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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)

NCBI PubMed ID: 18067882
Publication DOI: 10.1016/j.carres.2007.11.010
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: ruszova

contipro.cz (Ema Ruszova)
Institutions: CPN spol. s.r.o, 561 02 Dolni Dobrouc 401, Czech Republic, Institute of Biophysics Academy of Sciences of the Czech Republic, Kralovopolska 135, 612 65 Brno, Czech Republic

Glucomannans belong to yeast and fungal cell wall polysaccharides with known immunostimulatory and radioprotective effects. However, glucomannan protective effects against pathological consequences of skin exposure to short wavelength solar light, ultraviolet (UV) radiation, are unclear. Herein, a highly branched glucomannan (GM) isolated from the cell wall of Candida utilis, a member of the alpha-(1-->6)-D-mannan group, was tested for its photoprotective effects in an in vitro model of UVB-irradiated human keratinocytes and an in vivo model of UV-induced erythema formation in human volunteers. GM suppressed the UVB-induced decrease of keratinocyte viability, which was connected with the suppression of UVB-induced keratinocyte apoptosis. GM reduced UVB-mediated caspase activation together with suppression of DNA fragment release into the cytoplasm. Furthermore, GM suppressed UVB-induced gene expression of pro-inflammatory markers including nuclear factor kappa B, inducible nitric oxide synthase, interleukins 8 and 1, together with suppression of prostaglandin E2 and interleukin 1alpha protein release. In vivo, GM decreased UV-induced skin erythema formation, which was correlated with a decrease of phosholipase A(2) activity within the stratum corneum. It could be concluded that GM isolated from C. utilis possesses significant photoprotective effects on human keratinocytes in vitro as well as in vivo.

polysaccharide, apoptosis, Glucomannan, Candida utilis, HaCaT keratinocytes, UV-protection

Structure type: structural motif or average structure ; 30000-70000
Location inside paper: p.502, fig.1
Trivial name: glucomannan
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141795,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141831,IEDB_141832,IEDB_141833,IEDB_141834,IEDB_141835,IEDB_141836,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_164480,IEDB_76933,IEDB_857735,IEDB_983930,IEDB_983931,SB_136,SB_191,SB_192,SB_196,SB_198,SB_44,SB_67,SB_72

Methods: DNA techniques, ELISA, genetic methods, extraction, enzymatic analysis, statistical analysis, microarray analysis, measurement of cytokines, UVB irradiation
Biological activity: Glucomannan acts as a photoprotective agent and prevents UVB-induced damage of cutaneous cells.
Comments, role: the leftmost side chains may contain from 1 to 4 mannose residues. The linear mannosyl backbone regions may be shorter (0..2 residues)

NCBI Taxonomy refs (TaxIDs): 4903
Reference(s) to other database(s): GTC:G78291GU
Show glycosyltransferases

There is only one chemically distinct structure:

[*]OC[C@H]1O[C@H](OC[C@H]2O[C@H](OC[C@H]3O[C@H](OC[C@H]4O[C@H](OC[C@H]5O[C@H](OC[C@H]6O[C@H]([*])[C@@H](O)[C@@H](O)[C@@H]6O)[C@@H](O)[C@@H](O)[C@@H]5O)[C@@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]5O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]5O[C@H]5O[C@H](COC6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@@H](O)[C@H](O)[C@@H]5O)[C@@H](O)[C@@H]4O)[C@@H](O)[C@@H](O)[C@@H]3O)[C@@H](O)[C@@H](O)[C@@H]2O)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize

Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Organ / tissue: thallus

The structure was elucidated in this paper
NCBI PubMed ID: 14764094
Publication DOI: 10.1111/j.1432-1033.2004.03981.x
Journal NLM ID: 0107600
Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: Srebnik M <msrebni

md.huji.ac.il>
Institutions: Department of Medicinal Chemistry and Natural Products, School of Pharmacy, Hebrew University of Jerusalem, Jerusalem, Israel, Teva Pharmaceutical Industries Ltd, Petach Tikva, Israel, Division of Environment Science, The Fredy and Nadine Herrmann Graduate School of Applied Sciences, The Hebrew University of Jerusalem, Jerusalem, Israel, Department of Dermatology, Hadassah University Hospital, Jerusalem, Israel, Institute of Ecology, Haifa University, Haifa, Israel

A novel photo protective mycosporine was isolated from the lichenized ascomycete Collema cristatum. Biological activity was measured in terms of protection against UV-B induced membrane destruction and pyrimidine dimer formation in cultured human keratinocytes, and prevention of UV-B induced erythema. It was found that the pure isolated compound prevented UV-B induced cell destruction in a dose-dependent manner, that the compound partially prevented pyrimidine dimer formation and completely prevented UV-B induced erythema when applied to the skin prior to irradiation.

mycosporine, lichenized ascomycete, Collema cristatum, photo protective activity, UV-B

Structure type: monomer ; 497 [M+H]+
C₁₉H₃₂N₂O₁₃
Location inside paper: fig.1
Trivial name: collemin A
Compound class: mycosporine
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, IR, HPLC, UV, extraction, biological assay, HR-FAB-MS, UVB irradiation
Biological activity: the pure compound was applied to the inside forearm of a volunteer 30 min prior to four minimal erythema dose of UV-B irradiation, the isolated compound totally prevented UV-B induced erythema
Comments, role: mycobiont was also isolated from thallus; symbiotic organism

Related record ID(s): 48023
NCBI Taxonomy refs (TaxIDs): 402075
Show glycosyltransferases

There is only one chemically distinct structure:

NC1=C(O)C(=O)C(O[C@H]2N[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2OCCO)C(CO)C1

SVG MW SMILES 3D mol Ionize