DOCSLIB.ORG

Protic Ionic Liquids As Cell Disrupting Agents for the Recovery Of

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Protic Ionic Liquids As Cell Disrupting Agents for the Recovery Of Subscriber access provided by UNIV EST PAULISTA UNESP Article Protic ionic liquids as cell disrupting agents for the recovery of intracellular carotenoids from yeast Rhodotorula glutinis CCT-2186 Cassamo U Mussagy, Valéria de Carvalho Santos Ebinuma, Maria Gonzalez-Miquel, Joao A.P. Coutinho, and Jorge Fernando Brandão Pereira ACS Sustainable Chem. Eng., Just Accepted Manuscript • DOI: 10.1021/ acssuschemeng.9b04247 • Publication Date (Web): 03 Sep 2019 Downloaded from pubs.acs.org on September 9, 2019 Just Accepted “Just Accepted” manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides “Just Accepted” as a service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. “Just Accepted” manuscripts appear in full in PDF format accompanied by an HTML abstract. “Just Accepted” manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are citable by the Digital Object Identifier (DOI®). “Just Accepted” is an optional service offered to authors. Therefore, the “Just Accepted” Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the “Just Accepted” Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these “Just Accepted” manuscripts. is published by the American Chemical Society. 1155 Sixteenth Street N.W., Washington, DC 20036 Published by American Chemical Society. Copyright © American Chemical Society. However, no copyright claim is made to original U.S. Government works, or works produced by employees of any Commonwealth realm Crown government in the course of their duties. Page 1 of 38 ACS Sustainable Chemistry & Engineering 1 2 3 4 5 6 7 Protic ionic liquids as cell disrupting agents for the recovery of intracellular 8 9 carotenoids from yeast Rhodotorula glutinis CCT-2186 10 11 12 † † ‡ 13 Cassamo U. Mussagy, Valéria C. Santos-Ebinuma, Maria Gonzalez-Miquel, 14 João A. P. Coutinho,§ and Jorge F. B. Pereira*† 15 16 17 18 †Department of Bioprocesses and Biotechnology, School of Pharmaceutical Sciences, Sao 19 20 Paulo State University (UNESP), Rodovia Araraquara Jaú, Km 01, Campos Ville – 14800- 21 22 903 - Araraquara/SP - Brazil 23 24 ‡Departamento de Ingeniería Química Industrial y del Medio Ambiente, ETS Ingenieros 25 26 Industriales, Universidad Politécnica de Madrid, C/José Gutiérrez Abascal 2, Madrid 27 28006, Spain 28 29 § 30 CICECO−Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 31 3810-193 Aveiro, Portugal 32 33 *Corresponding author: [email protected] 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 ACS Paragon Plus Environment ACS Sustainable Chemistry & Engineering Page 2 of 38 1 2 3 4 5 6 ABSTRACT 7 8 Rhodotorula glutinis 9 yeasts are natural sources of intracellular carotenoids such as 10 β-carotene, torularhodin and torulene. Since these yeasts are constituted by a rigid 11 12 cell-wall structure, the use of energy-saving and high-efficiency cell disruption 13 14 procedures is critical for carotenoids recovery. A new technology using protic ionic 15 liquids (PILs) was here evaluated as alternative platform to permeabilize the R. 16 17 glutinis cells and to improve the extraction of β-carotene, torularhodin and torulene. 18 19 The cell disruption ability of twelve highly concentrated aqueous solutions of 20 ammonium-based PILs was determined, evaluating the influence of the relative ions 21 22 hydrophobicity, solid-liquid ratio (SLR), water content, and temperature. Carotenoid 23 24 extraction yields increased with the hydrophobicity of the PILs (i.e. increase of alkyl 25 chain length of anion or cation), temperature (from 25 ºC to 65 ºC) and PIL 26 27 concentration (from 75% to 90% v/v). Additionally, to demonstrate the potential of 28 29 PILs in carotenoids recovery, solvent recycling and carotenoids polishing were 30 carried out using a three-phase partitioning (TPP) system. The results demonstrate 31 32 that the use of PILs as cell disrupting agents can be a simple, efficient, sustainable 33 34 and feasible method to recover intracellular carotenoids from microbial biomass. 35 36 37 38 Keywords: Rhodotorula glutinis; carotenoids; extraction, protic ionic liquids; β- 39 40 carotene; torularhodin; torulene. 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 ACS Paragon Plus Environment Page 3 of 38 ACS Sustainable Chemistry & Engineering 1 2 3 4 5 6 INTRODUCTION 7 8 Carotenoids are a group of yellow, orange and red polyisoprenoid pigments, 9 10 that can be naturally synthesized by different microorganisms, including microalgae, 11 12 bacteria, yeasts and filamentous fungi 1,2. These biopigments exhibit a plethora of 13 biological attractive properties, such as antioxidant, antiobesity, antidiabetic, 14 15 anticancer (particularly those that results from cardiovascular diseases and macular 16 17 degeneration) and antimicrobial activities 3–5. As a result of their interesting biological 18 19 properties, natural carotenoids have been attracting great interest from academic 20 and industrial partners for applications in pharmaceuticals, cosmetics and functional 21 22 foods formulations, as well as the most common uses in food industries 6–8. 23 9 24 Rhodotorula glutinis are aerobic yeasts able to synthesize, in an easy and 25 natural way, several industrial high-added value metabolites, e.g. lipids, carotenoids, 26 27 and enzymes. Particularly, these yeasts can produce and accumulate approximately 28 10,11 29 50% of their dried cellular biomass as fractions of carotenoids and lipids . Among 30 the carotenoids, Rhodotorula glutinis are able to synthesize β-carotene, torulene, 31 32 and torularhodin, exhibiting variable production yields according to the specific 33 11 12 34 cultivation conditions and fast grow . 35 However, since the carotenoids from R. glutinis yeast are produced 36 37 intracellularly, appropriate cell-disrupting methodologies are always required for their 38 13 39 recovery . A large number of cell disruption techniques, including conventional and 40 non-conventional procedures, have been reported in literature 2,14. Traditionally, 41 42 Rhodotorula glutinis yeasts are disrupted by using conventional solid-liquid 43 44 extraction procedures with volatile organic solvents (VOCs), such as petroleum 45 ether, dimethyl sulfoxide (DMSO), acetone, chloroform and hexane 15. Among the 46 47 common VOCs, the use of DMSO, in general, lead to the highest release rates of 48 49 intracellular carotenoids, but their use in industrial processes is limited by health and 50 environmental concerns 16,17. 51 52 Therefore, the search for more biocompatible and environmentally friendly 53 54 solvents, as for example, biosolvents, ionic liquids (ILs) and deep eutectic solvents, 55 is of great importance. Among these, ILs, commonly defined as salts with a melting 56 57 point lower than 100 °C 18, have been suggested as one of the most interesting 58 59 60 ACS Paragon Plus Environment ACS Sustainable Chemistry & Engineering Page 4 of 38 1 2 3 4 5 6 classes of alternative solvents, mainly due to their unique features like high hydrolytic 7 8 activity, low volatility, high solvation capacity, and excellent thermal and chemical 9 stabilities 19. 10 11 Some studies evaluated the capability of different ILs for the extraction of 12 19–21 19 13 carotenoids . Choi and collaborators extracted astaxanthin and lipids from 14 Haematococcus pluvialis cyst cells using ten 1-ethyl-3-methylimidazolium ([Emim]+)- 15 16 based ILs, obtaining complete astaxanthin recoveries (> 99%) and high lipid 17 18 extraction yields (∼82%) at optimum operating conditions, i.e. 6.7% (v/v) of IL in 19 water, 30 °C of temperature and 60 min of extraction time. Desai and collaborators 20 21 20 recovered more than 70% of intracellular astaxanthin from intact H. pluvialis cells 22 23 using an aqueous solution of 1-ethyl-3-methylimidazolium di-butyl-phosphate 24 21 25 ([Emim][DBP]) (40 wt%). Vieira and collaborators recovered fucoxanthin from 26 Sargassum muticum cells using aqueous solutions of different surface-active ILs. 27 28 These examples demonstrate that ILs are effective solvents to extract carotenoids 29 30 from natural sources; however, most of these works have been performed using 31 “classic” aprotic ILs (AILs). Recent studies have indicated that AILs are not the most 32 33 adequate for biological-based applications due to their cytotoxicity 22, which led to a 34 35 growing interest in the third-generation of more benign and biocompatible ILs, i.e. 36 protic ionic liquids (PILs) 23. 37 38 PILs are a subset of ILs prepared through the stoichiometric neutralization 39 40 reaction of certain Brønsted acids and Brønsted bases. They have a proton available 41 for hydrogen bonding, and differ from the classic AILs in having both cationic and 42 43 anionic counterparts formed by low molecular weight organic compounds, usually 44 23 45 substituted (or poly-substituted) amines as cations, and organic acids as anions . 46 PILs are more favourable than AILs in terms of toxicity and biodegradability 47 48 24. This fact, coupled with its low production cost, easier synthesis and more benign 49 50 nature (i.e. can be obtained fully or partly from natural raw materials) make them 51 attractive solvents for wider use in industrial bioprocesses 25. 52 53 Considering these assumptions, the aim of this study was to evaluate the 54 55 capability of PILs to disrupt (permeabilize) the cell wall of Rhodotorula glutinis yeasts 56 and to increase the recoveries of intracellular carotenoids.
Load more

Recommended publications
  • Effect of Phenol on Β-Carotene Content in Total Carotenoids Production in Cultivation of Rhodotorula Glutinis
    Korean J. Chem. Eng., 21(3), 689-692 (2004) Effect of Phenol on β-Carotene Content in Total Carotenoids Production in Cultivation of Rhodotorula glutinis Bong Kyun Kim*, Pyoung Kyu Park, Hee Jeong Chae** and Eui Yong Kim† Department of Chemical Engineering, University of Seoul, Seoul 130-743, Korea *R&D Center, SEMO Co. Ltd., Incheon 558-10, Korea **Department of Food and Biotechnology, and Department of Innovative Industrial Technology, Graduate School of Venture, Hoseo University, Asan 336-795, Korea (Received 28 November 2003 • accepted 18 December 2003) Abstract−The composition of carotenoids produced by R. glutinis was observed to be dependent upon the addition of phenol into medium. A stimulatory effect of phenol on β-carotene of Rhodotorula glutins K-501 grown on glucose was investigated. Carotenoids produced by Rhodotorula glutinis K-501 were identified to torularhodin, torulene and β-carotene, whose composition was 79.5%, 6.4% and 14.1%, respectively. The β-carotene content increased up to 35% when phenol was added to culture media at 500 ppm. The ratio of torularhodin decreased with increasing phenol con- centration, while torulene content was almost constant. Key words: Phenol, β-Carotene, Carotenogenic Ratio, Rhodotorula glutinis INTRODUCTION Sporobolomyces, produce a variety of carotenoids that have a broad region of light absorption of 450-550 nm so that the culture broth Carotenoids are liposoluble tetraterpenes, usually red or yellow, has a colored appearance [Girad et al., 1994; Walker et al., 1973]. and are one of the most important families of natural pigments. These The fermentation conditions, such as cultivation temperature [Nelis pigments have several conjugated double bonds that act as chro- and Deleenheer, 1991], lightening [Meyer et al., 1994], induced sub- mophores and thus absorb light in the visible region, which gives stances [Schroeder et al., 1993, 1995], and inhibitors [Girad et al., them their strong coloration properties.
    [Show full text]
  • Multiplicity of Carotene Patterns Derives from Competition Between
    www.nature.com/scientificreports OPEN Multiplicity of carotene patterns derives from competition between phytoene desaturase diversifcation and biological environments Mathieu Fournié1,2,3 & Gilles Truan1* Phytoene desaturases catalyse from two to six desaturation reactions on phytoene, generating a large diversity of molecules that can then be cyclised and produce, depending on the organism, many diferent carotenoids. We constructed a phylogenetic tree of a subset of phytoene desaturases from the CrtI family for which functional data was available. We expressed in a bacterial system eight codon optimized CrtI enzymes from diferent clades. Analysis of the phytoene desaturation reactions on crude extracts showed that three CrtI enzymes can catalyse up to six desaturations, forming tetradehydrolycopene. Kinetic data generated using a subset of fve purifed enzymes demonstrate the existence of characteristic patterns of desaturated molecules associated with various CrtI clades. The kinetic data was also analysed using a classical Michaelis–Menten kinetic model, showing that variations in the reaction rates and binding constants could explain the various carotene patterns observed. Competition between lycopene cyclase and the phytoene desaturases modifed the distribution between carotene intermediates when expressed in yeast in the context of the full β-carotene production pathway. Our results demonstrate that the desaturation patterns of carotene molecules in various biological environments cannot be fully inferred from phytoene desaturases classifcation but is governed both by evolutionary-linked variations in the desaturation rates and competition between desaturation and cyclisation steps. Carotenoids are organic pigments produced by plants, algae, fungi, and bacteria and can be subdivided into two families of molecules, carotenes and their oxidised counterparts, xanthophylls 1.
    [Show full text]
  • Vitamin Synthesis in Plants: Tocopherols and Carotenoids
    ANRV274-PP57-27 ARI 29 March 2006 12:21 Vitamin Synthesis in Plants: Tocopherols and Carotenoids Dean DellaPenna1 and Barry J. Pogson2 1Department of Biochemistry and Molecular Biology, Michigan State University, East Lansing, Michigan 48824; email: [email protected] 2ARC Center of Excellence in Plant Energy Biology, School of Biochemistry and Molecular Biology, Australian National University, Canberra ACT 0200, Australia; email: [email protected] Annu. Rev. Plant Biol. Key Words 2006. 57:711–38 metabolic engineering, vitamin E, provitamin A, Arabidopsis, The Annual Review of Plant Biology is online at chloroplast, photosynthesis plant.annualreviews.org Abstract by UNIVERSITAT BERN on 09/12/09. For personal use only. doi: 10.1146/ annurev.arplant.56.032604.144301 Carotenoids and tocopherols are the two most abundant groups of Copyright c 2006 by lipid-soluble antioxidants in chloroplasts. In addition to their many Annual Reviews. All rights functional roles in photosynthetic organisms, these compounds are Annu. Rev. Plant Biol. 2006.57:711-738. Downloaded from arjournals.annualreviews.org reserved also essential components of animal diets, including humans. During First published online as a the past decade, a near complete set of genes required for the synthe- Review in Advance on February 7, 2006 sis of both classes of compounds in photosynthetic tissues has been identified, primarily as a result of molecular genetic and biochemi- 1543-5008/06/0602- 0711$20.00 cal genomics-based approaches in the model organisms Arabidopsis thaliana and Synechocystis sp. PCC6803. Mutant analysis and trans- genic studies in these and other systems have provided important insight into the regulation, activities, integration, and evolution of individual enzymes and are already providing a knowledge base for breeding and transgenic approaches to modify the types and levels of these important compounds in agricultural crops.
    [Show full text]
  • Β-Carotene-Rich Carotenoid-Protein Preparation and Exopolysaccharide Production by Rhodotorula Rubra GED8 Grown with a Yogurt S
    -Carotene-Rich Carotenoid-Protein Preparation and Exopolysaccharide Production by Rhodotorula rubra GED8 Grown with a Yogurt Starter Culture Ginka I. Frengova*, Emilina D. Simova, and Dora M. Beshkova Laboratory of Applied Microbiology, Institute of Microbiology, Bulgarian Academy of Sciences, 4002 Plovdiv, 26 Maritza Blvd., Bulgaria. E-mail: [email protected] * Author for correspondence and reprint requests Z. Naturforsch. 61c, 571Ð577 (2006); received December 29, 2005/February 6, 2006 The underlying method for obtaining a -carotene-rich carotenoid-protein preparation and exopolysaccharides is the associated cultivation of the carotenoid-synthesizing lactose-nega- tive yeast strain Rhodotorula rubra GED8 with the yogurt starter culture (Lactobacillus bulgaricus 2-11 + Streptococcus thermophilus 15HA) in whey ultrafiltrate (45 g lactose/l) with a maximum carotenoid yield of 13.37 mg/l culture fluid on the 4.5th day. The chemical composition of the carotenoid-protein preparation has been identified. The respective caro- tenoid and protein content is 497.4 μg/g dry cells and 50.3% per dry weight, respectively. An important characteristic of the carotenoid composition is the high percentage (51.1%) of - carotene (a carotenoid pigment with the highest provitamin A activity) as compared to 12.9% and 33.7%, respectively, for the other two individual pigments Ð torulene and torularhodin. Exopolysaccharides (12.8 g/l) synthesized by the yeast and lactic acid cultures, identified as acid biopolymers containing 7.2% glucuronic acid, were isolated in the cell-free supernatant. Mannose, produced exclusively by the yeast, predominated in the neutral carbohydrate bio- polymer component (76%). The mixed cultivation of R. rubra GED8 with the yogurt starter (L.
    [Show full text]
  • Directed Evolution of Biosynthetic Pathways to Carotenoids With
    1 CHAPTER 1 Diversifying Carotenoid Biosynthetic Pathways in the Laboratory Material from this chapter appears in Diversifying Carotenoid Biosynthetic Pathways by Directed Evolution, Daisuke Umeno‡, Alexander V. Tobias‡, and Frances H. Arnold, Microbiology and Molecular Biology Reviews, 69(1): 51-78 (2005) and is reprinted with permission from the American Society for Microbiology. ‡ Co-first authors 2 SUMMARY Microorganisms and plants synthesize a diverse array of natural products, many of which have proven indispensable to human health and well-being. Although many thousands of these have been characterized, the space of possible natural products—those that could be made biosynthetically—remains largely unexplored. For decades, this space has largely been the domain of chemists, who have synthesized scores of natural product analogs and have found many with improved or novel functions. New natural products have also been made in recombinant organisms via engineered biosynthetic pathways. Recently, methods inspired by natural evolution have begun to be applied to the search for new natural products. These methods force pathways to evolve in convenient laboratory organisms, where the products of new pathways can be identified and characterized in high- throughput screening programs. Carotenoid biosynthetic pathways have served as a convenient experimental system with which to demonstrate these ideas. Researchers have mixed, matched, and mutated carotenoid biosynthetic enzymes and screened libraries of these “evolved” pathways for the emergence of new carotenoid products. This has led to dozens of new pathway products not previously known to be made by the assembled enzymes. These new products include whole families of carotenoids built from backbones not found in nature.
    [Show full text]
  • The Role of Carotenoids and Their Derivatives in Mediating Interactions Between Insects and Their Environment
    Arthropod-Plant Interactions (2013) 7:1–20 DOI 10.1007/s11829-012-9239-7 REVIEW ARTICLE The role of carotenoids and their derivatives in mediating interactions between insects and their environment Jeremy J. Heath • Don F. Cipollini • John O. Stireman III Received: 16 March 2012 / Accepted: 28 November 2012 / Published online: 28 December 2012 Ó Springer Science+Business Media Dordrecht 2012 Abstract Carotenoids are long conjugated isoprenoid environment depends on them (Britton 1995a). Carotenoids molecules derived mainly from plants and microbial organ- are one of the most ubiquitous groups of organic molecules isms. They are highly diverse, with over 700 identified known, but how they function in modulating insect–envi- structures, and are widespread in nature. In addition to their ronment interactions is only beginning to be understood. In fundamental roles as light-harvesting molecules in photo- general, they are long conjugated chains of carbon with synthesis, carotenoids serve a variety of functions including rings on either end, which may contain oxygenated func- visual and colouring pigments, antioxidants and hormone tional groups. Carotenoids are essential in photosynthesis to precursors. Although the functions of carotenoids are rela- harvest light energy and protect chlorophyll in times of tively well studied in plants and vertebrates, studies are excess light energy by quenching reactive oxygen species severely lacking in insect systems. There is a particular dearth that are produced during photosynthesis and plant stress. In of knowledge on how carotenoids move among trophic levels, animals, their bright yellow to red colour is employed as influence insect multitrophic interactions and affect evolu- mating signals and aposematic colouration.
    [Show full text]
  • View and Research Objectives
    University of Alberta Carotenoid diversity in novel Hymenobacter strains isolated from Victoria Upper Glacier, Antarctica, and implications for the evolution of microbial carotenoid biosynthesis by Jonathan Lee Klassen A thesis submitted to the Faculty of Graduate Studies and Research in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Microbiology and Cell Biotechnology Department of Biological Sciences ©Jonathan Lee Klassen Fall 2009 Edmonton, Alberta Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission. Examining Committee Dr. Julia Foght, Department of Biological Science Dr. Phillip Fedorak, Department of Biological Sciences Dr. Brenda Leskiw, Department of Biological Sciences Dr. David Bressler, Department of Agriculture, Food and Nutritional Science Dr. Jeffrey Lawrence, Department of Biological Sciences, University of Pittsburgh Abstract Many diverse microbes have been detected in or isolated from glaciers, including novel taxa exhibiting previously unrecognized physiological properties with significant biotechnological potential. Of 29 unique phylotypes isolated from Victoria Upper Glacier, Antarctica (VUG), 12 were related to the poorly studied bacterial genus Hymenobacter including several only distantly related to previously described taxa.
    [Show full text]
  • 3. Food Chemistry & Biotechnology 3.1. Lectures
    Chem. Listy, 102, s265–s1311 (2008) Food Chemistry & Biotechnology 3. FOOD CHEMISTRY been femented for 10 days at 10 °c under semiaerobic condi- & BIOTECHNOLOGY tions or 4–6 weeks at 10 °c under anaerobic conditions. Second cultivation medium: the sterile vinea drinks were inoculated by studied yeast strains and cultuivated at 3.1. Lectures 20 °c for 10 days under semiaerobic conditions. the samples were than sensorially evaluated by a group L01 NONSACCHAROMYCES YEAST IN GRAPE of degustators. the same samples were than analysed by gas MUST – ADVANTAGE OR SPOILAGE? chromatography for the aroma compounds production. each sample was analysed on the Gc MS (Shimadzu QP 2010) JAROSLAVA Kaňuchová PátKováa, EMÍLIA equipment and also on the Gc FiD equipment (Gc 8000 ce Breierováb and INGRID vajcziKová instruments). aInstitute for viticulture and enology of SARC two methods of sample preparation were done: Matuškova 25, 831 01 Bratislava, Slovak republic, the samples (20 ml) were extracted by ether (2 ml), and bInstitute of ChemistrySAS, Dúbravská cesta 9, 845 38 Brati- centrifuged prior to analysis. the etheric extract was used for slava, Slovak republic, analysis (liquid – liquid extraction). this method was used [email protected] for higher alcohols (propanol, isoamylacohol, ethyl ester and higher alcoholos esters) determination Introduction the samples were extracted by tenaq (solid phase mic- the fresh grape must consists of spontaneous microf- roextraction) and than 10 min sampling according to6. this lora formed from 90 to 99 % by yeasts. the most important method was used for monoterpenic compounds determina- genus is without doubt Saccharomyces cerevisiae which is tion.the same column and the same conditions were used by responsible for successive fermentation and good wine qua- both analysis: column: DB WaX 30 m, 0.25 × 0.25, tempe- lity.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 7,252,985 B2 Cheng Et Al
    US007252985B2 (12) United States Patent (10) Patent No.: US 7,252,985 B2 Cheng et al. (45) Date of Patent: Aug. 7, 2007 (54) CAROTENOID KETOLASES Echinenone in the Cyanobacterium Synechocystis sp. PCC 6803*, J. Biol. Chem., vol. 272(15):9728-9733, 1997. (75) Inventors: Qiong Cheng, Wilmington, DE (US); Norihiko Misawa et al., Metabolic engineering for the production of Luan Tao, Claymont, DE (US); Henry carotenoids in non-carotenogenic bacteria and yeasts, J. of Biotech., Yao, Boothwyn, PA (US) vol. 59:169-181, 1998. National Center for Biotechnology Information General Identifier (73) Assignee: E. I. du Pont de Nemours and No. 5912291, Accession No. Y 15112, Sep. 15, 1999, M. Harker et Company, Wilmington, DE (US) al., Carotenoid biosynthesis genes in the bacterium Paracoccus narcusii MH1. National Center for Biotechnology Information General Identifier (*) Notice: Subject to any disclaimer, the term of this No. 2654317. Accession No. X86782, Sep. 9, 2004, M. Harker et patent is extended or adjusted under 35 al., Biosynthesis of ketocarotenoids in transgenic cyanobacteria U.S.C. 154(b) by 326 days. expressing the algal gene for beta-C-4-oxygenase, crtO. National Center for Biotechnology Information General Identifier (21) Appl. No.: 11/015,433 No. 903298, Accession No. D58422, N. Misawa et al., Canthaxanthin biosynthesis by the conversion of methylene to keto (22) Filed: Dec. 17, 2004 groups in a hydrocarbon beta-carotene by a single gene Biochem. Biophys. Res. Commun. 209(3), 867-876 (1995). (65) Prior Publication Data National Center for Biotechnology Information General Identifier No. 61629280, Accession No. D58420, N. Misawa et al., US 2005/0227311 A1 Oct.
    [Show full text]
  • Carotenoids Database: Structures, Chemical Fingerprints and Distribution Among Organisms Junko Yabuzaki*
    Database, 2017, 1–11 doi: 10.1093/database/bax004 Original article Original article Carotenoids Database: structures, chemical fingerprints and distribution among organisms Junko Yabuzaki* Center for Information Biology, National Institute of Genetics, Yata 1111, Mishima, Shizuoka 411-8540, Japan *Corresponding author: Tel: þ81 774 23 2680; Fax: þ81 774 23 2680; Email: [email protected][AQ] Present address: Junko Yabuzaki, 1 34-9, Takekura, Mishima, Shizuoka 411-0807, Japan. Citation details: Yabuzaki,J. Carotenoids Database: structures, chemical fingerprints and distribution among organisms (2017) Vol. 2017: article ID bax004; doi:10.1093/database/bax004 Received 13 April 2016; Revised 14 January 2017; Accepted 16 January 2017 Abstract To promote understanding of how organisms are related via carotenoids, either evolu- tionarily or symbiotically, or in food chains through natural histories, we built the Carotenoids Database. This provides chemical information on 1117 natural carotenoids with 683 source organisms. For extracting organisms closely related through the biosyn- thesis of carotenoids, we offer a new similarity search system ‘Search similar caroten- oids’ using our original chemical fingerprint ‘Carotenoid DB Chemical Fingerprints’. These Carotenoid DB Chemical Fingerprints describe the chemical substructure and the modification details based upon International Union of Pure and Applied Chemistry (IUPAC) semi-systematic names of the carotenoids. The fingerprints also allow (i) easier prediction of six biological functions of carotenoids: provitamin A, membrane stabilizers, odorous substances, allelochemicals, antiproliferative activity and reverse MDR activity against cancer cells, (ii) easier classification of carotenoid structures, (iii) partial and exact structure searching and (iv) easier extraction of structural isomers and stereoisomers. We believe this to be the first attempt to establish fingerprints using the IUPAC semi- systematic names.
    [Show full text]
  • Carotenoids of Hemipteran Insects, from the Perspective of Chemo
    Biochemical Systematics and Ecology 95 (2021) 104241 Contents lists available at ScienceDirect Biochemical Systematics and Ecology journal homepage: www.elsevier.com/locate/biochemsyseco Carotenoids of hemipteran insects, from the perspective of ☆ chemo-systematic and chemical ecological studies Takashi Maoka a,*, Naoki Kawase b, Mantaro Hironaka c, Ritsuo Nishida d a Research Institute for Production Development 15 Shimogamo-morimoto-cho, Sakyo-ku, Kyoto, 606-0805, Japan b Minakuchi Kodomonomori Nature Museum 10 Kita-naiki, Minakuchi-cho, Koka, 528-0051, Japan c Ishikawa Prefecture University, Bioresources and Environmental Sciences 305, Suematsu, Nonoichi-1, 921-8836, Japan d Kyoto University Yoshida-Honmachi, Sakyo-ku, Kyoto, 606-8501, Japan ARTICLE INFO ABSTRACT Keywords: Carotenoids of 47 species of insects belonging to Hemiptera, including 16 species of Sternorrhyncha (aphids and Carotenoid a whitefly), 11 species of Auchenorrhyncha (planthoppers, leafhoppers, and cicadas), and 20 species of Heter­ Hemiptera optera (stink bugs, assassin bugs, water striders, water scorpions, water bugs, and backswimmers), were Food chain investigated from the viewpoints of chemo-systematic and chemical ecology. In aphids, carotenoids belonging to Chemo-systematics the torulene biosynthetic pathway such as β-zeacarotene, β,ψ-carotene, and torulene, and carotenoids with a Chemical ecology γ-end group such as β,γ-carotene and γ,γ-carotene were identified. Carotenoids belonging the torulene biosyn­ thetic pathway and with a γ-end group were also present in water striders. On the other hand, β-carotene, β-cryptoxanthin, and lutein, which originated from dietary plants, were present in both stink bugs and leaf­ hoppers. Assassin bugs also accumulated carotenoids from dietary insects. Trace amounts of carotenoids were detected in cicadas.
    [Show full text]
  • Structure Elucidation of the Novel Carotenoid
    www.nature.com/scientificreports OPEN Structure elucidation of the novel carotenoid gemmatoxanthin from the photosynthetic complex of Gemmatimonas phototrophica AP64 Nupur1, Marek Kuzma2, Jan Hájek1,3, Pavel Hrouzek1,3, Alastair T. Gardiner1, Martin Lukeš1, Martin Moos4, Petr Šimek4 & Michal Koblížek1* Gemmatimonas phototrophica AP64 is the frst phototrophic representative of the bacterial phylum Gemmatimonadetes. The cells contain photosynthetic complexes with bacteriochlorophyll a as the main light-harvesting pigment and an unknown carotenoid with a single broad absorption band at 490 nm in methanol. The carotenoid was extracted from isolated photosynthetic complexes, and purifed by liquid chromatography. A combination of nuclear magnetic resonance (1H NMR, COSY, 1H-13C HSQC, 1H-13C HMBC, J-resolved, and ROESY), high-resolution mass spectroscopy, Fourier- transformed infra-red, and Raman spectroscopy was used to determine its chemical structure. The novel linear carotenoid, that we have named gemmatoxanthin, contains 11 conjugated double bonds and is further substituted by methoxy, carboxyl and aldehyde groups. Its IUPAC-IUBMB semi- systematic name is 1′-Methoxy-19′-oxo-3′,4′-didehydro-7,8,1′,2′-tetrahydro- Ψ, Ψ carotene-16-oic acid. To our best knowledge, the presence of the carboxyl, methoxy and aldehyde groups on a linear C40 carotenoid backbone is reported here for the frst time. Photosynthesis is an ancient process that probably evolved more than 3 billion years ago 1. It is believed that the earliest phototrophic organisms were anoxygenic (not producing oxygen) species2, which throughout evolution diverged into a number of bacterial phyla. Te latest phylum from which anoxygenic phototrophic species have been isolated is Gemmatimonadetes. Te phylum Gemmatimonadetes was formally established in 2003, with Gemmatimonas (G.) aurantiaca as the type species.
    [Show full text]