Cerebroside B

Cerebroside B

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Cerebroside B
Category Antibiotics
Catalog number BBF-00763
CAS 88642-46-0
Molecular Weight 728.05
Molecular Formula C41H77NO9
Purity >97%

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It is produced by the strain of Pachybasium sp. It has strong anti-candida albicans B311 activity in the presence of aculeacin with 0.05 ㎍/mL.


Synonyms 1-O-beta-d-glucopyranosyl-(2s,3r,4e,8e)-2-[(2r)-2-hydroxyhexadecanoylamino]-9-methyl-4,8-octadecadiene-1,3-diol; 1-O-Pivaloyl-glycerin; 1-pivaloyloxypropane-2,3-diol; Propanoic acid,2,2-dimethyl-,2,3-dihydroxypropyl ester; glucocerebroside
IUPAC Name (2R)-2-hydroxy-N-[(2S,3R,4E,8E)-3-hydroxy-9-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]hexadecanamide
InChI InChI=1S/C41H77NO9/c1-4-6-8-10-12-13-14-15-16-18-20-24-29-35(45)40(49)42-33(31-50-41-39(48)38(47)37(46)36(30-43)51-41)34(44)28-25-21-23-27-32(3)26-22-19-17-11-9-7-5-2/h25,27-28,33-39,41,43-48H,4-24,26,29-31H2,1-3H3,(H,42,49)/b28-25+,32-27+/t33-,34+,35+,36+,37+,38-,39+,41+/m0/s1


Appearance Powder
Antibiotic Activity Spectrum fungi
Melting Point 180-190 °C
Solubility Soluble in Methanol

Reference Reading

1.Identification and Evaluation of Bioactivity of Compounds from the Mushroom Pleurotus nebrodensis (Agaricomycetes) against Breast Cancer.
Hao J;Zhang X;Yu W;Wang R;Xue Z;Kou X Int J Med Mushrooms. 2017;19(9):839-848. doi: 10.1615/IntJMedMushrooms.2017024372.
Breast cancer affects millions of women annually worldwide and is the leading cause of cancer death in women. Various bioactive phytochemicals based on natural products are considered to be an important source of chemopreventive agents. In this study we report-to our knowledge for the first time-9 phytochemicals isolated by nuclear magnetic resonance spectroscopy and mass spectrometry from the acetic ether extract of Pleurotus nebrodensis and identified as (1) ergosterol, (2) uracil, (3) ergosterol-3-O-β-D-glucopyranoside, (4) cerevisterol, (5) cerebroside B, (6) 5'-methylthioadenosine, (7) adenosine, (8) hypoxanthine, and (9) uridine. Their bioactivities were screened with an MTT assay using breast cancer MCF-7 cells in vitro. As a result, about half of the isolated compounds demonstrated moderate or strong inhibitory activity in a concentration-dependent manner. Among them, compound 1 (ergosterol) exhibited superior activity and the lowest half-maximal inhibitory concentration (112.65 μmol/L). Further mechanistic study elucidated that compound 1 led to significant S-phase cell cycle arrest and induced apoptosis in MCF-7 cells. Our study shows the mycochemical composition of the P.
2.Steroids and phenolic constituents from the fruiting bodies of the basidiomycete Sarcodon joedes.
Liu HW;Hu L;Zhang AL;Gao JM Nat Prod Res. 2013;27(1):80-4. doi: 10.1080/14786419.2012.656112. Epub 2012 Feb 9.
Nine secondary metabolites, including four steroids, four phenolics and one cerebroside, were isolated from the methanol extract of the fruiting bodies of the basidiomycete Sarcodon joedes. The isolated compounds were identified by spectroscopic analyses as (22E,24R)-6β-methoxyergosta-7,22-diene-3β,5α-diol (1), 2',3'-diacetoxy-3,4,5',6',4″-pentahydroxy-p-terphenyl (2), cerebroside B (3), ergosta-7,22-dien-3β-ol (4), ergosterol peroxide (5), (22E,24R)-3β-hydroxy-ergosta-5,22-dien-7-one (6), benzoic acid (7), methyl p-hydroxybenzoate (8) and 3,4-dihydroxybenzoic acid (9). The cytotoxic activities of these compounds were evaluated. All these compounds were isolated from this fungus for the first time.
3.Renoprotective chemical constituents from an edible mushroom, Pleurotus cornucopiae in cisplatin-induced nephrotoxicity.
Lee SR;Lee D;Lee HJ;Noh HJ;Jung K;Kang KS;Kim KH Bioorg Chem. 2017 Apr;71:67-73. doi: 10.1016/j.bioorg.2017.01.012. Epub 2017 Jan 19.
Pleurotus cornucopiae (Pleurotaceae) is an edible and medicinal mushroom widely distributed in Korea, China, and Japan. The MeOH extract of the fruiting bodies of P. cornucopiae showed renoprotective effects against cisplatin-induced kidney cell damage. Chemical investigation of the MeOH extract led to the isolation and identification of 12 compounds including noransine (1), uridine (2), uracil (3), (3β, 5α, 6β, 22E, 24S) -ergosta-7, 22-diene-3, 5, 6, 9-tetrol (4), (22E,24S)-ergosta-7,22-diene-3β,5α,6β-triol (5), (22E,24R)-ergosta-8(14),22-diene-3β,5α,6β,7α-tetrol (6), cerebroside B (7), (2R) -N- [(1S, 2R, 3E, 7E) -1- [(β-d-glucopyranosyloxy) methyl] -2-hydroxy-8-methyl-3, 7-heptadecadien-1-yl] -2-hydroxy-heptadecanamide (8), cerebroside D (9), nicotinamide (10), 1,2-bis(hydroxymethyl)-4,5-dimethoxybenzene (11), and benzoic acid (12). Among them, compounds 1 and 11 were isolated as naturally occurring products for the first time, though they were reported as synthetic products in previous papers. All of the compounds (except 8 and 11) abrogated cisplatin-induced LLC-PK1 cell damage in a dose-dependent manner. Of special note, compounds 2, 5, 6, and 12 ameliorated cisplatin-induced nephrotoxicity to 80% of the control value at 10μM.

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