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 PDFInfo
- 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
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
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.
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 | ||
ITMI2007A000903 | 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. |
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
ID=39855088
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IT2008/000303 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)
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 |
JP7137853B2 (en) * | 2018-02-02 | 2022-09-15 | 国立研究開発法人産業技術総合研究所 | Method for producing natural product-derived glutaraldehyde derivative |
CN110128246B (en) * | 2019-06-10 | 2022-07-26 | 杭州志源生物科技有限公司 | 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)
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 |
-
2008
- 2008-05-05 WO PCT/IT2008/000303 patent/WO2008136037A2/en active Application Filing
- 2008-05-05 EP EP08763854A patent/EP2235032A2/en not_active Withdrawn
Patent Citations (2)
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)
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 |
---|---|
WO2008136037A2 (en) | 2008-11-13 |
EP2235032A2 (en) | 2010-10-06 |
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