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WO2012150370A1 - Combinaison synergique de polyphénols - Google Patents

Combinaison synergique de polyphénols Download PDF

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Publication number
WO2012150370A1
WO2012150370A1 PCT/ES2012/070302 ES2012070302W WO2012150370A1 WO 2012150370 A1 WO2012150370 A1 WO 2012150370A1 ES 2012070302 W ES2012070302 W ES 2012070302W WO 2012150370 A1 WO2012150370 A1 WO 2012150370A1
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Prior art keywords
resveratrol
quercetin
catechin
extract
combination according
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Spanish (es)
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Jose Angel MARAÑON MAROTO
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SELECT BOTANICAL SL
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SELECT BOTANICAL SL
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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
    • A61K31/33—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 
    • 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
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • 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
    • A61K31/33—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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • 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)
    • A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
    • 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)
    • A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
    • A61K36/489—Sophora, e.g. necklacepod or mamani
    • 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)
    • A61K36/70—Polygonaceae (Buckwheat family), e.g. spineflower or dock
    • A61K36/704—Polygonum, e.g. knotweed
    • 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)
    • A61K36/87—Vitaceae or Ampelidaceae (Vine or Grape family), e.g. wine grapes, muscadine or peppervine
    • 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
    • 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
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • 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
    • 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
    • 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 polyphenol compositions that have a synergistic antioxidant power.
  • Free radicals are highly reactive molecules that are naturally generated in the tissues, and that can also be formed in an increased way due to environmental stress situations such as, for example, cigarette smoke, the presence of ionizing radiation, ultraviolet radiation, or environmental pollution, as well as other causes such as stress situations or the practice of a very intense exercise. Free radicals are capable of inducing the oxidation of nucleic acids, proteins and lipids of the organism, which can contribute to the acceleration of the aging process and trigger diseases associated with aging such as degenerative diseases, cancer, cardiovascular diseases and dermatological diseases.
  • Resveratrol is a polyphenolic compound present in the seed and in the skin of the grape (Vitis vinifera) and in other plant products. Its therapeutic interest has been reinforced since its possible involvement in the cardioprotective effects of red wine was postulated, as described in the article Siemann et al., Concentration of the phytoalexin resveratrol in wine, Am. J. Eno. Vitic, Free. Rad. Res., 1992, 43, 49-52, and its possible participation in the so-called French paradox: The French population, which has a diet rich in saturated fats, has a lower disease mortality rate cardiovascular than the rest of developed countries. This reduction was associated with the increased consumption of red wine and the presence of resveratrol in red wine.
  • LDL low density lipoproteins
  • the combination with quercetin may contribute to increasing the bioavailability of resveratrol, as described in the article De Santi et al., Sulphation of resveratrol, a natural compound present in wine, and its inhibition by natural flavonoids, Xenobiotica, 2000, 30 (9), 857-866.
  • compositions with resveratrol, catechin, epicatechin and quercetin are described, alone or in combination, for use as cardioprotectors, and their fibrinolytic activity is analyzed in an in vitro model with endothelial cells human derived from the umbilical vein (HUVEC) and in an in vivo model in rat.
  • the examples describe compositions in the form of capsules or orange juice in which resveratrol, quercetin and catechins are combined, in a weight ratio of 1: 2.5: 7.5, equivalent to a 1: 1 molar ratio , 9: 5.9.
  • dietary and cosmetic compositions are described with antioxidant properties comprising a skin extract, seeds and black grape rasp of the species Vitis vinifera containing polyphenols and anthocyanins.
  • polyphenols are catechin, gallic acid, quercetin, and resveratrol. It is described that said combination of polyphenols and anthocyanins has antioxidant properties, in the proportions in which it is obtained directly from the plant extract.
  • resveratrol, quercetin and catechin are in an approximate ratio of 1: 3: 21, equivalent to an approximate molar ratio of 1: 2.3: 16.5 .
  • the object of the invention is a synergistic combination of polyphenols.
  • a composition comprising said combination is also part of the object of the invention.
  • the combination for use as an antioxidant is also part of the invention.
  • the object of the present invention is a synergistic combination of polyphenols comprising resveratrol, quercetin and catechin, with a molar ratio between resveratrol, quercetin and catechin of about 1: 1: 2 or about 1: 1: 5.
  • the authors of this invention have developed a combination of the resveratrol, quercetin and catechin polyphenols in such proportions that, surprisingly, it has a synergistic antioxidant power.
  • the combination of antioxidants comprises resveratrol, quercetin and catechin in a 1: 1: 2 or 1: 1: 5 molar ratio.
  • the molar ratio is 1: 1: 2.
  • the molar ratio is 1: 1: 5.
  • the term “approximately” means, for the value "1" of the molar ratio, a variation between 0.9 and 1.1, preferably between 0.95 and 1.05; for the value "2" a variation between 1, 8 and 2.2, preferably between 1, 9 and 2.1; and for the value "5" a variation between 4.5 and 5.5, preferably between 4.75 and 5.25, and more preferably between 4.9 and 5.1.
  • dry extract means the resulting product after subjecting the plant extract to a drying process whereby substantially all of the water it contains is removed.
  • purified extract means an extract having a polyphenol content equal to or greater than 90% by weight On the dry extract.
  • resveratrol preferably equal to or greater than 95%, more preferably equal to or greater than 98%
  • quercetin preferably equal to or greater than 95% expressed as quercetin dihydrate, more preferably equal to or greater than 98%
  • catechin a catechin content expressed as catechin preferably equal to or greater than 80%, more preferably equal to or greater than 85%.
  • Antioxidants are substances that can protect cells against oxidation and the effects of free radicals, because they eliminate these radicals from the medium and because they inhibit oxidation by oxidizing themselves.
  • antioxidants are polyphenols, which are compounds widely distributed in the plant kingdom, and have an appropriate chemical structure to capture free radicals.
  • polyphenols incorporate more than one phenol group. Its property as an antioxidant comes from its great reactivity as electron donors and the ability of the radical formed to stabilize and delocalize the missing electron.
  • the main sources of polyphenols are red fruits, tea leaves, beer, grapes, wine, olive oil, chocolate, cocoa, nuts, and pomegranates, among others.
  • resveratrol refers to trans-resveratrol and cis-resveratrol interchangeably, and also includes the active ingredient and its possible hydrates and / or solvates.
  • Trans-resveratrol is the common name that designates 5 - [(1 £) -2- (4- hydroxyphenyl) ethenyl] -1,3-benzenediol, which can also be called 3,5,4'-trihydroxystilbene, and that It has the following structure:
  • Cis-resveratrol is the common name that designates 5 - [(1 Z) -2- (4- hydroxyphenyl) ethenyl] -1, 3-benzenediol, and has the double bond of the previous figure in cis position.
  • Trans-resveratrol is a phenolic compound found in nature, produced by various plants. For example, it is one of the constituents of the skin and the grape seed and, consequently, one of the components of wine, especially red wine.
  • Trans-resveratrol was first isolated in 1940 from the root of hellebore, as described in the article MJ Takaoka, Of the phenolic substances of white hellebore (Veratrum grandiflorum Loes, fil), J. Faculty Sci Hokkaido Imperial University, 1949, 3, 1-16.
  • Trans-resveratrol can be obtained as an extract from various plant species such as, for example, skin and grape seed ⁇ Vitis), blueberries (Vaccinium), Polygonum cuspidatum root, hops (Humulus lupulus), Cassia garrettiana , Cassia Quinquangulata, Gnetum klossii, Pterolobium hexapetallum, peanut (Arachis hypogaea), pistachio (Pistacia vera), rhubarb leaves and root (Rheum rhabarbarum and Rheum Rhaponticum), Bauhinia racemosa bark, Veratrum grandiflorum bark Veratrum formosanum root, eucalyptus, spruce and spruce, among others.
  • plant species such as, for example, skin and grape seed ⁇ Vitis), blueberries (Vaccinium), Polygonum cuspidatum root, hops (Humulus lupulus), Cassia garrettian
  • plant extracts with various trans-resveratrol contents can be found, reaching values greater than 95% on the dry extract.
  • Polygonum cuspidatum root extract of the company Select Botanical is a purified extract that has a maximum water content of 8% by weight, and whose dry extract has a trans-resveratrol content greater than 98%, determined by HPLC.
  • resveratrol contents that can be between 0.05% and 98% determined by HPLC.
  • the determination of resveratrol content by HPLC can be done, for example, as described in the article Kolouchová-Hanzl ⁇ ková et al., Rapid method for resveratrol determination by HPLC with electrochemical and UV detections in wines, Food Chem., 2004, 87 ( 1), 151-158.
  • trans-resveratrol can be obtained in substantially pure form through suppliers such as, for example, the Sigma-Aldrich company.
  • Trans-resveratrol can also be synthesized, for example as described in the article Fari ⁇ a et al., An improved synthesis of resveratrol, in Nat. Prod. Res., 2006, 20 (3), 247-52.
  • cis-resveratrol can be obtained, for example, from trans-resveratrol by exposure to ultraviolet radiation.
  • Transrosveratrol is preferably used in the combination of the invention.
  • resveratrol may be of synthetic or natural origin.
  • the source of resveratrol is a plant extract. More preferably as a source of resveratrol, an extract of plant origin with a high trans-resveratrol content is used, preferably greater than 95% on the dried extract, determined by HPLC, more preferably a Polygonum cuspidatum root extract, and even more preferably a purified extract of Polygonum cuspidatum root with a trans-resveratrol content greater than 98% on the dry extract, determined by HPLC. Quercetin
  • Quercetin or 2- (3,4-dihydroxyphenyl) -3,5,7-trihydroxy-4H-1-benzopyran-4- one is a polyphenol that structurally belongs to the flavonoid group and responds to the following formula:
  • Quercetin is widely distributed in nature, and is present in a variety of plants and fruits. Because of this, quercetin can be obtained as an extract, from various vegetables and fruits such as, for example, green tea and black tea (Camellia sinensis), capers, mountain celery (Levisticum officinale), apples, onion, black grape, citrus, papaya, tomato, broccoli, cauliflower, chili (Capsicum annum), blueberries, or Sophora japan, among others.
  • green tea and black tea Camellia sinensis
  • capers mountain celery
  • Amya tomato
  • broccoli cauliflower
  • chili Capsicum annum
  • Sophora japan among others.
  • Quercetin can be found commercially as an extract of plant origin with various contents, which may be greater than 98% on the dry extract, determined by HPLC, expressed as quercetin dihydrate.
  • the purified extract of acacia flowers from Japan or tree of pagodas (Sophora Japónica), from the Select Botanical company is presented in the form of a yellow powder containing quercetin in the form of quercetin dihydrate, with a content of water that is a maximum of 12.5%, and that has a minimum content of quercetin dihydrate of 98% on the dry extract, determined by HPLC, for example as described in the article Beecher et al., Analysis of tea polyphenols , Proc. Soc. Exp. Biol. Med., 1999, 220 (4), 267-70.
  • Quercetin is also found as an onion extract (Allium cepa) with varying concentrations between 0.5% and 40%, and as apple, asparagus and grape extracts.
  • Quercetin can also be obtained commercially in substantially pure form through suppliers such as Sigma-Aldrich.
  • quercetin can be synthesized, for example, as described in the article Shakhova et al., Zh. Obshch Khim., 1962, 32, 390.
  • quercetin is broadly understood and includes the active ingredient and its possible hydrates and / or solvates. In a preferred embodiment of this invention, quercetin is in the form of dihydrate.
  • quercetin may be of synthetic or natural origin.
  • the source of quercetin is a plant extract. More preferably, an extract of plant origin with a high quercetin content is used, such as for example greater than 95% on the dry extract expressed as quercetin dihydrate, and more preferably a japanic Sophora extract, and even more preferably a purified extract of Japan sophora with a content greater than 98% quercetin dihydrate on the dry extract.
  • Catechin is the common name by which it knows the product (2R, 3S) -2- (3,4-dihydroxyphenyl) -3,4-dihydro-2 / - / - chromen-3,5,7-triol, a polyphenol also belonging to the flavonoid group, and which has the following structure:
  • the catechin molecule has two asymmetric carbons or chiral centers in positions 2 and 3, as indicated in the previous structure and, therefore, there are actually four different stereoisomers: two of them in the cis configuration and two in the configuration trans.
  • the two trans forms correspond to the enantiomer (2R, 3S), represented in the above formula, and to the enantiomer (2S, 3R), in which the configuration of the two asymmetric carbons 2 and 3 is reversed.
  • epicatechin corresponds to the product (2R, 3R) -2- (3,4-dihydroxyphenyl) -3,4-dihydro-2H-chromen-3,5,7-triol, which has the following structure:
  • epicatechin is understood as the set formed by the two cis isomers, both the enantiomer (2R, 3R) represented above, and the corresponding enantiomer (2S, 3S), in which the configuration of the two asymmetric carbons 2 and 3.
  • Catechins are also found in nature in the form of dimers and trimers, which are known by the name of proanthocyanidins or procyanidins or oligomeric proanthocyanidins.
  • any of the 4 stereoisomers mentioned that is, both the catechin and the epicatechin and their respective enantiomers
  • catechin any of its possible dimers or trimers in the form of type B proanthocyanidins (dimers formed from catechin and / or epicatechin) or proanthocyanidins type C (trimer formed from epicatechin), dimer in the form of gallate, and any mixture of the above.
  • the source of catechin can be a plant extract with different contents in catechins, which can be equal to or greater than 90% on the dry extract expressed as catechin.
  • the purified extract of Vitis vinifera from the company Select Botanical which is presented in the form of an orange powder with a water content of at most 8% and with a catechin content of approximately 90% on the dry extract expressed as catechin, determined by spectrophotometry, for example as described in the article Peri et al., An Assay of Different Phenolic Fractions in Wines, Am. J. Enol. Vitic., 1971, 22 (2), 55-58.
  • Said extract contains a mixture of trans-catechin, epicatechin, dimer in the form of gallate, and proanthocyanidins.
  • Other sources of catechins are extracts from green tea, cocoa, green coffee and blueberries.
  • catechin (2S, 3R) -2- (3,4-dihydroxyphenyl) -3,4-dihydro-2H-chromen-3,5,7-triol is used in substantially pure form.
  • the catechin is the trans isomer, in any of its enantiomeric (2S, 3R) or (2R, 3S) forms, or a mixture of the two in any proportion, and optionally further containing epicatechin in any of its two enantiomeric forms and / or proanthocyanidins, or any mixture of the above in any proportion, preferably obtained from plant extracts.
  • the source of catechin is a grape extract, that is, an extract of Vitis vinifera preferably with a catechin content equal to or greater than 80% on the dry extract expressed as catechin, and even more preferably employs a purified extract of Vitis vinifera with a catechin content equal to or greater than 90% on the dry extract expressed as catechin.
  • plant extracts can be used as sources of antioxidants containing different resveratrol, quercetin, catechin, or extracts containing mixtures of two or more of these polyphenols.
  • a plant extract containing substantially pure resveratrol is used, that is, with a resveratrol content greater than 90% over the dry extract, preferably greater than 92%, more preferably greater than 95%, and even more preferably greater than 98% .
  • a plant extract containing substantially pure quercetin is used, that is, with a content greater than 90% on the dry extract, preferably greater than 92%, more preferably greater than 95%, and even more preferably greater than 98% expressed as Quercetin dihydrate
  • a plant extract containing substantially pure catechin is used, that is, with a catechin content greater than 80% over the dry extract, preferably greater than 85%, and more preferably greater than 90% expressed as catechin.
  • the combination of antioxidants comprises resveratrol, quercetin and catechin in a molar ratio resveratrol: quercetin: catechin of approximately 1: 1: 2,
  • the source of resveratrol is a root extract of Polygonum cuspidatum, preferably with a content of trans-resveratrol greater than 95% on the dry extract
  • the source of quercetin is an extract of Sophora japan, preferably with a content of quercetin dihydrate greater than 98% on the dry extract
  • the source of catechin is an extract of Vitis vinifera, preferably with a catechin content equal to or greater than 90% on the dry extract expressed as catechin.
  • the combination of antioxidants comprises resveratrol, quercetin and catechin in a molar ratio resveratrol: quercetin: catechin of approximately 1: 1: 5,
  • the source of resveratrol is a root extract of Polygonum cuspidatum, preferably with a content of trans-resveratrol greater than 95% on the dry extract
  • the source of quercetin is an extract of Sophora japan, preferably with a content of quercetin dihydrate greater than 98% on the dry extract
  • the source of catechin is an extract of Vitis vinifera, preferably with a catechin content equal to or greater than 90% on the dry extract expressed as catechin.
  • the combination of antioxidants consists essentially of resveratrol, quercetin and catechin in a molar ratio resveratrol: quercetin: catechin of approximately 1: 1: 2,
  • the source of resveratrol is a root extract of Polygonum cuspidatum, preferably with a content of trans-resveratrol greater than 95% on the dry extract
  • the source of quercetin is an extract of Sophora japan, preferably with a content of quercetin dihydrate greater than 98% on the dry extract
  • the source of catechin is a Vitis vin ⁇ fera extract, preferably with a catechin content equal to or greater than 90% on the dry extract, expressed as catechin.
  • the combination of antioxidants consists essentially of resveratrol, quercetin and catechin in a molar ratio resveratrol: quercetin: catechin of approximately 1: 1: 5,
  • the source of resveratrol is a root extract of Polygonum cuspidatum, preferably with a content of trans-resveratrol greater than 95% on the dry extract
  • the source of quercetin is an extract of Sophora japan, preferably with a content of quercetin dihydrate greater than 98% on the dry extract
  • the source of catechin is a Vitis vinifera extract, preferably with a catechin content equal to or greater than 90% on the dry extract expressed as catechin.
  • the antioxidant combination does not contain routine.
  • polyphenols consisting of trans-resveratrol, catechin ((2R, 3S) -2- (3,4-dihydroxyphenyl) -3,4-dihydro-2H-chromen-3,5,7-triol, its enantiomer or mixtures of both), epicatechin ((2R, 3R) -2- (3,4-dihydroxyphenyl) -3,4-dihydro-2H-chromen-3,5,7-triol, its enantiomer, or mixtures of both), Quercetin and rutin in a 1: 1: 1: 1 molar ratio, where each of the polyphenols have a chromatographic purity equal to or greater than 90%, such as those supplied by the Sigma-Aldrich company, is not part of the invention.
  • the antioxidant power of the compositions of the present invention can be determined using an in vitro method designed to assess the free radical scavenging capacity of the tested substances.
  • the method called TOSC (Total Oxidant Scavenging Capacity), which allows the determination of the antioxidant power of compounds at low concentrations.
  • the antioxidant power of a compound can be determined at a specific concentration, and it can be applied to both solutions with pure antioxidants and complex mixtures.
  • the ability of the substance to be tested to inhibit the oxidation of ⁇ -keto-Y-methylthiobutyric acid is determined by the action of free radicals such as, for example, hydroxyl (HO), peroxyl (ROO) or peroxynitrite (ONOO " ).
  • free radicals such as, for example, hydroxyl (HO), peroxyl (ROO) or peroxynitrite (ONOO " ).
  • H 3 CS-CH 2 -CH 2 -CO-COOH ⁇ H 2 C CH 2 + 1/2 (CH 3 -S) + C0 2
  • the TOSC test against peroxyl radicals was performed since they are more stable and have a longer half-life than hydroxyl radicals or peroxynitrite radicals.
  • Peroxyl radicals can be obtained by thermal decomposition and symmetric hydrolysis of the 2,2'-azobis (2-methylpropionamidine) compound (ABAP).
  • the antioxidant power of the tested substances can be measured by the ability to inhibit the formation of ethylene in the presence of peroxyl radicals compared to a control reaction, in which an antioxidant substance is not used as an inhibitor.
  • TOSC values are determined according to the methodology described in the articles Regoli et al., Quantification of total oxidant scavenging capacity of antioxidants for peroxynitrite, peroxyl radicáis, and hydroxyl radicáis, Toxicol. Appl. Pharm., 1999, 156, 96-105 and Regoli et al., Total oxidant scavenging capacity (TOSC) of microsomal and cytosolic fractions from Antarctic, Arctic and Mediterranean scallops: differentiation between three potent oxidants, Aquat. Toxicol., 2000, 49 (1-2), 13-25.
  • TOSC values are quantified by measuring ethylene formation, by comparison of the integrated areas for each tested substance and the control substance, according to the following equation:
  • Control substances without the ability to eliminate free radicals, have a TOSC value of 0%, since they have the same area under the curve as the control.
  • Compounds that completely prevent the formation of ethylene have an area under the curve equal to 0 and, therefore, a TOSC value of 100%.
  • composition comprising the combination of polyphenols of the invention and an acceptable vehicle.
  • the composition is selected from a pharmaceutical composition, a cosmetic composition, a food composition, a dietary supplement, and a veterinary composition, and the vehicle is respectively pharmaceutical, cosmetic, food, dietary, or veterinarily acceptable.
  • compositions suitable for incorporating the combination of polyphenols of the present invention can be formulated for oral, nasal, rectal, parenteral or topical administration.
  • solid and semi-solid pharmaceutical forms such as tablets, creams, hard capsules, soft capsules, dragees, powder presentations are suitable; such as liquid or semi-liquid, such as syrups or any type of aqueous, or non-aqueous solution, suspension or emulsion.
  • compositions are formulated according to the procedures that are known to the expert in pharmaceutical technology, as described, for example, in the book M. E. Aulton, Pharmacy. The science of the design of pharmaceutical forms, second edition, Elsevier, Madrid, 2004. For example, by mixing the antioxidant combination of the invention with at least one pharmaceutically acceptable carrier or excipient and, optionally, with one or more products with therapeutic or dietary functionalities, such as vitamins, minerals, trace elements and other micronutrients.
  • excipients suitable for use in the pharmaceutical compositions object of the present invention are well known to the expert in pharmaceutical technology and are described, for example, in the book R. C. Rowe, P. J. Sheskey and P.J. Weller, Handbook of Pharmaceutical Excipients, fourth edition, Pharmaceutical Press, 2003.
  • excipients and vehicles suitable for use in liquid formulations in the form of solutions, suspensions or emulsions, are, for example, solvents, buffers, viscosity modifiers, density modifiers, surfactants and emulsifiers, flocculating agents, humectants, preservatives, sweeteners and flavorings, and mixtures of the foregoing.
  • excipients and / or vehicles suitable for use in solid pharmaceutical compositions are, for example, fillers, binders, non-stick agents, lubricants, anti-caking agents, materials for the coating of tablets, gelatin for hard and soft capsules, plasticizers, stabilizers, preservatives, dyes, essences, and mixtures thereof.
  • the combination of polyphenols of the invention can also be incorporated into cosmetic compositions for external application, typically for hair or skin care.
  • Cosmetic forms suitable for incorporating the antioxidant combinations of the present invention are, for example, creams, gels, milks, lotions, sprayable emulsions, and solid bars, among others.
  • the cosmetic compositions are formulated according to the procedures that are known to the person skilled in the art, by mixing the combination of polyphenols of the invention with at least one cosmetically acceptable carrier in which it is dissolved, emulsified, dispersed, or it is suspended.
  • the vehicle is selected from water, a water miscible non-aqueous vehicle, such as ethanol or isopropanol, and a water non-water miscible vehicle, such as paraffin oil.
  • the cosmetic compositions may contain at least one additional cosmetic ingredient, which may be chosen, for example, from the group consisting of surfactants and emulsifiers, lipid compounds and emollients, consistency factors and thickeners, stabilizers, hydrotropes, preservatives, essences, colorants, silicone compounds, fats, waxes, lecithins, phospholipids, UV sun protection factors, film-forming agents, self tanners, or tyrosine inhibitors (depigmentation agents), or mixtures of the above.
  • additional cosmetic ingredient which may be chosen, for example, from the group consisting of surfactants and emulsifiers, lipid compounds and emollients, consistency factors and thickeners, stabilizers, hydrotropes, preservatives, essences, colorants, silicone compounds, fats, waxes, lecithins, phospholipids, UV sun protection factors, film-forming agents, self tanners, or tyrosine inhibitors (depigment
  • the combination of polyphenols of the present invention can be incorporated into food products and dietary supplements, for example in the form of nutraceutical products or functional foods or food supplements for sports nutrition.
  • any type of food composition or dietary supplement is suitable for incorporating the combination of polyphenols object of the invention, for example, infusions, coffees, drinks in general such as juices or other Alcoholic or non-alcoholic beverages, pastries or bakery products, jams, energy bars, cereals, flours, dairy products such as cheese, milk, butter, yogurts or cream, chocolate-based products and sweets such as candy, chewing gum or ice cream , oils, margarine, preserves.
  • the food product incorporating the combination of polyphenols of the invention may additionally contain other products with therapeutic or dietary functionalities, preferably, vitamins, minerals, trace elements or other micronutrients, or other plant extracts of polyphenols source.
  • the food product containing the combination of polyphenols of the invention may additionally contain one or more ingredients, which are chosen from among the usual authorized food additives, well known to those skilled in the art, for example of the type dyes, preservatives , condiments and spices, flavor enhancers, thickeners and gelling agents.
  • the combination of polyphenols of the invention can also be incorporated into veterinary compositions intended for animal feed, in particular for the feeding of domestic animals. Such combinations may be incorporated into pet food compositions, such as those described in patent applications EP-A-1514480 and WO-A-2005/1 10037, by methods well known to those skilled in the art. Applications
  • the composition is selected from the group consisting of a pharmaceutical composition, a cosmetic composition, a food composition, a dietary supplement, and a veterinary composition.
  • the combination of polyphenols object of the present invention can be used therapeutically to prevent or decrease the progression of all those pathological conditions that can be treated with antioxidants and / or free radical scavengers, such as cancer, cardiovascular diseases, inflammatory diseases, coronary diseases, diabetes, Alzheimer's disease, multiple sclerosis or dermatological conditions such as psoriasis or the appearance of eczema , among other.
  • pathological conditions such as cancer, cardiovascular diseases, inflammatory diseases, coronary diseases, diabetes, Alzheimer's disease, multiple sclerosis or dermatological conditions such as psoriasis or the appearance of eczema , among other.
  • the combination of the invention is particularly useful for delaying the symptoms of aging, for its ability to protect organs, tissues and cells against the harmful effects of oxidation. It is also appropriate, for example, to treat premature aging of the skin by preventing the breakdown of collagen fibers and, in general, all tissues.
  • the combination of the invention is also particularly suitable for those subjects most likely to generate free radicals in an increased manner in their organism, for example, smokers, people especially exposed to adverse conditions of environmental pollution, ionizing radiation, excessive sun exposure, subject people to stressful situations, or people who practice intense physical exercise.
  • Example 1 Preparation of an antioxidant composition of resveratrol
  • Quercetin and catechin in 1: 1: 2 molar ratio based on resveratrol and quercetin from vegetable extracts and catechin (2S.3R) In a container equipped with a mixer for solid products 253.16 g of purified extract of root of Polygonum cuspidatum with a water content of 8% and a 98% content of resveratrol on the dry extract, equivalent to 1 mol of resveratrol; 386.59 g of purified extract of Sophora japan with a water content of 12.5% and a content of 100% quercetin dihydrate on the dry extract, equivalent to 1 mol of quercetin; and 580.52 g of catechin (2S, 3R) substantially pure (Sigma), equivalent to 2 moles of catechin, and the whole was mixed until complete homogenization.
  • the antioxidant power of the compositions of the present invention was measured by the TOSC method, as described above. Solutions of concentration 1 ⁇ concentra Terms of the substances or mixtures to be tested were used, and distilled water as a control, whose TOSC value is 0%.
  • Resveratrol-quercetin-catechin R + Q + C ex tr (1: 1: 2): 0.5 ml of solution R, 0.5 ml of solution Q and 1 ml of solution C ex tr were taken , and mixed.
  • This solution contained a concentration of 0.25 ⁇ of resveratrol, 0.25 ⁇ of quercetin and 0.5 ⁇ of catechin.
  • the total concentration of polyphenols was 1 ⁇ .
  • This solution contained a concentration of 0.143 ⁇ of resveratrol, 0.143 ⁇ of quercetin and 0.714 ⁇ of catechin.
  • the total concentration of polyphenols was 1 ⁇ .
  • This solution contained a concentration of 0.25 ⁇ of resveratrol, 0.25 ⁇ of quercetin and 0.5 ⁇ of catechin.
  • the total concentration of polyphenols was 1 ⁇ .
  • This solution contained a concentration of 0.143 ⁇ of resveratrol, 0.143 ⁇ of quercetin and 0.714 ⁇ of catechin.
  • the total concentration of polyphenols was 1 ⁇ .
  • Ethylene formation during the TOSC test was monitored by gas chromatography, with HP 5890-series II equipment, HP Chemstation 5890 Software, and calculated by determining the area under the curve, using the SRI PeakSimple ® program . Linear regression was calculated using the GraphPad Prism ® program . The slope of the regression was calculated in the linear margin of the TOSC control curve versus the concentration of the assets tested.
  • TOSC calculated represents the TOSC value that theoretically corresponds to the samples of the different combinations of antioxidants taking into account only an additive effect of each of them.
  • the calculated value is obtained by multiplying the concentration of each of the antioxidants in the sample by the experimental TOSC of each of the individual antioxidants and dividing by the concentration of the antioxidant in the individual sample. For example in the case of sample 5:
  • the “Increment” column corresponds to the difference between the calculated and experimental TOSC value, and allows quantifying the synergistic effect observed in the antioxidant power of the combinations. It can be seen that the combination of resveratrol, quercetin and catechin of the invention, both in the 1: 1: 2 molar ratio, and in the 1: 1: 5 molar ratio, shows a remarkable synergistic effect. Likewise, it can be observed that, although the synergistic effect with pure catechin (2S, 3R) is slightly higher than that of catechin from grape extract, a comparable synergistic effect can be appreciated in both cases, independent of the source of Catechins used.
  • the "Potency” column reflects the number of times the antioxidant power increases with the combinations object of the invention compared to the antioxidant power obtained from the separate addition of the antioxidant powers of resveratrol, quercetin and catechin.
  • Example 4 Preparation of a food supplement for the prevention of skin aging
  • Example 5 Preparation of a food supplement for the improvement of the prevention of age-related macular degeneration
  • Soft gelatin capsules (14/16 oblong) of black color were prepared with the following filling per capsule:
  • Example 7 Preparation of a functional coffee-based food for the prevention of cardiovascular disease
  • Example 8 Preparation of a food supplement based on natural substances as an antioxidant in sports nutrition
  • Soft gelatin soft capsules (20 oblong) of purple color were prepared with the following filling per capsule:
  • Beta-carotene dunaliella (95% retinol) 30.00
  • Example 9 Preparation of a nutritional supplement for the improvement of the appearance of the skin and brightness of the fur in pets (mammals)
  • the molar ratio resveratrol: quercetin: catechin in this preparation is 1: 1: 5.09.
  • Example 10 Preparation of a nutritional supplement to improve the fertility of stallions (mammals)
  • Soft gelatin capsules (22 oblong) of red color were prepared with the following filling per capsule:

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Abstract

La présente invention concerne une combinaison des polyphénols resvératrol, quercétine et catéchine dans une relation molaire d'approximativement 1:1:2 ou bien d'approximativement 1:1:5, qui présente un pouvoir antioxydant synergique. Cette combinaison de polyphénols est appropriée pour être incorporée dans tout type de préparations pharmaceutiques, cosmétiques, alimentaires ou vétérinaires et peut être utilisée dans la prévention et le traitement de pathologies ou d'états physiologiques susceptibles d'être traités à l'aide de substances antioxydantes et de capture de radicaux libres.
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US10130574B2 (en) 2015-03-20 2018-11-20 Dow Global Technologies Llc Nitrone inhibition of oxidation of unsaturated fats
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ITMI20130397A1 (it) * 2013-03-15 2014-09-16 Giuliani Spa Composizione a base di flavonidi per uso farmaceutico, nutrizionale o cosmetico con potenziata azione antiossidante
EP3074028B1 (fr) * 2013-11-27 2022-04-06 Research Foundation Of The City University Of New York Compositions de curcumine à activité améliorée et méthodes d'utilisation
US9828335B2 (en) 2014-03-07 2017-11-28 Dow Global Technologies Llc Nitrone compounds and their use in personal care
US9701625B2 (en) 2014-03-07 2017-07-11 Dow Global Technologies Llc Nitrone compounds and their use in personal care
WO2015134688A1 (fr) 2014-03-07 2015-09-11 Dow Global Technologies Llc Composés nitrones et leur utilisation dans les soins personnels
US9730874B2 (en) 2014-05-12 2017-08-15 Dow Global Technologies Llc Nitrone compounds and their use in personal care
US9796667B2 (en) 2014-05-12 2017-10-24 Dow Global Technologies Llc Nitrone compounds and their use in personal care
WO2016003767A1 (fr) 2014-06-30 2016-01-07 Dow Global Technologies Llc Nitrones polymères et leur utilisation dans les soins d'hygiène personnelle
US10064804B2 (en) 2014-06-30 2018-09-04 Dow Global Technologies Llc Polymeric nitrones and their use in personal care
US10130574B2 (en) 2015-03-20 2018-11-20 Dow Global Technologies Llc Nitrone inhibition of oxidation of unsaturated fats
US10137071B2 (en) 2015-03-20 2018-11-27 Dow Global Technologies Llc Nitrone inhibition of oxidation of unsaturated fats
CN109982694A (zh) * 2016-09-27 2019-07-05 株式会社爱茉莉太平洋 增强小肠上皮细胞中儿茶素吸收的儿茶素吸收增强剂
US20190223486A1 (en) * 2016-09-27 2019-07-25 Amorepacific Corporation Catechin absorption enhancer for enhancing catechin absorption in small intestinal epithelial cells

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