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Synthesis and characterization of antioxidant-enriched Moringa oil-based edible oleogel

  • Nazia Yaqoob , Saima Rehman , Nusrat Shafiq EMAIL logo , Muhammad Mohsin , Aleena Akbar , Samir Ibenmoussa , Gezahign Fentahun Wondmie EMAIL logo , Yousef A. Bin Jardan and Mohammed Bourhia
Published/Copyright: July 1, 2024
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Open Chemistry
From the journal Open Chemistry Volume 22 Issue 1

Abstract

This study aims to formulate and optimize Moringa oleifera (Moringa) oil oleogels using pectin (PC) and chitosan (CS) as gelling agents. These include monogelator oleogels, utilizing either PC or CS as a single gelling agent, and binary gelator oleogels, incorporating a combination of both PC and CS. Among the binary gelator oleogel compositions, the most stable oleogel OPCCS2 was further studied with the addition of antioxidants. The important antioxidant compounds of gallic acid equivalents (GAEs)/Moringa antioxidant extracts (MAEs) were quantified by the use of various assays. The oil-binding capacity (OBC) of the most stable oleogel MCPC1.5% was 99.94 ± 0.05. The lower peroxide value of antioxidant-rich oleogels at 1.5% concentration of GAEs (4.34 ± 0.025) and MAEs (4.32 ± 0.03) suggested its richness of phenols to retard the lipid peroxidation of oil. The opaque appearances of the formulations were studied via polarizing light microscopy. The molecular interaction study through FTIR analysis revealed the hydrogen bond interactions between the carboxyl groups of fatty acids and hydroxyl groups of polysaccharide chains. The differential scanning calorimeter analysis further confirmed the presence of strong interactions between polysaccharide chains and the oil phase. These findings indicate that the optimized oleogel formulations have the potential for imminent advances by exhibiting improved texture, biocompatibility, enhanced OBC, and stability.

Graphical abstract

Keywords: antioxidants; emulsion; grapefruit peel; Moringa seed oil; oleogel; solid fats

Nomenclature

OPC27

Moringa oil–pectin oleogel

OCS30

Moringa oil–chitosan oleogel

OPCCS2

Moringa oil–chitosan–pectin oleogel

MCPC1.5%

Moringa oil–chitosan–pectin oleogel with 1.5% Moringa antioxidant extract addition

GCPC1.5%

Moringa oil–chitosan–pectin oleogel with 1.5% grapefruit antioxidant extract addition

GAE

Grapefruit peel antioxidant extract

MAE

Moringa seed antioxidant extract

1 Introduction

Solid fats are indispensable ingredients widely used in bakery products and significantly influence food qualities such as aroma, flavor, texture, and shelf life [1]. However, these solid fats contain saturated and trans fats; their excessive intake has been discouraged due to the development of cardiovascular diseases [2]. The prevention of cardiovascular diseases prostrates in eliminating trans fats from processed food. In this regard, the oleogelation approach presents a promising alternative oil structuring technique to deliver healthy lipid phases in the macroscopic semi-solid network [3].

Oleogelation has been a hot topic in recent research to stabilize healthy solid fats. Conventionally, oleogelation is accomplished by the gelation of liquid oil with different hydrophobic structuring agents such as glycerol, resins, and waxes [1]. It has been established as an efficient physical technique by using food-grade hydrophilic polymers to convert the liquid oil phase into a solid-like gel without influencing the chemical properties of the oil. Polymers such as polysaccharides, cellulose, and its derivatives have been applied to prepare healthy solid fats using healthy and balanced fatty acid profiles of vegetable oils [4,5]. However, there is limited literature on developing emulsion template oleogels using citrus pectin (PC) and chitosan (CS). Based on this, it would be interesting to produce ideal oleogels with CS and PC polymers using emulsion templates. The use of unique antioxidant extracts of grapefruit peels (gallic acid equivalents [GAEs]) and M. oleifera (Moringa antioxidant extracts [MAEs]) seed residues, which otherwise remain unutilized, in formulating antioxidant-enriched oleogels has not been encountered yet.

CS is a biodegradable, eco-friendly, and amphiphilic polymer that readily dissolves in acidic media due to amino group protonation at the C position [6]. PC is a plant-based heteropolysaccharide, bio-economic hydrocolloid, and a commercial organic surfactant commonly used to make stable jams and jellies without affecting the flavor of the base material. It is present in citrus fruit peels such as lemons and oranges [7]. It possesses an excellent emulsifying and gel-forming capacity and acts as a surface-active agent [8]. Previous research studies [8,9,10] demonstrated its gelation ability in the water phase and stabilization of the oil–water interface, thus highlighting its potential use in oleogelation.

Stabilizers are components that are added during the formation of oleogel to guarantee homogeneous mixing of the polymer and oil. In this work, xanthan gum (XG) and tween-80 were employed to stabilize the PC and CS emulsions. Coupling the stabilizing agent with amphiphilic polysaccharide is convenient for stabilizing oil in water emulsion to develop oleogel. XG, a heteropolysaccharide, is produced by fermentation microorganisms Xanthomonas campestris. It exists in branched form with a cellulose backbone and exhibits a negative charge due to the presence of a carboxylic group in its structure. It can link various positively charged molecules [11].

Moringa seed oil, a healthy edible oil, is a rich source of various antioxidants such as tocopherols, β-sitosterols, catechin, moringine, quercetin, zeatin, and ferulic acid. Its fatty acid profile is identical to olive oil [12]. The healthy monounsaturated fatty acids to saturated fatty acid MUFA/SFA fatty acid profile, along with a lower amount of polyunsaturated fatty acids (PUFA) of this characteristic oil, is associated with lowering the risk of cardiovascular diseases and sterol fractions, and are known to involve in the cholesterol metabolism [13,14]. The oil derived from the seeds of M. oleifera can serve as a good liquid phase for emulsion template oleogel formulation. However, the presence of unsaturated fatty acids in large amounts in oils causes rapid oxidation [15].

Synthetic antioxidants have been encouraged to impart long-term stability to foods. Commercially available artificial antioxidants include butylated hydroxyanisole, butylated hydroxytoluene, and tertiary butylhydroquinone [16]. However, health concerns have been raised over time due to the high uptake of synthetic antioxidants [17]. In recent years, interest has been focused on natural antioxidants to provide stability and increase consumer propensity. Dietary polyphenols are natural antioxidants present in plants and protect against damage caused by free radicals [18].

The citrus peels contain larger amounts of flavonoids than those of the other components of the fruit. Citrus flavonoids are reported to possess valuable biological activities such as antiviral, anti-inflammatory, and anticancer activities, helping reduce the fragility of blood capillaries [11]. Epidemiological studies prove that the fiber derived from grapefruit peels lowers the risk of gastrointestinal disorders and promotes physiological functions by reducing total serum cholesterol [19]. The phytoconstituents present in seeds of M. oleifera exhibit anti-ulcer, anti-inflammatory, and antimicrobial properties [20]. These have good antioxidant properties due to flavonoids like catechin, quercetin, and phenolic acids such as cinnamic and ferulic acids [21]. However, the high amount of active phenolic hydroxyl present in polyphenols of plants with high antioxidant activities can reduce their solubility in oil. For a practical purpose, these polyphenols are employed in biopolymers where these polyphenols interact with polysaccharides to develop colloidal complexes [22]. It contributes a feasible approach to include polyphenolic extracts into emulsion template oleogels.

In this research, the emulsion-based oleogels were prepared and divided into three portions: mono-gelator oleogels and binary-gelator oleogels without the addition of antioxidants, binary-gelator oleogels containing antioxidant extracts. According to the emulsion template method, Moringa oil was chosen as the oil phase, CS and PC as oil structuring agents, and XG and tween-80 as emulsion stabilizers to prepare the edible Moringa oil-based oleogels. Then, the antioxidant extracts of grapefruit peels (GAEs) and M. oleifera seeds (MAEs) were applied further to increase the stability of oil in the oleogels. The water phase of resultant emulsions was removed through a drying oven and freeze dryer to observe the most effective drying method. The dried products were further sheared to obtain the final Moringa oil oleogels. The optimization of oleogels was done at minimal concentrations of gelling agents to increase the oil-binding capacity (OBC) and obtain the desired gel strength. The final oleogels were evaluated by microstructure, OBC, oxidative stability, molecular interactions, and thermal behavior.

2 Materials and methods

2.1 Collection of materials

The M. oleifera seeds were purchased from local seed markets of Tehsil Gojra and Faisalabad (Pakistan). The seed's wings and coats were removed from the mature seed pods. Good-quality dried seeds were selected and powdered to uniform particle size using an electric grinder.

The grape fruits were purchased from local fruit shops in District Sheikhupura and Faisalabad. The cleaned peels were then dried in shade for 7 days. Good quality dried peels were selected and powdered to uniform particle size using an electric grinder. M. oleifera taxonomic classification is as follows:

Kingdom Plantae
Division Magnoliophyta
Class Magnoliopsida
Order Capparales
Family Moringaceae
Genus Moringa
Species oleifera

2.2 Chemicals

Acetic acid (1%), potassium phosphate buffer (0.2 M, pH 6.6), potassium ferricyanide (1%), trichloro acetic acid (10%), ferric chloride (FeCl₃·6H₂O) (0.1%), Na₂CO₃ (20%), AlCl₃ (10%), gallic acid, NaNO₂, (5%), 1 M NaOH, Folin–Ciocalteu reagent, 2,2-diphenyl-1-picrylhydrazyl (DPPH) reagent, ABTS (2,2′-azino-di-[3-ethyl benzthiazoline sulfate (6)]) reagent, distilled water, n-hexane solvent, acetone, methanol, ethanol, CS powder, PC powder, gum Arabic, sodium sulfate, XG, Tween 80, and M. oleifera seed oil.

2.3 Extraction of oil

Dried seeds were powered to uniform particle size. The sample-to-solvent ratio was kept constant for all the methods. About 50 g of the seed powder was pre-weighed for oil extraction that was carried out in Soxhlet apparatus (Model EMEA3) by 250–300 ml n-hexane (96% purity) as a solvent at 60°C. The extraction process was repeated for 4–6 runs to obtain a reasonable quantity of oil for 2–6 h. After extraction, the oil was recovered by evaporating the solvent under a vacuum in a rotary evaporator (Model 503) at 65°C [23]. The seed residues obtained after the defatting process were used to extract the antioxidants. The same protocol was repeated for grapefruit peel defatting.

2.4 Extraction of antioxidants

For antioxidant extraction, 30 g of seed residue (in each batch) was soaked in 60 ml of 80% methanol at room temperature for 24 h. After 30 min successful sonication, the samples were allowed to homogenize on an orbital shaker (120 rpm) for 7–8 h. The extracts were separated from the residues through the Whatman No. 1 filter paper. The residues were rinsed twice with fresh solvent. The filtrates were heated in a water bath at 45°C to evaporate the solvent for 2–4 h. The concentrated extracts were allowed to stand in the air to evaporate any residual solvent for a maximum 24 h. The concentrated extracts were weighed to calculate the yield and then at 4°C until further use [24] (Figure 1). The same protocol was followed to obtain the antioxidant extracts of grapefruit peels (Figure 2).

Figure 1 Extraction of oil from M. oleifera seeds.
Figure 1

Extraction of oil from M. oleifera seeds.

Figure 2 Extraction of antioxidants from grapefruit peel/Moringza seed residues.
Figure 2

Extraction of antioxidants from grapefruit peel/Moringza seed residues.

2.5 Dispersion and emulsion preparation

The emulsions were prepared according to the method described in the literature with some modifications [25,26]. The oil in water (O/W) emulsions of Moringa seed oil (3 ml) and distilled water (2 ml) were prepared by stirring at room temperature. Aqueous dispersions of PC (0.15 g) and XG (0.1 g) were made in distilled water (Tables 1 and 2). The CS polymer stock solution was prepared by adding the exact amount of CS (0.15 g) powder into 1% acetic acid solution under mixing to disperse the particles uniformly. These dispersions were stirred separately for 1 h at room temperature. These aqueous solutions of PC, CS, and XG were added separately into final O/W emulsions at 800 rpm for 3 h using a mechanical stirrer. For antioxidant oleogels, the extracts of GAEs/MAEs (0.5, 1, and 1.5%) were substantially dispersed in the O/W emulsions (Table 3). The final emulsions were refrigerated at 4°C for 24 h to ensure complete hydration.

Table 1

Formulation trials screened to find stable oleogel emulsions with PC as the oleogelator

Sample code MO (ml) DW (ml) CS (g) PC (g) AG (g) XG (g) Tween 80 (μl) Stability status
OPCAG1 5 3.5 — 0.05 0.05 — — Broken
OPCAG2 5 3.5 — 0.05 0.1 — 100 Broken
OPCAG3 5 3.5 — 0.1 0.1 — 100 Broken
OPCXG1 5 3.5 — 0.05 — 0.1 100 Stable (4 days)
OPCXG2 5 3.5 — 0.1 — 0.1 100 Stable (one week)
Table 2

Composition of the synthesized oleogels without the addition of antioxidant

Sample code MO (ml) PC (g) CS (g) XG (g) Tween 80 (μl) DW (ml)
OPC27 3 0.15 — 0.1 100 2
OCS30 3 — 0.45 0.1 100 2
OPCCS1 3 0.23 0.075 0.1 100 2
OPCCS2 3 0.075 0.23 0.1 100 2
OPCCS3 3 0.15 0.15 0.1 100 2
Table 3

Composition of synthesized oleogels with antioxidant extracts

Sample Code MO (g) MAEs (%) GFAEs (%) PC (g) CS (g) XG (g) DW (ml)
MCPC 0.5% 3 0.5% — 0.075 0.23 0.1 2
MCPC 1% 3 1% — 0.075 0.23 0.1 2
MCPC 1.5% 3 1.5% — 0.075 0.23 0.1 2
GCPC 0.5% 3 — 0.5% 0.075 0.23 0.1 2
GCPC 1% 3 — 1% 0.075 0.23 0.1 2
GCPC 1.5% 3 — 1.5% 0.075 0.23 0.1 2

2.6 Emulsion-template oleogel preparation

The emulsions were dried using a lyophilizer (freeze drier) at 4°C for 24 h and a hot air oven at 50°C for 24–48 h to remove the water phase. The drying process was monitored until reaching a constant weight. The dried samples were ground with a domestic grinder for 5 s to obtain oleogels [4] (Figure 3).

Figure 3 Schematic for the synthesis of emulsion template oleogel.
Figure 3

Schematic for the synthesis of emulsion template oleogel.

2.7 Determination of OBC

The OBC of oleogels was measured using the centrifuge method. The weight of an empty (1.5 ml) Eppendorf tube was measured. Approximately 1 g of oleogel sample was refrigerated for 1 h. Then, the weight of the filled Eppendorf tube was measured and was centrifuged at 8,000 rpm for 5 min. The supernatant as released liquid oil was drained completely by turning over the tubes on the filter paper for 30 min. The weight of the Eppendorf tube after the complete removal of oil was measured. The oil loss values were calculated using equation (1) [27]:

OBC ( % ) = 100 – Released Oil ( 100 % ) ,

(1) Released oil ( % ) = ( b − a ) – ( c − a ) / ( b − a ) × 100 .

2.8 Determination of antioxidant activity

The radical scavenging activity of Moringa seeds and grapefruit peel methanolic extracts against the DPPH radical was determined according to Yaqoob et al. [28]. About 50 μl of the extract for each six samples of Moringa and ten samples of grapefruit was taken separately in 4.5 ml of ethanol. About 0.5 ml of freshly prepared solution of DPPH was added to the reaction mixture, and the absorbance value was measured at 517 nm after 10 and 30 min. Radical scavenging activity was calculated using the following equation:

(2) % inhibition × A blank − A sample / A blank × 100 .

2.9 Determination of total phenolic content (TPC)

The TPC of grapefruit peel/Moringa seed extracts was determined following the procedure of Yaqoob et al. [28]. The TPC of the extracts was determined using the Folin–Ciocalteu reagent. About 50 mg from each Moringa and grapefruit extract was taken separately, containing 0.5 ml of freshly prepared diluted Folin–Ciocalteu reagent. The reaction mixture was diluted to 7.5 ml with deionized water. These mixtures were kept at room temperature for 10 min. Then, 1.5 ml of 20% sodium carbonate (w/v) was added to the mixture. Afterward, the mixture was heated at 40°C for 20 min and cooled in the ice bath. The absorbance was measured at 755 nm on a UV spectrophotometer. The amount of total phenolics was calculated by using a calibration curve for gallic acid (R 2 = 0.9988). The results are expressed as gallic acid (mg/10 g) of extract.

2.10 Determination of total flavonoid content (TFC)

TFC was determined following the procedure by Sultana et al. [29]. 1 ml of aqueous containing 0.1 g/ml of the grapefruit peel/Moringa seed extract was taken in 5 ml of distilled water, followed by the addition of 0.3 ml of 5% NaNO₂. After 5 min, 0.6 ml of 10% AlCl3 was added to the reaction mixture. After another 5 min, 2 ml of 1 M NaOH was added, and the volume was made up with distilled water. The solution was homogenized, and finally, absorbance was measured at 510 nm. TFC was expressed as catechol equivalents per grapefruit peel/Moringa seed extract.

2.11 Determination of reducing power

The reducing power of the grapefruit peel/Moringa seed extracts was determined by Sultana et al. [29]. About 10 mg of seed extracts was added to 5 ml of sodium phosphate buffer (0.2 M, pH 6.6) and 5 ml of potassium ferricyanide (1%). The mixture was shaken for 20 min at 50°C. Then, 5 ml of 10% trichloroacetic acid was added, and finally, 1.0 ml of ferric chloride (0.1%) was added to the reaction mixture. The absorbance was measured at 700 nm.

2.12 Characterization of oleogels

The microstructure of emulsion template oleogels was visualized with a scanning electron microscope (SEM). Scanning electron microscopy (JSM IT-100 Jeol, Japan) was employed to obtain the micrographs of the samples. The textural properties were studied using a compound light microscope. A small drop of heated sample was placed onto a microscope glass slide and conditioned at 4°C overnight. The samples were analyzed at 25°C using a 20× magnification [30].

2.13 FTIR analysis

The IR spectra of oleogels were obtained using a Spectrum 65 FTIR spectrophotometer equipped with an attenuated total reflection sampling accessory. All the measurements were recorded between the wavelengths of 4,000 and 600 cm−1 [27].

2.14 Thermal analysis

Thermal measurements of 8–9 mg of the oleogel sample were carried out using a differential scanning calorimeter (DSC; DSC 250, TA Instruments, USA). The oleogel samples in sealed aluminum pans were heated from 30 to 150°C at a heating rate of 5°C/min under N2 atmosphere.

2.15 Determination of oxidative stability

The primary lipid oxidation of oleogel samples was determined by peroxide value (PV) measurements. Oxidative stability during the storage period of oleogels at 3–4°C was determined following the AOCS method [31]. The PVs (meq O2 kg−1) of the oleogel samples were measured by the acetic acid–chloroform method and potassium iodide solution.

2.16 Statistical analysis

All measurements were taken in triplicates of the oleogel samples. The results are represented as mean values with standard deviations. The data were analyzed by ANOVA, the significance level (α) was 0.05, and the multiple comparisons of the means were accomplished by Tukey’s test using SPSS statistics.

3 Results and discussion

3.1 DPPH antioxidant activity and ferric reducing power (FRAP) assay

The extracts prepared with 80% aqueous methanol were the most effective scavengers of DPPH. The methanolic extracts of grapefruit peels and M. oleifera seed extracts were analyzed to determine their radical scavenging power. In the current analysis, ten extracts that were taken from the peel powder of grapefruit showed the highest DPPH radical scavenging activity. The GAEskp1, GAEskp2, GAEskp4, GAEskp5, GAEfsd6, GAEfsd7, and GAEfsd8 samples showed maximum antioxidant activity with percentages of 80, 82, 90, 88, 84, 80 and 86%, respectively, as shown in Figure 4a.

Figure 4 DPPH scavenging activities (%) of methanolic grapefruit peel extracts collected from two different regions and methanolic extracts of M. oleifera seed using DPPH.
Figure 4

DPPH scavenging activities (%) of methanolic grapefruit peel extracts collected from two different regions and methanolic extracts of M. oleifera seed using DPPH.

Similarly, M. oleifera seed extracts were also analyzed for their radical scavenging power. Out of six seed extracts, MAE3, MAE5, and MAE6 exhibited 84.52, 83.25, and 82.16% radical inhibition, respectively. The remaining samples also showed good scavenging activity (Figure 4b). However, the results revealed that all the samples from grapefruit peels and M. oleifera seed extracts have high and significant antioxidant capacities. Thus, plant peels and seeds are a good source of antioxidants. In previous studies, it was reported that grapefruit, lemon, and orange peels significantly showed the highest radical scavenging powers of 76.4, 73.2, and 70.5%, respectively (Table 4).

Table 4

Antioxidant activities of grapefruit peels (collected from Sheikhupura and Faisalabad) and M. oleifera seed (collected from Gojra and Faisalabad) residue extracts (values are mean ± standard deviation, n = 3)

Antioxidant extracts DPPH scavenging activity (%) FRAP TFC (mg CE/g-dw) TPC (mg GAE/g-dw)
GAESkp1 70.57 ± 1.97abc 1.06 ± 0.03c 1.61 ± 0.03i 14.13 ± 0.02i
GAESkp2 86.55 ± 1.51fg 1.36 ± 0.02f 1.33 ± 0.04ef 13.96 ± 0.03h
GAESkp3 88.30 ± 0.61g 1.24 ± 0.02def 1.54 ± 0.01hi 13.90 ± 0.02gh
GAESkp4 85.43 ± 0.92fg 1.04 ± 0.03bc 1.42 ± 0.03fg 13.79 ± 0.02
GAESkp5 78.39 ± 1.76de 1.30 ± 0.04ef 1.45 ± 0.02gh 13.73 ± 0.03ef
GAEFsd1 86.75 ± 1.88fg 0.92 ± 0.03ab 1.48 ± 0.02gh 13.68 ± 0.03def
GAEFsd2 68.61 ± 2.00ab 1.64 ± 0.02gh 1.41 ± 0.02fg 13.61 ± 0.03cde
GAEFsd3 82.41 ± 1.45efg 0.89 ± 0.01a 1.43 ± 0.03g 13.55 ± 0.04bcd
GAEFsd4 82.43 ± 1.45efg 1.02 ± 0.01bc 1.22 ± 0.02bcd 13.48 ± 0.02bc
GAEFsd5 66.48 ± 2.02a 1.13 ± 0.09cd 1.32 ± 0.01e 13.44 ± 0.03b
MAEGoj1 77.91 ± 1.82de 1.65 ± 0.05gh 1.16 ± 0.05bc 7.74 ± 0.02a
MAEGoj2 74.45 ± 1.06bcd 1.56 ± 0.07g 1.06 ± 0.05a 7.72 ± 0.01a
MAEGoj3 84.89 ± 3.75fg 1.99 ± 0.05i 1.24 ± 0.02cde 7.67 ± 0.01a
MAEFsd4 75.06 ± 1.70cd 1.21 ± 0.02de 1.14 ± 0.04ab 7.65 ± 0.02a
MAEFsd5 83.25 ± 2.75efg 1.66 ± 0.05gh 1.30 ± 0.03de 7.64 ± 0.01a
MAEFsd6 82.16 ± 2.62ef 1.73 ± 0.03h 1.31 ± 0.01de 7.62 ± 0.02a

All experiments were performed in triplicate, and the results are reported as mean ± SD. ANOVA was performed along with Tukey’s test to compute the significant difference between different groups. Different lowercase alphabets in a column present significant statistical difference between samples.

3.2 FRAP

The results of the reducing power assay confirmed that three extracts, GAEskp2, GAEskp4, and GAEfsd7, showed maximum reducing powers of 1.388, 1.337, and 1.677, respectively, as shown in Figure 5(a). GAEskp1, GAEskp3, GAEfsd9, and GAEfsd10 have also shown high reducing powers but less than those of GAEskp2, GAEskp4, and GAEfsd7. These results were found to be in close agreement with those of Babbar et al. [32], in which Kinnow peel extracts showed a 1.60 value of reducing power.

Figure 5 Ferric reducing power of grapefruit peel extracts and of M. oleifera seed extracts (data represent the mean ± SD (n = 3).
Figure 5

Ferric reducing power of grapefruit peel extracts and of M. oleifera seed extracts (data represent the mean ± SD (n = 3).

The FRAP values of MAE3, MAE5, and MAE6 extracts were higher among the total six samples of seed extracts of M. oleifera, as shown in Figure 5(b). The extracts with higher reducing power were further chosen to be used in the synthesis of antioxidant oleogels because these extracts have a good ability to prevent the oxidation process.

3.3 Total flavonoid and phenolic content

The TFCs in Citrus paradisi peel extract range from 1.32 to 1.61 mg/g. Grapefruit peels taken from the Sheikhupura region have shown the highest TFC values. According to previously reported research, the methanolic extract of Citrus grandis exhibited 1.04 mg QE/g TFC [33]. Flavonoids and polyphenols are good hydrogen donors, and their antioxidant ability varies from one compound to another. The rate of flavonoid and phenolic content is affected by numerous factors like the presence of certain chemical groups (organic acids, aromatic amines, ascorbic acid, and sugars) that may also react with the Folin–Ciocalteu reagent. The difference in values of TFC as compared to previously reported values may be described on the basis of the nature of soil and agro-climatic conditions, different chemical compositions, and the efficiency of solvent to extract bioactive compounds. The methanolic extracts of M. oleifera seeds were analyzed for TFC determination. Catechol equivalent (mg CAE/g of aqueous extract) was used as a standard to access the flavonoid content (Figure S1). The amount of flavonoid recorded was 1.61 ± 0.01 mg CAE/g of aqueous extract from the total antioxidant content of Moringa seeds. The values ranged from 1.24 ± 0.02 to 1.61 ± 0.01 mg CAE/g of aqueous extract, as shown in Table 1. The amount of TFC was found to be lower than the study reported by Mohammed and Manan [34]. As is known, flavonoids are polyphenolic compounds whose structures consist of aromatic rings with multiple hydroxyl groups. They are mostly polar in nature; therefore, they show more solubility in polar solvents like ether. The lower amount of TFC in the case of methanolic extracts of Moringa seeds is in close agreement with a previous study [35].

The TPCs in Citrus paradisi peel extracts ranged from 13.44 (±0.03) to 14.03 (±0.02) mg/g. The grapefruit peel taken from the Sheikhupura region shows the highest TPC values compared to other extracts. These values indicated that 1 g of the peel extract contains a phenol amount approximately equivalent to 13.44–14.03 mg of pure gallic acid (Figure S1). A previous study reported that Kinnow peel has 17.5 mg GAE/g-dw of phenols [32]. The TPC of the Moringa extracts recorded was 7.74 ± 0.02 mg GAE/ml of aqueous extract of the total antioxidant content in M. oleifera seeds. The TPC was much higher than TFC, which indicated the richness of phenolic over flavonoids in the methanolic extracts of M. oleifera seed [34]. They reported a TPC of 10.179 ± 2.984 mg of GAE/g of dry matter of total antioxidant content of M. oleifera seed extract. The concentration of total phenolics can be affected or vary by cultivar, region, storage time, and methods of extraction and drying.

3.4 Determination of OBC

The OBCs of prepared oleogels ranged from 79.36 ± 0.1 to 99.94 ± 0.05. The drying process was observed by recording the fraction weight loss of emulsions periodically until it reached a constant value (Figure S3). The time required for the complete drying of emulsions in a hot air oven at 50°C ranged from 28 to 48 and 24 h at 4°C for lyophilization (Figure S4). The OBC of oleogels was not significantly influenced by the drying methods of emulsions (oven and freeze-drying). However, the freeze-drying (lyophilization) method was preferred over oven drying (Figure S5). The addition of MAEs and GAEs at 0.5, 1, and 1.5% also showed a reduction in oil loss from oleogels. This behavior can be considered due to the formation of stable concentrated emulsions because of the developing thick double layer on the oil droplets and enhancement of continuous phase viscosity in the presence of XG as a stabilizer, resulting in closely packed oleogel network and enhancement in oil entrapment [4]. The increase in the concentrations of MAEs/GAEs above 2% made the hydrophilic groups insufficient to interact with XG to form a stable double-layer interface at O/W emulsion. Therefore, 1.5 wt% was the suitable concentration for MAEs and GAEs to prepare stable oleogel. In fact, it is known that oleogelator compounds play an effective role in oil inhibition and make them stable (Figure 6). Hence, stable oleogel retaining the liquid oil was obtained with MAEs/GAEs, CS, and PC as structuring materials, which met the standard requirements of oleogels.

Figure 6 OBC (%) of lyophilized antioxidant oleogels.
Figure 6

OBC (%) of lyophilized antioxidant oleogels.

3.5 Microstructure observation

The microstructure of oleogel samples under a compound light microscope is shown in Figure S6. The polymeric entanglement in the OPCCS2 oleogel had branched chain-like networks, while in the case of antioxidant (MCPC 1.5%) oleogels, the polymeric chains appeared in bulk; the network became denser, revealing the oil phase as dark sheets. It can relate to the presence of a larger amount of tocopherol and polyphenolic content in MCPC1.5% oleogels. Also, the appearance of compact structures occurs due to the lower extent of coalescence resulting from the immobilization by the polysaccharide chain entanglements.

The morphological observation of binary component oleogels with or without antioxidant extract (MCPC) incorporation was acquired by cryo-SEM. It clearly revealed the compact aggregates, rough surfaces, and irregular morphology of the polymeric network of oleogels (Figure S7). A more inhomogeneous and rougher surface compared to non-emulsified CS and PC was mainly due to the hydrophobic patches of oleic acid. In particular, it was possible to observe a few structural changes due to the collapse of the structure during the dehydration process. Because the drying method prevents the collapsing of the colloidal network during water removal. Furthermore, the interface structured by surface-active and non-surface-active polysaccharides around the oil droplets contributed to preventing the isolation of oil droplets. A large number of oil droplets appear to be dispersed in the continuous phase of polysaccharides through close packing of oil droplets without internal contact.

3.6 FTIR analysis

The information about the chemical bond interactions in the oleogel samples was obtained by FTIR spectroscopy, which covered the wave range of 4,000–500 cm−1. A significant similarity was observed in the IR spectrum of polysaccharides. In view of the molecular nature of various components present in the oleogel samples, the IR spectra of oven-dried and lyophilized oleogels were expected to be almost identical, with peaks at nearly the same wavelengths as indicated in the FTIR spectra. There were some spectral differences between oleogels (without antioxidants) and antioxidants containing oleogels. The oven-dried oleogels of the OPC27 oleogel showed a broad peak in the region 3,283–3,468 cm−1, and the OCS30 oleogel showed peak broadening behavior at around 3,271–3,395 cm−1 (Figures 7a and S8). The OPCCS series of oleogel samples also showed broad peaks at around 3,217–3,468 cm−1 (Figures 7b and S9).

Figure 7 (a) FTIR spectra of oven-dried single oleogelator oleogel OPC27, OCS12, and OCS30. (b) FTIR spectra of oven-dried oleogelator blend oleogels OPCCS1, OPCCS2, and OPCCS3. (c) FTIR spectra of M. oleifera seed antioxidant oleogels MCPC0.5%, MCPC 1%, and MCPC 1.5%, MCPC 1%, and MCPC 1.5%. (d) FTIR spectra of grapefruit peel antioxidant oleogels GCPC0.5%, GCPC 1%, and GCPC 1.5%.
Figure 7

(a) FTIR spectra of oven-dried single oleogelator oleogel OPC27, OCS12, and OCS30. (b) FTIR spectra of oven-dried oleogelator blend oleogels OPCCS1, OPCCS2, and OPCCS3. (c) FTIR spectra of M. oleifera seed antioxidant oleogels MCPC0.5%, MCPC 1%, and MCPC 1.5%, MCPC 1%, and MCPC 1.5%. (d) FTIR spectra of grapefruit peel antioxidant oleogels GCPC0.5%, GCPC 1%, and GCPC 1.5%.

A very small peak at 3,471 cm−1 in the spectra of pure Moringa oil was observed (Figure S10).

From the spectra of polysaccharides (Figure S11), broad peaks in the 3,226–3,422 cm−1 wave range were also observed. This peak-broadening behavior corresponds to –OH stretching vibrations that are related to intermolecular or intramolecular hydrogen bonding within the chains of polysaccharides. In antioxidant-enriched oleogels, these –OH stretching peaks (Figure 7c and d) ranged from 3,217 to 3,485 cm−1. These peaks suggested the presence of intermolecular hydrogen bonding interactions in the oleogel samples due to the presence of hydroxyl groups of hydrophilic polysaccharide chains, as evident from the deformations in the 3,200–3,400 cm−1 range bands. In the formation of polymer oleogels, hydrogen bonding is considered the main interaction force. The crystal network of the ethyl-cellulose (EC) oleogel was also formed due to hydrogen bonding with the polymer chains [36].

The other peaks observed in the spectra of oleogels can also be explained by comparing them with pure Moringa oil (Figure S12) and polysaccharides. For instance, the peaks observed at 2,924 and 1,746 cm−1 revealed the abundance of triglycerides in the samples. The peaks observed at 2,924 cm−1 from pure oil and polysaccharides powder indicated C–H stretching of –CH2. Similarly, the oven-dried (2,912 cm−1), lyophilized (2,926 cm−1), and antioxidant-enriched lyophilized oleogels also showed C–H stretching vibrations of CH2 at 2,926 cm−1. The sharp intensity absorption peaks at 1,743 cm−1 were observed in Moringa oil, polysaccharides, and all oleogel samples. It confirmed the presence of C═O stretching vibrations of esters. The presence of fatty acids was confirmed by peaks at 1,631 cm−1 that relate to C═C stretching of disubstituted cis-olefins, and the intensity of this peak was used to determine the total unsaturation. The overlapped peaks identified at 1,462 and 1,354 cm−1 represented the C–H stretching of CH3 and CH2 groups, respectively, from Moringa oil and polysaccharides. At lower frequencies, the band near 726 cm−1 is assigned to the CH2 group rocking vibrations and deformation of –CH2 in cis-substituted olefins that build up the long-chain mono and PUFA of the Moringa seed oil. The appearance of peaks at 1,087 and 671 cm−1 corresponds to the C–O stretching of C–O–C and C–X bending of halo compounds.

The results revealed that oleogelation does not affect the chemical properties of the oil, and different molecular arrangements occur due to the self-assemblies of polymeric oleogelators and the oil. The appearance of spectra can be affected by oleogelation techniques and the oil. It can be noticed that there was no variability in the appearance of peaks or shifts for the oleogels in comparison to the polysaccharides and the oil, which indicates the presence of physical interactions and no changes in the chemical structures, are the reasons for oleogel formation.

3.7 DSC analysis

The DSC thermographs of Moringa-oil-structured single-component and multicomponent oleogels in the range of 30–100°C are shown in Figure S13. The heat flow (W g−1) versus temperature for the heating cycle was analyzed to determine the melting behavior of different oleogel samples. All oleogel samples exhibited single exothermic peaks. The mono-component oleogels, namely OPC27 and OCS30, had peak melting temperatures at 47 and 53°C, respectively. The overall melting behavior of XG-stabilized PC oleogel was apparently different from CS oleogel, which was probably due to the heterogeneous nature of structuring agents employed, as melting peak behavior depends mainly on their concentration and type rather than the liquid oil phase used. Therefore, the differences in thermal properties may be attributed to the properties of oleogelators. A previous study proved this thermal curve behavior of oleogel samples by using three different vegetable oils. These melting temperatures of oleogels were lower than the pure polymers.

The melting profiles of oleogels prepared with different blends (CS 75: PC 25) displayed a eutectic system. They had DSC melting peaks in between the melting peaks of mono-component oleogels. The combined features of CS and PC are presented. The OPCCS2 oleogel showed a melting exothermic peak at 43°C, whereas the melting behavior of MCPC1.5% was quite interesting. The results showed a decrease in T onst when the antioxidant extract was added to the OPCCS2-based oleogel. It had a significantly lower temperature at 42°C. These lower melting temperatures suggest the strong interactions between the structuring polymers in this proportion; the visible difference is observed in gel networks and the formation of mechanically stable gels.

This eutectic behavior can also positively correlate with the increase in oil retention of the corresponding oleogels. It is, however, interesting to note that the melting temperature of PC oleogel was lower among all the oleogel samples. Thus, the thermal behavior of all oleogel samples was acceptable for developing desirable oleogels.

3.8 Oxidative stability of the oleogel samples

The PV of the samples was found to be in line with the standard value (<10 meq O2/kg) for fresh vegetable oil. The oxidation rate of M. oleifera oil samples was found to increase with an increase in temperature. The PV values of oil samples, named OA, OB, OC, OD, and OE, were recorded as 3.36 ± 0.02, 3.92 ± 0.42, 4.66 ± 0.23, 4.66 ± 0.32, and 2.95 ± 0.18, respectively. It was suggested that the heating process caused the rapid deterioration of fatty acids, as can be observed by comparing the values with reference oil PVs. At maximum heating temperature (80°C) during this study, the value of peroxide started to decline or became constant (Figure 8(a)). This result was closely consistent with the report of Adejuma et al. [37], who also noticed a decrease in the PV of M. oleifera oil with the increase in temperature.

Figure 8 (a) PVs of M. oleifera seed oil samples heated at 50, 60, 70, and 80°C; each value is an average of three determinations, mean ± SD. (b) PVs of the oleogel samples; each value is an average of three determinations, mean ± SD. (c) PVs of lyophilized oleogel samples; each value is an average of three determinations, mean ± SD.
Figure 8

(a) PVs of M. oleifera seed oil samples heated at 50, 60, 70, and 80°C; each value is an average of three determinations, mean ± SD. (b) PVs of the oleogel samples; each value is an average of three determinations, mean ± SD. (c) PVs of lyophilized oleogel samples; each value is an average of three determinations, mean ± SD.

For oleogel samples, the oxidation rate was found to be lower than the original oil. All oleogel samples were heated at 80°C, and the changes in their PV were observed each month. As expected, the oleogel samples had effectively inhibited the oxidation of oil. The PV of oven-dried and freeze-dried oleogel samples were calculated separately, and a slight increase in PV of oven-dried samples was noticed. This may be associated with the previous heating process of emulsions during the water phase removal, which clarified that the PVs of oleogels stored at higher temperatures are always higher than those at lower temperatures; this result was consistent with the previous report [27]. The oven-dried OPC27 oleogel had a higher PV of 3.09 ± 0.09 – 5.85 ± 0.06, and the freeze-dried OPC27 oleogel had a PV of 3.04 ± 0.17 – 5.84 ± 0.11 during the 2-month storage, as shown in Figure 11(b) and (c). The oven-dried OCS30 oleogel had a higher PV of 2.71 ± 0.11 − 5.59 ± 0.38, and the freeze-dried OCS30 oleogel had a PV of 2.77 ± 0.06 – 5.62 ± 0.28. The oven-dried OPCCS2 oleogel had a higher PV of 2.28 ± 0.10 to 4.47 ± 0.10, and the freeze-dried OPCCS2 oleogel had a PV of 2.23 ± 0.06 – 4.36 ± 0.22 during 30 and 60 days of storage, respectively.

The addition of antioxidants (GAEs/MAEs) also played an important role in improving the oxidative stability of the oleogel samples. At higher concentrations (1.5%) of GAEs/MAEs, oleogels exhibited lower PV compared to the other oleogel (without extract) samples (Figures S11–S13). It ranged from 2.28 ± 0.10 to 4.35 ± 0.30 and 2.26 ± 0.19 to 4.34 ± 0.22 for GAE/MAE oleogels during 30 and 60 days, respectively.

The oleogelation of M. oleifera oil with polysaccharides and MAEs/GAEs caused inhibition of the oil phase due to its immobilization in the gel network. The stability of oleogels against the oxidation process may be attributed to the polysaccharide gel network, which entrapped the liquid oil, thereby retarding the oxidation process. The other reason for lower oxidative damage to oleogels was the addition of antioxidant extract (GAEs/MAEs), which played an essential role in improving the antioxidant activity.

4 Conclusions

These contemporary investigations substantiate the optimal formulation of Moringa oil-structured emulsion template oleogels. The biopolymers CS, PC, and XG were used at minimal concentrations to formulate mono-component and multicomponent semi-solid structures binding in the healthy liquid oil. Incorporating natural antioxidants from grapefruit peel and Moringa seed residues into these lipid systems presented a possible way to prevent oxidative damage. They exhibited better shelf-life during storage due to the antioxidant contents derived from the plant sources. Both mono- and multicomponent-formulated oleogels showed no noteworthy chemical change as confirmed by FTIR results and DSC results exhibited improved melting points of the multicomponent oleogel. The oleogels have tightly packed structures of oil droplets in the matrix of polysaccharides, adequate to prevent the coalescence of oil during water evaporation. The multicomponent oleogels prepared with varying concentrations of polysaccharides had good gel stability and OBCs. This provides insight into new dimensions of commercial food research owing to the better OBC, stability, and compatibility with the respective polymers. Further research should focus on the addition of other health-beneficial plant antioxidants, new gelling agents, and lipids in the formation of novel oleogels. Future directions include investigations regarding the long-term stability and storage of the edible oleogels within a wide range of conditions such as temperature, light, and change in active functionalities/parameters with time and the effects of these parameters on the quality and integrity of oleogels.

Acknowledgements

The authors are thankful to the Government College, University Faisalabad, for providing the facility to conduct this study. The authors also extend their appreciation to the Researchers Supporting Project number (RSP2024R457), King Saud University, Riyadh, Saudi Arabia.

  1. Funding information: This paper is financially supported with the Researchers Supporting Project number (RSP2024R457), King Saud University, Riyadh, Saudi Arabia.

  2. Author contributions: Conceptualization, original draft writing, reviewing, and editing: Nazia Yaqoob, Saima Rehman, and Nusrat Shafiq. Formal analysis, investigations, funding acquisition, reviewing, and editing: Muhammad Mohsin, Aleena Akbar, and Samir Ibenmoussa. Resources, data validation, data curation, and supervision: Gezahign Fentahun Wondmie, Yousef A. Bin Jardan, and Mohammed Bourhia.

  3. Conflict of interest: The authors declare no potential conflicts of interest with respect to the research, authorship, and/or publication of this article.

  4. Ethical approval: The conducted research is not related to either human or animal use.

  5. Data availability statement: Data will be available upon request from the corresponding author.

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Received: 2024-01-26
Revised: 2024-04-06
Accepted: 2024-05-03
Published Online: 2024-07-01

© 2024 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/chem-2024-0038
Keywords for this article
antioxidants; emulsion; grapefruit peel; Moringa seed oil; oleogel; solid fats
Creative Commons
BY 4.0

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