Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta,10alpha-epoxy-salonitenolide.
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 1beta,10alpha-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
Sergio
S
Dipartimento Chimica Organica E. Paternò, Università di Palermo, Viale delle Scienze, Parco d'Orleans II, 90128 Palermo, Italy.
Maggio
Antonella Maria
AM
Raccuglia
Rosa Angela
RA
Morris-Natschke
Susan L
SL
Bastow
Kenneth F
KF
Lee
Kuo-Hsiung
KH
Bruno
Maurizio
M
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000633:toxicity; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D031179:Centaurea / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification*; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification*; D045788:Sesquiterpenes, Germacrane / Q000737:chemistry* / Q000633:toxicity; D012802:Sicily
D000972:Antineoplastic Agents, Phytogenic; D010936:Plant Extracts; D012717:Sesquiterpenes; D045788:Sesquiterpenes, Germacrane; C432449:germacranolide; C011103:salonitenolide; C012849:cnicin