Full absolute stereostructures of natural products directly from crude extracts: The HPLC-MS/ MS-NMR-CD 'triad'.
This chapter deals with an efficient methodology available in our Center of Excellence, BIOTECmarin: the novel analytical 'triad' HPLC-MS/MS-NMR-CD. By this method, which was, in this complemented form, first introduced into phytochemical research by our group, we can not only rapidly identify known structures, but can also investigate new metabolites and establish their full absolute stereostructures online, directly from crude extracts, without the necessity of first isolating the compounds. The LC-CD option, which we have been using for the first time in natural products analysis, becomes even more valuable by the possibility of interpreting the online CD spectra by their simulation or prediction through quantum chemical calculation, thus avoiding the usual, often risky, empirical comparison with the CD spectra of (sometimes not so related) compounds of known absolute stereostructure or the application of (sometimes not really applicable) likewise empirical CD rules. The hyphenated analytical methods are additionally complemented by our synthetic expertise, again involving new concepts and strategies developed in our group. The methods and their application will first be explained and exemplified for plant-derived ('terrestrial') natural products, for which they were initially developed, and will then be applied to the online structural elucidation of novel natural products from marine organisms.
Bringmann
G
G
Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany.
Lang
G
G
D000470:Alkaloids / Q000737:chemistry; D000818:Animals; D001709:Biotechnology; D002227:Carbazoles / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D002942:Circular Dichroism / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D013058:Mass Spectrometry / Q000379:methods*; D008956:Models, Chemical; D010936:Plant Extracts / Q000378:metabolism; D011161:Porifera / Q000378:metabolism*; D011804:Quinolines / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D002227:Carbazoles; D010936:Plant Extracts; D011804:Quinolines; C041514:carbazole; C037219:quinoline