Structure elucidation and conformational properties of a novel bioactive clerodane diterpene using a combination of high field NMR spectroscopy, computational analysis and X-ray diffraction.
The structure of a novel CC clerodane type diterpenoid, namely (+)-19-acetoxy-cis-clerodan-3-ene-15-oic acid 1 was elucidated and its conformational properties were explored using a combination of high field NMR spectroscopy and computational analysis. The structural analysis provided results consistent with those obtained by a single X-ray diffraction study of its dicyclohexylammonium salt. The new clerodane type diterpene isolated in large quantities from Cistus monspeliensis L. leaves was found to exhibit significant antibacterial activity against Staphyloccoci (MIC50 = 0.085 mM) and therefore represents a promising lead compound. Interestingly the deacetylated derivative 2 of compound 1 was inactive.
Institute of Organic and Pharmaceutical Chemistry, National Hellenic Research Foundation, Athens, Greece.
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Kolocouris
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Mavromoustakos
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Demetzos
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Terzis
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Grdadolnik
D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D004224:Diterpenes / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D013210:Staphylococcus / Q000187:drug effects; D013329:Structure-Activity Relationship; D014961:X-Ray Diffraction
D000900:Anti-Bacterial Agents; D004224:Diterpenes