Feruloylbetanin from petals of Lampranthus and feruloylamaranthin from cell suspension cultures of Chenopodium rubrum

Plant betalains: Chemistry and biochemistry

“…p-Coumaric acid derivative of 52 was identified as celosianin I (54) based on absorbance and mass spectra, alkaline hydrolysis and subsequent analysis of the products , in the absence of NMR spectra. Ferulic acid derivative of 52 was characterised conclusively from Chenopodium rubrum suspension cultures (Strack et al, 1988). The spectral data (k max 298, 324, 538 nm and m/z 903) indicated presence of one aromatic acid and 1D (including NOE) and 2D 1 H NMR spectra was characteristic of 34, two sugar molecules and a feruloyl moiety.…”

“…Whereas further characterisation of 47 was limited to absorbance and MS spectra, 48 was conclusively characterised based on [M+H] + at m/z 727 and 1 H NMR spectra (1D and 2D), which bore signatures of a feruloyl substitution at C-6 0 and 35 (Strack et al, 1988). Lampranthins accumulate in Cactaceae (Wybraniec and NowakWydra, 2007;Svenson et al, 2008), Chenopodiodeae (Bokern et al, 1992;Strack et al, 1988;Kugler et al, 2004) and Phytolaccaceae . A minor red beet pigment, on elemental analysis, revealed the presence of sulphur, while partial hydrolysis released 35 and sulphuric acid.…”

Accumulation of phenolic acid conjugates and betacyanins, and changes in the activities of enzymes involved in feruloylglucose metabolism in cell-suspension cultures of Chenopodium rubrum L.

“…See experimental section for further chromatographic conditions. 4-Coumaroylamaranthin (celosianin I; Strack et al 1988a) and the betaxanthins vulgaxanthin I and vulgaxanthin II (Berlin et al 1986), not seen in the present analysis, were also present but at very minor concentrations 50 lal adjusted to 60 mM citrate-phosphate buffer (pH 6.0) (90 min incubation). Activity determination (HPLC): linear gradient elution within 10 min from 75:25 to 40:60 of solvent A.1 :solvent B.1 at 1 ml 9 min-1.…”

“…2). These compounds are the previously identified betacyanins betanin (betanidin 5-0-glucoside) (S, R." 6, 9), amaranthin (betanidin 5-0-glucuronosylglucoside) (S, R; 3, 4) (Berlin et al 1986) and celosianin II (O-feruloylamaranthin) ( S, R; 13, 14) (Strack et al 1988a) as well as the hydroxycinnamic acid conjugates 1-O-(4-coumaroyl)-fl-glucose (7), 1-Oferuloyl-fl-glucose (10) (Strack et al 1984) and 1-Oferuloyl-(fl-l,2-glucuronosyl)-fl-glucose (8) (Bokern et al 1987).…”

“…betalains with betanin, amaranthin and celosianin II as the predominant betacyanins (Berlin et al 1986;Strack et al 1988a), and hydroxycinnamic acid conjugates (esters) with glucose and glucuronosylglucose as the main soluble components, as well as the cell wallbound hydroxycinnamic acids 4-coumaric and ferulic acids (Strack et al 1984;Bokern et al 1987). The Ch.…”