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ES2184640B1 - CONJUGATES OF FLAVANOLES AND CISTEINA. - Google Patents

CONJUGATES OF FLAVANOLES AND CISTEINA.

Info

Publication number
ES2184640B1
ES2184640B1 ES200102081A ES200102081A ES2184640B1 ES 2184640 B1 ES2184640 B1 ES 2184640B1 ES 200102081 A ES200102081 A ES 200102081A ES 200102081 A ES200102081 A ES 200102081A ES 2184640 B1 ES2184640 B1 ES 2184640B1
Authority
ES
Spain
Prior art keywords
cysteine
new
molecules
flavanols
conjugation
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Fee Related
Application number
ES200102081A
Other languages
Spanish (es)
Other versions
ES2184640A1 (en
Inventor
Josep Lluis Torres Simon
Carles Lozano Perez
Marta Cascante Serratosa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Consejo Superior de Investigaciones Cientificas CSIC
Universitat Autonoma de Barcelona UAB
Universitat de Barcelona UB
Original Assignee
Consejo Superior de Investigaciones Cientificas CSIC
Universitat Autonoma de Barcelona UAB
Universitat de Barcelona UB
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 Consejo Superior de Investigaciones Cientificas CSIC, Universitat Autonoma de Barcelona UAB, Universitat de Barcelona UB filed Critical Consejo Superior de Investigaciones Cientificas CSIC
Priority to ES200102081A priority Critical patent/ES2184640B1/en
Priority to PCT/ES2002/000438 priority patent/WO2003024951A1/en
Publication of ES2184640A1 publication Critical patent/ES2184640A1/en
Application granted granted Critical
Publication of ES2184640B1 publication Critical patent/ES2184640B1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
    • 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
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/542—Carboxylic acids, e.g. a fatty acid or an amino acid

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Conjugados de flavanoles y cisteína. La presente invención se refiere a nuevos productos que resultan de la conjugación de flavanoles con cisteína. Las nuevas moléculas se obtienen a partir de extractos polifenólicos de plantas por conjugación con el aminoácido natural cisteína. De esta manera se generan nuevos productos con propiedades antioxidantes/antiradicalarias con aplicación como agentes protectores del organismo contra trastornos como el cáncer, enfermedades cardiovasculares y envejecimiento prematuro. Las moléculas resultantes puras son antioxidantes más eficientes que sus componentes (flavanoles y cisteína) por separado. El concepto de nuevos productos derivados de cisteína con propiedades antioxidantes se extiende desde las moléculas puras hasta sus mezclas, los crudos de tiólisis y fracciones parcialmente purificadas. La invención se refiere también al método de aislamiento y purificación de los nuevos compuestos a partir de mezclas complejas.Flavanol and cysteine conjugates. The present invention relates to new products that result from the conjugation of flavanols with cysteine. The new molecules are obtained from polyphenolic extracts of plants by conjugation with the natural amino acid cysteine. In this way, new products with antioxidant / anti-radical properties with application as protective agents of the organism against disorders such as cancer, cardiovascular diseases and premature aging are generated. The resulting pure molecules are more efficient antioxidants than their components (flavanols and cysteine) separately. The concept of new cysteine-derived products with antioxidant properties extends from pure molecules to mixtures, thiolysis crudes and partially purified fractions. The invention also relates to the method of isolation and purification of the new compounds from complex mixtures.

ES200102081A 2001-09-17 2001-09-17 CONJUGATES OF FLAVANOLES AND CISTEINA. Expired - Fee Related ES2184640B1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
ES200102081A ES2184640B1 (en) 2001-09-17 2001-09-17 CONJUGATES OF FLAVANOLES AND CISTEINA.
PCT/ES2002/000438 WO2003024951A1 (en) 2001-09-17 2002-09-17 Flavonol and cysteine conjugates

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES200102081A ES2184640B1 (en) 2001-09-17 2001-09-17 CONJUGATES OF FLAVANOLES AND CISTEINA.

Publications (2)

Publication Number Publication Date
ES2184640A1 ES2184640A1 (en) 2003-04-01
ES2184640B1 true ES2184640B1 (en) 2004-08-16

Family

ID=8498933

Family Applications (1)

Application Number Title Priority Date Filing Date
ES200102081A Expired - Fee Related ES2184640B1 (en) 2001-09-17 2001-09-17 CONJUGATES OF FLAVANOLES AND CISTEINA.

Country Status (2)

Country Link
ES (1) ES2184640B1 (en)
WO (1) WO2003024951A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ536591A (en) * 2003-05-26 2008-07-31 Amino Up Chemical Co Ltd Sulfur-containing proanthocyanidin oligomer composition and production method thereof
EP1627565A1 (en) * 2004-08-10 2006-02-22 Consejo Superior de Investigaciones Cientificas (CSIC) Use of flavanol derivatives for the cryopreservation of living cells
JP2008201745A (en) * 2007-02-21 2008-09-04 Asahi Breweries Ltd New flavanol compound and method for producing the same

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
LIN, Y.L. y LIN, J.K. "(-)-Epigallocatechin 3-gallate blocks the induction of nitric oxide synthase by down regulating lipopolysaccharide induced activity of transcription factor nuclear Factor-KB". Molecular Pharmacoloy, 1997, Volumen 52, páginas 465-472. Todo el documento. *
TANAKA, T. et al. "Synthesis and antioxidant activity of novel amphipathic derivatives of tea polyphenol". Bioorganic & Medicinal Chemistry Letters, 1998, Volumen 8, páginas 1801-1806. Resumen; figura 1. *

Also Published As

Publication number Publication date
WO2003024951A1 (en) 2003-03-27
ES2184640A1 (en) 2003-04-01

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