Brefeldin B
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| Category | Antibiotics |
| Catalog number | BBF-00178 |
| CAS | |
| Molecular Weight | 266.33 |
| Molecular Formula | C15H22O4 |
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Description
Brefeldin is an antibiotic produced by Penicillum brefeldianum S-464, Pen. cyaneum S-ll, Pen. decumbens, Pen. simplicissimum S-544, etc.
Properties
| Appearance | Colorless needle Crystal |
| Melting Point | 161°C |
Reference Reading
1. Brefeldin A from the Deep-Sea-Derived Fungus Fusarium sp. Targets on RIPK3 to Inhibit TNFα-Induced Necroptosis
Jia-Yi Shi, Chao-Feng Wang, Ming-Min Xie, You-Jia Hao, Ning Wang, Hua-Bin Ma, Xian-Wen Yang Chem Biodivers. 2022 Oct;19(10):e202200696. doi: 10.1002/cbdv.202200696. Epub 2022 Sep 16.
From the deep-sea-derived Fusarium sp. ZEN-48, four known compounds were obtained. Their structures were established by extensive analyses of the NMR, HR-ESI-MS, and the X-ray crystallographic data as brefeldin A (BFA, 1), brevianamide F (2), N-acetyltryptamine (3), and (+)-diaporthin (4). Although BFA was extensively investigated for its potent bioactivities, its role on TNFα-induced necroptosis was incompletely understood. In this study, BFA showed significant inhibition on TNFα-induced necroptosis by disrupting the necrosome formation and suppressing the phosphorylation of RIPK3 and MLKL (IC50 =0.5 μM). While, it had no effect on TNFα-induced NF-κB/MAPKs activation and apoptosis. The finding raised significant implications of BFA for necroptosis-related inflammatory disease therapy and new drug development from marine fungi.
2. Trafficking of newly synthesized surfactant protein B to the lamellar body in alveolar type II cells
Kazuhiro Osanai, Shiro Mizuno, Hirohisa Toga, Keiji Takahashi Cell Tissue Res. 2020 Sep;381(3):427-438. doi: 10.1007/s00441-020-03232-7. Epub 2020 Jun 15.
Lung surfactant accumulates in the lamellar body (LB) via not only the secretory (anterograde) pathway but also the endocytic (retrograde) pathway. Our previous studies suggested that the major surfactant components, phosphatidylcholine and surfactant protein A take independent trafficking routes in alveolar type II cells. Thus, trafficking of surfactant protein B (SP-B), a major hydrophobic surfactant apoprotein, should be re-evaluated by a straightforward method. Radiolabeling of cells and subsequent cell fractionation were employed to pursue the sequential trafficking of newly synthesized SP-B in rabbit alveolar type II cells. The LB fraction was prepared by gradient ultracentrifugation. Immunoprecipitation from the culture medium, total cells, and LB fraction was carried out with anti-SP-B antibody. Newly synthesized [35S]-pro-SP-B (~ 42 kDa) was detected in the cells after 1 h. An ~ 8-kDa mature form of [35S]-SP-B was detected in the cells after 3 h and in the LB after 6 h. Mature [35S]-SP-B was predominant in the cells after 24 h, and the dominant portion was present in the LB. In contrast, only a small amount of mature [35S]-SP-B was present in the culture medium. Molecular processing of ~ 42 kDa [35S]-pro-SP-B and transport to the LB was inhibited by brefeldin A, which disassembles the Golgi apparatus. These results suggest that newly synthesized SP-B is sorted to the LB via the Golgi and stored until exocytosis. This pathway is distinct from the pathways reported for phosphatidylcholine and surfactant protein A.
3. Dibrefeldins A and B, A pair of epimers representing the first brefeldin A dimers with cytotoxic activities from Penicillium janthinellum
Fanrong Zeng, Chunmei Chen, Ali Adhab Al Chnani, Qun Zhou, Qingyi Tong, Wenjing Wang, Yi Zang, Jiaojiao Gong, Zhaodi Wu, Junjun Liu, Jianping Wang, Hucheng Zhu, Yonghui Zhang Bioorg Chem. 2019 May;86:176-182. doi: 10.1016/j.bioorg.2019.01.042. Epub 2019 Jan 25.
Dibrefeldins A and B (1 and 2), two unexpected brefeldin A (BFA) dimers, as well as brefeldin F (3), brefeldin G (4), and 14-hydroxy-BFA (5), three new BFA derivatives, together with three new naturally occurring BFA derivatives (6-8) and four known analogues (9-12), were isolated from the fungus Penicillium janthinellum. Dibrefeldins A and B (1 and 2) represent the first examples of BFA dimers formed by an esterification between two BFA monomer units. Brefeldin F (3) has an α,β-unsaturated γ-lactone ring, and this moiety was first discovered in naturally occurring BFA derivatives. The structures and relative/absolute configurations of these derivatives were elucidated by extensive spectroscopic methods, 13C NMR calculations, and single-crystal X-ray diffraction. Compounds 1, 2, 8, and 9 showed excellent cytotoxic activities against six cancer cell lines with IC50 values ranging from 0.01 to 4.45 μM.
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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 ╳
