title: Digital NMR profiles as building blocks: assembling ¹H fingerprints of steviol glycosides.
abstract: This report describes a fragment-based approach to the examination of congeneric organic compounds by NMR spectroscopy. The method combines the classic interpretation of 1D- and 2D-NMR data sets with contemporary computer-assisted NMR analysis. Characteristic NMR profiles of key structural motifs were generated by (1)H iterative full spin analysis and then joined together as building blocks to recreate the (1)H NMR spectra of increasingly complex molecules. To illustrate the methodology described, a comprehensive analysis of steviol (1), seven steviol glycosides (2-8) and two structurally related isosteviol compounds (9, 10) was carried out. The study also assessed the potential impact of this method on relevant aspects of natural product research including structural verification, chemical dereplication, and mixture analysis.
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, Institute for Tuberculosis Research, and UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, Illinois 60612, United States.
authors.forename: José G
authors.initials: JG
authors.lastname: Napolitano
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, Institute for Tuberculosis Research, and UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, Illinois 60612, United States.
authors.forename: Charlotte
authors.initials: C
authors.lastname: Simmler
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, Institute for Tuberculosis Research, and UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, Illinois 60612, United States.
authors.forename: James B
authors.initials: JB
authors.lastname: McAlpine
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, Institute for Tuberculosis Research, and UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, Illinois 60612, United States.
authors.forename: David C
authors.initials: DC
authors.lastname: Lankin
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, Institute for Tuberculosis Research, and UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, Illinois 60612, United States.
authors.forename: Shao-Nong
authors.initials: SN
authors.lastname: Chen
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, Institute for Tuberculosis Research, and UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, Illinois 60612, United States.
authors.forename: Guido F
authors.initials: GF
authors.lastname: Pauli
mesh_terms: D045786:Diterpenes, Kaurane / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods*; D036625:Stevia / Q000737:chemistry*
chemical_list: D045786:Diterpenes, Kaurane; D005960:Glucosides; D006027:Glycosides; C515747:isosteviol; C012043:stevioside; C012042:steviol