DANSing with
            <i>Caenorhabditis elegans</i>

Hu, Patrick J.; Sherman, David H.

doi:10.1073/pnas.0903021106

Cited by 1 publication

(1 citation statement)

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“…By such a differential analysis of several HSQC spectra, 10 might be structurally identified from the mixture without a physical separation. Recently, the differential analysis of 2D-NMR spectra has been shown to be powerful in the identification of new compounds from (residually) complex natural product mixtures. , In the present study, the HSQC spectra were considered to be highly appropriate for the differential analysis, because they provide both 1 H and 13 C chemical shift information but yield much less complicated cross peak patterns than HMBC due to the restriction to only one-bond 1 H– 13 C correlations. As the major structural differences of Actaea triterpenes arise from modifications of their side chains at C-17, the differential analysis of their HSQC spectra can be focused on one specific region, i.e., δ H 5.50/3.30 and δ C 100.0/50.0, where the fingerprint signals of the ether, oxirane, and acetoxy groups in the side chains are commonly observed.…”

Section: Resultsmentioning

confidence: 99%

2D NMR Barcoding and Differential Analysis of Complex Mixtures for Chemical Identification: The Actaea Triterpenes

et al. 2014

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The 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.

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Section: Resultsmentioning

confidence: 99%