Absolute stereostructures of cell-adhesion inhibitors, macrosphelides C, E–G and I, produced by a Periconia species separated from an Aplysia sea hare

Abstract

Macrosphelides E-I have been isolated, along with known macrosphelides A and C, from a strain of Periconia byssoides originally separated from the sea hare Aplysia kurodai, and the absolute stereostructures of macrosphelides E-G and I have been elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques and some chemical transformations. In addition, the absolute configuration of macrosphelide C, previously undetermined, has been established by X-ray analysis and application of the modified Mosher method. Macrosphelides E-H inhibited the adhesion of human-leukaemia HL-60 cells to HUVEC.

Absolute Stereostructures of Cell-adhesion Inhibitors, Peribysins A, E, F and G, Produced by a Sea Hare-derived Periconia sp.

“…As reported previously [4], the AcOEt extract (5.7 g) of the culture filtrate was successively chromatographed on Sephadex LH-20 (CH 2 Cl 2 -MeOH, 1 : 1) and silica gel (CH 2 Cl 2 /MeOH). The MeOH -CH 2 Cl 2 (2 : 98) eluate (172.6 mg) from silica gel column chromatography was purified by HPLC using MeOH -H 2 O (7 : 3) as the eluent to afford 1 (17.8 mg, 0.31%).…”

“…As part of this study, we have previously isolated the cell-adhesion inhibitors, macrosphelides EϳI, L [4,5] and peribysins A (4)ϳD [6], from a strain of Periconia byssoides OUPS-N133 originally separated from the sea hare Aplysia kurodai. All of these compounds except for macrosphelide I inhibited the adhesion of human-leukemia HL-60 cells to human-umbilical-vein endothelial cells (HUVEC) more potently than herbimycin A [7,8].…”

Cell-adhesion Inhibitors Produced by a Sea Hare-derived Periconia sp.

“…As part of this study, we have previously isolated the cell-adhesion inhibitors, macrosphelides EϳI, L [4,5] and peribysins AϳI [6ϳ8], from a strain of Periconia byssoides OUPS-N133 originally isolated from the sea hare Aplysia kurodai. All of these compounds, except for macrosphelide I, inhibited the adhesion of human-leukemia HL-60 cells to human-umbilical-vein endothelial cells (HUVEC) more potently than herbimycin A [9,10].…”

Cell-adhesion Inhibitors Produced by a Sea Hare-derived Periconia sp. II

“…As reported previously [4], the AcOEt extract (5.7 g) of the culture filtrate was successively chromatographed on Sephadex LH-20 (CH 2 Cl 2 -MeOH, 1 : 1) and silica gel (CH 2 Cl 2 / MeOH). The MeOH -CH 2 Cl 2 (5 : 95) eluate (214.6 mg) from silica gel column chromatography was purified by HPLC using MeOH -H 2 O (7 : 3) as the eluent to afford 1 (7.8 mg, 0.14%) and 2 (10.2 mg, 0.18%).…”

“…As part of this study, we have previously isolated the cell-adhesion inhibitors, macrosphelides EϳI, L [4,5] and peribysins AϳG [6,7], from a strain of Periconia byssoides OUPS-N133 originally separated from the sea hare Aplysia kurodai. All of these compounds except for macrosphelide I inhibited the adhesion of human-leukemia HL-60 cells to humanumbilical-vein endothelial cells (HUVEC) more potently than herbimycin A [8,9].…”