Cardelle-Cobas, Alejandra

Corzo, Nieves

García-Bermejo, Ana B.

Olano, Agusín

Ruiz-Matute, Ana I.

English

Repositório Institucional da Universidade Católica Portuguesa

INTRODUCTION Among the different strategies studied to improve chitosan solubility and extend its applications, one very promising approach is the synthesis of carbohydrate-chitosan derivatives through Maillard Reaction (MR). This reaction has potential industrial application since it is easy to control and may occur readily in the absence of solvent. In a recent work, our group has studied the effect of different drying methods on chitosan reactivity towards MR during storage of dried chitosan-lactose systems and modified chitosans were obtained [1]. MR development was assessed by quantification of a new compound formed during the acid hydrolysis of Amadori compounds resulting from the  chitosan-lactose interactions (NFMD).  Table 1.- Solubility, water (WBC) and fat binding capacities (FBC) of chitosan and its lactose derivative (obtained after 48h of storage at 60ºC and aw=0.65 ). CONCLUSIONS REFERENCES ACKNOWLEDGEMENTS The objective of the present work was to determine the solubility, water and fat-binding capacity and antioxidant activity of native chitosan and compared to those of chitosan-lactose derivatives obtained via Maillard reaction. OBJECTIVE STUDY OF FUNCTIONAL PROPERTIES OF CHITOSAN-LACTOSE DERIVATIVES OBTAINED BY MAILLARD REACTION Ana I. Ruiz-Matutea, Ana B. García-Bermejoa, Alejandra Cardelle-Cobasa,b, Agustín Olanoa, Nieves Corzoa*  aInstituto de Investigación en Ciencias de la Alimentación CIAL (CSIC-UAM), Madrid, Spain, bCurrent address: CBQF - Centro de Biotecnologia e Química Fina, Escola Superior de Biotecnologia, Centro Regional do Porto da Universidade Católica Portuguesa, Porto, Portugal. *corresponding author: nieves.corzo@csic.es  Under assayed conditions, the interaction of lactose with chitosan gives rise to a derivative with improved solubility, and water and fat-binding capacity.  Higher concentrations of chitosan-lactose derivative also enhanced the antioxidant activity. This work was financed under the projects AGL 2008-00941/ALI, CYTED P109AC0302 and ALIBIRD-CM-P 2009/AGR 1469. Ana I. Ruiz-Matute thanks her JAE Doc contract from CSIC. FUNCTIONAL PROPERTIES SOLUBILITY  (mg/mL) pH 7, 20ºC WBC (%) FBC (%) PURIFIED CHITOSAN 1.5 ± 0.4 1083.5 ± 195.9 2646.6 ± 22.8 CHITOSAN-LACTOSE DERIVATIVE 6.8 ± 0.5 3944.5 ± 1011.4 8124.6 ± 399.7 [1] García-Bermejo, A. B., Cardelle-Cobas, A., Ruiz-Mature, A. I., Montanes, F., Olano, A., Corzo, N. (2012). Effect of drying methods on the reactivity of chitosan towards Maillard reaction. Food Hydrocolloids, 29: 27-34.                    .  Chitosan-lactose derivative exhibited an improvement in all of the functional properties studied comparing to those of native chitosan.   Solubility increased in the chitosan-lactose derivative respect to that of the native chitosan from 1.5 to 6.8 mg/mL. WBC and FBC were also higher in the derivatives, varying from 1084 % to 3945% and from 2647 % to 8125 %, respectively.  These chitosan-lactose derivatives with modified properties could be considered as very promising for their future use as additives in the food industry.  Maillard reaction development was assessed by quantification of a new compound originated from the acid hydrolysis of Amadori compounds (NFMD) resulting from chitosan-lactose interactions and not detected in the acid hydrolysates of freshly prepared chitosan-lactose systems (Figure 1).  Under controlled conditions, the highest level of NFMD formed (428.45 mg/100g) was obtained after 48 h storage (Figure 2). CHITOSAN DERIVATIVE FORMATION Figure 1. RP-HPLC-UV profiles of furosine standard, and acid hydrolysates of chitosan (control) and chitosan–lactose derivative. Figure 2. Formation (mg/100g of product) of the new furoylmethyl derivative (NFMD) during storage at 60ºC and aw 0.65 of chitosan-lactose system CHROMATOGRAPHIC ANALYSIS SOLUBILITY FAT BINDING CAPACITY (FBC) WATER BINDING CAPACITY (WBC) FUNCTIONAL PROPERTIES 10 mg chitosan + 1 mL distilled water Adjust pH to 7 with NaOH Stirring, 30 min, 20ºC Centrifugation (7000g, 20 min) Lyophilization weight 500 mg chitosan + 10 mL distilled water 500 mg chitosan + 10 mL soybean oil Centrifugation (8000g, 40 min) Centrifugation (8000g, 40 min) weight weight WBC (%)= [water bound (g)/sample weight (g)] × 100 FBC (%)= [fat bound (g)/sample weight (g)] × 100 20ºC, 30 min ( stir 5 s every 10 min)  20ºC, 30 min  ( stir 5 s every 10 min)  C18 column (250 x 4.6 mm i.d.)   Room temperature Mobile phase: 20% acetonitrile, 0.2% formic acid and 5mM sodium heptanesulfonic acid solution Flow rate: 1.2 mL/min Wavelength: 280 nm  ANTIOXIDANT  ACTIVITY ABTS 0.1 g of sample + 8 mL 8N HCl  110ºC/23 hours Hydrolysis under inert conditions  Filtration through  Whatman nº40    0.5 mL of the filtrate Sep-Pack C18 Elution with 3 mL 3N HCl 100 mL                         evaporated and reconstituted In mobile phase for HPLC analysis Purification SAMPLE PREPARATION Chitosan-lactose solution in 1% acetic acid (0, 0.2, 0.5, 1, 5 and 10 mg/mL) 0.4 mL sample  + 3mL of 0.1 mmol/L DPPH radical methanolic solution  Storage: 30 min at room temperature in the dark PowerWaveTM XS Microplate spectrophotometer  (BioTek)  Scavenging effect (%) = [(1 − Asample)/Acontrol] × 100%   10 µL sample  + 1 mL ABTS radical aqueous solution (7mM ABTS + 2.45mM potassium persulfate, room temperature, 16h)  Room Temperature  (30 min) 734 nm 517 nm Instituto de Investigación en Ciencias de la Alimentación  0 2 4 6 8 10 12 14 16Furosine Chitosan-lactose derivative Chitosan Furoyl-amino compound   Figure 3. % of ABTS radical scavenging activity after 30 min of reaction of: native purified chitosan and chitosan-lactose derivative (obtained after 48h of storage at 60ºC and aw 0.65). 0 5 10 15 20 25 30 0 2 4 6 8 10 12 Concentration (mg/ml) Scavening effect (%) Chitosan-lactose Chitosan ABTS 0 5 10 15 20 25 30 0 2 4 6 8 10 12 Concentration (mg/mL) Scavening effect (%) Chitosan Chitosan-lactose Figure 4. % of DPPH radical scavenging activity after 30 min of reaction of: native purified chitosan and chitosan-lactose derivative (obtained after 48h of storage at 60ºC and aw 0.65).  Similar results were obtained for % of ABTS (Figure 3) and DPPH (Figure 4) radical scavenging activity of native purified chitosan and chitosan-lactose derivative. Chitosan-lactose derivative showed similar antioxidant activity to that of native chitosan, being slightly higher at concentration of 10 mg/mL.. DPPH CHITOSAN DERIVATIVE SYNTHESIS Raw chitosan Purified chitosan Microspheres  of chitosan Chitosan Lyophilization Storage under vacuum Temperature: 60ºC Water activity: 0.65 Time: 48 hours  Lactose addition Lactose Conditions: Dialysis (Purification of chitosan-lactose derivative) ION PAIR RP-HPLC-UV  DPPH FUNCTIONAL PROPERTIES MATERIALS AND METHODS RESULTS ANTIOXIDANT ACTIVITY 

Study of Functional properties of chitosan-lactose derivatives obtained by Maillard reaction

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Study of Functional properties of chitosan-lactose derivatives obtained by Maillard reaction

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