Elucidation of the Relationship between CD Cotton Effects and the Absolute Configuration of Sixteen Stereoisomers of Spiroheterocyclic-Lactams

As part of research to search for antitumor agents in fungi originating from marine organisms, cephalimysins E–L were isolated from a culture broth of Aspergillus fumigatus that was separated from the marine fish Mugil cephalus. One- and two-dimensional nuclear magnetic resonance spectra r...

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Bibliographic Details
Main Authors: Takeshi Yamada, Tetsuya Kajimoto, Takashi Kikuchi, Reiko Tanaka
Format: Article
Language:English
Published: MDPI AG 2018-06-01
Series:Marine Drugs
Subjects:
Online Access:http://www.mdpi.com/1660-3397/16/7/223
Description
Summary:As part of research to search for antitumor agents in fungi originating from marine organisms, cephalimysins E–L were isolated from a culture broth of Aspergillus fumigatus that was separated from the marine fish Mugil cephalus. One- and two-dimensional nuclear magnetic resonance spectra revealed their planar structures, which are diastereomers of each other. Their absolute stereostructures were established by epimerization at C-8 with acidic methanol, nuclear Overhauser effect spectroscopy (NOESY), and circular dichroism (CD) spectroscopy. These demonstrated the detailed relationships between absolute configuration and CD Cotton effects. Additionally, in the growth inhibition assay against P388, HL-60, L1210, and KB cell lines, some of the fungal metabolites or reaction products exhibited moderate activities.
ISSN:1660-3397