A Monoacylglyceryltrimethylhomoserine, 21F121-A, Containing a Branched Acyl Group from Penicillium Glaucoroseum.

A new monoacylglyceryltrimethylhomoserine, 21F121-A (1), was isolated from the culture of Penicillium glaucoroseum (21F00121) by LCMS-guided purification. The structure was elucidated by NMR and mass spectrometries. The absolute configuration of the homoserine moiety was analyzed by the ECD spectrum after acid hydrolysis, and the S-configuration of the glycerol moiety was determined based on the spectrum of the 1,2-dibenzoyl derivative after acid hydrolysis. Although a variety of diacylglyceryltrimethylhomoserine is distributed in lower plants and fungi, a limited number of studies on monoacyl derivatives have been reported. This is the fourth sample of monoacylglyceryltrimethylhomoserine discovered from a natural source, and the second sample isolated from a fungus. Compound 1 contains an unusual branched pentaene chain attached at the sn-1 position of glycerol and weakly inhibited the growth of HCT116 cells.