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

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.

PAZ, WEIDER H. P. ; DE OLIVEIRA, RODOLFO N. ; HEERDT, GABRIEL ; Angolini, Célio F. F. ; S. DE MEDEIROS, LÍVIA ; SILVA, VALDENIZIA R. ; SANTOS, LUCIANO S. ; SOARES, MILENA B. P. ; BEZERRA, DANIEL P. ; MORGON, NELSON H. ; ALMEIDA, JACKSON R. G. S. ; DA SILVA, FELIPE M. A. ; COSTA, EMMANOEL V. ; KOOLEN, HECTOR H. F. JOURNAL OF NATURAL PRODUCTS, 2019. http://dx.doi.org/10.1021/acs.jnatprod.9b00287