Evidence map›Paper›PMID 26259803›Full record

ArticleBioorganic & medicinal chemistry letters2015

Synthesis of oxygenated oleanolic and ursolic acid derivatives with anti-inflammatory properties.

Andrew T Nelson, Andrew M Camelio, Karin R Claussen, Jiyoon Cho, Lisa Tremmel, John DiGiovanni, Dionicio Siegel

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Bioorganic & medicinal chemistry letters, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.

0numbers the graph read from it
0cells of the map it votes in
15citing 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

15 citing papers in PubMed.

  1. Review
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  8. Review
  9. A Pentacyclic Triterpene fromACS chemical neuroscience · 2020
    Article
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  11. Article
  12. Article
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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

7 authors.

Andrew T NelsonSkaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, United States; Department of Chemistry, University of Texas at Austin, United States.
Andrew M CamelioSkaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, United States.
Karin R ClaussenSkaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, United States.
Jiyoon ChoDepartment of Pharmacology and Toxicology, College of Pharmacy, The University of Texas at Austin, United States.
Lisa TremmelDepartment of Pharmacology and Toxicology, College of Pharmacy, The University of Texas at Austin, United States.
John DiGiovanniDepartment of Pharmacology and Toxicology, College of Pharmacy, The University of Texas at Austin, United States.
Dionicio SiegelSkaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, United States; Department of Chemistry, University of Texas at Austin, United States.

Funding

Anti-Promoting Effects of Triterpenes Alone or Combined with Other PhytochemicalsR01CA164159 · NCI · UNIVERSITY OF TEXAS AT AUSTIN · PI DIGIOVANNI, JOHN, SLAGA, THOMAS J · 2012 to 2016
$2.4M
NCI NIH HHS CA164159NCI NIH HHS R01 CA164159
6 · The paper itself

Abstract

The scalable syntheses of four oxygenated triterpenes have been implemented to access substantial quantities of maslinic acid, 3-epi-maslinic acid, corosolic acid, and 3-epi-corosolic acid. Semi-syntheses proceed starting from the natural products oleanolic acid and ursolic acid. Proceeding over five steps, each of the four compounds can be synthesized on the gram scale. Divergent diastereoselective reductions of α-hydroxy ketones provided access to the four targeted diol containing compounds from two precursors of the oleanane or ursane lineage. These compounds were subsequently evaluated for their ability to inhibit inflammatory gene expression in a mouse model of chemically induced skin inflammation. All compounds possessed the ability to inhibit the expression of one or more inflammatory genes induced by 12-O-tetradecanoylphorbol-13 acetate in mouse skin, however, three of the compounds, corosolic acid, 3-epi-corosolic acid and maslinic acid were more effective than the others. The availability of gram quantities will allow further testing of these compounds for potential anti-inflammatory activities as well as cancer chemopreventive activity.

Indexed as

AnimalsAnti-Inflammatory Agents, Non-SteroidalCytokinesFemaleMiceMice, Inbred StrainsMolecular ConformationOleanolic AcidOxygenSkinTriterpenesUrsolic AcidAnti-Inflammatory Agents, Non-SteroidalCytokinesOleanolic AcidOxygenTriterpenesUrsolic Acid3-epi-Corosolic acid3-epi-Maslinic acidCancerChemopreventionCorosolic acidMaslinic acidMouseNatural productSkin inflammationSynthesisTriterpene

Identifiers

PMID26259803
PMCPMC4835183

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Registered trials

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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.