Evidence map›Paper›PMID 31150264›Full record

ArticleOrganic letters2019

Elucidation of Spirodactylone, a Polycyclic Alkaloid from the Sponge Dactylia sp., and Nonenzymatic Generation from the Co-metabolite Denigrin B.

Unwoo Kang, Donald R Caldwell, Laura K Cartner, Dongdong Wang, Chang-Kwon Kim, Xiangrong Tian, Heidi R Bokesch, Curtis J Henrich, Girma M Woldemichael, Martin J Schnermann and 1 more

Abstract read
In one paragraph

Article in Organic letters, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing 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

4 citing papers in PubMed.

  1. ThiF-Like Enzyme Chemistry in Primary and Secondary Metabolism.Chembiochem : a European journal of chemical biology · 2025
    Review
  2. Article
  3. Article
  4. 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

11 authors.

Unwoo KangMolecular Targets Program, Center for Cancer Research , National Cancer Institute , Frederick , Maryland 21702-1201 , United States.
Donald R CaldwellChemical Biology Laboratory, Center for Cancer Research , National Cancer Institute , Frederick , Maryland 21702-1201 , United States.
Laura K CartnerMolecular Targets Program, Center for Cancer Research , National Cancer Institute , Frederick , Maryland 21702-1201 , United States.
Dongdong WangMolecular Targets Program, Center for Cancer Research , National Cancer Institute , Frederick , Maryland 21702-1201 , United States.
Chang-Kwon KimMolecular Targets Program, Center for Cancer Research , National Cancer Institute , Frederick , Maryland 21702-1201 , United States.
Xiangrong TianMolecular Targets Program, Center for Cancer Research , National Cancer Institute , Frederick , Maryland 21702-1201 , United States.
Heidi R BokeschMolecular Targets Program, Center for Cancer Research , National Cancer Institute , Frederick , Maryland 21702-1201 , United States.
Curtis J HenrichMolecular Targets Program, Center for Cancer Research , National Cancer Institute , Frederick , Maryland 21702-1201 , United States.
Girma M WoldemichaelMolecular Targets Program, Center for Cancer Research , National Cancer Institute , Frederick , Maryland 21702-1201 , United States.
Martin J SchnermannChemical Biology Laboratory, Center for Cancer Research , National Cancer Institute , Frederick , Maryland 21702-1201 , United States.ORCID 0000-0002-0503-0116
Kirk R GustafsonMolecular Targets Program, Center for Cancer Research , National Cancer Institute , Frederick , Maryland 21702-1201 , United States.ORCID 0000-0001-6821-4943

Funding

Natural Products Discovery and Characterization Through Network CollaborationsZIABC011568 · NCI · DIVISION OF BASIC SCIENCES - NCI · PI DU, LIN · 2014 to 2025
$17.2M
Synthesis and evaluation of small-molecule imaging agentsZIABC011506 · NCI · DIVISION OF BASIC SCIENCES - NCI · PI SCHNERMANN, MARTIN · 2013 to 2025
$12.1M
CCR NIH HHS HHSN261200800001CIntramural NIH HHS ZIA BC011506Intramural NIH HHS ZIA BC011568NCI NIH HHS HHSN261200800001E
6 · The paper itself

Abstract

Spirodactylone (1), a hexacyclic indolizidone alkaloid possessing a novel spiro ring system, was isolated from the marine sponge Dactylia sp. The structure was elucidated by extensive spectroscopic methods including application of the LR-HSQMBC NMR pulse sequence. Oxidative cyclization of denigrin B (2), an aryl-substituted 2-oxo-pyrroline derivative that was also isolated from the sponge extract, provided material identical to spirodactylone (1). This confirmed the assigned structure and provides insight into the probable biogenesis of 1.

Indexed as

AlkaloidsAnimalsCyclizationIndolizinesMagnetic Resonance SpectroscopyMolecular StructureOxidation-ReductionPolycyclic CompoundsPoriferaPyrrolesAlkaloidsdenigrin BIndolizinesPolycyclic CompoundsPyrroles

Identifiers

PMID31150264
PMCPMC8274939

What OpenQuestion holds

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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.