WO2010000373A1 - Huile contenant de l'hydroxytyrosol et d'autres biophénols avec une activité nutritionnelle préventive bénéfique - Google Patents

Huile contenant de l'hydroxytyrosol et d'autres biophénols avec une activité nutritionnelle préventive bénéfique Download PDF

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Publication number
WO2010000373A1
WO2010000373A1 PCT/EP2009/004155 EP2009004155W WO2010000373A1 WO 2010000373 A1 WO2010000373 A1 WO 2010000373A1 EP 2009004155 W EP2009004155 W EP 2009004155W WO 2010000373 A1 WO2010000373 A1 WO 2010000373A1
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WO
WIPO (PCT)
Prior art keywords
oil
hydroxytyrosol
olive oil
biophenols
processes
Prior art date
Application number
PCT/EP2009/004155
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English (en)
Other versions
WO2010000373A8 (fr
Inventor
Felicia Cisale
Luciano Villanova
Azzurra Villanova
Alessandro Marendino
Gianluca Fasiello
Original Assignee
Lachifarma S.R.L. Laboratorio Chimico Farmaceutico Salentino
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 Lachifarma S.R.L. Laboratorio Chimico Farmaceutico Salentino filed Critical Lachifarma S.R.L. Laboratorio Chimico Farmaceutico Salentino
Publication of WO2010000373A1 publication Critical patent/WO2010000373A1/fr
Publication of WO2010000373A8 publication Critical patent/WO2010000373A8/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013—Other fatty acid esters, e.g. phosphatides

Definitions

  • the present invention relates to an oil containing hydroxytyrosol and other biophenols as an additional ingredient.
  • oil refers to olive oil obtained by pressing the fruit of the olive tree (Olea europaea), and to all fats found in the liquid state at room temperature.
  • the Mediterranean diet has a proven ability to prevent disorders of the cardiocirculatory apparatus (heart attacks and thrombosis) and, almost certainly, other illnesses too. Attention was drawn to the Mediterranean diet in the 1950s by American nutritionist Ancel Keys, who had noticed the very low incidence of coronary disease in the inhabitants of Campania and the island of Crete, despite their high consumption of olive oil, and theorised that this was due to the diet typical of that geographical area. This observation was followed by the famous Seven Countries Study (published in the book "Eat well and stay well, the Mediterranean way"), based on a comparison of the diets of 12,000 people aged 40 to 59, living in seven countries on three continents (Finland, Japan, Greece, Italy, the Netherlands, USA and Yugoslavia).
  • said effects are attributable to various ingredients present in the foods traditionally used in the Mediterranean diet, namely monounsatured fatty acids (especially oleic acid), antioxidants and fibres.
  • monounsatured fatty acids especially oleic acid
  • antioxidants and fibres High quantities of monounsatured fatty acids are contained in extra virgin olive oil.
  • a good example of how useful monounsatured fatty acids are in maintaining good health is a natural food like breast milk, which is rich in fats whose composition resembles that of olive oil. When taken in the correct quantities, it reduces the levels of LDL ("bad” cholesterol) but increases or leaves unchanged the level of HDL ("good” cholesterol).
  • LDLs The danger of LDLs lies in their ability, if oxidised by free radicals, to trigger a mechanism that leads to gradual occlusion of the coronaries and consequent heart attack.
  • Antioxidants which are widespread throughout the plant world, are substances produced by plants to defend their own structures.
  • the antioxidants present in olive oil, for example, protect the oil against oxidation, thus preventing it from becoming rancid.
  • the antioxidants taken with the oil perform the same protective actions in the human body as in plants. In particular, they combat the oxidation produced by free radicals, a by-product of the chemical reactions that take place in the body.
  • Free radicals are harmless in themselves (for example, they represent a natural defence against infection), but harmful if produced in excess: oxidation of the LDLs, caused by free radicals, is the first stage on the route leading to occlusion of the coronaries (and other vessels).
  • the best-known antioxidants contained in olive oil are hydroxytyrosol and oleuropein, which belong to the class of phenols.
  • HT 3,4-Dihydroxyphenylethanol or hydroxytyrosol
  • LDLs Low-Density Lipoproteins
  • HT Due to its dual hydrophilic and lipophilic nature, HT is stored in the cell membranes, where it performs a protective action against oxidative damage caused by free radicals. It has been demonstrated that HT protects epithelial cell monolayers against the damage caused by hyperoxidation, which involves a reduction in cell viability and an abnormal increase in membrane permeability, leading to inflammation and oxidation of the polyunsaturated acids of the cell membranes.
  • the direct or mediated consequences of the protective effect against free radicals are a reduction in cardiovascular diseases (especially those connected with atherosclerosis) due to the prevention of oxidation of the LDLs and the proliferation of cholesterol, inflammatory disorders, aging, cell degeneration and angiogenesis with consequent tumours, microbial infections and diabetic conditions.
  • a process for preparing hydroxytyrosol with high purity suitable for use as an ingredient in the pharmaceutical, food and cosmetic industries is disclosed, for example, in EP 1623960.
  • An object of the present invention is to provide an edible vegetable oil that includes HT as a beneficial additional component, so as to provide a healthy, natural food product with additional health-giving and beneficial characteristics, which in particular provides nutritional prevention against damage caused by oxidative stress, inflammation, angiogenesis processes, hypercholesterolaemia, atherosclerotic processes and tumoral processes, and a general effect of nutritional prevention of aging.
  • the edible vegetable oil is preferably olive oil, in particular extravirgin olive oil.
  • HT is added to the olive oil according to the invention, which already contains percentages of hydroxytyrosol ranging between 0.005 and 0.8% by weight, in such quantities as to reach an HT content exceeding the maximum values found in the olive oils naturally available.
  • the olive oil according to the invention characterised by the addition to said oil of HT or fractions containing it, will therefore contain HT in percentages by weight of between 0.85 and 10%, preferably between 0.9 and 5%, and more preferably between 1 and 2%.
  • the HT-enriched olive oil of the invention retains the typical organoleptic characteristics of traditional olive oil as perceived by the consumer, at the same time presenting an increased antioxidant action.
  • Another purpose of the invention is the use of oil with added HT to improve the body resistance to oxidative stress, inflammation, angiogenesis processes, hypercholesterolaemia, atherosclerotic processes and tumoral processes, and a general effect of nutritional prevention of aging.
  • the oil according to the invention may possibly contain other ingredients selected from those typically contained in the olive, such as oleuropein, gallic acid, trihydroxybenzoic acid, caffeic acid, etc.
  • the HT added to the extravirgin olive oil supplements the baseline quantity of polyphenols naturally contained in the oil, which is in the
  • the oil according to the invention maintains the organoleptic properties, chemico-physical characteristics and content of HT and other polyphenols and, surprisingly, is stable for at least 30 months.
  • the vegetable oils normally marketed have a shelf life not exceeding 12-18 months.
  • oil according to the invention containing hydroxytyrosol in addition to other biophenols and possibly other health-giving ingredients, are set out below.
  • the preparation was divided into aliquots, each placed in a 30 ml dark glass food container with metal crimp cap; one part was left at room temperature and another was placed in a climatic chamber at 30 0 C ⁇ 2°C and 60% RH ⁇ 5% RH [32].
  • the preparations were monitored for 24 months, and the results of the determinations are set out below.
  • the formulation based on extravirgin olive oil with added hydroxytyrosol retains the quantity of polyphenols for longer than the same oil without added hydroxytyrosol. Moreover, the higher hydroxytyrosol content better preserves the oil against the formation of peroxides, and keeps the acidity low (see graphs in Figures 2 and 3).
  • Figure 4 shows an example of typical HPLC-UV chromatogram at 280 nm.
  • the mixture was produced according to the method described in EP 1623960 so as to obtain an 0.1% hydroxytyrosol concentration.
  • the preparation was divided into aliquots, each of which was placed in a 30 ml dark glass food container with a metal crimp cap; one part was left at room temperature, and another was placed in a climatic chamber at 3O 0 C ⁇ 2 0 C and 60% RH ⁇ 5% RH [32].
  • the preparations were monitored for 12 months, and the results of the determinations are set out below:

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

L'invention porte sur une huile qui contient de l'hydroxytyrosol en tant qu’ingrédient additionnel, de façon à produire un produit alimentaire naturel et bon pour la santé doté de caractéristiques additionnelles bénéfiques et bonnes pour la santé, qui offre en particulier une prévention nutritionnelle contre les lésions provoquées par la contrainte oxydante, l'inflammation, l'angiogenèse et les processus tumoraux associés, l'hypercholestérolémie et les processus athérosclérotiques, et un effet général de prévention nutritionnelle du vieillissement.
PCT/EP2009/004155 2008-06-30 2009-06-10 Huile contenant de l'hydroxytyrosol et d'autres biophénols avec une activité nutritionnelle préventive bénéfique WO2010000373A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI2008A001201 2008-06-30
ITMI20081201 ITMI20081201A1 (it) 2008-06-30 2008-06-30 Olio contenente idrossitirosolo ed altri biofenoli ad attivita' nutrizionale preventiva benefica

Publications (2)

Publication Number Publication Date
WO2010000373A1 true WO2010000373A1 (fr) 2010-01-07
WO2010000373A8 WO2010000373A8 (fr) 2010-03-11

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PCT/EP2009/004155 WO2010000373A1 (fr) 2008-06-30 2009-06-10 Huile contenant de l'hydroxytyrosol et d'autres biophénols avec une activité nutritionnelle préventive bénéfique

Country Status (2)

Country Link
IT (1) ITMI20081201A1 (fr)
WO (1) WO2010000373A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2925307A1 (fr) * 2012-11-30 2015-10-07 McCord, Darlene E. Compositions d'hydroxytyrosol et d'oleuropéine pour l'induction de dommages de l'adn, de la mort de cellules et de l'inhibition lsd1
WO2016087428A1 (fr) * 2014-12-04 2016-06-09 Dsm Ip Assets B.V. Enrichissement d'huiles comestibles en hydroxytyrosol
CN110799040A (zh) * 2017-04-14 2020-02-14 莱维斯维塔食品公司 一种用于制备高多酚橄榄油的方法和设备

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997032947A1 (fr) * 1996-03-05 1997-09-12 Comiter Trading & Services S.R.L. Produit a base d'huile d'olive, enrichi et complete par des antioxydants
WO2008102047A1 (fr) * 2007-02-22 2008-08-28 Universidad De Granada Composition d'huile d'olive et son utilisation comme aliment fonctionnel
WO2009013596A2 (fr) * 2007-07-23 2009-01-29 Probelte Pharma, S.A. Enrichissement de produits nutritionnels avec des extraits d'olive contenant de l'hydroxytyrosol, et produits nutritionnels enrichis en hydroxytyrosol

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997032947A1 (fr) * 1996-03-05 1997-09-12 Comiter Trading & Services S.R.L. Produit a base d'huile d'olive, enrichi et complete par des antioxydants
WO2008102047A1 (fr) * 2007-02-22 2008-08-28 Universidad De Granada Composition d'huile d'olive et son utilisation comme aliment fonctionnel
WO2009013596A2 (fr) * 2007-07-23 2009-01-29 Probelte Pharma, S.A. Enrichissement de produits nutritionnels avec des extraits d'olive contenant de l'hydroxytyrosol, et produits nutritionnels enrichis en hydroxytyrosol

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BOUAZIZ, M., ET AL: "Effect of storage on refined and husk olive oils composition: Stabilization by addition of natural antioxidants from Chemlali olive leaves", FOOD CHEMISTRY., vol. 108, 1 February 2008 (2008-02-01), GBELSEVIER SCIENCE PUBLISHERS LTD., pages 253 - 262, XP002541263, ISSN: 0308-8146 *
CHIOU, A., ET AL.: "Retention and distribution of polyphenols after pan-frying of french fries in oils enriched with olive leaf extract", JOURNAL OF FOOD SCIENCE., 2007, USINSTITUTE OF FOOD TECHNOLOGISTS. CHICAGO., XP002541262, ISSN: 0022-1147 *
SALTA, F. N., ET AL.: "Oxidative stability of edible vegetable oils enriched in polyphenols with olive leaf extract", FOOD SCIENCE AND TECHNOLOGY INTERNATIONAL, 2007, NEW YORK, NY, XP002541264, ISSN: 1082-0132 *
VISIOLI, F., ET AL.: "Hydroxytyrosol excretion differs between rats and humans and depends on the vehicle of administration", JOURNAL OF NUTRITION., vol. 133, 2003, USWISTAR INSTITUTE OF ANATOMY AND BIOLOGY, PHILADELPHIA, PA,, pages 22612 - 2615, XP002541265, ISSN: 0022-3166 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2925307A1 (fr) * 2012-11-30 2015-10-07 McCord, Darlene E. Compositions d'hydroxytyrosol et d'oleuropéine pour l'induction de dommages de l'adn, de la mort de cellules et de l'inhibition lsd1
EP2925307A4 (fr) * 2012-11-30 2016-06-08 Darlene E Mccord Compositions d'hydroxytyrosol et d'oleuropéine pour l'induction de dommages de l'adn, de la mort de cellules et de l'inhibition lsd1
US9662302B2 (en) 2012-11-30 2017-05-30 Darlene E. McCord Hydroxytyrosol and oleuropein compositions for induction of DNA damage, cell death and LSD1 inhibition
US10231939B2 (en) 2012-11-30 2019-03-19 Darlene E. McCord Hydroxytyrosol and oleuropein compositions for induction of DNA damage, cell death and LSD1 inhibition
WO2016087428A1 (fr) * 2014-12-04 2016-06-09 Dsm Ip Assets B.V. Enrichissement d'huiles comestibles en hydroxytyrosol
CN110799040A (zh) * 2017-04-14 2020-02-14 莱维斯维塔食品公司 一种用于制备高多酚橄榄油的方法和设备

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Publication number Publication date
WO2010000373A8 (fr) 2010-03-11
ITMI20081201A1 (it) 2010-01-01

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