title: Quillajasides A and B: New Phenylpropanoid Sucrose Esters from the Inner Bark of Quillaja saponaria Molina.
abstract: The phenolic composition of freshly prepared aqueous extracts of the inner bark of Quillaja saponaria Molina was compared to that of commercially available Quillaja extracts, which are currently used as emulsifiers in foods and cosmetics. Major phenolics in both extracts were (+)-piscidic acid and several p-coumaroyl sucrose esters. Among the latter, two new compounds were isolated and characterized: α-l-rhap-(1→4)-α-l-rhap-(1→3)-(4-O-(E)-p-coumaroyl)-α-d-glup-(1→2)-(3-O-(E)-p-coumaroyl)-β-d-fruf (quillajaside A) and β-d-apif-(1→4)-α-l-rhap-(1→4)-α-l-rhap-(1→3)-(4-O-(E)-p-coumaroyl)-α-d-glup-(1→2)-(3-O-(E)-p-coumaroyl)-β-d-fruf (quillajaside B). In addition, a putative biosynthetic pathway of at least 20 structurally related p-coumaroyl sucrose esters was tentatively identified. Besides their antioxidant activity and their potential function as substrate for enzymatic browning reactions, the new compounds are highly characteristic for both the inner bark of Q. saponaria and commercial extracts derived therefrom. Consequently, they might serve as authenticity markers for the detection of Quillaja extracts in food and cosmetic formulations.
authors.affiliation: Department of Food Physics and Meat Science, Institute of Food Science and Biotechnology, University of Hohenheim , Garbenstrasse 21/25, 70599 Stuttgart, Germany.
authors.forename: Christiane
authors.initials: C
authors.lastname: Maier
authors.affiliation: Department of Bioorganic Chemistry, Institute of Chemistry, University of Hohenheim , Garbenstrasse 30, 70599 Stuttgart, Germany.
authors.forename: Jürgen
authors.initials: J
authors.lastname: Conrad
authors.affiliation: Department of Plant Foodstuff Technology and Analysis, Institute of Food Science and Biotechnology, University of Hohenheim , Garbenstrasse 25, 70599 Stuttgart, Germany.
authors.forename: Christof B
authors.initials: CB
authors.lastname: Steingass
authors.affiliation: Department of Bioorganic Chemistry, Institute of Chemistry, University of Hohenheim , Garbenstrasse 30, 70599 Stuttgart, Germany.
authors.forename: Uwe
authors.initials: U
authors.lastname: Beifuss
authors.affiliation: Department of Plant Foodstuff Technology and Analysis, Institute of Food Science and Biotechnology, University of Hohenheim , Garbenstrasse 25, 70599 Stuttgart, Germany.|Department of Biological Sciences, King Abdulaziz University , P.O. Box 80257, Jeddah 21589, Saudi Arabia.
authors.forename: Reinhold
authors.initials: R
authors.lastname: Carle
authors.affiliation: Department of Plant Foodstuff Technology and Analysis, Institute of Food Science and Biotechnology, University of Hohenheim , Garbenstrasse 25, 70599 Stuttgart, Germany.
authors.forename: Ralf M
authors.initials: RM
authors.lastname: Schweiggert
mesh_terms: D004952:Esters / Q000032:analysis; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry*; D031990:Quillaja / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry*; D013395:Sucrose / Q000032:analysis; D014197:Trees / Q000737:chemistry
chemical_list: D004952:Esters; D010936:Plant Extracts; D012503:Saponins; D013395:Sucrose
keywords: MS/MS; NMR spectroscopy; Quillaja saponaria Molina; browning; polyphenol; saponin