Constituents of Chinese Piper species and their inhibitory activity on prostaglandin and leukotriene biosynthesis in vitro.

The n-hexane extracts of 19 Piper species, predominantly from China, were screened for their 5-lipoxygenase (5-LOX) and cyclooxygenase-1 (COX-1) inhibitory potential. Many of them showed considerable inhibitory activity against at least one of these two key enzymes of the arachidonic acid metabolism, especially against COX-1. The best results in inhibiting the formation of leukotrienes were obtained with the extract of Piper kadsura. In the terms of prostaglandin synthesis inhibition, the extract of Piper boehmeriifolium var. tonkinense was found to have the strongest activity. Furthermore, an analytical investigation by means of TLC, HPLC-DAD and GC-MS resulted in the identification of 20 constituents. Most of them were amides with an interesting variety of amine moieties. Among them were pellitorine, and four higher homologues, piperlonguminine, dihydropiperlonguminine, futoamide, chingchengenamide, the retrofractamides A, B and D, guineensine, brachystamide B, piperanine, piperine, piperdardine, sarmentine, pipataline and benzylbenzoate. In 96 cases, these constituents were new for the particular plant.

Isobutylamides and a new methylbutylamide from Piper sarmentosum.

A homologous series of six 2 E,4 E-diene-isobutylamides and a new N-2'-methylbutyl-2 E,4 E-decadieneamide were isolated from the N-hexane extract of the aerial parts of PIPER SARMENTOSUM. While the crude extract was found to possess cyclooxygenase-1 (COX-1) and 5-lipoxygenase (5-LO) inhibitory activity (COX-1 IC (50) = 19 microg/ml; 5-LO IC (50) = 10 microg/ml), the isolated compounds showed only weak effects in both test systems.