Found 2 structures.
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1. Compound ID: 18261
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b-D-Glcp-(1-4)-Subst
Subst = glyscavin A aglycon = SMILES O{1}C1=CC={4}C(O)C(/C=C/C=C/C)=C1{7}CO |
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Structure type: monomer
; 391.1369 [M+Na]+
C18H24O8
Trivial name: glyscavin A (4-O-β-D-glucopyranosyl-2-hydroxymethyl-3-penta-1,3-dienyl)phenol)
Compound class: phenolic glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7144
Moon BS, Ryoo IJ, Yun BS, Bae KS, Lee KD, Yoo ID, Kim JP "Glyscavins A, B and C, new phenolic glycoside antioxidants produced by a fungus Mycelia sterilia F020054" -
The Journal of Antibiotics 59(2) (2006) 735-739
Three new phenolic glycosides designated glyscavins A (1), B (2), and C (3) were isolated from the culture broth of a fungal strain Mycelia sterilia F020054. Structural elucidation of the compounds was based on the NMR and MS spectroscopic analyses. Glyscavins A, B and C exhibited higher free radical scavenging activity on superoxide and 2,2'-azinobis(3-ethylbenzothialozinesulfonic acid) cation radical (ABTS*+) than butylated hydroxyanisole (BHA).
Antioxidant, glyscavin, phenolic glycosides, Mycelia sterilia
NCBI PubMed ID: 17256474Publication DOI: 10.1038/ja.2006.99Journal NLM ID: 0151115Publisher: London: Nature Publishing Group
Correspondence: Kim JP
Institutions: Korea Research Institute of Bioscience and Biotechnology (KRIBB), Daejeon, South Korea, Department of Chemistry, Dongguk University, Gyeongbuk, South Korea
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, acid hydrolysis, FTIR, composition analysis, UV, extraction, antioxidant activities, HR-FAB-MS
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2. Compound ID: 20543
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a-D-Manp-(1-2)-+
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{{{-b-D-Manp-(1-2)-}}}/n=13/-b-D-Manp-(1--P--?)--a-D-Manp-(1-2)-a-D-Manp-(1-2)-+
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{{{-b-D-Manp-(1-2)-}}}/n=3/-{{{-a-D-Manp-(1-2)-}}}/n=2/-a-D-Manp-(1-2)-+ |
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{{{-b-D-Manp-(1-2)-}}}/n=2/-{{{-a-D-Manp-(1-2)-}}}/n=2/-a-D-Manp-(1-2)-+ | |
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a-D-Manp-(1-3)-{{{-a-D-Manp-(1-2)-}}}/n=3/-a-D-Manp-(1-2)-+ | | |
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a-D-Manp-(1-2)-a-D-Manp-(1-3)-{{{-a-D-Manp-(1-2)-}}}/n=2/-a-D-Manp-(1-2)-+ | | | |
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b-D-Manp-(1-2)-{{{-a-D-Manp-(1-2)-}}}/n=2/-a-D-Manp-(1-2)-+ | | | | |
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{{{-a-D-Manp-(1-2)-}}}/n=2/-a-D-Manp-(1-2)-+ | | | | | |
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a-D-Manp-(1-2)-a-D-Manp-(1-2)-+ | | | | | | |
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a-D-Manp-(1-2)-+ | | | | | | | |
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{{{-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-+ | | | | | |
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a-D-Manp-(1-3)-{{{-a-D-Manp-(1-2)-}}}/n=2/-a-D-Manp-(1-2)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-}}}Subst-(?-?)-D-GlcpNAc-(1-4)-D-GlcpNAc-(1-?)-Asn-(?--/(->3) L-Ser/L-Thr (protein)/
Subst = inner core |
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Structure type: structural motif or average structure
Aglycon: (->3) L-Ser/L-Thr (protein)
Compound class: mannan, mannoprotein
Contained glycoepitopes: IEDB_128161,IEDB_130701,IEDB_131173,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_134620,IEDB_134621,IEDB_135813,IEDB_136104,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_141111,IEDB_141793,IEDB_141795,IEDB_141807,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141831,IEDB_141832,IEDB_141833,IEDB_141834,IEDB_142357,IEDB_143632,IEDB_144983,IEDB_144994,IEDB_144995,IEDB_151531,IEDB_152206,IEDB_153212,IEDB_153220,IEDB_153756,IEDB_153762,IEDB_153763,IEDB_1539315,IEDB_164174,IEDB_164175,IEDB_164176,IEDB_164177,IEDB_164479,IEDB_164480,IEDB_173895,IEDB_174840,IEDB_474450,IEDB_76920,IEDB_76933,IEDB_857732,IEDB_857735,IEDB_858578,IEDB_983930,SB_136,SB_191,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 8177
Hirata N, Ishibashi K, Sato W, Nagi-Miura N, Adachi Y, Ohta S, Ohno N "β-mannosyl linkages inhibit CAWS arteritis by negatively regulating dectin-2-dependent signaling in spleen and dendritic cells" -
Immunopharmacology and Immunotoxicology 35(5) (2013) 594-604
AIMS: CAWS, Candida albicans water-soluble fraction, is an extracellular mannoprotein produced by C. albicans NBRC1385. It is a ligand of dectin-2, the C-type lectin receptor for innate immunity, and has strong potency for induction of vasculitis in DBA/2 mice. The structure of this mannoprotein is known to be modulated by the culture conditions. To clarify the structure required for vasculitis, CAWSs were prepared in the two culture conditions with or without pH control, and biological properties were compared. METHODS: CAWSs prepared by the standard protocol and pH controlled at 7.0 were designated as CAWS and CAWS727, respectively. The antigenicity was detected by the anti-Candida mannan IgG. These chemical structures were assessed by nuclear magnetic resonance analysis and the lectin array system. The in vitro activity of CAWSs was tested by tumor necrosis factor-α (TNF-α) induction using bone marrow-derived dendritic cells and spleen cell cultures. RESULTS: The antigenicity of CAWS727 was similar to CAWS but the nuclear magnetic resonance analysis showed a higher ratio of β-mannosyl linkages were detected in CAWS727. The lectin array showed relative affinities of CAWS727 to α-mannosyl specific lectins were weaker than those of CAWS. CAWS induced severe vasculitis in DBA/2 mice while CAWS727 did not. CAWS significantly induced TNF-α but CAWS727 did slightly. In addition, CAWS-induced TNF-α production was inhibited by mixing with CAWS727 in a concentration dependent manner. CONCLUSION: The α-mannosyl linkages of Candida mannan is a key molecule for the immunotoxicity. CAWS727, which conatins β-mannosyl linkages, competitively bound to lectin receptors, and resulted in reductions in the inflammatory response.
inflammation, fungal, Candida albicans, β-1, Autoimmunity, DBA/2 mice, mannoprotein, arteritis, 2-mannan
NCBI PubMed ID: 23981001Publication DOI: 10.3109/08923973.2013.830124Journal NLM ID: 8800150Publisher: London: Informa Healthcare
Correspondence: Ohno N
Institutions: Department of Pharmacy, Nagano Red Cross Hospital, Nagano, Japan, Laboratory for Immunopharmacology of Microbial Products, School of Pharmacy, Tokyo, Japan, Department of Pharmaceutical Health Care and Science, Tokyo University of Pharmacy and Life Science, Tokyo, Japan
Methods: 13C NMR, 1H NMR, ELISA, statistical analysis, HSQC
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