title: 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.
authors.forename: Katherine
authors.initials: K
authors.lastname: Zlotkowski
authors.forename: William M
authors.initials: WM
authors.lastname: Hewitt
authors.affiliation: School of Pharmaceutical Sciences, Wenzhou Medical University , Wenzhou, Zhejiang 325035, People's Republic of China.
authors.forename: Pengcheng
authors.initials: P
authors.lastname: Yan
authors.affiliation: Basic Science Program, Leidos Biomedical Research, Inc., Frederick National Laboratory for Cancer Research, Frederick, Maryland 21702, United States.
authors.forename: Heidi R
authors.initials: HR
authors.lastname: Bokesch
authors.affiliation: Basic Science Program, Leidos Biomedical Research, Inc., Frederick National Laboratory for Cancer Research, Frederick, Maryland 21702, United States.
authors.forename: Megan L
authors.initials: ML
authors.lastname: Peach
authors.forename: Marc C
authors.initials: MC
authors.lastname: Nicklaus
authors.forename: Barry R
authors.initials: BR
authors.lastname: O'Keefe
authors.forename: James B
authors.initials: JB
authors.lastname: McMahon
authors.forename: Kirk R
authors.identifier: 0000-0001-6821-4943
authors.initials: KR
authors.lastname: Gustafson
authors.forename: John S
authors.identifier: 0000-0001-7459-783X
authors.initials: JS
authors.lastname: Schneekloth
mesh_terms: D001688:Biological Products; D015394:Molecular Structure; D011809:Quinones / Q000737:chemistry*; D017382:Reactive Oxygen Species
chemical_list: D001688:Biological Products; D011809:Quinones; D017382:Reactive Oxygen Species; C116897:iminoquinone