WO2008138324A1 - Extraits phénoliques de graines oléagineuses - Google Patents

Extraits phénoliques de graines oléagineuses Download PDF

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Publication number
WO2008138324A1
WO2008138324A1 PCT/DE2008/000808 DE2008000808W WO2008138324A1 WO 2008138324 A1 WO2008138324 A1 WO 2008138324A1 DE 2008000808 W DE2008000808 W DE 2008000808W WO 2008138324 A1 WO2008138324 A1 WO 2008138324A1
Authority
WO
WIPO (PCT)
Prior art keywords
phenol
starting material
aqueous
extraction
extract
Prior art date
Application number
PCT/DE2008/000808
Other languages
German (de)
English (en)
Inventor
Usha Thiyam
Peter Eisner
Klaus Müller
Michael Menner
Original Assignee
Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V.
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 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. filed Critical Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V.
Publication of WO2008138324A1 publication Critical patent/WO2008138324A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L11/00—Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
    • A23L11/30—Removing undesirable substances, e.g. bitter substances
    • A23L11/32—Removing undesirable substances, e.g. bitter substances by extraction with solvents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/30—Physical treatment, e.g. electrical or magnetic means, wave energy or irradiation
    • A23L5/32—Physical treatment, e.g. electrical or magnetic means, wave energy or irradiation using phonon wave energy, e.g. sound or ultrasonic waves

Definitions

  • the invention relates to highly effective and native phenolic compounds which are obtained in the form of extracts from oilseeds or from press cake or meal of these seeds after the edible oil production.
  • phenolic compounds are phytochemicals which may be an important component of pharmaceutical preparations.
  • Several studies have described the importance of phenolic compounds for the prevention of coronary heart disease or other beneficial effects of phenols for health maintenance or therapeutic applications.
  • Phenolic acids such as caffeic acid or bile acid, catechins, flavones (e.g., quercitin),
  • Phenolic compounds are usually obtained by conventional process engineering operations, for example in continuous processes such as Countercurrent extraction and DC extraction, but also in batch process.
  • the object of the present invention is to obtain high-purity phenol extracts from oilseeds or from residues of edible oil production.
  • the vegetable, phenol-containing starting material is provided in comminuted form, is de-oiled to a residual oil content and is suspended in an aqueous, aqueous-alcoholic or alcoholic solvent.
  • phenol-containing cells of the plant, phenol-containing Starting material mechanically disrupted by a periodic alternating pressure load.
  • the phenol enrichment is already largely complete in the short time, ie to> 90% based on a maximum possible yield.
  • the phenol-containing extract is obtained by mechanical separation of a supernatant.
  • Extract is characterized by a particularly low proportion of non-phenolic compounds or substances.
  • the particular advantage of the method is that the phenolic compounds are extracted faster than proteins in particular. This automatically prevents an irreversible attachment of proteins to the phenolic compounds, which leads to a loss of the particularly advantageous health-promoting, antioxidant activity of the phenolic compounds.
  • the particular advantage of the process is that even aqueous solvents can be used for the extraction of phenolic compounds in high yield without a high proportion of non-phenolic substances being extracted with it. It is particularly advantageous that the cost of cleaning the extract can be significantly reduced here, since water is neutral as a solvent, harmless to health and also unproblematic in terms of disposal.
  • a further particular advantage of the process is that due to the high extraction rate, the phenolic compounds already undergo less structural changes by oxidation than in other extraction processes which require a longer period of time for the extraction of the same amount of phenol.
  • the temperature of the solvent and the mixing temperature in the suspension should be less than 10 ° C. Preferably, the temperature is 5 + / 2 0 C.
  • the temperature is controlled during the cell digestion or regulated by cooling.
  • the low temperature during the extraction process has a particularly favorable effect on the suppression of the oxidation of the phenolic compounds and on the minimization of the proportion of non-phenolic components in the extract.
  • the alternating pressure load can be effected in a particularly advantageous manner by coupling of ultrasound.
  • the energy density is at least an order of magnitude above that which can be introduced by stirring.
  • the energy density should preferably between 10 8 and 10 9 J / m 3 , more preferably at 5 * 10 8 J / m 3 .
  • mechanical energy is introduced for a short period of 1 minute such that 80% of phenol enrichment is completed before a non-phenolic concentration increases above 1%.
  • minimization of non-phenolic components in the extract can be achieved by the intense mechanical cell disruption in conjunction with low temperatures and the very short extraction time.
  • the concentration of non-phenolic compounds in the extract is particularly low if the conductivity of the solvent, in particular of the water used, is less than 1.5 ⁇ S / cm.
  • the use of water with a conductivity of 0.5 ⁇ S / cm has proved to be particularly advantageous.
  • the conductivity is correlated with the ion concentration.
  • the yield of phenolic compounds in the extract increases with decreasing solid-liquid ratio s: l (solid: liquid).
  • the yield is particularly high when s: 1 ⁇ 1, preferably ⁇ 0.85.
  • the method can be developed particularly advantageous if further environmental conditions are selected so that the phenols undergo no structural changes by oxidation during the extraction. Then, through the process especially valuable phenolic compounds are obtained, the effectiveness of which, for example, as antioxidants was not restricted or destroyed by oxidation during the extraction process.
  • Phenolic acids are oxidized in an alkaline medium, whereby partial pressure of oxygen, temperature and catalysts, such as metals or enzymes, influence the rate of oxidation.
  • the intact structure, such as the antioxidant effect of the phenolic compounds can be retained particularly easily if the pH of the
  • Suitable phenol-containing starting material are, for example, oil seeds, press cake or extraction pellets of edible oil production.
  • the seeds are de-oiled before phenol production.
  • the seeds can be peeled and / or flocculated before de-oiling. If seeds are peeled, the peel fraction can be used in the same way for the production of phenols as the fruit pulp fraction.
  • Starting material should be ⁇ 6%, preferably ⁇ 2%.
  • the proportion of shell in extraction slices from peeled seeds should be ⁇ 20%, preferably ⁇ 10%.
  • the liquid and the solid phase are separated by centrifugation.
  • the separated solid can be resuspended in a fresh medium and treated under defined conditions. This process can be repeated as often as you like.
  • the extracts obtained by the process contain, in high concentration, its own phenolic compounds such as, for example, sinapine, sinapinic acid or its derivatives, tannins, ferulic acid, caffeic acid or derivatives thereof.
  • the extracts can be used as antioxidants for food or non-food applications or for pharmaceutical purposes or as an additive in crop protection products.
  • the targeted selection of the environmental conditions and the procedure for the extraction of the phenolic compounds the simultaneous extraction of high levels of non-phenolic substances is avoided.
  • the cleaning effort for the phenol preparations is thus significantly reduced.
  • the effort for the removal of proteins is significantly reduced.
  • Example 1 the parameters are selected so that comparable phenol yields as in aqueous-alcoholic extractions (without mechanical cell disruption) can be achieved with purely aqueous extractions (with mechanical cell disruption).
  • Example 2 it is shown by the choice of the parameters that at the same phenol yield as in Example 1 The proportion of non-phenolic compounds in the extract increases significantly without mechanical cell disruption and at high temperature.
  • the shot used for the phenol extraction was industrially made from peeled rapeseed black peel.
  • the shells are separated from the pulp by air classification
  • Pulp fraction is 15%.
  • the pulp fraction is adjusted to a platelet thickness of 0.25 mm +/- 0.05 mm by means of a flaking roller.
  • the rape flakes are de-oiled with hexane.
  • the residual fat content in the extraction meal is about 2%.
  • the starting material used for phenol production is the same rapeseed meal as described in Example 1. 10 g of deoiled shot are suspended in 100 ml of water at 25 0 C and stirred for 30 minutes with a magnetic stirrer.
  • the batch is centrifuged.
  • the supernatant of the centrifugation is the phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-containing phenol-
  • Extract of about 7-12 mg / g phenolic substances The proportion of non-phenolic compounds is about 50%. In contrast, the proportion of non-phenolic substances in extraction with advanced mechanical cell termination and low temperature (Example 1) is about 32%.
  • the intensive mechanical input of energy through ultrasound causes the extract to reach approximately the same phenol concentration after 1 minute of ultrasonic treatment as during a 30-minute stirring process.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Botany (AREA)
  • Agronomy & Crop Science (AREA)
  • Mycology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Extraction Or Liquid Replacement (AREA)

Abstract

L'invention concerne un procédé d'extraction d'un extrait contenant du phénol à partir d'une matière première végétale contenant du phénol, consistant à mettre en oeuvre la matière première végétale contenant du phénol sous forme broyée, à déshuiler la matière première jusqu'à une teneur en huile résiduelle et à la mettre en suspension dans un solvant aqueux, aqueux alcoolique ou alcoolique. Pendant un court intervalle inférieur à 10 minutes, des cellules contenant du phénol de la matière première végétale contenant du phénol sont décomposées mécaniquement par soumission périodique à une pression alternative. L'extrait contenant du phénol est obtenu par séparation mécanique d'un liquide surnageant. Des conditions de milieu et de processus adaptées permettent d'obtenir notamment des composés phénoliques non-oxydés. La teneur en composés non-phénoliques dans l'extrait obtenu au moyen dudit procédé est particulièrement faible.
PCT/DE2008/000808 2007-05-15 2008-05-14 Extraits phénoliques de graines oléagineuses WO2008138324A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007022662A DE102007022662A1 (de) 2007-05-15 2007-05-15 Phenolextrakte aus Ölsaaten
DE102007022662.6 2007-05-15

Publications (1)

Publication Number Publication Date
WO2008138324A1 true WO2008138324A1 (fr) 2008-11-20

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DE2008/000808 WO2008138324A1 (fr) 2007-05-15 2008-05-14 Extraits phénoliques de graines oléagineuses

Country Status (2)

Country Link
DE (1) DE102007022662A1 (fr)
WO (1) WO2008138324A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112980445A (zh) * 2021-03-26 2021-06-18 四川大学 一种从花椒油加工副产物中提取酚类抗氧化剂的方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102014107607A1 (de) * 2014-05-28 2015-12-03 Gea Mechanical Equipment Gmbh Verfahren zur Gewinnung von Sinapinsäure aus einem nativen Stoffgemenge

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4072671A (en) * 1975-02-21 1978-02-07 Snamprogetti, S.P.A. Method for extracting phenols and oligosaccharides from vegetable tissues
GB2004197A (en) * 1977-09-19 1979-03-28 Halle Rationalisierung Veb Extraction process
RU2104733C1 (ru) * 1996-11-06 1998-02-20 Сульман Михаил Геннадьевич Способ экстракции из твердого растительного сырья
EP1704907A1 (fr) * 2003-12-08 2006-09-27 Peisheng Cao Procede d'extraction et appareil associe
WO2008074072A1 (fr) * 2006-12-18 2008-06-26 Cavitus Pty Ltd Extraction à ultrasons haute énergie

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4072671A (en) * 1975-02-21 1978-02-07 Snamprogetti, S.P.A. Method for extracting phenols and oligosaccharides from vegetable tissues
GB2004197A (en) * 1977-09-19 1979-03-28 Halle Rationalisierung Veb Extraction process
RU2104733C1 (ru) * 1996-11-06 1998-02-20 Сульман Михаил Геннадьевич Способ экстракции из твердого растительного сырья
EP1704907A1 (fr) * 2003-12-08 2006-09-27 Peisheng Cao Procede d'extraction et appareil associe
WO2008074072A1 (fr) * 2006-12-18 2008-06-26 Cavitus Pty Ltd Extraction à ultrasons haute énergie

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
HERRERA M C ET AL: "Ultrasound-assisted extraction of phenolic compounds from strawberries prior to liquid chromatographic separation and photodiode array ultraviolet detection.", JOURNAL OF CHROMATOGRAPHY A, vol. 1100, 2005, pages 1 - 7, XP002498159 *
MATTHÄUS B: "Antioxidant activity of extracts obtained from residues of different oilseeds.", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 5 JUN 2002, vol. 50, no. 12, 5 June 2002 (2002-06-05), pages 3444 - 3452, XP002498158, ISSN: 0021-8561 *
WANG ET AL: "Recent advances in extraction of nutraceuticals from plants", TRENDS IN FOOD SCIENCE AND TECHNOLOGY, ELSEVIER SCIENCE PUBLISHERS, GB, vol. 17, no. 6, 1 June 2006 (2006-06-01), pages 300 - 312, XP005410730, ISSN: 0924-2244 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112980445A (zh) * 2021-03-26 2021-06-18 四川大学 一种从花椒油加工副产物中提取酚类抗氧化剂的方法

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Publication number Publication date
DE102007022662A1 (de) 2008-11-20

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