Sistema FMUSP-HC: Faculdade de Medicina da Universidade de São Paulo (FMUSP) e Hospital das Clínicas da FMUSPSANTOS, Mario F. C.HARPER, Philip M.WILLIAMS, David E.MESQUITA, Juliana T.PINTO, Erika G.COSTA-SILVA, Thais A. daHAJDU, EduardoFERREIRA, Antonio G.SANTOS, Raquel A.MURPHY, Patrick J.ANDERSEN, Raymond J.TEMPONE, Andre G.BERLINCK, Roberto G. S.2015-10-262015-10-262015JOURNAL OF NATURAL PRODUCTS, v.78, n.5, p.1101-1112, 20150163-3864https://observatorio.fm.usp.br/handle/OPI/12032HPLC-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).engrestrictedAccesscrambe-crambeptilomycalin-aantimalarial activitynatural-productsbiemna-labouteibatzelladine-frevisionpulchrastereochemistryunguiferaarticleCopyright AMER CHEMICAL SOC10.1021/acs.jnatprod.5b00070Plant SciencesChemistry, MedicinalPharmacology & Pharmacy1520-6025