Enantiomeric Discorhabdin Alkaloids and Establishment of Their Absolute Configurations Using Theoretical Calculations of Electronic Circular Dichroism Spectra

Enantiomeric pairs of the cytotoxic pyrroloiminoquinone marine alkaloids discorhabdins B (2), G*/I (3), L (4), and W (5) have been isolated from Latrunculia species sponges collected at different locations around the coast of New Zealand. The absolute configuration of all compounds was secured by co...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 73; no. 22; pp. 9133 - 9136
Main Authors Grkovic, Tanja, Ding, Yuanqing, Li, Xing-Cong, Webb, Victoria L, Ferreira, Daneel, Copp, Brent R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.11.2008
Amer Chemical Soc
Subjects
Alkaloids - chemistry
Chemistry
Chemistry, Organic
Circular Dichroism
Electrons
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Physical Sciences
Preparations and properties
Quantum Theory
Quinones - chemistry
Science & Technology
Stereoisomerism
New Zealand
Oceania
METABOLITES
GENUS LATRUNCULIA
SPONGE
PYRROLOIMINOQUINONE
Antineoplastic agent
Quinone imine
Pharmacognosy
Theoretical study
Animal origin
Cytotoxicity
Biological activity
Circular dichroism
Marine environment
Alkaloid
Porifera
Circular dichroism spectrometry
Absolute configuration
Density functional method
Sponge
Invertebrata
Spectrophotometry
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Summary:Enantiomeric pairs of the cytotoxic pyrroloiminoquinone marine alkaloids discorhabdins B (2), G*/I (3), L (4), and W (5) have been isolated from Latrunculia species sponges collected at different locations around the coast of New Zealand. The absolute configuration of all compounds was secured by comparison of observed data with the results of time-dependent density functional theory (TDDFT) calculations of electronic circular dichroism (ECD) spectra. Enantiomeric discorhabdins exhibit equipotent antiproliferative biological activity.
Bibliography:ark:/67375/TPS-N8ZMC67S-S
Isolation details, spectroscopic data (NMR, experimental and calculated ECD) for all compounds and computational optimized Z-matrixes, thermodynamic parameters, and frequencies for 1−5. This material is available free of charge via the Internet at http://pubs.acs.org.
istex:7070666AFEDEADC1EC8F1DD8B9AAF117E1D5F418
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo801622n