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WO2008136037A3 - Chemical-catalytic method for the peracylation of oleuropein and its products of hydrolysis - Google Patents

Chemical-catalytic method for the peracylation of oleuropein and its products of hydrolysis Download PDF

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Publication number
WO2008136037A3
WO2008136037A3 PCT/IT2008/000303 IT2008000303W WO2008136037A3 WO 2008136037 A3 WO2008136037 A3 WO 2008136037A3 IT 2008000303 W IT2008000303 W IT 2008000303W WO 2008136037 A3 WO2008136037 A3 WO 2008136037A3
Authority
WO
WIPO (PCT)
Prior art keywords
oleuropein
products
peracylation
hydrolysis
hydroxytyrosol
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.)
Ceased
Application number
PCT/IT2008/000303
Other languages
French (fr)
Other versions
WO2008136037A2 (en
Inventor
Antonio Procopio
Giovanni Sindona
Nicola Costa
Marco Gaspari
Monica Nardi
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.)
Universita degli Studi "Magna Graecia" di Catanzaro
Universita della Calabria
Original Assignee
Universita degli Studi "Magna Graecia" di Catanzaro
Universita della Calabria
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
Priority claimed from ITMI20070904 external-priority patent/ITMI20070904A1/en
Priority claimed from ITMI20070903 external-priority patent/ITMI20070903A1/en
Application filed by Universita degli Studi "Magna Graecia" di Catanzaro, Universita della Calabria filed Critical Universita degli Studi "Magna Graecia" di Catanzaro
Priority to EP08763854A priority Critical patent/EP2235032A2/en
Publication of WO2008136037A2 publication Critical patent/WO2008136037A2/en
Publication of WO2008136037A3 publication Critical patent/WO2008136037A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Vascular Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Urology & Nephrology (AREA)
  • Biochemistry (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The method, object of the present invention, concerns the peracylation of oleuropein and its products of hydrolysis: The method makes use of the excellent properties as Lewis acid catalysts of halides and tryphilates of lanthanides (III). The component is placed to react, in the presence of catalytic quantities of Lewis acid, directly with an acylating agent containing at least one acylic group R, where R is H, an alkylic radical of 1-31 atoms of linear or branched carbon, an alkenylic radical containing up to 31 atoms of carbon or an arylic group. The procedures for the extraction and the successive hydrolysis of the oleuropein for the synthesis of its aglycon and the hydroxytyrosol, resolve the problems tied to the quantitative yield of the products and to the use of highly-toxic and expensive catalysts. Furthermore, the innovative and inventive contribution is given by the peracylation of the oleuropein and its products of synthesis, aglycon and hydroxytyrosol, that supply a new class of molecule, biologically active as anti-oxidants and anti-inflammatory ones. The proven anti-oxidant activity of oleuropein and its derivates leads to the hypothesis that they could also act as protectors against oxidative stress at the level of the central nervous system, one of the causal factors of Parkinson's disease. The molecules examined are all good protectors against oxidative stress and the greater efficiency of the peracylated derivatives is presumably due to their greater lipophilicity and the possibility of penetrating the cellular membrane.
PCT/IT2008/000303 2007-05-04 2008-05-05 Chemical-catalytic method for the peracylation of oleuropein and its products of hydrolysis Ceased WO2008136037A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08763854A EP2235032A2 (en) 2007-05-04 2008-05-05 Chemical-catalytic method for the peracylation of oleuropein and its products of hydrolysis

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
ITMI2007A000904 2007-05-04
ITMI20070904 ITMI20070904A1 (en) 2007-05-04 2007-05-04 CHEMICAL-CATALYTIC METHOD FOR THE HANDLING OF OLEUROPEINE FOR THE SYNTHESIS OF ITS AGLICONE.
ITMI2007A000903 2007-05-04
ITMI20070903 ITMI20070903A1 (en) 2007-05-04 2007-05-04 CHEMICAL-CATALYTIC METHOD FOR THE PERACIVATION OF OLEUROPEINE AND ITS HYDROLYSIS PRODUCTS.

Publications (2)

Publication Number Publication Date
WO2008136037A2 WO2008136037A2 (en) 2008-11-13
WO2008136037A3 true WO2008136037A3 (en) 2008-12-24

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IT2008/000303 Ceased WO2008136037A2 (en) 2007-05-04 2008-05-05 Chemical-catalytic method for the peracylation of oleuropein and its products of hydrolysis

Country Status (2)

Country Link
EP (1) EP2235032A2 (en)
WO (1) WO2008136037A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102532217B (en) * 2011-12-23 2014-12-10 王刻铭 Method for purifying and separating high-content oleuropein from olive leaves
CN104341307B (en) * 2013-08-05 2016-12-28 北京京朋汇药业研究发展有限公司 Phenylacetic acid derivatives and anticancer usage thereof
ITUA20163706A1 (en) * 2016-05-23 2017-11-23 Univ Degli Studi Magna Graecia Di Catanzaro Method of peracylation of natural compounds
CN106187708A (en) * 2016-07-25 2016-12-07 西安岳达生物科技股份有限公司 A kind of preparation method of high-purity hydroxytyrosol
WO2019151299A1 (en) * 2018-02-02 2019-08-08 国立研究開発法人産業技術総合研究所 Method for producing glutaraldehyde derivative originating in natural material
CN110128246B (en) * 2019-06-10 2022-07-26 杭州志源生物科技有限公司 A kind of preparation method of hydroxytyrosol
CN113277931A (en) * 2021-06-04 2021-08-20 陕西富恒生物科技有限公司 Method for extracting hydroxytyrosol from olive fruits

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6117844A (en) * 1994-11-07 2000-09-12 F&S Group, Inc. Method and composition for antiviral therapy
WO2003082259A1 (en) * 2002-04-03 2003-10-09 Puleva Biotech, S.A. Natural phenolic products and derivatives thereof for protection against neurodegenerative diseases

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6117844A (en) * 1994-11-07 2000-09-12 F&S Group, Inc. Method and composition for antiviral therapy
WO2003082259A1 (en) * 2002-04-03 2003-10-09 Puleva Biotech, S.A. Natural phenolic products and derivatives thereof for protection against neurodegenerative diseases

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
A. PROCOPIO ET AL.: "Erbium(III)triflate as an extremely active acylation catalyst", ADV. SYNTH. CATAL., vol. 346, 2004, pages 1465 - 1470, XP002501018 *
H. INOUYE ET AL.: "Über die Monoterpenglucoside und verwandte Naturstoffe-XXII", TETRAHEDRON, vol. 30, 1974, pages 201 - 209, XP002501019 *
K. INOUE ET AL.: "Two secoiridoid glucosides from Jasminum mesnyi", PHYTOCHEMISTRY, vol. 24, 1985, pages 1299 - 1303, XP002501017 *

Also Published As

Publication number Publication date
EP2235032A2 (en) 2010-10-06
WO2008136037A2 (en) 2008-11-13

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