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Macrophilone A: Structure Elucidation, Total Synthesis, and Functional Evaluation of a Biologically Active Iminoquinone from the Marine Hydroid Macrorhynchia philippina.

ABSTRACT: A previously uncharacterized pyrroloiminoquinone natural product, macrophilone A, was isolated from the stinging hydroid Macrorhynchia philippina. The structure was assigned utilizing long-range NMR couplings and DFT calculations and proved by a concise, five-step total synthesis. Macrophilone A and a synthetic analogue displayed potent biological activity, including increased intracellular reactive oxygen species levels and submicromolar cytotoxicity toward lung adenocarcinoma cells.

SUBMITTER: Zlotkowski K

PROVIDER: S-EPMC6318790 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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Macrophilone A: Structure Elucidation, Total Synthesis, and Functional Evaluation of a Biologically Active Iminoquinone from the Marine Hydroid Macrorhynchia philippina.

Zlotkowski Katherine K Hewitt William M WM Yan Pengcheng P Bokesch Heidi R HR Peach Megan L ML Nicklaus Marc C MC O'Keefe Barry R BR McMahon James B JB Gustafson Kirk R KR Schneekloth John S JS

Organic letters 20170327 7

A previously uncharacterized pyrroloiminoquinone natural product, macrophilone A, was isolated from the stinging hydroid Macrorhynchia philippina. The structure was assigned utilizing long-range NMR couplings and DFT calculations and proved by a concise, five-step total synthesis. Macrophilone A and a synthetic analogue displayed potent biological activity, including increased intracellular reactive oxygen species levels and submicromolar cytotoxicity toward lung adenocarcinoma cells. ...[more]

PMID: 28345939

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