Glycosylated porphyra-334 and palythine-threonine from the terrestrial cyanobacterium Nostoc commune.
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.
Division of Life Science, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa 920-1192, Japan.
Ehsan
E
Nazifi
Naoki
N
Wada
Minami
M
Yamaba
Tomoya
T
Asano
Takumi
T
Nishiuchi
Seiichi
S
Matsugo
Toshio
T
Sakamoto
D000596:Amino Acids / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology; D000458:Cyanobacteria / Q000737:chemistry; D003511:Cyclohexanols / Q000737:chemistry* / Q000494:pharmacology; D003512:Cyclohexanones / Q000737:chemistry* / Q000494:pharmacology; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D006031:Glycosylation; D050501:Nostoc commune / Q000737:chemistry*; D013473:Sunscreening Agents / Q000737:chemistry / Q000494:pharmacology; D013912:Threonine / Q000737:chemistry* / Q000494:pharmacology; D014466:Ultraviolet Rays; D014867:Water / Q000737:chemistry
D000596:Amino Acids; D000975:Antioxidants; D003511:Cyclohexanols; D003512:Cyclohexanones; D013473:Sunscreening Agents; C523105:palythine; C421025:porphyra-334; D014867:Water; D013912:Threonine; D005998:Glycine