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. In addition, conformation for all the compounds has been discussed. Compounds 1-3 exhibited significant growth inhibition against tumour cell lines. Pericosine A 1 also showed significant in vivo tumour inhibitory activity. In addition, compound inhibited the protein kinase EGFR and topoisomerase II.
Yamada
Takeshi
T
Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan.
Iritani
Masashi
M
Ohishi
Hirohumi
H
Tanaka
Kayo
K
Minoura
Katsuhiko
K
Doi
Mitsunobu
M
Numata
Atsushi
A
D000818:Animals; D001048:Aplysia / Q000737:chemistry*; D001203:Ascomycota / Q000145:classification / Q000187:drug effects*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy*; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured / Q000187:drug effects
C523077:methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate; C496389:pericosine B; D012765:Shikimic Acid