Roseic acid and roseolactones A and B, Furan-Cucurbitane Triterpenes from Russula aurora and R. minutula (Basidiomycota)
Articolo
Data di Pubblicazione:
2014
Citazione:
Roseic acid and roseolactones A and B, Furan-Cucurbitane Triterpenes from Russula aurora and R. minutula (Basidiomycota) / M. Clericuzio, G. Vidari, C. Cassino, L. Legnani, L. Toma. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2014:25(2014), pp. 5462-5468. [10.1002/ejoc.201402208]
Abstract:
Three new seco-cucurbitane triterpenes, viz. roseic acid (1) and roseolactones A (2) and B (3), all bearing a furan moiety condensed to the B-ring, were isolated from Russula aurora and R. minutula. Their structures were elucidated using 1D and 2D NMR spectroscopy, and ESI HRMS. Compounds 2 and 3 were found to be epimers at C-23. A detailed ab initio theoretical investigation was carried out to assess their relative stereochemistries. The conformations and NMR spectra of the two isomers were calculated, and the results were compared to the experimental data. The new compounds show a bright pink reaction with sulfo-vanillin at room temperature, and they are therefore responsible for the systematically significant reaction performed by mycologists on R. aurora and R. minutula fruiting bodies. A mixture of compounds 2 and 3 was found to be weakly active against HepG2, WISH, and CAKI-1 human tumour cells.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Natural products; Terpenoids; Structure elucidation; Conformation analysis; Ab initio calculations
Elenco autori:
M. Clericuzio, G. Vidari, C. Cassino, L. Legnani, L. Toma
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