NDLI: Lanthanide-induced shift reagents enable the structural elucidation of natural products in inseparable complex mixtures – the case of elemenal from Inula helenium L. (Asteraceae)

Content Provider	Royal Society of Chemistry (RSC)
Author	Radulović, Niko S. Genčić, Marija S.
Copyright Year	2015
Abstract	The use of lanthanide complexes for resolving intricate NMR signals and, in the case of chiral ligands, for determining enantiomeric excess has progressively decreased in the last 30 years. Recently, a sesquiterpene aldehyde from Inula helenium with a possible potent antistaphylococcal activity remained unidentified due to the impossibility of separating the compound from its complex matrix available in very low amounts (ca. 5 mg). Detailed analyses of 1D and 2D NMR spectra of this original complex sample allowed access to a very limited amount of structural data for the unknown aldehyde. We decided to investigate the potential usefulness of lanthanide-induced shift reagents for the resolution and assigning of overlapped 1H NMR signals originating from different components of this complex mixture (i.e. for a qualitative analysis). The incremental addition of tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium(III) (Eu(fod)3) led to a simplification of the NMR spectra in terms of signal overlap and removal of chemical shift degeneracy, allowing the mining of crucial data from the shifted NMR spectra. 2D NMR spectra (1H–1H–COSY, NOESY, HSQC and HMBC) of the sample mixed with Eu(fod)3 proved to be particularly valuable in this respect. The obtained additional information revealed that the compound in question was a rare sesquiterpene – elemenal (elema-1,3,11(13)-trien-12-al). Therefore, herein we report on a new chromatography-free methodology that could be of value in structure elucidation of unknown compounds even if they are not available in a pure state.
Starting Page	72670
Ending Page	72682
Page Count	13
File Format	HTM / HTML PDF
ISSN	20462069
Volume Number	5
Issue Number	89
Journal	RSC Advances
DOI	10.1039/c5ra13109j
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Lanthanide Chemical shift HMBC Sesquiterpene Heteronuclear single quantum coherence spectroscopy Nuclear magnetic resonance spectroscopy Enantiomeric excess Aldehyde Inula Elecampane Europium Matrix (mathematics)
Content Type	Text
Resource Type	Article
Subject	Chemistry Chemical Engineering

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

Elecampane (Inula helenium) Root Extract and Its Major Sesquiterpene Lactone, Alantolactone, Inhibit Adipogenesis of 3T3-L1 Preadipocytes

From Monographs to Chromatograms: The Antimicrobial Potential of Inula helenium L. (Elecampane) Naturalised in Ireland

Use of chiral lanthanide shift reagents in the elucidation of NMR signals from enantiomeric mixtures of polycyclic compounds

Chiral nuclear magnetic resonance shift reagents: Lanthanide mixtures with 1‐(1‐naphthyl) ethylurea derivatives of amino acids

Isoheleproline: a new amino acid-sesquiterpene adduct from Inula helenium

Mixtures of Chiral and Achiral Chemical Shift Reagents of Europium and Their Benefits for the Determination of Enantiomeric Purity

Antioxidant activity and fructan content in root extracts from elecampane (Inula helenium L.)

Desktop NMR for structure elucidation and identification of strychnine adulteration

Sticky Elecampane , Inula viscosa ( L . ) Aiton ( Asteraceae )

Lanthanide-induced shift reagents enable the structural elucidation of natural products in inseparable complex mixtures – the case of elemenal from Inula helenium L. (Asteraceae)

Similar Documents

Elecampane (Inula helenium) Root Extract and Its Major Sesquiterpene Lactone, Alantolactone, Inhibit Adipogenesis of 3T3-L1 Preadipocytes

From Monographs to Chromatograms: The Antimicrobial Potential of Inula helenium L. (Elecampane) Naturalised in Ireland

Use of chiral lanthanide shift reagents in the elucidation of NMR signals from enantiomeric mixtures of polycyclic compounds

Chiral nuclear magnetic resonance shift reagents: Lanthanide mixtures with 1‐(1‐naphthyl) ethylurea derivatives of amino acids

Isoheleproline: a new amino acid-sesquiterpene adduct from Inula helenium

Mixtures of Chiral and Achiral Chemical Shift Reagents of Europium and Their Benefits for the Determination of Enantiomeric Purity

Antioxidant activity and fructan content in root extracts from elecampane (Inula helenium L.)

Desktop NMR for structure elucidation and identification of strychnine adulteration

Sticky Elecampane , Inula viscosa ( L . ) Aiton ( Asteraceae )

Lanthanide-induced shift reagents enable the structural elucidation of natural products in inseparable complex mixtures – the case of elemenal from Inula helenium L. (Asteraceae)