Evidence for the formation of benzacridine derivatives in alkaline-treated sunflower meal and model solutions

Molecules

Volumn 21, Issue 1, 2016, Pages

  Bongartz, Verena ^a   Brandt, Lisa ^a   Gehrmann, Mai Linh ^a   Zimmermann, Benno F ^a,b   Schulze Kaysers, Nadine ^a   Schieber, Andreas ^a  

^a UNIVERSITY OF BONN   (Germany)

^b Institute Prof Dr Georg Kurz GmbH   (Germany)

Author keywords

Amino acid; Benzacridine derivatives; Chlorogenic acid; Green color; O quinone; Oxidation

Indexed keywords

ACRIDINE DERIVATIVE; ALKALI; AMINO ACID; BENZ(C)ACRIDINE; CATECHOL OXIDASE; CHLOROGENIC ACID; QUINONE DERIVATIVE;

BIOMASS; CHEMISTRY; OXIDATION REDUCTION REACTION; PH; SUNFLOWER;

ACRIDINES; ALKALIES; AMINO ACIDS; BIOMASS; CATECHOL OXIDASE; CHLOROGENIC ACID; HELIANTHUS; HYDROGEN-ION CONCENTRATION; OXIDATION-REDUCTION; QUINONES;

EID: 85000789435     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules21010091     Document Type: Article

References (17)

1. Weisz, G.M.; Schneider, L.; Schweiggert, U.; Kammerer, D.R.; Carle, R. Sustainable sunflower processing-I. Development of a process for the adsorptive decolorization of sunflower [Helianthus annuus L.] protein extracts. Innov. Food Sci. Emerg. Technol. 2010, 11, 733-741. [CrossRef].
2. González-Pérez, S.; Merck, K.B.; Vereijken, J.M.; van Koningsfeld, G.A.; Gruppen, H.; Voragen, A.G.J. Isolation and characterization of undenatured chlorogenic acid free sunflower (Helianthus annuus) proteins. J. Agric. Food Chem. 2002, 50, 1713-1719. [CrossRef] [PubMed].
3. Kammerer, D.R.; Saleh, Z.S.; Carle, R.; Stanley, R.A. Adsorptive recovery of phenolic compounds from apple juice. Eur. Food Res. Technol. 2007, 224, 605-613. [CrossRef].
4. Pierpoint, W. o-Quinones formed in plant extracts: Their reactions with amino acids and peptides. Biochem. J. 1969, 112, 609-616. [CrossRef] [PubMed].
5. Rawel, H.M.; Meidtner, K.; Kroll, J. Binding of selected phenolic compounds to proteins. J. Agric. Food Chem. 2005, 53, 4228-4235. [CrossRef] [PubMed].
6. Le Bourvellec, C.; Renard, C. Interactions between polyphenols and macromolecules: Quantification methods and mechanisms. Crit. Rev. Food Sci. Nutr. 2012, 52, 213-248. [CrossRef] [PubMed].
7. Namiki, M.; Yabuta, G.; Koizumi, Y.; Yano, M. Development of free radical products during the greening reaction of caffeic acid esters (or chlorogenic acid) and a primary amino compound. Biosci. Biotechnol. Biochem. 2001, 65, 2131-2136. [CrossRef] [PubMed].
8. Pedrosa, M.M.; Muzquiz, M.; Garcia-Vallejo, C.; Burbano, C.; Cuadrado, C.; Ayet, G.; Robredo, L.M. Determination of caffeic and chlorogenic acids and their derivatives in different sunflower seeds. J. Sci. Food Agric. 2000, 80, 459-464. [CrossRef].
9. Yabuta, G.; Koizumi, Y.; Namiki, K.; Hida, M.; Namiki, M. Structure of green pigment formed by the reaction of caffeic acid esters (or chlorogenic acid) with a primary amino compound. Biosci. Biotechnol. Biochem. 2001, 65, 2121-2130. [CrossRef] [PubMed].
10. Kroll, J.; Rawel, H.M.; Rohn, S. Reactions of plant phenolics with food proteins and enzymes under special consideration of covalent bonds. Food Sci. Technol. Res. 2003, 9, 205-218. [CrossRef].
11. Prigent, S.V.E. Interactions of Phenolic Compounds with Globular Proteins and Their Effects on Food-Related Functional Properties. Ph.D. Thesis, Wageningen University, Wageningen, The Netherlands, 2005.
12. Prigent, S.V.E.; Voragen, A.G.J.; Li, F.; Visser, A.J.W.G.; van Koningsfeld, G.A.; Gruppen, H. Covalent interactions between amino acid side chains oxidation products of caffeoylquinic acid (chlorogenic acid). J. Sci. Food Agric. 2008, 88, 1748-1754. [CrossRef].
13. García Cárnovas, F.G.; Sánchez, J.V.; Iborra Pastor, J.L.; Lozano Teruel, J.A. The role of pH in the melanin biosynthesis pathway. J. Biol. Chem. 1982, 15, 8738-8744.
14. Clifford, M.N.; Johnston, K.L.; Knight, S.; Kuhnert, N. Hierarchical scheme for LC-MSn identification of chlorogenic acids. J. Agric. Food Chem. 2003, 51, 2900-2911. [CrossRef] [PubMed].
15. Schilling, S.; Sigolotto, C.-I.; Carle, R.; Schieber, A. Characterization of covalent addition products of chlorogenic acid quinone with amino acid derivatives in model systems and apple juice by high-performance liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2008, 22, 441-448. [CrossRef] [PubMed].
16. Ali, M.; Homann, T.; Kreisel, J.; Khalil, M.; Puhlmann, R.; Kruse, H.-P.; Rawel, H. Characterization and modeling of the interactions between coffee storage proteins and phenolic Compounds. J. Agric. Food Chem. 2012, 60, 11601-11608. [CrossRef] [PubMed].
17. Ali, M.; Homann, T.; Khalil, M.; Kruse, H.-P.; Rawel, H. Milk whey protein modification by coffee-specific phenolics: Effect on structural and functional properties. J. Agric. Food Chem. 2013, 61, 6911-6920. [CrossRef] [PubMed].