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STRUCTURE-BASED MOLECULAR NETWORKING FOR THE TARGET DISCOVERY OF OXAHOMOAPORPHINE AND 8-OXOHOMOAPORPHINE ALKALOIDS FROM DUGUETIA SURINAMENSIS
Paz, Weider H. P. et al. | Date Issued: 2019
Author
Paz, Weider H. P.
Oliveira, Rodolfo N. de
Heerdt, Gabriel
Angolini, Célio F. F.
Medeiros, Lívia S. de
Silva, Valdenizia Rodrigues
Santos, Luciano de Souza
Soares, Milena Botelho Pereira
Bezerra, Daniel Pereira
Morgon, Nelson H.
Almeida, Jackson Moura Araujo da
Silva, Felipe Moura Araujo da
Costa, Emmanoel Vilaça
Koolen, Héctor Henrique Ferreira
Affilliation
Amazonas State University. Metabolomics and Mass Spectrometry Research Group. Manaus, AM, Brazil / Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil.
Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil.
Federal University of Minas Gerais. Department of Chemistry. Belo Horizonte, MG, Brazil.
Federal University of ABC. Center of Human and Natural Sciences. Santo André, SP, Brazil.
Federal University of São Paulo. Department of Chemistry. Diadema, SP, Brazil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.
University of Campinas. Institute of Chemistry. Campinas, SP, Brazil.
Federal University of Vale do São Francisco. Center for Study and Research of Medicinal Plants. Petrolina, PE, Brazil.
Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil.
Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil.
Amazonas State University. Metabolomics and Mass Spectrometry Research Group. Manaus, AM, Brazil.
Abstract
In addition to seven known alkaloids (2, 6-11) and 1,2,4-trimethoxybenzene (1), three isoquinoline-derived alkaloids (3-5), namely, duguetinine (3), a compound based on an unprecedented oxahomoaporphine scaffold, and two new 8-oxohomoaporphine alkaloids, duguesuramine (4) and 11-methoxyduguesuramine (5), and a new asarone-derived phenylpropanoid (10) were isolated from the bark of Duguetia surinamensis. The isolation workflow was guided by HPLC-HRESIMS/MS and molecular networking-based analyses. Twenty-four known alkaloids were dereplicated from the D. surinamensis alkaloid-rich fraction network and were assigned by manual MS/MS interpretation. Their cytotoxic potential was evaluated.
Keywords in Portuguese
Alcaloides
Annonaceae
Amazonia
Floresta Tropical
 
Keywords
Alkaloids
Annonaceae
Amazonian Ecosystem
Rainforest
 
Publisher
American Society of Pharmacognosy
Citation
PAZ, Weider H. P. et al. Structure-Based Molecular Networking for the Target Discovery of Oxahomoaporphine and 8-Oxohomoaporphine Alkaloids from Duguetia surinamensis. Journal of Natural Products, v. 82, p. 2220−2228, 2019.
DOI
10.1021/acs.jnatprod.9b00287
ISSN
0163-3864