International Food Research Journal 19(4): 1581-1587 (2012

)
Journal homepage: http://www.ifrj.upm.edu.my

Flavonoid, phenolic contents and antioxidant properties of Thai hot curry paste
extract and its ingredients as affected of pH, solvent types and high temperature
1
Settharaksa, S., 1Jongjareonrak, A., 1Hmadhlu, P., 1Chansuwan, W. and
2,*
Siripongvutikorn, S.
1
Nutraceutical and Functional Food Research and Development Center,
2,*
Department of Food Technology, Faculty of Agro-Industry, Prince of Songkla
University,
Hat Yai, Songkhla Thailand 90112

Article history Abstract

Received: 10 November 2011 Spices used in curry pastes containing phenolics and flavonoids have been reported to prevent
Received in revised form: oxidative stress related diseases. Thai hot curry, Kua-khling curry paste, a Thai traditional
1 March 2012 seasoning particular Thai-Muslim, was investigated as potential functional food. In the present
Accepted:1 March 2012
study, the flavonoid, phenolic contents and antioxidant activities of extract from spices used in
the paste were determined. The effect of pH, solvent type and temperature (100-121oC) were
investigated after the samples were extracted. It was found that the extracts of spices presented
flavonoid and phenolic contents in the range 0.04-11.18 mg catechin equivalent (CE)/100 g
Keywords
sample and 0.68-134.91 mg gallic acid equivalent (GAE)/100g sample, respectively. Antioxidant
Hot curry paste
activities determined as DPPH radical scavenging activity, hydroxyl radical scavenging activity
antioxidant activity (HRSC) and ferric reducing antioxidant power (FRAP) of the extracts were 0.49-8,214.91
flavonoid content mg GAE/100g sample, 0.69-9.30 mg GAE/100g sample and 25.83-6,860.55 mg GAE/100
phenolic content g sample, respectively. The best solvent for extraction was water since its yielded flavonoid
spices and phenolic contents and DPPH activity as 61.03±6.22 CE/100 g, 964±79.13 GAE/100g and
1,740.84±13.57 GAE/100g, respectively. Flavonoid, phenolic contents and DPPH activity
were decreased at pH lower and higher than pH 6. However, it was found that temperature at
100oC caused more depletion of flavonoids, phenolic contents and DPPH activity compared
with heating 121oC. Therefore, thermally canned food may have a potential for health benefit
as evaluated by antioxidant properties in vitro system.

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Introduction as curry paste. Moreover, those results are usually
difficult to directly compare, because of the season of
Spices and herbs have been effectively used in plant samples, test methods and solvent used.
the indigenous systems of medicine and human food Typical phenolics that possess antioxidant activity
in India and also in other countries (Satia-Abouta, are mainly phenolic acids and flavonoids. Phenolic
2002). In addition, spices and herbs are reported to acids are a major class of phenolic compounds,
contain bioactive compounds imparting antioxidant, widely containing in the plant kingdom especially in
preservative and antimicrobial properties to the food. fruits and vegetables. However, phenolic compounds
Many spices and herbs contain a number of phenolic in plant foods are presented in free and bound forms
and flavonoid compounds, having antioxidant through ester, ether, or acetal bonds (Robbin, 2003).
(Shobana et al., 2000) antiinflammatory (Ach et And it is assumed that many antioxidative phenolic
al., 1994) antimutagenic (Muralidhara, 1998) and compounds in plants are usually presented as a
anticarcinogenic activities (Menon et al., 1999). Some covalently bound form; therefore, some processing
studies have been reported that phenolic compounds methods were employed to release them so as to
in spices and herbs significantly contributed to their enhance the antioxidant capacity (Seung-Cheol
antioxidant (Siripongvutikorn et al., 2008; Saeh et et al., 2005). For example, it was reported that
al., 2010) and pharmaceutical properties (Srinivasan heat treatment may liberate some low molecular
et al., 2005). Though, individual spices/herbs were weight phenolic compounds and hence increase
addressed as food additives, few scientific data have the antioxidant capacity of citrus peel (Seok-Moon
been reported about combination of spices/herbs et al., 2004). However, the effect of heat treatment

*Corresponding author.
Email: sunisasiripongvutikorn@gmail.com

defatted and evaporated as mentioned bejolghota). cumin (Cuminum cyminum L. scavenging activity.. ml of 50% (v/v) aqueous methanol with acidified 0. cinnamon. Plant materials and samples preparation Effect of pH The Kua-khling paste consists of cayenne pepper Spices/herbs (100 g) were ground and (Capsicum frutescens). The use of an alcoholic solution provides satisfactory results for Some flavonoid and phenolic compounds the extraction process (Perv-Uzulanic et al. A gradient solvent anise while Thai-Muslim does.. The phenolic extracts of plants are always a evaporated at 50oC under reduce presure to obtain mixture of different classes of phenols. identification by HPLC analysis The ethanol extract of lemon grass exhibited anti. antioxidant properties of Kua-khling curry paste and The mixtures were then brought to centrifuge. 70% to 80% particularly odor attribute. the negative smell. 2003).99% (v/v) ethanol without acidified 0.1% HCl. The mixtures were then stirred. of dish may differ from home to home or region to Flavonoid and phenolic contents were region (Siripongvutikorn et al. the objective of this investigation was homogenized in 50 ml of water.1582 Settharaksa et al./IFRJ 19(4):1581-1587 on citrus flavonoids was not involved.6mm) with a seafood. Furthermore.). 2008). 2 N HCl in 50% methanol and heating at 90oC for 90 However. C18 guard column. 20 and 30 min.. star anise above to obtain the dried samples. All ingredients were bought from grocery shop Spices/herbs (100 g) were ground and or fresh market in Hat-Yai. the characterized and quantified by HPLC using difference of spices used in cooking style usually modified chromatographic conditions of (Talcott et depend on protein base used as red meat. sheep. Spices/herbs were extracted with 25 g of 50% mutagenic activity (Vinitketkumnuen et al. The hot and spicy curry paste named Kua. ingredients composition of identical name min.) and camphor seed (Ammomum testa Effect of temperature ceum). selectively soluble in the solvents. total phenolic contents and then stirred for 12 h in dark room for extraction. garlic (Allium (100 mM. or white or light meat as chicken and Eclipse XDB-C18 column (250mmx4. Mobile phases consisted of water khling of Thai-Buddhist does not add some strong (Phase A) and 60% methanol (Phase B) both adjusted flavor spices as cumin. al. nutmeg (Myristica fragrans). shallot (Allium ascalonicum homogenized in 100 ml of acetate phosphate buffer L. It is well known that program ran phase B from 0% to 30% in 3min. lemon with the solvent. (Illicium verum Hook).). Then a and supernatant was collected then defatted with further investigation was needed (Guihua et al. 1994). its ingredients. Samples were further love to consume hot and spicy dish as curry or dip aided following acid hydrolysis into aglycones using particularly in the southern and northeast part. As mentioned above. 5. and held for 10 derived from some spices is selected to mask or change min all at 0. pH 2-10) and stirred for 2 h then extracted sativum).. Kua-khling curry paste consists of many spices and herbs may Effect of solvent types possess antioxidant activity and medicinal property.8 mL/min (Pozo-Insfran et al. kaffir lime fruit peel (Citrus hystrix). 25%. turmeric powder (Curcuma longa). Each dried sample extracted with Materials and Methods various solvent types was subjected to analyze. 10.1% 3. Thais 12 h to dissolve polyphenolics. pepper (Piper nigrum L. defat and evaporate to obtain solid sample as mentioned above. Moreover. hexane 3 times. total phenolic contents and DPPH radical galangal L. 30% sex hormone of goat has effect on its meat quality to 50% in 5 min.). some aroma in 5 min. 50%.. and 80% to 100% in 5 min. goat.). 2006). 75% and to study the effect of solvent. (w/v) aqueous methanol acidified with 0.1% HCl. Separations were performed on a Zorbax beef or buffalo. Each homogenized in 100 ml of water and heated in ingredient (100 g) was ground and homogenized in 50 water bath at 100 oC and 121 oC in oil bath for 1.. . cinnamon (Cinnamomum centrifuged. which are solid matter. 50% to 70% in 17 min. Songkhla Thailand. Spices/herbs (100g) were ground and Therefore. conditions on flavonoid. nutmeg and star to pH 2. to extract with selected solvent as mentioned before. galangal (Alpinia flavonoid. Thailand is claimed as kitchen of the world as Homogenized samples were allowed to extract for a planet of animals and plants. pH and temperature 99. The defatted supernatant was then 2007). which exhibited the highest grass (Cymbopogon citratus). and no clear The mixture was centrifuged at 8000 x g for 20 min quantity relationships were elucidated. The mixtures were brought HCl and stirred for 12 h in dark room for extraction. Therefore. 2006).4 with o-phosphoric acid. coriander seed (Coriandrum sativum L.

46±5. Results were expressed as µl/ml of Chemical analyses gallic acid equivalents (GAE) per 100 g sample.03±88. Results were expressed as µl/ml 3.02±3. Lemon grass 4.46j of gallic acid equivalents (GAE) per 100 g sample.02b 1.23d 85.214. The absorbance was at 595 nm.) The absorbance was 1.17c 5.15c 2.83±1.009 seed i 3.35±0.131. All determinations were and acidified with HCl are shown in Table 1.860.04±0. The reagent (270 µl) was mixed with determinations were performed in triplicates.47b green reagent was added into the mixture and Values are means of three replicate determination ±standard deviations subsequently incubated for 10 min.07±0.71d 1.31±0.52 4.736.53±0. pH 3. sample solutions (30 µl) before subjected to measure absorbance at 595 nm after the mixture was incubated Determination of flavonoid compounds for 30 min in the dark room.61±0.05g 3.94c All determinations were performed in triplicates.14±29.27±0.12±54.53±1.92±0.37±18.12±0. component depends on degree of polarity and ratio of (1999).03d 9. Shallot 1. In general.55±91.97cd 337. the latter forms a blue 6 min.39b 1.55±0. Star anise 4.63±3.64 d 2.016.08±21.49±0. Then 15 µl of triplicates (Benzie and Strain.46 b Hydroxyl radical-scavenging assay 8. evaporate as mixed with sample solutions (25 µl).67±0. This may be due to suitable DPPH radical-scavenging activity of solvent to mixture extractability compared with The DPPH radical-scavenging activity was individual material.630.28c 0.15d 5.0039 g of 2.56±0. (The mixture of DPPH reagent was content �mg content �mgGAE/100g scavenging activity �mgGAE/100g radical scavenging reducing antioxidant shaken vigorously and allowed to stand at ambient CE/100g sample� sample� sample� assay �mgGAE/100g powder �mgGAE/100g sample� sample� temperature in the dark for 3 h.13±0. The total Total phenolic.83±6.18c 9. Galangal 0.38h measured at 517 nm after 30 min of incubation at 2.03 paste a 34. total phenolic contents and antioxidant activities of with 0.50 g contained 100 µl of ferric sulphate (0.01e 6.50 g 6.70a dark room for 5 min.006d 41.64±0. Cumin 3. Coriander 0.06±2. 1997).63±0.03f 1. 4.17±0.5 µl of Folin-Ciocalteau reagent for (Fe3+) to the ferrous ion (Fe2+).81±102.Kua-khling 81.19±2.05 d 1. Standard curve was The content of flavonoids was determined by prepared using different concentration. Briefly. a solution room temperature.96±0.03i 1.91±5. Cayenne pepper 2. 125 µl of 7% sodium carbonate (NaCO3) and complex (FE/TPTZ). and 20 µM FeCl3 at gallic acid equivalents (GAE) per 100 g sample.04c 3.61±22.443. the FRAP reagent was prepared measure at 760 nm after 90 min of incubation at by mixing acetate buffer (300 µM. All determinations were performed in sodium nitrate (NaNO3) for 6 min.16e 11.96±0.5 mM) and 75 11.72 i µl of 3% hydrogen peroxide was incubated in the 12.17def 1.03de 1.07g h 1.62±0.009d 786. Cinnamon 13. Garlic 3.462.56 d 1.57±0. Kaffer lime b 0.876.80±0. The extracted samples (25 µl) expressed as µl/ml of trolox equivalents (TE) per were mixed with 125 µl of water and 10 µl of 5% 100 g sample.60f 0.004c 418.94±0. 2-diphenyl-1-picrylhydrazyl spice and herb extracts which added 50 ml of absolute ethanol to obtain Herbs/Spices Flavonoid Total phenolic DPPH radical Hydroxyl Ferric 200 µM.00h 0.15g h 1.87±6. The absorbance of the solution at a wavelength of 510 nm was detected.26b 745.04e 560.13c 5.68±0.86j room temperature.01g 3. Settharaksa et al.19c 606. The reaction mixture 10.90±29.95±0. extractability of any determined by the method of Brand-Williams et al.30±0. Camphor seed 0.19a 198.31±0. 1996). Total phenolic content was determined by the Folin-Ciocalteau method (Slink and Singleton.002g 25.88±4.11def 3. Nutmeg 1. The absorbance mentioned above.5 µl) were mixed with 50 A potential antioxidant will reduce the ferric ion µl of water.73±0.01±0. All 10:1:1 (v/v/v).92±0.18±0.53±0.37 d 7.29±0.74±0.33±0.43±21.82e 14.59±7.45±3.01h 328.12d 408.03g 134.47 a 724.01j Sminoff and Cunbes (1994). the result showed that Kua-khling curry paste was highest in total flavonoid as 81.35±21.76±25.60±0.26b 1.26a 0.87±0.12f 0.61 c 5. flavonoid contents and antioxidant flavonoid content in each spice extract was then activities calculated using a standard curve prepared with Flavonoid.435 mM brilliant fruit peel h 3. performed in triplicates. Surprising.96±2.04g 49./IFRJ 19(4):1581-1587 1583 The extracts were brought to defat. 5. 10% aluminum chloride was added and stand for 5 min before 50 µl of 1 M sodium hydroxide was Results and Discussion added sequentially.08b 114.6). total phenolic contents and antioxidant catechin and expressed as µl/ml catechin equivalents activities of each ingredient extracted with methanol (CE) per 100 g sample. Results were Chen and Li (2007). The extracted samples (100 µl) were mixed Table 1 Flavonoid.69±0.17ef 1. Turmuric powder 2.03i 326.007f 467. which increases the absorption 100 µl of water then added. 50 µl of 0.01f 6.11ef 8. 12. Results were express as µl/ml of of 10 µM TPTZ in 40 µM HCl.74±2.36±0. was measured at 624 nm after incubation for 10 min in the dark room.74 f The assay was determined by the method of 9. Ferric reducing power (FRAP) assay The extracted samples (12.91±402.87±0.44±0.35±0.39b 1.03 Determination of antioxidant activities mg CE/100 g sample.62±0.316. All Determination of total polyphenolic compounds determinations were performed in triplicates. The reagent was a-j means with a column with the different letters are significantly different .

Generally. flavones. linolic acid at high concentrations (Wang. high when compared with ethanol and methanol catechin and other phenolics were the majority of plus HCl extraction. 2002). (2000) phenolic content but was lower than methanol plus reported the cinnamon has the structural feature HCl as flavonoids.47 and as effect of solvent types are shown in Table 2. 0.007. comparable to that of ferulic solute and solvent.1584 Settharaksa et al.57±0. (2010) reported that water extraction of plant some ingredients were increased or decreased the organs leaves a large amount of residual polyphenols holistic characters of the active ingredients might that only an appropriate combination of solvents be changed.860. In addition DPPH with a mixture of suitable solvents.23±0. Therefore. gallic acid and catechuic as 0. methanol acidified with HCl.49±0. It meant that combination of the acid. Caffeic acid was found to have high antioxidant quality. quercetin. 27.006. quercetin.007. there was difficult to get khling curry paste correlated with flavonoid and correlation between neither flavonoid nor phenolic total phenolic content.1.007. Koffi et paste to serve the optimum purpose.. Moreover.. However. Several studies revealed obtaining from water extraction was also equally those flavonoids. Dorman et al.29±0. Flavonoid. Furthermore. respectively. A similar characteristic had and antioxidant activities (Table 1). flavonoid structures containing an electron repelling group in or-tho are more less polarity compared with phenolic position to the phenolic group requited for a strong free acid. 1999). coumalic acid.70 mg GAE/100 g sample respectively found that using water as extracted solvent was better while coriander seed extract showed highest the DPPH than ethanolic solvents in term of flavonoids and total radical scavenging activity. coumalic acid and catechin. and chemical behavior. pH and heat treatment on antioxidant activity in the curry paste.17±0. This may be the reason for ancient wisdom extraction procedure compare with 70% ethanol and of using many ingredients in folk medicine or cooking methanol (Ollanketo et al. where each ingredient possessed different antioxidant water extraction was found to be the most effective property. total phenolic contents and DPPH radical scavenging activity on the paste Lee. the DPPH (1. 0. would extract. It pointed out that gallic acid and quercetin were major active component in this curry paste. if al. While.55±0.55±91. 2003). It appears that the vast majority of diphenyl-2-picrylhydrazyl). DPPH radical scavenging activity has been used as antioxidant activity assay as its diversity.assay is complexity of polyphenols are not water soluble. to be the analyzed substrates. anthocyanin. The amount of polyphenols was also dependent on the extraction method (Kim and Figure 1 Effect of pH on flavonoid.91±5. As basic knowledge. Ferulic ingredients as the paste reached or closed to polarity acid was reported to inhibit the photo-peroxidation of of the solvent used. Values are means of three replicate determination ±standard deviations a-f means with a column with the different letters are significantly different HPLC analyses In this present work./IFRJ 19(4):1581-1587 Table 2 Effect of solvent type on flavonoid.007. DPPH radical scavenging activity was selected to study the effect of solvent type. 2004). 4. catechin.49±0.. (1995) reported that the methanolic solvent was better for catechin. epicatechin and Effect of solvent type epigallocatechin extraction. often mixtures of dozens assured of obtaining fractions rich in polyphenols of compounds with different functional groups. been reported for antioxidant activity of sage. frequently employed and accurate method. total phenolic contents and DPPH Cinnamon powder possessed the highest of total radical scavenging activity of the curry paste extracts phenolic content and FRAP as 134. total phenolic contents and delocalization over the whole molecule (Szabo et al. Therefore. Therefore. isoflavones. 8.045 µg/g. caffeic acid. the RP-HPLC peaks of the paste extract were identical with the peak of ferulic acid. is a stable free radical because of its spare electron . It was 6. Using water as solvent extract the antioxidant activity of plant material (Kahkonen made DPPH radical scavenging activity of Kua- et al.007 and 4. Kallithraka et al. In general. manufacturers would have to use extraction solvents polarity. DPPH radical scavenging activity of the paste 2007). DPPH radical scavenging activity radical-scavenging activity.

On the Effect of pH other hand. Kim et al. and used parts as leaf. fresh or dried from sample. the flavonoid content and antioxidant activity at 121oC was higher than heating at 100oC. 2006).. Effect of temperature Effect of heating temperature and time on flavonoid. However. DPPH radical scavenging activity of this curry paste depended on flavonoid content not phenolic content. total phenolic contents and antioxidant activity are presented in Figure 2. polar compounds. compounds to soluble phenolics. basic condition. It meant that the active compounds were heat labile or easily destroyed fragment by heat. DPPH radical scavenging activity of heated extract paste at 121oC was higher. Using radical scavenging activity of different extracts . it confirmed that flavonoid Therefore. phytochemical components in each plant depends on whatever that it is waxy or non waxy species part. 1999). These differences may be due to different samples used and various compounds being extracted in each case./IFRJ 19(4):1581-1587 1585 from cocoa by products was higher at alkaline pH (Azizah et al. The antioxidant activities of different extracts indicate strong dependence of Conclusions DPPH radical scavenging activity on the pH of the system. heating at 200°C decreased the total phenolic content of WGSE and PGSE significantly (p<0. total phenolic contents scavenging activity at neutral and acid pH. non polar molecule and simple phenolics. flavonoid. as well as the selected compound such as carotenoids. Settharaksa et al. (2006) concluded that the total phenolic content in whole grape seed extract (WGSE) Figure 2 Effect of heating temperature and time on flavonoid content and powdered grape seed extract (PGSE) were (a). As our knowledge. total phenolic contents and DPPH radical scavenging activity. (2005) who reported that DPPH radical scavenging activity in basil heating at 120oC was higher than heating at 80oC and 100oC. Xu et al. Surprising. heating temperature at 121oC reduced less flavonoid than heating at 100oC. total phenolic content (b) and DPPH radical scavenging activity (c) of the paste significantly increased by heat treatment. which indicated that are shown in Figure 1. It was found that increased heating time reduced flavonoids. Yen and Duh (1993) reported that a methanol All ingredients used in the Kua-khling curry extract from peanut hulls had a higher DPPH radical paste possessed flavonoid. fruit or bark.05). The result indicated that at some phenolic acids probably were destroyed by slightly acidic pH 6. as mentioned above. total phenolic content heat treatment and converted insoluble phenolic and DPPH radical scavenging activity were highest. are also determinant factors for difference in phytochemical compounds. however. This indicated that It meant that these active compounds derived from the phenolic compounds of plants may be present the paste were easily destroyed by high acidic and in different bound forms depending on the species. Similar to the result of Tomaino et al.. Moreover. The DPPH and antioxidant activities in different amounts. the effective processing step to liberate and total phenolic content in the curry paste play an antioxidant compounds from different plant species important role for DPPH radical scavenging activity may not be similar (Kim et al. total phenolic contents and amount of phenolic acids in huyou peel extract antioxidant activity of extracts as effect of pH decreased after heat treatment. In addition. Therefore. (2007) reported that the total The flavonoid.

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