title: Acylated anthocyanidin 3-sophoroside-5-glucosides from Ajuga reptans flowers and the corresponding cell cultures.
abstract: Four anthocyanins from Ajuga reptans flowers and its cell cultures were isolated, and a fifth was also characterized by HPLC-mass spectrometry. By means of chemical and spectroscopic analyses, their structures were identified as delphinidin 3-(p-coumaroyl-feruloyl)sophoroside-5-malonylglucoside, delphinidin 3-(diferuloyl)sophoroside-5-malonylglucoside, and cyanidin 3-(di-p-coumaroyl)sophoroside-5-glucoside, respectively. The other two were tentatively identified as delphinidin 3-(diferuloyl)sophoroside-5-glucoside and cyanidin 3-(feruloyl-p-coumaroyl)sophoroside-5-malonylglucoside. In neutral aqueous solution, the crude extract from A. reptans flower cell cultures and the major anthocyanin cyanidin 3-(di-p-coumaroyl)sophoroside-5-malonylglucoside were more stable than cyanidin 3-glucoside, and also prevented more efficiently peroxidation than did the latter. A. reptans flower cell culture anthocyanins may have a potential as natural colorants for food utilities or other purposes.
authors.affiliation: Department of Food Science and Technology, College of Horticulture, Minami-Kyushu University, Takanabe, Miyazaki 884-0003, Japan. terahara@nankyudai.ac.jp
authors.forename: N
authors.initials: N
authors.lastname: Terahara
authors.forename: A
authors.initials: A
authors.lastname: Callebaut
authors.forename: R
authors.initials: R
authors.lastname: Ohba
authors.forename: T
authors.initials: T
authors.lastname: Nagata
authors.forename: M
authors.initials: M
authors.lastname: Ohnishi-Kameyama
authors.forename: M
authors.initials: M
authors.lastname: Suzuki
mesh_terms: D000215:Acylation; D000872:Anthocyanins; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002240:Carbohydrate Sequence; D002478:Cells, Cultured; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007529:Isoflavones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019686:Lamiaceae / Q000737:chemistry* / Q000166:cytology; D008969:Molecular Sequence Data; D013057:Spectrum Analysis
chemical_list: D000872:Anthocyanins; D000975:Antioxidants; D005960:Glucosides; D007529:Isoflavones