CA2843549A1 - Methods and materials for recombinant production of saffron compounds - Google Patents

Methods and materials for recombinant production of saffron compounds Download PDF

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Publication number
CA2843549A1
CA2843549A1 CA2843549A CA2843549A CA2843549A1 CA 2843549 A1 CA2843549 A1 CA 2843549A1 CA 2843549 A CA2843549 A CA 2843549A CA 2843549 A CA2843549 A CA 2843549A CA 2843549 A1 CA2843549 A1 CA 2843549A1
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CA
Canada
Prior art keywords
crocetin
host
nucleic acid
beta
recombinant
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.)
Abandoned
Application number
CA2843549A
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English (en)
French (fr)
Inventor
Shriram RAGHAVAN
Kalyan K. Kumar
Shailendra SONKAR
Sathish Kumar
Murali PANCHAPAGESA
Esben Halkjaer Hansen
Klavs Riishede Hansen
Jorgen Hansen
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.)
Danstar Ferment AG
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Evolva AG
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Filing date
Publication date
Application filed by Evolva AG filed Critical Evolva AG
Publication of CA2843549A1 publication Critical patent/CA2843549A1/en
Abandoned legal-status Critical Current

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    • 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
    • C12N1/00—Microorganisms; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/14—Fungi; Culture media therefor
    • C12N1/16—Yeasts; Culture media therefor
    • C12N1/18—Baker's yeast; Brewer's yeast
    • C12N1/185—Saccharomyces isolates
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
    • A01H6/00—Angiosperms, i.e. flowering plants, characterised by their botanic taxonomy
    • 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
    • C12N1/00—Microorganisms; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/20—Bacteria; Culture media therefor
    • C12N1/205—Bacterial isolates
    • 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
    • C12N15/80—Vectors or expression systems specially adapted for eukaryotic hosts for fungi
    • 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
    • C12N15/80—Vectors or expression systems specially adapted for eukaryotic hosts for fungi
    • C12N15/81—Vectors or expression systems specially adapted for eukaryotic hosts for fungi for yeasts
    • 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
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/0004—Oxidoreductases (1.)
    • C12N9/0006—Oxidoreductases (1.) acting on CH-OH groups as donors (1.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • 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
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1048—Glycosyltransferases (2.4)
    • 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
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1048—Glycosyltransferases (2.4)
    • C12N9/1051—Hexosyltransferases (2.4.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/88—Lyases (4.)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • C12P19/46—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical bound to a cyclohexyl radical, e.g. kasugamycin
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
    • C12R2001/185—Escherichia
    • C12R2001/19—Escherichia coli
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/645—Fungi ; Processes using fungi
    • C12R2001/85—Saccharomyces
    • C12R2001/865—Saccharomyces cerevisiae

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Mycology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biophysics (AREA)
  • Physics & Mathematics (AREA)
  • Plant Pathology (AREA)
  • Botany (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Virology (AREA)
  • Physiology (AREA)
  • Developmental Biology & Embryology (AREA)
  • Environmental Sciences (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Cell Biology (AREA)
CA2843549A 2011-08-08 2012-08-07 Methods and materials for recombinant production of saffron compounds Abandoned CA2843549A1 (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US201161521171P 2011-08-08 2011-08-08
US61/521,171 2011-08-08
US201161576460P 2011-12-16 2011-12-16
US61/576,460 2011-12-16
US201261595450P 2012-02-06 2012-02-06
US61/595,450 2012-02-06
PCT/IB2012/001513 WO2013021261A2 (en) 2011-08-08 2012-08-07 Methods and materials for recombinant production of saffron compounds

Publications (1)

Publication Number Publication Date
CA2843549A1 true CA2843549A1 (en) 2013-02-14

Family

ID=46970359

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2843549A Abandoned CA2843549A1 (en) 2011-08-08 2012-08-07 Methods and materials for recombinant production of saffron compounds

Country Status (12)

Country Link
US (2) US20140248668A1 (enExample)
EP (1) EP2742131B1 (enExample)
JP (1) JP6126597B2 (enExample)
KR (2) KR101983115B1 (enExample)
CN (1) CN103764818B (enExample)
AU (1) AU2012293402B2 (enExample)
BR (1) BR112014002924A2 (enExample)
CA (1) CA2843549A1 (enExample)
HK (1) HK1199286A1 (enExample)
IN (1) IN2014CN01129A (enExample)
RU (1) RU2676730C2 (enExample)
WO (1) WO2013021261A2 (enExample)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105671108A (zh) 2010-06-02 2016-06-15 沃维公司 甜菊糖苷的重组生产
CA2899276C (en) 2013-02-06 2022-11-01 Evolva Sa Methods for improved production of rebaudioside d and rebaudioside m
US10017804B2 (en) 2013-02-11 2018-07-10 Evolva Sa Efficient production of steviol glycosides in recombinant hosts
WO2015132411A2 (en) * 2014-03-07 2015-09-11 Evolva Sa Methods for recombinant production of saffron compounds
EP3134539A1 (en) * 2014-04-25 2017-03-01 Evolva SA Methods for recombinant production of saffron compounds
CA3109156C (en) * 2014-05-16 2023-08-15 Academia Sinica Recombinant polynucleotide sequence for producing astaxanthin and uses thereof
US9969989B2 (en) 2014-07-23 2018-05-15 Agenzia Nazionale Per Le Nuove Tecnologie, L'ener- Gia E Lo Sviluppo Economico Sostenibile (Enea) Carotenoid dioxygenase and methods for the biotechnological production in microorganisms and plants of compounds derived from saffron
MX2017001859A (es) 2014-08-11 2017-04-11 Evolva Sa Produccion de glicosidos de esteviol en hospederos recombinantes.
JP2017528134A (ja) * 2014-09-09 2017-09-28 エヴォルヴァ エスアー.Evolva Sa. 組み換え宿主におけるステビオールグリコシドの生産
BR112017016338A2 (en) 2015-01-30 2018-03-27 Evolva Sa production of steviol glycosides in recombinant hosts
CA3255837A1 (en) 2015-03-16 2025-10-30 Dsm Ip Assets B.V. Udp-glycosyltransferases
JP2018522569A (ja) 2015-08-07 2018-08-16 エヴォルヴァ エスアー.Evolva Sa. 組換え宿主内でのステビオールグリコシドの産生
AU2017205501A1 (en) 2016-01-07 2018-07-05 Conagen Inc. Methods of making capsinoids by biosynthetic processes
MY198001A (en) 2016-04-13 2023-07-25 Evolva SA Production of steviol glycoside in recombinant hosts
WO2017198682A1 (en) 2016-05-16 2017-11-23 Evolva Sa Production of steviol glycosides in recombinant hosts
CN105779406B (zh) * 2016-05-25 2019-06-18 新疆农业科学院经济作物研究所 一种藏红花酸糖基转移酶及其编码基因与应用
CN105950493B (zh) * 2016-05-25 2019-12-27 天津大学 一种工程菌及其构建方法与在制备藏红花酸中的应用
CN105950580B (zh) * 2016-05-25 2019-03-08 新疆农业科学院经济作物研究所 一种制备蛋白质UGTCs4的方法
BR112019000895A2 (pt) 2016-07-19 2019-04-30 Conagen Inc. método para a produção microbiana de capsaicinoides naturais específicos
US11396669B2 (en) 2016-11-07 2022-07-26 Evolva Sa Production of steviol glycosides in recombinant hosts
CN108728477B (zh) * 2017-04-24 2022-02-22 华东理工大学 一种高效的转座突变系统及构建方法
IT201700089843A1 (it) * 2017-08-03 2019-02-03 Enea Agenzia Naz Per Le Nuove Tecnologie Lenergia E Lo Sviluppo Economico Sostenibile Geni e metodi per la produzione e compartimentazione biotecnologica di apocarotenoidi ad elevato valore aggiunto
CN110791510A (zh) * 2018-08-02 2020-02-14 中国医学科学院药用植物研究所 一种参与西红花酸合成的乙醛脱氢酶编码基因的筛选鉴定及应用
WO2020093285A1 (zh) * 2018-11-07 2020-05-14 中国医学科学院药用植物研究所 用于生物合成西红花苷的酶基因及其应用
CA3118924A1 (en) 2018-11-09 2020-05-14 Ginkgo Bioworks, Inc. Biosynthesis of mogrosides
CN109943493B (zh) * 2019-04-17 2021-05-18 天津大学 实现通用酶催化功能多样性的突变体菌株及其构建方法
KR102335035B1 (ko) * 2019-09-17 2021-12-06 아주대학교 산학협력단 효소반응을 이용한 크로신-4의 생산방법
EP4151732A1 (en) * 2021-09-15 2023-03-22 Universidad de Castilla-La Mancha Transgenic plants producing high levels of apocarotenoids compounds and uses thereof
CN117467633A (zh) * 2022-07-28 2024-01-30 上海中医药大学 Ugt71a3作为催化剂在制备三萜皂苷中的应用
CN116083288B (zh) * 2022-11-11 2025-02-18 泸州品创科技有限公司 产2,3-二氢-2,2,6-三甲基苯甲醛的肠膜明串珠菌及其应用
KR20250075325A (ko) * 2023-11-21 2025-05-28 아주대학교산학협력단 크로신 및 전구체 생산용 재조합 효모
CN118546994B (zh) * 2024-06-18 2025-01-28 华南农业大学 一种在种子胚乳生产藏红花素的转基因育种方法

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6946587B1 (en) 1990-01-22 2005-09-20 Dekalb Genetics Corporation Method for preparing fertile transgenic corn plants
US5484956A (en) 1990-01-22 1996-01-16 Dekalb Genetics Corporation Fertile transgenic Zea mays plant comprising heterologous DNA encoding Bacillus thuringiensis endotoxin
US5204253A (en) 1990-05-29 1993-04-20 E. I. Du Pont De Nemours And Company Method and apparatus for introducing biological substances into living cells
US5306862A (en) 1990-10-12 1994-04-26 Amoco Corporation Method and composition for increasing sterol accumulation in higher plants
US5460949A (en) 1990-11-15 1995-10-24 Amoco Corporation Method and composition for increasing the accumulation of squalene and specific sterols in yeast
DK0747483T3 (da) * 1995-06-09 2004-06-28 Dsm Ip Assets Bv Fermentativ carotenoid-produktion
JPH10117776A (ja) 1996-10-22 1998-05-12 Japan Tobacco Inc インディカイネの形質転換方法
ATE242812T1 (de) * 1996-12-02 2003-06-15 Hoffmann La Roche Verbesserte fermentative herstellung von carotenoide
DE19916140A1 (de) * 1999-04-09 2000-10-12 Basf Ag Carotinhydroxylase und Verfahren zur Herstellung von Xanthophyllderivaten
PT1190068E (pt) 1999-04-15 2006-06-30 Calgene Llc Sequencias de acidos nucleicos para proteinas envolvidas na sintese de tocoferol
US20040078846A1 (en) 2002-01-25 2004-04-22 Desouza Mervyn L. Carotenoid biosynthesis
US20050003474A1 (en) 2001-01-26 2005-01-06 Desouza Mervyn L. Carotenoid biosynthesis
EP1532265A2 (de) * 2002-08-20 2005-05-25 Sungene GmbH & Co. KGaA Verfahren zur herstellung von ketocarotinoiden in genetisch veränderten organismen
JP2006500055A (ja) * 2002-09-27 2006-01-05 ディーエスエム アイピー アセッツ ビー.ブイ. ファフィア属によるゼアキサンチンの製造方法
EP1765418B1 (en) 2004-05-21 2011-12-14 The Regents of the University of California Method for enhancing production of isoprenoid compounds
CN101321859A (zh) * 2005-12-06 2008-12-10 东曹株式会社 新微生物和使用该微生物生产类胡萝卜素的方法
US8846374B2 (en) * 2006-12-12 2014-09-30 E I Du Pont De Nemours And Company Carotenoid production in a recombinant oleaginous yeast

Also Published As

Publication number Publication date
KR101983115B1 (ko) 2019-05-29
KR101815063B1 (ko) 2018-01-05
KR20140057319A (ko) 2014-05-12
CN103764818B (zh) 2017-05-31
AU2012293402B2 (en) 2017-08-03
US20140248668A1 (en) 2014-09-04
JP6126597B2 (ja) 2017-05-10
HK1199286A1 (en) 2015-06-26
EP2742131A2 (en) 2014-06-18
WO2013021261A2 (en) 2013-02-14
RU2014109010A (ru) 2015-09-20
IN2014CN01129A (enExample) 2015-04-10
WO2013021261A3 (en) 2013-05-02
EP2742131B1 (en) 2018-11-28
JP2014524246A (ja) 2014-09-22
CN103764818A (zh) 2014-04-30
US20170306376A1 (en) 2017-10-26
AU2012293402A1 (en) 2014-02-06
RU2676730C2 (ru) 2019-01-10
AU2012293402A2 (en) 2014-03-13
KR20180004306A (ko) 2018-01-10
BR112014002924A2 (pt) 2018-10-09

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