Absolute Stereostructures of Cell Adhesion Inhibitors, Macrosphelides H and L, from Periconia byssoides OUPS-N133

Abstract

Macrosphelide L has been isolated from a strain of Periconia byssoides originally separated from the sea hare Aplysia kurodai, and the absolute stereostructures of this material and macrosphelide H, previously undetermined, have been elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques and some chemical transformation. (R)-Methyl 3-p-bromobenzoyloxy-5-oxohexanoate has been synthesized for configurational assignments of macrosphelide H. These macrosphelides inhibited the adhesion of human-leukemia HL-60 cells to HUVEC.