1.Alcoholysis of naturally occurring imides: misleading interpretation of antifungal activities.
Pacher T1, Raninger A, Lorbeer E, Brecker L, But PP, Greger H. J Nat Prod. 2010 Aug 27;73(8):1389-93. doi: 10.1021/np1003092.
The frequent presence of the sulfur-containing amide penangin (10) in leaf extracts of Glycosmis species turned out to be the result of decomposition of imides generated by extraction and storage in MeOH. Reinvestigation of Glycosmis mauritiana and G. cf. puberula with acetone revealed the presence of six imides. In addition to penimides A (1) and B (2) and ritigalin (6), three new derivatives, krabin (4), isokrabin (5), and methoxypenimide B (3), were isolated and identified by spectroscopic methods. All six imides were shown to be susceptible to different rates of methanolic cleavage, leading to their corresponding methyl esters and sulfur-containing amides. Whereas the decomposition products penangin (10), isopenangin (11), and sinharin (14) are known, the corresponding cleavage of methyl N-methylthiocarbamate (7) from ritigalin (6), monitored in situ by (1)H NMR spectroscopy, is described here for the first time. Its structure was further confirmed by GC-MS coupling.