Identification of Betalains from Petioles of Differently Colored Swiss Chard (Beta vulgaris L. ssp. cicla [L.] Alef. Cv. Bright Lights) by High-Performance Liquid Chromatography−Electrospray Ionization Mass Spectrometry

Abstract

The betalain pattern of differently colored Swiss chard (Beta vulgaris L. ssp. cicla [L.] Alef. cv. Bright Lights) was investigated for the first time. Nineteen betaxanthins and nine betacyanins were identified by RP-HPLC and positive ion electrospray mass spectrometry, co-injection experiments with semisynthetic reference compounds, and standards derived from authentic plant material, respectively. Histamine-betaxanthin and alanine-betaxanthin were found to be novel betaxanthins, which to the best of our knowledge have not been reported as natural compounds until now. Furthermore, tyramine-betaxanthin (miraxanthin III) and 3-methoxytyramine-betaxanthin, which to date were known only from families other than the Chenopodiaceae, were detected for the first time in colored Swiss chard. The betacyanin pattern of purple petioles was composed of betanin, isobetanin, betanidin, and isobetanidin. Although phyllocactin was present in only trace amounts, further acylated structures such as betanidin-monoferuloyl-5-O-beta-diglucoside and lampranthin II, accompanied by their corresponding C(15)-epimers, were identified. In addition, quantification of betalains and CIE LCh degrees measurements were performed with the colored extracts to correlate the visual appearance with the respective pigment patterns. Besides the novel phytochemical findings, the present study is useful for the evaluation of betalainic Swiss chard as a potential coloring foodstuff.

Characterization of the monophenolase activity of tyrosinase on betaxanthins: the tyramine-betaxanthin/dopamine-betaxanthin pair

“…Purity was confirmed by HPLC analysis with PDA detection. Masses were as expected for the corresponding protonated molecular ions [M+H] + of the pigments: m/z 331 (tyraminebetaxanthin) and m/z 347 (dopamine-betaxanthin), as previously reported (Kugler et al 2004). …”

“…inflorescences ). Tyramine-derived betaxanthin (miraxanthin III) is a betaxanthin also described in Mirabilis jalapa flowers, (Piattelli et al 1965) and in colored Swiss chard (Kugler et al 2004). Fig.…”

“…The derived betaxanthin, dopamine-betaxanthin (miraxanthin V), has been found in Mirabilis jalapa (Piattelli et al 1965), in hairy root cultures from yellow beet , in orange callus cultures of Beta vulgaris (Girod and Zry¨d 1991), in Celosia sp. inflorescences , and in Swiss chard (Kugler et al 2004). Furthermore, a group of betacyanins, the 2-descarboxy-betacyanins, are derived from dopamine instead of DOPA, and are present in flowers of Carpobrotus acinaciformis (Aizoaceae) (Piattelli and Impellizzeri 1970), in hairy root cultures of yellow beet Kobayashi et al 2001), and in Celosia sp.…”

Betaxanthins as Substrates for Tyrosinase. An Approach to the Role of Tyrosinase in the Biosynthetic Pathway of Betalains

“…It had been reported that dopaxanthin was the only pigment in Glottiphylum longum flowers (0.3 mg g 21 ; Impellizzeri et al, 1973). This single pigment composition is not usual in the distribution of betaxanthins, which are frequently reported to appear in mixtures (Piattelli et al, 1965;Kugler et al, 2004). The data published for Glottiphylum were reviewed by using the analytical tools available today, studying in this case the species Glottiphylum oligocarpum and Glottiphylum pigmaeum.…”

First 13C‐NMR Assignments of Betaxanthins

“…Miraxanthin V (2) was first identified in flowers of Mirabilis species, and its structure was elucidated by 1 H-NMR analysis on a 60-MHz spectrometer [9]. According to more-recent reports, this betaxanthin has also been detected in common cockscomb, feathered amaranth, yellow beet, and Swiss chard [16] [23] [24].…”