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US20060057231A1 - Pterostilbene as a new agonist for the peroxisome proliferator-activated receptor alpha isoform - Google Patents

Pterostilbene as a new agonist for the peroxisome proliferator-activated receptor alpha isoform Download PDF

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Publication number
US20060057231A1
US20060057231A1 US11/207,038 US20703805A US2006057231A1 US 20060057231 A1 US20060057231 A1 US 20060057231A1 US 20703805 A US20703805 A US 20703805A US 2006057231 A1 US2006057231 A1 US 2006057231A1
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pterostilbene
resveratrol
pparα
composition
individual
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Agnes Rimando
Dennis Feller
Wallace Yokoyama
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University of Mississippi
US Department of Agriculture USDA
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Assigned to THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY OF AGRICULTURE reassignment THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY OF AGRICULTURE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: YOKOYAMA, WALLACE H., RIMANDO, AGNES M.
Assigned to MISSISSIPPI, UNIVERSITY OF THE reassignment MISSISSIPPI, UNIVERSITY OF THE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FELLER, DENNIS RUDOLPH
Assigned to AGRICULTURE, UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY OF, THE reassignment AGRICULTURE, UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY OF, THE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: YOKOYAMA, WALLACE H., RIMANDO, AGNES M.
Publication of US20060057231A1 publication Critical patent/US20060057231A1/en
Priority to US12/911,376 priority patent/US8133917B2/en
Priority to US13/363,959 priority patent/US8252845B1/en
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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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
    • 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
    • A61K31/33—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
    • 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)
    • A61K36/45—Ericaceae or Vacciniaceae (Heath or Blueberry family), e.g. blueberry, cranberry or bilberry
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • This invention relates to pterostilbene, an analog of resveratrol, found in grapes, wine, peanuts and other berries.
  • Pterostilbene activates the peroxisome proliferator-activated receptor alpha (PPAR ⁇ ) isoform, a receptor proposed to mediate the activity of lipid-lowering drugs.
  • PPAR ⁇ peroxisome proliferator-activated receptor alpha
  • pterostilbene is capable of acting as an effective hypolipidemic agent.
  • the peroxisome proliferator-activated receptor (PPAR) isoforms are members of the nuclear receptor superfamily of ligand-activated transcription factors. They were first identified in Xenopus frogs as receptors that induce the proliferation of peroxisomes (Dreyer et al., 1992. Cell 68: 879-887). Three PPAR isoforms are known: PPAR ⁇ , PPAR ⁇ , and PPAR ⁇ . The PPARs control gene expression by interaction with specific response elements in the promoter region of target genes (Tugwood et al. 1996. Ann. New York Acad. Sci. 804: 252-265).
  • the PPARs play a central role in carbohydrate and lipid homeostasis, and govern other biological processes such as energy metabolism, cell proliferation and differentiation, and inflammation (Chakrabarti and Rajagopalan. 2004. Curr. Med. Chem.: Immunol. Endocr. Metab. Agents 4: 67-73; Escher and Wahli. 2000. Mutation Res. 448:121-138; Gilde and Van Bilsen. 2003. Acta Physiol. Scand. 178: 425-434; Kersten, S. 2002. Eur. J. Pharmacol. 440: 223-234; Mudaliar and Henry. 2002. Curr. Opin. Endocrinol. Diabetes 9: 285-302).
  • the PPARs are also suggested to play a role in the pathogenesis and proliferation of colorectal (Jackson et al. 2003. Gut 52: 1317-1322) and lung (Inoue et al. 2001. Anticancer Res. 21: 2471-2476) tumor progression possibly via inhibition of proliferation.
  • the PPAR ⁇ isoform predominantly involved in fatty acid and lipid catabolism and import, activates genes involved in fatty acid oxidation in the liver, heart, kidney, and skeletal muscles (Fruchart et al. 2003. Prog. Exper. Cardiol. 8: 3-16; Gilde and Van Bilsen, supra).
  • PPAR ⁇ activation leads to increased ⁇ -oxidation of fatty acids and decreased triglyceride-VLDL synthesis (Fruchart and Duriez. 2004. Ann. Pharmaceut. Franc. 62: 3-18). Activation of PPAR ⁇ also leads to the reduction of triglyceride because of repression of hepatic apolipoprotein C-III and to the increase in lipoprotein lipase gene expression (Gervois et al. 2000. Clin. Chem. Lab. Med. 38: 3-11). Furthermore, PPAR ⁇ activation causes induction of hepatic apolipoprotein A-I and A-II expression, in humans, leading to increased plasma HDL cholesterol.
  • PPAR ⁇ agonists also slow down the progression of premature coronary atherosclerosis (Fruchart et al. 2003, supra) and have been demonstrated to regulate metabolism of amino acids in the liver (Kersten et al. 2001. FASEB J. 15: 1971-1978).
  • Resveratrol is a well-known antioxidant (Stivala et al. 2001. J. Biol. Chem. 276: 22586-22594; Teguo et al. 1998. J. Nat. Prod. 61: 655-657) and cancer chemopreventive compound (Jang et al. 1997. Science 275: 218-220) present in grapes and wine. Its occurrence in wine has been linked to low incidence of fatal coronary heart disease among populations consuming wine moderately (Hegsted and Aussman. 1988. J. Nutr. 118: 1184-1189; Renaud and De Lorgeril. 1992. Lancet 339:1523).
  • Pterostilbene is another grape compound that also was found to have antioxidant (Rimando et al. 2002. J. Agric. Food Chem. 50: 3453-3457; Stivala et al., supra) and cancer chemopreventive property similar to resveratrol (Rimando et al., supra).
  • Pterostilbene has antidiabetic (Manickam et al. 1997. J. Nat. Prod. 60: 609-610) properties, and inhibits the enzymes cyclooxygenase-1 (COX-1) and COX-2, inferring anti-inflammatory properties (Likhitwitayawuid et al. 2002. Planta Medica 68: 841-843).
  • pterostilbene is cytotoxic to a number of cancer cell lines in vitro (Rimando et al., 1994. Nat. Prod. Lett. 4: 267-272).
  • the cytochrome P450 enzyme CYP1B1 metabolizes resveratrol to piceatannol, demonstrating that a natural cancer chemopreventive agent can be converted to an anticancer compound by an enzyme which is over expressed in a wide variety of human tumors (Potter et al. 2002. Brit. J. Cancer 86: 774-778).
  • Piceatannol showed anti-allergic effects in experimental models of type I allergy (Matsuda et al. 2001. Biol. Pharm. Bull. 24: 264-267). It has also been shown to induce apoptotic cell death in BJAB lymphoma cells with activity equal to resveratrol.
  • Piceatannol also induced apoptosis in ex vivo assays with leukemic lymphoblasts, whereas resveratrol did not (Wieder et al. 2001. Leukemia 15: 1735-1742).
  • Resveratrol trimethylether was found to be more cytotoxic than resveratrol in cultured human lung and colon cancer cells (Lee et al. 2003. Arch. Pharm. Res. 26: 253-257).
  • this invention provides a method of treating dyslipidemias in individuals at risk of cardiovascular disease by administering a pharmaceutical composition containing pterostilbene.
  • kits comprising a pharmaceutical composition containing pterostilbene; and instructions for the use of the kit.
  • FIG. 1 shows the structures and formulae of resveratrol, pterostilbene, piceatannol, resveratrol trimethylether, and ciprofibrate.
  • FIG. 2 shows the effect of stilbenes on PPAR ⁇ in H4IIEC3 cells transfected with the PPRE-AB-luciferase reporter gene plasmid.
  • Cip ciprofibrate
  • Res resveratrol
  • Pic picetannol
  • Pte pterostilbene
  • Rte resveratrol trimethyl ether
  • ns not significantly different from control, p>0.05
  • **, significantly different from control, p 0.001
  • Dyslipidemias are disorders of lipoprotein metabolism, including lipoprotein overproduction or deficiency. These disorders may be manifested by elevation of the serum total cholesterol, low-density lipoprotein (LDL) cholesterol and triglyceride concentrations, and a decrease in the high-density lipoprotein (HDL) cholesterol concentration.
  • Resveratrol has been shown to have hypolipidemic properties in rat feeding studies causing lowering of triglyceride (Miura et al., supra) and serum cholesterol levels (Miura et al., supra; Kollar et al. 2000. Vnitrni Lekarstvi 46: 856-860).
  • PPAR ligands or agonists evolved as a group of structurally diverse compounds that activate these transcription factors, and emerged as an important class of therapeutic agents as PPARS have become an important molecular target to treat human metabolic disorders.
  • PPARs play a central role in lipid homeostasis in regulating fatty acid metabolism and plasma lipoproteins.
  • the fibrate drugs, such as ciprofibrate that was used in this study, were found to be ligands for PPAR ⁇ and their activation of PPAR ⁇ provided a mechanistic explanation for their clinical efficacy to treat cardiovascular diseases (Roberts and Moffat. 2001. Comments on Toxicology 7: 259-273).
  • resveratrol Three analogs of resveratrol: pterostilbene, piceatannol and resveratrol trimethylether have been shown to exhibit some of the same biological activities as resveratrol; however, these analogs also have individual activities which they do not share with resveratrol.
  • pterostilbene is an agonist for PPAR ⁇ and that it possesses an activity comparable to a clinically prescribed hypolipidemic fibrate drug, provides a possible natural source alternative for the treatment of dyslipidemias.
  • resveratrol is a cholesterol lowering agent, the mechanism by which it does so does not appear to be via activation of PPAR ⁇ , as is shown in this study.
  • Results from this study suggest that pterostilbene may be a more effective hypolipidemic agent with differing mechanisms of lipid lowering action than that of resveratrol.
  • Pterostilbene has been reported in some small fruits such as grapes (Adrian et al., 2000. J. Agric. Food Chem. 48: 6103-6105) and berries of Vaccinium (Rimando et al. 2004. J. Agric. Food Chem. 52: 4713-4719) as well as in woody plants (Maurya et al. 1984. J. Nat. Prod. 47: 179-181; Amone et al. 1977. J. Chem. Soc. Perkins Trans. 19: 2116-2118).
  • Resveratrol and piceatannol were commercial samples obtained from Sigma-Aldrich (St. Louis, Mo.) and Calbiochem (San Diego, Calif.), respectively.
  • H4IIEC3 cells were obtained from the American Type Culture Collection (Rockville, Md.).
  • the PPRE-AB luciferase gene reporter construct was obtained from Dr. Daniel J. Noonan (Department of Biochemistry, University of Kentucky, Lexington, Ky.).
  • the luciferase assay kit was obtained from Promega Corporation (Madison, Wis.).
  • NMR experiments were carried out on a Bruker Avance DRX (500 MHZ) instrument.
  • PTLC Merck Si gel F254 20 ⁇ 20 cm, 0.5 mm thick plate (VWR Scientific, Atlanta, Ga.). All solvents used were HPLC grade (Fisher Scientific, Suwanee, Ga.).
  • Pterostilbene and resveratrol trimethylether were prepared by partial methylation of resveratrol.
  • resveratrol 150 mg in 3.0 ml of MeOH
  • diazomethane a solution of resveratrol (150 mg in 3.0 ml of MeOH) diazomethane was added dropwise, and the reaction was monitored by thin layer chromatography (TLC) for the methylated products.
  • TLC thin layer chromatography
  • the reaction solution was dried under vacuum.
  • the partially methylated products were purified by preparative TLC (developing solvent, hexane: ETOAc, 8:2; Rf 0.6 and 0.8 for pterostilbene and resveratrol trimethylether, respectively). The identity and structure of these compounds were confirmed by comparison with published spectroscopic data.
  • H4IIEC3 cells a rat hepatoma cell line, were grown in a 150 mm Petri dish containing Dulbecco's Modified Eagle's Medium (DMEM) supplemented with 10% (v/v) fetal bovine serum.
  • DMEM Dulbecco's Modified Eagle's Medium
  • PPRE-AB peroxisome proliferator response element with rat fatty acyl CoA ⁇ -oxidase AB promoter region sequence
  • PPRE-AB peroxisome proliferator response element with rat fatty acyl CoA ⁇ -oxidase AB promoter region sequence
  • pterostilbene demonstrated the highest induction of luciferase activity at 100 and 300 ⁇ M ( FIG. 1 ).
  • Diets were prepared by dissolving powdered cholesterol into warmed butterfat, followed by the addition of corn and fish oil. The small amounts of test ingredients were dissolved in about 50 ml of ethanol and added to the stirring dry ingredients. The liquid fat was also added to the dry ingredients while stirring. The composition is shown in Table 1. TABLE 1 Composition of Diet Ingredient Wt. (g) Butterfat, anhydrous 80 Corn Oil 100 Fish Oil, Menhaden 20 Cholesterol 1.5 Cellulose, microcrystalline 50 Casein 200 Starch, corn 497.5 Methionine 3 Choline bitartrate 3 Mineral Mix 35 Vitamin Mix 10 Test Substance 25 mg/kg
  • LDL low density lipoprotein

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008070872A1 (fr) * 2006-12-07 2008-06-12 Rutgers, The State University Of New Jersey Prévention et traitement du cancer du côlon
US20090069444A1 (en) * 2007-09-07 2009-03-12 The United States Of America, As Represented By Th E Secretary Of Agriculture Method to Ameliorate Oxidative Stress and Improve Working Memory Via Pterostilbene Administration
US20100119499A1 (en) * 2009-09-17 2010-05-13 Kneller Bruce W Stilbene-based compositions and methods of use therefor
KR101018405B1 (ko) 2008-10-13 2011-02-28 한국생명공학연구원 정금나무 잎 추출물을 유효성분으로 함유하는 비만 예방 및치료용 조성물
WO2012154956A3 (fr) * 2011-05-11 2013-01-24 The United States Of America, As Represented By The Secretary Of Agriculture Effet anxiolytique du ptérostilbène
US20130136778A1 (en) * 2009-10-30 2013-05-30 Green Molecular, S.L. Pterostilbene (pter) for use in the prevention and/or treatment of skin diseases, damages or injuries
US20130296441A1 (en) * 2012-05-03 2013-11-07 Agnes Rimando Anti-Obesity Properties of Pterostilbene
US8846061B1 (en) * 2011-03-08 2014-09-30 Mark S. Bezzek Multivitamin-mineral regimens for longevity and wellness
US12485085B2 (en) 2020-12-14 2025-12-02 Rodan & Fields, Llc PPAR agonist complex and methods of use

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006020999A2 (fr) * 2004-08-19 2006-02-23 The United States Of America, As Represented By The Secretary Of Agriculture Pterostilbene en tant que nouvel agoniste pour l'isoforme du recepteur alpha active de la proliferation de peroxysomes
US20130072509A1 (en) * 2011-09-15 2013-03-21 ChromaDex Inc. Pterostilbene and statin combination for treatment of metabolic disease, cardiovascular disease, and inflammation
US20130149277A1 (en) * 2011-12-13 2013-06-13 Cliffstar Llc Pterostilbene and pvp grape juice extract combination for treatment of metabolic, vascular, and neurodegenerative disorders
CN102936546B (zh) * 2012-11-29 2013-12-11 刘淑银 一种保健葡萄酒

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US20050038125A1 (en) * 2003-08-15 2005-02-17 Smit Hobbe Friso Method for the treatment of arthritis and pain
US20050049208A1 (en) * 2003-09-03 2005-03-03 Kaufmann Doug A. Method of treating and method of preventing diabetes
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US6190716B1 (en) * 1999-02-17 2001-02-20 Scott O. Galbreath, Jr. Method for preparing a grape derived product
US20020028852A1 (en) * 1999-09-21 2002-03-07 Geetha Ghai Resveratrol analogs for prevention of disease
US7361374B2 (en) * 2002-05-17 2008-04-22 S.S. Steiner, Inc. Application for hop acids as anti-microbial agents
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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008070872A1 (fr) * 2006-12-07 2008-06-12 Rutgers, The State University Of New Jersey Prévention et traitement du cancer du côlon
US8426369B2 (en) 2006-12-07 2013-04-23 Rutgers, The State University Of New Jersey Prevention and treatment of colon cancer
CN101820869A (zh) * 2007-09-07 2010-09-01 美国农业部 通过施用紫檀芪减轻氧化应激并改善工作记忆的方法
US20090069444A1 (en) * 2007-09-07 2009-03-12 The United States Of America, As Represented By Th E Secretary Of Agriculture Method to Ameliorate Oxidative Stress and Improve Working Memory Via Pterostilbene Administration
WO2009032870A3 (fr) * 2007-09-07 2009-05-22 Us Agriculture Procédé pour traiter le stress oxydatif et améliorer la mémoire de travail par administration de ptérostilbène
CN101820869B (zh) * 2007-09-07 2012-12-12 美国农业部 通过施用紫檀芪减轻氧化应激并改善工作记忆的方法
KR101018405B1 (ko) 2008-10-13 2011-02-28 한국생명공학연구원 정금나무 잎 추출물을 유효성분으로 함유하는 비만 예방 및치료용 조성물
US20100119499A1 (en) * 2009-09-17 2010-05-13 Kneller Bruce W Stilbene-based compositions and methods of use therefor
US20130136778A1 (en) * 2009-10-30 2013-05-30 Green Molecular, S.L. Pterostilbene (pter) for use in the prevention and/or treatment of skin diseases, damages or injuries
AU2010311326B2 (en) * 2009-10-30 2016-10-06 Green Molecular, S.L Pterostilbene (PTER) for use in the prevention and/or treatment of skin diseases, damages or injures
AU2016234952B2 (en) * 2009-10-30 2018-08-16 Green Molecular, S.L Pterostilbene (PTER) for use in the prevention and/or treatment of skin diseases, damages or injures
US8846061B1 (en) * 2011-03-08 2014-09-30 Mark S. Bezzek Multivitamin-mineral regimens for longevity and wellness
US9161565B1 (en) 2011-03-08 2015-10-20 Mark S. Bezzek Multivitamin-mineral regimens for longevity and wellness
US9167839B1 (en) 2011-03-08 2015-10-27 Mark S. Bezzek Multivitamin-mineral regimens for longevity and wellness
WO2012154956A3 (fr) * 2011-05-11 2013-01-24 The United States Of America, As Represented By The Secretary Of Agriculture Effet anxiolytique du ptérostilbène
US20130296441A1 (en) * 2012-05-03 2013-11-07 Agnes Rimando Anti-Obesity Properties of Pterostilbene
US12485085B2 (en) 2020-12-14 2025-12-02 Rodan & Fields, Llc PPAR agonist complex and methods of use

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