{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T09:22:03Z","timestamp":1790846523003,"version":"4.1.0"},"reference-count":83,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2023,2,2]],"date-time":"2023-02-02T00:00:00Z","timestamp":1675296000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"S\u00e3o Paulo Research Foundation","award":["#2016\/14227-5"],"award-info":[{"award-number":["#2016\/14227-5"]}]},{"name":"S\u00e3o Paulo Research Foundation","award":["2013\/07914-8"],"award-info":[{"award-number":["2013\/07914-8"]}]},{"name":"S\u00e3o Paulo Research Foundation","award":["2021\/00149-0"],"award-info":[{"award-number":["2021\/00149-0"]}]},{"name":"S\u00e3o Paulo Research Foundation","award":["#433166\/2018-5"],"award-info":[{"award-number":["#433166\/2018-5"]}]},{"name":"S\u00e3o Paulo Research Foundation","award":["#439065\/2018-6"],"award-info":[{"award-number":["#439065\/2018-6"]}]},{"name":"S\u00e3o Paulo Research Foundation","award":["13.1.1502.9.8"],"award-info":[{"award-number":["13.1.1502.9.8"]}]},{"name":"S\u00e3o Paulo Research Foundation","award":["001"],"award-info":[{"award-number":["001"]}]},{"name":"S\u00e3o Paulo Research Foundation","award":["140892\/2020-6"],"award-info":[{"award-number":["140892\/2020-6"]}]},{"name":"S\u00e3o Paulo Research Foundation","award":["88887.695454\/2022-00"],"award-info":[{"award-number":["88887.695454\/2022-00"]}]},{"name":"S\u00e3o Paulo Research Foundation","award":["#2019\/27707-3"],"award-info":[{"award-number":["#2019\/27707-3"]}]},{"name":"S\u00e3o Paulo Research Foundation","award":["#306803\/2018-6"],"award-info":[{"award-number":["#306803\/2018-6"]}]},{"name":"S\u00e3o Paulo Research Foundation","award":["#313970\/2020-3"],"award-info":[{"award-number":["#313970\/2020-3"]}]},{"name":"National Council for Scientific and Technological Development","award":["#2016\/14227-5"],"award-info":[{"award-number":["#2016\/14227-5"]}]},{"name":"National Council for Scientific and Technological Development","award":["2013\/07914-8"],"award-info":[{"award-number":["2013\/07914-8"]}]},{"name":"National Council for Scientific and Technological Development","award":["2021\/00149-0"],"award-info":[{"award-number":["2021\/00149-0"]}]},{"name":"National Council for Scientific and Technological Development","award":["#433166\/2018-5"],"award-info":[{"award-number":["#433166\/2018-5"]}]},{"name":"National Council for Scientific and Technological Development","award":["#439065\/2018-6"],"award-info":[{"award-number":["#439065\/2018-6"]}]},{"name":"National Council for Scientific and Technological Development","award":["13.1.1502.9.8"],"award-info":[{"award-number":["13.1.1502.9.8"]}]},{"name":"National Council for Scientific and Technological Development","award":["001"],"award-info":[{"award-number":["001"]}]},{"name":"National Council for Scientific and Technological Development","award":["140892\/2020-6"],"award-info":[{"award-number":["140892\/2020-6"]}]},{"name":"National Council for Scientific and Technological Development","award":["88887.695454\/2022-00"],"award-info":[{"award-number":["88887.695454\/2022-00"]}]},{"name":"National Council for Scientific and Technological Development","award":["#2019\/27707-3"],"award-info":[{"award-number":["#2019\/27707-3"]}]},{"name":"National Council for Scientific and Technological Development","award":["#306803\/2018-6"],"award-info":[{"award-number":["#306803\/2018-6"]}]},{"name":"National Council for Scientific and Technological Development","award":["#313970\/2020-3"],"award-info":[{"award-number":["#313970\/2020-3"]}]},{"DOI":"10.13039\/501100005639","name":"USP","doi-asserted-by":"publisher","award":["#2016\/14227-5"],"award-info":[{"award-number":["#2016\/14227-5"]}],"id":[{"id":"10.13039\/501100005639","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005639","name":"USP","doi-asserted-by":"publisher","award":["2013\/07914-8"],"award-info":[{"award-number":["2013\/07914-8"]}],"id":[{"id":"10.13039\/501100005639","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005639","name":"USP","doi-asserted-by":"publisher","award":["2021\/00149-0"],"award-info":[{"award-number":["2021\/00149-0"]}],"id":[{"id":"10.13039\/501100005639","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005639","name":"USP","doi-asserted-by":"publisher","award":["#433166\/2018-5"],"award-info":[{"award-number":["#433166\/2018-5"]}],"id":[{"id":"10.13039\/501100005639","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005639","name":"USP","doi-asserted-by":"publisher","award":["#439065\/2018-6"],"award-info":[{"award-number":["#439065\/2018-6"]}],"id":[{"id":"10.13039\/501100005639","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005639","name":"USP","doi-asserted-by":"publisher","award":["13.1.1502.9.8"],"award-info":[{"award-number":["13.1.1502.9.8"]}],"id":[{"id":"10.13039\/501100005639","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005639","name":"USP","doi-asserted-by":"publisher","award":["001"],"award-info":[{"award-number":["001"]}],"id":[{"id":"10.13039\/501100005639","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005639","name":"USP","doi-asserted-by":"publisher","award":["140892\/2020-6"],"award-info":[{"award-number":["140892\/2020-6"]}],"id":[{"id":"10.13039\/501100005639","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005639","name":"USP","doi-asserted-by":"publisher","award":["88887.695454\/2022-00"],"award-info":[{"award-number":["88887.695454\/2022-00"]}],"id":[{"id":"10.13039\/501100005639","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005639","name":"USP","doi-asserted-by":"publisher","award":["#2019\/27707-3"],"award-info":[{"award-number":["#2019\/27707-3"]}],"id":[{"id":"10.13039\/501100005639","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005639","name":"USP","doi-asserted-by":"publisher","award":["#306803\/2018-6"],"award-info":[{"award-number":["#306803\/2018-6"]}],"id":[{"id":"10.13039\/501100005639","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005639","name":"USP","doi-asserted-by":"publisher","award":["#313970\/2020-3"],"award-info":[{"award-number":["#313970\/2020-3"]}],"id":[{"id":"10.13039\/501100005639","id-type":"DOI","asserted-by":"publisher"}]},{"name":"the Brazilian Federal Agency for the Support and Evaluation of Graduate Education","award":["#2016\/14227-5"],"award-info":[{"award-number":["#2016\/14227-5"]}]},{"name":"the Brazilian Federal Agency for the Support and Evaluation of Graduate Education","award":["2013\/07914-8"],"award-info":[{"award-number":["2013\/07914-8"]}]},{"name":"the Brazilian Federal Agency for the Support and Evaluation of Graduate Education","award":["2021\/00149-0"],"award-info":[{"award-number":["2021\/00149-0"]}]},{"name":"the Brazilian Federal Agency for the Support and Evaluation of Graduate Education","award":["#433166\/2018-5"],"award-info":[{"award-number":["#433166\/2018-5"]}]},{"name":"the Brazilian Federal Agency for the Support and Evaluation of Graduate Education","award":["#439065\/2018-6"],"award-info":[{"award-number":["#439065\/2018-6"]}]},{"name":"the Brazilian Federal Agency for the Support and Evaluation of Graduate Education","award":["13.1.1502.9.8"],"award-info":[{"award-number":["13.1.1502.9.8"]}]},{"name":"the Brazilian Federal Agency for the Support and Evaluation of Graduate Education","award":["001"],"award-info":[{"award-number":["001"]}]},{"name":"the Brazilian Federal Agency for the Support and Evaluation of Graduate Education","award":["140892\/2020-6"],"award-info":[{"award-number":["140892\/2020-6"]}]},{"name":"the Brazilian Federal Agency for the Support and Evaluation of Graduate Education","award":["88887.695454\/2022-00"],"award-info":[{"award-number":["88887.695454\/2022-00"]}]},{"name":"the Brazilian Federal Agency for the Support and Evaluation of Graduate Education","award":["#2019\/27707-3"],"award-info":[{"award-number":["#2019\/27707-3"]}]},{"name":"the Brazilian Federal Agency for the Support and Evaluation of Graduate Education","award":["#306803\/2018-6"],"award-info":[{"award-number":["#306803\/2018-6"]}]},{"name":"the Brazilian Federal Agency for the Support and Evaluation of Graduate Education","award":["#313970\/2020-3"],"award-info":[{"award-number":["#313970\/2020-3"]}]},{"name":"CNPq","award":["#2016\/14227-5"],"award-info":[{"award-number":["#2016\/14227-5"]}]},{"name":"CNPq","award":["2013\/07914-8"],"award-info":[{"award-number":["2013\/07914-8"]}]},{"name":"CNPq","award":["2021\/00149-0"],"award-info":[{"award-number":["2021\/00149-0"]}]},{"name":"CNPq","award":["#433166\/2018-5"],"award-info":[{"award-number":["#433166\/2018-5"]}]},{"name":"CNPq","award":["#439065\/2018-6"],"award-info":[{"award-number":["#439065\/2018-6"]}]},{"name":"CNPq","award":["13.1.1502.9.8"],"award-info":[{"award-number":["13.1.1502.9.8"]}]},{"name":"CNPq","award":["001"],"award-info":[{"award-number":["001"]}]},{"name":"CNPq","award":["140892\/2020-6"],"award-info":[{"award-number":["140892\/2020-6"]}]},{"name":"CNPq","award":["88887.695454\/2022-00"],"award-info":[{"award-number":["88887.695454\/2022-00"]}]},{"name":"CNPq","award":["#2019\/27707-3"],"award-info":[{"award-number":["#2019\/27707-3"]}]},{"name":"CNPq","award":["#306803\/2018-6"],"award-info":[{"award-number":["#306803\/2018-6"]}]},{"name":"CNPq","award":["#313970\/2020-3"],"award-info":[{"award-number":["#313970\/2020-3"]}]},{"name":"CAPES","award":["#2016\/14227-5"],"award-info":[{"award-number":["#2016\/14227-5"]}]},{"name":"CAPES","award":["2013\/07914-8"],"award-info":[{"award-number":["2013\/07914-8"]}]},{"name":"CAPES","award":["2021\/00149-0"],"award-info":[{"award-number":["2021\/00149-0"]}]},{"name":"CAPES","award":["#433166\/2018-5"],"award-info":[{"award-number":["#433166\/2018-5"]}]},{"name":"CAPES","award":["#439065\/2018-6"],"award-info":[{"award-number":["#439065\/2018-6"]}]},{"name":"CAPES","award":["13.1.1502.9.8"],"award-info":[{"award-number":["13.1.1502.9.8"]}]},{"name":"CAPES","award":["001"],"award-info":[{"award-number":["001"]}]},{"name":"CAPES","award":["140892\/2020-6"],"award-info":[{"award-number":["140892\/2020-6"]}]},{"name":"CAPES","award":["88887.695454\/2022-00"],"award-info":[{"award-number":["88887.695454\/2022-00"]}]},{"name":"CAPES","award":["#2019\/27707-3"],"award-info":[{"award-number":["#2019\/27707-3"]}]},{"name":"CAPES","award":["#306803\/2018-6"],"award-info":[{"award-number":["#306803\/2018-6"]}]},{"name":"CAPES","award":["#313970\/2020-3"],"award-info":[{"award-number":["#313970\/2020-3"]}]},{"name":"FAPESP","award":["#2016\/14227-5"],"award-info":[{"award-number":["#2016\/14227-5"]}]},{"name":"FAPESP","award":["2013\/07914-8"],"award-info":[{"award-number":["2013\/07914-8"]}]},{"name":"FAPESP","award":["2021\/00149-0"],"award-info":[{"award-number":["2021\/00149-0"]}]},{"name":"FAPESP","award":["#433166\/2018-5"],"award-info":[{"award-number":["#433166\/2018-5"]}]},{"name":"FAPESP","award":["#439065\/2018-6"],"award-info":[{"award-number":["#439065\/2018-6"]}]},{"name":"FAPESP","award":["13.1.1502.9.8"],"award-info":[{"award-number":["13.1.1502.9.8"]}]},{"name":"FAPESP","award":["001"],"award-info":[{"award-number":["001"]}]},{"name":"FAPESP","award":["140892\/2020-6"],"award-info":[{"award-number":["140892\/2020-6"]}]},{"name":"FAPESP","award":["88887.695454\/2022-00"],"award-info":[{"award-number":["88887.695454\/2022-00"]}]},{"name":"FAPESP","award":["#2019\/27707-3"],"award-info":[{"award-number":["#2019\/27707-3"]}]},{"name":"FAPESP","award":["#306803\/2018-6"],"award-info":[{"award-number":["#306803\/2018-6"]}]},{"name":"FAPESP","award":["#313970\/2020-3"],"award-info":[{"award-number":["#313970\/2020-3"]}]},{"name":"research fellowships","award":["#2016\/14227-5"],"award-info":[{"award-number":["#2016\/14227-5"]}]},{"name":"research fellowships","award":["2013\/07914-8"],"award-info":[{"award-number":["2013\/07914-8"]}]},{"name":"research fellowships","award":["2021\/00149-0"],"award-info":[{"award-number":["2021\/00149-0"]}]},{"name":"research fellowships","award":["#433166\/2018-5"],"award-info":[{"award-number":["#433166\/2018-5"]}]},{"name":"research fellowships","award":["#439065\/2018-6"],"award-info":[{"award-number":["#439065\/2018-6"]}]},{"name":"research fellowships","award":["13.1.1502.9.8"],"award-info":[{"award-number":["13.1.1502.9.8"]}]},{"name":"research fellowships","award":["001"],"award-info":[{"award-number":["001"]}]},{"name":"research fellowships","award":["140892\/2020-6"],"award-info":[{"award-number":["140892\/2020-6"]}]},{"name":"research fellowships","award":["88887.695454\/2022-00"],"award-info":[{"award-number":["88887.695454\/2022-00"]}]},{"name":"research fellowships","award":["#2019\/27707-3"],"award-info":[{"award-number":["#2019\/27707-3"]}]},{"name":"research fellowships","award":["#306803\/2018-6"],"award-info":[{"award-number":["#306803\/2018-6"]}]},{"name":"research fellowships","award":["#313970\/2020-3"],"award-info":[{"award-number":["#313970\/2020-3"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Cyanobacteria are oxygenic phototrophic prokaryotes that have evolved to produce ultraviolet-screening mycosporine-like amino acids (MAAs) to lessen harmful effects from obligatory exposure to solar UV radiation. The cyanobacterial MAA biosynthetic cluster is formed by a gene encoding 2-epi-5-epi-valiolone synthase (EVS) located immediately upstream from an O-methyltransferase (OMT) encoding gene, which together biosynthesize the expected MAA precursor 4-deoxygadusol. Accordingly, these genes are typically absent in non-producers. In this study, the relationship between gene cluster architecture and constitutive production of MAAs was evaluated in cyanobacteria isolated from various Brazilian biomes. Constitutive production of MAAs was only detected in strains where genes formed a co-linear cluster. Expectedly, this production was enhanced upon exposure of the strains to UV irradiance and by using distinct culture media. Constitutive production of MAAs was not detected in all other strains and, unexpectedly, production could not be induced by exposure to UV irradiation or changing growth media. Other photoprotection strategies which might be employed by these MAA non-producing strains are discussed. The evolutionary and ecological significance of gene order conservation warrants closer experimentation, which may provide a first insight into regulatory interactions of genes encoding enzymes for MAA biosynthesis.<\/jats:p>","DOI":"10.3390\/molecules28031420","type":"journal-article","created":{"date-parts":[[2023,2,2]],"date-time":"2023-02-02T02:21:12Z","timestamp":1675304472000},"page":"1420","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Exploring the Relationship between Biosynthetic Gene Clusters and Constitutive Production of Mycosporine-like Amino Acids in Brazilian Cyanobacteria"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0602-7584","authenticated-orcid":false,"given":"Rafael B.","family":"Dextro","sequence":"first","affiliation":[{"name":"Center for Nuclear Energy in Agriculture (CENA), University of S\u00e3o Paulo (USP), Avenida Centen\u00e1rio 303, Piracicaba 13416-000, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0313-9046","authenticated-orcid":false,"given":"Endrews","family":"Delbaje","sequence":"additional","affiliation":[{"name":"Center for Nuclear Energy in Agriculture (CENA), University of S\u00e3o Paulo (USP), Avenida Centen\u00e1rio 303, Piracicaba 13416-000, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vanessa","family":"Geraldes","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences, University of S\u00e3o Paulo (USP), Avenida Prof. Lineu Prestes 580, S\u00e3o Paulo 05508-000, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7614-3014","authenticated-orcid":false,"given":"Ernani","family":"Pinto","sequence":"additional","affiliation":[{"name":"Center for Nuclear Energy in Agriculture (CENA), University of S\u00e3o Paulo (USP), Avenida Centen\u00e1rio 303, Piracicaba 13416-000, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paul F.","family":"Long","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences, University of S\u00e3o Paulo (USP), Avenida Prof. Lineu Prestes 580, S\u00e3o Paulo 05508-000, Brazil"},{"name":"Faculty of Life Sciences & Medicine, King\u2019s College London, London SE1 9NH, UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2555-7967","authenticated-orcid":false,"given":"Marli F.","family":"Fiore","sequence":"additional","affiliation":[{"name":"Center for Nuclear Energy in Agriculture (CENA), University of S\u00e3o Paulo (USP), Avenida Centen\u00e1rio 303, Piracicaba 13416-000, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,2,2]]},"reference":[{"key":"ref_1","first-page":"1","article-title":"Cyanobacteria. Oxygenic photosynthetic bacteria","volume":"Volume 410","author":"Whitman","year":"2015","journal-title":"Bergey\u2019s Manual of Systematics of Archaea and Bacteria"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1890\/ES14-00174.1","article-title":"Cyanobacteria as biological drivers of lake nitrogen and phosphorus cycling","volume":"6","author":"Cottingham","year":"2015","journal-title":"Ecosphere"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"278","DOI":"10.1016\/j.plantsci.2007.12.004","article-title":"UV-protectants in cyanobacteria","volume":"174","author":"Sinha","year":"2008","journal-title":"Plant Sci."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"7053","DOI":"10.1007\/s00253-021-11467-9","article-title":"Recent advances in the discovery of novel marine natural products and mycosporine-like amino acid UV-absorbing compounds","volume":"105","author":"Rosic","year":"2021","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1017\/S0006323199005356","article-title":"Ultraviolet radiation screening compounds","volume":"74","author":"Cockell","year":"1999","journal-title":"Biol. Rev. Camb. Philos. Soc."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1353","DOI":"10.1111\/bjd.16125","article-title":"Molecular photoprotection of human keratinocytes in vitro by the naturally occurring mycosporine-like amino acid palythine","volume":"178","author":"Lawrence","year":"2018","journal-title":"Br. J. Dermatol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1653","DOI":"10.1126\/science.1193637","article-title":"The genetic and molecular basis for sunscreen biosynthesis in cyanobacteria","volume":"329","author":"Balskus","year":"2010","journal-title":"Science"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"120","DOI":"10.1016\/j.ygeno.2009.10.002","article-title":"Genome mining of mycosporine-like amino acid (MAA) synthesizing and non-synthesizing cyanobacteria: A bioinformatics study","volume":"95","author":"Singh","year":"2010","journal-title":"Genomics"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"240","DOI":"10.1016\/j.jphotobiol.2006.10.006","article-title":"Protective effects of mycosporine-like amino acids of Synechocystis sp. PCC 6803 and their partial characterization","volume":"86","author":"Zhang","year":"2007","journal-title":"J. Photochem. Photobiol. B Biol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"531","DOI":"10.1002\/cbic.201100737","article-title":"Redundant pathways of sunscreen biosynthesis in a cyanobacterium","volume":"13","author":"Spence","year":"2012","journal-title":"ChemBioChem"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"320","DOI":"10.1002\/cbic.201402516","article-title":"O-Methyltransferase is shared between the pentose phosphate and shikimate pathways and is essential for mycosporine-like amino acid biosynthesis in Anabaena variabilis ATCC 29413","volume":"16","author":"Pope","year":"2015","journal-title":"ChemBioChem"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1548","DOI":"10.1111\/1462-2920.12577","article-title":"Functional assessment of mycosporine-like amino acids in Microcystis aeruginosa strain PCC 7806","volume":"17","author":"Hu","year":"2015","journal-title":"Environ. Microbiol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"6167","DOI":"10.1128\/AEM.01632-16","article-title":"Heterologous production of cyanobacterial mycosporine-like amino acids mycosporine-ornithine and mycosporine-lysine in Escherichia coli","volume":"82","author":"Katoch","year":"2016","journal-title":"Appl. Environ. Microbiol."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"5923","DOI":"10.1128\/JB.05730-11","article-title":"An ATP-grasp ligase involved in the last biosynthetic step of the iminomycosporine shinorine in Nostoc punctiforme ATCC 29133","volume":"193","author":"Gao","year":"2011","journal-title":"J. Bacteriol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"5512","DOI":"10.2174\/0929867324666170529124237","article-title":"Mycosporine-like amino acids for skin photoprotection","volume":"25","author":"Lawrence","year":"2018","journal-title":"Curr. Med. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Geraldes, V., and Pinto, E. (2021). Mycosporine-like amino acids (MAAs): Biology, chemistry and identification features. Pharmaceuticals, 14.","DOI":"10.3390\/ph14010063"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1111\/j.1529-8817.1968.tb04667.x","article-title":"Simple conditions for growth of unicellular blue-green algae on plates 1, 2","volume":"4","author":"Allen","year":"1968","journal-title":"J. Phycol."},{"key":"ref_18","first-page":"796","article-title":"Isolation and culture of toxic strains of Anabaena flos-aquae (Lyngb.) de Br\u00e9b","volume":"15","author":"Gorham","year":"1964","journal-title":"Int. Verein. Theor. Angew. Limmol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"e00466\u2013e16","DOI":"10.1128\/genomeA.00466-16","article-title":"Draft genome assembly of the bloom-forming cyanobacterium Nodularia spumigena strain CENA596 in shrimp production ponds","volume":"4","author":"Popin","year":"2016","journal-title":"Genome Announc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"769","DOI":"10.1021\/acschembio.6b00948","article-title":"Genetic organization of anabaenopeptin and spumigin biosynthetic gene clusters in the cyanobacterium Sphaerospermopsis torques-reginae ITEP-024","volume":"12","author":"Lima","year":"2017","journal-title":"ACS Chem. Biol."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"675","DOI":"10.1111\/jpy.12192","article-title":"Nonheterocytous cyanobacteria from Brazilian saline-alkaline lakes","volume":"50","author":"Andreote","year":"2014","journal-title":"J. Phycol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"004648","DOI":"10.1099\/ijsem.0.004648","article-title":"Phylogenomic analysis of Anabaenopsis elenkinii (Nostocales, Cyanobacteria)","volume":"71","author":"Delbaje","year":"2021","journal-title":"Int. J. Syst. Evol. Microbiol."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"789","DOI":"10.1111\/j.1529-8817.2007.00376.x","article-title":"The cyanobacterial genus Brasilonema, gen. nov., a molecular and phenotypic evaluation 1","volume":"43","author":"Fiore","year":"2007","journal-title":"J. Phycol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1322","DOI":"10.1111\/j.1529-8817.2008.00584.x","article-title":"A novel epiphytic cyanobacterial species from the genus Brasilonema causing damage to Eucalyptus leaves","volume":"44","author":"Aguiar","year":"2008","journal-title":"J. Phycol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"D427","DOI":"10.1093\/nar\/gky995","article-title":"The Pfam protein families database in 2019","volume":"47","author":"Mistry","year":"2019","journal-title":"Nucleic Acids Res."},{"key":"ref_26","first-page":"304","article-title":"Toward a data mining service from large and heterogeneous genome databases in GenomeNet","volume":"10","author":"Fuseda","year":"1999","journal-title":"Genome Inform."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1093\/nar\/30.1.42","article-title":"The KEGG databases at GenomeNet","volume":"30","author":"Kanehisa","year":"2002","journal-title":"Nucleic Acids Res."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Camacho, C., Coulouris, G., Avagyan, V., Ma, N., Papadopoulos, J., Bealer, K., and Madden, T.L. (2009). BLAST+: Architecture and applications. BMC Bioinform., 10.","DOI":"10.1186\/1471-2105-10-421"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"W29","DOI":"10.1093\/nar\/gkt282","article-title":"BLAST: A more efficient report with usability improvements","volume":"41","author":"Boratyn","year":"2013","journal-title":"Nucleic Acids Res."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"464","DOI":"10.1093\/bioinformatics\/btr703","article-title":"Artemis: An integrated platform for visualization and analysis of high-throughput sequence-based experimental data","volume":"28","author":"Carver","year":"2012","journal-title":"Bioinformatics"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"101796","DOI":"10.1016\/j.algal.2020.101796","article-title":"Development and validation of a rapid LC-MS\/MS method for the quantification of mycosporines and mycosporine-like amino acids (MAAs) from cyanobacteria","volume":"46","author":"Geraldes","year":"2020","journal-title":"Algal Res."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1925","DOI":"10.1093\/bioinformatics\/btz848","article-title":"GTDB-Tk: A toolkit to classify genomes with the Genome Taxonomy Database","volume":"36","author":"Chaumeil","year":"2019","journal-title":"Bioinformatics"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1093\/bioinformatics\/btl529","article-title":"Interactive Tree Of Life (iTOL): An online tool for phylogenetic tree display and annotation","volume":"23","author":"Letunic","year":"2007","journal-title":"Bioinformatics"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"W465","DOI":"10.1093\/nar\/gkn180","article-title":"Phylogeny. fr: Robust phylogenetic analysis for the non-specialist","volume":"36","author":"Dereeper","year":"2008","journal-title":"Nucleic Acids Res."},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Dereeper, A., Audic, S., Claverie, J.M., and Blanc, G. (2010). BLAST-EXPLORER helps you building datasets for phylogenetic analysis. BMC Evol. Biol., 10.","DOI":"10.1186\/1471-2148-10-8"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1792","DOI":"10.1093\/nar\/gkh340","article-title":"MUSCLE: Multiple sequence alignment with high accuracy and high throughput","volume":"32","author":"Edgar","year":"2004","journal-title":"Nucleic Acids Res."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"540","DOI":"10.1093\/oxfordjournals.molbev.a026334","article-title":"Selection of conserved blocks from multiple alignments for their use in phylogenetic analysis","volume":"17","author":"Castresana","year":"2000","journal-title":"Mol. Biol. Evol."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"696","DOI":"10.1080\/10635150390235520","article-title":"A simple, fast, and accurate algorithm to estimate large phylogenies by maximum likelihood","volume":"52","author":"Guindon","year":"2003","journal-title":"Syst. Biol."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"539","DOI":"10.1080\/10635150600755453","article-title":"Approximate likelihood-ratio test for branches: A fast, accurate, and powerful alternative","volume":"55","author":"Anisimova","year":"2006","journal-title":"Syst. Biol."},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Chevenet, F., Brun, C., Ba\u00f1uls, A.L., Jacq, B., and Christen, R. (2006). TreeDyn: Towards dynamic graphics and annotations for analyses of trees. BMC Bioinform., 7.","DOI":"10.1186\/1471-2105-7-439"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1111\/jpy.13219","article-title":"Gene clusters for biosynthesis of mycosporine-like amino acids in dinoflagellate nuclear genomes: Possible recent horizontal gene transfer between species of Symbiodiniaceae (Dinophyceae)","volume":"58","author":"Shoguchi","year":"2022","journal-title":"J. Phycol."},{"key":"ref_42","first-page":"311","article-title":"A handbook of seawater analysis","volume":"167","author":"Strickland","year":"1968","journal-title":"Bull. Fish. Res. Board Can."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"523","DOI":"10.1016\/0006-291X(65)90516-4","article-title":"Dependence of chloroplast pigment synthesis on protein synthesis: Effect of actidione","volume":"21","author":"Kirk","year":"1965","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_44","first-page":"177","article-title":"Genetic and biochemical evidence for redundant pathways leading to mycosporine-like amino acid biosynthesis in the cyanobacterium Sphaerospermopsis torques-reginae ITEP-024","volume":"35","author":"Geraldes","year":"2020","journal-title":"Harmful Algae"},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Wang, H., Fewer, D.P., and Sivonen, K. (2011). Genome mining demonstrates the widespread occurrence of gene clusters encoding bacteriocins in cyanobacteria. PLoS ONE, 6.","DOI":"10.1371\/journal.pone.0022384"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"11160","DOI":"10.1021\/acs.joc.1c00368","article-title":"Biosynthesis and Heterologous Production of Mycosporine-Like Amino Acid Palythines","volume":"86","author":"Chen","year":"2021","journal-title":"J. Org. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"4465","DOI":"10.1128\/JB.01816-06","article-title":"Molecular genetics and genomic analysis of scytonemin biosynthesis in Nostoc punctiforme ATCC 29133","volume":"189","author":"Soule","year":"2007","journal-title":"J. Bacteriol."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1500","DOI":"10.1111\/j.1751-1097.2008.00376.x","article-title":"Effects of abiotic stressors on synthesis of the mycosporine-like amino acid shinorine in the cyanobacterium Anabaena variabilis PCC 7937","volume":"84","author":"Singh","year":"2008","journal-title":"Photochem. Photobiol."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"E6361","DOI":"10.1073\/pnas.1703088114","article-title":"Insights into the red algae and eukaryotic evolution from the genome of Porphyra umbilicalis (Bangiophyceae, Rhodophyta)","volume":"114","author":"Brawley","year":"2017","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1111\/1462-2920.13972","article-title":"UV-B induced biosynthesis of a novel sunscreen compound in solar radiation and desiccation tolerant cyanobacteria","volume":"20","author":"Shang","year":"2018","journal-title":"Environ. Microbiol."},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Le Moigne, D., Demay, J., Reinhardt, A., Bernard, C., Tiam, S.K., and Marie, B. (2021). Dynamics of the Metabolome of Aliinostoc sp. PMC 882.14 in Response to Light and Temperature Variations. Metabolites, 11.","DOI":"10.3390\/metabo11110745"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1016\/S1011-1344(99)00103-7","article-title":"Induction of a mycosporine-like amino acid (MAA) in the rice-field cyanobacterium Anabaena sp. by UV irradiation","volume":"52","author":"Sinha","year":"1999","journal-title":"J. Photochem. Photobiol. B Biol."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"675","DOI":"10.1007\/s00248-008-9427-2","article-title":"Interaction effects of ambient UV radiation and nutrient limitation on the toxic cyanobacterium Nodularia spumigena","volume":"57","author":"Mohlin","year":"2009","journal-title":"Microb. Ecol."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"110","DOI":"10.1016\/j.algal.2016.03.009","article-title":"Characterization and antioxidant functions of mycosporine-like amino acids in the cyanobacterium Nostoc sp. R76DM","volume":"16","author":"Rastogi","year":"2016","journal-title":"Algal Res."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"20638","DOI":"10.1038\/s41598-020-77402-6","article-title":"Mycosporine-like amino acid and aromatic amino acid transcriptome response to UV and far-red light in the cyanobacterium Chlorogloeopsis fritschii PCC 6912","volume":"10","author":"Llewellyn","year":"2020","journal-title":"Sci. Rep."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"100749","DOI":"10.1016\/j.biteb.2021.100749","article-title":"Evaluation of UV-B protection efficiency of mycosporine like amino acid extracted from the cyanobacteria Anabaenopsis sp. SLCyA isolated from a hypersaline lake","volume":"15","author":"Bairwa","year":"2021","journal-title":"Bioresour. Technol. Rep."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"316","DOI":"10.1080\/09670262.2020.1824019","article-title":"UV-B irradiation enhances the production of unique mycosporine-like amino acids and carotenoids in the subaerial cyanobacterium Pseudanabaena sp. CCNU1","volume":"56","author":"Boucar","year":"2021","journal-title":"Eur. J. Phycol."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"228","DOI":"10.2216\/11-32.1","article-title":"Morphological and molecular studies of Sphaerospermopsis torques-reginae (Cyanobacteria, Nostocales) from South American water blooms","volume":"51","author":"Werner","year":"2012","journal-title":"Phycologia"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1080\/09670269710001737269","article-title":"Strategies of adaptation by Antarctic cyanobacteria to ultraviolet radiation","volume":"32","author":"Quesada","year":"1997","journal-title":"Eur. J. Phycol."},{"key":"ref_60","doi-asserted-by":"crossref","unstructured":"Demay, J., Bernard, C., Reinhardt, A., and Marie, B. (2019). Natural products from cyanobacteria: Focus on beneficial activities. Mar. Drugs, 17.","DOI":"10.20944\/preprints201904.0192.v1"},{"key":"ref_61","doi-asserted-by":"crossref","unstructured":"Amsler, C.D. (2008). Algal Chemical Ecology, Springer.","DOI":"10.1007\/978-3-540-74181-7"},{"key":"ref_62","doi-asserted-by":"crossref","unstructured":"Whitton, B.A. (2012). Ecology of Cyanobacteria II, Springer.","DOI":"10.1007\/978-94-007-3855-3"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"1500","DOI":"10.1128\/aem.60.5.1500-1511.1994","article-title":"Diel migrations of microorganisms within a benthic, hypersaline mat community","volume":"60","author":"Mechling","year":"1994","journal-title":"Appl. Environ. Microbiol."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1006\/jtbi.1995.0122","article-title":"Tandem genes and clustered genes","volume":"175","author":"Graham","year":"1995","journal-title":"J. Theor. Biol."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"336","DOI":"10.1186\/1471-2164-10-336","article-title":"A comparative genomics approach to understanding the biosynthesis of the sunscreen scytonemin in cyanobacteria","volume":"10","author":"Soule","year":"2009","journal-title":"BMC Genom."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"2607","DOI":"10.1007\/s00018-007-7190-z","article-title":"Carotenoids and carotenogenesis in cyanobacteria: Unique ketocarotenoids and carotenoid glycosides","volume":"64","author":"Takaichi","year":"2007","journal-title":"Cell. Mol. Life Sci."},{"key":"ref_67","first-page":"165","article-title":"Ultraviolet radiation-absorbing mycosporine-like amino acids in cyanobacterium Aulosira fertilissima: Environmental perspective and characterization","volume":"3","author":"Mushir","year":"2011","journal-title":"Curr. Res. J. Biol. Sci."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"6291","DOI":"10.3390\/md13106291","article-title":"Analysis of mycosporine-like amino acids in selected algae and cyanobacteria by hydrophilic interaction liquid chromatography and a novel MAA from the red alga Catenella repens","volume":"13","author":"Hartmann","year":"2015","journal-title":"Mar. Drugs"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"1125","DOI":"10.1007\/s10811-017-1328-7","article-title":"Epilithic Chamaesiphon (Synechococcales, Cyanobacteria) species in mountain streams of the Alps-interspecific differences in photo-physiological traits","volume":"30","author":"Aigner","year":"2018","journal-title":"J. Appl. Phycol."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"1392","DOI":"10.1111\/jpy.13200","article-title":"Trends in Free-access Genomic Data Accelerate Advances in Cyanobacteria Taxonomy","volume":"57","author":"Dextro","year":"2021","journal-title":"J. Phycol."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"435","DOI":"10.1080\/00288330.1987.9516239","article-title":"Micronutrient effects on cyanobacterial growth and physiology","volume":"21","author":"Rueter","year":"1987","journal-title":"N. Z. J. Mar. Freshwater Res."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"2021","DOI":"10.1590\/0001-3765201720150707","article-title":"Effects of nutritional conditions on lipid production by cyanobacteria","volume":"89","author":"Cordeiro","year":"2017","journal-title":"An. Acad. Bras. Cien."},{"key":"ref_73","doi-asserted-by":"crossref","unstructured":"McClintock, J.B., and Baker, B.J. (2001). Marine Chemical Ecology, CRC Press. [1st ed.].","DOI":"10.1201\/9781420036602"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"862","DOI":"10.1111\/j.1751-1097.2010.00736.x","article-title":"Sulfur deficiency changes mycosporine-like amino acid (MAA) composition of Anabaena variabilis PCC 7937: A possible role of sulfur in MAA bioconversion","volume":"86","author":"Singh","year":"2010","journal-title":"Photochem. Photobiol."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"3111","DOI":"10.1007\/s11274-008-9831-2","article-title":"Role of various growth media on shinorine (mycosporine-like amino acid) concentration and photosynthetic yield in Anabaena variabilis PCC 7937","volume":"24","author":"Singh","year":"2008","journal-title":"World J. Microbiol. Biotechnol."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"98","DOI":"10.3390\/md12010098","article-title":"Exploring bioactive properties of marine cyanobacteria isolated from the Portuguese coast: High potential as a source of anticancer compounds","volume":"12","author":"Costa","year":"2014","journal-title":"Mar. Drugs"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"879","DOI":"10.1007\/s10811-016-1003-4","article-title":"SScreening of BMAA-producing cyanobacteria in cultured isolates and in in situ blooms","volume":"29","author":"Monteiro","year":"2017","journal-title":"J. Appl. Phycol."},{"key":"ref_78","first-page":"5","article-title":"Instructions for preparation of modified nutrient solution Z8 for algae","volume":"11","author":"Kotai","year":"1972","journal-title":"Oikos"},{"key":"ref_79","first-page":"448","article-title":"Microbial Production of l-Threonine: Part II. Production by \u03b1-Amino-\u03b2-hydroxyvaleric Acid Resistant Mutants of Glutamate Producing Bacteria","volume":"34","author":"Shiio","year":"1970","journal-title":"Agric. Biol. Chem."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"1763","DOI":"10.1128\/AEM.03729-13","article-title":"Identification and upregulation of biosynthetic genes required for accumulation of mycosporine-2-glycine under salt stress conditions in the halotolerant cyanobacterium Aphanothece halophytica","volume":"80","author":"Kageyama","year":"2014","journal-title":"Appl. Environ. Microbiol."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"963","DOI":"10.1093\/plankt\/fbh083","article-title":"Occurrence of mycosporine-like amino acids (MAAs) in the bloom-forming cyanobacterium Microcystis aeruginosa","volume":"26","author":"Liu","year":"2004","journal-title":"J. Plankton Res."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"101601","DOI":"10.1016\/j.hal.2019.04.004","article-title":"Perspective: Advancing the research agenda for improving understanding of cyanobacteria in a future of global change","volume":"91","author":"Burford","year":"2020","journal-title":"Harmful Algae"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"746","DOI":"10.1016\/j.hal.2008.11.011","article-title":"The strain concept in phytoplankton ecology","volume":"8","author":"Lakeman","year":"2009","journal-title":"Harmful Algae"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/3\/1420\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T18:21:55Z","timestamp":1760120515000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/3\/1420"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,2,2]]},"references-count":83,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2023,2]]}},"alternative-id":["molecules28031420"],"URL":"https:\/\/doi.org\/10.3390\/molecules28031420","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,2,2]]}}}