synthetic efforts for stereo structure determination of cytotoxic marine natural product pericosines as metabolites of periconia sp. from sea hare合成的努力为立体结构细胞毒性测定海洋天然产品pericosines代谢物的periconia sp.海兔.pdf

Int. J. Mol. Sci. 2008, 9, 401-421 International Journal of Molecular Sciences ISSN 1422-0067 © 2008 by MDPI /ijms Review Synthetic Efforts for Stereo Structure Determination of Cytotoxic Marine Natural Product Pericosines as Metabolites of Periconia sp. from Sea Hare Yoshihide Usami,* Hayato Ichikawa and Masao Arimoto Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan * Author to whom correspondence should be addressed; E-mail: usami@gly.oups.ac.jp Received: 10 January 2008; in revised form: 18 March 2008 / Accepted: 19 March 2008 / Published: 24 March 2008 Abstract: Pericosines are unique C7 cyclohexenoid metabolites of Periconia byssoides OUPS-N133 fungus that was originally isolated from the sea hare, Aplysia kurodai . Pericosines show significant in vitro cytotoxicity against P388 lymphocytic leukemia cells. Pericosine A, in particular, shows the most potent activity and significant in vivo antitumor activity against P388 cells. Thus, pericosines are promising candidates for seed compounds of anticancer drugs. However, before the total syntheses of pericosines were accomplished, their stereo structures could not be determined by spectral analyses because they have multi- functionalized cyclohexenoid structures with torsional strain. In this review, synthetic efforts for pericosines in this decade are surveyed. Keywords: marine natural pro