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WO2004054573A1 - Methode et composition permettant d'inhiber la digestion des glucides - Google Patents

Methode et composition permettant d'inhiber la digestion des glucides Download PDF

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Publication number
WO2004054573A1
WO2004054573A1 PCT/NL2003/000888 NL0300888W WO2004054573A1 WO 2004054573 A1 WO2004054573 A1 WO 2004054573A1 NL 0300888 W NL0300888 W NL 0300888W WO 2004054573 A1 WO2004054573 A1 WO 2004054573A1
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WO
WIPO (PCT)
Prior art keywords
component
eft
composition
epimedium
carbohydrate
Prior art date
Application number
PCT/NL2003/000888
Other languages
English (en)
Inventor
Katien Maria Jozefa VAN LAERE
Gerrit Jan Witte
Evan Abrahamse
Ingeborg Frances PALM
Original Assignee
N.V. Nutricia
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by N.V. Nutricia filed Critical N.V. Nutricia
Priority to AU2003294185A priority Critical patent/AU2003294185A1/en
Publication of WO2004054573A1 publication Critical patent/WO2004054573A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics

Definitions

  • the present invention relates to a method for the treatment and prevention of a diet responsive condition, the method comprising the enteral administration of a Epimedium flavonoid type component obtainable from Epimedium plant material.
  • Diabetes afflicts a significant number of people, approximately 5 % of the population, and yet the treatment of diabetes leaves a lot to be desired.
  • insulin is an absolute necessity. It is typically administered by injection, needs to be co-ordinated with a balanced diet and exercise, and must be carefully monitored.
  • weight loss is advisable, but is frequently usually difficult to achieve. Tablets, such as oral hypoglycemic agents, or insulin may be required.
  • diabetes complications such as blindness, kidney failure, nerve damage, and atherosclerosis, still are a major problem.
  • compositions that prevent, treat and/or ameliorate diabetes and overweight.
  • Plant material from Epimedium species are known to have a variety of beneficial effects on health. Extracts of Epimedium species enriched in icariside I or anhydroicaritin have for example been described to treat sexual dysfunction in
  • CN1211424 describes a Chinese medicine for reducing fat and loosing weight, that is prepared from 11 Chinese-medicinal materials such as lotus leaf, haw, tuckahoe, Epimedium and red sage root.
  • CN1161851 describes a Chinese medicine for curing diabetes, which is prepared by using effective components of the Chinese medicinal herbs of anemarrhena root, adenophora root, dried rehmannia root, cornus fruit, alisma tuber, Epimedium and saliva root.
  • JP 03068547 describes flavonoids contained in inter alia Epimedium grandiflorum for use as aldose reductase inhibiting agents.
  • the present inventors have identified an Epimedium flavonoid type component (EFT component) that is capable of reducing intestinal carbohydrase activity.
  • EFT component Epimedium flavonoid type component
  • the finding that the EFT component is capable of reducing intestinal carbohydrase activity enables the manufacture of compositions from the Epimedium flavonoid type component containing plants or plant parts, wherein the efficacy of the (herbal) composition can be predicted based on its the chemical composition.
  • the inventors have surprisingly found that oral administration of an effective amount of the flavonoid type component reduces blood glucose levels in rats.
  • the blood glucose-lowering properties are indicative for the suitability to use the present flavonoid type component or extracts enriched therein in the treatment or prevention of diabetes.
  • weight gain or loss for an individual is essentially the difference between the amount of calories absorbed and the amount of calories burned. Enteral ingestion of the carbohydrase inhibitor will reduce the uptake of carbohydrates present in a meal or snack. The reduced absorption of carbohydrates results in weight loss or less weight gain due to the lower consumption of calories.
  • the EFT component or extract enriched therein can be advantageously used in a method for the treatment or prevention of obesity.
  • One aspect of the present invention relates to a method for the prevention or treatment of a diet responsive condition, said method comprising enterally administering to the mammal an effective amount of the Epimedium flavonoid type component of formula (I) hereinafter defined, obtainable from Epimedium plant material.
  • the present invention provides a method for the reduction of intestinal carbohydrate absorption and/or delaying intestinal carbohydrate absorption in mammals, said method comprising the administration of a carbohydrate absorption reducing amount of the Epimedium flavonoid type component of formula (I) hereinafter defined.
  • the present invention provides a method for the treatment or prevention of overweight in a mammal, said method comprising administering to the mammal an effective amount of the Epimedium flavonoid type component of formula (I) hereinafter defined.
  • the present invention relates to a composition enriched in the present EFT component, particularly a composition comprising at least 0.5 wt.% of the Epimedium flavonoid type component of formula (I) hereinafter defined.
  • Figure 1 represents the results of the experiments performed in Example 2 and illustrates the in vivo effects of EFT component on postprandial glucose response.
  • Figure 2 represents the results of the experiments performed in Example 2 and illustrates the in vivo effects of EFT component on postprandial insulin response.
  • Figure 3 represents the chromatogram of the experiments performed in example 1.
  • the arrow indicates the peak of the EFT component according to the present invention.
  • the present invention relates to a method for the treatment and/or prevention of a diet responsive condition, comprising administering to a mammal an effective amount of Epimedium flavonoid type component (EFT component) or a pharmaceutically acceptable salt thereof, wherein the EFT component has the formula (I)
  • Ri is hydrogen or carbohydrate
  • R 2 is hydrogen or carbohydrate
  • R 3 is a (C 2 -C 12 ) alkyl, (C 2 -C ⁇ 2 ) alkoxy, (C 2 -C ⁇ 2 ) alkenyl, (C2-C12) alkynyl, cycloalkyl, aryl or heteroaryl.
  • R- t , R 5 , R 6 , R , R 8 , R and Rio independently represent hydrogen, hydroxy or amme
  • Ri represents a carbohydrate, more preferably a carbohydrate comprising one or more hexose units, even more preferably a monosaccharide residue or oligosaccharide residue, most preferably a di- or trisaccharide, particularly a disaccharide.
  • the disaccharide has the structure: rhamnose-X or glucose-X, in which X represents a saccharide selected from the group consisting of rhamnose and xylose and wherein preferably the rhamnose or xylose, more preferably the rhamnose, is covalently attached to the basic flavonoid structure.
  • R 2 represents a carbohydrate, more preferably carbohydrate comprising one or more hexose units, even more preferably a monosaccharide residue or oligosaccharide residue, most preferably a monosaccharide.
  • the monosaccharide is preferably selected from the group consisting of fructose, galactose, rhamnose, glucose and xylose.
  • R 2 represent glucose.
  • R 3 is a (C ⁇ -C ⁇ 2 ) alkyl, (C 2 -C ⁇ 2 ) alkenyl, (C -C ⁇ 2 ) alkoxy or (C 2 -C 12 ) alkynyl, more preferably a (C -C ⁇ 2 ) alkenyl. Most preferably R 3 represents
  • R 5 , R 7 , R 8 and R 9 are hydrogen.
  • R 6 and R 9 are hydroxy or amine, more preferably hydroxy.
  • the EFT component has one of the following structures (formula II or formula III):
  • the present invention also provides the composition according to formula III.
  • the EFT component as described in formula III, or a phannaceutically acceptable salt thereof is particularly suitable for use as a medicament.
  • the present invention also provides the EFT component as described in formula I, or a pharmaceutically acceptable salt thereof, wherein Ri is disaccharide rhamnose-xylose; and R 6 is hydrogen, for use as a medicament.
  • the present invention relates to a composition
  • a composition comprising: at least 0.5 wt.%, preferably at least 1 wt.% more preferably at least 2.5 wt.%, more preferably at least 5 wt.%, even more preferably at least 10 wt.%, most preferably at least 50 wt.% of the EFT component based on dry weight of the composition; and a pharmaceutical acceptable carrier.
  • These compositions can be advantageously used in a method for the treatment or prevention of diet responsive conditions.
  • the EFT component may be chemically manufactured, biochemically produced (e.g. in a fermentation process) or be obtained from vegetable material, optionally followed by subsequent chemical modification.
  • the EFT component is provided by and/or obtained from Epimedium plant material.
  • Epimedium plant material refers to any plant material obtained from one or more plants belonging to the genus Epimedium, including material obtained by extracting, commuting, drying or other chemical or physical treatment of Epimedium plants or parts thereof.
  • Preferred plant sources of the EFT component are E. acuminatum, E. baicaliquizhounense, E. baojingenensis, E. brevicornum, E. clongatum, E. caotum, E. davidii, E.
  • the Epimedium plant material used in accordance with the present invention may be obtained from whole plants or from one or more parts thereof, for example stems, stalks, roots, shoots, rhizomes, tubers, fruits (including seeds), foliage, kernels, husks, hulls or mixtures thereof.
  • the Epimedium plant material is administered in the form of a plant isolate, more preferably in the form of an Epimedium plant extract.
  • isolated as referred to herein, encompasses any fraction that can be obtained from a plant material by means of isolation techniques known in the art, particularly one selected from extraction, distillation or squeezing, and that displays the desired functional properties described herein before.
  • extract as used in the present invention refers to an isolate that has been obtained by means of solvent extraction.
  • the whole plant or a part thereof is preferably first subjected to physical processes prior to the preparation of the isolate.
  • the plants or plant parts are typically subjected to one or more of the following processes prior to the isolation step: grinding, flaking, freezing, drying, commuting and the like.
  • the Epimedium plant or plant parts are thereafter preferably subjected to one or more isolation processes selected from the group consisting of solvent extraction, cold pressing, hot pressing, distillation, chromatography and filtering, more preferably the Epimedium plant material is subjected to solvent extraction (including supercritical extraction and percolation).
  • the solvents used to prepare the Epimedium extract are polar solvents, more preferably a solvent selected from the group consisting of alcohols, water and mixtures thereof, most preferably selected from the group consisting of water, ethanol and mixtures thereof.
  • the present invention relates to an Epimedium extract containing at least 0.5 wt.%, preferably at least 1 wt.% more preferably at least 2.5 wt.%, more preferably at least 5 wt.%, even more preferably at least 10 wt.%, most preferably at least 50 wt.% of the EFT component based on dry weight of the Epimedium plant extract.
  • the extract enriched in the EFT component is combined with a pharmaceutical acceptable carrier.
  • the present invention provides a method for the treatment or prevention of a diet responsive condition in a mammal.
  • Diet responsive condition refers to any disease or physical state that can be caused or grow worse by the ingestion of proteins, carbohydrates or fats.
  • the present method particularly aims to inhibit intestinal carbohydrate absorption and hence is particularly suitable for a suppressing fluctuations in blood glucose levels, prevention of diabetes, inhibition of insulin level increase and/or obesity, as these conditions all benefit from the inhibited intestinal absorption of carbohydrates.
  • the present invention preferably does not relate to the treatment of complications of diabetes and/or complications accompanied by diabetes, such as cataract, retinopathy or nephropathy
  • Inhibition of intestinal carbohydrate absorption within the context of this invention refers specifically to a decrease of the intestinal enzyme activity that is associated with the hydrolysis of di-, tri-, oligo- and polysaccharides.
  • the present method leads to a decreased net absorption of monosaccharides from dietary digestible carbohydrates or to an absorption of monosaccharides over an increased surface area of the small intestine (i.e. absorption spread out over a longer period of time).
  • the present method is particularly suitable for (prophylactically) treating obesity as the reduction in carbohydrate absorption will usually also lead to a reduction of body weight, a reduction of body weight increase or a reduction in production of body fat.
  • Another advantageous application of the method is its use for suppressing fluctuations in blood glucose levels, preferably inhibition of postprandial blood glucose level increase, which is particularly beneficial for diabetics.
  • the present invention is particularly suitable for the dietary management of diabetes.
  • the present invention provides a method for the treatment of diabetes, said method comprising enterally administering to the mammal an effective amount of EFT component or a pharmaceutically acceptable salt thereof, wherein the EFT component has the structure of formula I and wherein R 2 represents a carbohydrate.
  • the present invention can be advantageously used in a method for the treatment or prevention of diabetes and overweight.
  • Carbohydrates that are readily degraded within the intestine are those carbohydrates that can be digested by one or more of the salivatory, pancreatic or brush border enzymes of a given mammal, hi case of humans these enzymes include glucoamylase (glucosidase), isomaltase, ⁇ -limit dextrinase, sucrase, lactase, pancreatic amylase and/or salivatory amylase.
  • Examples of digestible carbohydrates are sucrose and digestible starches.
  • the present method preferably comprises the administration of an effective amount of the EFT component.
  • a daily amount of between 0.1 and 250 mg EFT component per kg of body weight is administered to a mammal, more preferably between 0.5 and 100 mg/kg body weight, even more preferably between 1 and 50 mg/kg body weight, most preferably between 2.5 and 20 mg/kg body weight.
  • the present method comprises the oral administration of the EFT component.
  • the EFT component is swallowed after application to the oral cavity.
  • the EFT component is provided in a dosage.
  • the dosage used in the present method can be applied in any suitable form, such as bars, pills, capsules, gels, liquid etc, however is preferably provided in the form of a pill, tablet or capsule.
  • a dosage does not consist of more than 3 tablets, capsules or pills, even more preferably consists of a single pill, capsule or tablet.
  • at least two dosages, more preferably at least three dosages, are administered in one day.
  • a daily dosage of the preparation as used in the present invention can include one or more pills, tablets or capsules.
  • a daily dosage consists of 1 to 6 pills, tablets or capsules.
  • a dosage is preferably in a solid or semisolid form, more preferably in a form selected from the group consisting of pills, capsules, tablets, caplet, microparticles and microspheres.
  • the solid or semisolid dosage form preferably has a weight between 0.1 and 30 grams, more preferably between 0.2 and 10 grams.
  • the EFT component is provided in a unit dosage form.
  • unit dosage form refers to a physically discrete unit suitable for unitary administration to human subjects and other mammals, wherein each unit contains a predetermined quantity of Epimedium plant material and a pharmaceutically acceptable carrier.
  • These carriers may be selected from sugars, starches, cellulose and its derivatives, malt, gelatine, talc, calcium sulphate, vegetable oils, synthetic oils, polyols, alginic acid, phosphate buffered solutions, emulsifiers, isotonic saline, and pyrogen-free water.
  • the unit dosage form has a caloric value below 100 kcal, more preferably below 50 kcal even more preferably below 10 kcal.
  • a dosage preferably has a weight between 0.2 and 4 grams, even more preferably between 0.5 and 3 grams.
  • Example 1 Preparation of composition enriched in EFT component
  • Sample solution was prepared by dissolving Epimedium extract (Epimedium P.E; Kingherb International, Changchun, China) in demineralised water at a concentration of 50 mg per ml and subsequently centrifuged (10 min, 10.000 g) and filtered using a 0.2 ⁇ filter.
  • Epimedium extract Epimedium P.E; Kingherb International, Changchun, China
  • the EFT component was collected and analyzed using mass spectrometry to determine the structure of the EFT component.
  • EFT component i.e. Epimedium composition enriched in EFT component
  • the method as described in Example 1 was repeated 50 times and the pooled samples were freeze dried.
  • the resulting powder (hereinafter refened to as P7) is about 44 times more potent in inhibiting carbohydrase activity on weight basis (see Table 1).
  • the degree of activity increase was determined by comparing the slope of linear regression (percentage inhibition of 10 mU amylase activity per ⁇ g dry matter) of different concentrations of Epimedium P.E. and P7 dilutions against ⁇ -amylase inhibitory activity.
  • mice received the carbohydrate test meal (1.75 g cornstarch + 0.5 g sucrose with or without test component) via oral gavage.
  • carbohydrate test meal 1.75 g cornstarch + 0.5 g sucrose with or without test component
  • blood samples 0.2 ml were taken via the permanent canula and collected in ice- chilled, heparinized tubes for determination of plasma glucose (glucose oxidase- peroxidase method) and insulin (radioimmunoassay) concentrations.
  • the treatment groups received either test meal (control), test meal with Epimedium P.E. (166 mg) or test meal with P7 (4 mg).
  • the glucose response after the test meal was calculated by the area under the curve (AUC), relative to the basal levels.
  • Figure 1 shows a reduced area AUC for both test groups receiving Epimedium P.E.. The results are indicative for the suitability of the present EFT component for use in a method for suppressing fluctuations in blood glucose levels, prevention of diabetes and/or treatment or prevention of obesity.
  • results are indicative for the suitability of use of a composition enriched in the present EFT component for use in a method for suppressing fluctuations in blood glucose levels, prevention of diabetes and/or treatment or prevention of obesity, as for P7 only 4 mg had to be administered to the rats in order to achieve an effect similar to the administration of 166 mg Epimedium P.E.
  • Figure 2 shows a reduced area AUC for both test groups receiving Epimedium extract. The results are indicative for the suitability of the present EFT component for use in a method for reduction of insulin level increase, prevention of diabetes and/or treatment or prevention of obesity.
  • Composition comprising 5 mg P7 and a pharmaceutically acceptable carrier for use in a method for the prevention of diabetes, particularly diabetes type II, said method comprising orally administering said composition to a human.
  • Example 4 Composition for treatment and/or prevention of overweight Composition comprising 2 mg EFT component of Formula III and a pharmaceutically acceptable carrier for use in a method for the treatment and/or prevention of overweight, said method comprising orally administering said composition to a human.

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  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Engineering & Computer Science (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Child & Adolescent Psychology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne une méthode de traitement et de prévention d'un état répondant à un régime consistant à inhiber la digestion des glucides dans l'intestin, au moyen d'un composé pouvant être obtenu à partir de l'Epimedium.
PCT/NL2003/000888 2002-12-13 2003-12-15 Methode et composition permettant d'inhiber la digestion des glucides WO2004054573A1 (fr)

Priority Applications (1)

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AU2003294185A AU2003294185A1 (en) 2002-12-13 2003-12-15 Method and composition for inhibiting carbohydrate digestion

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EP02080259 2002-12-13
EP02080259.1 2002-12-13

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0368517A (ja) * 1989-08-08 1991-03-25 Tsumura & Co アルドースリダクターゼ阻害剤
WO2001001969A2 (fr) * 1999-07-06 2001-01-11 Endorecherche, Inc. Methodes de traitement et/ou de suppression de la prise de poids
WO2001001996A1 (fr) * 1999-06-29 2001-01-11 University Of Western Australia Compositions et methodes de traitement ou de prevention de l'osteoporose
WO2001021608A2 (fr) * 1999-09-23 2001-03-29 Vereniging Voor Christelijk Wetenschappelijk Onderwijs Nouveaux flavonoides
US20020013280A1 (en) * 2000-06-16 2002-01-31 Zhongcheng Xin Pharmaceutical composition for preventing and treating sexual dysfunction and vasculargenic disease comprising icariin

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0368517A (ja) * 1989-08-08 1991-03-25 Tsumura & Co アルドースリダクターゼ阻害剤
WO2001001996A1 (fr) * 1999-06-29 2001-01-11 University Of Western Australia Compositions et methodes de traitement ou de prevention de l'osteoporose
WO2001001969A2 (fr) * 1999-07-06 2001-01-11 Endorecherche, Inc. Methodes de traitement et/ou de suppression de la prise de poids
WO2001021608A2 (fr) * 1999-09-23 2001-03-29 Vereniging Voor Christelijk Wetenschappelijk Onderwijs Nouveaux flavonoides
US20020013280A1 (en) * 2000-06-16 2002-01-31 Zhongcheng Xin Pharmaceutical composition for preventing and treating sexual dysfunction and vasculargenic disease comprising icariin

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002235640, Database accession no. BRN: 3643902 *
LI W-K ET AL: "FLAVONOIDS FROM EPIMEDIUM WANSHANENSE", PHYTOCHEMISTRY, PERGAMON PRESS, GB, vol. 43, no. 2, 1996, pages 527 - 530, XP002907017, ISSN: 0031-9422 *
LIANG H-R ET AL: "ISOLATION AND IMMUNOMODULATORY EFFECT OF FLAVONOL GLYCOSIDES FROM EPIMEDIUM HUNANENSE", PLANTA MEDICA, THIEME, STUTTGART, DE, vol. 63, 1997, pages 316 - 319, XP002907018, ISSN: 0032-0943 *
PATENT ABSTRACTS OF JAPAN vol. 015, no. 227 (C - 0839) 10 June 1991 (1991-06-10) *
PHYTOCHEMISTRY, vol. 43, no. 2, 1996, pages 527 - 530 *

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