Bromotheoynic acid, a brominated acetylenic acid from the marine sponge Theonella swinhoei

Abstract

A new brominated C₁₇ acetylenic acid (1) designated as bromotheoynic acid has been isolated from the marine sponge Theonella swinhoei, collected off the coast of Tanegashima, Kagoshima Prefecture, Japan. The structure was determined on the basis of the analysis of its extensive 2D NMR spectroscopic data as well as HRMS. Bromotheoynic acid (1) inhibited maturation of starfish oocytes and cell division of fertilised starfish eggs. Bromotheoynic acid (1) also inhibited proliferation of human leukaemia U937 and HL60 cells, human lung cancer A549 and H1299 cells, and human embryonic kidney 293 (HEK293) cells.

Keywords:

• marine sponge
• Theonella swinhoei
• brominated acetylene
• starfish egg

Acknowledgements

The authors thank Captain A. Goh and the crew of R/V Toyoshio-Maru of Hiroshima University, for the help in the collection of sponge samples, and Professor Patricia R. Bergquist, The University of Auckland, New Zealand, for the identification of the sponge specimen. This work was supported in part by a Grant-in-Aid for Scientific Research (C), No. 21510235, from Japan Society for the Promotion of Science (JSPS) to S.O.