title: Exploiting the Complementarity between Dereplication and Computer-Assisted Structure Elucidation for the Chemical Profiling of Natural Cosmetic Ingredients: Tephrosia purpurea as a Case Study.
abstract: The aqueous-ethanolic extract of Tephrosia purpurea seeds is currently exploited in the cosmetic industry as a natural ingredient of skin lotions. The aim of this study was to chemically characterize this ingredient by combining centrifugal partition extraction (CPE) as a fractionation tool with two complementary identification approaches involving dereplication and computer-assisted structure elucidation. Following two rapid fractionations of the crude extract (2 g), seven major compounds namely, caffeic acid, quercetin-3-O-rutinoside, ethyl galactoside, ciceritol, stachyose, saccharose, and citric acid, were unambiguously identified within the CPE-generated simplified mixtures by a recently developed (13)C NMR-based dereplication method. The structures of four additional compounds, patuletin-3-O-rutinoside, kaempferol-3-O-rutinoside, guaiacylglycerol 8-vanillic acid ether, and 2-methyl-2-glucopyranosyloxypropanoic acid, were automatically elucidated by using the Logic for Structure Determination program based on the interpretation of 2D NMR (HSQC, HMBC, and COSY) connectivity data. As more than 80% of the crude extract mass was characterized without need for tedious and labor-intensive multistep purification procedures, the identification tools involved in this work constitute a promising strategy for an efficient and time-saving chemical profiling of natural extracts.
authors.affiliation: †Institut de Chimie Moléculaire de Reims (UMR CNRS 7312), SFR CAP'SANTE, UFR de Pharmacie, Université de Reims Champagne-Ardenne, Reims, France.
authors.forename: Jane
authors.initials: J
authors.lastname: Hubert
authors.affiliation: †Institut de Chimie Moléculaire de Reims (UMR CNRS 7312), SFR CAP'SANTE, UFR de Pharmacie, Université de Reims Champagne-Ardenne, Reims, France.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Chollet
authors.affiliation: †Institut de Chimie Moléculaire de Reims (UMR CNRS 7312), SFR CAP'SANTE, UFR de Pharmacie, Université de Reims Champagne-Ardenne, Reims, France.|‡Soliance-Givaudan, Pomacle, France.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Purson
authors.affiliation: ‡Soliance-Givaudan, Pomacle, France.
authors.forename: Romain
authors.initials: R
authors.lastname: Reynaud
authors.affiliation: †Institut de Chimie Moléculaire de Reims (UMR CNRS 7312), SFR CAP'SANTE, UFR de Pharmacie, Université de Reims Champagne-Ardenne, Reims, France.
authors.forename: Dominique
authors.initials: D
authors.lastname: Harakat
authors.affiliation: †Institut de Chimie Moléculaire de Reims (UMR CNRS 7312), SFR CAP'SANTE, UFR de Pharmacie, Université de Reims Champagne-Ardenne, Reims, France.
authors.forename: Agathe
authors.initials: A
authors.lastname: Martinez
authors.affiliation: †Institut de Chimie Moléculaire de Reims (UMR CNRS 7312), SFR CAP'SANTE, UFR de Pharmacie, Université de Reims Champagne-Ardenne, Reims, France.
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Nuzillard
authors.affiliation: †Institut de Chimie Moléculaire de Reims (UMR CNRS 7312), SFR CAP'SANTE, UFR de Pharmacie, Université de Reims Champagne-Ardenne, Reims, France.
authors.forename: Jean-Hugues
authors.initials: JH
authors.lastname: Renault
mesh_terms: D002867:Chromones / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry; D044949:Kaempferols / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010936:Plant Extracts / Q000494:pharmacology; D011794:Quercetin / Q000031:analogs & derivatives / Q000737:chemistry; D012431:Rutin; D012639:Seeds / Q000737:chemistry; D031304:Tephrosia / Q000737:chemistry*
chemical_list: D002867:Chromones; D005960:Glucosides; D044949:Kaempferols; D010936:Plant Extracts; C492687:kaempferol-3-O-rutinoside; D012431:Rutin; C079162:patuletin; D011794:Quercetin