Stereochemical determination and bioactivity assessment of (S)-(+)-curcuphenol dimers isolated from the marine sponge Didiscus aceratus and synthesized through laccase biocatalysis
| Autor: | Jocelyn R. Flanary, Xiaolin Cao, Victor Kenyon, Peter Rygaard Lassen, Robert H. Cichewicz, Theodore R. Holman, Phillip Crews, Laura J. Clifford, Teresa B. Freedman, Joshua D. Deschamps, Laurence A. Nafie |
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| Rok vydání: | 2005 |
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Molecular Spectrometry Mass Electrospray Ionization Magnetic Resonance Spectroscopy Stereochemistry Metabolite Electrospray ionization Clinical Biochemistry Molecular Conformation Pharmaceutical Science Ether Crystallography X-Ray Biochemistry Catalysis chemistry.chemical_compound Structure-Activity Relationship Cell Line Tumor Drug Discovery Organic chemistry Animals Humans Phenols Lipoxygenase Inhibitors Molecular Biology Cell Proliferation Organic Chemistry Laccase Absolute configuration Stereoisomerism Porifera chemistry Axial chirality Biocatalysis Molecular Medicine Enantiomer Drug Screening Assays Antitumor Dimerization Sesquiterpenes |
| Zdroj: | Bioorganicmedicinal chemistry. 13(19) |
| ISSN: | 0968-0896 |
| Popis: | Electrospray ionization mass spectrometry-guided isolation of extracts from Didiscus aceratus led to the discovery of several new derivatives of the bioactive bisabolene-type sponge metabolite (S)-(+)-curcuphenol (1). The compounds obtained by this method included a mixture of known (2) and new (3) dihydroxylated analogs as well as a novel family of dimeric derivatives, dicurcuphenols A-E (4-8), and dicurcuphenol ether F (9). Dimers 4-9 were also subsequently obtained through a hemisynthetic method in which 1 was incubated with the enzyme laccase. Atropisomeric dimers 5 and 6 were subjected to vibrational circular dichroism analysis thereby establishing their absolute biaryl axial chirality as P and M, respectively. In contrast to 1, metabolites 2-9 exhibited weak or no cytotoxic or lipoxygenase inhibitory effects. |
| Databáze: | OpenAIRE |
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