Fusarisetin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04251 |
| CAS | 1300041-53-5 |
| Molecular Weight | 389.49 |
| Molecular Formula | C22H31NO5 |
| Purity | >98% by HPLC |
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Description
It is an unusual pentacyclic metabolite related to equisetin isolated from Fusarium. It is identified from a natural product screen using a three-dimensional matrigel-induced bioassay to study acinar morphogenesis. It is the first inhibitor of acini reported in the literature.
Specification
| Synonyms | (+)-Fusarisetin A; 5H-Benz[4',5']indeno[2',1':3,4]furo[2,3-c]pyrrole-1,12(2H,5aH)-dione,3,3a,5b,7a,8,9,10,11,11a,11b-decahydro-3a-hydroxy-3-(hydroxymethyl)-2,5,9,11b-tetramethyl-, (3S,3aR,5S,5aS,5bS,7aS,9R,11aR,11bS,12aR)- |
| Storage | Store at -20°C |
| IUPAC Name | (1S,2S,3S,5R,6S,9R,11S,12R,15R,17S)-5-hydroxy-6-(hydroxymethyl)-3,7,11,15-tetramethyl-4-oxa-7-azapentacyclo[9.8.0.02,9.05,9.012,17]nonadec-18-ene-8,10-dione |
| Canonical SMILES | CC1CCC2C(C1)C=CC3C2(C(=O)C45C3C(OC4(C(N(C5=O)C)CO)O)C)C |
| InChI | InChI=1S/C22H31NO5/c1-11-5-7-14-13(9-11)6-8-15-17-12(2)28-22(27)16(10-24)23(4)19(26)21(17,22)18(25)20(14,15)3/h6,8,11-17,24,27H,5,7,9-10H2,1-4H3/t11-,12+,13-,14-,15+,16+,17+,20+,21+,22+/m1/s1 |
| InChI Key | IIZSEOKGOHTBLK-KDLRZXEZSA-N |
| Source | Fusarium equiseti |
Properties
| Appearance | Light Tan to Tan Solid |
| Boiling Point | 588.1±50.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Fusarisetin A: Scalable Total Synthesis and Related Studies
Emmanuel A Theodorakis, Colin Jamora, Chao-I Hung, Eduardo J E Caro-Diaz, Jing Xu, Michelle H Lacoske Chem Sci . 2012 Jan 1;3(12):3378-3386. doi: 10.1039/C2SC21308G.
Fusarisetin A (1) is a recently isolated natural product that displays an unprecedented chemical motif and remarkable bioactivities as a potent cancer migration inhibitor. We describe here our studies leading to an efficient and scalable total synthesis of 1. Essential to the strategy was the development of a new route for the formation of a trans-decalin moiety of this compound and the application of an oxidative radical cyclization (ORC) reaction that produces fusarisetin A (1) from equisetin (2) via a bio-inspired process. TEMPO-induced and metal/O(2)-promoted ORC reactions were evaluated. Biological screening in vitro confirms the reported potency of (+)-1. Importantly, ex vivo studies show that this compound is able to inhibit different types of cell migration. Moreover, the C(5) epimer of (+)-1 was also identified as a potent cancer migration inhibitor, while (-)-1 and 2 were found to be significantly less potent. The optimized synthesis is applicable on gram scale and provides a solid platform for analogue synthesis and methodical biological study.
2. Fusarisetin A, an acinar morphogenesis inhibitor from a soil fungus, Fusarium sp. FN080326
Kee-Sun Shin, Bo Yeon Kim, Jun-Pil Jang, Yukihiro Asami, Sun-Ok Kim, Jae-Hyuk Jang, Dong Oh Moon, Daisuke Hashizume, Hiroyuki Osada, Tamio Saito, Jong Seog Ahn, Makoto Muroi, Hyuncheol Oh J Am Chem Soc . 2011 May 11;133(18):6865-7. doi: 10.1021/ja1110688.
An acinar morphogenesis inhibitor named fusarisetin A (1) that possesses both an unprecedented carbon skeleton and a new pentacyclic ring system has been identified from an in-house fractionated fungal library using a three-dimensional matrigel-induced acinar morphogenesis assay system. The structure of 1 was determined in detail by NMR and circular dichroism spectroscopy, X-ray analysis, and chemical reaction experiments.
3. Nature-inspired total synthesis of (-)-fusarisetin A
Lynnie Trzoss, Jing Xu, Emmanuel A Theodorakis, Eduardo J E Caro-Diaz J Am Chem Soc . 2012 Mar 21;134(11):5072-5. doi: 10.1021/ja300807e.
A concise, protecting group-free total synthesis of (-)-fusarisetin A (1) was efficiently achieved in nine steps from commercially available (S)-(-)-citronellal. The synthetic approach was inspired by our proposed biosynthesis of 1. Key transformations of our strategy include a facile construction of the decalin moiety that is produced via a stereoselective IMDA reaction and a one-pot TEMPO-induced radical cyclization/aminolysis that forms the C ring of 1. Our route is amenable to analogue synthesis for biological evaluation.
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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 ╳
