Indole alkaloids from the leaves of Ravenia spectabilis engl. with activity against pancreatic cancer cell line

Abstract

Two previously undescribed indole alkaloids, 3-prenyl-5(3-keto-but-1-enyl) indole and 3-prenyl-indole-5-carbaldehyde, the structurally-related 3,5-diprenyl indole and four known alkaloids were isolated from the leaves of Ravenia spectabilis Engl. Structures were elucidated based on nuclear magnetic resonance (1D and 2D NMR) spectroscopic and mass spectrometric analysis. The previously undescribed compounds isolated were subsequently screened against the HeLa (human cervical cancer), MIA PaCa-2 (human pancreatic adenocarcinoma) and A549 (lung cancer) cell lines. Among the isolated compounds, 3,5-diprenyl indole was the most cytotoxic across all three cell lines (MIA PaCa-2 IC50 = 9.5 ± 2.2 μM). Molecular modelling studies suggested DNA intercalation as the mode of action of these compounds.