New Isoquinoline Alkaloids from Paraphaeosphaeria sporulosa F03, a Fungal Endophyte Isolated from Paepalanthus planifolius

Author:

de Amorim Marcelo R.1,Paz Tiago A.1,Pinto Luciano da S.2,Hilário Felipe3,Zanini Camila L.4,Aguiar Anna Caroline C.4,Silva Débora E. S.1,Furlan Maysa1,Guido Rafael V. C.4,Bauab Taís M.3,Netto Adelino V. de G.1,dos Santos Lourdes C.1

Affiliation:

1. Institute of Chemistry, São Paulo State University (Unesp), Araraquara, SP, Brazil

2. Department of Chemistry, Federal University of São Carlos (UFSCar), São Carlos, SP, Brazil

3. School of Pharmaceutical Sciences, São Paulo State University (Unesp), Araraquara, SP, Brazil

4. São Carlos Institute of Physics, University of São Paulo (USP), São Carlos, SP, Brazil

Abstract

AbstractAs part of our continuing efforts to discover new bioactive compounds from endophytic fungal sources, we have investigated the extract of the Paraphaeosphaeria sporulosa F03 strain. The study led to the isolation of four new 3-methyl-isoquinoline alkaloids (1 – 4) and four known polyketides (5 – 8). The structures of compounds 1 – 4 were elucidated by 1D and 2D NMR experiments and HRMS analysis. The absolute configuration of 4 was determined by comparison of its experimental electronic circular dichroism spectrum with calculated data. Compounds 1 – 4 exhibited antifungal activity with minimal inhibitory concentration values ranging from 6.25 – 50 µg/mL against six Candida species but they did not present any cytotoxic activity against the human tumor cell lines A549 (lung), MCF-7 (breast), and HepG2 (hepatocellular). In addition, compound 4 exhibited antiplasmodial activity in the low micromolar range (IC50 = 4 µM).

Funder

Fundação de Amparo à Pesquisa do Estado de São Paulo

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Complementary and alternative medicine,Drug Discovery,Pharmaceutical Science,Pharmacology,Molecular Medicine,Analytical Chemistry

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