Submitted to: Organic Letters
Publication Type: Peer reviewed journal
Publication Acceptance Date: 2/15/2010
Publication Date: 4/15/2010
Citation: Vougogiannopoulou, K., Fokialakis, N., Aligiannis, N., Cantrell, C.L., Skaltsounis, A. 2010. The Raputindoles: Novel Cyclopentyl Bisindole Alkaloids from Raputia simulans. Organic Letters. 12(9):1908-1911. Interpretive Summary: Indole alkaloids comprise a large number of diverse metabolites originating from natural sources. The simplicity of the basic indole skeleton has been inspiring pharmaceutical chemists for over a century and its versatility has made the indole moiety a useful tool in organic chemistry. The indole core is highly reactive therefore indole alkaloids possess a variety of biological activities such as antimalarial, antiviral and antitumor. In the current study we report the isolation and structural characterization of raputindoles A-C, four novel bisindole alkaloids with a fused cyclopentyl unit deriving from isoprene.
Technical Abstract: A novel class of bisindole alkaloids is established by the isolation and structural determination of Raputindoles A-D (1-4) from the Amazonian plant Raputia simulans Kallunki (Rutaceae). Complete spectroscopic characterization was accomplished by means of NMR spectroscopy and APCI (+) HRMS. Raputindoles A-D possess a cyclopentyl moiety fused on the benzene part of the indole ring, originating from the combination of prenylated indole monomers.