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Open AccessArticle

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

1
Department of Medicinal Molecular Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan
2
Medicinal Organic Chemistry Laboratory, College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1, Nojihigshi, Kusatsu, Shiga 525-8577, Japan
*
Author to whom correspondence should be addressed.
Mar. Drugs 2018, 16(7), 223; https://doi.org/10.3390/md16070223
Received: 12 June 2018 / Revised: 24 June 2018 / Accepted: 27 June 2018 / Published: 29 June 2018
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. View Full-Text
Keywords: cephalimysins; Aspergillus fumigatus; marine microorganism; Mugil cephalus; spiro-heterocyclic γ-lactam; circular dichroism spectroscopy; cytotoxicity cephalimysins; Aspergillus fumigatus; marine microorganism; Mugil cephalus; spiro-heterocyclic γ-lactam; circular dichroism spectroscopy; cytotoxicity
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Yamada, T.; Kajimoto, T.; Kikuchi, T.; Tanaka, R. Elucidation of the Relationship between CD Cotton Effects and the Absolute Configuration of Sixteen Stereoisomers of Spiroheterocyclic-Lactams. Mar. Drugs 2018, 16, 223.

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