Fimbricalyx A, a novel phenanthrenone derivative having a rare 2H-benz[e]inden-2-one substructure

Authors

Prapairat Seephonkai, University of Wollongong
Stephen G. Pyne, University of WollongongFollow
Anthony C. Willis, Australian National University
Wilford Lie, University of WollongongFollow

RIS ID

76829

Publication Details

Seephonkai, P., Pyne, S. G., Willis, A. C. & Lie, W. (2013). Fimbricalyx A, a novel phenanthrenone derivative having a rare 2H-benz[e]inden-2-one substructure. Tetrahedron Letters, 54 (16), 2085-2088.

Abstract

Fimbricalyx A (1), a novel phenanthrenone derivative having a rare 2H-benz[e]inden-2-one substructure, was isolated from the root extract of Strophioblachia fimbricalyx. The structure of 1 was elucidated on the basis of the NMR and MS data and confirmed by X-ray crystallography. This compound showed cytotoxicity against KB, MCF7 and NCI-H187 cancer cells with IC50 values of 38.4, 28.7 and 8.3 μg/mL, respectively. A possible biosynthesis of 1, via a ring-contracted p-quinone methide intermediate derived from a phenanthrenone precursor, is proposed.