Evidence map›Paper›PMID 27933896›Full record

ArticleJournal of natural products2016

Total Synthesis and in Vitro Anti-Tumor-Promoting Activities of Racemic Acetophenone Monomers from Acronychia trifoliolata.

Chihiro Morita, Yukiko Kobayashi, Yohei Saito, Katsunori Miyake, Harukuni Tokuda, Nobutaka Suzuki, Eiichiro Ichiishi, Kuo-Hsiung Lee, Kyoko Nakagawa-Goto

Abstract read
In one paragraph

Article in Journal of natural products, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
0.9field-weighted citation impact, top 23% of its field
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

2 citing papers in PubMed, 15 citations in OpenAlex.

  1. Prenylated Acetophloroglucinol Dimers fromJournal of natural products · 2019
    Article
  2. Acetophenone Monomers from Acronychia trifoliolata.Journal of natural products · 2016
    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

9 authors at 4 institutions in 3 countries.

Chihiro Morita
Yukiko Kobayashi
Yohei Saito
Katsunori Miyake
Harukuni TokudaOrganic Chemistry in Life Science, Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University , Kyoto 606-8502, Japan.
Nobutaka Suzuki
Eiichiro IchiishiInternational Health & Welfare University Hospital , Nasushiobara, Tochigi 329-2763, Japan.
Kuo-Hsiung LeeNatural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-7568, United States.
Kyoko Nakagawa-GotoNatural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-7568, United States.
Kanazawa University · JPUniversity of North Carolina at Chapel Hill · USInternational University of Health and Welfare · JPKyoto University · JP

Funding

Novel Antitumor AgentsR01CA177584 · NCI · UNIV OF NORTH CAROLINA CHAPEL HILL · PI LEE, KUO-HSIUNG · 2013 to 2017
$1.9M
NCI NIH HHS R01 CA177584
6 · The paper itself

Abstract

Six acetophenone derivatives, acronyculatins I (1), J (2), K (3), L (4), N (5), and O (6), were recently isolated from Acronychia trifoliolata, and the structure of the known acronyculatin B (7) was revised. Because of the limited quantities of isolated products as well as their structure similarity, racemic acronyculatins I-L, N, O, and B (1-7) were synthesized to confirm their structures and to obtain sufficient material for biological evaluation. Trihydroxyacetophenone was converted to the target compounds by various sequences of hydroxy group protection, allylation or prenylation, and epoxidation followed by cyclization. C-Prenylations were carried out by direct addition of a prenyl group or through 1,3- or 3,3-sigmatropic rearrangement. The synthesized racemic compounds were evaluated in an anti-tumor-promoting assay using the Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate in Raji cells. All tested compounds significantly inhibited EBV-EA activation. Especially, racemic acronyculatin I (1) displayed the most potent inhibitory effects, with an IC

Indexed as

AcetophenonesAntigens, ViralCarcinogensHerpesvirus 4, HumanHumansMolecular StructureNeoplasmsRutaceaeStereoisomerismStructure-Activity RelationshipTetradecanoylphorbol AcetateAcetophenonesAntigens, ViralCarcinogensEpstein-Barr virus early antigenTetradecanoylphorbol Acetate

Identifiers

PMID27933896
PMCPMC5503185
OpenAlexW2554348562

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

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.