AU2006213635B2 - A Capsicum variety exhibiting a hyper-accumulation of zeaxanthin and products derived therefrom - Google Patents

A Capsicum variety exhibiting a hyper-accumulation of zeaxanthin and products derived therefrom Download PDF

Info

Publication number
AU2006213635B2
AU2006213635B2 AU2006213635A AU2006213635A AU2006213635B2 AU 2006213635 B2 AU2006213635 B2 AU 2006213635B2 AU 2006213635 A AU2006213635 A AU 2006213635A AU 2006213635 A AU2006213635 A AU 2006213635A AU 2006213635 B2 AU2006213635 B2 AU 2006213635B2
Authority
AU
Australia
Prior art keywords
zeaxanthin
plant
derived
capsicum
oleoresin
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
AU2006213635A
Other languages
English (en)
Other versions
AU2006213635A1 (en
Inventor
James P. Barren
Donald R. Berdahl
Jeffrey S. Kanel
Carol L. Locey
Paul H. Todd
Anthony P. Vandenhombergh
Carrie K. Young
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.)
Kalamazoo Holdings Inc
Original Assignee
Kalamazoo Holdings Inc
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 Kalamazoo Holdings Inc filed Critical Kalamazoo Holdings Inc
Publication of AU2006213635A1 publication Critical patent/AU2006213635A1/en
Application granted granted Critical
Publication of AU2006213635B2 publication Critical patent/AU2006213635B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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)
    • A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/12—Ophthalmic agents for cataracts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
    • C12N15/79—Vectors or expression systems specially adapted for eukaryotic hosts
    • C12N15/82—Vectors or expression systems specially adapted for eukaryotic hosts for plant cells, e.g. plant artificial chromosomes (PACs)
    • C12N15/8241—Phenotypically and genetically modified plants via recombinant DNA technology
    • C12N15/8242—Phenotypically and genetically modified plants via recombinant DNA technology with non-agronomic quality (output) traits, e.g. for industrial processing; Value added, non-agronomic traits
    • C12N15/8257—Phenotypically and genetically modified plants via recombinant DNA technology with non-agronomic quality (output) traits, e.g. for industrial processing; Value added, non-agronomic traits for the production of primary gene products, e.g. pharmaceutical products, interferon
    • C12N15/8258—Phenotypically and genetically modified plants via recombinant DNA technology with non-agronomic quality (output) traits, e.g. for industrial processing; Value added, non-agronomic traits for the production of primary gene products, e.g. pharmaceutical products, interferon for the production of oral vaccines (antigens) or immunoglobulins

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Biomedical Technology (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Microbiology (AREA)
  • General Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Ophthalmology & Optometry (AREA)
  • Immunology (AREA)
  • Botany (AREA)
  • Epidemiology (AREA)
  • Medical Informatics (AREA)
  • Cell Biology (AREA)
  • Physics & Mathematics (AREA)
  • Biophysics (AREA)
  • Rheumatology (AREA)
  • Plant Pathology (AREA)
  • Mycology (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Neurosurgery (AREA)
AU2006213635A 2005-02-11 2006-02-10 A Capsicum variety exhibiting a hyper-accumulation of zeaxanthin and products derived therefrom Ceased AU2006213635B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US65247805P 2005-02-11 2005-02-11
US60/652,478 2005-02-11
PCT/US2006/004880 WO2006086706A2 (en) 2005-02-11 2006-02-10 A capsicum variety exhibiting a hyper-accumulation of zeaxanthin and products derived therefrom

Publications (2)

Publication Number Publication Date
AU2006213635A1 AU2006213635A1 (en) 2006-08-17
AU2006213635B2 true AU2006213635B2 (en) 2010-06-17

Family

ID=36590163

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2006213635A Ceased AU2006213635B2 (en) 2005-02-11 2006-02-10 A Capsicum variety exhibiting a hyper-accumulation of zeaxanthin and products derived therefrom

Country Status (6)

Country Link
US (3) US20060182826A1 (https=)
EP (2) EP1861078A2 (https=)
JP (1) JP2008532492A (https=)
AU (1) AU2006213635B2 (https=)
CA (1) CA2597402A1 (https=)
WO (2) WO2006086706A2 (https=)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1304768B1 (it) * 1998-10-05 2001-03-29 Esaote Spa Lettino porta paziente o simili, e macchina, in particolare macchinaper il rilevamento d'immagini in risonanza magnetica nucleare in
WO2008121947A1 (en) * 2007-03-30 2008-10-09 University Of Central Florida Research Foundation, Inc. Chloroplasts engineered to express pharmaceutical proteins in edible plants
CH715456B1 (de) 2007-04-27 2020-04-30 Mibelle Ag Kosmetisches Produkt zur topischen Anwendung für den Schutz und die Erneuerung von Hautstammzellen, welches sich von dedifferenzierten Pflanzenzellen ableitet.
US20090189090A1 (en) * 2008-01-25 2009-07-30 Schering-Plough Healthcare Products, Inc. Method of selecting antioxidants for use in topically applied compositions
JP5443470B2 (ja) * 2008-04-29 2014-03-19 株式会社日健総本社 眼障害の治療方法
CN104839476A (zh) * 2008-07-31 2015-08-19 泰国研究基金会 用于猪饲料添加剂生产的辣椒素的用途
JP5608646B2 (ja) * 2008-07-31 2014-10-15 シャクリー コーポレーション 向上した抗酸化活性を有するマスカダイン組成物
US20100034763A1 (en) * 2008-08-05 2010-02-11 Conopco, Inc., D/B/A Unilever Skin Lightening Composition Comprising CO2 Extracts
US8247615B2 (en) * 2010-05-14 2012-08-21 Kalamazoo Holdings, Inc. Process of converting esterified xanthophylls from Capsicum to non-esterified xanthophylls in high yields and purities
US8716533B2 (en) 2009-05-29 2014-05-06 Kalamazoo Holdings, Inc. Methods of saponifying xanthophyll esters and isolating xanthophylls
TWI492744B (zh) * 2009-12-04 2015-07-21 Abbott Lab 使用類胡蘿蔔素調節早產兒發炎症之方法
JP6026719B2 (ja) * 2010-08-31 2016-11-16 株式会社ダイセル 視機能予防・改善剤
CN104797186B (zh) * 2013-03-06 2016-10-12 奥林巴斯株式会社 内窥镜系统
CN104398422A (zh) * 2014-11-14 2015-03-11 成都鹏翔生物科技有限公司 一种含紫苑提取物的滋润控油洁面乳及其制备方法
CN104705061B (zh) * 2015-03-24 2017-03-01 广州华苑园林股份有限公司 一种广西莪术的栽培方法
US10668123B2 (en) 2015-04-27 2020-06-02 Omniactive Health Technologies Limited Capsicum compositions and uses thereof
CN105684750A (zh) * 2016-01-26 2016-06-22 青岛绿色硅谷科技有限公司 一种加快日光温室彩椒着色的方法
WO2017195504A1 (ja) * 2016-05-13 2017-11-16 グリコ栄養食品株式会社 血中カロテノイドバランス改善剤
US10724108B2 (en) * 2016-05-31 2020-07-28 Exxonmobil Upstream Research Company Methods for isolating nucleic acids from samples
US20200069568A1 (en) * 2017-05-15 2020-03-05 Ezaki Glico Co., Ltd. Skin dullness suppressing agent, and skin barrier function maintaining or improving agent
JP7034465B2 (ja) * 2017-09-27 2022-03-14 学校法人東京農業大学 体色が変化したアメリカザリガニの作出方法及び体色が変化したアメリカザリガニ作出用の飼料
US10138173B1 (en) 2017-10-11 2018-11-27 White Flower Associates Zone refining method for nutraceuticals
CN107593135B (zh) * 2017-10-31 2020-07-10 保山市林业和草原技术推广站 一种提高滇橄榄嫁接成活率的方法
CA3118249A1 (en) * 2018-11-05 2020-05-14 Eneos Corporation Composition for increasing retention of carotenoid in blood
CN109364090B (zh) * 2018-12-06 2020-10-23 西华大学 油橄榄叶提取物在制备防治胎儿酒精综合症药物中的应用
CN111004767A (zh) * 2020-01-07 2020-04-14 华侨大学 一种姜黄细胞悬浮培养液及其应用
JP7813719B2 (ja) * 2020-11-12 2026-02-13 江崎グリコ株式会社 形質転換体並びにそれを用いるカロテノイド組成物の製造方法
JP7848040B2 (ja) * 2022-04-14 2026-04-20 公益財団法人東京都農林水産振興財団 烏骨鶏卵の品質改善方法、抗酸化活性が増強された烏骨鶏卵、烏骨鶏用飼料およびその製造方法
CN114807039B (zh) * 2022-06-22 2022-10-04 杭州艾名医学科技有限公司 一种食管癌肿瘤类器官培养用的培养基及培养方法
WO2024084504A2 (en) * 2022-10-21 2024-04-25 Avt Natural Products Ltd. Quercetagetin enriched marigold extracts, compositions, methods of preparation and use thereof
EP4615600A1 (en) * 2022-11-11 2025-09-17 Kemin Industries, Inc. Process for isolation of capsanthin and other carotenoids from paprika oleoresin

Family Cites Families (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3050442A (en) * 1957-05-31 1962-08-21 Philips Corp Method of destroying nematodes with polythienyl compounds
US3539686A (en) 1967-04-10 1970-11-10 Ralph Rosenberg Pigmentation in poultry husbandry
US3989757A (en) * 1973-08-29 1976-11-02 Hoffmann-La Roche Inc. Isomerizing cis-carotenoids to all-trans-carotenoids
US3998753A (en) * 1974-08-13 1976-12-21 Hoffmann-La Roche Inc. Water dispersible carotenoid preparations and processes thereof
US4048203A (en) * 1976-12-06 1977-09-13 Thomas Philip Purification of lutein-fatty acid esters from plant materials
JPS56144078A (en) * 1980-04-08 1981-11-10 Lion Corp Preparation of preservative
DE3119383A1 (de) * 1981-05-15 1982-12-02 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von feinverteilten, pulverfoermigen carotinodpraeparaten
US5107065A (en) * 1986-03-28 1992-04-21 Calgene, Inc. Anti-sense regulation of gene expression in plant cells
DK171297B1 (da) 1987-03-27 1996-08-26 Hoffmann La Roche Fremgangsmåde til fremstilling af cyclohexenderivater som mellemprodukter til fremstilling af zeaxanthin samt cyclohexenderivater
US5227507A (en) * 1987-03-27 1993-07-13 Hoffmann-La Roche Inc. Ethynylcyclohexene compounds and processes for manufacture thereof
US5180747A (en) * 1989-02-28 1993-01-19 Nisshin Flour Milling Co., Ltd. Stabilized fat-soluble vitamin compositions
DE4141351A1 (de) * 1991-12-14 1993-06-17 Basf Ag Stabile pulverfoermige vitamin- und/oder carotinoid-praeparate und verfahren zu deren herstellung
DE4200728A1 (de) * 1992-01-14 1993-07-15 Basf Ag Stabile, fluessige praeparate fettloeslicher substanzen
ATE154822T1 (de) * 1992-04-14 1997-07-15 Hoffmann La Roche Präparate von fettlöslichen substanzen
US5527695A (en) * 1993-01-29 1996-06-18 Purdue Research Foundation Controlled modification of eukaryotic genomes
US6329432B2 (en) * 1993-06-28 2001-12-11 The Howard Foundation Mesozeaxanthin formulations for treatment of retinal disorders
US5506353A (en) * 1994-03-21 1996-04-09 Firmenich Sa Particulate hydrogenated starch hydrolysate based flavoring materials and use of same
US5523494A (en) * 1994-07-20 1996-06-04 Industrial Organica, S.A. De C.V. Process for the isomerization of lutein
ES2170773T3 (es) 1994-10-17 2002-08-16 Firmenich & Cie Compuestos de sabor en forma de particulas y procedimiento para su fabricacion.
AU719671B2 (en) * 1995-06-07 2000-05-18 Howard Foundation, The Pharmaceutically active carotenoids
US5854015A (en) * 1995-10-31 1998-12-29 Applied Food Biotechnology, Inc. Method of making pure 3R-3'R stereoisomer of zeaxanthin for human ingestion
US5827652A (en) * 1995-10-31 1998-10-27 Applied Food Biotechnology, Inc. Zeaxanthin formulations for human ingestion
PL185465B1 (pl) * 1995-10-31 2003-05-30 Applied Food Biotechnology Zastosowanie stereoizomeru 3R-3'R zeaksantyny, kompozycja terapeutyczna do leczenia lub zapobiegania zwyrodnieniu plamki i dodatek do diety
US5648564A (en) * 1995-12-21 1997-07-15 Kemin Industries, Inc. Process for the formation, isolation and purification of comestible xanthophyll crystals from plants
FR2749758B1 (fr) * 1996-06-12 1998-08-07 Oenobiol Sa Lab Composition a activite bronzante et photoprotectrice et ses applications esthetiques
DE19651681A1 (de) * 1996-12-12 1998-06-18 Basf Ag Stabile, wäßrige Dispersionen und stabile, wasserdispergierbare Trockenpulver von Xanthopyllen, deren Herstellung und Verwendung
US5773075A (en) * 1996-12-13 1998-06-30 Kalamazoo Holdings, Inc. High temperature countercurrent solvent extraction of Capsicum solids
MX9606679A (es) 1996-12-19 1997-06-28 Ind Organica Sa De Cv Extracto y formulacion para la pigmentacion de la piel de pollo y de la yema de huevo y metodo para su administracion.
DE19719809C1 (de) * 1997-05-13 1998-05-14 Metallgesellschaft Ag Stabiles trimeres Isopropoxyalan, Verfahren zu seiner Herstellung und seine Verwendung
PE130499A1 (es) * 1997-10-31 1999-12-17 Bioquimex Reka S A De C V Procedimiento para la isomerizacion de luteina a zeaxantina y el producto obtenido con el mismo
US5959138A (en) * 1997-11-25 1999-09-28 Industrial Organica S.A. De C.V. Short chain diesters and process for making the same
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
DE60039079D1 (de) 1999-09-01 2008-07-10 Monsanto Technology Llc Pflanzen-Promotersequenzen aus Mais, die selektiv die Genexpression kontrollieren
CA2346948A1 (en) * 1999-09-06 2001-03-15 Firmenich Sa Process for the preparation of granules for the controlled release of volatile compounds
US6504067B1 (en) * 1999-11-24 2003-01-07 Industrial Organica S.A. De C.V. Process to obtain xanthophyll concentrates of high purity
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
WO2002060865A1 (en) * 2001-01-30 2002-08-08 Sabinsa Corporation Process of obtaining high purity of zeaxanthin, cryptoxanthin & other carotenoids from byadagi chili/chappatta chili & carotenoid composition
US6689400B2 (en) * 2001-01-30 2004-02-10 Sabinsa Corporation Process of obtaining compositions of stable lutein and lutein derivatives
JP2002263403A (ja) * 2001-03-13 2002-09-17 Kanegafuchi Chem Ind Co Ltd 油分を付着含有する無機質材料からの油分の分離方法
US7575766B2 (en) * 2001-06-29 2009-08-18 Ball Horticultural Company Tagetes erecta with altered carotenoid compositions and ratios
US6784351B2 (en) * 2001-06-29 2004-08-31 Ball Horticultural Company Targetes erecta marigolds with altered carotenoid compositions and ratios
US6635293B2 (en) * 2001-10-23 2003-10-21 Kemin Foods, L.C. Finely dispersed carotenoid suspensions for use in foods and a process for their preparation
US20030170326A1 (en) * 2001-12-13 2003-09-11 Council Of Scientific And Industrial Research Bioavailability enchancing activity of Zingiber officinale Linn and its extracts/fractions thereof
US6663900B2 (en) * 2002-02-01 2003-12-16 Kemin Foods, Lc Microcapsules having high carotenoid content

Also Published As

Publication number Publication date
US20060185034A1 (en) 2006-08-17
WO2006086707A3 (en) 2006-09-14
WO2006086706A2 (en) 2006-08-17
CA2597402A1 (en) 2006-08-17
WO2006086706B1 (en) 2007-02-22
WO2006086706A3 (en) 2006-12-21
EP1861078A2 (en) 2007-12-05
WO2006086707A2 (en) 2006-08-17
EP2329815A1 (en) 2011-06-08
JP2008532492A (ja) 2008-08-21
US20120216321A1 (en) 2012-08-23
AU2006213635A1 (en) 2006-08-17
US20060182826A1 (en) 2006-08-17

Similar Documents

Publication Publication Date Title
AU2006213635B2 (en) A Capsicum variety exhibiting a hyper-accumulation of zeaxanthin and products derived therefrom
US10721946B2 (en) Capsicum variety exhibiting a hyper-accumulation of zeaxanthin and products derived therefrom
Kläui et al. Carotenoids as food colors
Zia-Ul-Haq Historical and introductory aspects of carotenoids
US7081478B2 (en) Mixed zeaxanthin ester concentrate and uses thereof
AU2002320200B2 (en) Tagetes erecta marigolds with altered carotenoid compositions and ratios
Shi et al. Lycopene from tomatoes
AU2002320200A1 (en) Tagetes erecta marigolds with altered carotenoid compositions and ratios
JP2021045127A (ja) カロテノイドの大量生産方法
Sajilata et al. Isolation and stabilisation of natural pigments for food applications
US7575766B2 (en) Tagetes erecta with altered carotenoid compositions and ratios
US7595171B2 (en) Ketocarotenoids from Adonis palaestina
MX2007009710A (es) Variedad de capsicum que exhibe una hiperacumulacion de zeaxantina, y productos derivados de la misma.
CN101568644A (zh) 来自巴勒斯坦侧金盏花的酮类胡萝卜素

Legal Events

Date Code Title Description
FGA Letters patent sealed or granted (standard patent)
MK14 Patent ceased section 143(a) (annual fees not paid) or expired