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Pseudolaric acid B: NMR assignments, conformational analysis and cytotoxicity
Author(s) -
Hamburger Matthias O.,
Shieh HuiLing,
Zhou BingNan,
Pezzuto John M.,
Cordell Geoffrey A.
Publication year - 1989
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260271104
Subject(s) - chemistry , conformational isomerism , ring (chemistry) , lactone , molecule , stereochemistry , nuclear magnetic resonance spectroscopy , cytotoxicity , molecular conformation , nmr spectra database , proton nmr , two dimensional nuclear magnetic resonance spectroscopy , crystallography , spectral line , organic chemistry , in vitro , biochemistry , physics , astronomy
The proton and carbon spectra for the fertility‐regulating agent, pseudolaric acid B (1), have been assigned using a combination of one‐ and two‐dimensional NMR spectroscopic techniques. NOE difference measurements revealed an unexpected conformation of the molecule, which could only be explained by a strained conformation of the six‐membered lactone ring. Molecular forcefield calculations confirmed the presence of a low‐energy conformer having the lactone ring in a half‐planar conformation. The solution conformation is closely related to the solid‐state conformation. Evaluation in a broad range of human cell lines established that 1 is a general cytotoxic agent.