Evidence map›Paper›PMID 26042470›Full record

ArticleJournal of natural products2015

Antimalarial 5,6-Dihydro-α-pyrones from Cryptocarya rigidifolia: Related Bicyclic Tetrahydro-α-Pyrones Are Artifacts1.

Yixi Liu, L Harinantenaina Rakotondraibe, Peggy J Brodie, Jessica D Wiley, Maria B Cassera, James S Miller, F Ratovoson, Etienne Rakotobe, Vincent E Rasamison, David G I Kingston

Open access · bronzeAbstract read
In one paragraph

Article in Journal of natural products, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.

0numbers the graph read from it
0cells of the map it votes in
13citing papers in PubMed
4.0field-weighted citation impact, top 7% 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

13 citing papers in PubMed, 55 citations in OpenAlex.

  1. Review
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  4. Frontiers in pharmacology · 2025
    Review
  5. Review
  6. Article
  7. Article
  8. Article
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  10. Article
  11. New Antiplasmodial Diterpenes from Gutierrezia sarothrae.Natural product communications · 2016
    Article
  12. Article
  13. 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 at 3 institutions in 2 countries.

Yixi Liu†Department of Chemistry and the Virginia Tech Center for Drug Discovery, Virginia Tech, M/C 0212, Blacksburg, Virginia 24061, United States.
L Harinantenaina Rakotondraibe†Department of Chemistry and the Virginia Tech Center for Drug Discovery, Virginia Tech, M/C 0212, Blacksburg, Virginia 24061, United States.
Peggy J Brodie†Department of Chemistry and the Virginia Tech Center for Drug Discovery, Virginia Tech, M/C 0212, Blacksburg, Virginia 24061, United States.
Jessica D Wiley‡Department of Biochemistry and the Virginia Tech Center for Drug Discovery, Virginia Tech, M/C 0308, Blacksburg, Virginia 24061, United States.
Maria B Cassera‡Department of Biochemistry and the Virginia Tech Center for Drug Discovery, Virginia Tech, M/C 0308, Blacksburg, Virginia 24061, United States.
James S Miller§Missouri Botanical Garden, P.O. Box 299, St. Louis, Missouri 63166, United States.
F Ratovoson⊥Missouri Botanical Garden, Lot VP 31 Ankadibevava, Anjohy Antananarivo 101, Madagascar.
Etienne Rakotobe∥Centre National d'Application des Recherches Pharmaceutiques, B.P. 702, Antananarivo 101, Madagascar.
Vincent E Rasamison∥Centre National d'Application des Recherches Pharmaceutiques, B.P. 702, Antananarivo 101, Madagascar.
David G I Kingston†Department of Chemistry and the Virginia Tech Center for Drug Discovery, Virginia Tech, M/C 0212, Blacksburg, Virginia 24061, United States.
Virginia Tech · USMissouri Botanical Garden · USNational Application Center for Pharmaceutical Research · MG

Funding

BIODIVERSITY UTILIZATION IN MADAGASCAR AND SURINAMEU01TW000313 · FIC · VIRGINIA POLYTECHNIC INST AND ST UNIV · PI KINGSTON, DAVID GEORGE IAN · 1993 to 2013
$9.5M
Discovery and Mechanism of Antimalarial Natural ProductsR01AT008088 · NCCIH · VIRGINIA POLYTECHNIC INST AND ST UNIV · PI CASSERA, MARIA BELEN, CLEMENT, JASON ANDERSON · 2014 to 2018
$2.0M
FIC NIH HHS U01 TW000313FIC NIH HHS U01 TW00313NCCIH NIH HHS R01 AT008088
6 · The paper itself

Abstract

Antimalarial bioassay-guided fractionation of an EtOH extract of the root wood of Cryptocarya rigidifolia (Lauraceae) led to the isolation of the five new 5,6-dihydro-α-pyrones cryptorigidifoliols A-E (1-5) and the six bicyclic tetrahydro-α-pyrone derivatives cryptorigidifoliols F-K (6-11). The structure elucidations of all compounds were made on the basis of the interpretation of spectroscopic data and chemical derivatization, and the relative and absolute configurations were determined by NOESY, electronic circular dichroism (ECD), and (1)H NMR analysis of α-methoxyphenylacetyl (MPA) derivatives. The bicyclic tetrahydro-α-pyrone derivatives were identified as products of acid-catalyzed intramolecular Michael addition of the 5,6-dihydro-α-pyrones in the presence of silica gel. A structure-activity relationship study suggested that the presence of an α,β-unsaturated carbonyl moiety is not essential for potent antimalarial activity.

Indexed as

AntimalarialsCircular DichroismCryptocaryaCrystallography, X-RayMolecular StructureNuclear Magnetic Resonance, BiomolecularPyronesStructure-Activity RelationshipAntimalarialsPyrones

Identifiers

PMID26042470
PMCPMC4485685
OpenAlexW590809992

What OpenQuestion holds

Textmetadata
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.