Novel glycosylated mycosporine-like amino acids with radical scavenging activity from the cyanobacterium Nostoc commune

Matsui, Kei; Nazifi, Ehsan; Kunita, Shinpei; Wada, Naoki; Matsugo, Seiichi; Sakamoto, Toshio

doi:10.1016/j.jphotobiol.2011.07.003

Cited by 88 publications

(125 citation statements)

References 61 publications

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“…N. commune has two types of UV-absorbing pigments which are scytonemin and mycosporine-like amino acids (MAAs) [14,16]. Both sunscreen pigments display radical scavenging activities [17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Characterization of the chemical diversity of glycosylated mycosporine-like amino acids in the terrestrial cyanobacterium Nostoc commune

Nazifi

Wada

Asano

et al. 2015

Journal of Photochemistry and Photobiology B: Biology

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Highlights: Glycosylated MAAs have been characterized in two genotypes of Nostoc commune. The A genotype produces β-Ara-porphyra-334 (478 Da) with λ max at 335 nm. The B genotype produces the hybrid MAA (1050 Da) with λ max at 312 nm. 2 AbstractMycosporine-like amino acids (MAAs) are UV-absorbing pigments, and structurally unique glycosylated MAAs are found in the terrestrial cyanobacterium Nostoc commune. In this study, we examined two genotypes of Nostoc commune colonies with different water extract UV-absorption spectra. We found structurally distinct MAAs in each genotype. The water extract from genotype A showed a UV-absorbing spectrum with an absorption maximum at

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Section: Introductionmentioning

confidence: 99%

Characterization of the chemical diversity of glycosylated mycosporine-like amino acids in the terrestrial cyanobacterium Nostoc commune

Nazifi

Wada

Asano

et al. 2015

Journal of Photochemistry and Photobiology B: Biology

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“…They are characterized by a unique strong peak in the wavelength range of 310-365 nm (ε = 28 000-50 000 M −1 · cm −1 ). About 40 mycosporines and derivatives have been described so far, and some of them are substituted with functional groups or are covalently bound to saccharidic units [5][6][7][8]. Such UV-absorbing compounds are distributed in taxonomically diverse organisms of terrestrial, marine, or freshwater origin [9].…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, we investigated some biological activities related to UV filter requirements including the ethyl derivative 3, which exhibited a higher molar extinction coefficient 21 295 M − 1 .cm −1 . Until now, most mycosporine-like compounds tested for their antioxidant activities are either pure imino-mycosporines or a mixture of several imino-mycosporines [7,[22][23][24][25][26]. Thus, oxo-mycosporines are less reported, and only mycosporine glycine and mycosporine glutaminol glucoside have been tested so far [23,[27][28][29].…”

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confidence: 99%

Mycosporine-Like Compounds in Chlorolichens: Isolation from Dermatocarpon luridum and Dermatocarpon miniatum, and their Photoprotective Properties

et al. 2015

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!Two mycosporines were isolated for the first time in two chlorolichen species, Dermatocarpon luridum and Dermatocarpon miniatum. Mycosporine glutaminol (1) and mycosporine glutamicol (2) were isolated along with the ethyl ester of mycosporine glutamicol (3), which was formed during the purification process. Aqueous extracts and pure mycosporines were then investigated for their antioxidant activities and photoprotective properties along with their photostability and photocytotoxicity. Semi-purified mycosporine fractions were much more antioxidant than lichen aqueous crude extracts. Compound 3 (IC 50 = 4.00 µg/mL) was found to be as active as quercetin (IC 50 = 6.75 µg/mL), while the two genuine mycosporines 1 and 2 exhibited moderate activity. The three mycosporines were found to be stable until 5J/ m 2 UVA and UVB radiations whereas Trolox, used as a positive control, was degraded up to 10% and 19 %, respectively. Moreover, these mycosporines and semi-purified extracts did not induce any phototoxicity on HaCaT cells exposed to UVA radiations. Key wordsDermatocarpon luridum · Dermatocarpon miniatum · Verrucariaceae · lichen · mycosporine-like amino acids (MAAs) · photoprotectioncrude aqueous extract of D. luridum DL2:semi-purified aqueous extract of D. luridum DM1:crude aqueous extract D. miniatum DM2:semi-purified aqueous extract of D. miniatum MAAs:mycosporine-like amino acids PDA:photodiode array PIF:photo-irritancy factors Supporting information available online at http://www.thieme-connect.de/productsMycosporine-like compounds comprising mycosporines and MAAs have received much attention for their putative role in UV photoprotection as antioxidants and osmoprotectants [1][2][3][4]. Mycosporine-like compounds are small water-soluble molecules composed of cyclohexenone (oxo-mycosporine) or cyclohexenimine (imino-mycosporine) ring structures conjugated to an amino acid or an amino alcohol subunit. They are characterized by a unique strong peak in the wavelength range of 310-365 nm (ε = 28 000-50 000 M −1 · cm −1 ). About 40 mycosporines and derivatives have been described so far, and some of them are substituted with functional groups or are covalently bound to saccharidic units [5][6][7][8]. Such UV-absorbing compounds are distributed in taxonomically diverse organisms of terrestrial, marine, or freshwater origin [9]. More recently, the distribution of mycosporinelike compounds has been reported in cyanolichens (symbiotic organisms resulting from an association between a fungus and a cyanobacterium) [10,11]. Although chlorolichens correspond to 90 % of lichen species, mycosporine-like compounds have not yet been described in chlorolichens in which cyanobacteria are replaced by green algae. Their secondary metabolite profile is generally characterized by a variety of specific phenolic compounds, and most of them have UV absorbing properties [2,12]. A previous phytochemical screening revealed that chlorolichens belonging to the Dermatocarpon genus (Verrucariaceae) did not contain the usual lichen subs...

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“…Different kinds of MAAs have been found in cyanobacterial species in a variety of habitats such as the marine environment (Liu et al, 2004), hypersaline ponds (Kedar et al, 2002), rice fields (Sinha et al, 2003) and deserts (Bowker et al, 2002), and further investigations in diverse habitats might reveal new MAAs. Recently, glycosylated MAAs have been isolated from the terrestrial cyanobacterium Nostoc commune (Matsui et al, 2011;Nazifi et al, 2013Nazifi et al, , 2015. One of these MAAs (absorption maximum 334 nm) was identified as a hexose-bound porphyra-334 derivative with a molecular mass of 508 Da, another (absorption maximum 322 nm) as a two hexose-bound palythinethreonine derivative with a molecular mass of 612 Da.…”

Section: Mycosporine-like Amino Acids (Maas)mentioning

confidence: 99%

Cyanobacterial metabolites as a source of sunscreens and moisturizers: a comparison with current synthetic compounds

Derikvand

Llewellyn

Purton

2016

European Journal of Phycology

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Novel glycosylated mycosporine-like amino acids with radical scavenging activity from the cyanobacterium Nostoc commune

Cited by 88 publications

References 61 publications

Characterization of the chemical diversity of glycosylated mycosporine-like amino acids in the terrestrial cyanobacterium Nostoc commune

Characterization of the chemical diversity of glycosylated mycosporine-like amino acids in the terrestrial cyanobacterium Nostoc commune

Mycosporine-Like Compounds in Chlorolichens: Isolation from Dermatocarpon luridum and Dermatocarpon miniatum, and their Photoprotective Properties

Cyanobacterial metabolites as a source of sunscreens and moisturizers: a comparison with current synthetic compounds

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