2D NMR barcoding and differential analysis of complex mixtures for chemical identification: The Actaea triterpenes

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DOIResolve DOI: http://doi.org/10.1021/ac500188j
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TypeArticle
Journal titleAnalytical Chemistry
ISSN1520-6882
Volume86
Issue8
Pages39643972; # of pages: 9
SubjectBar codes; Mixtures; Nuclear magnetic resonance; Chemical identification; Differential analysis; Molecular information; Software-based recognition; Spatial relationships; Spectroscopic information; Structural identification; Structural information; Chemical analysis
AbstractThe interpretation of NMR spectroscopic information for structure elucidation involves decoding of complex resonance patterns that contain valuable molecular information (δ and J), which is not readily accessible otherwise. We introduce a new concept of 2D-NMR barcoding that uses clusters of fingerprint signals and their spatial relationships in the δ-δ coordinate space to facilitate the chemical identification of complex mixtures. Similar to widely used general barcoding technology, the structural information of individual compounds is encoded as a specifics pattern of their C,H correlation signals. Software-based recognition of these patterns enables the structural identification of the compounds and their discrimination in mixtures. Using the triterpenes from various Actaea (syn. Cimicifuga) species as a test case, heteronuclear multiple-bond correlation (HMBC) barcodes were generated on the basis of their structural subtypes from a statistical investigation of their δH and δC data in the literature. These reference barcodes allowed in silico identification of known triterpenes in enriched fractions obtained from an extract of A. racemosa (black cohosh). After dereplication, a differential analysis of heteronuclear single-quantum correlation (HSQC) spectra even allowed for the discovery of a new triterpene. The 2D barcoding concept has potential application in a natural product discovery project, allowing for the rapid dereplication of known compounds and as a tool in the search for structural novelty within compound classes with established barcodes. © 2014 American Chemical Society.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC); NRC Institute for Marine Biosciences (IMB-IBM)
Peer reviewedYes
NPARC number21272179
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Record identifierb2d08a00-11d8-4f94-b686-a36c700c985a
Record created2014-07-23
Record modified2016-05-09
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