WO2002034073A2 - Compositions contenant des flavonoides et de la phloridzine ou de la phloretine - Google Patents

Compositions contenant des flavonoides et de la phloridzine ou de la phloretine Download PDF

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Publication number
WO2002034073A2
WO2002034073A2 PCT/EP2001/012378 EP0112378W WO0234073A2 WO 2002034073 A2 WO2002034073 A2 WO 2002034073A2 EP 0112378 W EP0112378 W EP 0112378W WO 0234073 A2 WO0234073 A2 WO 0234073A2
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WO
WIPO (PCT)
Prior art keywords
food
animal feed
phloretin
flavonoid
phloridzin
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PCT/EP2001/012378
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German (de)
English (en)
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WO2002034073A3 (fr
Inventor
Peter Fürst
Original Assignee
Fuerst Peter
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Publication date
Application filed by Fuerst Peter filed Critical Fuerst Peter
Priority to AU2002224796A priority Critical patent/AU2002224796A1/en
Publication of WO2002034073A2 publication Critical patent/WO2002034073A2/fr
Publication of WO2002034073A3 publication Critical patent/WO2002034073A3/fr

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Classifications

    • 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
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/111—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/116—Heterocyclic compounds
    • A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/163—Sugars; Polysaccharides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT 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
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7032—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a polyol, i.e. compounds having two or more free or esterified hydroxy groups, including the hydroxy group involved in the glycosidic linkage, e.g. monoglucosyldiacylglycerides, lactobionic acid, gangliosides

Definitions

  • the present invention relates to compositions containing flavonoids and phloridzine and or phloretin and their use in particular in food preparations or food supplements and as an active principle in pharmaceutical preparations.
  • Hormones such as those formed in the ovaries, influence the development of breast and prostate cancer.
  • High concentrations of estrogens in the circulation and their detection in the urine in high concentrations are regarded as markers for an increased probability of illness.
  • soybean food reduces the incidence of breast and prostate cancer, including is associated with the fact that soybeans contain flavonoids, in particular isoflavones or flavones, which have a weakly estrogenic and an anti-carcinogenic effect. Flavonoids have been shown to significantly decrease serum 17ß-estradiol levels. They compete with endogenous estrogens for receptor binding and the estrogen-induced stimulation of breast cell proliferation is reduced. Furthermore, certain enzyme-dependent processes during tumor growth and its recurrence are influenced. Based on these findings, flavonoids have been proposed for the prevention of hormone-dependent cancers. Antiarteriosclerotic, antithrombotic, blood glucose regulating and antioxidative effects have also been described for flavonoids.
  • Flavonoids which are found in all higher plants, are phenylpropane derivatives with the Cl5 basic structure of flavans. They are predominantly in glycosidated form and are often esterified with aliphatic and / or aromatic acids. Non-glycosidated lipophilic forms occur as non-volatile components in essential oils.
  • the aglyka of flavonoids are divided into the following classes: anthocyanidins, aurones, catechins, chalcones, Deoxanthocyanidins, flavanols, flavanones, flavonols, flavones, isoflavones or leukoanthocyanidins.
  • the biflavonoids composed of two flavonoid units are also widespread.
  • the representatives of the flavonoid classes differ in the number of hydroxy and methoxy substituents.
  • the individual flavonoids also differ in the type and number of non-acylated and acylated sugar residues. More than 5000 flavonoid structures have been described.
  • Flavonoids are synthesized in plants from chalcon:
  • Isoflavones are usually yellowish-colored plant substances that are derived from isoflavone.
  • Flavones are also usually colored yellow.
  • the hydroxyl groups of the flavones are often linked to glucose and / or rhamnose or rare sugars. These hydroxyl groups mostly occur in the 3, 5 and 7 and 3 'and 4' positions.
  • flavonoids The most important source of flavonoids in human nutrition is soybeans, although legumes contain beans, peas, lentils and Peanuts, which are part of the so-called "western diet", also have significant amounts of flavonoids.
  • Phloridzine is a dihydrochalcone that is known to specifically inhibit the intestinal sodium-dependent glucose transporter SGLTl. This transport protein has been reported to accept various phenolic monoglucoside conjugates as a substrate. In the body, phloridzine is partly converted into its aglycone phloretin, which also inhibits the SGLTl transporter. Both phloridzin and phloretin can be used for the purposes of the present invention.
  • This composition is said to be Food preparation or food supplements can be used, or generally serve as part of a pharmaceutical preparation.
  • compositions according to the invention should themselves contain flavonoids in order to compensate for any flavonoid deficiency in the diet.
  • compositions which contain both flavonoids and phloridzin or phloretin.
  • the present invention thus relates to compositions for food preparations or food supplements for promoting flavonoid uptake in the intestine, containing a flavonoid and phloridzin and / or phloretin.
  • these are mixtures of foods known per se, but are mixed in such a way that the quantitative ratios preferred according to the invention Flavonoid / Phloridzin can be achieved.
  • the preferred proportions according to the invention in the mixture are: 1 part flavonoid to 0.01-50 parts phloridzine, preferably 1 part flavonoid to 0.1-50 parts phloridzin and particularly preferably 1 part flavonoid to 1-50 parts Phloridzin and very particularly preferably 1 part of flavonoid to 10-50 parts of phloridzin.
  • Another object of the present invention are pharmaceutical compositions containing a flavonoid and phloridzine for the manufacture of a medicament for the treatment and or prevention of diseases which can be favorably influenced by increased flavonoid uptake.
  • diseases are hormone-dependent cancers such as cervical or breast cancer, but also other types of cancer.
  • Other diseases that can be treated with the compositions according to the invention are arteriosclerotic and thrombotic degeneration as well as diseases related to regulation disorders of the blood glucose content.
  • the antioxidant effects of flavonoids can also be used to treat and prevent certain diseases.
  • these compositions serve to prevent and prevent or alleviate the symptoms which occur in the menopause of women, triggered by a reduced hormone level
  • compositions for food preparations includes both solutions, solubilisates and dispersions, such as
  • Preferred compositions are dispersions such as emulsions and suspensions, in particular oil-containing suspensions.
  • the content of flavonoid (s) and phloridzin, in the form of the combination according to the invention, in the compositions is generally between 0.1 and 100% by weight, preferably between 5 and 35% by weight, particularly preferably between 10 and 33% by weight .-%, and very particularly preferably between 15 and 32 wt .-% based on the total amount of the composition.
  • mixtures of the pure substances can also be used.
  • the flavonoids used for the preparation of the compositions and the phloridzine and / or phloretin are preferably used in the form of the commercially available amorphous powder in a purity of greater than 75%, preferably greater than 90%, particularly preferably greater than 95%, and very particularly preferably greater than 98% ,
  • the flavonoids and the phloridzine and / or phloretin can either originate from natural sources or be produced synthetically.
  • Genistin, Phloretin or Phloridzin can be obtained from EXTRASYNTHASE (Genay, France).
  • Genistein, phloretin or phloridzin can be obtained, for example, from SIGMA-ALDRICH (Deisenhofen, Germany).
  • Flavonoids which can be used according to the invention are, among others, preferably flavones and isoflavones, particularly preferably isoflavones.
  • flavones which can be used according to the invention are: flavonol, chrysin, galangin, apigenin, fisetin, luteolin, camphor oil, quercetin, morin, robinetin, gossypetin, myricetin.
  • isoflavones which can be used according to the invention are: daidzein, genistin, prunetin, biochanin A, Orobol, Santal, prateness. Table 1 Examples of flavones
  • Flavonoids which can be used according to the invention in particular flavones and isoflavones, can in each case be added via the OH groups shown above, for example with sugars such as hexoses and pentoses, for example glucose, galactose or Fructose be esterified. Esters with aliphatic or aromatic acids such as caffeic acid or malonic acid have also been described.
  • compositions characterized in that they comprise a flavonoid of the structural formula I and / or II, characterized in that R 2 , R 5 , R 6 , R 7 , R 8J R 2 >, R 3 ., R 4 -, R 5 . and R 6 . each independently represent H, OH, CH 3 , OCH 3 , a glycosidically linked sugar, particularly preferably hexose or pyranose, very particularly preferably glucose, galactose or rhamnose.
  • R 2 , R 5 , R 6 , R 7 , R 8J R 2 >, R 3 ., R 4 -, R 5 . and R 6 . each independently represent H, OH, CH 3 , OCH 3 , a glycosidically linked sugar, particularly preferably hexose or pyranose, very particularly preferably glucose, galactose or rhamnose.
  • all flavonoid analogs are included.
  • compositions are used as food preparations or food supplements.
  • preparations are used in the manufacturing process of the corresponding food or added to the end product.
  • the composition mentioned above is passed on directly to the consumer, for example in tablets or drink powder (effervescent) form.
  • concentration of the flavonoids in the finished food should be chosen so that there is a concentration of free flavonoid in the intestine of about 1-100 ⁇ M, preferably 1-50 ⁇ M and particularly preferably 20-30 ⁇ M.
  • the concentration of phloridzin phloretin in the finished food should be chosen so that there is a concentration of free phloridzin / phloretin in the intestine of about 1-100 mM, preferably 1-50 mM and particularly preferably 20-30 mM.
  • the preparations according to the invention can also contain other auxiliaries and additives in addition to the flavonoids and the phloridzin and / or phloretin.
  • auxiliaries and additives in addition to the flavonoids and the phloridzin and / or phloretin. Examples of this would be oils, protective colloids, plasticizers, antioxidants and / or emulsifiers.
  • a physiologically approved oil such as, for example, sesame oil, corn oil, cottonseed oil, soybean oil or peanut oil, esters of medium-chain vegetable fatty acids and fish oils such as, for example, mackerel, sprat or salmon oil use.
  • Protective colloids used are, for example, gelatin, fish gelatin, starch, dextrin, plant proteins, pectin, gum arabic, casein, caseinate or mixtures thereof.
  • polyvinyl alcohol, polyvinyl pyrrolidone, methyl cellulose, carboxymethyl cellulose, hydroxypropyl cellulose and alginates can also be used.
  • a plasticizer to the colloid such as sugar or sugar alcohols, e.g. Sucrose, glucose, lactose, invert sugar, sorbitol, mannitol or glycerin.
  • the ratio of protective colloid and plasticizer to active principle is generally chosen so that the end product a formulation is obtained which, in addition to the active principle, contains 10 to 50% by weight of a protective colloid, 20 to 70% by weight of a plasticizer, all percentages based on the dry weight of the formulation, and, if appropriate, minor amounts of a stabilizer.
  • compositions are prepared in a manner known per se. For example, solubilisates or emulsions according to EP-A-0 055 817 or EP0 479 066 or EP-A-0 551 638 can be produced.
  • the preparation of dispersions and their conversion into a dry powder is u. a. in EP-A-0 498 824 and EP-A-0 410 236.
  • milk products such as yogurt, milk mix drinks or milk ice cream
  • pudding powders for example pudding powders
  • baking mixes for example fruit gums.
  • the invention also relates to food supplements, animal feed, food and pharmaceutical preparations containing the compositions described above.
  • Dietary supplements and pharmaceutical preparations which contain the mixture according to the invention of flavonoids which can be used according to the invention, in particular flavones and / or isoflavones and phloridzin / phloretin, include tablets, coated tablets and hard and soft gelatin capsules.
  • Preferred nutritional supplements are soft gelatin capsules, in which the mixtures are present as an oil-containing suspension within the capsules.
  • the content of flavonoids and of phloridzins or phloretins in these capsules is in the range from 0.5 to 200 mg active principle, preferably in the range from 1 to 100 mg active principle, particularly preferably in the range from 20 to 70 mg active principle.
  • physiologically acceptable carriers can be buffer solutions such as phosphate or citrate buffers, a solid or liquid filler, an encapsulation material or a solvent.
  • materials that can serve as pharmaceutical carriers are sugars such as lactose, glucose, sucrose; Starch such as corn starch and potato starch; Cellulose and its derivatives such as sodium carboxymethyl cellulose, ethyl cellulose and cellulose acetate; powdered tragacanth; Malt, gelatin; Tallow; -Medicine carriers such as cocoa butter and suppository waxes; Oils such as peanut oil, cottonseed oil, safflower oil, sesame oil, olive oil, corn oil and soybean oil; Polyols such as propylene glycol, glycerin, sorbitol, mannitol and polyethylene glycol; Esters such as ethyl oleate and ethyl laureate
  • wetting agents, emulsifiers, lubricants such as sodium lauryl sulfate and magnesium stearate, as well as colorants, coating agents and perfuming agents, flavors and preservatives can also be present in the preparations, in accordance with the requirements of the galenics.
  • the amount of active ingredient in the preparation for a single dose will vary depending on the patient being treated and the particular mode of administration. The specific dosage and posology depend on a number of factors. These include the patient's age, body weight, general health, gender, diet, time of administration, route of administration, combination with other medicines, and the severity of the individual condition for which the therapy is used. It is determined by a doctor depending on these factors.
  • Fig.l Genistin and genistein glucuronide recording (gray, white and black columns) in the presence and in the absence of phloridzin.
  • vascular and luminally perfused rat small intestine The small intestine was developed as in Andlauer, W., Kolb, J., Siebert, K. and Princest, P., Adv. Exp. Med. Biol. 1984; 180: 711-20 prepared. 24.5 ⁇ M genist and 1 mM phloridzin and 23.8 ⁇ M pure genist were added to the luminal medium. The vitality of the preparation was checked on the basis of the parameters oxygen uptake, pH, glucose, lactate and pyruvate concentrations in the perfusion media.
  • vascular and luminal samples were taken and the entire small intestine and associated blood vessels were examined.
  • the content of genist and phloridzin and its conjugates were determined with the help of RP-HPLC with subsequent UV and MS spectroscopy. This determination is in Andlauer et al., J. Nutr., 2000; 130: 843-6.
  • Table 4 Distribution of Genistin, Genistein and Gemsteiningglucuronid in the luminal, vascular and tissue compartment according to

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  • Life Sciences & Earth Sciences (AREA)
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  • Food Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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Abstract

L'invention concerne une composition contenant au moins un flavonoïde ainsi qu'au moins de la phloridzine ou de la phlorétine. Ces compositions conviennent à la production de produits alimentaires, de compléments alimentaires, d'additifs alimentaires, de produits alimentaires pour animaux, de compléments alimentaires pour animaux, d'additifs alimentaires pour animaux ou de nourriture pour sonde, ainsi qu'à la production de compositions pharmaceutiques servant à augmenter la résorption des flavonoïdes.
PCT/EP2001/012378 2000-10-27 2001-10-26 Compositions contenant des flavonoides et de la phloridzine ou de la phloretine WO2002034073A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002224796A AU2002224796A1 (en) 2000-10-27 2001-10-26 Compositions containing flavonoids and phlorizin or phloretin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10053496A DE10053496A1 (de) 2000-10-27 2000-10-27 Zusammensetzungen enthaltend Flavonoide und Phloridzin oder Phloretin
DE10053496.1 2000-10-27

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WO2002034073A2 true WO2002034073A2 (fr) 2002-05-02
WO2002034073A3 WO2002034073A3 (fr) 2002-11-14

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1338270A2 (fr) * 2002-02-26 2003-08-27 Diana Ingredients Utilisation dans un traitement cosmétique d'une fraction phénolique riche en dihydrochalcones
WO2003075943A2 (fr) * 2002-03-06 2003-09-18 The Medical Research And Education Trust Compositions d'extrait botanique et procedes d'utilisation
EP1808172A2 (fr) * 2002-03-06 2007-07-18 The Medical Research and Education Trust Compostions à base d'extraits botaniques et procédés d'utilisation
WO2008057963A2 (fr) * 2006-11-02 2008-05-15 The Coca-Cola Company Composition édulcorante très puissante renfermant du phytoestrogène et compositions sucrées par cette composition
ITPD20080367A1 (it) * 2008-12-12 2010-06-13 Zuccari Societa A Responsabilita Limitata In Bre Composizione comprendente isoflavoni
EP2368442A2 (fr) 2005-07-27 2011-09-28 Symrise AG Utilisation d'hespérétine pour améliorer le goût sucré
US9387219B2 (en) 2011-06-06 2016-07-12 Conopco, Inc. Edible composition
EP2994155A4 (fr) * 2013-05-08 2017-03-29 The University of Houston System Ciblage de l'interaction entre un egfr et un sglt1 pour la cancérothérapie
WO2017092796A1 (fr) 2015-12-01 2017-06-08 Symrise Ag Mélanges de substances
CN108882742A (zh) * 2016-02-10 2018-11-23 Pm国际股份公司 用以减少和/或阻止肠道葡萄糖吸收的含有番石榴苷的组合物、膳食补充剂、组合物的用途和膳食补充剂的制备方法

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US20030229136A1 (en) * 2002-04-18 2003-12-11 Nurulain Zaveri Novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents

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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1338270A3 (fr) * 2002-02-26 2005-10-05 Diana Ingredients Utilisation dans un traitement cosmétique d'une fraction phénolique riche en dihydrochalcones
FR2836336A1 (fr) * 2002-02-26 2003-08-29 Diana Ingredients Utilisation dans un traitement cosmetique d'une fraction phenolique riche en dihydrochalcones
EP1338270A2 (fr) * 2002-02-26 2003-08-27 Diana Ingredients Utilisation dans un traitement cosmétique d'une fraction phénolique riche en dihydrochalcones
US7285298B2 (en) 2002-02-26 2007-10-23 Diana Ingredients S.A. Use of a dihydrochalcone-rich phenolic fraction in a cosmetic treatment
US6805873B2 (en) 2002-02-26 2004-10-19 Diana Ingredients S.A. Use of a dihydrochalcone-rich phenolic fraction in a cosmetic treatment
EP1808172A3 (fr) * 2002-03-06 2010-05-26 Activephyto Technologies Limited Compostions à base d'extraits botaniques et procédés d'utilisation
WO2003075943A2 (fr) * 2002-03-06 2003-09-18 The Medical Research And Education Trust Compositions d'extrait botanique et procedes d'utilisation
WO2003075943A3 (fr) * 2002-03-06 2004-04-22 Sophie Chen Ph D Compositions d'extrait botanique et procedes d'utilisation
EP1808172A2 (fr) * 2002-03-06 2007-07-18 The Medical Research and Education Trust Compostions à base d'extraits botaniques et procédés d'utilisation
EP2368442A2 (fr) 2005-07-27 2011-09-28 Symrise AG Utilisation d'hespérétine pour améliorer le goût sucré
US9101161B2 (en) 2006-11-02 2015-08-11 The Coca-Cola Company High-potency sweetener composition with phytoestrogen and compositions sweetened therewith
WO2008057963A3 (fr) * 2006-11-02 2008-09-04 Coca Cola Co Composition édulcorante très puissante renfermant du phytoestrogène et compositions sucrées par cette composition
WO2008057963A2 (fr) * 2006-11-02 2008-05-15 The Coca-Cola Company Composition édulcorante très puissante renfermant du phytoestrogène et compositions sucrées par cette composition
ITPD20080367A1 (it) * 2008-12-12 2010-06-13 Zuccari Societa A Responsabilita Limitata In Bre Composizione comprendente isoflavoni
WO2010066852A1 (fr) * 2008-12-12 2010-06-17 Zuccari S.R.L. Composition comprenant des isoflavones
JP2012511547A (ja) * 2008-12-12 2012-05-24 ズッカーリ ソシエタ ア レスポンサビリタ リミタータ イソフラボン組成物
US9387219B2 (en) 2011-06-06 2016-07-12 Conopco, Inc. Edible composition
EP2994155A4 (fr) * 2013-05-08 2017-03-29 The University of Houston System Ciblage de l'interaction entre un egfr et un sglt1 pour la cancérothérapie
US9770482B2 (en) 2013-05-08 2017-09-26 The University Of Houston System Targeting the EGFR-SGLT1 interaction for cancer therapy
WO2017092796A1 (fr) 2015-12-01 2017-06-08 Symrise Ag Mélanges de substances
CN108882742A (zh) * 2016-02-10 2018-11-23 Pm国际股份公司 用以减少和/或阻止肠道葡萄糖吸收的含有番石榴苷的组合物、膳食补充剂、组合物的用途和膳食补充剂的制备方法

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