RESUMEN
A chiral derivatization strategy with phenylglycine methyl ester (PGME) was employed to develop a straightforward method to determine the absolute configurations of N,N-dimethyl amino acids. The PGME derivatives were analyzed using liquid chromatography-mass spectrometry to identify the absolute configurations of various N,N-dimethyl amino acids based on their elution time and order. The established method was applied to assign the absolute configuration of the N,N-dimethyl phenylalanine in sanjoinine A (4), a cyclopeptide alkaloid isolated from Zizyphi Spinosi Semen widely used as herbal medicine for insomnia. Sanjoinine A displayed production of nitric oxide (NO) in LPS-activated RAW 264.7 cells.
RESUMEN
The anti-melanogenic activity of 259 actinomycete strains was tested, and based on the results for the inhibition of mushroom tyrosinase activity and the reduction in melanin content, Micromonospora sp. JCS1 and JCS7 were selected as the strains with the highest anti-melanogenic potential. The activity-guided fractionation of extracts from JCS1 and JCS7 led to the isolation of the dipeptides cyclo(L-Phenyl alanine (Phe)-L-Proline (Pro)) (1) and cyclo(L-Tryptophan (Trp)-L-Proline (Pro)) (2). These two compounds were tested for their inhibition of mushroom tyrosinase by monitoring L-DOPA levels and melanin production. Cyclo(L-Phe-L-Pro) (1) and cyclo(L-Trp-L-Pro) (2) were thus confirmed to have the potential for use in functional whitening cosmetics containing actinomycete-derived secondary metabolites.