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United States Department of Agriculture

Agricultural Research Service

Research Project: CHEMISTRY OF NATURAL PRODUCTS FOR PEST MANAGEMENT AND CROP DEVELOPMENT

Location: Natural Products Utilization Research

Title: The Raputindoles: Novel Cyclopentyl Bisindole Alkaloids from Raputia simulans

Authors
item Vougogiannopoulou, Konstantina -
item Fokialakis, Nikolas -
item Aligiannis, Nektarios -
item Cantrell, Charles
item Skaltsounis, Alexios-Leandro -

Submitted to: Organic Letters
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: February 15, 2010
Publication Date: April 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.

Last Modified: 4/24/2014