Protein tyrosine phosphatase 1B inhibitory components and a new unique N-alkylamide derivative with an endoperoxide bridge from aerial parts of Indonesian Spilanthes paniculata

Publication date: April 2018 Source:Phytochemistry Letters, Volume 24 Author(s): Delfly B. Abdjul, Hiroyuki Yamazaki, Wilmar Maarisit, Ryota Kirikoshi, Ohgi Takahashi, Fitje Losung, Magie M. Kapojos, Michio Namikoshi Research on protein tyrosine phosphatase (PTP) 1B inhibitors from terrestrial and marine natural resources identified N-isobutyl-2E-decenamide (1) and 3,4,5-tri-O-caffeoylquinic acid (2) as PTP1B inhibitory substances together with a new N-alkylamide (3) and two known congeners (4 and 5) from the aerial parts of Indonesian Spilanthes paniculata. The structure of 3 was elucidated as (2E, 7Z)-6,9-endoperoxy-N-2-methylbutyl-2,7-decadienamide based on its spectroscopic data. Compound 3 is a rare N-alkylamide derivative with an endoperoxide bridge, and only three natural products have been reported in this class. Compound 1 inhibited PTP1B activity with an IC50 value of 24 μM, whereas compound 2 exerted an inhibitory effect of 35% at 15 μM. This is the first study to report the inhibitory effects of an N-alkylamide derivative (1) on PTP1B activity. Graphical abstract

Source: Phytochemistry Letters - February 3, 2018 Category: Chemistry Source Type: research