Pericosines, antitumour metabolites from the sea hare-derived fungus Periconia byssoides. Structures and biological activities.

Pericosines A-E 1-5 have been isolated from a strain of Periconia byssoides originally separated from the sea hare Aplysia kurodai. Among them, pericosines C 3 and E 5 were separated as enantiomeric mixtures. Their stereostructures, except for compound 1, have been elucidated or identified on the basis of spectroscopic analyses, including 1D and 2D NMR techniques, and X-ray analysis.

Peribysins A-D, potent cell-adhesion inhibitors from a sea hare-derived culture of Periconia species.

Peribysins A-D 1-4, including a new type of furanofuran, have been isolated from a strain of Periconia byssoides originally separated from the sea hare Aplysia kurodai, and their relative stereostructures have been elucidated on the basis of NMR spectral analyses. All these metabolites potently inhibited the adhesion of human-leukemia HL-60 cells to HUVEC. The activity of compound 4, exhibiting the most potent inhibitory activity, was 380 times as potent as herbimycin A (standard).

Absolute stereostructures of cell adhesion inhibitors, macrosphelides H and L, from Periconia byssoides OUPS-N133.

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.