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Epanorin

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Epanorin
Category Enzyme inhibitors
Catalog number BBF-05012
CAS 18463-10-0
Molecular Weight 435.47
Molecular Formula C25H25NO6

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Epanorin is a lichen metabolite that can inhibit the proliferation of MCF-7 breast cancer cells.

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Synonyms L-Leucine, N-[(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)phenylacetyl]-, methyl ester; N-[2-(3-Hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)-2-phenylacetyl]-L-leucine methyl ester; (-)-Epanorin
IUPAC Name methyl (2S)-2-[[(2Z)-2-(3-hydroxy-5-oxo-4-phenylfuran-2-ylidene)-2-phenylacetyl]amino]-4-methylpentanoate
Canonical SMILES CC(C)CC(C(=O)OC)NC(=O)C(=C1C(=C(C(=O)O1)C2=CC=CC=C2)O)C3=CC=CC=C3
InChI InChI=1S/C25H25NO6/c1-15(2)14-18(24(29)31-3)26-23(28)20(17-12-8-5-9-13-17)22-21(27)19(25(30)32-22)16-10-6-4-7-11-16/h4-13,15,18,27H,14H2,1-3H3,(H,26,28)/b22-20-/t18-/m0/s1
InChI Key IBSRGCBHIASQMQ-BKBKCADHSA-N
Boiling Point 608.6±55.0°C (Predicted)
Density 1.280±0.06 g/cm3 (Predicted)
1. Epanorin, a lichen secondary metabolite, inhibits proliferation of MCF-7 breast cancer cells
Juan Palacios-Moreno, Cecilia Rubio, Wanda Quilhot, M Fernanda Cavieres, Eduardo de la Peña, Natalia V Quiñones, Hugo Díaz, Flavio Carrión, Carlos F Henríquez-Roldán, Caroline R Weinstein-Oppenheimer Biol Res. 2019 Oct 10;52(1):55. doi: 10.1186/s40659-019-0261-4.
Background: Epanorin (EP) is a secondary metabolite of the Acarospora lichenic species. EP has been found in lichenic extracts with antimicrobial activity, and UV-absorption properties have been described for closely related molecules; however, its antiproliferative activity in cancer cells has not yet been explored. It has been hypothesized that EP inhibits cancer cell growth. MCF-7 breast cancer cells, normal fibroblasts, and the non-transformed HEK-293 cell line were exposed to increasing concentrations of EP, and proliferation was assessed by the sulforhodamine-B assay. Results: MCF-7 cells exposed to EP were examined for cell cycle progression using flow cytometry, and DNA fragmentation was examined using the TUNEL assay. In addition, EP's mutagenic activity was assessed using the Salmonella typhimurium reverse mutation assay. The data showed that EP inhibits proliferation of MCF-7 cells, and it induces cell cycle arrest in G0/G1 through a DNA fragmentation-independent mechanism. Furthermore, EP's lack of overt cytotoxicity in the normal cell line HEK-293 and human fibroblasts in cell culture is supported by the absence of mutagenic activity of EP. Conclusion: EP emerges as a suitable molecule for further studies as a potential antineoplastic agent.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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