The application of ion‐pair high performance countercurrent chromatography monitored by off‐line LC‐ESI‐MS/MS injections to study betalain metabolite from Vietnamese red dragon fruit (Hylocereus polyrhizus)

Abstract

The pre‐purified betalain extract from Vietnamese red dragon fruits (Hylocereus polyrhizus) was fractionated by a high performance countercurrent chromatography (HPCCC) device using the ion‐pair forming biphasic solvent of tert‐butylmethylether/n‐butanol/acetonitrile/1% aqueous trifluoroacetic acid (2:2:1:5, v/v/v/v). The J‐type HPCCC centrifuge with a 240g centrifugal force field was able to fractionate seven pigments from a 350 mg enriched crude pigment fruit extract, resulting in purified fractions for qualitative identification by LC‐ESI‐MS/MS. This approach fractionated the main betacyanin epimers namely 15R/15S‐betanin (m/z 551), 15R/15S‐phyllocactin (m/z 637), and apiosyl‐15R/15S‐betanin (m/z 683) from the solely existing betaxanthin indicaxanthin. In addition, few minor betacyanins such as 2’‐apiosyl‐15R/15S‐phyllocactin (m/z 769) were concentrated in a few fractions. That method also allowed the better detection of cacti fruit pigment 15R/15S‐hylocerenin (m/z 695), and 15R/15S‐betanidin 5‐O‐β‐sophoroside (m/z 713). However, the separation of these highly polar compounds was incomplete due to insufficient force of the ion‐pairing effect of trifluoroacetic acid (TFA).

Production of colorant powder from dragon fruit ( Hylocerecus polyrhizus ) peel: Bioactivity, heavy metal contamination, antimutagenicity, and antioxidation aspects

“…(2002) and Thu et al. (2019). The simultaneous occurrence of betanidin‐5‐O‐(6′‐3‐hydroxy‐butyryl)‐β‐glucoside, which gave the red‐purple color, that existed in the dragon fruit peel extract in this study was consistent with the findings of Tenore et al.…”

The adsorption of dragon fruit (Hylocereus polyrhizus) pigments on chitin for food colorants

“…Significantly, differential neutral loss values (Δm/z) observed in MS/MS fragmentation signified distinctive cleavage of sugar units, notably glucose (Δm/z of 162), malonyl (Δm/z of 86), and apiosyl (Δm/z of 132). 27,28 Furthermore, the analysis allowed for the identification of acyl moieties, specifically malonyl-substitution in phyllocactin (Δm/z 86). In Fig.…”

“…Interestingly, only traces of hylocerenin/isohylocerenin (5/5 0 , m/z 695) and betanidin 5-O-⊎-sophoroside (6/6, m/z 713) were recognized in the crude extract, although they are known as the typical betacyanins found in cacti fruits. 1,28,29 The typical yellow betaxanthins of this fruit, indicaxanthin, was detected with [M + H] + at m/z 309, along with the indicative daughter ion at m/z 295. These findings align well with previously published data on pigments present in red dragon fruit.…”

“…These findings align well with previously published data on pigments present in red dragon fruit. 27,28 After adsorption, the LC-ESI-MS chromatogram revealed noteworthy alterations in pigment intensities, signifying a proficient betalain adsorption capacity onto the resin material. Notably, soluble sugars and acids, primarily, exhibited earlier peaks in the chromatogram at higher concentrations compared to their signal intensities in the crude extract (Fig.…”

“…This degradation phenomenon was observed during the solid adsorption of betalains in previous instances. 28 The adsorption mechanism of synthetic dye and biomaterials, such as graphene oxide, demonstrated a notable influence from functional groups, particularly carboxylic and hydroxyl groups present in both the resin and colorant structures. This interaction was observed to involve both π−π interactions and electrostatic interactions.…”