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Org Lett. 2017 Apr 7;19(7):1726-1729. doi: 10.1021/acs.orglett.7b00496. Epub 2017 Mar 27.

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

Author information

1
School of Pharmaceutical Sciences, Wenzhou Medical University , Wenzhou, Zhejiang 325035, People's Republic of China.
2
Basic Science Program, Leidos Biomedical Research, Inc., Frederick National Laboratory for Cancer Research, Frederick, Maryland 21702, United States.

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.

PMID:
28345939
PMCID:
PMC6318790
DOI:
10.1021/acs.orglett.7b00496
[Indexed for MEDLINE]
Free PMC Article

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