779353-80-9Relevant academic research and scientific papers
Isolation and stereostructure of aurilide, a novel cyclodepsipeptide from the Japanese sea hare Dolabella auricularia
Suenaga, Kiyotake,Mutou, Tsuyoshi,Shibata, Takunobu,Itoh, Takashi,Kigoshi, Hideo,Yamada, Kiyoyuki
, p. 6771 - 6774 (1996)
Aurilide (1), a new 26-membered cyclodepsipeptide, has been isolated from the Japanese sea hare Dolabella auricularia. The gross structure of 1 was established by spectroscopic analysis. The absolute stereostructure of 1 was determined by HPLC analysis of
Aurilide, a cytotoxic depsipeptide from the sea hare Dolabella auricularia: Isolation, structure determination, synthesis, and biological activity
Suenaga, Kiyotake,Mutou, Tsuyoshi,Shibata, Takunobu,Itoh, Takashi,Fujita, Tatsuya,Takada, Noboru,Hayamizu, Kozue,Takagi, Masaki,Irifune, Taiji,Kigoshi, Hideo,Yamada, Kiyoyuki
, p. 8509 - 8527 (2007/10/03)
The bioassay-guided fractionation of the cytotoxic constituents of the Japanese sea hare Dollabella auricularia led to the isolation of aurilide (1), a 26-membered cyclodepsipeptide. The gross structure of 1 was established by spectroscopic analysis including 2D NMR techniques. The absolute stereostructure was determined by chiral HPLC analysis of acid hydrolysates of 1 and by the enantioselective synthesis of a degradation product arising from a dihydroxylated fatty acid portion. The enantioselective synthesis of 1 was achieved in 12% overall yield (16 steps) and confirmed the absolute stereostructure of 1. The cytotoxicity of 1 was evaluated using a synthetic sample, which was found to exhibit potent cytotoxicity against HeLa S 3 cells with an IC50 of 0.011 μg/mL. Further biological and pharmacological studies of 1 have been carried out by using synthetic 1. Graphical abstract.
