Hydrolysis of chlorogenic acid in apple juice using a p-coumaryl esterase of Rhizoctonia solani.

Publisher: John Wiley & Sons Country of Publication: England NLM ID: 0376334 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1097-0010 (Electronic) Linking ISSN: 00225142 NLM ISO Abbreviation: J Sci Food Agric Subsets: MEDLINE

Publication: <2005-> : Chichester, West Sussex : John Wiley & Sons
Original Publication: London, Society of Chemical Industry.

Chlorogenic Acid/*chemistry ; Esterases/*chemistry ; Fruit and Vegetable Juices/*analysis ; Fungal Proteins/*chemistry ; Malus/*chemistry ; Rhizoctonia/*enzymology; Flavoring Agents/chemistry ; Hydrogen-Ion Concentration ; Hydrolysis ; Odorants/analysis ; Substrate Specificity

Background: Apple juice is rich in polyphenolic compounds, especially in chlorogenic acid. A sour and bitter taste has been attributed to the compound. Chlorogenic acid in coffee powder was quickly hydrolysed by a p-coumaryl esterase of Rhizoctonia solani (RspCAE) at its optimal pH of 6.0. It was unknown, however, if RspCAE would also degrade chlorogenic acid under the strongly acidic conditions (pH 3.3) present in apple juice.
Results: Treatment of apple juice with RspCAE led to a chlorogenic acid degradation from 53.38 ± 0.94 mg L ^-1 to 21.02 ± 1.47 mg L ^-1 . Simultaneously, the caffeic acid content increased from 6.72 ± 0.69 mg L ^-1 to 19.33 ± 1.86 mg/L ^-1 . The aroma profile of the enzymatically treated sample and a control sample differed in only one volatile. Vitispirane had a higher flavour dilution factor in the treated juice. Sensory analysis showed no significant difference in the taste profile ( p < 0.05).
Conclusion: These results demonstrated a high stability and substrate specificity of RspCAE. An increase in caffeic acid and a concurrent decrease in chlorogenic acid concentration may exert a beneficial effect on human health. © 2019 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
(© 2019 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.)

Wirtschaftsvereinigung Alkoholfreie Getränke e.V, Entwicklung des Pro-Kopf-Vebrauchs von alkohlfreien Getränken nach Getränkearten 2012-2018. Wirtschaftsvereinigung Alkoholfreie Getränke e.V, Berlin, Germany (2019). https://www.wafg.de/fileadmin/dokumente/pro-kopf-verbrauch.pdf [27 June 2019].
Kahle K, Kraus M and Richling E, Polyphenol profiles of apple juices. Mol Nutr Food Res 49:797-806 (2005).
Moon J-K and Shibamoto T, Role of roasting conditions in the profile of volatile flavor chemicals formed from coffee beans. J Agric Food Chem 57:5823-5831 (2009).
Fujioka K and Shibamoto T, Quantitation of volatiles and nonvolatile acids in an extract from coffee beverages. Correlation with antioxidant activity. J Agric Food Chem 54:6054-6058 (2006).
Rubach M, Lang R, Seebach E, Somoza MM, Hofmann T and Somoza V, Multi-parametric approach to identify coffee components that regulate mechanisms of gastric acid secretion. Mol Nutr Food Res 56:325-335 (2012).
Rubach M, Lang R, Bytof G, Stiebitz H, Lantz I, Hofmann T and Somoza V, A dark brown roast coffee blend is less effective at stimulating gastric acid secretion in healthy volunteers compared to a medium roast market blend. Mol Nutr Food Res 58:1370-1373 (2014).
Ordynsky G, Über den Geschmack der Chlorogensäure. Z Ernährungswiss 5:203-206 (1965).
Dadic M and Belleau G, Polyphenols and beer flavor. Proc Annu Meet Am Soc Brew Chem 31:107-114 (1973).
Siebert M, Berger RG and Nieter A, Enzymatic mitigation of 5-O-chlorogenic acid for an improved digestibility of coffee. Food Chem 258:124-128 (2018).
Schaefer S, Baum M, Eisenbrand G, Dietrich H, Will F and Janzowski C, Polyphenolic apple juice extracts and their major constituents reduce oxidative damage in human colon cell lines. Mol Nutr Food Res 50:24-33 (2006).
Oboh G, Agunloye OM, Adefegha SA, Akinyemi AJ and Ademiluyi AO, Caffeic and chlorogenic acids inhibit key enzymes linked to type 2 diabetes (in vitro). A comparative study. J Basic Clin Physiol Phamacol 26:165-170 (2015).
Nieter A, Kelle S, Linke D and Berger RG, A p-coumaroyl esterase from Rhizoctonia solani with a pronounced chlorogenic acid esterase activity. New Biotechnol 37:153-161 (2017).
Ochiai N, Sequential stir bar sorptive extraction, in Flavor, Fragnance and Odor Analysis, ed. by Marsili R. CRC Press, New York, NY, pp. 1-19 (2012).
Trapp T, Jäger DA, Fraatz MA and Zorn H, Development and validation of a novel method for aroma dilution analysis by means of stir bar sorptive extraction. Eur Food Res Technol 244:949-957 (2018).
van den Dool H and Kratz PD, A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J Chromatogr A 11:463-471 (1963).
National Institute of Standards and Technology, in NIST Chemistry WebBook. NIST Standard Reference Database Number 69, ed. by, ed. by Linstrom PJ and Mallard WG. National Institute of Standards and Technology, Gaithersburg, MD (2018). https://webbook.nist.gov/chemistry [13 May 2019].
Bel-Rhlid R, Kraehenbuehl K, Cavin C, Raab TW and Page N, Compositions for preparing a coffee beverage comprising hydrolysed chlorogenic acid. Patent WO 2009132887 A1, 2009.
Chen JH and Ho C-T, Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds. J Agric Food Chem 45:2374-2378 (1997).
Vitzthum OG, Thirty years of coffee chemistry research, in Flavor Chemistry: Thirty Years of Progress, ed. by Teranishi R, Wick EL and Hornstein I. Springer, Boston, MA, pp. 117-133 (1999).
Okayasuand H and Naito S, Sensory characteristics of apple juice evaluated by consumer and trained panels. J Food Sci 66:1025-1029 (2001).
Asther M, Estrada Alvarado MI, Haon M, Navarro D, Asther M, Lesage-Meessen L et al., Purification and characterization of a chlorogenic acid hydrolase from Aspergillus niger catalysing the hydrolysis of chlorogenic acid. J Biotechnol 115:47-56 (2005).
Nieter A, Kelle S, Linke D and Berger RG, Feruloyl esterases from Schizophyllum commune to treat food industry side-streams. Bioresour Technol 220:38-46 (2016).
Kraehenbuehl K, Page-Zoerkler N, Mauroux O, Gartenmann K, Blank I and Bel-Rhlid R, Selective enzymatic hydrolysis of chlorogenic acid lactones in a model system and in a coffee extract. Application to reduction of coffee bitterness. Food Chem 218:9-14 (2017).
Nieter A, Kelle S, Takenberg M, Linke D, Bunzel M, Popper L et al., Heterologous production and characterization of a chlorogenic acid esterase from Ustilago maydis with a potential use in baking. Food Chem 209:1-9 (2016).

Keywords: Rhizoctonia solani; apple juice; chlorogenic acid; p-coumaryl esterase

0 (Flavoring Agents)
0 (Fungal Proteins)
318ADP12RI (Chlorogenic Acid)
EC 3.1.- (Esterases)

Date Created: 20190721 Date Completed: 20191031 Latest Revision: 20200108

20231215

10.1002/jsfa.9940

31325326