Acylated anthocyanidin 3-sophoroside-5-glucosides from Ajuga reptans flowers and the corresponding cell cultures

• Published in: Phytochemistry (Oxford) Vol. 58; no. 3; pp. 493 - 500
• Main Authors: Terahara, Norihiko, Callebaut, Alfons, Ohba, Riichiro, Nagata, Tadahiro, Ohnishi-Kameyama, Mayumi, Suzuki, Masahiro
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01-10-2001; Elsevier
• Subjects: Acylated anthocyanidin 3-Sophoroside-5-glucosides; Acylation; Ajuga reptans L; Anthocyanin; Anthocyanins; Antioxidants - chemistry; Antioxidants - isolation & purification; Antioxidants - pharmacology; Antioxidative activity; Biological and medical sciences; Carbohydrate Sequence; Cell culture; Cells, Cultured; Chemical constitution; Flavonoid; Fundamental and applied biological sciences. Psychology; Glucosides - chemistry; Glucosides - isolation & purification; Glucosides - pharmacology; Isoflavones - chemistry; Isoflavones - isolation & purification; Isoflavones - pharmacology; Lamiaceae; Lamiaceae - chemistry; Lamiaceae - cytology; Molecular Sequence Data; Plant physiology and development; Spectrum Analysis; Stability; Anthocyanin; Cell culture; Ajuga reptans L; Antioxidative activity; Stability; Lamiaceae; Flavonoid; Acylated anthocyanidin 3-Sophoroside-5-glucosides; Flower; Molecular structure; Glucoside; Antioxidant; Biological activity; Labiatae; Dicotyledones; Angiospermae; Anthocyanidin; Isolation; Spermatophyta
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(01)00172-8

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.
Three anthocyanins, delphinidin 3-(
p-coumaroyl-feruloyl)sophoroside-5-malonylglucoside and delphinidin 3-(differuloyl)sophoroside-5-malonylglucoside from
Ajuga reptans flowers, and cyanidin 3-(di-
p-coumaroyl)sophoroside-5-glucoside from the cell cultures of
Ajuga reptans flowers, were isolated.