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Kawamura, Atsushi; Kita, Masaki; Kigoshi, Hideo
Angewandte Chemie International Edition, 06/2015, Letnik: 54, Številka: 24Journal Article
A new 9,11-secosteroid having an unprecedented tricyclic gamma-diketone structure, aplysiasecosterolA (1), was isolated from the sea hare Aplysia kurodai. The structure was determined by one- and two-dimensional NMR spectroscopic analysis, molecular modeling studies, a comparison of experimental and calculated ECD spectra, and a modified Mosher's method. AplysiasecosterolA (1) exhibited cytotoxicity against human myelocytic leukemia HL-60 cells. A biosynthetic pathway for 1 from a known cholesterol was proposed and includes twice alpha-ketol rearrangements and an intramolecular acetalization.
