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
- RFWGABANNQMHMZ-UHFFFAOYSA-N 8-acetoxy-7-acetyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline Natural products CC=C1C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O RFWGABANNQMHMZ-UHFFFAOYSA-N 0.000 title abstract 5
- HKVGJQVJNQRJPO-UHFFFAOYSA-N Demethyloleuropein Natural products O1C=C(C(O)=O)C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(=CC)C1OC1OC(CO)C(O)C(O)C1O HKVGJQVJNQRJPO-UHFFFAOYSA-N 0.000 title abstract 5
- RFWGABANNQMHMZ-HYYSZPHDSA-N Oleuropein Chemical compound O([C@@H]1OC=C([C@H](C1=CC)CC(=O)OCCC=1C=C(O)C(O)=CC=1)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RFWGABANNQMHMZ-HYYSZPHDSA-N 0.000 title abstract 5
- 235000011576 oleuropein Nutrition 0.000 title abstract 5
- RFWGABANNQMHMZ-CARRXEGNSA-N oleuropein Natural products COC(=O)C1=CO[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)C(=CC)[C@H]1CC(=O)OCCc3ccc(O)c(O)c3 RFWGABANNQMHMZ-CARRXEGNSA-N 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 4
- 230000007062 hydrolysis Effects 0.000 title abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 title abstract 3
- JUUBCHWRXWPFFH-UHFFFAOYSA-N Hydroxytyrosol Chemical compound OCCC1=CC=C(O)C(O)=C1 JUUBCHWRXWPFFH-UHFFFAOYSA-N 0.000 abstract 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 235000003248 hydroxytyrosol Nutrition 0.000 abstract 2
- 229940095066 hydroxytyrosol Drugs 0.000 abstract 2
- 230000036542 oxidative stress Effects 0.000 abstract 2
- 230000001012 protector Effects 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 abstract 2
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 208000018737 Parkinson disease Diseases 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- 235000006708 antioxidants Nutrition 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 230000001364 causal effect Effects 0.000 abstract 1
- 230000001413 cellular effect Effects 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052747 lanthanoid Inorganic materials 0.000 abstract 1
- 150000002602 lanthanoids Chemical class 0.000 abstract 1
- 239000011968 lewis acid catalyst Substances 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 239000012528 membrane Substances 0.000 abstract 1
- 230000000149 penetrating effect Effects 0.000 abstract 1
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)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Vascular Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (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.
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 |
| 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 | 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 EP EP08763854A patent/EP2235032A2/en not_active Withdrawn
- 2008-05-05 WO PCT/IT2008/000303 patent/WO2008136037A2/en active Application Filing
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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