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Mar. Drugs 2013, 11(9), 3124-3154; doi:10.3390/md11093124
Article

Glycosylated Porphyra-334 and Palythine-Threonine from the Terrestrial Cyanobacterium Nostoc commune

1
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4
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2
 and
1,2,3,*
1 Division of Life Science, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa 920-1192, Japan 2 School of Natural System, College of Science and Engineering, Kanazawa University, Kakuma, Kanazawa 920-1192, Japan 3 Division of Biological Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa 920-1192, Japan 4 Division of Functional Genomics, Advanced Science Research Center, Kanazawa University, Takara, Kanazawa 920-0934, Japan
* Author to whom correspondence should be addressed.
Received: 20 June 2013 / Revised: 19 July 2013 / Accepted: 29 July 2013 / Published: 26 August 2013
(This article belongs to the Special Issue Compounds from Cyanobacteria)
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Abstract

Mycosporine-like amino acids (MAAs) are water-soluble UV-absorbing pigments, and structurally different MAAs have been identified in eukaryotic algae and cyanobacteria. In this study novel glycosylated MAAs were found in the terrestrial cyanobacterium Nostoc commune (N. commune). An MAA with an absorption maximum at 334 nm was identified as a hexose-bound porphyra-334 derivative with a molecular mass of 508 Da. Another MAA with an absorption maximum at 322 nm was identified as a two hexose-bound palythine-threonine derivative with a molecular mass of 612 Da. These purified MAAs have radical scavenging activities in vitro, which suggests multifunctional roles as sunscreens and antioxidants. The 612-Da MAA accounted for approximately 60% of the total MAAs and contributed approximately 20% of the total radical scavenging activities in a water extract, indicating that it is the major water-soluble UV-protectant and radical scavenger component. The hexose-bound porphyra-334 derivative and the glycosylated palythine-threonine derivatives were found in a specific genotype of N. commune, suggesting that glycosylated MAA patterns could be a chemotaxonomic marker for the characterization of the morphologically indistinguishable N. commune. The glycosylation of porphyra-334 and palythine-threonine in N. commune suggests a unique adaptation for terrestrial environments that are drastically fluctuating in comparison to stable aquatic environments.
Keywords: anhydrobiosis; antioxidant; mycosporine-like amino acid (MAA); Nostoc commune; UV protectant anhydrobiosis; antioxidant; mycosporine-like amino acid (MAA); Nostoc commune; UV protectant
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Nazifi, E.; Wada, N.; Yamaba, M.; Asano, T.; Nishiuchi, T.; Matsugo, S.; Sakamoto, T. Glycosylated Porphyra-334 and Palythine-Threonine from the Terrestrial Cyanobacterium Nostoc commune. Mar. Drugs 2013, 11, 3124-3154.

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