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

Author(s): Brian Iritani, A Numata, Mitsunobu Doi, Takeshi Yamada, K Tanaka, Katsuhiko Minoura, H Ohishi

Publication date: 2007-12-21

Journal: Organic & Biomolecular Chemistry

Keywords: Animals, Aplysia, chemistry, Ascomycota, classification, drug effects, Humans, Magnetic Resonance Spectroscopy, Molecular Conformation, Molecular Structure, Neoplasms, drug therapy, Shikimic Acid, analogs & derivatives, pharmacology, Spectrometry, Mass, Electrospray Ionization, Spectrophotometry, Ultraviolet, Spectroscopy, Fourier Transform Infrared, Stereoisomerism, Tumor Cells, Cultured

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Abstract

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.