Thermal Decarboxylation of Betacyanins in Red Beet Betalain-Rich Extract

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ORIGINAL ARTICLE

Thermal Decarboxylation of Betacyanins in Red Beet Betalain-Rich Extract

Agnieszka Kumorkiewicz ¹

,

Katarzyna Sutor ¹

,

Boris Nemzer ²

,

Zbigniew Pietrzkowski ³

,

Sławomir Wybraniec ¹

1

Department of Analytical Chemistry, Institute C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, Cracow 31-155, Poland

2

Chemistry Research, VDF FutureCeuticals, Inc. Momence, IL 60954, USA; Food Science and Human Nutrition, University of Illinois at Urbana-Champaign, Urbana IL 61801, USA

3

ABC Clinical Research, FutureCeuticals, Inc., 23 Peter Canyon Rd, Irvine, CA 92606, USA

Submission date: 2019-09-17

Final revision date: 2019-11-22

Acceptance date: 2019-11-28

Online publication date: 2019-12-17

Publication date: 2020-02-12

Corresponding author

Sławomir Wybraniec

Department of Analytical Chemistry, Cracow University of Technology, Poland

Pol. J. Food Nutr. Sci. 2020;70(1):7-14

DOI: https://doi.org/10.31883/pjfns/114897

References (33) Citations (12)

KEYWORDS

decarboxylation

betalain-rich extract

decarboxy-betacyanins

TOPICS

Liquid chromatography

Functional foods

Food bioactives

ABSTRACT

Betalains are one of the most common groups of plant pigments found in nature, especially in red beetroot (Beta vulgaris L.) which is the main commercially exploited source of betalains produced in the form of concentrates or powders. This report presents results of thermal decarboxylation studies on betacyanins present in a specifically purified highly concentrated betalain-rich extract (BRE). The first tentative structures formed by decarboxylation of the main pigment present in BRE, betanin and its diastereomer, were established by means of liquid chromatography coupled to diode array detection and electrospray ionization tandem mass spectrometry (LC-DAD-ESI-MS/MS). In the extract, two new isomeric bidecarboxylated betanins were tentatively identified. A high rate of generation of 2-decarboxy-betanin/-isobetanin which are present in the BRE extract at very low level was observed, which was dependent on the starting concentration of the BRE substrate. The bidecarboxylated derivatives were generated at a higher rate mostly from 17-decarboxy-betanin/-isobetanin as well as 15-decarboxy-betanin by further decarboxylation at carbon C-2. Further studies will be performed to demonstrate if the decarboxylated betanins being products of heating B. vulgaris preparations can be used for various food applications with new health-promoting actions and colorant properties.

FUNDING

This research was financed by Polish National Science Centre project for the years 2018-2021 (Project No. UMO-2017/27/B/NZ9/02831).

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CITATIONS (12):

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Thematic Issue on “Red Beetroot as a Source of Nutrients, Bioactive Compounds and Pigments”
Wiesław Wiczkowski
Polish Journal of Food and Nutrition Sciences

2.

Phytochemical Molecules from the Decarboxylation of Gomphrenins in Violet Gomphrena globosa L.—Floral Infusions from Functional Food
Natalia Drobnicka, Katarzyna Sutor, Agnieszka Kumorkiewicz-Jamro, Aneta Spórna-Kucab, Michał Antonik, Ewa Dziedzic, Tomasz Świergosz, Joanna Ortyl, Sławomir Wybraniec
International Journal of Molecular Sciences

3.

A dopamine-based biosynthetic pathway produces decarboxylated betalains in Chenopodium quinoa
Paula Henarejos-Escudero, Luis Contreras-Llano, José Lozada-Ramírez, Luz Gómez-Pando, Francisco García-Carmona, Fernando Gandía-Herrero
Plant Physiology

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Multi-colored shades of betalains: recent advances in betacyanin chemistry
Agnieszka Kumorkiewicz-Jamro, Tomasz Świergosz, Katarzyna Sutor, Aneta Spórna-Kucab, Sławomir Wybraniec
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5.

Dehydrogenation of Betacyanins in Heated Betalain-Rich Extracts of Red Beet (Beta vulgaris L.)
Katarzyna Sutor-Świeży, Michał Antonik, Justyna Proszek, Boris Nemzer, Zbigniew Pietrzkowski, Łukasz Popenda, Tomasz Świergosz, Sławomir Wybraniec
International Journal of Molecular Sciences

6.

Influence of Citrates and EDTA on Oxidation and Decarboxylation of Betacyanins in Red Beet (Beta vulgaris L.) Betalain-Rich Extract
Katarzyna Sutor-Świeży, Justyna Proszek, Łukasz Popenda, Sławomir Wybraniec
Molecules

7.

Antioxidant Capacity, Antitumor Activity and Metabolomic Profile of a Beetroot Peel Flour
Pedro Coimbra, Anna Silva-e-Silva, Ananda Antonio, Henrique Pereira, Valdir Veiga-Junior, Israel Felzenszwalb, Carlos Araujo-Lima, Anderson Teodoro
Metabolites

8.

Ultrasound-Assisted Water-in-Oil Emulsions for the Microencapsulation of Beet Extract (Beta Vulgaris L.) by Spray Chilling Technique
Júlia Antonio, Amanda Lago, Jayne Figueiredo, Natália Oliveira, Victor Silva, Amanda Lopes, Guilherme Carneiro, Joyce Costa, Soraia Borges
SSRN Electronic Journal

9.

Beta vulgaris L.—A Source with a Great Potential in the Extraction of Natural Dyes Intended for the Sustainable Dyeing of Wool
Vasilica Popescu, Alexandra Blaga, Dan Cașcaval, Andrei Popescu
Plants

10.

Unveiling Alternative Oxidation Pathways and Antioxidant and Cardioprotective Potential of Amaranthin-Type Betacyanins from Spinach-like Atriplex hortensis var. ‘Rubra’
Agnieszka Kumorkiewicz-Jamro, Renata Górska, Małgorzata Krok-Borkowicz, Przemysław Mielczarek, Łukasz Popenda, Kateryna Lystvan, Elżbieta Pamuła, Sławomir Wybraniec
Journal of Agricultural and Food Chemistry

11.

Oxidative decarboxylation of arylacetic acids and arylacetic esters with singlet molecular oxygen generated from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate
Z Najminejad
Journal of Chemical Sciences

12.

Enhancing betacyanin stability: Comparison of dragon fruit (Hylocereus polyrhizus) pulp and peel powders through encapsulation technology during storage
Bambang Nurhadi, Muhammad Abdillah Hasan Qonit, Syariful Mubarok, Rudy Adi Saputra
Food Science & Nutrition

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