WO2022013282A1 - Procédé d'extraction de polyphénols - Google Patents

Procédé d'extraction de polyphénols Download PDF

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Publication number
WO2022013282A1
WO2022013282A1 PCT/EP2021/069588 EP2021069588W WO2022013282A1 WO 2022013282 A1 WO2022013282 A1 WO 2022013282A1 EP 2021069588 W EP2021069588 W EP 2021069588W WO 2022013282 A1 WO2022013282 A1 WO 2022013282A1
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WIPO (PCT)
Prior art keywords
leaves
polyphenols
process according
extract
previous
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PCT/EP2021/069588
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English (en)
Inventor
Alessio CAPPELLI
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Cappelli Alessio
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Publication of WO2022013282A1 publication Critical patent/WO2022013282A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/63—Oleaceae (Olive family), e.g. jasmine, lilac or ash tree
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine

Definitions

  • the present invention relates to a process which allows to obtain extracts having a high polyphenol content from leaves, preferably olive tree leaves, characterized by a drying stage of the olive tree leaves by microwave and by an extraction stage of the polyphenols in acidic aqueous solution.
  • the amount of OMWW generated vary according to the olive's type (and cultivar), the extraction system, and the process conditions.
  • concentrations of solutes are variable and depend on the type of cultivar, the ripeness of the fruit, and the crushing process.
  • their pollutant load expressed in terms of COD (Chemical Oxygen Demand)
  • COD Chemical Oxygen Demand
  • BOD Bio Oxygen Demand
  • the pollutant load of 1 m3 of OMWW corresponds to about 100-200 m3 of domestic waste.
  • the potential reuse of olive mill by-products and wastes has been investigated in several studies and researches for many years with the aim to reduce the pollutant load.
  • WO 2005/123603 provides a method for the treatment of OMWW generated by oil mills, in order to solve the problem of waste disposal and by-products reuse; the method includes an initial stage of OMWW acidification with 1% citric acid and subsequent stages of filtration.
  • This method represents a solid opportunity to reuse by-products and wastes of the olive oil industry, with a considerable environmental impact.
  • the acidification stage of OMWW cause the degradation of most oleuropein, which is present in a very low concentration in the final phenolic concentrates compared to hydroxytyrosol and tyrosol (see table A which shows the concentration in mg/ml of the main phenolic compounds in permeates and concentrates ( Pizzichini et al . ,2006).
  • Some methods involve the extraction of polyphenols from olive oil industry by-products with ethanol to enrich the oleuropein content of the final product.
  • US 10,258,660 discloses the extraction of oleuropein from olive leaves using ethanol.
  • the aim of the present invention is to provide an improved process for the extraction of polyphenols, notably oleuropein, from olive tree leaves, which allows to obtain higher amounts of oleuropein compared to the other methods available in the literature, with a degree of purity of at least 45% or higher and which does not employ alcoholic solvents.
  • polyphenols notably oleuropein
  • the present invention enables the achievement of this purpose with a relatively simple and low-cost approach.
  • the process of the present invention includes a first drying step of the olive tree leaves by microwave and a subsequent step of polyphenols extraction, preferably oleuropein, in an acidic aqueous solution.
  • polyphenols extraction preferably oleuropein
  • Figure 1 shows an HPLC chromatogram of an extract obtained according to a preferred form of the process of the invention from leaves of the cultivar Coratina;
  • Figure 2 shows an HPLC chromatogram obtained according to a preferred form of the process of the invention from leaves of cultivar Frantoio.
  • the process of the present invention comprises the following steps in succession: a) supply the leaves, preferably previously cleaned by washing and dryied to remove other waste materials b) drying the leaves by microwave drying c) pulverize the dried leaves d) extract the polyphenols from the dried and pulverized leaves by mixing the powdered leaves in an acidic aqueous solution e) recover the extract comprising polyphenols, in particular oleuropein.
  • the process is applicable to any type of leaf containing polyphenols; particularly preferred are the olive tree leaves.
  • olive tree leaves cultivars that might be used in the present invention, individually or in combination of two or more, include: Lucca, Mission, Nevadillo Blanco, Manzanillo, Amellenque, Arbequina, Ascolana Tenera, Ascolana, Azapa, Barnea, Barouni, Biancolilla, Bidh El Hamman, Blanqueta, Caillet Blanc, Carolea, Cayonne, Chemilali, Chitoni, Cipressino, Coratina, Cornicabra, Correggio, Correggiola, Cucco, Gigante di Cerignola, Frantoio, Glappolo, Gordal, Hardy's Mammoth, Hojiblanca, Itrana, Jumbo Kalamata, Kalamata, Koroneiki, Leccino, Leccio del Corno, Liani, Lucques, Manzanilla,
  • the microwave drying is carried out in a microwave oven at 350 - 900 W, more preferably at 600-800 W, for a time between 1 and 2.5 minutes.
  • the pulverization of the dried leaves can be carried out either by grinding the leaves manually, for example using a mortar, or mechanically, for example using a mill.
  • the temperature during the pulverization stage need to be controlled and kept about to room temperature.
  • the acidic aqueous solution used for the extraction have a pH between 2.5 and 5, more preferably about equal to 3.
  • the aqueous solution is acidified by the addition of a suitable amount of acid to the water.
  • the following acids can be used in the present invention: hydrochloric acid, hydrogen sulfide acid, sulfuric acid, sulfurous acid, phosphoric acid, nitric acid, hydroiodic acid, hydrobromic acid, perchloric acid, lactic acid, oxalic acid, tartaric acid, hydrofluoric acid, citric acid, ascorbic acid, acetic acid. More preferably, the aqueous solution is acidified by adding an appropriate amount of hydrochloric acid.
  • the aqueous solution is acidified without the addition of potentially toxic products, e.g. by adding an appropriate amount of citric acid.
  • the extraction step comprises the mixing of the dried leaf powder in the acidic aqueous solution, preferably for an extraction time between 2 and 8 hours, more preferably between 3 and 6 hours, at a controlled temperature, preferably between 30°C and 65°C, more preferably between 50°C and 65°C.
  • the extraction mixture comprising the dried leaf powder and the acidified water is kept in continuous agitation or mixed regularly during the extraction.
  • the ratio between leaves powder and acid solution is within 1:7 and 1:20, more preferably between 1:7 and 1:15.
  • the extract is recovered from the supernatant of the mixture including the dried leaf powder in acidic aqueous solution.
  • the recovery of the extract might be accomplished according to the methods reported in the literature.
  • the extract may be recovered by separating the liquid fraction of the extraction mixture, comprising the extracted polyphenols in suspension, from the solid fraction, including the leaves residues, using a fluted filter.
  • the liquid extract including polyphenols is thus preferably centrifuged and then filtered, in order to remove other undesired substances such as chlorophylls, to increase the degree of purity of the final extract.
  • the liquid fraction of the extraction mixture including the polyphenols is centrifuged within 5000 to 12000 rpm for a time preferably between 6 and 15 minutes. Once that centrifugation is completed, the supernatant is separated from the pellet and subjected to filtration, preferably with a filter having a pore size between 0.20 and 0.60 ⁇ m. The extracted polyphenols are thus recovered as a purified extract obtained as filtration permeate.
  • the extract including the polyphenols, optionally purified is freeze-dried, more preferably using a freeze-drying technique named "spray drying" which involves the use of a spray dryer.
  • This type of freeze- drying allows to further increase the degree of purity of the final extract, as well as to obtain a more stable final product which can be stored for longer periods of time compared to traditionally freeze-dried products obtained using standard equipment.
  • Extracts from olive leaves powder of Coratina and Frantoio cultivars were prepared according to a particularly preferred form of the method of the invention.
  • Olive leaves powder was obtained by drying the olive tree leaves in a microwave at 750 W for 2 minutes. Successively, the dried leaves were pulverized using a small mill. The temperature was kept within 35°C.
  • Polyphenols, particularly oleuropein were extracted from the leaves powder in a solution of distilled water acidified with 1 millimolar (mM) HC1 at pH 3. In particular, the dried olive leaves powder was mixed with the acidified water solution using a 1:10 ratio. Successively, the extraction was performed for approximately 4 hours at 60°C.
  • the extraction mixture was filtered using a fluted filter and, successively, the liquid permeate was centrifuged for 10 minutes at 12000 RPM. After centrifugation, the obtained supernatant was filtered using a filter with a pore size of 0.2 ⁇ m. Finally, the permeate was freeze-dried using a conventional freeze-dryer.
  • Table 1 shows the results obtained with the leaves of the two cultivars, assessing each extract with HPLC.
  • the amount of oleuropein was quantified in accordance with the HPLC obtained chromatograms which were compared with an analytical standard of oleuropein (Sigma-Aldrich) at 98% purity.
  • Capone R., Bilali, H. E., Debs, P., Cardone, G., &

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  • Health & Medical Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Medical Informatics (AREA)
  • Medicinal Chemistry (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Compounds Of Unknown Constitution (AREA)

Abstract

La présente invention concerne un procédé d'obtention d'extraits ayant une teneur élevée en polyphénols à partir de feuilles, de préférence à partir de feuilles d'olivier, caractérisé par une étape de séchage par micro-ondes des feuilles et une étape d'extraction des polyphénols en solution aqueuse acide.
PCT/EP2021/069588 2020-07-16 2021-07-14 Procédé d'extraction de polyphénols WO2022013282A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT102020000017338 2020-07-16
IT102020000017338A IT202000017338A1 (it) 2020-07-16 2020-07-16 Processo di estrazione di polifenoli

Publications (1)

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WO2022013282A1 true WO2022013282A1 (fr) 2022-01-20

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IT (1) IT202000017338A1 (fr)
WO (1) WO2022013282A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005123603A1 (fr) 2004-06-16 2005-12-29 Enea-Ente Per Le Nuove Tecnologie, L'energia E L'ambiente Procede de recuperation de composes de residus aqueux de moulins a huile d'olive utilisant des techniques membranaires
EP2338500A1 (fr) * 2009-12-23 2011-06-29 Phenofarm S.r.l. Procédé de production d'actifs concentrés et raffinés à partir de tissus et sous-produits d'Olea europaea avec des technologies de membrane
US10258660B2 (en) 2015-10-01 2019-04-16 Shodoshima Healthyland Co., Ltd. Olive leaf extract and method of producing the same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005123603A1 (fr) 2004-06-16 2005-12-29 Enea-Ente Per Le Nuove Tecnologie, L'energia E L'ambiente Procede de recuperation de composes de residus aqueux de moulins a huile d'olive utilisant des techniques membranaires
EP2338500A1 (fr) * 2009-12-23 2011-06-29 Phenofarm S.r.l. Procédé de production d'actifs concentrés et raffinés à partir de tissus et sous-produits d'Olea europaea avec des technologies de membrane
US10258660B2 (en) 2015-10-01 2019-04-16 Shodoshima Healthyland Co., Ltd. Olive leaf extract and method of producing the same

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
AOUIDI FATHIA ET AL: "Valorization of functional properties of extract and powder of olive leaves in raw and cooked minced beef meat : Effect of olive leaves on meat", vol. 97, no. 10, 19 January 2017 (2017-01-19), GB, pages 3195 - 3203, XP055790898, ISSN: 0022-5142, Retrieved from the Internet <URL:https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fjsfa.8164> DOI: 10.1002/jsfa.8164 *
CAPONE, R.BILALI, H. E.DEBS, P.CARDONE, G.DRIOUECH, N.: "Food system sustainability and food security: connecting the dots", JOURNAL OF FOOD SECURITY, vol. 2, no. 1, 2014, pages 13 - 22
FATMA HADRICH ET AL: "The [alpha]-Glucosidase and [alpha]-Amylase Enzyme Inhibitory of Hydroxytyrosol and Oleuropein", JOURNAL OF OLEO SCIENCE, vol. 64, no. 8, 1 August 2015 (2015-08-01), JP, pages 835 - 843, XP055281311, ISSN: 1345-8957, DOI: 10.5650/jos.ess15026 *
GIAMPIETRO, F.: "Quali modifiche al codice dell'ambiente", vol. 6, 2009, WOLTERS KLUWER, article "Commento alia direttiva 2008/98/CE sui rifiuti"
INCELLI, M.CORDINER, S.TOSTI, S.BORGOGNONI, F.SANSOVINI, M.SANTUCCI, A.: "Trattamento delle acque di vegetazione do oleifici: tecnologie a membrana e processi termochimici", CHIM. IND, vol. 3, 2016
KAMRAN M.HAMLIN A. S.SCOTT C. J.HASSAN K.: "Obied Drying at high temperature for a short time maximizes the recovery of olive leaf biophenols", INDUSTRIAL CROPS AND PRODUCTS, vol. 78, 2015, pages 29 - 38, XP029324646, DOI: 10.1016/j.indcrop.2015.10.031
ROSE, G.: "International Law of Sustainabel Agriculture in the 21st Century: The International Treaty on Plant Genetic Resources for Food and Agriculture", GEO. INT'L ENVTL. L. REV., vol. 15, 2002, pages 583
SAHIN SELIN ET AL: "Effect of drying method on oleuropein, total phenolic content, flavonoid content, and antioxidant activity of olive ( Olea europaea ) leaf", vol. 42, no. 5, 13 February 2018 (2018-02-13), TRUMBULL, CT, US, pages e13604, XP055791234, ISSN: 0145-8892, Retrieved from the Internet <URL:https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1111%2Fjfpp.13604> DOI: 10.1111/jfpp.13604 *

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