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Record W2567241234 · doi:10.1021/acs.jnatprod.6b00759

Polyoxygenated Cyclohexenes and Other Constituents of <i>Cleistochlamys kirkii</i> Leaves

2016· article· en· W2567241234 on OpenAlex
Stephen S. Nyandoro, Joan J. E. Munissi, Amra Gruhonjic, Sandra Duffy, Fangfang Pan, Rakesh Puttreddy, John P. Holleran, Paul Fitzpatrick, Jerry Pelletier, Vicky M. Avery, Kari Rissanen, Máté Erdélyi

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueJournal of Natural Products · 2016
Typearticle
Languageen
FieldAgricultural and Biological Sciences
TopicPhytochemistry and Biological Activities
Canadian institutionsMcGill University
FundersAustralian Research CouncilAcademy of Finland
KeywordsStereochemistryChemistryIC50CyclohexeneButenolideCancer cell linesIn vitroBiologyCancer cellBiochemistry

Abstract

fetched live from OpenAlex

Thirteen new metabolites, including the polyoxygenated cyclohexene derivatives cleistodiendiol ( 1 ), cleistodienol B ( 3 ), cleistenechlorohydrins A ( 4 ) and B ( 5 ), cleistenediols A–F ( 6 – 11 ), cleistenonal ( 12 ), and the butenolide cleistanolate ( 13 ), 2,5-dihydroxybenzyl benzoate (cleistophenolide, 14 ), and eight known compounds ( 2, 15 – 21 ) were isolated from a MeOH extract of the leaves of Cleistochlamys kirkii . The purified metabolites were identified by NMR spectroscopic and mass spectrometric analyses, whereas the absolute configurations of compounds 1, 17, and 19 were established by single-crystal X-ray diffraction. The configuration of the exocyclic double bond of compound 2 was revised based on comparison of its NMR spectroscopic features and optical rotation to those of 1, for which the configuration was determined by X-ray diffraction. Observation of the co-occurrence of cyclohexenoids and heptenolides in C. kirkii is of biogenetic and chemotaxonomic significance. Some of the isolated compounds showed activity against Plasmodium falciparum (3D7, Dd2), with IC 50 values of 0.2–40 μM, and against HEK293 mammalian cells (IC 50 2.7–3.6 μM). While the crude extract was inactive at 100 μg/mL against the MDA-MB-231 triple-negative breast cancer cell line, some of its isolated constituents demonstrated cytotoxic activity with IC 50 values ranging from 0.03–8.2 μM. Compound 1 showed the most potent antiplasmodial (IC 50 0.2 μM) and cytotoxic (IC 50 0.03 μM, MDA-MB-231 cell line) activities. None of the compounds investigated exhibited translational inhibitory activity in vitro at 20 μM.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.056
Threshold uncertainty score0.114

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.016
GPT teacher head0.210
Teacher spread0.194 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it