(5E)-7-Oxozeaenol
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| Category | Enzyme inhibitors |
| Catalog number | BBF-05247 |
| CAS | 1198574-97-8 |
| Molecular Weight | 362.37 |
| Molecular Formula | C19H22O7 |
| Purity | ≥95% by HPLC |
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Description
(5E)-7-Oxozeaenol, a resorcylic acid lactone isolated from the fungus MSX 63935 and Drechslera portulacae, has enzyme inhibitory effect and anticancer activities.
Specification
| Synonyms | Oxozeaenol, (5E)-7-; (3S,5E,8S,9S,11E)-3,4,9,10-tetrahydro-8,9,16-trihydroxy-14-methoxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione; LL-Z 1640-2; Cochliomycin F; (2E,5S,6S,8E,11S)-5,6,15-trihydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(18),2,8,14,16-pentaene-7,13-dione |
| Storage | Store at -20°C |
| IUPAC Name | (4S,6E,9S,10S,12E)-9,10,18-trihydroxy-16-methoxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),6,12,15,17-pentaene-2,8-dione |
| Canonical SMILES | CC1CC=CC(=O)C(C(CC=CC2=C(C(=CC(=C2)OC)O)C(=O)O1)O)O |
| InChI | InChI=1S/C19H22O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,15,18,21-23H,5,8H2,1-2H3/b6-4+,7-3+/t11-,15-,18+/m0/s1 |
| InChI Key | NEQZWEXWOFPKOT-ULSULSEOSA-N |
Properties
| Appearance | Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 666.8±55.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in DMF, DMSO, Ethanol, Methanol |
Reference Reading
1. Resorcylic acid lactones with cytotoxic and NF-κB inhibitory activities and their structure-activity relationships
Sloan Ayers, Tyler N Graf, Audrey F Adcock, David J Kroll, Susan Matthew, Esperanza J Carcache de Blanco, Qi Shen, Steven M Swanson, Mansukh C Wani, Cedric J Pearce, Nicholas H Oberlies J Nat Prod. 2011 May 27;74(5):1126-31. doi: 10.1021/np200062x. Epub 2011 Apr 22.
As part of our ongoing investigation of filamentous fungi for anticancer leads, an active fungal extract was identified from the Mycosynthetix library (MSX 63935; related to Phoma sp.). The initial extract exhibited cytotoxic activity against the H460 (human non-small cell lung carcinoma) and SF268 (human astrocytoma) cell lines and was selected for further study. Bioactivity-directed fractionation yielded resorcylic acid lactones (RALs) 1 (a new natural product) and 3 (a new compound) and the known RALs zeaenol (2), (5E)-7-oxozeaenol (4), (5Z)-7-oxozeaenol (5), and LL-Z1640-1 (6). Reduction of (5E)-7-oxozeaenol (4) with sodium borohydride produced 3, which allowed assignment of the absolute configuration of 3. Other known resorcylic acid lactones (7-12) were purchased and assayed in parallel for cytotoxicity with isolated 1-6 to investigate structure-activity relationships in the series. Moreover, the isolated compounds (1-6) were examined for activity in a suite of biological assays, including antibacterial, mitochondria transmembrane potential, and NF-κB. In the latter assay, compounds 1 and 5 displayed sub-micromolar activities that were on par with the positive control, and as such, these compounds may serve as a lead scaffold for future medicinal chemistry studies.
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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 ╳
