Cerebroside A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00515 |
| CAS | |
| Molecular Weight | 726.03 |
| Molecular Formula | C41H75NO9 |
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Description
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.
Specification
| IUPAC Name | (E)-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]hexadec-3-enamide |
| Canonical SMILES | CCCCCCCCCCCCC=CC(C(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C=CCCC=C(C)CCCCCCCCC)O)O |
| InChI | InChI=1S/C41H75NO9/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/h24-25,27-29,33-39,41,43-48H,4-23,26,30-31H2,1-3H3,(H,42,49)/b28-25+,29-24+,32-27+/t33?,34?,35?,36-,37-,38+,39-,41-/m1/s1 |
| InChI Key | SUBYBSQARMSYNW-MRLDOHMVSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 170-180 °C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Diverse bioactive metabolites from Penicillium sp. MMA derived from the red sea: structure identification and biological activity studies
Ann G Boulis, Ahmed A Hamed, Mohamed E El-Awady, Attia R Mohamed, Essam M Eliwa, Mohsen M S Asker, Mohamed Shaaban Arch Microbiol. 2020 Sep;202(7):1985-1996. doi: 10.1007/s00203-020-01923-x. Epub 2020 May 31.
A soft coral-derived fungus Penicillium sp. among other isolates e high antibacterial, anti-yeast and cytotoxic activities. The fungus, Penicillium sp. MMA, isolated from Sarcphyton glaucoma, afforded nine diverse compounds (1-9). Their structures were identified by 1D and 2 D NMR and ESI-MS spectroscopic data as two alkaloids: veridicatol (1), aurantiomide C (2); one sesquiterpene, aspterric acid (3); two carboxylic acids, 3,4-dihydroxy-benzoic acid; (4) and linoleic acid (5); three steroids, ergosterol (6), β-Sitosterol (7), β-Sitosterol glucoside (8) along with the sphingolipid, cerebroside A (9). Biologically, the antimicrobial, antioxidant, in vitro cytotoxicity and antibiofilm activities were studied in comparison with the fungal extract. The in silico computational studies were implemented to predict drug and lead likeness properties for 1-4. The fungus was taxonomically characterized by morphological and molecular biology (18srRNA) approaches.
2. Penicisteroid C: New polyoxygenated steroid produced by co-culturing of Streptomyces piomogenus with Aspergillus niger
Ahmed S Abdel-Razek, Abdelaaty Hamed, Marcel Frese, Norbert Sewald, Mohamed Shaaban Steroids. 2018 Oct;138:21-25. doi: 10.1016/j.steroids.2018.06.005. Epub 2018 Jun 15.
Penicisteroid C, a new polyoxygenated steroid was isolated from co-cultivation of Streptomyces piomogenus AS63D and Aspergillus niger using solid-state fermentation on rice medium. Additional diverse eleven known metabolites were identified: Fumigaclavine C, fumiquinazoline C, physcion, methylsulochrin, methyllinoleate, glycerol linoleate, cerebroside A, thymine, adenine, thymidine and adenosine. The structure of penicisteroid C was determined by HRESIMS, 1D and 2D NMR data. The antimicrobial and in vitro cytotoxic activities of the microbial extract and penicisteroid C were reported as well.
3. Meleagrin from marine fungus Emericella dentata Nq45: crystal structure and diverse biological activity studies
Abdelaaty Hamed, Ahmed S Abdel-Razek, Mariam Araby, Mohammed Abu-Elghait, Doaa G El-Hosari, Marcel Frese, Hesham S M Soliman, Hans Georg Stammler, Norbert Sewald, Mohamed Shaaban Nat Prod Res. 2021 Nov;35(21):3830-3838. doi: 10.1080/14786419.2020.1741583. Epub 2020 Mar 19.
The crystal structure and unambiguous absolute configuration of meleagrin (1) isolated from fungus Emericella dentata Nq45 is reported herein to first time on the bases of single crystal X-ray diffraction. Together with 1, haenamindole (2), isorugulosuvine (3), secalonic acid D (4), ergosterol (5) and cerebroside A (6) were obtained and their structures were determined by ESI MS and NMR data analysis. Diverse biological activity of meleagrin (1) was investigated. Compound 1 pronounced potent cytotoxicity against the human cervix carcinoma cell line KB-3-1 and its multidrug resistant sub-clone KB-V1 of IC50 3.07 and 6.07 µM, respectively, in comparison with the reference (+) - griseofulvin (IC50 19, 19.5 µM). Based on the antibiofilm activity, compound 1 displayed as well potent activity against Staphylococcus aureus with an MIC of 0.25 mg/mL. Isolation of the producing fungus and taxonomical characterization is stated as well.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
