1. Academic Validation
  2. Structure-Based Molecular Networking for the Target Discovery of Oxahomoaporphine and 8-Oxohomoaporphine Alkaloids from Duguetia surinamensis

Structure-Based Molecular Networking for the Target Discovery of Oxahomoaporphine and 8-Oxohomoaporphine Alkaloids from Duguetia surinamensis

  • J Nat Prod. 2019 Aug 23;82(8):2220-2228. doi: 10.1021/acs.jnatprod.9b00287.
Weider H P Paz 1 2 Rodolfo N de Oliveira 2 Gabriel Heerdt 3 Célio F F Angolini 4 Lívia S de Medeiros 5 Valdenizia R Silva 6 Luciano S Santos 6 Milena B P Soares 6 Daniel P Bezerra 6 Nelson H Morgon 7 Jackson R G S Almeida 8 Felipe M A da Silva 2 Emmanoel V Costa 2 Hector H F Koolen 1
Affiliations

Affiliations

  • 1 Metabolomics and Mass Spectrometry Research Group , Amazonas State University , Manaus 690065-130 , Brazil.
  • 2 Department of Chemistry , Federal University of Amazonas , Manaus 69077-000 , Brazil.
  • 3 Department of Chemistry , Federal University of Minas Gerais , Belo Horizonte 31270-901 , Brazil.
  • 4 Center of Human and Natural Sciences , Federal University of ABC , 09210-580 Santo André , Brazil.
  • 5 Department of Chemistry , Federal University of São Paulo , 09920-540 Diadema , Brazil.
  • 6 Gonçalo Moniz Institute , Oswaldo Cruz Foundation , Salvador 40296-710 , Brazil.
  • 7 Institute of Chemistry , University of Campinas , Campinas 13083-970 , Brazil.
  • 8 Center for Study and Research of Medicinal Plants , Federal University of Vale do São Francisco , Petrolina 56304-205 , 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.

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