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Absolute configuration and anti-tumor activity of torrubiellin B

Author:
Pérez Hemphill, Catalina Francis, Daletos, Georgios, Hamacher, Alexandra, Kassack, Matthias Ullrich, Lin, Wenhan, Mándi, Attila, Kurtán, Tibor, Proksch, Peter
Source:
Tetrahedron letters 2015 v.56 no.30 pp. 4430-4433
ISSN:
0040-4039
Subject:
Acremonium, Sonneratia caseolaris, anthracenes, antineoplastic activity, cell lines, chemical reactions, chemical structure, circular dichroism spectroscopy, cisplatin, endophytes, fungi, inhibitory concentration 50, leaves, neoplasm cells, neoplasms
Abstract:
The dimeric anthracene derivative torrubiellin B (1) was isolated from the endophytic fungus Acremonium sp. that had been obtained from leaves of the Mangrove plant Sonneratia caseolaris. The absolute configuration of 1 was established as (5′R,10′S,10a′R) for the first time on the basis of its electronic circular dichroism (ECD) spectra aided with TDDFT-ECD calculations. Torrubiellin B (1) exhibited strong anti-tumor activity when tested in vitro against several solid cancer cell lines including cells that are resistant against the widely used cytostatic drug cisplatin. The IC50 values of 1 against cisplatin sensitive and cisplatin resistant cells were in the range of 0.2–2.6μM depending on cell line investigated.
Agid:
6040093