Cerebroside D

Cerebroside D

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Cerebroside D
Category Antibiotics
Catalog number BBF-00765
CAS 113773-89-0
Molecular Weight 756.117
Molecular Formula C43H81NO9
Purity 96.5%

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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. Cerebroside D is a glycoceramide compound with antitumor activity. Study on murine experimental colitis showed that cerebroside D reduced weight loss and the macroscopic as well as microscopic appearances of colitis induced by dexran sulfate sodium. Cerebroside D also inhibited proliferation and induced apoptosis of T cells activated by concanavalin A or anti-CD3 plus anti-CD28 antibodies.


Synonyms (2S,2'R,3R,4E,8E)-N-2'-hydroxyoctadecanoyl-1-O-(β-D-glucopyranosyl)-9-methyl-4,8-sphingadienine; (R)-2-Hydroxy-octadecanoic acid [(3E,7E)-(1S,2R)-2-hydroxy-8-methyl-1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadeca-3,7-dienyl]-amide
IUPAC Name 2-hydroxy-N-[(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]octadecanamide
InChI InChI=1S/C43H81NO9/c1-4-6-8-10-12-13-14-15-16-17-18-20-22-26-31-37(47)42(51)44-35(33-52-43-41(50)40(49)39(48)38(32-45)53-43)36(46)30-27-23-25-29-34(3)28-24-21-19-11-9-7-5-2/h27,29-30,35-41,43,45-50H,4-26,28,31-33H2,1-3H3,(H,44,51)/b30-27+,34-29+/t35?,36?,37?,38-,39-,40+,41-,43-/m1/s1


Appearance Powder
Antibiotic Activity Spectrum fungi
Melting Point 178-189 °C
Solubility Soluble in Methanol

Reference Reading

1. Cerebroside D, a glycoceramide compound, improves experimental colitis in mice with multiple targets against activated T lymphocytes
Xue-Feng Wu, Xing-Xin Wu, Wen-Jie Guo, Qiong Luo, Yan-Hong Gu, Yan Shen, Ren-Xiang Tan, Yang Sun, Qiang Xu Toxicol Appl Pharmacol. 2012 Sep 15;263(3):296-302. doi: 10.1016/j.taap.2012.07.001. Epub 2012 Jul 10.
In the present paper, we aimed to examine the novel effects of cerebroside D, a glycoceramide compound, on murine experimental colitis. Cerebroside D significantly reduced the weight loss, mortality rate and alleviated the macroscopic and microscopic appearances of colitis induced by dexran sulfate sodium. This compound also decreased the levels of TNF-α, IFN-γ and IL-1β in intestinal tissue of mice with experimental colitis in a concentration-dependent manner, accompanied with markedly increased serum level of IL-10. Cerebroside D inhibited proliferation and induced apoptosis of T cells activated by concanavalin A or anti-CD3 plus anti-CD28 antibodies. The compound did not show an effect on naive lymphocytes but prevented cells from entering S phase and G2/M phase during T cells activation. Moreover, the treatment of cerebroside D led to apoptosis of activated T cells with the cleavage of caspase 3, 9, 12 and PARP. These results showed multiple effects of cerebroside D against activated T cells for a novel approach to treatment of colonic inflammation.
2. [The study of the secondary metabolites from fungus Paecilomyces sp]
Yong-Gang Zhang, Wen-Peng Yuan, Xue-Kui Xia, Ai-Rong Jia, Xin Liu, Mian-Song Zhang, Chang-Heng Liu Zhong Yao Cai. 2011 May;34(5):707-9.
Objective: To get active secondary metabolites from the fungus Paecilomyces sp.. Methods: The strain Paecilomyces sp. was further grown in solid-substrate fermentation cultures, the metabolites were got by application of different separation techniques, such as silica gel, Sephadex LH-20 column chromatography, and reversed-phase high performance liquid chromatography. Their structures were identified by comprehensive spectroscopic methods. Results: Four compounds were isolated and identified as Cerebroside C (1), Cerebroside D (2), 2-Hydroxybenzyl alcohol (3), 2-(4-Hydroxyphenyl) ethanol. Conclusion: Four compounds are isolated from Paecilomyces sp. for the first time.
3. Renoprotective chemical constituents from an edible mushroom, Pleurotus cornucopiae in cisplatin-induced nephrotoxicity
Seoung Rak Lee, Dahae Lee, Hae-Jeung Lee, Hyung Jun Noh, Kiwon Jung, Ki Sung Kang, Ki Hyun Kim 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. The protective effects of compounds 2, 5, 6, and 12 were mediated via the deactivation of JNK-caspase 3 apoptotic cascade. This study is the first to demonstrate that the chemical constituents of P. cornucopiae display renoprotective effects against anticancer drug-induced damage in kidney cells.

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