Isolation and Structure Elucidation of Novel Mycosporine-like Amino Acids from the Two Intertidal Red Macroalgae and

Overview

Journal Mar Drugs

Publisher MDPI

Specialties Biology
Pharmacology

Date 2023 Oct 27

PMID 37888478

Authors

Maria Orfanoudaki

Mostafa Alilou

Anja Hartmann

Julia Mayr

Ulf Karsten

Hieu Nguyen-Ngoc

Markus Ganzera

Affiliations

Soon will be listed here.

Abstract

This study presents a phytochemical survey of two common intertidal red algal species, and , regarding their MAA (mycosporine-like amino acid) composition, which are known as biogenic sunscreen compounds. Six novel MAAs from named bostrychines and two novel MAAs from named catenellines were isolated using a protocol which included silica gel column chromatography, flash chromatography on reversed phase material and semipreparative HPLC (High-Performance Liquid Chromatography). The structure of the novel MAAs was elucidated using NMR (Nuclear Magnetic Resonance) and HR-MS (High-Resolution Mass Spectrometry), and their absolute configuration was confirmed by ECD (Electronic Circular Dichroism). All isolated MAAs possess a cyclohexenimine scaffold, and the metabolites from . are related to the known MAAs bostrychines A-F, which contain glutamine, glutamic acid and/or threonine in their side chains. The new MAAs from . contain taurine, an amino sulfonic acid that is also present in another MAA isolated from this species, namely, catenelline. Previous and new data confirm that intertidal red algae are chemically rich in MAAs, which explains their high tolerance against biologically harmful ultraviolet radiation.

References

DOrazio J, Jarrett S, Amaro-Ortiz A, Scott T . UV radiation and the skin. Int J Mol Sci. 2013; 14(6):12222-48. PMC: 3709783. DOI: 10.3390/ijms140612222. View

Umar S, Tasduq S . Ozone Layer Depletion and Emerging Public Health Concerns - An Update on Epidemiological Perspective of the Ambivalent Effects of Ultraviolet Radiation Exposure. Front Oncol. 2022; 12:866733. PMC: 8960955. DOI: 10.3389/fonc.2022.866733. View

Hartmann A, Becker K, Karsten U, Remias D, Ganzera M . 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. Mar Drugs. 2015; 13(10):6291-305. PMC: 4626690. DOI: 10.3390/md13106291. View

Griffin G, Booth C, Togami K, Chung S, Ssozi D, Verga J . Ultraviolet radiation shapes dendritic cell leukaemia transformation in the skin. Nature. 2023; 618(7966):834-841. PMC: 10284703. DOI: 10.1038/s41586-023-06156-8. View

Geraldes V, Pinto E . Mycosporine-Like Amino Acids (MAAs): Biology, Chemistry and Identification Features. Pharmaceuticals (Basel). 2021; 14(1). PMC: 7828830. DOI: 10.3390/ph14010063. View

Zaytseva A, Chekanov K, Zaytsev P, Bakhareva D, Gorelova O, Kochkin D . Sunscreen Effect Exerted by Secondary Carotenoids and Mycosporine-like Amino Acids in the Aeroterrestrial Chlorophyte under High Light and UV-A Irradiation. Plants (Basel). 2021; 10(12). PMC: 8704241. DOI: 10.3390/plants10122601. View

Chrapusta E, Kaminski A, Duchnik K, Bober B, Adamski M, Bialczyk J . Mycosporine-Like Amino Acids: Potential Health and Beauty Ingredients. Mar Drugs. 2017; 15(10). PMC: 5666432. DOI: 10.3390/md15100326. View

Singh A, cizkova M, Bisova K, Vitova M . Exploring Mycosporine-Like Amino Acids (MAAs) as Safe and Natural Protective Agents against UV-Induced Skin Damage. Antioxidants (Basel). 2021; 10(5). PMC: 8145676. DOI: 10.3390/antiox10050683. View

Hu C, Voller G, Sussmuth R, Dittmann E, Kehr J . Functional assessment of mycosporine-like amino acids in Microcystis aeruginosa strain PCC 7806. Environ Microbiol. 2014; 17(5):1548-59. DOI: 10.1111/1462-2920.12577. View

10.

Orfanoudaki M, Hartmann A, Miladinovic H, Nguyen Ngoc H, Karsten U, Ganzera M . Bostrychines A-F, Six Novel Mycosporine-Like Amino-Acids and a Novel Betaine from the Red Alga . Mar Drugs. 2019; 17(6). PMC: 6627687. DOI: 10.3390/md17060356. View

11.

Raj S, Kuniyil A, Sreenikethanam A, Gugulothu P, Jeyakumar R, Bajhaiya A . Microalgae as a Source of Mycosporine-like Amino Acids (MAAs); Advances and Future Prospects. Int J Environ Res Public Health. 2021; 18(23). PMC: 8656575. DOI: 10.3390/ijerph182312402. View

12.

Nazifi E, Wada N, Asano T, Nishiuchi T, Iwamuro Y, Chinaka S . Characterization of the chemical diversity of glycosylated mycosporine-like amino acids in the terrestrial cyanobacterium Nostoc commune. J Photochem Photobiol B. 2014; 142:154-68. DOI: 10.1016/j.jphotobiol.2014.12.008. View

13.

Oren A, Gunde-Cimerman N . Mycosporines and mycosporine-like amino acids: UV protectants or multipurpose secondary metabolites?. FEMS Microbiol Lett. 2007; 269(1):1-10. DOI: 10.1111/j.1574-6968.2007.00650.x. View

14.

Carreto J, Carignan M . Mycosporine-like amino acids: relevant secondary metabolites. Chemical and ecological aspects. Mar Drugs. 2011; 9(3):387-446. PMC: 3083659. DOI: 10.3390/md9030387. View

15.

Lawrence K, Long P, Young A . Mycosporine-Like Amino Acids for Skin Photoprotection. Curr Med Chem. 2017; 25(40):5512-5527. PMC: 6446518. DOI: 10.2174/0929867324666170529124237. View

16.

Wada N, Sakamoto T, Matsugo S . Mycosporine-Like Amino Acids and Their Derivatives as Natural Antioxidants. Antioxidants (Basel). 2016; 4(3):603-46. PMC: 4665425. DOI: 10.3390/antiox4030603. View

17.

Lalegerie F, Lajili S, Bedoux G, Taupin L, Stiger-Pouvreau V, Connan S . Photo-protective compounds in red macroalgae from Brittany: Considerable diversity in mycosporine-like amino acids (MAAs). Mar Environ Res. 2019; 147:37-48. DOI: 10.1016/j.marenvres.2019.04.001. View

18.

Dextro R, Delbaje E, Geraldes V, Pinto E, Long P, Fiore M . Exploring the Relationship between Biosynthetic Gene Clusters and Constitutive Production of Mycosporine-like Amino Acids in Brazilian Cyanobacteria. Molecules. 2023; 28(3). PMC: 9918943. DOI: 10.3390/molecules28031420. View

19.

Bhatia S, Garg A, Sharma K, Kumar S, Sharma A, Purohit A . Mycosporine and mycosporine-like amino acids: A paramount tool against ultra violet irradiation. Pharmacogn Rev. 2012; 5(10):138-46. PMC: 3263047. DOI: 10.4103/0973-7847.91107. View

20.

Downie A, Wu N, Cramp R, Franklin C . Sublethal consequences of ultraviolet radiation exposure on vertebrates: Synthesis through meta-analysis. Glob Chang Biol. 2023; 29(23):6620-6634. DOI: 10.1111/gcb.16848. View