WO2012025591A1 - Procédé pour la fabrication d'un extrait hautement enrichi contenant de la zéaxanthine et/ou ses esters - Google Patents

Procédé pour la fabrication d'un extrait hautement enrichi contenant de la zéaxanthine et/ou ses esters Download PDF

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Publication number
WO2012025591A1
WO2012025591A1 PCT/EP2011/064630 EP2011064630W WO2012025591A1 WO 2012025591 A1 WO2012025591 A1 WO 2012025591A1 EP 2011064630 W EP2011064630 W EP 2011064630W WO 2012025591 A1 WO2012025591 A1 WO 2012025591A1
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Prior art keywords
range
process according
zeaxanthin
temperature
esters
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PCT/EP2011/064630
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English (en)
Inventor
Axel Buss
Max Hugentobler
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Dsm Ip Assets B.V.
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Priority to CN201180040778.XA priority Critical patent/CN103080238B/zh
Publication of WO2012025591A1 publication Critical patent/WO2012025591A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
    • 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
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
    • A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
    • A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
    • A23L5/44—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives using carotenoids or xanthophylls

Definitions

  • Wolfberry - commercially called Goji berry - is the common name for the fruit of two very closely related species: Lycium barbarum and Lycium chinense, two species of box- thorn.
  • Goji berries have the highest content of zeaxanthin of all known food sources.
  • the berries have been cultivated in China for decades and are used as food and in Traditional Chinese Medicine.
  • the content of carotenoids in goji berries can range from 600 to 900 ppm.
  • the main carotenoid is zeaxanthin in its natural ester form.
  • the inventors of the present invention have now succeeded in developing a process for the extraction of the dried berries with a lipophilic solvent and obtained in high yield an oily oleoresin, rich in zeaxanthin (6 - 12 weight-% content).
  • zeaxanthin dipalmitate containing oleoresin could be saponified with caustic in ethanol to give a powder in 70% yield and with a zeaxanthin content of 75 %.
  • the present invention is directed to a process for the manufacture of an extract of Goji berries containing zeaxanthin and/or its esters, comprising the following steps:
  • step b) extracting the smaller Goji berries obtained in step a) with a solvent selected from the group consisting of ethyl acetate, hexane, heptane, petroleum ether and mixtures thereof; and
  • the process according to the present invention consists only of these steps a) to e) and does not comprise any additional steps.
  • a preferred embodiment of the present invention is a process for the manufacture of an extract of Goji berries containing zeaxanthin and/or its esters, consisting of the following steps:
  • step b) extracting the smaller Goji berries obtained in step a) with a solvent selected from the group consisting of ethyl acetate, hexane, heptane, petroleum ether and mixtures thereof; and
  • step c) removing the solvent from the extracts obtained in step b); and d) optionally cleaving the esters in the dried extracts obtained in step c); and e) crystallizing the dried extracts obtained in step c) or d) in an aliphatic straight or branched C 1-4 alcohol.
  • one of these preferred embodiments is directed to a process for the manufacture of an extract of Goji berries containing zeaxanthin (di)esters consisting of the following steps:
  • the other preferred embodiment is directed to a process for the manufacture of an extract of Goji berries containing zeaxanthin consisting of the following steps: - obtaining reduced sized pieces of dried Goji berries; and
  • CN-A 1 158 263 e.g. uses an extraction solvent which contains water, so that also the sugars contained in the berries are extracted.
  • the process according to CN-A 1 086 730 focuses on the preservation of the natural nutritious components and special flavour of the Goji berries.
  • the aim of the process of US 2008/0124416 is to obtain an extract rich in polysaccharides and in carotenoids, so that an extraction step with water is mandatory, whereas the aim of the present invention is to obtain an extract highly enriched in zeaxanthin and preferably in the form of a powder and not a paste, since powders are much more easily manageable.
  • a further advantage of the present invention is that the process of the present invention can be used in industrial scale to obtain natural zeaxanthin and/or its esters, especially its dipalmitate esters, in a large amount (especially in an amount of several tons).
  • the process of the present invention is now described in more detail.
  • steps a) to e) of the processes according to the present invention are performed under an inert gas atmosphere such as e.g. under nitrogen or argon or mixtures thereof.
  • the Goji berries used can either be of the species Lycium barbarum and/or of the species Lycium chinense.
  • zeaxanthin esters encompasses zeaxanthin monoesters, as well as zeaxanthin diesters. In Goji berries the zeaxanthin esters are found mainly in form of their dipalmitate diesters.
  • oleoresin When only steps a), b) and c) of the processes according to the present invention are performed, a so-called “oleoresin” is obtained.
  • the consistence of this oleoresin is pasty-like at room- temperature, and it mainly consists of lipophilic compounds such as fats.
  • the content of zeaxanthin in form of its esters in this oleoresin is usually in the range of 11 to 23 weight-%, based on the total weight of the oleoresin.
  • an extract which has a zeaxanthin(di)ester content in the range of 25 to 80 weight-%, preferably a zeaxanthin(di)ester content in the range of 30 to 70 weight-%, more preferably a zeaxanthin(di)ester content in the range of 40 to 65 weight- %, based on the total weight of the extract.
  • This extract is pulverous which makes its handling very easy.
  • an extract which has a zeaxanthin content in the range of 30 to 90 weight-% in form of free zeaxanthin, preferably a zeaxanthin content in the range of 45 to 90 weight-% in form of free zeaxanthin, more preferably a zeaxanthin content in the range of 60 to 90 weight-% in form of free zeaxanthin, based on the total weight of the extract.
  • This extract is pulverous which makes its handling also very easy.
  • the extracts obtained by the processes according to the present invention can be used as food supplements e.g. for eye health. Furthermore the extracts and food supplements containing them may be used as antioxidants and/or blue light absorber.
  • the Goji berries are usually commercially available in dried form.
  • the drying can be carried out by any method known to the person skilled in the art such as by sunshine drying or by oven drying.
  • the dried Goji berries used in step a) have a water content in the range of 3 to 10 weight-%, preferably in the range of 5 to 7 weight-%, based on the total weight of the Goji berries.
  • Preferred extraction solvents used in step b) are a mixture of ethyl acetate and hexane in a volume ratio of 1 : 1, ethyl acetate alone and hexane alone.
  • the most preferred extraction solvent is ethyl acetate.
  • the amount of solvent used in step b) is in the range of 1 to 5 liters, more preferably in the range of 1 to 4 liters, even more preferably in the range of 1 to 3 liters, most preferably in the range of 1.5 to 2.5 liters, per 1 kg of size reduced dried Goji berries obtained in step a).
  • step b) is performed at a temperature in the range of 20 °C to 80 °C, more preferably at a temperature in the range of 20 °C to 65 °C, even more preferably at a temperature in the range of 22 °C to 55 °C, most preferably at a temperature in the range of 40 °C to 50 °C.
  • Preferred embodiments of the present invention are also embodiments where several preferred embodiments of step b) as listed above are combined.
  • the solvent of the extract is evaporated under reduced pressure, preferably at a temperature in the range of 20 °C to 60 °C, more preferably at a temperature in the range of 30 °C to 60 °C, most preferably at a temperature in the range of 35 °C to 50 °C, whereby an "oleoresin" is obtained.
  • the solvent may be removed batch wise, continuously or in a serial manner.
  • Preferred embodiments of the present invention are also embodiments where several preferred embodiments of step c) as listed above are combined.
  • a base such as KOH and/or NaOH
  • the oleoresin has to be treated with a base, such as KOH and/or NaOH, to cleave the esters. If this is done with an aqueous base zeaxanthin is obtained together with fatty acid salts (saponification). If this is done with a base (for example with solid KOH and/or solid NaOH) in an aliphatic straight or branched C 1-4 alcohol zeaxanthin is obtained together with fatty acid esters (trans-esterification).
  • a base for example with solid KOH and/or solid NaOH
  • the cleavage of the zeaxanthin esters in step d) can be performed by saponification or trans-esterification of the zeaxanthin esters of the dried extracts obtained in step c).
  • the cleavage of the zeaxanthin esters is performed by trans-esterification. More preferably this trans-esterification in step d) is performed at a temperature in the range of 20 °C to 150 °C, preferably at a temperature in the range of 60 °C to 100 °C, more preferably at a temperature in the range of 70 °C to 90 °C.
  • the reaction can be performed at ambient pressure or at a higher pressure depending on the temperature chosen.
  • trans-esterification is performed by reaction of the zeaxanthin esters with an aliphatic straight or branched C 1-4 alcohol in the presence of a base.
  • Examples of the aliphatic straight or branched C 1-4 alcohol are methanol, ethanol, iso- propanol, n-propanol, n-butanol, iso-butanol and tert-butanol.
  • Preferred alcohols are methanol and ethanol and any mixture thereof. The most preferred alcohol is ethanol.
  • the amount of said alcohol is in the range of 5 to 30 liter per kg of dried extract, more preferably in the range of 5 to 25 liter per kg of dried extract, most preferably in the range of 5 to 20 liter per kg of dried extract.
  • bases are alkali metal hydroxides such as KOH and NaOH and any mixtures thereof.
  • the amount of said base is in the range of stoichiometrical or catalytic amounts.
  • Preferred embodiments of the present invention are also embodiments where several preferred embodiments of step d) as listed above are combined.
  • step e) is performed at a tempera- ture in the range of room temperature to 78 °C, more preferably at a temperature in the range of 40 °C to 60 °C, most preferably at a temperature around 50 °C.
  • the amount of ethanol used in step e) is preferably in the range of 1 to 10 liter, more preferably the amount of ethanol used in step e) is in the range of 2 to 7 liter, most preferably the amount of ethanol used in step e) is in the range of 3 to 5 liter, per 1 kg of dried extract obtained in step c).
  • Preferred embodiments of the present invention are also embodiments where several preferred embodiments of step e) as listed above are combined.
  • step a) and/or step b) and/or step c) and/or step d) and/or step e) are combined.
  • the most preferred embodiment of the present invention is a process for the manufacture of an extract of Goji berries containing zeaxanthin, with a zeaxanthin content of at least 60 weight-%, based on the total weight of the extract, consisting of the following steps:
  • step a) obtaining reduced sized pieces of dried Goji berries with a water content of 3 to 10 weight-%, based on the total weight of the Goji berries; and b) extracting the smaller Goji berries obtained in step a) with ethyl acetate at a temperature in the range of 40 °C to 50 °C; and
  • step c) removing the solvent from the extracts obtained in step b); and d) cleaving the esters in the dried extracts obtained in step c) by transesterifi- cation with ethanol in the presence of a base;
  • step d) crystallizing the dried extracts obtained in step d) in ethanol.
  • Example 1 Influence of the Milling on the Extraction Yield of Zeaxanthin
  • two extractions were performed using either the whole berries or the milled berries as starting materials under exactly the same extraction conditions (200 g berries, 3 x 500 ml hexane, 45 °C for 1 hour, respectively). From the extraction of the whole berries 630 mg of a red oleoresin was obtained with a zeaxanthin content of 12.4 weight-%, corresponding to 78 mg zeaxanthin.
  • Example 3 Extraction of zeaxanthin from Goji berries to prepare an oleoresin with less amount of ethyl acetate used than in example 2.1
  • Goji-berries were milled using a food processor. 200 g of the pulverized berries were then transferred to a 1500 ml-flask and treated with 400 ml of ethyl acetate. The mixture was stirred at 45 °C for 1 hour under an inert gas atmosphere. The mixture was filtered and the solvent was evaporated under reduced pressure. 1.27 g of a red oleoresin were obtained which content of zeaxanthin was measured by HPLC and is given in Table 3 below.
  • Example 4 Extraction of zeaxanthin from Goji berries to prepare an oleoresin with less amount of hexane than in example 2.3
  • Goji-berries were milled using a food processor. 200 g of the pulverized berries were then transferred to a 1500 ml-flask and treated with 400 ml of hexane. The mixture was stirred at 45 °C for 1 hour under an inert gas atmosphere. Subsequently, the mixture was filtered and the solvent of the filtrate was evaporated under reduced pressure.
  • the residue was extracted 2 further times following the same procedure, i.e. a total of 1.2 liter of hexane was used for the extraction.
  • a total of 2.68 g of a red oleoresin was obtained with a zeaxanthin amount of 95.1 mg corresponding to a zeaxanthin content of 35.5 g per kg of oleoresin.
  • Example 5 Repetition of example 4 with less amount of Goji berries
  • Goji-berries were milled using a food processor. 100 g of the pulverized berries were then transferred to a 750 ml-flask and treated with 200 ml of hexane. The mixture was stirred at 45 °C for 1 hour. Subsequently, the mixture was filtered and the solvent was evaporated under reduced pressure. The residue was extracted 2 further times following the same procedure. 1.04 g of a red oleoresin were obtained with an amount of zeaxanthin of 106 mg corresponding to a ze- axanthin content of 102 g per kg of oleoresin.
  • Example 6 Extraction of zeaxanthin from Goji berries to prepare an oleoresin at room temperature
  • Goji berries were milled using a food processor. 100 g of the pulverized berries were then transferred to a 750 ml-flask and treated with 200 ml of hexane. The mixture was stirred at 23 °C for 1 hour. Subsequently, the mixture was filtered and the solvent was evapo- rated under reduced pressure.
  • Example 7 Extraction of zeaxanthin from Goji berries to prepare an oleoresin at 65 °C
  • Goji berries were milled using a food processor. 100 g of the pulverized berries were then transferred to a 750 ml-flask and treated with 200 ml of hexane. The mixture was stirred at 65 °C for 1 hour. Subsequently, the mixture was filtered and the solvent was evaporated under reduced pressure.
  • Example 8 Purification of the oleoresin by crystallisation in ethanol to prepare a natural zeaxanthin enriched powder
  • the extraction process could be successfully scaled-up. Batches of 4 kg of Goji berries were milled and extracted 3 times with either 10 liters of hexane or ethyl acetate, respectively. In total 68 kg of dried goji berries were extracted.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
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  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Botany (AREA)
  • Mycology (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

La présente invention concerne un procédé pour la fabrication d'un extrait de baies de lyciet contenant de la zéaxanthine et/ou ses esters, comprenant les étapes suivantes : a) obtention de morceaux de taille réduite de baies de lyciet séchées ; et b) extraction des baies de lyciet plus petites obtenues dans l'étape a) avec un solvant sélectionné parmi le groupe constitué de l'acétate d'éthyle, l'hexane, l'heptane, l'éther de pétrole et des mélanges de ceux-ci ; et c) élimination du solvant des extraits obtenus dans l'étape b) ; et d) clivage facultatif des esters dans les extraits séchés obtenus dans l'étape c) ; et e) cristallisation des extraits séchés obtenus dans l'étape c) ou d) dans un alcool aliphatique à chaîne droite ou ramifiée en C1-4. De préférence, le procédé selon la présente invention consiste seulement en les étapes a) à e) données ci-dessus.
PCT/EP2011/064630 2010-08-25 2011-08-25 Procédé pour la fabrication d'un extrait hautement enrichi contenant de la zéaxanthine et/ou ses esters WO2012025591A1 (fr)

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CN201180040778.XA CN103080238B (zh) 2010-08-25 2011-08-25 用于制造含玉米黄质和/或其酯的高富集萃取物的方法

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013127255A1 (fr) * 2012-02-27 2013-09-06 Dsm Ip Assets B.V. Procédé de fabrication d'extrait hautement enrichi contenant de la zéaxanthine et/ou ses esters

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104803901A (zh) * 2014-01-27 2015-07-29 中国科学院大连化学物理研究所 一种原位富集制备天然玉米黄素制备的方法
CN106699625B (zh) * 2017-01-11 2018-09-11 上海璞菁生物科技有限公司 从枸杞渣粕中制备玉米黄质的方法
CN110892987A (zh) * 2017-11-05 2020-03-20 周学义 一种枸杞糖浆的制备方法

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CN1086730A (zh) 1993-08-09 1994-05-18 高海涛 枸杞精细粉、枸杞清油及其生产方法
WO1997023436A1 (fr) 1995-12-21 1997-07-03 Kemin Foods, L.C. Procede de formation, d'isolement et de purification de cristaux de xanthophylle comestibles dans des vegetaux
CN1158263A (zh) 1996-11-29 1997-09-03 高海涛 一种可提高有机溶剂回收率的纯化枸杞的方法
US6191293B1 (en) 1998-04-20 2001-02-20 Inexa, Industria Extractora C.A. Trans-xanthophyll ester concentrates of enhanced purity and methods of making same
WO2003048284A1 (fr) * 2001-11-29 2003-06-12 University Of Maryland Procede d'extraction et de purification de luteine, de zeaxanthine et de carotenoides rares a partir de fleurs et de plantes de marigold
US20070161826A1 (en) 2005-12-19 2007-07-12 Pena Gustavo R Process for purification of free xanthophylls
US20080124416A1 (en) 2006-11-28 2008-05-29 Renaissance Herbs, Inc. Therapeutic composition from goji (lycium barbarum l.), methods of making and using
WO2009027850A2 (fr) * 2007-06-06 2009-03-05 Multi-Tech Specialty Chemicals Co., Ltd. Procédé de préparation de cristaux de xanthophylle

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WO2002094772A1 (fr) * 2001-05-18 2002-11-28 Aventis Animal Nutrition S.A. Procede pour extraire des esters de xanthophylle et de carotenoides
US6797303B2 (en) * 2001-09-04 2004-09-28 Lycored Natural Products Industries Ltd. Carotenoid extraction process

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Publication number Priority date Publication date Assignee Title
CN1086730A (zh) 1993-08-09 1994-05-18 高海涛 枸杞精细粉、枸杞清油及其生产方法
WO1997023436A1 (fr) 1995-12-21 1997-07-03 Kemin Foods, L.C. Procede de formation, d'isolement et de purification de cristaux de xanthophylle comestibles dans des vegetaux
US5648564A (en) * 1995-12-21 1997-07-15 Kemin Industries, Inc. Process for the formation, isolation and purification of comestible xanthophyll crystals from plants
CN1158263A (zh) 1996-11-29 1997-09-03 高海涛 一种可提高有机溶剂回收率的纯化枸杞的方法
US6191293B1 (en) 1998-04-20 2001-02-20 Inexa, Industria Extractora C.A. Trans-xanthophyll ester concentrates of enhanced purity and methods of making same
WO2003048284A1 (fr) * 2001-11-29 2003-06-12 University Of Maryland Procede d'extraction et de purification de luteine, de zeaxanthine et de carotenoides rares a partir de fleurs et de plantes de marigold
US20050038271A1 (en) 2001-11-29 2005-02-17 Frederick Khachik Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants
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WO2009027850A2 (fr) * 2007-06-06 2009-03-05 Multi-Tech Specialty Chemicals Co., Ltd. Procédé de préparation de cristaux de xanthophylle

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013127255A1 (fr) * 2012-02-27 2013-09-06 Dsm Ip Assets B.V. Procédé de fabrication d'extrait hautement enrichi contenant de la zéaxanthine et/ou ses esters

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