Anhydroexfoliamycin
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| Category | Antibiotics |
| Catalog number | BBF-00890 |
| CAS | 148084-39-3 |
| Molecular Weight | 416.42 |
| Molecular Formula | C22H24O8 |
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Description
Anhydroexfoliamycin is a naphthoquinone antibiotic produced by Streptomyces exfoliamycin Tu 1424. Activity against gram-positive bacteria.
Specification
| IUPAC Name | 8-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-10-hydroxy-3-methyl-1-propyl-1H-benzo[g]isochromene-6,9-dione |
| Canonical SMILES | CCCC1C2=C(C3=C(C=C2C=C(O1)C)C(=O)C=C(C3=O)C4C(C(C(O4)CO)O)O)O |
| InChI | InChI=1S/C22H24O8/c1-3-4-14-16-10(5-9(2)29-14)6-11-13(24)7-12(18(25)17(11)20(16)27)22-21(28)19(26)15(8-23)30-22/h5-7,14-15,19,21-23,26-28H,3-4,8H2,1-2H3 |
| InChI Key | SZBHSSGJBUMHOR-UHFFFAOYSA-N |
Properties
| Appearance | Dark Red Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 167°C |
| Solubility | Soluble in Methanol, methyl ether |
Reference Reading
1. The Streptomyces metabolite anhydroexfoliamycin ameliorates hallmarks of Alzheimer's disease in vitro and in vivo
M Leirós, E Alonso, M E Rateb, R Ebel, M Jaspars, A Alfonso, L M Botana Neuroscience. 2015 Oct 1;305:26-35. doi: 10.1016/j.neuroscience.2015.07.082. Epub 2015 Aug 3.
Anhydroexfoliamycin (1) and undecylprodigiosin (2) have been previously described as neuroprotective molecules against oxidative stress in neurons. Since oxidative stress is strongly correlated with neurodegenerative diseases, we have evaluated their effects over the principal hallmarks of Alzheimer's disease (AD). Both compounds were tested in vitro in two different neuroblastoma cellular models, one for amyloid precursor protein metabolism studies (BE(2)-M17) and another one specific for taupathology in AD (SH-SY5Y-TMHT441). Amyloid-beta (Aβ) levels, β-secretase (BACE1) activity, tau phosphorylation, extracellular signal-regulated kinase (ERK) and glycogen synthase kinase-3beta (GSK3β) expression were analyzed and while undecylprodigiosin (2) produced poor results, anhydroexfoliamycin (1) strongly inhibited GSK3β, reducing tau phosphorylation in vitro (0.1 μM). A competitive assay of anhydroexfoliamycin (1) and the specific c-Jun N-terminal kinase (JNK) inhibitor, SP600125, showed that the reduction of the phosphorylated tau levels is mediated by the JNK pathway in SH-SY5Y-TMHT441 cells. Thus, this compound was tested in vivo by intraperitoneal administration in 3xTg-AD mice, confirming the positive results registered in the in vitro assays. This work presents anhydroexfoliamycin (1) as a promising candidate for further studies in drug development against neurodegenerative diseases.
2. Anti-Alzheimer's Molecules Derived from Marine Life: Understanding Molecular Mechanisms and Therapeutic Potential
Md Tanvir Kabir, Md Sahab Uddin, Philippe Jeandet, Talha Bin Emran, Saikat Mitra, Ghadeer M Albadrani, Amany A Sayed, Mohamed M Abdel-Daim, Jesus Simal-Gandara Mar Drugs. 2021 Apr 28;19(5):251. doi: 10.3390/md19050251.
Alzheimer's disease (AD) is a devastating neurodegenerative disease and the most common cause of dementia. It has been confirmed that the pathological processes that intervene in AD development are linked with oxidative damage to neurons, neuroinflammation, tau phosphorylation, amyloid beta (Aβ) aggregation, glutamate excitotoxicity, and cholinergic deficit. Still, there is no available therapy that can cure AD. Available therapies only manage some of the AD symptoms at the early stages of AD. Various studies have revealed that bioactive compounds derived from marine organisms and plants can exert neuroprotective activities with fewer adverse events, as compared with synthetic drugs. Furthermore, marine organisms have been identified as a source of novel compounds with therapeutic potential. Thus, there is a growing interest regarding bioactive compounds derived from marine sources that have anti-AD potentials. Various marine drugs including bryostatin-1, homotaurine, anabaseine and its derivative, rifampicins, anhydroexfoliamycin, undecylprodigioisin, gracilins, 13-desmethyl spirolide-C, and dictyostatin displayed excellent bioavailability and efficacy against AD. Most of these marine drugs were found to be well-tolerated in AD patients, along with no significant drug-associated adverse events. In this review, we focus on the drugs derived from marine life that can be useful in AD treatment and also summarize the therapeutic agents that are currently used to treat AD.
3. Anhydroexfoliamycin, a Streptomyces Secondary Metabolite, Mitigates Microglia-Driven Inflammation
Sandra Gegunde, Amparo Alfonso, Rebeca Alvariño, Nadia Pérez-Fuentes, Luis M Botana ACS Chem Neurosci. 2021 Jul 7;12(13):2336-2346. doi: 10.1021/acschemneuro.1c00033. Epub 2021 Jun 10.
Anhydroexfoliamycin, a secondary metabolite from Streptomyces, has shown antioxidant properties in primary cortical neurons reducing neurodegenerative hallmarks diseases, both in vitro and in vivo models. Activated microglia, in the central nervous system, plays a crucial role in neuroinflammation and is associated with neurodegeneration. Therefore, the aim of the present study was to determine the anti-inflammatory and antioxidant potential of the anhydroexfoliamycin over microglia BV2 cells. Neuroinflammation was simulated by incubation of microglia cells in the presence of lipopolysaccharide to activate proinflammatory transduction pathways. Moreover, a coculture of neuron SH-SY5Y and microglia BV2 cells was used to evaluate the neuroprotective properties of the Streptomyces metabolite. When microglia cells were preincubated with anhydroexfoliamycin, proinflammatory pathways, such as the translocation of the nuclear factor κB, the phosphorylation of c-Jun N-terminal kinase, and the inducible nitric oxide synthase expression, were inhibited. In addition, intracellular reactive oxygen species generation and the liberation of nitric oxide, interleukin 6, and tumor necrosis factor α were also decreased. Besides, the Streptomyces-derived compound showed antioxidant properties promoting the translocation of the factor erythroid 2-related factor 2 and protecting the SH-SY5Y cells from the neurotoxic mediators released by activated microglia. The effects of this compound were at the same level as the immunosuppressive drug cyclosporine A. Therefore, these results indicate that anhydroexfoliamycin is a promising tool to control microglia-driven inflammation with therapeutic potential in neuroinflammation.
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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 ╳
