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Production of Highly Modified C30-carotenoids with Singlet Oxygen-quenching Activities, 5-glucosyl-5,6-dihydro-4,4’-diapolycopen-4’-oic Acid, and Its Three Intermediates Using Genes from Planococcus maritimus Strain iso-3

Synthetic Biology and Engineering. 2023, 1(1), 10002; https://doi.org/10.35534/sbe.2023.10002
Moe Hagiwara 1,    Chinatsu Maehara 1,    Miho Takemura 2,    Norihiko MIsawa 2, *    Kazutoshi Shindo 1, *   
1
Department of Food and Nutrition, Japan Women´s University, 2-8-1 Mejirodai, Bunkyo-ku, Tokyo 112-8681, Japan
2
Research Institute for Bioresources and Biotechnology, Ishikawa Prefectural University, 1-308 Suematsu, Nonoichi-shi, Ishikawa 921-8836, Japan
*
Authors to whom correspondence should be addressed.

Received: 12 Dec 2022    Accepted: 03 Feb 2023    Published: 07 Feb 2023   

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Abstract

Planococcus maritimus strain iso-3 was previously isolated from intertidal sediment in the North Sea and was found to produce a highly modified C30-carotenoid, methyl-5-glucosyl-5,6-dihydro-4,4’-diapolycopenoate, as the final product. In this study, we analyzed the function of the carotenoid terminal oxidase crtP (renamed cruO) and aldehyde dehydrogenase aldH genes in P. maritimus strain iso-3 and elucidated the carotenoid biosynthetic pathway for this strain at the gene level. We produced four novel C30-carotenoids with potent singlet oxygen-quenching activities, 5-glucosyl-5,6-dihydro-4,4’-diapolycopen-4’-oic acid and its three intermediates, which were obtained using E. coli cells carrying the cruO (and aldH) gene(s) in addition to the known P. maritimus carotenogenic genes.

Keywords

C30-carotenoids; Marine Bacterium; Planococcus; Diapolycopenoic Acid; Singlet Oxygen-quenching Activity

References

1.
Sandmann G, Misawa N. Carotenoid production in Escherichia coli: Case of acyclic carotenoids. In Carotenoids: Biosynthetic and Biofunctional Approaches; Misawa N., Ed.; Springer: Singapore, 2021; pp. 201–208.
2.
Wieland B, Feil C, Gloria-Maercker E, Thumm G, Lechner M, Bravo JM, et al. Genetic and biochemical analyses of the biosynthesis of the yellow carotenoid 4,4′-diaponeurosporene of Staphylococcus aureus. J. Bacteriol. 1994, 176, 7719–7726. [Google Scholar]
3.
Takemura M, Takagi C, Aikawa M, Araki K, Choi S-K, Itaya M, et al. Heterologous production of novel and rare C30-carotenoids using Planococcus carotenoid biosynthesis genes.  Microb. Cell Fact. 2021, 20, 194–205. [Google Scholar]
4.
Shindo K, Endo M, Miyake Y, Wakasugi K, Morritt D, Bramley PM, et al. Methyl glucosyl-3,4-dehydro-apo-8′-lycopenoate, a novel antioxidative glyco-C30-carotenoic acid produced by a marine bacterium Planococcus maritimus. J. Antibiot. 2008, 61, 729–735. [Google Scholar]
5.
Shindo K, Endo M, Miyake Y, Wakasugi K, Morritt D, Bramley PM, et al. Methyl 5-glucosyl-5,6-dihydro-apo-4,4′-lycopenoate, a novel antioxidative glyco-C30-carotenoic acid produced by a marine bacterium Planococcus maritimus.  J. Antibiot. 2014, 67, 731–732. [Google Scholar]
6.
Sun Z, Shen S, Wang C, Wang H, Hu Y, Jiao J, et al. A novel carotenoid 1,2-hydratase (CruF) from two species of the non-photosynthetic bacterium Deinococcus. Microbiology 2009, 155, 2775–2783. [Google Scholar]
7.
Kim SH, Lee PC. Functional expression and extension of Staphylococcal staphyloxanthin biosynthesis pathway in Escherichia coli. J. Biol. Chem. 2012, 287, 21575–21583. [Google Scholar]
8.
Pelz A, Wieland KP, Pitzbach K, Hentschel P, Alberl K, Götz F. Structure and biosynthesis of staphyloxanthin from Staphylococcus aureus. J. Biol. Chem. 2005, 280, 32493–32498. [Google Scholar]
9.
Steiger S, Perez-Fons L, Cutting SM, Fraser PD, Sandmann G. Annotation and functional assignment of the genes for the C30 carotenoid pathways from the genomes of two bacteria: Bacillus indicus and Bacillus firmus. Microbiology 2015, 161, 194–202. [Google Scholar]
10.
Nishida Y, Adachi K, Kasai H, Shizuri Y, Shindo K, Sawabe A, et al. Elucidation of a carotenoid biosynthesis gene cluster encoding a novel enzyme, 2,2′-β-hydroxylase, from Brevundimonas sp. strain SD212 and combinatorial biosynthesis of new or rare xanthophylls. Appl. Environ. Microbiol. 2005, 71, 4286–4296. [Google Scholar]
11.
Fraser PD, Pinto MES, Holloway DE, Bramley PM. Application of high-performance liquid chromatography with photodiode array detection to the metabolic profiling of plant isoprenoids. Plant J. 2000, 24, 551–558. [Google Scholar]
12.
Yokoyama A, Miki W. Composition and presumed biosynthetic pathway of carotenoids in the astaxanthin-producing bacterium Agrobacterium aurantiacum. FEMS Microbiol. Lett. 1995, 128, 139–144. [Google Scholar]
13.
Lee JH, Kim JW, Lee PC. Genome mining reveals two missing CrtP and AldH enzymes in the C30 carotenoid biosynthesis pathway in Planococcus faecalis AJ003T. Molecules 2020, 25, 5892. [Google Scholar]
14.
Harker M, Hirschberg J. Molecular biology of carotenoid biosynthesis in photosynthetic organisms. Methods Enzymol. 1998, 297, 244–263. [Google Scholar]
15.
Tao L, Schenzle A, Odom JM, Cheng Q. Novel carotenoid oxidase involved in biosynthesis of 4,4′-diapophytoene dialdehyde. Appl. Envion. Microbiol. 2005, 71, 3294–3301. [Google Scholar]
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© 2023 by the authors; licensee SCIEPublish, SCISCAN co. Ltd. This article is an open access article distributed under the CC BY license (http://creativecommons.org/licenses/by/4.0/).