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
  • 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.
PMID: 31403289 DOI: 10.1021/acs.jnatprod.9b00287
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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