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Pseudolaric acid B: NMR assignments, conformational analysis and cytotoxicity

✍ Scribed by Matthias O. Hamburger; Hui-Ling Shieh; Bing-Nan Zhou; John M. Pezzuto; Geoffrey A. Cordell

Publisher
John Wiley and Sons
Year
1989
Tongue
English
Weight
408 KB
Volume
27
Category
Article
ISSN
0749-1581

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✦ Synopsis

The proton and carbon spectra for the fertility-regulating agent, pseudolaric acid B (l), 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 lactooe ring. Molecular forcefield calculations confirmed the presence of a lowsnergy 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.

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