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Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula

Santos, M.F.C. and Harper, P.M. and Williams, D.E. and Mesquita, J.T. and Pinto, E.G. and da Costa-Villa, T.A. and Hajdu, E. and Ferreira, A.G. and Santos, R.A. and Murphy, P.J. and Anderson, R.J. and Tempone, A.G. and Berlinck, R.G.S. (2015) Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula. Journal of natural products, 78 (5). pp. 1101-1112. DOI: 10.1021/acs.jnatprod.5b00070

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Abstract

HPLC-UV-ELSD-MS-guided fractionation of the anti-parasitic extract obtained from the marine sponge Monanchora arbuscula, collected off the southeastern coast of Brazil, led to the isolation of a series of guanidine and pyrimidine alkaloids. The pyrimidines monalidine A (1) and arbusculidine A (7), as well as the guanidine alkaloids batzellamide A (8) and hemibatzelladines 9�11, represent new minor constituents that were identified by analysis of spectroscopic data. The total synthesis of monalidine A confirmed its structure. Arbusculidine A (7), related to the ptilocaulin/mirabilin/netamine family of tricyclic guanidine alkaloids, is the first in this family to possess a benzene ring. Batzellamide A (8) and hemibatzelladines 9�11 represent new carbon skeletons that are related to the batzelladines. Evaluation of the anti-parasitic activity of the major known metabolites, batzelladines D (12), F (13), L (14), and nor-L (15), as well as of synthetic monalidine A (1), against Trypanosoma cruzi and Leishmania infantum is also reported, along with a detailed investigation of parasite cell-death pathways promoted by batzelladine L (14) and norbatzelladine L (15).

Item Type: Article
Subjects: Research Publications
Departments: College of Physical and Applied Sciences > School of Chemistry
Date Deposited: 29 May 2015 02:45
Last Modified: 23 Sep 2015 02:47
ISSN: 0163-3864
URI: http://e.bangor.ac.uk/id/eprint/4601
Identification Number: DOI: 10.1021/acs.jnatprod.5b00070
Publisher: American Chemical Society
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