Acremonidin B
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| Category | Antibiotics |
| Catalog number | BBF-00017 |
| CAS | |
| Molecular Weight | 572.52 |
| Molecular Formula | C31H24O11 |
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Description
Acremonidins A to approximately E (1 to approximately 5) were produced by fermentation of Acremonium sp. LL-Cyan 416, in heterogeneous phases. Acremonidins B showed moderate activity against Gram-positive bacteria, including the methicillin-resistant staphylococci and vancomycin-resistant enterococci.
Specification
| IUPAC Name | methyl 3,6-dihydroxy-2-[(1R,2S,12S)-2,7,9,14,16-pentahydroxy-5-methyl-11-oxopentacyclo[10.7.2.01,10.03,8.013,18]henicosa-3(8),4,6,9,13,15,17,20-octaene-15-carbonyl]benzoate |
| Canonical SMILES | CC1=CC2=C(C(=C1)O)C(=C3C(=O)C4C=CC3(C2O)CC5=CC(=C(C(=C45)O)C(=O)C6=C(C=CC(=C6C(=O)OC)O)O)O)O |
| InChI | InChI=1S/C31H24O11/c1-11-7-14-20(17(34)8-11)28(39)24-25(36)13-5-6-31(24,29(14)40)10-12-9-18(35)23(26(37)19(12)13)27(38)21-15(32)3-4-16(33)22(21)30(41)42-2/h3-9,13,29,32-35,37,39-40H,10H2,1-2H3/t13-,29-,31-/m0/s1 |
| InChI Key | HIABMWDNEAHXTD-XUMFIBQQSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
Reference Reading
1. Acremonidins, new polyketide-derived antibiotics produced by Acremonium sp., LL-Cyan 416
Haiyin He, Ramunas Bigelis, Eric H Solum, Michael Greenstein, Guy T Carter J Antibiot (Tokyo). 2003 Nov;56(11):923-30. doi: 10.7164/antibiotics.56.923.
Acremonidins A to approximately E (1 to approximately 5) were produced by fermentation of Acremonium sp., LL-Cyan 416, in heterogeneous phases. The structures of these compounds, containing a bridging keto group, were determined by spectroscopic analysis. Acremonidins A and B showed moderate activity against Gram-positive bacteria, including the methicillin-resistant staphylococci and vancomycin-resistant enterococci. Selective acylations of acremonidin B afforded ester derivatives 6 to approximately 9 that exhibited improved antibacterial activity.
2. Cytotoxic xanthone-anthraquinone heterodimers from an unidentified fungus of the order Hypocreales (MSX 17022)
Sloan Ayers, Tyler N Graf, Audrey F Adcock, David J Kroll, Qi Shen, Steven M Swanson, Susan Matthew, Esperanza J Carcache de Blanco, Mansukh C Wani, Blaise A Darveaux, Cedric J Pearce, Nicholas H Oberlies J Antibiot (Tokyo). 2012 Jan;65(1):3-8. doi: 10.1038/ja.2011.95. Epub 2011 Nov 9.
Two new xanthone-anthraquinone heterodimers, acremoxanthone C (5) and acremoxanthone D (2), have been isolated from an extract of an unidentified fungus of the order Hypocreales (MSX 17022) by bioactivity-directed fractionation as part of a search for anticancer leads from filamentous fungi. Two known related compounds, acremonidin A (4) and acremonidin C (3) were also isolated, as was a known benzophenone, moniliphenone (1). The structures of these isolates were determined via extensive use of spectroscopic and spectrometric tools in conjunction with comparisons to the literature. All compounds (1-5) were evaluated against a suite of biological assays, including those for cytotoxicity, inhibition of the 20S proteasome, mitochondrial transmembrane potential and nuclear factor-κB.
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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 ╳
