Absolute stereostructures of cell-adhesion inhibitors, peribysins A, E, F and G, produced by a sea hare-derived Periconia sp.
Peribysins E-G (1-3) have been isolated from a strain of Periconia byssoides originally separated from the sea hare Aplysia kurodai. Their absolute stereostructures 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 peribysin A (4), previously undetermined, has been established by conversion to 2 and 3. All these metabolites inhibited the adhesion of human-leukemia HL-60 cells to HUVEC.
Yamada
Takeshi
T
Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan. yamada@gly.oups.ac.jp
Doi
Mitsunobu
M
Miura
Atsuko
A
Harada
Waka
W
Hiramura
Mika
M
Minoura
Katsuhiko
K
Tanaka
Reiko
R
Numata
Atsushi
A
D000818:Animals; D001048:Aplysia / Q000382:microbiology; D001203:Ascomycota / Q000302:isolation & purification / Q000378:metabolism; D002448:Cell Adhesion / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D018360:Crystallography, X-Ray; D005663:Furans / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D007189:Indans / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
D005663:Furans; D007189:Indans; D009284:Naphthols; C492944:peribysin A; C501235:peribysin E; C501236:peribysin F; C501237:peribysin G