Eupenoxide
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00879 |
| CAS | 89773-19-3 |
| Molecular Weight | 254.32 |
| Molecular Formula | C14H22O4 |
Online Inquiry
Description
Eupenoxide is an antibiotic produced by Eupenicillum sp. It has antifungal activity.
Specification
| Synonyms | (+)-Eupenoxide |
| IUPAC Name | (1S,2R,5S,6R)-3-[(E)-hept-1-enyl]-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol |
| Canonical SMILES | CCCCCC=CC1=C(C(C2C(C1O)O2)O)CO |
| InChI | InChI=1S/C14H22O4/c1-2-3-4-5-6-7-9-10(8-15)12(17)14-13(18-14)11(9)16/h6-7,11-17H,2-5,8H2,1H3/b7-6+/t11-,12+,13+,14-/m1/s1 |
| InChI Key | CBWMFTMZESYHBT-KWUVHTBZSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 466.7±45.0 °C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. Cytotoxic alkylated hydroquinone, phenol, and cyclohexenone derivatives from Aspergillus violaceofuscus Gasperini
Yusuke Myobatake, Kenji Takemoto, Shinji Kamisuki, Natsuki Inoue, Ayato Takasaki, Toshifumi Takeuchi, Yoshiyuki Mizushina, Fumio Sugawara J Nat Prod. 2014 May 23;77(5):1236-40. doi: 10.1021/np401017g. Epub 2014 May 1.
New alkylated hydroquinones violaceoid A (1), violaceoid B (2), and violaceoid C (3), an alkylated phenol violaceoid D (4), and a cyclohexenoid violaceoid E (5) were isolated from a culture broth of Aspergillus violaceofuscus Gasperini isolated from moss. The structures were identified by interpretation of spectroscopic data (1D and 2D NMR, MS, and IR). Two known compounds, the cyclohexenoid 6 and eupenoxide (7), were also isolated. Compound 6 was isolated for the first time as a natural product and named violaceoid F. Isolated compounds were tested for cytotoxic activity against five human cancer cell lines and a mouse macrophage cell line. Violaceoid A was the most potent of the seven compounds against all cell lines. Violaceoid C and D exhibited cytotoxicity against the leukemia cell lines with LD50 values 5.9-8.3 μM, while violaceoid F was found to be cytotoxic against HCT116 and RAW264.7 with LD50 values of 6.4 and 6.5 μM, respectively. These results demonstrate that violaceoid derivatives are a new class of cytotoxic hydroquinones with a hydroxymethyl and a linear alkyl substituent.
2. Phomoxins B and C: polyketides from an endophytic fungus of the genus Eupenicillium
Rohan A Davis, Vesna Andjic, Michael Kotiw, Roger G Shivas Phytochemistry. 2005 Dec;66(23):2771-5. doi: 10.1016/j.phytochem.2005.09.004. Epub 2005 Oct 20.
Chemical investigations of the culture broth from an endophytic fungus Eupenicillium sp. have afforded two natural products phomoxins B (1) and C (2) as well as the previously reported fungal metabolite eupenoxide (3). Compounds 1 and 2 both contain a cyclic carbonate moiety that is rare among natural products. This paper reports the full spectroscopic characterisation of phomoxins B (1) and C (2) by NMR, UV, IR and MS data. All compounds were inactive against a panel of nosocomial microbes.
3. Metabolites from the fungus Phoma sp. 7210, associated with Aizoon canariense
Jingqiu Dai, Hidayat Hussain, Siegfried Dräger, Barbara Schulz, Tibor Kurtán, Gennaro Pescitelli, Ulrich Flörke, Karsten Krohn Nat Prod Commun. 2010 Aug;5(8):1175-80.
A new metabolite, 3,16-diketoaphidicolan (1), was isolated together with four known compounds: aphidicolin (2), 17-acetyl-aphidicolin (3), (+)-eupenoxide (4), and phomoxanthone A (5) from the endophytic fungus Phoma sp. The structure of the new compound 1 was determined by spectroscopic methods (mainly extensive 1D and 2D NMR experiments and by mass spectral measurements) and confirmed by X-ray crystallography. Its absolute configuration was assigned by means of the solid-state CD/TDDFT approach comparing the solid-state CD spectrum with the TDDFT-calculated one on the X-ray geometry.
Recommended Products
| BBF-02614 | Nystatin | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
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 ╳
