DCF) at 510-550 nm (LFL1).
- LFS logarithmic forward light scatter
- LSS logarithmic 90° light scatter
- DCF green fluorescence
- I.S. intensity of mean channel fluorescence of stimulated platelets/ intensity of mean channel fluorescence of non-stimulated platelets.
- the fluorescence parameters were expressed as arbitrary units (a.u.) Aggregation test
- the latent period of collagen-induced platelet aggregation was evaluated by measuring the time delay between adding the agonist and the start of platelet aggregation. The determination was calculated with a specific aggregometer (Helena Laboratories: Beaumont, Texas).
- the platelets in the in-vitro study (2 x 10 8 cells/ml) were pre-incubated in either the presence of catechin (0.2 ⁇ M), caffeic acid (0.2 ⁇ M) and resveratrol (0.5 ⁇ M), used either individually or together (30 minutes at 37°C for each incubation) before activation with collagen (2 ⁇ g/ml), or in their absence.
- catechin 0.2 ⁇ M
- caffeic acid 0.2 ⁇ M
- resveratrol 0.5 ⁇ M
- Methanol and ethyl acetate were of HPLC grade and were acquired from Carlo Erba (Milan, Italy).
- the plasma samples were incubated with a hydrolysing solution to obtain free phenolic compounds. Briefly: 1.5 ml of plasma were mixed with 2 ml 100 mM acetate butter (pH 5.0) containing 4,000 units of glucuronidase plus 200 units of sulfatase. The mixture was incubated for 1 hour at 37°C and then extracted three times with ethyl acetate; 3.0 ml of ethyl acetate were added each time and the mixture was agitated for 4 minutes. After having centrifuged the mixture for 5 minutes at 3,500 r.p.m., the upper layers were removed. The combined extracts were made to pass through anhydrous sodium sulphate and dried under nitrogen. The samples were conserved at -70°C until required. Configuration and HPLC analysis
- the HPLC system was formed from a Perkin Elmer series 410 Lc pump with a SEC-4 control element for the gradient elution.
- the mobile phase was formed from two solutions: solution A was 0.22 M acetic acid, solution B was methanol.
- a binary gradient (between 7 and 24%) was applied, at a flow rate of 1 ml/min, to a Wakosil II 5C18 RS analytical column (5 ⁇ m, 150 x 4.6 mm internal diameter, SGE) equipped with a 10 mm SGE pre-column and maintained at 30°C.
- the plasma extracts were re-dissolved just before the analysis in methanol and 20 ⁇ L were injected into the system.
- the eluate was monitored with a Coulochem II electrochemical detector (ESA, Bedford, MA, USA) equipped with a model 5011 analytical cell.
- ESA Coulochem II electrochemical detector
- the settings were the following: the first electrode was set at -100 mV and the second electrode (the analytical electrode) at +600 mV.
- the detector output was recorded on a Perkin Elmer Turbochrom Chromatography workstation. The detection limit of the procedure was ⁇ 0.2 ngr/ml.
- Plasma ethanol was not detectable either before or after red or white wine consumption.
- the attached figures 1 and 2 show, respectively, the latent period of platelet aggregation and formation of collagen-induced platelet H 2 O 2 (administered at a concentration of 2 ⁇ g/ml), for the three flavonoids resveratrol, caffeic acid and catechin, both individually and in combination (mix), at the concentrations specified therein: catechin (0.2 ⁇ M), caffeic acid (0.2 ⁇ M) and resveratrol (0.5 ⁇ M), in both cases referred to a control.
- a synergistic antioxidant action by the three selected flavonoids in combination can therefore be deduced.
- Said selective combination of the present invention is indicated for use as active principle for: atherosclerosis, ischemic cardiopathy, cerebral vascular insufficiency, complications of diabetes, hypertension, nephropathy, retinopathy, cataracts, chronic hepatopathies, neurodegenerative pathologies (Alzheimer, Parkinson) tumours, immunodeficiencies, chronic colitises.
- the active principle proposed by the present invention can be conveniently formulated in compositions in which catechin is preferably present in a quantity between 1.5 and 30.0 mg/dose, caffeic acid from 1.25 to 5.0 mg/dose and resveratrol from 0.25 to 9.0 mg/dose.
- Crodasoft quaternium-9 cetrimonium methosulfate cetearyl alcohol
- Emulium 22 tribehenin PEG-20 esters octyldodecyl myristate 2 g
- Cannabis sativa oil 0.25 g
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT001396A ITMI20031396A1 (it) | 2003-07-09 | 2003-07-09 | Composizione per uso farmaceutico o dietetico o cosmetico dotata di attivita' antiossidante. |
ITMI2003A001396 | 2003-07-09 |
Publications (1)
Publication Number | Publication Date |
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WO2005004630A1 true WO2005004630A1 (en) | 2005-01-20 |
Family
ID=34044544
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2004/007506 WO2005004630A1 (en) | 2003-07-09 | 2004-07-08 | Composition with antioxidant activity for pharmaceutical or dietary or cosmetic use |
Country Status (2)
Country | Link |
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IT (1) | ITMI20031396A1 (it) |
WO (1) | WO2005004630A1 (it) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007042272A2 (en) * | 2005-10-14 | 2007-04-19 | Dsm Ip Assets B.V. | Use of a nutraceutical composition comprising resveratrol for the treatment of age-related diseases |
WO2007104867A2 (fr) * | 2006-03-16 | 2007-09-20 | Af Consulting | Compositions cosmetiques, pharmaceutiques, alimentaires et veterinaires dont l'action d'activation des genes de type sirtuin permet de retarder le vieillissement des mammiferes et ses effets nefastes |
WO2007121845A1 (de) * | 2006-04-25 | 2007-11-01 | Merck Patent Gmbh | Antioxidantien |
EP1904070A1 (en) * | 2005-07-07 | 2008-04-02 | H3 Formulations Ltd. | Dietary supplement for enhancing skeletal muscle mass, decreasing muscle protein degradation, downregulation of muscle catabolism pathways, and decreasing catabolism of muscle cells |
WO2009132888A1 (en) * | 2008-04-30 | 2009-11-05 | Nestec S.A. | Coffee extract |
WO2010062835A1 (en) * | 2008-11-26 | 2010-06-03 | Perio Sciences, Llc | Antioxidant compositions for soft oral tissue and methods of formulation and use there |
ITMI20091940A1 (it) * | 2009-11-05 | 2011-05-06 | Functional Point S R L | Composizione comprendente resveratrolo e almeno un polifenolo del vino rosso e suoi usi. |
US8012513B2 (en) | 2006-06-08 | 2011-09-06 | The Procter & Gamble Company | Method for promoting eye health |
EP2420289A1 (en) | 2010-08-18 | 2012-02-22 | Grindeks, a joint stock company | Composition of caffeic acid phenethyl ester (CAPE) and one of catechin, kaempherol and myricetin for potentiating antitumour effect and for treating tumours |
WO2012150370A1 (es) * | 2011-05-04 | 2012-11-08 | Select Botanical, S.L. | Combinación sinérgica de polifenoles |
WO2013054304A1 (fr) * | 2011-10-14 | 2013-04-18 | Laboratoires Inneov | Utilisation d'une composition orale comprenant un mélange d'au moins un polyphénol, de zinc, et de vitamine c. |
WO2014083172A1 (en) * | 2012-11-29 | 2014-06-05 | Nestec S.A. | Increasing the bioavailability of flavan-3-ols by polyphenols |
WO2014083161A1 (en) * | 2012-11-29 | 2014-06-05 | Nestec S.A. | Increasing the bioavailability of flavan-3-ols with carbohydrates with a low glycemic index |
US20160067296A1 (en) * | 2013-06-17 | 2016-03-10 | Unigen, Inc. | Compositions and Methods for Joint Health |
EP2906037A4 (en) * | 2012-10-12 | 2016-04-27 | Oréal L | COSMETIC COMPOSITIONS CONTAINING AT LEAST ONE FLAVONOID AND FERULIC ACID |
US9421180B2 (en) | 2011-09-30 | 2016-08-23 | Perio Sciences, Llc | Antioxidant compositions for treatment of inflammation or oxidative damage |
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US6238673B1 (en) * | 1996-09-20 | 2001-05-29 | The Howard Foundation | Method of producing high flavonol content polyphenol compositions |
WO2001060179A1 (en) * | 2000-02-16 | 2001-08-23 | Alan Norman Howard | Improvements in or relating to solubilisation of flavonols |
JP2001278723A (ja) * | 2000-03-28 | 2001-10-10 | Tokachi Nogyo Kyodo Kumiai Rengokai | そうか病防除資材 |
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2003
- 2003-07-09 IT IT001396A patent/ITMI20031396A1/it unknown
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2004
- 2004-07-08 WO PCT/EP2004/007506 patent/WO2005004630A1/en active Search and Examination
Patent Citations (3)
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US6238673B1 (en) * | 1996-09-20 | 2001-05-29 | The Howard Foundation | Method of producing high flavonol content polyphenol compositions |
WO2001060179A1 (en) * | 2000-02-16 | 2001-08-23 | Alan Norman Howard | Improvements in or relating to solubilisation of flavonols |
JP2001278723A (ja) * | 2000-03-28 | 2001-10-10 | Tokachi Nogyo Kyodo Kumiai Rengokai | そうか病防除資材 |
Non-Patent Citations (3)
Title |
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DATABASE WPI Section Ch Week 200211, Derwent World Patents Index; Class C03, AN 2002-078522, XP002264931 * |
FRANKEL E N ET AL: "PRINCIPAL PHENOLIC PHYTOCHEMICALS IN SELECTED CALIFORNIA WINES AND THEIR ANTIOXIDANT ACTIVITY IN INHIBITING OXIDATION OF HUMAN LOW-DENSITY LIPOPROTEINS", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 43, no. 4, 1995, pages 890 - 894, XP000497580, ISSN: 0021-8561 * |
SOLEAS G J ET AL: "RELATIVE CONTRIBUTIONS OF POLYPHENOLIC CONSTITUENTS TO THE ANTIOXIDANT STATUS OF WINES: DEVELOPMENT OF A PREDICTIVE MODEL", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 45, no. 10, 1 October 1997 (1997-10-01), pages 3995 - 4003, XP000701988, ISSN: 0021-8561 * |
Cited By (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1904070A1 (en) * | 2005-07-07 | 2008-04-02 | H3 Formulations Ltd. | Dietary supplement for enhancing skeletal muscle mass, decreasing muscle protein degradation, downregulation of muscle catabolism pathways, and decreasing catabolism of muscle cells |
EP1904070A4 (en) * | 2005-07-07 | 2009-09-02 | H3 Formulations Ltd | NUTRITIONAL SUPPLEMENT FOR IMPROVING SKELETAL MUSHROOMS, REDUCING MUSCLE PROTEIN DEGRADATION, DOWNGRADING MUSCLE CATABOLISM PATHS, AND REDUCING CATABOLISM OF MUSCLE CELLS |
WO2007042272A2 (en) * | 2005-10-14 | 2007-04-19 | Dsm Ip Assets B.V. | Use of a nutraceutical composition comprising resveratrol for the treatment of age-related diseases |
JP2009511523A (ja) * | 2005-10-14 | 2009-03-19 | ディーエスエム アイピー アセッツ ビー.ブイ. | レスベラトロールを含むニュートラシューティカル組成物の新規な使用 |
WO2007042272A3 (en) * | 2005-10-14 | 2008-09-25 | Dsm Ip Assets Bv | Use of a nutraceutical composition comprising resveratrol for the treatment of age-related diseases |
WO2007104867A3 (fr) * | 2006-03-16 | 2007-11-15 | Af Consulting | Compositions cosmetiques, pharmaceutiques, alimentaires et veterinaires dont l'action d'activation des genes de type sirtuin permet de retarder le vieillissement des mammiferes et ses effets nefastes |
FR2898493A1 (fr) * | 2006-03-16 | 2007-09-21 | Af Consulting | Compositions cosmetiques, pharmaceutiques, alimentaires et veterinaires dont l'action d'activation de genes de type sirtuin permet de retarder le vieillissement des mammiferes et ses effets nefastes |
WO2007104867A2 (fr) * | 2006-03-16 | 2007-09-20 | Af Consulting | Compositions cosmetiques, pharmaceutiques, alimentaires et veterinaires dont l'action d'activation des genes de type sirtuin permet de retarder le vieillissement des mammiferes et ses effets nefastes |
WO2007121845A1 (de) * | 2006-04-25 | 2007-11-01 | Merck Patent Gmbh | Antioxidantien |
JP2009534433A (ja) * | 2006-04-25 | 2009-09-24 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 酸化防止剤 |
US7906684B2 (en) | 2006-04-25 | 2011-03-15 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Antioxidants |
US8389028B2 (en) | 2006-06-08 | 2013-03-05 | The Iams Company | Method for promoting eye health |
US8012513B2 (en) | 2006-06-08 | 2011-09-06 | The Procter & Gamble Company | Method for promoting eye health |
US8691296B2 (en) | 2006-06-08 | 2014-04-08 | The Iams Company | Method for improving eye health |
WO2009132888A1 (en) * | 2008-04-30 | 2009-11-05 | Nestec S.A. | Coffee extract |
WO2010062835A1 (en) * | 2008-11-26 | 2010-06-03 | Perio Sciences, Llc | Antioxidant compositions for soft oral tissue and methods of formulation and use there |
AU2009319881C1 (en) * | 2008-11-26 | 2015-12-24 | Perio Sciences, Llc | Antioxidant compositions for soft oral tissue and methods of formulation and use thereof |
AU2009319881B2 (en) * | 2008-11-26 | 2015-10-01 | Perio Sciences, Llc | Antioxidant compositions for soft oral tissue and methods of formulation and use thereof |
WO2011055222A3 (en) * | 2009-11-05 | 2012-06-14 | Functional Point S.R.L. | Composition comprising an extract from polygonum cuspidatum and a polyphenolic extract from red vitis vinifera |
ITMI20091940A1 (it) * | 2009-11-05 | 2011-05-06 | Functional Point S R L | Composizione comprendente resveratrolo e almeno un polifenolo del vino rosso e suoi usi. |
EP2420289A1 (en) | 2010-08-18 | 2012-02-22 | Grindeks, a joint stock company | Composition of caffeic acid phenethyl ester (CAPE) and one of catechin, kaempherol and myricetin for potentiating antitumour effect and for treating tumours |
WO2012150370A1 (es) * | 2011-05-04 | 2012-11-08 | Select Botanical, S.L. | Combinación sinérgica de polifenoles |
US10918613B2 (en) | 2011-09-30 | 2021-02-16 | Perio Sciences, Llc | Antioxidant compositions for treatment of inflammation or oxidative damage |
US9421180B2 (en) | 2011-09-30 | 2016-08-23 | Perio Sciences, Llc | Antioxidant compositions for treatment of inflammation or oxidative damage |
FR2981272A1 (fr) * | 2011-10-14 | 2013-04-19 | Inneov Lab | Utilisation d'une composition orale comprenant un melange d'au moins un polyphenol, de zinc, et de vitamine c. |
WO2013054304A1 (fr) * | 2011-10-14 | 2013-04-18 | Laboratoires Inneov | Utilisation d'une composition orale comprenant un mélange d'au moins un polyphénol, de zinc, et de vitamine c. |
EP2906037A4 (en) * | 2012-10-12 | 2016-04-27 | Oréal L | COSMETIC COMPOSITIONS CONTAINING AT LEAST ONE FLAVONOID AND FERULIC ACID |
WO2014083172A1 (en) * | 2012-11-29 | 2014-06-05 | Nestec S.A. | Increasing the bioavailability of flavan-3-ols by polyphenols |
JP2016510307A (ja) * | 2012-11-29 | 2016-04-07 | ネステク ソシエテ アノニム | 低血糖指数を有する炭水化物によるフラバン−3−オールのバイオアベイラビリティの増大 |
CN104812253A (zh) * | 2012-11-29 | 2015-07-29 | 雀巢产品技术援助有限公司 | 用具有低血糖指数的碳水化合物增加黄烷-3-醇的生物利用度 |
US10709159B2 (en) | 2012-11-29 | 2020-07-14 | Societe Des Produits Nestle S.A. | Increasing the bioavailability of flavan-3-ols with carbohydrates with a low glycemic index |
US10722584B2 (en) | 2012-11-29 | 2020-07-28 | Societe Des Produits Nestle S.A. | Increasing the bioavailability of flavan-3-ols by polyphenols |
WO2014083161A1 (en) * | 2012-11-29 | 2014-06-05 | Nestec S.A. | Increasing the bioavailability of flavan-3-ols with carbohydrates with a low glycemic index |
US20160067296A1 (en) * | 2013-06-17 | 2016-03-10 | Unigen, Inc. | Compositions and Methods for Joint Health |
Also Published As
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ITMI20031396A1 (it) | 2005-01-10 |
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