Characterization and identification of mycosporines-like compounds in cyanolichens. Isolation of mycosporine hydroxyglutamicol from Nephroma laevigatum Ach.

Roullier, Catherine; Chollet-Krugler, Marylène; Pferschy‐Wenzig, Eva‐Maria; Maillard, Anne; Rechberger, Gerald; Legouin-Gargadennec, Béatrice; Bauer, Rudolf; Boustié, Joël

doi:10.1016/j.phytochem.2011.04.002

Cited by 34 publications

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“…As lichens are symbiotic organisms, involvement of their respective partners in the biogenesis of mycosporines should be elucidated. Until now, cyanobacteria were supposed to produce mycosporinelike compounds in cyanolichens [10]. Thus far, mycosporines 1 and 2 and their glycolysed derivates have been described in various terrestrial ascomycetous fungi [18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

“…[6] and compound 2 in the cyanolichen Degelia plumbea [10]. As no green algae are described to date to synthesize these mycosporines, the fungal partner may also be involved in the biosynthesis of mycosporines 1 and 2, especially since mycosporine described in lichens have the characteristic carbonyl moiety of fungal mycosporines.…”

Section: Introductionmentioning

confidence: 99%

“…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.…”

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confidence: 99%

“…Thus far, mycosporines 1 and 2 and their glycolysed derivates have been described in various terrestrial ascomycetous fungi [18][19][20][21]. In addition, compound 1 has also been detected in the terrestrial cyanobacteria Leptolyngbya sp.[6] and compound 2 in the cyanolichen Degelia plumbea [10]. As no green algae are described to date to synthesize these mycosporines, the fungal partner may also be involved in the biosynthesis of mycosporines 1 and 2, especially since mycosporine described in lichens have the characteristic carbonyl moiety of fungal mycosporines.…”

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confidence: 99%

“…The aqueous extracts and purified mycosporines were tested for their antioxidant activities, photostability, and photocytotoxicity. To investigate D. luridum and D. miniatum for mycosporine-like compounds, a protocol previously described [10] was used to extract lichen material with water (+ 4°C) followed by semi-purification on cation exchange resin chromatography (see Supporting Information). The HPLC-DAD-MS 2 analysis of DL2 and DM2 revealed the presence of three mycosporines, 1, 2, and 3, with an absorption maximum at 310 nm (l " Table 1).…”

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confidence: 99%

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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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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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

et al. 2015

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Mycosporine‐Like Amino Acids (MAAs) in Biological Photosystems

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Roullier

Boustié

2014

Outstanding Marine Molecules

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Analysis of the cyanolichenLichina pygmaeametabolites usingin situDART-MS: from detection to thermochemistry of mycosporine serinol

et al. 2015

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Direct Analysis in Real Time DART-HRMS is here first applied to the detection of molecules from a lichen, Lichina pygmaea. The aim was to propose an innovative method of in situ detection of lichen secondary metabolites using the possibilities of elemental composition determination available when a DART source is interfaced with a TOF analyzer. Three kinds of samples have been submitted to DART ionization, i.e. an intact thallus, a powder obtained from the crushed lichen and an aqueous extract. In situ analysis of crushed lichen, yields an extensive chemical profile, comparable to what is obtained from the aqueous extract, comprising both major polar metabolites described in literature along with some other signals that could correspond to potentially unknown metabolites. One of the detected secondary metabolites, mycosporine serinol, underwent a dehydration reaction prior to its transfer in the gas-phase by DART ionization. The consideration of the thermal transfers involved in the DART ionization process and the possibility to record time-dependent mass spectra through the use of the TOF analyzer allowed establishing Arrhenius plots of this water molecule loss to obtain associated thermodynamic quantities. The low values of corresponding activation enthalpy (Δr‡Hm° of the order of 25 kJ mol(-1)) enabled formulating some assumption regarding a possible role of such metabolites in the lichen.

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Characterization and identification of mycosporines-like compounds in cyanolichens. Isolation of mycosporine hydroxyglutamicol from Nephroma laevigatum Ach.

Cited by 34 publications

References 18 publications

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

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

Mycosporine‐Like Amino Acids (MAAs) in Biological Photosystems

Analysis of the cyanolichenLichina pygmaeametabolites usingin situDART-MS: from detection to thermochemistry of mycosporine serinol

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