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Planta Med 2022; 88(12): 994-1003
DOI: 10.1055/a-1706-4642
Natural Product Chemistry and Analytical Studies
Original Papers

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

Marcelo R. de Amorim
1   Institute of Chemistry, São Paulo State University (Unesp), Araraquara, SP, Brazil
,
Tiago A. Paz
1   Institute of Chemistry, São Paulo State University (Unesp), Araraquara, SP, Brazil
,
Luciano da S. Pinto
2   Department of Chemistry, Federal University of São Carlos (UFSCar), São Carlos, SP, Brazil
,
Felipe Hilário
3   School of Pharmaceutical Sciences, São Paulo State University (Unesp), Araraquara, SP, Brazil
,
Camila L. Zanini
4   São Carlos Institute of Physics, University of São Paulo (USP), São Carlos, SP, Brazil
,
Anna Caroline C. Aguiar
4   São Carlos Institute of Physics, University of São Paulo (USP), São Carlos, SP, Brazil
,
Débora E. S. Silva
1   Institute of Chemistry, São Paulo State University (Unesp), Araraquara, SP, Brazil
,
Maysa Furlan
1   Institute of Chemistry, São Paulo State University (Unesp), Araraquara, SP, Brazil
,
Rafael V. C. Guido
4   São Carlos Institute of Physics, University of São Paulo (USP), São Carlos, SP, Brazil
,
Taís M. Bauab
3   School of Pharmaceutical Sciences, São Paulo State University (Unesp), Araraquara, SP, Brazil
,
Adelino V. de G. Netto
1   Institute of Chemistry, São Paulo State University (Unesp), Araraquara, SP, Brazil
,
Lourdes C. dos Santos
1   Institute of Chemistry, São Paulo State University (Unesp), Araraquara, SP, Brazil
› Author AffiliationsSupported by: Fundação de Amparo à Pesquisa do Estado de São Paulo 2013/07600-3
Supported by: Fundação de Amparo à Pesquisa do Estado de São Paulo 2015/04899-3
Supported by: Fundação de Amparo à Pesquisa do Estado de São Paulo 2015/11058-5
Supported by: Fundação de Amparo à Pesquisa do Estado de São Paulo 2016/17711-5
Supported by: Fundação de Amparo à Pesquisa do Estado de São Paulo 2020/01193-0
Supported by: Fundação de Amparo à Pesquisa do Estado de São Paulo 2020/12904-5
Supported by: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior Finance Code 001
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Abstract

As 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).

Key words

Isoquinoline - Endophytic fungus - Paraphaeosphaeria sporulosa - Paepalanthus planifolius - Eriocaulaceae

Supporting Information

    1D and 2D NMR spectra and HRMS analysis of the new compounds (1 – 4), chiral chromatographic analysis, calculated ECD spectrum of 4, and the proposed MS/MS fragmentation of compounds 1 – 4, 6, and 7 are available as Supporting Information.

  • Supporting Information


Publication History

Received: 17 May 2021

Accepted after revision: 21 November 2021

Article published online:
19 January 2022

© 2022. Thieme. All rights reserved.

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