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

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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Reference:

Paz WHP, de Oliveira RN, Heerdt G, Angolini ClFF, S. de Medeiros Lv, Silva VR, Santos LS, Soares MBP, Bezerra DP, Morgon NH, Almeida JRGS, da Silva FMA, Costa EV and Koolen HHF. Structure-Based Molecular Networking for the Target Discovery of Oxahomoaporphine and 8-Oxohomoaporphine Alkaloids from Duguetia surinamensis. Journal of Natural Products. https://doi.org/10.1021/acs.jnatprod.9b00287



Keywords: Structure-Based Molecular Networking, Target Discovery, Oxahomoaporphine and 8-Oxohomoaporphine Alkaloids. Duguetia surinamensis, HPLC-HRESIMS/MS, Asarone-derived phenylpropanoids, 11-Methoxyduguesuramine, Duguesuramine, Duguetinine, 1,2,4-Trimethoxybenzene.

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