Aranorosin
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| Category | Antibiotics |
| Catalog number | BBF-03967 |
| CAS | 117184-53-9 |
| Molecular Weight | 419.51 |
| Molecular Formula | C23H33NO6 |
| Purity | ≥95% |
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Description
Aranorosin is a fungal metabolite originally isolated from P. roseus and an inhibitor of anti-apoptotic functions regulated by Bcl-2. It has antimicrobial activity against B. subtilis, A. niger, and C. albicans when used at a concentration of 1 mg/ml. Aranorosin also reduces viability in apoptosis-resistant HeLa/Bcl-2 cells. Aranorosin also inhibits enzyme AAC(6')/APH(2'') which plays a role in arbekacin (ABK)-resistance in MRSA.
Specification
| Synonyms | Spiro[4,8-dioxatricyclo[5.1.0.03,5]octane-2,2'(3'H)-furan], 2,4-dodecadienamide deriv.; Aranorosine |
| Storage | Store at -20°C |
| IUPAC Name | (2E,4E,6R)-N-[(1S,3R,5S,7R)-2'-hydroxy-6-oxospiro[4,8-dioxatricyclo[5.1.0.03,5]octane-2,5'-oxolane]-3'-yl]-4,6-dimethyldodeca-2,4-dienamide |
| Canonical SMILES | CCCCCCC(C)C=C(C)C=CC(=O)NC1CC2(C3C(O3)C(=O)C4C2O4)OC1O |
| InChI | InChI=1S/C23H33NO6/c1-4-5-6-7-8-13(2)11-14(3)9-10-16(25)24-15-12-23(30-22(15)27)20-18(28-20)17(26)19-21(23)29-19/h9-11,13,15,18-22,27H,4-8,12H2,1-3H3,(H,24,25)/b10-9+,14-11+/t13-,15+,18-,19+,20-,21+,22-,23-/m1/s1 |
| InChI Key | JHTWWPWUODMKEO-ZVNJHPNESA-N |
Properties
| Appearance | Solid Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Boiling Point | 650.4°C at 760 mmHg |
| Density | 1.23 g/cm3 |
| Solubility | Soluble in DMSO, ethanol, methanol |
Reference Reading
1. Aranorosin and a novel derivative inhibit the anti-apoptotic functions regulated by Bcl-2
Mitsunobu Hara, Rieko Tanaka, Takayuki Nakashima, Yoshinori Yamashita, Yutaka Kanda Biochem Biophys Res Commun . 2008 Dec 26;377(4):1085-90. doi: 10.1016/j.bbrc.2008.10.112.
Bcl-2 is an intracellular membrane protein that prevents cells from undergoing apoptosis in response to various cell-death signals. It negatively regulates mitochondrial outer membrane permeabilization, which is responsible for the release of apoptogenic factors and the subsequent activation of caspases. A microbial metabolite, aranorosin, was identified as an inhibitor of the anti-apoptotic function of Bcl-2. Based on its structure, a more potent derivative, K050, was synthesized. Apoptosis could be induced in a cell line that overexpressed Bcl-2 when cells were treated with an anti-Fas antibody in addition to K050, at sub-micromolar concentrations. Furthermore, K050 inhibited anti-apoptotic functions regulated by Bcl-2, resulting in a Fas-triggered mitochondrial transmembrane potential loss, the activation of caspase-9, and a morphological change to apoptosis. Inhibition of cell-based function of Bcl-2 and its anti-apoptotic effects could serve as useful pharmacological effects. Thus, a novel aranorosin derivative, K050, could be a potent therapeutic agent against Bcl-2-overexpressing human malignancies.
2. Aranorosinol A and aranorosinol B, two new metabolites from Pseudoarachniotus roseus: production, isolation, structure elucidation and biological properties
J Blumbach, E K Vijayakumar, K Roy, B N Ganguli, T Mukhopadhyay, S Chatterjee, R G Bhat J Antibiot (Tokyo) . 1992 Oct;45(10):1592-8. doi: 10.7164/antibiotics.45.1592.
Two new secondary metabolites, aranorosinol A (1) and aranorosinol B (2), were isolated from a strain of Pseudoarachniotus roseus. Their structures were elucidated on the basis of their spectral properties and chemical transformations and were found to be similar to aranorosin (3) isolated from the same strain.
3. Cytotoxic acyl amides from the soil fungus Gymnascella dankaliensis
Mohammed Abdel-Aziz, Peter Proksch, Werner E G Müller, Amal H Aly, Wenhan Lin, Lena Hammerschmidt, Georgios Daletos Bioorg Med Chem . 2015 Feb 15;23(4):712-9. doi: 10.1016/j.bmc.2014.12.068.
The soil fungus Gymnascella dankaliensis was collected in the vicinity of the Giza pyramids, Egypt. When grown on solid rice medium the fungus yielded four new compounds including 11'-carboxygymnastatin N (1), gymnastatin S (2), dankamide (3), and aranorosin-2-methylether (4), the latter having been reported previously only as a semisynthetic compound. In addition, six known metabolites (5-10) were isolated. Addition of NaCl or KBr to the rice medium resulted in the accumulation of chlorinated or brominated compounds as indicated by LC-MS analysis due to the characteristic isotope patterns observed. From the rice medium spiked with 3.5% NaCl the known chlorinated compounds gymnastatin A (11) and gymnastatin B (12) were obtained. All isolated compounds were unambiguously structurally elucidated on the basis of comprehensive spectral analysis (1D and 2D NMR, and mass spectrometry), as well as by comparison with the literature. Compounds 4, 7 and 11 showed potent cytotoxicity against the murine lymphoma cell line L5178Y (IC50 values 0.44, 0.58 and 0.64μM, respectively), whereas 12 exhibited moderate activity with an IC50 value of 5.80μM.
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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 ╳
