Evidence map›Paper›PMID 28345939›Full record

ArticleOrganic letters2017

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

Katherine Zlotkowski, William M Hewitt, Pengcheng Yan, Heidi R Bokesch, Megan L Peach, Marc C Nicklaus, Barry R O'Keefe, James B McMahon, Kirk R Gustafson, John S Schneekloth

Abstract read
In one paragraph

Article in Organic letters, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.

0numbers the graph read from it
0cells of the map it votes in
10citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

10 citing papers in PubMed.

  1. Thiazination ofOrganic chemistry frontiers : an international journal of organic chemistry · 2026
    Article
  2. Review
  3. Review
  4. Article
  5. Marine Pyrrole Alkaloids.Marine drugs · 2021
    Review
  6. Current Status of SUMOylation Inhibitors.Current medicinal chemistry · 2021
    Review
  7. Article
  8. Review
  9. Article
  10. Crystal structure of (Acta crystallographica. Section E, Crystallographic communications · 2018
    Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

10 authors.

Katherine Zlotkowski
William M Hewitt
Pengcheng YanSchool of Pharmaceutical Sciences, Wenzhou Medical University , Wenzhou, Zhejiang 325035, People's Republic of China.
Heidi R BokeschBasic Science Program, Leidos Biomedical Research, Inc., Frederick National Laboratory for Cancer Research, Frederick, Maryland 21702, United States.
Megan L PeachBasic Science Program, Leidos Biomedical Research, Inc., Frederick National Laboratory for Cancer Research, Frederick, Maryland 21702, United States.
Marc C Nicklaus
Barry R O'Keefe
James B McMahon
John S SchneeklothORCID 0000-0001-7459-783X

Funding

In Silico Screening for Cancer TargetsZICBC010639 · NCI · DIVISION OF BASIC SCIENCES - NCI · PI NICKLAUS, MARC · 2009 to 2024
$4.2M
Identification of Inhibitors of Protein SumoylationZIABC011449 · NCI · DIVISION OF BASIC SCIENCES - NCI · PI SCHNEEKLOTH, JOHN · 2012 to 2019
$4.2M
CCR NIH HHS HHSN261200800001CIntramural NIH HHS Z99 CA999999NCI NIH HHS HHSN261200800001E
6 · The paper itself

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.

Indexed as

Biological ProductsMolecular StructureQuinonesReactive Oxygen SpeciesBiological ProductsiminoquinoneQuinonesReactive Oxygen Species

Identifiers

PMID28345939
PMCPMC6318790

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Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.