Indole alkaloids from the roots of Isatis indigotica and their inhibitory effects on nitric oxide production

Three rare indole-2-S-glycosides, indole-3-acetonitrile-2-S-ss-D-glucopyranoside (1), indole-3-acetonitrile-4-methoxy-2-S-ss-D-glucopyranoside (2) and N-methoxy-indole-3-acetonitrile-2-S-ss-D-glucopyranoside (3), together with 11 known indole alkaloids were isolated from the roots of Isatis indigotica Fort. (Cruciferae). The structures of 1-3 were elucidated on the basis of mass spectrometry and extensive 1D and 2D NMR spectroscopy. All of the isolated compounds were tested for inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages. A plausible biosynthesis pathway of 1-3 is also proposed. (C) 2014 Elsevier B.V. All rights reserved.