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

Autor: Paz WHP; Metabolomics and Mass Spectrometry Research Group , Amazonas State University , Manaus 690065-130 , Brazil.; Department of Chemistry , Federal University of Amazonas , Manaus 69077-000 , Brazil., de Oliveira RN; Department of Chemistry , Federal University of Amazonas , Manaus 69077-000 , Brazil., Heerdt G; Department of Chemistry , Federal University of Minas Gerais , Belo Horizonte 31270-901 , Brazil., Angolini CFF; Center of Human and Natural Sciences , Federal University of ABC , 09210-580 Santo André , Brazil., S de Medeiros L; Department of Chemistry , Federal University of São Paulo , 09920-540 Diadema , Brazil., Silva VR; Gonçalo Moniz Institute , Oswaldo Cruz Foundation , Salvador 40296-710 , Brazil., Santos LS; Gonçalo Moniz Institute , Oswaldo Cruz Foundation , Salvador 40296-710 , Brazil., Soares MBP; Gonçalo Moniz Institute , Oswaldo Cruz Foundation , Salvador 40296-710 , Brazil., Bezerra DP; Gonçalo Moniz Institute , Oswaldo Cruz Foundation , Salvador 40296-710 , Brazil., Morgon NH; Institute of Chemistry , University of Campinas , Campinas 13083-970 , Brazil., Almeida JRGS; Center for Study and Research of Medicinal Plants , Federal University of Vale do São Francisco , Petrolina 56304-205 , Brazil., da Silva FMA; Department of Chemistry , Federal University of Amazonas , Manaus 69077-000 , Brazil., Costa EV; Department of Chemistry , Federal University of Amazonas , Manaus 69077-000 , Brazil., Koolen HHF; Metabolomics and Mass Spectrometry Research Group , Amazonas State University , Manaus 690065-130 , Brazil.
Jazyk: angličtina
Zdroj: Journal of natural products [J Nat Prod] 2019 Aug 23; Vol. 82 (8), pp. 2220-2228. Date of Electronic Publication: 2019 Aug 12.
DOI: 10.1021/acs.jnatprod.9b00287
Abstrakt: 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.
Databáze: MEDLINE