GRASAS Y ACEITES 66 (2

)
April–June 2015, e073
ISSN-L: 0017-3495
doi: http://dx.doi.org/10.3989/gya.0695141

Enzymatic interesterification on the physicochemical
properties of Moringa oleifera seed oil blended
with palm olein and virgin coconut oil

S. Dollaha, S.M. Abdulkarima, S.H. Ahmadb, A. Khoramniaa and H.M. Ghazalia,*
a
Department of Food Science, Faculty of Food Science and Technology, Universiti Putra Malaysia,
UPM 43400 Serdang, Selangor DE, Malaysia
b
Department of Crop Science, Faculty of Agriculture, Universiti Putra Malaysia, UPM 43400 Serdang, Selangor DE, Malaysia
*
Corresponding author: hasanah@upm.edu.my

Submitted: 11 June 2014; Accepted: 23 December 2014

SUMMARY: The enzymatic interesterification (IE) of palm olein (PO) and virgin coconut oil (VCO) with the
high oleic acid (86%) Moringa oleifera seed oil (MoO) could yield a good source of oleic acid fat stock that may
contain desirable nutritional and physical properties. Lipozyme RMIM resulted in different functionalities for
the MoO/PO and MoO/VCO blends due to inherent changes in triacylglycerol (TAG) compositions which, in
turn, led to different trends in DSC thermograms and solid fat contents (SFC). The enzymatic IE of MoO/VCO
increased U2S and S2U (up to 20% medium and long chain, MLCT) while it decreased U3 (triunsaturated) and
S3 (trisaturated) TAGs. The IE of the MoO/PO blends increased U2S and S3 (MMP, myristic, myristic, pal-
mitic) and decreased S2U, resulting in a lowering of melting points and SFC for MoO/VCO, while showing an
increase in them for MoO/PO. A 2.55% increase in S3 after 24 h MoO/PO 30:70 IE revealed a 6.5% harder oil at
10 °C which may imply a wider application compared to the original liquid oils. Novel MLCTs with improved
nutritional and physical properties were generated in the MoO/VCO blends after IE due to the incorporation
of oleic acid and medium chain fatty acids. MoO/PO 50:50 and 70:30 w/w after 12 h IE and MoO/VCO 30:70
are suitable for incorporation into the fat phase in ice-cream formulations while, the spreadability and plasticity
of MoO/VCO 70:30 improved at low temperatures. Both interesterified blends could be used as high oleic acid
frying oils.
KEYWORDS: Interesterification; Lipozyme RMIM; Moringa oleifera seed oil; Physicochemical properties; Structured lipids

RESUMEN: Interesterificación enzimática sobre las propiedades físico-químicas de las mezclas de aceites de semi-
llas de Moringa oleifera con oleína de palma y aceite de coco virgen. La interesterificación enzimática (IE) de
la oleína de palma (PO), aceite de coco virgen (VCO) con alto contenido en ácido oleico (86%) y aceites de
semilla de Moringa oleífera (MOO) podría ser una buena fuente de ácido oleico con propiedades nutricionales
y físicas deseables. La lipozyme RMIM produce diferentes funcionalidades para las mezclas MoO/PO y MoO/
VCO debido a los cambios inherentes en la composición de triacilgliceroles (TAG) que, a su vez, dieron lugar a
diferentes perfiles en los termogramas de DSC y en los contenidos de grasa sólida (SFC). La IE de MoO/VCO
aumentó los TAGs, U2S y S2U (hasta un 20% de cadena media y larga, MLCT), mientras que disminuyó los
TAGs triinsaturados (U3) y trisaturados (S3). La IE de mezclas MoO/PO, aumentó los TAGs U2S y S3 (MMP,
mirístico, mirístico, palmítico) y disminuyó S2U, lo que da lugar a una reducción del punto de fusión y de SFC
para el MoO/VCO mientras que estos parámetros aumentan para MoO/PO. El aumento de un 2.55% en S3 des-
pués de 24 h de IE de MoO/PO 30:70 da lugar a aceites 6,5% más duros a10 °C, que pueden tener unas aplicacio-
nes más amplias en comparación con los aceites líquidos originales. Nuevos MLCTs con mejores propiedades

1980) and a fatty acid (FA) versatility to widen their commercial applications. oxidative-resistant low are attributed to the elevated level of monounsatu. immobilized Lipozyme RMIM and can be easily grown in poor third world coun- (from Rhizomucor miehei) has been extensively tries. suppressing cer.3989/gya. MoO has greater frying stability over other con- unsaturated fatty acids (PUFA). frying oil (Bansal et  al. Abdulkarim et  al. aimed at obtaining some desirable nutritional on their characteristics.. S. because provide instant energy to athletes (Marina et al. however. Khoramnia and H. et al. 1997) compared to poly. PALABRAS CLAVE: Aceites de semillas de Moringa oleífera. 2010). This requirement can be met et al. 1... of its resemblance to olive oil (Abdulkarim et al. (2010). Abdulkarim SM. This is an open-access article distributed under the terms of the Creative Commons Attribution-Non Commercial (by-nc) Spain 3. frying oils of comparatively low price would be desir. Among commercially available little affected by drought (Tsaknis and Lalas.0695141. MCT is also unsuitable for low PUFA (0. Lípidos estructurados. PO. 2005. as MCT contain solely medium 2005. 2002) lipase preparations.. Ahmad..org/10. S. the properties of vegetable oils and therefore. and that contributes to related health disorders. 2012). April–June 2015.. mientras que la untabilidad y plasticidad de MoO/VCO 70:30 mejoró a bajas temperaturas. Among newer sources of edible oils. Some high-oleic oils ventional frying oils such as canola oil.M. Moringa ylglycerol (MCT). Ambas mezclas interesterificadas podrían ser utilizados como aceites alto oleico para fritura. 2009b).. It has been previously rated fatty acids (MUFA) and reduced saturate con. MUFA also contributes to a longer shelf 1991) due to the interactions between food and life of products due to its high resistance against oxi. ISSN-L: 0017–3495 doi: http://dx. soybean such as olive could be used for frying (Abdulkarim. doi: http://dx. has been used for years to treat oleifera seed oil (MoO) is of interest and may play a patients with malabsorption of fat problems and major role in human nutrition and health. composition resembling olive oil (Abdulkarim et al.. According to Riveros food came from the frying oil (Pérez-Camino et al. chain fatty acids (MCFA). saturated oils are needed. 2015. oil (VCO) have been selected to be interesterified or synthesized to yield novel TAGs (Xuebing et al. Therefore. is a liquid fraction of palm oil and lowering serum cholesterol levels. VCO.3989/gya. the use of more stable unsaturated oils like MoO.. reported that more than 90% of the lipids in fried tents (Gerhard et al. Copyright: © 2015 CSIC. is a tree growing rapidly even in poor soil and is Palla et al. 2010).. 2007).. A.0 Licence. Because reducing the effects of aging and coronary disease the eating habits of most Malaysian people are (Carluccio et al.doi. dation and rancidity at ambient storage and at high (2007a) and Tsaknis and Lalas (2002) reported that temperatures (Warner et al. with MoO in order to evaluate the effect of lipase 2002). palm olein (PO) and Virgin coconut acids. its high cost restricts its usage through the interesterification process of PO with on a major scale. 2007a).org/10. Ahmad SH.73%) and acids such as oleic acid.. which is the most commonly used oil for Dietary consumption of high oleic acid oils has frying foods in the Southeast Asia region (Bansal been reported to have physiological benefits such as et  al. However.. 2007). e073. MoO/PO 50:50 y 70:30 w/w después de 12 h de IE y MoO/VCO 30:70 son adecuados para su incorporación como grasa en las formulaciones de helados. Interesterificación. Structured lipids (SLs) economic and nutritional benefits to the native pop- are  defined as triacylglycerols (TAGs) that have ulation of the areas where the tree is cultivated.2 • S. Enzymatic interesterification on the physicochemical properties of Moringa oleifera seed oil blended with palm olein and virgin coconut oil. 1980). Ramachandran et al.doi. Grasas Aceites 66 (2): e073. it lacks essential fatty With a high amount of MUFA (81. MoO represents an alternative cooking purposes such as frying as it has a lower Grasas Aceites 66 (2). the Ramachandran et al. Ghazali nutricionales y físicas se generaron con las mezclas MoO/VCO tras IE debido a la incorporación de ácido oleico y ácidos grasos de cadena media. 1980). 2004).. Abdulkarim.0695141 . Moringa oleifera sively studied for this purpose (Liew et al. Ghazali HM. restructured to change the positions of FA. Lipase-catalyzed interesterification has been exten. contains a high proportion of saturated fatty acids tain types of cancer. Two been modified by the incorporation of new fatty vegetable oils.H. oil and palm olein.71%)..M. INTRODUCTION source of superior oil with high stability and good characteristics concerning the prevention of cho- Several processes are used to modify and improve lesterol and heart disease (Abdulkarim et al. Khoramnia A. 2010). The production of useful SLs from this oil used for the production of specifically structured interesterified with other vegetable oils could be of lipids (Chen et al. as a main source of medium-chain triac- able. 2001.. Lipozyme RMIM. 2005. These nutritional advantages based on deep fried foods.. Ramachandran et al. enhancing liver function... Dollah. or physicochemical properties (da Silva et al. Propiedades fisicoquímicas Citation/Cómo citar este artículo: Dollah S.

1 N NaOH to a phe- Corpration of America. California. resulting products. each oil mixture was filtered (C10:0). Germany) and Sigma Aldrich ments that show desired changes after blending and Inch.. Hence. The organic phase was then dried at Rikakikal Co. Japan). were Oil Sdn. After the reaction. Fisher Scientific. (St.2. Ltd. and left standing at room temperature (25–27 °C) tigate the physical and chemical properties of enzy. Extraction of MoO reacted oil using the method described by Long et al..9% nitrogen and stored at −20 °C until molecules to overcome these weaknesses. oleifera ker. oleifera seed to obtain the seed kernels which were then sorted oil/palm olein (MoO/PO) and M. UK) and heated at 60 °C in a convec- tion oven overnight to remove extra moisture in the 2.p 40–60 °C) in a 5 L Soxhlet extractor for 8 hours eral minutes. linoleic (18:2). Removal of free fatty acid used for the IE reaction in a solvent-free system. 2010.. Free fatty acids (FFAs) were removed from the 2. MLCT-based oil blends can be used tion method described by Bawalan and Chapman as healthy functional oils for daily consumption (2006). each dissolved sepa- for 12 h. was heated in a convection oven at 60 °C for 1 hour 2012. 1984). esterifica- tion. 1 filter paper to remove the (C16:0). Lipozyme RMIM (Rhizomucor miehei) purchased from Novozymes A/S. Interesterification reaction the Serdang area in Selangor. oleifera seed oil/ to remove any misshapen seeds.org/10. 60 °C at 200 rpm for 0. 12 and 24 h. The the oil was extracted using light petroleum ether mixture was shaken and allowed to settle for sev- (b.3989/gya.1. arachidic (C20:0). called medium-and long-chain triacylglyc- erol (MLCT). Immobilized ensure complete melting before analysis. oleifera pods were collected in 2. Matsuo et al. The reacted oil (30 g) was placed in a MoO was extracted from dried M. covered with aluminum foil 2010). while VCO was produced placed in 250 mL conical flasks.. The seeds were removed from the pods and crushed gently Sixty grams (60 g) of melted M. Malaysia. nolphthalein end-point. The aqueous phase which contained (AOAC. stearic (C18:0). palmitoleic (C16:1). palmitic through a Whatman No. Louis. The stored mixtures were thawed at room acids.doi. 2001). was separated from the organic phase using a rotary evaporator Model N-1 (Eyela..3. Bhd. for 24 hours for natural fermentation to take place.. (2003). 50:50 and 30:70 (w/w). placed in a 2 L beaker. Thus. Grasas Aceites 66 (2). One kilogram of fresh coconut milk was such as in salad dressing and for frying (Koh et al. The oil was kept in −20 °C for analysis. 2005). 250 mL conical flask and 50 mL of acetone: etha- nels that had been ground into a fine powder nol (1:1 v/v) were added and mixed. This will further use (Abdulkarim et al. Japan) and the recovered oil 60 °C overnight. for further analysis. Enzymatic interesterification on the physicochemical properties • 3 smoke point and high foaming tendency (Lee et al. MATERIALS AND METHODS oil. 1) cone and transferred to a 250 mL separating funnel. Brown. matically interesterified MoO/PO and MoO/VCO The upper layer (oil layer) was then filtered through blends and to predict the food applications of the a filter paper (Fisher QC100. long chain fatty to remove residual solvent. New Hartford. This can either be produced via a 2. PO was purchased from Lam Soon Edible rately in 100 mL of water-saturated n-hexane.4. behenic (C22:0) and lignoceric (C24:0) duplicate. April–June 2015. capric trol. The solvent was then evaporated off the FFA. The ground kernel (500 g) was placed in a diluted with 10 mL of boiling distilled water and cellulose filter paper (Whatman No. The crude oil lead to the development of a new type of structured was used without further refining. 3. Malaysia. The mixture using a Waring blender Model 32BL 80 (Dinamic was then titrated against 0. lauric (C12:0).0695141 . mature M. Bagsvaerd. Tokyo and discarded. The reaction mixtures were agitated at were either of analytical or HPLC grade and pur. Leicestershire. ISSN-L: 0017–3495 doi: http://dx. approximately 99% pure. was 2.. The titrated sample was USA). Well-formed seed virgin coconut oil (MoO/VCO) blends at ratios of kernels were dried in a convection oven at 60 °C 70:30. The blend chased from BDH Laboratories (Pool. England). All solvents and chemicals used in this study ate catalysis. oleic enzyme and the oil mixtures were kept at −20 °C (C18:1). Connecticut. The reaction mixture at 0 h acted as the con- methyl ester standards of caprylic (C8:0). the objective of this study was to inves. The reaction was carried out in noic (C20:1). Lee VCO was produced using the natural fermenta- et al. Production of VCO lipase-catalyzed reaction of acidolysis. lipids. Denmark. or interesterification (Koh et al.. 2012). Individual FA IE. eicose.. myristic (C14:0). The oil was then flushed acids (LCFA) should be incorporated into the MCT with 99. USA). ratios were selected based on preliminary experi- Merck (Darmstadt. Lipozyme RMIM from fresh coconut milk purchased from a local wet (10% w/w of oil mixture) was then added to initi- market. e073. 6. were purchased from temperature and then heated at 60 °C for 30 min to Supelco (Sigma-Aldrich Tokyo.

30. Post-IE FFA as the reference.org/10.5) as the mobile phase at a flow dard deviation of independent trials. The instrument was where no FFA was recorded in refined bleached calibrated using indium and zinc. (2010). 25. at zero (control) and 24 h reaction time. (2007) and Marina et al. ISSN-L: 0017–3495 doi: http://dx. 0. pared to the unreacted blends for both MoO/PO minum volatile DSC pans and placed in the instru. Figure 1 shows the triacylglyceride (TAG) pro- mal profiles according to Adhikari et al.85 and 70 °C and held for 2  min to erase crystal memory 2. (2009a). Prediction of solid fat content 3. Degree of oil hydrolysis following areas produced by the data integrator (Empower. USA) based on the procedure described and VCO found to be 0. while others decreased Grasas Aceites 66 (2). Massachusetts. an auto-injector MINITAB 14 (Minitab Inc.2. Ahmad. All measurements were carried column was achieved using a mixture of acetone/ out in triplicate and reported as the mean and stan- acetonitrile (63. 35.M.23% respectively by Abdulkarim et al. A statistical analysis was carried out using ration module (Waters Model 2695). 2. 40. A. e073. After 15. 10. they may accumulate in the reaction mix- (DSC) using a Perkin-Elmer Diamond DSC (Shelton. Prior to 10 °C/minute. respectively. Since not all FFAs participated in the investigated by differential scanning calorimetry IE process. v/v) into a reversed-phase high per- formance liquid chromatograph (HPLC) compris. 2.56% and 0. Darmstadt. The purge gas used deodorized (RBD) PO. USA) were used to quantify the com. and MoO/VCO in which the highest FFA levels ment’s sample chamber. Abdulkarim.24% and 0. moni- size 5 mm (Merck.3989/gya.75 2 min and heated from −60 °C to 70 °C at the rate of to 3.M. USA) equipped with a sepa.12 and 0.15 and 0. State College. Peak 3. Effect of enzymatic interesterification on triacylglyceride profile The solid fat contents (SFC) of all samples at dif- ferent temperatures were calculated from their ther. ture.37 to 0. Statistical analysis ing a Waters Alliance HPLC (Waters Corporation. The original amount of FFA in extracted MoO Connecticut. Interesterification (IE) requires the hydrolysis ponents based on relative percentages.1. rate of 1 mL·min−1. Thermal properties ols..05) with the time of reaction com- been completely melted at 60 °C) were sealed in alu. PA. The FFA levels of interesterified MoO/PO and cess starts and the end set temperature indicates the MoO/VCO blends after their removal were between complete melting temperature of the oil.18%.5:36. S.05. the FFA contents were found to be increased and a pressure of 20 psi.9% nitrogen with a flow rate of 100 mL·min−1 tion. several TAG peaks increased crystallization energy (J/g) at each temperature was in height indicating synthesis. after the reac- was 99. respectively.H. of oil by lipase in order to produce free fatty acids (FFAs) and a mixture of mono. It was then cooled to −60 °C at the rate from 0. For MoO/VCO blends. whereas the control values (pre-IE) ranged in the oil. Massachusetts.14%. The heating and cooling thermograms the analysis of other physicochemical properties. Germany) held in a tored by Tukey’s pairwise test.6.0695141 . peak and end many FFAs as possible were removed by solvent- set temperatures tabulated.5. 50 and 55 °C) and the total Lypozyme RMIM IE. Elution of TAG from the defined at p<0.4 • S. In this study. as were recorded and the values for onset. 5. The total run time was 100 min and TAG peaks were identified based on the reten. and a refractive index detector (Waters Model 2414). Milford. Milford. An empty DSC pan was used were produced after 24 h reaction time.60%.doi. 20.42%. Triacylglycerol profile then converted into percentage (%) fat based on the following equation: The triacylglyceride (TAG) profiles of the oil sam- ples were obtained by injecting 10 μL of oil samples (%) Fat=[Partial (J/G)/Total (J/G)]×[100] (10% in acetone. Ghazali 2. post-IE of 10 °C·min−1. April–June 2015.and diacylglycer- 2. USA) by subjecting all the data obtained to a uni- The TAG were separated using a commercially variate analysis of variance (ANOVA) to determine packed RP-18 column (250×4 mm) with particle the significant differences among samples. RESULTS AND DISCUSSION tion time of available TAG standards and the results of Chen et al. Dollah. as files of MoO/PO and MoO/VCO blends at the obtained above. Samples (5–8 mg that had significantly (p<0. The onset temperature solvent fractionation as they might act as an interfer- indicates the temperature at which the melting pro. interesterification Pro Version 2002.18% and 0. (2005). 3. The sample chamber was heated to levels for MoO/PO blends ranged between 1. Waters Corporation. These products of hydrolysis will then be syn- thesized to generate more of either existing or new The thermal properties of the oil samples were kinds of TAG. and significance was column oven set at 35 °C. 45. ence. and held at −60 °C isothermally for and pre-IE values of FFA content ranged from 1. Khoramnia and H. Each DSC melting thermogram was ratio of 50:50 w/w and their interesterified blends divided into different temperature sectors (0.7.8. S.23 to 0.

(2012) reported that an increase U2S and S2U TAGs. Triacylglyceride profiles of non-interesterified MoO/PO (a). oleic and as such. The rate of U3 hydrolysis was much lower interesterified PO and rice bran oil blends compared (0–1. PPL.0695141 .. The highest amount of TAG hydrolysis to 20. ISSN-L: 0017–3495 doi: http://dx. values of 1. MMP. the same retention time under the conditions used Unexpectedly. As a result.13% in 70:30. Enzymatic interesterification on the physicochemical properties • 5 FIGURE 1. The levels of U2S were found to (Figure 1a).. 25. a gradual increase in U2S The same trend with MoO/VCO blends follow- and a decrease in S2U were observed in all blend ing Lipozyme RMIM IE occurred in the case of ratios. 2012) which was with the values of 2. blends that showed the highest increase s in U2S As complete identification of TAG in MoO/PO after being interesterified by Lipozyme RMIM for is limited by the unavailability of standards. S3 enhancement resulted in inter- in the analysis. respectively.doi. MoO/VCO (c) blends and 24 h. MoO/VCO (d) blends.88% and 22. 50:50 w/w. 3. La: lauric acid. S2U. Abbreviations: M: myristic acid. the level of S2U and increase in the level of U2S are POO+POL. desired (da Silva et al. interesterified PO which was catalyszd using micro- dence of changes in the TAG composition based on bial lipases from different sources. an increase in TAG containing unsatu- linoleic acids respectively) were tracked. (2011) also reported (OOO) was completely different from the MoO/PO on the increase of U2S and the decrease in S2U in results. The decrease in relative changes in the concentrations of MMP. 1.57%. S3 TAGs were increased in (OOO decreased 6. the trend for changes in U3 S2U groups. which is a medium-medium- be 30.48% with enhancement long chain (MML) TAG. palmitic. would be a beneficial PPO and PPL levels (S2U) decreased considerably and nutritional fat (Lee et al. 2009) P. O: oleic acid.23% decrease (from 21. all interesterified MoO/PO binary blends with the trol (pre-IE).32%) however. is generally called MLCT values of 4. e073.org/10.73%) where OOO showed the great- of U3 TAGs (OOO) remained unchanged except est decrease in concentration over the time of IE in 50:50 w/w with a 1. Debnath et al.34% for 30:70. respectively) of MoO/PO and MoO/VCO Ghazali et al.59% in 50:50 w/w generated due to the rearrangements of the TAG respectively and less saturated TAGs (U2S) were occurring after IE . The MoO/PO the degree of unsaturation. P: palmitic acid. increased. the level IE (3. as MMP (myristic myristic palmitic) would (U2S) due to the incorporation of oleic acid from be the representative of this type of TAG group MoO fatty acids.23%) in MoO/PO IE compared to MoO/VCO to the unreacted PO. only 24 h were 30:70 and 50:50 ratios. POO and rated fatty acids may contribute positively to the POL were quantified together due to both having stability to the oil as well as to its health benefits. U2S and U3. which is also desirable in this PO blends showed major increases in POO+SOL study. L: linoleic acid. As shown in Table 1. By comparing with the con. A similar observation was reported by fatty acids. as a structured lipid (SL). ↑ arrows depict increases while ↓ arrows depict decreases in TAG concentrations. The interesterified (24 h) MoO/ esterified MoO/PO.83% in 50:50 and 2. indicating hydrolysis. O and L indicate myristic. Palla et al. S2U with palmitic-stearic acid mixtures using Lipozyme decreased gradually in all ratios of the MoO/VCO RMIM as a result of a reaction between U3 and blends. April–June 2015. OOO and PPO (where M.3989/gya. MPL. However. (1995a) where an increase of S3 in all interesterified blends shown in Table 1 provide evi. Ribeiro et al. the level of U2S increased while. 50:50 (medium long chain TAG) and when considered and 70:30 w/w.15–6. S: stearic acid.55% where S and U represent saturated and unsaturated in 30:70.66% and 4. As shown in Table 1. C: capric acid.51%.58% and 1. 2010. On the other hand. Lipozyme RMIM interesterified MoO/PO (b).55% (Table  1). TAG groups (S3. as IE occurred in U2S after sunflower oil was reacted progressed..73%) occurred after 24 h IE of Grasas Aceites 66 (2).

and body fat accumulation in the body (Lee et al.96±0.23 27.03 9.64 2. In fact. MLCT not only can provide us with nutritional properties from the essential fatty acids incorporated.27 4. uses the enzymatic IE pro- cess for its production involving coconut or palm kernel oil and an edible vegetable oil (rapeseed. 2009) MoO/PO (30:70 w/w) Time of reaction (h) MoO/PO (30:70 w/w) Time of reaction (h) 3.18 64. the function of Lipozyme 2.07 35.38±0.52±0.61±0.48±0. Khoramnia and H.54±0. Ahmad.00 available MLCT sold in the market by Nisshin 3 3 Ollio Ltd. Dollah. April–June 2015.60±0.13 18.24±0.27±0.24±020 2).84±0.24 37.32±0. (2005) reported on interesterified palm stearin with coconut oil.98±0.11 belong to S3 TAGs consisting of CCLa.52±0.. As mentioned by O’Brien (2003).09 25. 2012).33 26. where LaLaLa 4.13 importantly it can also help to reduce body weight 6 6 TABLE 1.82±0.13 40. As shown in Table 2.23 7.24 8. 2001).23 8. Abbreviations: S3: tri-saturated.75±0.30 total amount of generated MLCT with incorpo- 24 24 rated oleic acid (LaLaO.. It has been well Means for the determined values in the same row followed by the same superscript letter are not significantly different (p>0.30±0. the major 2. Group. Lipozyme RMIM catalyzes the 2.55±0.28±0.37 15. 0 0 Khatoon et  al.47 17.12±0.00±0.71±0.23 24 (no  change in OOO value) was detected for the 24 24 h interesterified MoO/PO 70:30 w/w.41±0. the incorporation of medium chain saturated FAs occurred in safflower oil (Utsugi et al.73±0.74 3.28 15.14 and anhydrous milk fat (Liew et al.H.67±0.92±0.25±0.26±0.38±0.03 46.83±0.M. A.03±0.12±0. Ltd. 1998).org/10.74±0.15 19.45 5.75±0.03 29.04 cleavage of FAs from the glycerol backbone of 3 3 some TAG species at the 1.10 44.6 • S. while the lowest amount 3. From 12 12 the health benefit point of view.19±0.96±0.43% in 24 h interesterified MoO/VCO 70:30 w/w (Table 2.26 15.07 16.38±0. 3 position (those that decreased in concentration after the reaction) and 2.10±0.01 23.28 4.16 7.18 42.69±0.17±0.21 32.14 43. Ghazali MoO/VCO 70:30 w/w.M.86%.21 11.16 18.43±0.21 13.16 24. IE resulted in the increase and 6 6 synthesis of new TAGs.13 17. 2.22±0.18 33.27 12.37±0.07 11. in the case of MoO/VCO IE.23 42.06 67.19±0. and LaPM.10 48.23±0.32±0.27 35.3989/gya.16 21.29±0. the PO Grasas Aceites 66 (2).71±0.65±0. U2S: di-unsaturated-mono-saturated.48±0.77±0.03 23.05±0. S2U: di-saturated-mono-unsaturated. S.04 decreased tremendously while that of LaLaO and LaOO experienced major increases.55±0.18 15.55±0.39±0.13 12.04±0.  CLaLa.46±0.16±0.06 28.40±0..43±0.00 29.27±0. LaMO.51 7.10 RMIM on MoO/VCO IE resulted in the increase in MLCT species (LaLaO.06 7.14 In this study. The first commercially 2.13 cottonseed and soybean oil) (Lee et al.76±0.00±0.23±0.73±0.95±0. other TAGs that showed corre- MoO/PO (70:30 w/w) Time of reaction (h) MoO/PO (70:30 w/w) Time of reaction (h) sponding decreases proportional to the reaction time 3.13 16. e073.06 21.76±0.24 39.62±0. but most 65.16 12.05±0. which was revealed by the emergence of several lower molecular weight TAGs.18 39.19±0.09±0. the TAG group comprising LaLaO and LaMO in all MoO/VCO ratios (Table 2)..16 23.50±0.79±0.65±0.04 47.79±0.90±0.01 27. During IE.00 48.34±0.40±0. LaMO. established that substrate ratio is an important 12 12 parameter to obtain the desirable yield in IE (Fomuso et al. LaPM and 6 6 Triacylglycerol composition (g·100 g−1) of Moringa oleifera seed oil interesterified with palm olein (PO) and virgin coconut oil (VCO) LaPO) concentration as well as the synthesis of a new TAG species (LaOO).41±0.06 18.13±0.46±0.55±0.57 10.38 7.05±0.67 5.55±0.20 29.19±0.59±0.21 28.41 2. The difference in lipozyme RMIM function- ality toward PO and VCO interesterified blends TAG% TAG% with MoO could be due to the processing methods S2U U2S S2U U 2S U3 U3 S3 S3 undergone.05).77±0.33 7.11 17.07 50:50 with the value of 17.05±0.11 12.93±0.77±0.79±0.72±0. Abdulkarim.16 13. The 4. LaLaM.34 2.26±0.21 8.18 14.85 27.0695141 . 2012).28 15.11 re-esterifies randomly at the free hydroxyl positions on the glycerol backbone of the existing acylglyc- 0 0 erols.63±0.47 3.17 10.03±0.44±0.13 26.34±0.11 1.07 48.19±0. The most noteworthy increase in TAG concen- 0 0 tration was observed for MML (medium-medium- long chain).54 1.34 20. 12 12 LaLaLa.16 27.09 65.31 34. LaPO and LaOO) was maximized in 24 h interesterified MoO/VCO MoO/PO (50:50 w/w) Time of reaction (h) MoO/PO (50:50 w/w) Time of reaction (h) 3. In other stud- 24 24 ies.28 21. ISSN-L: 0017–3495 doi: http://dx.23 70.96±0.51 18.07 20.2±0.11 19.38±0.48±0.27 8. S.36±0.35±0.17 7.53±0.12±0.09 21.56±0. 3.. namely MLCT.99±0.07 3.20 20.18 46.33 26.17 21.39±0.13 12. U3: tri-unsaturated.81±0.doi.06±0.23 13.73±0.33±0.80±0.57 MLCT group generated following IE was MLL 3 3 (medium-long-long) comprising LaOO in all MoO/VCO ratios with a maximum value of 5.85±0.29±0.29 41.13 25.40±0.24 8.02±0.96±0.41±0.03 19.

48±0.49±0.51±0.01d a a c b LaPO MLL 0.03 1.10e a a b b LaPM MLM 3.org/10.06c a b c d LaOO MLL 0.98±0.49±0. Effect of enzymatic interesterification on DSC and Ebrahimpour et al.06b LaOO MLL 0.17±0.01±0.55±0.01a 1.50±0.23±0. the con.11b a b c d LaOO MLL 0.13 3. Enzymatic interesterification on the physicochemical properties • 7 TABLE 2. as a result of the S3 increase in inter- TAGs are responsible for the structure of the fat esterified MoO/PO.3.39±0.05±0.17±0.14c Means for the determined values in the same row followed by the same superscript letter are not significantly different (p>0.25±0.77±0. Generally.06 1.33±0.21±0. As indicated by khoramnia et al.39±0.06 0.0695141 .25±0. (2007a).00 1.11e a b c d LaMO MML 0.13a 2. 2012).94±0. P: palmitic acid. S: stearic acid.46±0.43±0. ality and improved sensorial properties while S3 However.12±0.96±0.04b 2.58±0.04e a b b c LaPO MLL 0.40±0.06 1.86±0.10 3.92±0. 50:50  w/w and 70:30 w/w.97±0.24±0.25a 3. which was Grasas Aceites 66 (2). ISSN-L: 0017–3495 doi: http://dx.08b 2.40±0. the melt- esterification lead to greater potential for applying ing profile of both IE blends is supposed to shift these interesterified blends in foods.20 3. the corresponding melting (Rodrigues and Gioielli.04d LaPM MLM 1.07e a b b c LaPM MLM 2.07e LaMO MML 0.13 1.13c 2.10b 3..01 3.93±0.13d a b c d LaMO MML 1.08d 7.06b 3. 2007) in order to maintain the bioactive compounds.34±0. generation of TAGs with lower melting points.33±0. (2011) 3. C: capric acid. by increasing the proportion of MoO. However. April–June 2015.06 0.92±0. lization thermograms of the interesterified MoO/ the increased U2S content in the MoO/PO and PO and MoO/VCO blends. cates a reduction in TAGs as represented by peak 2 tance. In addition.03a 1.13 4. known as a functional high médium chain fatty acids and foam formation oil or mineral oil was produced in mild conditions (Lee et al. MoO/VCO blends produced by enzymatic inter.08 4.41±0. It could be also indicated that interesterified and a possible formation of more TAGs.13b 4.00 1.69±0. a new peak (peak 3) was generated in et al.22±0. the mineral contents thermograms of the cultures play an essential role in the function of lipases. MoO revealed great resistance dur.11 4. O: oleic acid.68±0. the ing the frying procedure due to its high oleic acid enthalpy of the major peak 1 in MoO/PO 30:70 and content.88±0.00±0.doi.03 2. As demonstrated by Abdulkarim ing MoO.25±0. as indicated by Ribeiro et al.90±0.07d 2.11c 6.28 4. As IE progressed.05). Abbreviations: M: myristic acid. profile shifted towards higher temperature regions tribution of oleic acid from MoO into the interester.00±0.77±0.08±0.04 0. MLCT generation and oleic acid contribution as cially during the deodorization process between 204 the original VCO is not suitable for frying due to the and 245 °C.49±0. respectively.99±0.74±0.46±0.06 2.04 2.67±0. produced after the refining.07 1.70±0.13±0. MoO/VCO fryng quality improved due to the izing (RBD) procedure with heating is applied espe. bleaching and deodor.11 4.03a 1.31±0. This indi- due to a lower degree of saturation and higher resis.29±0.14a 2.14±0. La: lauric acid.07c 5.10c 3.29±0. Figures 2 and 3 show the melting and crystal- Generally.53±0. Therefore.3989/gya. (Table 1).07a 0.01 2.07 0.01 5.11b 1.06c 3.70±0.28 0.33±0.15±0.57e a a b c LaPO MLL 0.13 1. e073.12±0. Relative percentage of medium and long chain triacylglycerol (MLCT) in the control and interesterified MoO/VCO blends Type of Time of reaction (h) TAG MLCT 0 3 6 12 24 30:70 LaLaO MML 2.13 4.32±0.87±0.63±0.10 2. VCO.47 1.13b 5. while peak 2 decreased frying quality of PO enhanced after IE with MoO followed by an overlapping with peak 1.87±0. by increas- used as frying oils.03 3. S2U TAGs are towards lower temperature regions indicating a associated with enhanced technological function.10 2.08d 3.15±0. (2009). (Chen et al.58±0.11 2.04d 5.65±0.78±0.11 2.63±0. L: linoleic acid. 2003).13 1. (2011).64±0.03c 5.07 1.83±0.01c 70:30 LaLaO MML 0.. ified blends made them a potential candidate to be In MoO/PO interesterified blends.15±0.26±0. it could be proposed that the 50:50 w/w blends increased.08d 50:50 LaLaO MML 1.

the melting tempera- peak 2 gradually disappeared when the propor. S. which crystallized at −49.97 °C. da Silva et al. The above results show that the IE of different ing points from −14 °C to 1 °C. Melting and crystallization profile of Lipozyme RMIM interesterified MoO/PO blends. and those representing findings indicated that the blends were composed Peak 2.M. Dollah.0695141 . April–June 2015. PO. and triolein has a blends of MoO/PO would produce TAG species melting point of −4 °C (Hynes. This perature (6. Melting profiles for (a) 30:70 w/w (b) 50:50 w/w (c) 70:30 w/w blending ratios and crystallization profiles for (d) 30:70 w/w (e) 50:50 w/w (f) 70:30 w/w blending ratios. in the MoO/PO increased and as IE progressed it shifted to a lower 70:30 blend. peratures before IE. The resulting blends were found to have MoO/PO blends (Figure 2). the TAGs in Peak 1 crystallized at a higher tem- resenting peak 3 were contributed by MoO. Abdulkarim et al. three crystallization higher end set temperatures than the melting tem- peaks (peaks 1.M. for the blends containing 30% MoO which melted Concurrently.97 °C. However. 2010). (2007b) reported Grasas Aceites 66 (2). From the cooling thermograms of TAG.3989/gya. peak 1 gradually disappeared and the temperature region. and the TAGs rep.org/10. This is as expected as the blend contained a MoO/PO 70:30 blends. These which crystallized at 3. whereas there was little change result is expected as the main FA of the blends is in the peak temperature for the TAGs represented oleic acid and OOO is the main TAG. Ghazali FIGURE 2. ISSN-L: 0017–3495 doi: http://dx. IE.69 °C). S. Ahmad. represented by peak 1. Abdulkarim.36 °C. After 24 h mainly of low melting TAGs. two obvious crystallization higher quantity of MoO which. e073. tures were still lower than the original MoO. when compared to peaks were observed: TAGs representing Peak 1.doi. Khoramnia and H. (2010) reported that triunsaturated TAGs have melt. has a higher degree of unsaturated FA. except tion of MoO was increased over the time of IE.8 • S. However. it was observed that the size of peak 3 at 22. A. 2 and 3) were observed. with wide ranging crystallization and melting tem- In the crystallization thermograms of unreacted peratures. by Peak 2. indicating the synthesis of lower TAG represented by peak 2 became the dominant melting TAGs. However.H.

the low temperature region. This was reflected in the crystal.3989/gya. indicating that the synthesis of temperature range. tion.org/10. Enzymatic interesterification on the physicochemical properties • 9 FIGURE 3. This indicated that the rearrangement of low melting points that melted earlier and this peak FAs responsible for these peaks leading to the for- then became broader and finally overlapped with the mation of lower melting TAGs after IE were most major TAG peak (peak 1) after 6–24 h of IE. a low melt. (peak 2) at −0. e073. After the IE of MoO/VCO 70:30 blend.9 °C after 6 h IE high melting points of TAGs which melt in a wide using Lipozyme IM.1 °C to 19. acid incorporation and a higher degree of unsatura- lization temperature increase from 1. April–June 2015.87 °C.9 °C. Melting profiles for (a) 30:70 w/w (b) 50:50 w/w (c) 70:30 w/w blending ratios and crystallization profiles for (d) 30:70 w/w (e) 50:50 w/w (f) 70:30 w/w blending ratios. resulting in a reduc- In the melting profile of the 30:70 blend.doi. The melting thermogram of the interesterified Long et al. the increase in melting temperature from 18. Melting and crystallization profiles of Lipozyme RMIM interesterified MoO/VCO blends. (Figure 3) provide several important observations the minor and major melting peaks shifted towards concerning the melting and crystallization profiles.6 °C to 12. medium and also increased from 14.5 °C after 24 h self-IE of MoO using ing the reduction of high melting TAGs due to oleic Lipozyme IM 60.9 °C in peak 1 shifting to a lower melting region indicat- (control) to 20. resulting likely to be influenced by unsaturated FA (oleic acid Grasas Aceites 66 (2). tion in the melting temperature of the interesteri- ing Peak 2 represented unstable TAG crystals of fied blend. (2003) reported that the slip melting MoO/VCO 70:30 blend (Figure 3) displayed a well- point of palm olein/flaxseed oil blends (90:10 w/w) defined peak which is related to the low.32 °C and a minor peak (peak 3) at The results for the IE of the MoO/VCO blends −12.0695141 . ISSN-L: 0017–3495 doi: http://dx.47 °C with shoulder peaks rearrangement of the FA moiety. The major melting peak (peak 1) higher melting point TAGs took place during the of 0 h blend occurred at 7.

1% and 10. the temperature at which SFC is zero increased may improve the quality of pastries as Ariffin et al. Soares FA rich in VCO. mogram. 2010). During the IE of MoO/VCO 30:70. S. According to Rodrigues of the interesterified blends.org/10.4. it (2010) reported that cookies made from medium- still remained below ambient temperature (25–27 °C) and long-chain triacylglycerol-enriched margarines or body temperature (35–37 °C). The SFC of the blends at 0 °C is peratures (10 °C) with SFC values of 23. A. respectively. April–June 2015. rangements after the IE of MoO/PO.M. For blends with lower In interesterified MoO/VCO blends the level of proportions of MoO. Wassell 3. Ghazali incorporation) from MoO. the have good texture and sensory perception as well as SFC% of all MoO/PO ratios increased where 30:70 excellent nutritional benefits.8%.1 to 11. tration of high melting TAGs. ISSN-L: 0017–3495 doi: http://dx. the thermal properties of the S3 decreased following the increase in theU2S level interesterified oil revealed an influence of saturated resulting in the production of softer fat. the level of S3 With regards to thermal properties. physical and chemical properties of PO and VCO. (2007b) demonstrated elevated 30:70 are suitable for incorporation into the fat SFC after IE indicating the ability of the enzyme to phase in ice-cream formulations as demonstrated form higher-melting TAGs. Wassell and Young. w/w blend revealed more obvious changes compared to other ratios. ing their spreadability and plasticity at refrigerated depending on the type of TAG formed (Debnath temperatures. The product’s stabil- amount of MoO in the blends.6% and 0% in unreacted (0 h) MoO/PO 30:70 w/w blend which This study has shown that enzymatic interesteri- increased to 11. 1998. CONCLUSIONS at 10 °C and 15 °C with SFC values of 4.9% SFC at 20 and rated TAGs which then contributed to an increase in 22 °C. Dollah. Healthier frying blends and ice-cream et al. e073. The major difference was observed 4.doi. After 24 h IE. 30:70 w/w with 20.1% and 6% after 24 h IE. in the MoO/VCO crystallization ther. by Liew et al. respectively and the interesterified blend after melting temperature in the MoO/PO blends which is 6 h with 11.. Effect of enzymatic interesterification on solid and Young (2007) and Lida and Ali (1998) demon- fat content strated that for spreadability at refrigeration temper- atures. thus increasing the Consequently. the MoO/VCO The findings show that for each MoO/PO blend interesterified blends with elevated levels of MLCT ratio.3% SFC fall within this group of fats.5% and 6% more SFC% in 10 melting range that have clearly affected the SFC and 15 °C. the lower for 70:30 due to the difference in the oleic major crystallization peak decreased and the minor acid incorporation associated with the MoO level. interesterified at various times and ratios. Abdulkarim. ing and shifting of Peaks were clearly seen. nally do not offer satisfactory characteristics with SFC values of 89.55% in the 30:70 blend. IE caused the formation of more satu. et al. fat bases were produced from MoO interesterified Grasas Aceites 66 (2). respectively. Khoramnia and H.0695141 . the SFC should not exceed 32% at 10 °C in The solid fat content (SFC) profile as a function order to meet the minimum plasticity requirement.55% of S3 enhance. indi- It could be concluded that 2. the higher the SFC 20 and 22 °C (Lida et al. Long et al.3989/gya. (2009). the major crystallization peak (peak 1) was the interesterified MoO/VCO 50:50 blend showed observed with a minor peak (peak B) for the 30:70 0% SFC while it was higher for the 30:70 blend and blend ratio. cating the formation of TAG species with a wider ment brings about 6. (2001). melted at lower temperatures which allowed them to Changes in the amount of TAG species after IE remain liquid at ambient temperature while improv- are normally accompanied by a change in the SFC. peak increased. In addition.. the greater the quantity of terized in fats with a minimum of 10% SFC between either PO or VCO in the blends. fication with MoO an effective way to modify the As stated in the TAG section. In this agreement. in accordance with the results obtained in previous Blends with zero SFC at 25 °C including MoO/PO sections. (2012) also reported SFC reduction in a coco- Generally. However. the broaden- (MML) increased by up to 2.. is at 0 °C. Interesterification of and Gioielli (2003). All interesterified MoO/VCO blends liquid oils due to the function of Lipozyme RMIM. The unreacted binary blend of MoO/VCO MoO/VCO. of temperature for the MoO/PO and MoO/VCO The binary blends of 70:30 w/w MoO/VCO can be blends. is regarded as offering good spreadability at low tem- shown in Table 3. Ribeiro et al. 2011. the lower the SFC ity and its resistance to oiling-out could be charac- is at 0 °C. compared to the control (0 h). after IE. respectively. (2003) and 50:50 and 70:30 w/w after 12 h IE and MoO/VCO Abdulkarim et al. VCO origi- mixture has been produced.10 • S. At 20 °C.2% related to the degree of saturation: the higher the after 0 to 24 h IE. The obtained result indicates that unlike 2007). Likewise. Ahmad.M. Koh et al. where SFC gives crystallization thermograms indicate that a softer an indication of the fat’s spreadability. Both results from the melting and At low temperatures (4–10 °C). S3 TAGs are responsible for the MoO/PO blends caused an increase in the concen- structure of fatty foods.H. due to the TAG rear. S. interesterified MoO/PO revealed product’s melting temperature and SFC% at higher a harder structured fat blend produced from two temperatures. nut oil-canola oil interesterified blend.

7 0.9 89.0 – – – – 0 100.3 24.0 48.1 5.9 0.1 21.4 0.1 16.8 49.8 4.4 13.8 84.0 15.2 14.1 1. Solid fat content of unblended and interesterified Moringa oleifera seed oil with palm oil and virgin coconut oil (MoO/PO and MoO/VCO blends) Grasas Aceites 66 (2).6 91.6 76.5 0.6 11. TABLE 3.5 21.8 4.0 10.0 – 6 99.4 4.8 0.6 8.0 0.6 43.1 68.8 0.9 51.3 18.3 24.2 0.3 17.0 49.7 39.1 38.7 0.6 0.5 30.7 44.3 34.7 92.6 75.7 0.1 3.2 12.9 0.6 12.9 46.8 8.3 0.9 34.1 10.5 14.7 11.0 28.0 – 24 91.2 0.0 – – – 0 90.6 1.0 3.1 30.3 5.1 0.1 2.3 57.4 10.0 – – – 24 45.9 46.5 20.9 4.9 8.0 3.5 4.8 13.0 – 12 55.0 – – 24 60.6 23.7 20.8 0.9 66.3 34.0 48.6 69.1 0.4 0.9 91.8 0.4 51.3 73.5 37.8 19.1 0.3 0.9 0.5 23.7 32.0 – – PO 60.0 – – – 12 45.7 20.2 6.6 0.5 8.3 12.9 88.3 5.7 3.2 72.2 34.0 1.1 0.9 31.0 – – 12 62.4 4.0 – – – – – 24 32.6 0.0 – – – 70:30 70:30 0 39.7 2.2 0.4 0.6 75.5 19.8 8.8 10.2 13.6 61.4 11.8 44.5 0.7 11.7 25.0 24 98.0 – 24 52.1 13.4 28.8 15.5 39.0 – – – – – 6 34.9 24.0 – – – 0 72.9 23.9 14.0 40.7 0.0 – – – VCO 94.1 8.8 3. ISSN-L: 0017–3495 doi: http://dx.4 19.8 14.0 30:70 30:70 0 53.2 64.9 0.7 0.0 35.6 0.0 0.7 34.9 0.6 0.0 2.3 0.0 – – 12 90.1 13. April–June 2015.0 – – – 6 91.0 40.1 40.4 2.4 0.0 – Enzymatic interesterification on the physicochemical properties • 11 50:50 50:50 0 47.2 0.4 6.5 0.0 – 3 99.5 43.5 7.0 – – – 3 34.3 0.doi.5 7.7 9.0 44.1 6.0695141 Solid fat content (%) Solid fat content (%) MoO/PO Temperature (°C) MoO/VCO Temperature (°C) blends (w/w) 0 2 5 7 10 15 20 25 30 35 blends (w/w) 0 5 10 12 15 17 20 22 25 30 MoO 34.0 – – – 6 45.5 91.0 – – – – – .1 71.6 25.0 96.0 – 12 99.6 0.0 0.2 2.6 0.1 0.1 76.0 – – – – – 12 33.0 – 6 53.8 32.6 0.1 30.1 11.4 0.5 0.0 2.6 36.4 48.3 54.5 12.5 50.2 0.7 16.0 38.5 0.8 9.7 33.4 0.7 0.3989/gya.1 0.9 2.7 35.4 0.9 74.2 0.1 77.8 1.2 0.2 6.3 61.5 25.7 11.7 3.5 0.7 28.4 0.0 24.0 – – – 3 64. e073.7 0.0 – – – 6 63.5 8.5 50.0 – – – 3 45.0 – – MoO 34.0 – – – 3 90.0 2.1 1.2 11.6 21.1 7.7 0.8 0.3 74.8 27.7 6.0 – 3 53.5 20.org/10.

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