[go: up one dir, main page]

WO1999020587A8 - Procede d'extraction et de purification de la luteine, de la zeaxanthine et de carotenoides rares dans les fleurs et plantes de tagete - Google Patents

Procede d'extraction et de purification de la luteine, de la zeaxanthine et de carotenoides rares dans les fleurs et plantes de tagete

Info

Publication number
WO1999020587A8
WO1999020587A8 PCT/US1998/022229 US9822229W WO9920587A8 WO 1999020587 A8 WO1999020587 A8 WO 1999020587A8 US 9822229 W US9822229 W US 9822229W WO 9920587 A8 WO9920587 A8 WO 9920587A8
Authority
WO
WIPO (PCT)
Prior art keywords
lutein
zeaxanthin
plants
carotenoids
berries
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US1998/022229
Other languages
English (en)
Other versions
WO1999020587A1 (fr
Inventor
Frederick Khachik
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
OFFICE OF TECHNOLOGY LIAISON
TECHNOLOGY LIAISON OFF OF
Original Assignee
OFFICE OF TECHNOLOGY LIAISON
TECHNOLOGY LIAISON OFF OF
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 OFFICE OF TECHNOLOGY LIAISON, TECHNOLOGY LIAISON OFF OF filed Critical OFFICE OF TECHNOLOGY LIAISON
Priority to AU12719/99A priority Critical patent/AU1271999A/en
Priority to US09/529,815 priority patent/US6262284B1/en
Publication of WO1999020587A1 publication Critical patent/WO1999020587A1/fr
Publication of WO1999020587A8 publication Critical patent/WO1999020587A8/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0096—Purification; Precipitation; Filtration
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

L'invention concerne un procédé qui permet, simultanément, d'extraire, de saponifier et d'isoler la lutéine et la zéaxanthine, ainsi qu'une combinaison de plusieurs caroténoïdes rares, avec une pureté élevée, dans des plantes, sans utiliser de solvants organiques nocifs. On a recueilli des cristaux de lutéine renfermant 5 % de zéaxanthine dans des pétales séchés de fleurs de tagète (Tagete erecta), la zéaxanthine étant isolée et purifiée à partir de baies de Lycium chinese Mill (LCM). On a utilisé le même procédé pour isoler et purifier un mélange de lutéine, de bêta-carotène, de néoxanthine, de violaxanthine et d'époxyde de lutéine à partir de végétaux verts (de préférence, chou fourrager, chou rosette et épinards). Dans une moindre mesure, ces végétaux ont également été la source de plusieurs caroténoïdes rares comme l'alpha-cryptoxanthine (tagète) et la bêta-cryptoxanthine (baies de LCM). Le procédé fait appel à une combinaison de tétrahydrofurane (THF), de solution alcoolique de potassium ou d'hydroxyde de sodium, à température ambiante et en conditions douces, pour déclencher quantitativement dans un délai de deux heures l'hydrolyse en formes libres des esters d'acides gras de la lutéine et de la zéaxanthine dans les fleurs de tagète et les baies de LCM. S'agissant des végétaux verts, qui contiennent la lutéine sous forme libre, l'opération simultanée d'extraction et d'hydrolyse permet d'éliminer rapidement les chlorophylles indésirables. Après filtration, on laisse évaporer le THF et l'alcool, et on soumet le résidu à un lavage séquentiel à l'eau et à l'alcool de manière à éliminer le THF, la base, et dans le cas de végétaux verts, les chlorophylles et leurs dérivés. Les cristaux de lutéine et de zéaxanthine résultants, issus de leurs sources végétales respectives, sont purs à environ 70 %, et on peut les purifier plus avant, soit par recristallisation, soit par injection de leur mise en solution de THF/eau dans une colonne à gel de silice N. On peut obtenir comme sous-produits des dernières étapes de purification mentionnées plusieurs caroténoïdes rares comme l'anhydrolutéine et l'alpha-cryptoxanthine (à partir des tagètes) et la bêta-cryptoxanthine (à partir de baies de LCM). Les caroténoïdes purifiés isolés selon le procédé décrit sont dépourvus d'impuretés et constituent une source de suppléments nutritifs sans risques pour la consommation humaine, fournissant par ailleurs des colorants pour les aliments destinés à la consommation humaine.
PCT/US1998/022229 1997-10-21 1998-10-21 Procede d'extraction et de purification de la luteine, de la zeaxanthine et de carotenoides rares dans les fleurs et plantes de tagete Ceased WO1999020587A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU12719/99A AU1271999A (en) 1997-10-21 1998-10-21 Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants
US09/529,815 US6262284B1 (en) 1998-10-21 1998-10-21 Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US6257297P 1997-10-21 1997-10-21
US60/062,572 1997-10-21
US7836098P 1998-03-18 1998-03-18
US60/078,360 1998-03-18

Publications (2)

Publication Number Publication Date
WO1999020587A1 WO1999020587A1 (fr) 1999-04-29
WO1999020587A8 true WO1999020587A8 (fr) 1999-08-26

Family

ID=26742423

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/022229 Ceased WO1999020587A1 (fr) 1997-10-21 1998-10-21 Procede d'extraction et de purification de la luteine, de la zeaxanthine et de carotenoides rares dans les fleurs et plantes de tagete

Country Status (2)

Country Link
AU (1) AU1271999A (fr)
WO (1) WO1999020587A1 (fr)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CA2396167C (fr) 2000-01-27 2010-01-26 Dsm N.V. Isolation de cristaux de carotenoide
US6818798B1 (en) 2000-05-03 2004-11-16 University Of Maryland, College Park Process for making a (3R,3′R)-zeaxanthin precursor
US6329557B1 (en) 2000-06-09 2001-12-11 Prodemex, S.A. De C.V. Purification of xanthophylls from marigold extracts that contain high levels of chlorophylls
US7119238B2 (en) 2000-07-12 2006-10-10 University Of Maryland Process for purification and crystallization of palm oil carotenoids
DE60108879T2 (de) 2000-07-27 2006-04-06 University Of Maryland College Park Verfahren zur herstellung von seltenen carotinoiden ausgehend von handelsüblichem lutein
JP2002218994A (ja) * 2001-01-26 2002-08-06 Fuji Chem Ind Co Ltd 粗キサントフィル類の精製法
WO2002060864A1 (fr) * 2001-01-30 2002-08-08 Sabinsa Corporation Procede permettant d'obtenir des compositions de luteine stable et des derives de luteine
US6784351B2 (en) * 2001-06-29 2004-08-31 Ball Horticultural Company Targetes erecta marigolds with altered carotenoid compositions and ratios
US7575766B2 (en) * 2001-06-29 2009-08-18 Ball Horticultural Company Tagetes erecta with altered carotenoid compositions and ratios
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
CA2474646C (fr) 2002-02-06 2011-04-26 University Of Maryland, College Park Procede de production de .beta.-cryptoxanthine et .alpha.-cryptoxanthine a partir de luteine du commerce
US6737535B2 (en) 2002-06-05 2004-05-18 Kancor Flavours And Extracts Limited Trans-lutein enriched xanthophyll ester concentrate and a process for its preparation
EP1371641A1 (fr) * 2002-06-10 2003-12-17 Adisseo France S.A.S. Procédé de préparation et isolement de cristaux caroténoides
US6743953B2 (en) 2002-08-26 2004-06-01 Kancor Flavours & Extracts Ltd. Process for the preparation of xanthophyll crystals
US7351424B2 (en) 2004-07-22 2008-04-01 Bio Lut S.A. De C.V. Enhanced purity trans-lutein-ester compositions and methods of making same
EP1974049A2 (fr) 2004-12-17 2008-10-01 Metanomics GmbH Procédé de contrôle de production de produits chimiques fins
ATE483684T1 (de) * 2005-04-25 2010-10-15 Katra Phytochem Private Ltd Isolierung und aufreinigung von carotenoiden aus ringelblumenblüten
CN100368395C (zh) * 2006-05-17 2008-02-13 浙江医药股份有限公司新昌制药厂 从万寿菊油树脂中分离提纯高含量叶黄素脂肪酸酯的方法
CN101402597A (zh) * 2008-10-31 2009-04-08 南京泛成生物化工有限公司 叶黄素提取工艺
CN102174005A (zh) * 2011-01-25 2011-09-07 石河子大学医学院第一附属医院 一种从万寿菊干花中提取叶黄素的方法
TWI466709B (zh) * 2011-07-20 2015-01-01 Nat Univ Chung Hsing From the original berry Wolfberry a liquid - liquid freezing method for separation of high purity theaflavins palmitate Maize
CN102558008A (zh) * 2011-09-08 2012-07-11 黑龙江省嘉宝生物技术开发有限公司 一种叶黄素的制备方法
CN103091446B (zh) * 2013-01-31 2015-12-23 甘肃省农垦农业研究院 叶黄素酯皂化程度快速测定方法
CN103275088A (zh) * 2013-05-30 2013-09-04 湖南炎帝生物工程有限公司 从念珠藻中分离叶绿素a与类胡萝卜素的方法
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
CN103992256B (zh) * 2014-05-17 2016-09-07 昆明涞章医药科技有限公司 一种从金盏菊中制备高纯度叶黄素酯的方法
CN105503681A (zh) * 2014-09-25 2016-04-20 赵军 高纯度枸杞玉米黄质棕榈酸酯的制备方法
CN104447467A (zh) * 2014-10-30 2015-03-25 蒋小春 一种提取枸杞中类胡萝卜素的方法
CN105017116A (zh) * 2015-07-31 2015-11-04 江西恩泉油脂有限公司 一种叶黄素浸膏的皂化工艺
CN107082756B (zh) * 2017-03-17 2018-11-23 晨光生物科技集团股份有限公司 一种叶黄素晶体的工业制备方法
CN114401775B (zh) * 2019-07-26 2023-11-07 卡利亚里大学 从果实中分离有色体类胡萝卜素
CN110563625B (zh) * 2019-09-29 2020-07-31 山东天音生物科技有限公司 一种由万寿菊油树脂分离纯化玉米黄质的方法
CN110835315A (zh) * 2019-10-28 2020-02-25 百瑞源枸杞股份有限公司 一种枸杞红素的制备方法
KR102161387B1 (ko) * 2019-12-09 2020-09-29 대한켐텍 주식회사 루테인 포함 피부건강용 조성물 및 이를 포함하는 피부건강기능식품

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4048203A (en) * 1976-12-06 1977-09-13 Thomas Philip Purification of lutein-fatty acid esters from plant materials
US5382714A (en) * 1994-03-17 1995-01-17 The Catholic University Of America Process for isolation, purification, and recrystallization of lutein from saponified marigold oleoresin and uses thereof
US5648564A (en) * 1995-12-21 1997-07-15 Kemin Industries, Inc. Process for the formation, isolation and purification of comestible xanthophyll crystals from plants

Also Published As

Publication number Publication date
WO1999020587A1 (fr) 1999-04-29
AU1271999A (en) 1999-05-10

Similar Documents

Publication Publication Date Title
WO1999020587A8 (fr) Procede d'extraction et de purification de la luteine, de la zeaxanthine et de carotenoides rares dans les fleurs et plantes de tagete
EP0904258A4 (fr)
DK1534673T3 (en) Improved method of making xanthophyll crystals
AU2002329028B2 (en) Carotenoid extraction process
US5382714A (en) Process for isolation, purification, and recrystallization of lutein from saponified marigold oleoresin and uses thereof
AU2002234248A1 (en) Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants
JP2014529607A (ja) 天然物質からルテイン／キサントフィルを抽出する方法、並びにこの方法により得られる高度精製ルテイン／キサントフィル
EP1513804B2 (fr) Nouveau concentre d'esters de xanthophylle enrichi en trans-luteine et procede servant a la preparation de ce concentre
US20050139145A1 (en) Process for the formation and isolation of carotenoid crystals
Britton et al. The occurrence of phytoene 1, 2-oxide and related carotenoids in tomatoes
US7629007B2 (en) Process for purification of free xanthophylls
Deli et al. Isolation and characterization of 3, 5, 6-trihydroxy-carotenoids from petals of Lilium tigrinum
WO2002060865A1 (fr) Procede d'obtention de zeaxanthine, de cryptoxanthine & d'autres carotenoides de grande purete a partir de piments byadagi/chappatta et composition carotenoide
US7875751B2 (en) Method for the purification of carotenoids from plant extracts and the products so obtained
Matsuno et al. Comparative biochemical studies of carotenoids in fishes—XXIX. Isolation of new luteins, lutein F and lutein G from marine fishes
松野隆男 et al. Carotenoids of shellfishes-VII. Carotenoids of the spindle shell Fusinus perplexus.
Molnár et al. Preparation and (E/Z)‐Isomerization of the Diastereoisomers of Violaxanthin
松野隆男 et al. Comparative biochemical studies of carotenoids in fishes. XXVI. Isolation of lactucaxanthin from tilapia Tilapia nilotica.
EP2196207B1 (fr) Procédé de purification de caroténoïdes à base d'extraits végétaux et produits ainsi obtenus
CN114369050B (zh) 一种叶黄素酯的制备方法
KR20050016445A (ko) 카로티노이드 결정의 형성 및 분리 방법

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE GH HU IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
AK Designated states

Kind code of ref document: C1

Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE GH HU IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZW

AL Designated countries for regional patents

Kind code of ref document: C1

Designated state(s): GH GM KE LS MW SD SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

CFP Corrected version of a pamphlet front page

Free format text: REVISED ABSTRACT RECEIVED BY THE INTERNATIONAL BUREAU AFTER COMPLETION OF THE TECHNICAL PREPARATIONS FOR INTERNATIONAL PUBLICATION

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWE Wipo information: entry into national phase

Ref document number: 09529815

Country of ref document: US

NENP Non-entry into the national phase in:

Ref country code: KR

WWE Wipo information: entry into national phase

Ref document number: PA/A/2000/004012

Country of ref document: MX

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase in:

Ref country code: CA