Cerebroside B

Sci Rep. 2015 May 21;5:10486.

Δ10(E)-Sphingolipid Desaturase Involved in Fusaruside Mycosynthesis and Stress Adaptation in Fusarium graminearum.[Pubmed: 25994332]

Sphingolipids are biologically important and structurally distinct cell membrane components. Fusaruside (1) is a 10,11-unsaturated immunosuppressive fungal sphingolipid with medical potentials for treating liver injury and colitis, but its poor natural abundance bottlenecks its druggability.
METHODS AND RESULTS:
Here, fusaruside is clarified biosynthetically, and its efficacy-related 10,11-double bond can be generated under the regioselective catalysis of an unprecedented Δ10(E)-sphingolipid desaturase (Δ10(E)-SD). Δ10(E)-SD shares 17.7% amino acid sequence similarity with a C9-unmethylated Δ10-sphingolipid desaturase derived from a marine diatom, and 55.7% with Δ8(E)-SD from Fusarium graminearum. Heterologous expression of Δ10(E)-SD in Pichia pastoris has been established to facilitate a reliable generation of 1 through the Δ10(E)-SD catalyzed desaturation of Cerebroside B (2), an abundant fungal sphingolipid. Site directed mutageneses show that the conserved histidines of Δ10(E)-SD are essential for the 10,11-desaturation catalysis, which is also preconditioned by the C9-methylation of the substrate. Moreover, Δ10(E)-SD confers improved survival and faster growth to fungal strains at low temperature and high salinity, in parallel with to higher contents of 1 in the mycelia.
CONCLUSIONS:
Collectively, the investigation describes a new Δ10(E)-sphingolipid desaturase with its heterologous expression fundamentalizing a biotechnological supply of 1, and eases the follow-up clarification of the immunosuppression and stress-tolerance mechanism.

Nat Prod Res. 2013;27(1):80-4.

Steroids and phenolic constituents from the fruiting bodies of the basidiomycete Sarcodon joedes.[Pubmed: 22320163]

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.
METHODS AND RESULTS:
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.
CONCLUSIONS:
All these compounds were isolated from this fungus for the first time.

Tetrahedron, 1989, 45(23):7263-80.

Synthesis of cerebroside B1b with antiulcerogenic activity I. Synthesis of ceramides with optically active α-hydroxypalmitic acids.[Reference: WebLink]

METHODS AND RESULTS:
Synthesis of Cerebroside B1b with antiulcerogenic activity I. Synthesis of ceramides with optically active α-hydroxypalmitic acids.