Acylated anthocyanidin 3-sophoroside-5-glucosides from Ajuga reptans flowers and the corresponding cell cultures.
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.
Terahara
N
N
Department of Food Science and Technology, College of Horticulture, Minami-Kyushu University, Takanabe, Miyazaki 884-0003, Japan. terahara@nankyudai.ac.jp
Callebaut
A
A
Ohba
R
R
Nagata
T
T
Ohnishi-Kameyama
M
M
Suzuki
M
M
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
D000872:Anthocyanins; D000975:Antioxidants; D005960:Glucosides; D007529:Isoflavones