Abstract:A new acylated anthocyanin has been isolated from flowers of Nigritella and Orchis and identified as cyanidin 3-O-β-(6”-O-oxalyl)-glucoside on the basis of TLC , HPLC , FABMS, 1H and 13C NMR . This pigment was found to be present in various members of the Orchidaceae.
“…Proton and Carbon NMR. 1 H and 13 C NMR spectra were recorded on a Bruker AMX 300 spectrometer (Bruker Biospin, Germany) at 300.13 and 75.49 MHz, respectively. Anthocyanins were dissolved in a mixture of methanol-d 4/TFA-d1 (19:1, v/v).…”
Anthocyanins from blood orange [Citrus sinensis (L.) Osbeck] juices were isolated and purified by means of high-speed countercurrent chromatography and preparative high-performance liquid chromatography. Structures of the pigments were then elucidated by electrospray ionization multiple mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy. The major anthocyanins of the juice were characterized as cyanidin 3-glucoside and cyanidin 3-(6"-malonylglucoside). Furthermore, six minor anthocyanins were detected and identified as cyanidin 3,5-diglucoside, delphinidin 3-glucoside, cyanidin 3-sophoroside, delphinidin 3-(6"-malonylglucoside), peonidin 3-(6"-malonylglucoside), and cyanidin 3-(6"-dioxalylglucoside). The occurrence of the latter compound in blood oranges is reported here for the first time, together with full NMR spectroscopic data. Further investigations revealed the presence of four anthocyanin-derived pigments, which are formed through a direct reaction between anthocyanins and hydroxycinnamic acids during prolonged storage of the juice. These novel pyranoanthocyanins were identified as the 4-vinylphenol, 4-vinylcatechol, 4-vinylguaiacol, and 4-vinylsyringol adducts of cyanidin 3-glucoside through comparison of their mass spectrometric and chromatographic properties with those of synthesized reference compounds.
“…Proton and Carbon NMR. 1 H and 13 C NMR spectra were recorded on a Bruker AMX 300 spectrometer (Bruker Biospin, Germany) at 300.13 and 75.49 MHz, respectively. Anthocyanins were dissolved in a mixture of methanol-d 4/TFA-d1 (19:1, v/v).…”
Anthocyanins from blood orange [Citrus sinensis (L.) Osbeck] juices were isolated and purified by means of high-speed countercurrent chromatography and preparative high-performance liquid chromatography. Structures of the pigments were then elucidated by electrospray ionization multiple mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy. The major anthocyanins of the juice were characterized as cyanidin 3-glucoside and cyanidin 3-(6"-malonylglucoside). Furthermore, six minor anthocyanins were detected and identified as cyanidin 3,5-diglucoside, delphinidin 3-glucoside, cyanidin 3-sophoroside, delphinidin 3-(6"-malonylglucoside), peonidin 3-(6"-malonylglucoside), and cyanidin 3-(6"-dioxalylglucoside). The occurrence of the latter compound in blood oranges is reported here for the first time, together with full NMR spectroscopic data. Further investigations revealed the presence of four anthocyanin-derived pigments, which are formed through a direct reaction between anthocyanins and hydroxycinnamic acids during prolonged storage of the juice. These novel pyranoanthocyanins were identified as the 4-vinylphenol, 4-vinylcatechol, 4-vinylguaiacol, and 4-vinylsyringol adducts of cyanidin 3-glucoside through comparison of their mass spectrometric and chromatographic properties with those of synthesized reference compounds.
“…In Orchidaceae, the recent discovery of cyanidin 3-oxalylglucoside as a taxonomic marker for certain European species (see Table 1.8) is of considerable interest, but further surveys are needed to see how widespread this novel pigment is (Strack et al, 1986). Considering the enormous biological and popular interest in orchid flowers, it is surprising how little is known of the anthocyanins in the family and further studies are bound to be rewarding.…”
“…To the best of our knowledge, 41 acylated anthocyanins have been isolated and determined from various flowers of the plants in the Orchidaceae (Fossen and Øvstedal, 2003;Saito et al, 1994Saito et al, , 1995aStrack et al, 1986Strack et al, , 1989Tatsuzawa et al, 1994Tatsuzawa et al, , 1996aTatsuzawa et al, , b, 1997Tatsuzawa et al, , 1998Tatsuzawa et al, , 2004Tatsuzawa et al, , 2005Tatsuzawa et al, , 2006Williams et al, 2002). On the basis of these results, hydroxycinnamic acids of acylated anthocyanins were revealed to be responsible for the stabilization and bluing of the flower color.…”
A novel acylated anthocyanin was identified from the violet flowers of Bletilla striata 'Murasaki Shikibu' as a major floral anthocyanin. This pigment was based on cyanidin 3,7-diglucoside as its deacylanthocyanin, and was acylated with two molecules of caffeic acid. The structure was unambiguously elucidated by chemical and spectroscopic methods to be cyanidinBased on the results of the present study, the bluing effect was discussed for the violet flowers of a given cultivar.
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