Evidence map›Paper›PMID 22384985›Full record

ArticleThe Journal of organic chemistry2012

Erythrolic acids A-E, meroterpenoids from a marine-derived Erythrobacter sp.

Youcai Hu, Aaron G Legako, Ana Paula D M Espindola, John B MacMillan

Abstract read
In one paragraph

Article in The Journal of organic chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.

0numbers the graph read from it
0cells of the map it votes in
9citing papers in PubMed
3.0field-weighted citation impact, top 10% 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

9 citing papers in PubMed, 27 citations in OpenAlex.

  1. Bacterial terpenome.Natural product reports · 2021
    Review
  2. Article
  3. Genomic-based taxonomic classification of the familyInternational journal of systematic and evolutionary microbiology · 2020
    Article
  4. Review
  5. Metabolites Produced by the Oral Commensal BacteriumInternational journal of molecular sciences · 2020
    Article
  6. Review
  7. 3 Biotech · 2019
    Article
  8. Article
  9. 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

4 authors at 1 institution in 1 country.

Youcai HuDepartment of Biochemistry, Division of Chemistry, University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, USA.
Aaron G Legako
Ana Paula D M Espindola
John B MacMillan
The University of Texas Southwestern Medical Center · US

Funding

Structure guided discovery of small molecule antagonists of Smac (DIABLO)/XIPAP01CA095471 · NCI · UT SOUTHWESTERN MEDICAL CENTER · PI MCKNIGHT, STEVEN L · 2002 to 2011
$34.1M
Marine Actinomycetes as a Resource for Anticancer Natural ProductsR01CA149833 · NCI · UT SOUTHWESTERN MEDICAL CENTER · PI MACMILLAN, JOHN B · 2010 to 2014
$1.6M
NCI NIH HHS P01 CA095471NCI NIH HHS R01 CA149833
6 · The paper itself

Abstract

Erythrolic acids A-E (1-5) are five unusual meroterpenoids isolated from the bacterium Erythrobacter sp. derived from a marine sediment sample collected in Galveston, TX. The structures were elucidated by means of detailed spectroscopic analysis and chemical derivatization. The erythrolic acids contain a 4-hydroxybenzoic acid appended with a modified terpene side chain. The side-chain modifications include oxidation of a terminal methyl substituent and in the case of 1-4 addition of a two-carbon unit to give terpene side chains of unusual length: C22 for 1 and 2, C17 for 3, and C12 for 4. The relative and absolute configurations of the meroterpenoids were determined by coupling constant, NOE, and Mosher's analysis. In vitro cytotoxicity toward a number of nonsmall cell lung cancer (NSCLC) cell lines revealed only modest activity for erythrolic acid D (4) (2.5 μM against HCC44). The discovery of these unusual diterpenes, along with the previously reported erythrazoles, demonstrates the natural product potential of a previously unstudied group of bacteria for drug discovery. The unusual nature of the terpene side chain, we believe, involves an oxidation of a terminal methyl group to a carboxylic acid and subsequent Claisen condensation with acetyl-CoA.

Indexed as

Carcinoma, Non-Small-Cell LungDrug Screening Assays, AntitumorHumansMolecular StructureParabensSphingomonadaceaeTerpenes4-hydroxybenzoic acidParabensTerpenes

Identifiers

PMID22384985
PMCPMC3321083
OpenAlexW1971569505

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.