UV-protective secondary metabolites from cyanobacteria

Martins, Teresa P.; Arsin, Sila; Fewer, David P.; Leão, Pedro N.

doi:10.1016/b978-0-12-821491-6.00005-3

Cited by 4 publications

(8 citation statements)

References 179 publications

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“…Many organisms produce protective pigments and other secondary metabolites to protect themselves against the harmful effects of the ultraviolet radiation . Mycosporine-like amino acids (MAAs) are small, colorless, and water-soluble compounds that effectively absorb UV radiation between 310 and 360 nm with high molar extinction coefficients ranging between ε = 28,100 to 50,000 M cm –1 . − MAAs can dissipate 98% of the absorbed UV radiation as heat to the surroundings, and some variants such as mycosporine-2-glycine and glycosylated pophyra-334 derivatives possess considerable antioxidant activity. − There is over three decades of interest in the potential application of MAAs in the pharmacological and cosmetic industries due to their effective UV absorbance, antioxidant activity and nontoxic nature. − …”

Section: Introductionmentioning

confidence: 99%

“…MAAs are secondary metabolites with over 70 chemical variants that consist of at least one cyclohexanone or cyclohexenimine chromophore where different amino acid substituents can be found bound to the first (C1) and the third (C3) carbon of the chromophore . Modification of the amino acid residues and/or the addition of sugar moieties further increase the structural diversity of MAAs . Shinorine (λ max = 333 nm, 333 Da) and porphyra-334 (λ max = 334 nm, 347 Da) are the most common MAA chemical variants reported. , Shinorine and porphyra-334 biosynthesis proceeds through the action of four enzymes encoded in a compact biosynthetic gene cluster as either mysABCD or mysABCE .…”

Section: Introductionmentioning

confidence: 99%

“…MAAs are secondary metabolites with over 70 chemical variants that consist of at least one cyclohexanone or cyclohexenimine chromophore where different amino acid substituents can be found bound to the first (C1) and the third (C3) carbon of the chromophore. 4 Modification of the amino acid residues and/or the addition of sugar moieties further increase the structural diversity of MAAs. 4 Shinorine (λ max = 333 nm, 333 Da) and porphyra-334 (λ max = 334 nm, 347 Da) are the most common MAA chemical variants reported.…”

Section: Introductionmentioning

confidence: 99%

“… 4 Modification of the amino acid residues and/or the addition of sugar moieties further increase the structural diversity of MAAs. 4 Shinorine (λ max = 333 nm, 333 Da) and porphyra-334 (λ max = 334 nm, 347 Da) are the most common MAA chemical variants reported. 12 , 13 Shinorine and porphyra-334 biosynthesis proceeds through the action of four enzymes encoded in a compact biosynthetic gene cluster as either mysABCD or mysABCE .…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

A Plastic Biosynthetic Pathway for the Production of Structurally Distinct Microbial Sunscreens

Arsın,

Delbaje,

Jokela

et al. 2023

ACS Chem. Biol.

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Mycosporine-like amino acids (MAAs) are small, colorless, and water-soluble secondary metabolites. They have high molar extinction coefficients and a unique UV radiation absorption mechanism that make them effective sunscreens. Here we report the discovery of two structurally distinct MAAs from the lichen symbiont strain Nostoc sp. UHCC 0926. We identified these MAAs as aplysiapalythine E (C 23 H 38 N 2 O 15 ) and tricore B (C 34 H 53 N 4 O 15 ) using a combination of high-resolution liquid chromatography− mass spectrometry (HR-LCMS) analysis and nuclear magnetic resonance (NMR) spectroscopy. We obtained a 8.3 Mb complete genome sequence of Nostoc sp. UHCC 0926 to gain insights into the genetic basis for the biosynthesis of these two structural distinct MAAs. We identified MAA biosynthetic genes encoded in three separate locations of the genome. The organization of biosynthetic enzymes in Nostoc sp. UHCC 0926 necessitates a branched biosynthetic pathway to produce two structurally distinct MAAs. We detected the presence of such discontiguous MAA biosynthetic gene clusters in 12% of the publicly available complete cyanobacterial genomes. Bioinformatic analysis of public MAA biosynthetic gene clusters suggests that they are subject to rapid evolutionary processes resulting in highly plastic biosynthetic pathways that are responsible for the chemical diversity in this family of microbial sunscreens.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…MAAs are secondary metabolites with over 70 chemical variants that consist of at least one cyclohexanone or cyclohexenimine chromophore where different amino acid substituents can be found bound to the first (C1) and the third (C3) carbon of the chromophore. 4 Modification of the amino acid residues and/or the addition of sugar moieties further increase the structural diversity of MAAs. 4 Shinorine (λ max = 333 nm, 333 Da) and porphyra-334 (λ max = 334 nm, 347 Da) are the most common MAA chemical variants reported.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

A Plastic Biosynthetic Pathway for the Production of Structurally Distinct Microbial Sunscreens

Arsın,

Delbaje,

Jokela

et al. 2023

ACS Chem. Biol.

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show abstract

“…Apesar de corresponder a apenas 5% de toda a radiação terrestre, a radiação UV interage fortemente com moléculas orgânicas e é importante para muitos processos biológicos (como por exemplo a produção de vitamina D). No entanto, também pode ser extremamente prejudicial para os organismos vivos, desde animais e plantas até microrganismos (Martins, et al, 2022).…”

Section: Cianobactérias Como Fonte Alternativa De Compostos Fotoprote...unclassified

Caracterização e bioprospecção da biomassa de cianobactérias e microalgas presentes em reservatórios de água visando seu potencial biotecnológico

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Em primeiro lugar, gostaria de agradecer as pessoas sem as quais nada disso seria possível: minha mãe e meu irmão. Mãe, muito obrigada por todo apoio e carinho, não só neste período, mas durante toda a vida. Você é e sempre será meu exemplo! Gui, sem você todas as aventuras teriam gosto de medo, e não teriam nem um terço da graça que tiveram. Amo vocês! Também quero estender esse agradecimento a minha linda família: Edinho, Rose, Camila, Alexia e Pedro. Saber que vocês estavam sempre a caminho, seja lá para onde for, fez essa jornada muito mais leve.Quero agradecer também ao Paulo, por ser um incrível companheiro de muitas aventuras e por ter deixado a cidade cinza mais colorida.Aos meus grandes amigos, Andressa, Carol e Marcelo, muito obrigada! Pela companhia, pelas risadas, ombros e cervejas.Não posso deixar de agradecer também a quem participou de toda essa jornada acadêmica comigo. Ao professor Ernani, muito obrigada por ter aberto as portas do doutorado para mim e por todos os ensinamentos durante essa jornada. À professora Camila, que tão gentilmente aceitou me coorientar, me acolheu em seu laboratório e me ensinou tantas coisas, no pessoal e no profissional. Muito obrigada por toda a dedicação e carinho que vi durante esses anos, não só comigo, mas com toda a equipe de trabalho. Você é um exemplo da profissional que quero me tornar.Ao pessoal do LTPNA, Fernanda, Larissa, Mariana, Rafa, Vanessa e, em especial, a Éryka (amiga linda e companheira oficial de revisões e mochilões) e ao Felipe. O apoio de vocês foi essencial. O meu muito obrigada também a todo o pessoal do meu querido LabAzul,

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A refactored biosynthetic pathway for the production of glycosylated microbial sunscreens

Arsın,

Pollari,

Delbaje

et al. 2024

RSC Chem. Biol.

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UV-protective secondary metabolites from cyanobacteria

Cited by 4 publications

References 179 publications

A Plastic Biosynthetic Pathway for the Production of Structurally Distinct Microbial Sunscreens

A Plastic Biosynthetic Pathway for the Production of Structurally Distinct Microbial Sunscreens

Caracterização e bioprospecção da biomassa de cianobactérias e microalgas presentes em reservatórios de água visando seu potencial biotecnológico

A refactored biosynthetic pathway for the production of glycosylated microbial sunscreens

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