The acid-catalyzed cyclization of mono epoxides of cnicin acetonide (3) was investigated. Several 6,12-eudesmanolides were obtained, and their stereochemistry established by extensive spectroscopic analyses. Chemical correlations also led to the assignment of the absolute configuration of 1β,10α-epoxy-salonitenolide (13), a previously isolated natural product. The cytotoxic activities of some compounds were determined against A549 and MCF-7 tumor cell lines. The esterified germacranolides 2–6 were selectively cytotoxic against the MCF-7 breast cancer cell line.
Rosselli, S., Maggio, A.M., Raccuglia, R.A., Morris-Natschke, S.L., Bastow, K.F., Lee, K.H., et al. (2010). Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta, 10alpha-epoxy-salonitenolide. NATURAL PRODUCT COMMUNICATIONS, 5(5), 675-680.
Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta, 10alpha-epoxy-salonitenolide
ROSSELLI, Sergio;MAGGIO, Antonella Maria;BRUNO, Maurizio
2010-01-01
Abstract
The acid-catalyzed cyclization of mono epoxides of cnicin acetonide (3) was investigated. Several 6,12-eudesmanolides were obtained, and their stereochemistry established by extensive spectroscopic analyses. Chemical correlations also led to the assignment of the absolute configuration of 1β,10α-epoxy-salonitenolide (13), a previously isolated natural product. The cytotoxic activities of some compounds were determined against A549 and MCF-7 tumor cell lines. The esterified germacranolides 2–6 were selectively cytotoxic against the MCF-7 breast cancer cell line.
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