Fusarin C
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| Category | Bioactive by-products |
| Catalog number | BBF-01467 |
| CAS | 79748-81-5 |
| Molecular Weight | 431.48 |
| Molecular Formula | C23H29NO7 |
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Description
Fusarin C is produced by the strain of Fusarium moniliforrme which has mutagenicity.
Specification
| Synonyms | CCRIS 4320; HSDB 7078; (2E,3E,5E,7E,9E)-2-Ethylidene-11-[(1R,5a)-4a-hydroxy-4-(2-hydroxyethyl)-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1a-yl]-4,6,10-trimethyl-11-oxo-3,5,7,9-undecatetraenoic acid methyl ester |
| IUPAC Name | methyl (2E,3E,5E,7E,9E)-2-ethylidene-11-[(1R,4S,5R)-4-hydroxy-4-(2-hydroxyethyl)-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate |
| Canonical SMILES | CC=C(C=C(C)C=C(C)C=CC=C(C)C(=O)C12C(O1)C(NC2=O)(CCO)O)C(=O)OC |
| InChI | InChI=1S/C23H29NO7/c1-6-17(19(27)30-5)13-15(3)12-14(2)8-7-9-16(4)18(26)23-20(31-23)22(29,10-11-25)24-21(23)28/h6-9,12-13,20,25,29H,10-11H2,1-5H3,(H,24,28)/b8-7+,14-12+,15-13+,16-9+,17-6+/t20-,22-,23-/m0/s1 |
| InChI Key | FZFYFSUIOSWLHW-UNZVFGKVSA-N |
Properties
| Appearance | Yellow Oily Matter |
| Boiling Point | 699.3°C at 760 mmHg |
| Density | 1.247 g/cm3 |
Reference Reading
1. Structure elucidation of new fusarins revealing insights in the rearrangement mechanisms of the Fusarium mycotoxin fusarin C
Karin Kleigrewe, Filiz Aydin, Kirstin Hogrefe, Patrick Piecuch, Klaus Bergander, Ernst-Ulrich Würthwein, Hans-Ulrich Humpf J Agric Food Chem. 2012 May 30;60(21):5497-505. doi: 10.1021/jf3009469. Epub 2012 May 21.
Fusarin C is a Fusarium mycotoxin that rearranges under reversed phase chromatographic conditions. In this study, the rearrangement of fusarin C was examined in detail, and the formation of fusarins under different conditions was optimized. All relevant fusarins including (10Z)-, (8Z)-, and (6Z)-fusarin C were isolated and identified by NMR. To confirm the involvement of the 2-pyrrolidone ring in the rearrangement of fusarin C, 15-methoxy-fusarin C was synthesized. For the first time, the structure of open-chain fusarin C was elucidated, and on the basis of these data, the rearrangement product of fusarin C was identified as epi-fusarin C. The results were confirmed by detailed NMR measurements and density functional theory calculations. Furthermore, a new fusarin C like metabolite, which was named dihydrofusarin C, was detected by analysis of the crude extract of fusarin C with high-performance liquid chromatography coupled to UV and Fourier transform mass spectrometry.
2. Fusarin C acts like an estrogenic agonist and stimulates breast cancer cells in vitro
T E Sondergaard, F T Hansen, S Purup, A K Nielsen, E C Bonefeld-Jørgensen, H Giese, J L Sørensen Toxicol Lett. 2011 Aug 28;205(2):116-21. doi: 10.1016/j.toxlet.2011.05.1029. Epub 2011 Jun 13.
Fusarin C is a mycotoxin produced by several Fusarium species and has been associated with esophageal cancer due to its carcinogenic effects. Here, we report that fusarin C stimulates growth of the breast cancer cell line MCF-7. This suggests that fusarin C can act as an estrogenic agonist and should be classified as a mycoestrogen. MCF-7 cells were stimulated in the range between 0.1 and 20μM and inhibited when the concentration exceeded 50μM. The toxicity of fusarin C is comparable to other mycoestrogens such as zearalenone, but the chemical structure of fusarin C is very different from other known estrogen agonists. Furthermore, the toxicity of fusarin C was tested in five additional human cell lines Caco 2, U266, PC3, MDA-MB-231 and MCF-10a which were all inhibited when the concentration of fusarin C exceeded 10μM. To the best of our knowledge this is the first report on the mycoestrogenic properties of fusarin C.
3. Fusarin C biosynthesis in Fusarium moniliforme and Fusarium venenatum
Zhongshu Song, Russell J Cox, Colin M Lazarus, Thomas J Simpson TJ Chembiochem. 2004 Sep 6;5(9):1196-1203. doi: 10.1002/cbic.200400138.
Fragments of polyketide synthase (PKS) genes were amplified from complementary DNA (cDNA) of the fusarin C producing filamentous fungi Fusarium moniliforme and Fusarium venenatum by using degenerate oligonucleotides designed to select for fungal PKS C-methyltransferase (CMeT) domains. The PCR products, which were highly homologous to fragments of known fungal PKS CMeT domains, were used to probe cDNA and genomic DNA (gDNA) libraries of F. moniliforme and F. venenatum. A 4.0 kb cDNA clone from F. venenatum was isolated and used to prepare a hygromycin-resistance knockout cassette, which was used to produce a fusarin-deficient strain of F. venenatum (kb = 1000 bp). Similarly, a 26 kb genomic fragment, isolated on two overlapping clones from F. moniliforme, encoded a complete iterative Type I PKS fused to an unusual nonribosomal peptide synthase module. Once again, targeted gene disruption produced a fusarin-deficient strain, thereby proving that this synthase is responsible for the first steps of fusarin biosynthesis.
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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 ╳
