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Saudi Journal of Biological Sciences logoLink to Saudi Journal of Biological Sciences
. 2021 Aug 2;28(12):6915–6928. doi: 10.1016/j.sjbs.2021.07.075

Phytochemical analysis of Moringa Oleifera leaves extracts by GC-MS and free radical scavenging potency for industrial applications

Nitesh Bhalla a,b,⁎, Nitin Ingle b, Srilakshmi V Patri a, D Haranath c
PMCID: PMC8626243  PMID: 34866991

Abstract

Natural extracts have been of very high interest since ancient time due to their enormous medicinal use and researcher’s attention have further gone up recently to explore their phytochemical compositions, properties, potential applications in the areas such as, cosmetics, foods etc. In this present study phytochemical analysis have been done on the aqueous and methanolic Moringa leaves extracts using Gas Chromatography-Mass spectrometry (GCMS) and their free radical scavenging potency (FRSP) studied using 2, 2-diphenyl-1-picrylhydrazyl (DPPH) free radical for further applications. GCMS analysis revealed an extraction of range of phytochemicals in aqueous and methanolic extracts. In aqueous, extract constituents found with high percent peak area are Carbonic acid, butyl 2-pentyl ester (20.64%), 2-Isopropoxyethyl propionate (16.87%), Butanedioic acid, 2-hydroxy-2-methyl-, (3.14%) (also known as Citramalic acid that has been rarely detected in plant extracts) and many other phytochemicals were detected. Similarly, fifty-four bio components detected in methanolic extract of Moringa leaves, which were relatively higher than the aqueous extract. Few major compounds found with high percent peak area are 1,3-Propanediol, 2-ethyl-2- (hydroxymethyl)- (21.19%), Propionic acid, 2-methyl-, octyl ester (15.02%), Ethanamine, N-ethyl-N-nitroso- (5.21%), and 9,12,15-Octadecatrienoic acid etc. FRSP for methanolic extract was also recorded much higher than aqueous extract. The half-maximal inhibitory concentration (IC50) of Moringa aqueous extract observed is 4.65 µl/ml and for methanolic extract 1.83 µl/ml. These extracts can act as very powerful antioxidants, anti-inflammatory ingredient for various applications in diverse field of food, cosmetics, medicine etc.

Keyword: Moringa, Gas chromatography-mass spectra, Phytochemicals, Free radical scavenging, IC50, Antioxidant

1. Introduction

Plants and extracts of their various sections have been used for their medical characteristics and to cure specific ailments as well as general tonics, meals, and other methods to increase the body's immunity and vigor since ancient times (Ullah et al., 2020, Ageel et al., 1986, Gamal et al., 2010, Purena et al., 2018). However, since last few decades the interest of researchers has gone up dramatically to understand their detailed compositions and also to explore and establish their potential applications in diverse areas. In fact, it is the need of the hour to leverage the vital power of the nature to combat proliferating diseases like cancer, heart attacks, diabetes, rapid skin aging etc. and upcoming varieties of new alarming health concerns like recent concerns of Coronavirus disease in 2019 (COVID-19), which affects the respiratory system acutely (Varahachalam et al., 2021, Paliwal et al., 2020).

Different parts like seeds, roots, stem, bark, leaves, flower and fruits of the plant have their own phytochemical compositions and potential medicinal properties. Moringa have various species across the globe which are known for their variety of usages few examples of Moringa species are Moringa longituba, Moringa drouhardii, Moringa ovalifolia etc. (Leone et al., 2015). Moringa Oleifera is one of the magical plants considered in India due to its high medicinal properties. However, there is still a lot to unleash the potential of Moringa Oleifera by understanding their phytocomponents and variation in extraction due to solvents, understanding their potential properties and to establish their applications in various fields. The present study is focused to investigate the phytochemical composition of the Moringa Oleifera leave’s aqueous and alcoholic extracts by GC-MS and their free radical scavenging potencies, which make them useful for their further applications in cosmetic products to prevent skin damage due to free radicals generated because of pollution, UV from sunlight, smoke, also for animal feed etc.

2. Materials and methods

2.1. Materials

Methanol of 99.8% purity, HPLC grade from SD fine chemical limited, distilled water having pH 5.3–7 and conductivity 2µS/cm. Raw leaves powder of Moringa Oleifera of India origin grown in the climate of tropics and sub tropics were used for the investigation. Extra pure 2,2-Diphenyl-1-Picrylhydrazyl (DPPH) from SRL Pvt. Ltd was used for the free radical scavenging studies.

2.2. Preparation of aqueous and Methanolic extracts

The suspension of 5% Moringa Oleifera leaves were prepared in distilled water and in Methanol separately and were subjected to continuous stirring at 45–50 °C for 8 h respectively. The resultant samples were filtered through Whatman filter paper 1 to extract the phytochemicals. The filtrates were concentrated by evaporating the solvents and were used to prepare the samples for further analysis.

2.3. GC-MS analysis

The analysis of extracted phytochemicals of M. Oleifera leaves were done using GC-MS Agilent Technologies-7820A GC system. Gas Chromatogram coupled with Mass Spectrometer of Agilent Technologies-5977MSD equipped with an Agilent Technologies GCMS capillary column HP-5MS (30 m × 0.25 mm ID × 0.25µ) composed of 5% diphenyl 95% Dimethyl polysiloxane. An electron ionization system with ionizing energy of 70 eV was used. Helium gas (99.99%) was used as the carrier gas at constant flow rate 1 mL/min and an injection volume of 1 µl was employed at split ratio of 50:1, injector temperature was at 60 ˚C and ion source temperature was at 250˚C. Mass spectra were recorded using voltage of 70 eV. The relative percentage amount of each component were calculated by comparing its average peak area to the total areas, software of GC-MS Mass Hunter used for spectra and chromatograms analysis.

2.4. Phytocomponents identification

The phytochemicals were identified based on their retention time, percentage of peak area and pattern of mass spectra and its comparison with the data of library of NIST11.LIB of National Institute of Standards and Technology (NIST).

2.5. Anti-oxidant/free radical scavenging potency (FRSP) using diphenyl picrylhydrazyl (DPPH)

The Anti-oxidant efficacy and in other words free radical scavenging potency (FRSP) of the aqueous and methanolic extract of the Moringa leaves powder were determined by using DPPH. Methanolic solution of 1.52*10-4 M of DPPH was used in 1:1 ratio with Moringa aqueous and methanolic extracts at varying concentrations, studied the scavenging activity as a function of time. FRSP percentage rate was studied after incubating the mixture of DPPH and extracts for 30 min and recording the UV absorption at 517 nm. The same was used to calculate the concentration of antioxidant required to reduce the concentration of DPPH to 50% (IC50). Higher value of IC50 indicates the lower antioxidant activity and vice a versa. The control samples were prepared using DPPH solution and mixing only with respective solvents (Aqua/Methanol) at 1:1 ratio and measured at 517 nm.

FRSP% = (Controlabs - Sampleabs) x100/Controlabs

3. Results

3.1. Phytocomponent identification by GC MS of aqueous extract of M. Oleifera leaves powder

The GC-MS profile of the aqueous extract of M. Oleifera leaves is shown in Fig. 1, which reflects 25 peaks of biomolecules. Table 1 presents the phytocomponents, their retention time, peak area percentage and Molecular weight. Chemical structure of active components and their known key applications like medicinal, cosmetics etc. are tabulated in Table 2. Few major compounds found with high percent peak area are Carbonic acid, butyl 2-pentyl ester (20.64%), 2-Isopropoxyethyl propionate (16.87%), 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- (8.98%), and 1,3-Dioxolan-2-one, 4,5-dimethyl- (6.16%) additional compounds with reasonable percentage of peak area are Tetra acetyl-d-xylonic nitrile (5.03%), Azetidin-2-one 3,3-dimethyl-4-(1-aminoethyl)- (4.67%), 1,3-Dihydroxyacetone dimer (3.85%), Alpha-D-Glucose (3.44%), and Butanedioic acid, 2-hydroxy-2-methyl-, (3.14%) which is rarely been detected in plant extracts and have various applications.

Fig. 1.

Fig. 1

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GC MS of Moringa O. leaves aqueous extract.

Table 1.

List of phytochemicals identified in aqueous extract of Moringa O. leaves, their retention time and peak area% with molecular weight (grams/mole).

Sr. No. RT Peak Area % Library/ID Molecular Weight (g/mol)
1 7.63 3.8551 1,3-Dihydroxyacetone dimer 180
2 11.42 3.2396 Acetic acid, [(aminocarbonyl)amino]oxo- 132
3 15.54 2.2433 4(1H)-Pyrimidinone, 2,6-diamino- 126
4 17.89 8.9858 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- 144
5 20.65 1.1214 2-Hexynoic acid 112
6 21.01 3.1422 Butanedioic acid, 2-hydroxy-2-methyl-, (S)- 148
7 21.42 1.9275 3,3′-Iminobispropylamine 131
8 21.52 0.0774 1-Hexanamine 101
9 22.01 6.1627 1,3-Dioxolan-2-one, 4,5-dimethyl- 116
10 25.45 1.3083 2-Butenethioic acid, 3-(ethylthio)-, S-(1-methylethyl) ester 204
11 25.63 3.0349 Propanamide, N,N-dimethyl- 101
12 26.21 16.8738 2-Isopropoxyethyl propionate 160
13 27.41 2.5622 D-Mannoheptulose 210
14 29.82 4.6738 Azetidin-2-one 3,3-dimethyl-4-(1-aminoethyl)- 142
15 30.29 20.6431 Carbonic acid, butyl 2-pentyl ester 188
16 30.55 5.0379 Tetra acetyl-d-xylonic nitrile 343
17 31.08 3.445 .alpha.-D-Glucose 180
18 34.11 1.2587 1H-Cyclopenta[c]furan-3(3aH)-one, 6,6a-dihydro-1-(1,3-dioxolan-2-yl)-, (3aR,1-trans,6a-cis)- 196
19 37.97 1.5253 3-[1-(4-Cyano-1,2,3,4-tetrahydronaphthyl)]propanenitrile 210
20 38.24 1.4067 Quinolinium, 1-ethyl-, iodide 285
21 40.03 0.9462 N-Isopropyl-3-phenylpropanamide 191
22 40.22 0.7335 Propanamide 73
23 40.88 0.8805 1,2-Ethanediamine, N-(2-aminoethyl)- 103
24 41.87 4.3169 1,4-Benzenediol, 2-methyl- 124
25 42.05 0.5981 Ethene, ethoxy- 72
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Table 2.

Phytochemicals in aqueous extract of Moringa O. leaves, their structure from NIST library and known potential applications wherever applicable.

Ingredients Structure Key Applications (if any readily available)
1,3-Dihydroxyacetone dimer graphic file with name fx1.gif Synthesis of polymeric biomaterials (Zelikin and Putnam, 2005)
Acetic acid, [(aminocarbonyl)amino]oxo- graphic file with name fx2.gif
4(1H)-Pyrimidinone, 2,6-diamino- graphic file with name fx3.gif Hydroxy and amino Pyrimidines are of great interest in natural products and in the development of new drugs for various diverse areas like anti-cancer (Skoweranda et al., 1990)
4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- graphic file with name fx4.gif Strong Anti-oxidant (Yu et al., 2013, Čechovská et al., 2011)
2-Hexynoic acid graphic file with name fx5.gif As precursor for synthesizing various biological metabolites like leucotrienes, oxylipins (Starostin et al., 2000)
Butanedioic acid, 2-hydroxy-2-methyl-, (S)- graphic file with name fx6.gif One of the rarely identified component in plant extracts. Mobilize the Phosphates in soil for agricultural applications to enhance the P availability (Khorassani et al., 2011)
3,3′-Iminobispropylamine graphic file with name fx7.gif This is also among the rare component identified in plant have various role in plant as well as medicinal antitumor active (Rodriguez-Garay et al., 1989, Sunkara et al., 1988, Nishio et al., 2019)
1-Hexanamine graphic file with name fx8.gif
1,3-Dioxolan-2-one, 4,5-dimethyl- graphic file with name fx9.gif Precursor for various drugs and cyclic Carbonates have applications in Electrochemical energies (Takebe et al., 1984, Hagiyama et al., 2008)
2-Butenethioic acid, 3-(ethylthio)-, S-(1-methylethyl) ester graphic file with name fx10.gif
Propanamide, N,N-dimethyl- graphic file with name fx11.gif
2-Isopropoxyethyl propionate graphic file with name fx12.gif
D-Mannoheptulose graphic file with name fx13.gif D-Mannoheptulose widely studied for its activity against breast cancer and to suppress the D-glucose induced insulin release. (Al-Ziaydi et al., 2020, Courtois et al., 2001)
Azetidin-2-one 3,3-dimethyl-4-(1-aminoethyl)- graphic file with name fx14.gif Anti-inflammatory, ulcerogenic, and analgesic activities (Siddiqui et al., 2010)
Carbonic acid, butyl 2-pentyl ester graphic file with name fx15.gif
Tetra acetyl-d-xylonic nitrile graphic file with name fx16.gif Anti-tumor and Anti-oxidant (Imad et al., 2015, Kanhar and Sahoo, 2018)
Alpha-D-Glucose graphic file with name fx17.gif Source of energy, highly effective and used in food, medicine and its derivatives also have many medicinal use. (Shendurse and Khedkar, 2016, Cancelas et al., 2000)
1H-Cyclopenta[c]furan-3(3aH)-one, 6,6a-dihydro-1-(1,3-dioxolan-2-yl)-, (3aR,1-trans,6a-cis)- graphic file with name fx18.gif
3-[1-(4-Cyano-1,2,3,4-tetrahydronaphthyl)]propanenitrile graphic file with name fx19.gif
Quinolinium, 1-ethyl-, iodide graphic file with name fx20.gif
N-Isopropyl-3-phenylpropanamide graphic file with name fx21.gif
Propanamide graphic file with name fx22.gif Propanamide derivatives studied for antimicrobial and antiviral efficacy (Ölgena et al., 2008)
1,2-Ethanediamine, N-(2-aminoethyl)- graphic file with name fx23.gif
1,4-Benzenediol, 2-methyl- graphic file with name fx24.gif
Ethene, ethoxy- graphic file with name fx25.gif
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3.2. Phytocomponent identification by GC-MS of Methanolic extract of M. Oleifera leaves

The GC-MS profile of the methanolic extract of M. Oleifera leaves is shown in Fig. 2, which reflects 54 peaks of biomolecules. Table 3 presents the phytocomponents, their retention time, peak area percentage and Molecular weight. Chemical structure of active components and their known key applications like medicinal, cosmetics etc. are tabulated in Table 4. Few major compounds found with high percent peak area are 1,3-Propanediol, 2-ethyl-2- (hydroxymethyl)- (21.19%), Propionic acid, 2-methyl-, octyl ester (15.02%), Ethanamine, N-ethyl-N-nitroso- (5.21%), and 9,12,15-Octadecatrienoic acid, (Z,Z,Z)- (5.00%) additional compounds with reasonable percentage of peak area are 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- (4.18%), Benzeneacetonitrile, 4-hydroxy- (3.47%), 3-Deoxy-d-mannoic lactone (3.29%), n-Hexadecanoic acid (2.57%) and Monomethyl malonate (2.56%).

Fig. 2.

Fig. 2

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GC MS of Moringa O. leaves Methanolic extract.

Table 3.

List of phytochemicals identified in methanolic extract of Moringa O. leaves, their retention time and peak area% with molecular weight (grams/mole).

Sr.No RT Peak Area % Library/ID Molecular Weight (g/mol)
1 7.66 2.4651 Dihydroxyacetone 90
2 11.5285 1.8656 Glycerin 92
3 11.7064 0.5327 Erythritol 122
4 14.0612 2.5684 Monomethyl malonate 118
5 15.5626 0.6434 4,5-Diamino-6-hydroxypyrimidine 126
6 17.8911 4.1801 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- 144
7 18.9343 0.2105 Furan, 2,3-dihydro-4-methyl- 84
8 20.4278 0.6806 Catecholborane 120
9 20.6515 0.8121 2-Fluoropyridine 97
10 21.017 1.4375 1,2,3-Propanetriol, 1-acetate 134
11 21.2273 0.1746 3,4-Furandiol, tetrahydro-, trans- 104
12 21.4101 0.5114 1-Nitro-.beta.-d-arabinofuranose, tetraacetate 363
13 21.5424 0.1172 1,8-Diamino-3,6-dioxaoctane 148
14 22.033 1.7997 1,7-Diaminoheptane 130
15 22.6606 0.454 N,N-Dimethylacetamide 131
16 22.8934 0.5466 2-Oxoglutaric acid 146
17 23.1495 0.9008 Oxazolidine, 2-ethyl-2-methyl- 115
18 23.7541 0.7112 Heptanal 114
19 25.4554 0.4293 6-Methoxy-3-pyridazinethiol 142
20 25.6675 0.5971 3-Piperidinol 101
21 26.4192 21.1909 1,3-Propanediol, 2-ethyl-2-(hydroxymethyl)- 134
22 27.4032 3.4763 Benzeneacetonitrile, 4-hydroxy- 133
23 27.6817 0.395 Benzenebutanal, .gamma.,4-dimethyl- 176
24 28.8207 0.4491 2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-4,4,7a-trimethyl- 180
25 30.0026 5.2161 Ethanamine, N-ethyl-N-nitroso- 102
26 30.3938 15.0279 Propanoic acid, 2-methyl-, octyl ester 200
27 30.7101 3.2947 3-Deoxy-d-mannoic lactone 162
28 31.0768 0.3814 d-Glycero-d-ido-heptose 210
29 31.1206 0.3314 D-erythro-Pentose, 2-deoxy- 134
30 32.4351 0.5345 N-Methoxy-1-ribofuranosyl-4-imidazolecarboxylic amide 273
31 33.2282 0.5847 Formamide, N,N-dimethyl- 73
32 33.4717 0.5651 d-Talonic acid lactone 178
33 33.7365 0.482 Sorbitol 182
34 33.9282 0.5189 Allo-Inositol 180
35 34.1181 1.595 D-chiro-Inositol, 3-O-(2-amino-4-((carboxyiminomethyl)amino)-2,3,4,6-tetradeoxy-.alpha.-D-arabino-hexopyranosyl)- 379
36 34.3555 1.1254 Allo-Inositol 180
37 34.5368 1.1121 Scyllo-Inositol 180
38 34.7792 2.0264 Muco-Inositol 180
39 34.8409 0.8749 Allo-Inositol 180
40 34.8998 2.0545 Inositol 180
41 35.6364 0.4822 Cyclohexane, 1-methyl-4-(2-hydroxyethyl)- 142
42 37.3767 0.8519 Hexadecanoic acid, methyl ester 270
43 37.9829 2.5703 n-Hexadecanoic acid 256
44 38.9185 0.3737 Phenol, 2-methyl- 108
45 39.2935 0.967 (1S)-Propanol, (2S)-[(tert.butyloxycarbonyl)amino]-1-phenyl- 251
46 39.7227 1.0307 9-Octadecenoic acid (Z)-, methyl ester 296
47 39.8325 0.9664 Phytol 296
48 40.0418 5.0063 9,12,15-Octadecatrienoic acid, (Z,Z,Z)- 278
49 40.2184 1.2051 Octadecanoic acid 284
50 40.3832 0.4257 4-Allyl-3-(dimethylhydrazono)-2-methylhexane-2,5-diol 228
51 40.8886 0.6056 Benzyl .beta.-d-glucoside 270
52 41.0816 0.1698 4,6-dimethyl-2-propyl-1,3,5-dithiazinane 191
53 41.8877 0.545 1,3-Benzenediol, 2-methyl- 124
54 42.0626 1.4694 9-Octadecenamide, (Z)- 281
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Table 4.

Phytochemicals in methanolic extract of Moringa O. leaves, their structure from NIST library and known potential applications wherever applicable.

Ingredients Structure Key applications (if any readily known)
Dihydroxyacetone graphic file with name fx26.gif Dihydroxyacetone (DHA) are being used in Sunless tanning type of products. (Huang et al., 2017)
Glycerin graphic file with name fx27.gif Used as humectant, Moisturizer
having application in cosmetics and Medicines (Sagiv et al., 2001)
Erythritol graphic file with name fx28.gif Antioxidant
Improve blood vessel function in people with type 2 diabetes
(den Hartog et al., 2010)
Monomethyl malonate graphic file with name fx29.gif
4,5-Diamino-6-hydroxypyrimidine graphic file with name fx30.gif Analogues are used for various Medicinal properties like antimicrobial (Abbas et al., 2017)
4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- graphic file with name fx31.gif Strong Anti-oxidant (Yu et al., 2013, Čechovská et al., 2011)
Furan, 2,3-dihydro-4-methyl- graphic file with name fx32.gif
Catecholborane graphic file with name fx33.gif Versatile compound for various organic synthesis (Brown and West, 2001, Paquette et al., 2009)
2-Fluoropyridine graphic file with name fx34.gif
1,2,3-Propanetriol, 1-acetate graphic file with name fx35.gif
3,4-Furandiol, tetrahydro-, trans- graphic file with name fx36.gif
1-Nitro-.beta.-d-arabinofuranose, tetraacetate graphic file with name fx37.gif
1,8-Diamino-3,6-dioxaoctane graphic file with name fx38.gif
1,7-Diaminoheptane graphic file with name fx39.gif Malaria treatment (Kaiser et al., 2001)
N,N-Dimethylacetamide graphic file with name fx40.gif Novel antiviral agent (He et al., 2005)
2-Oxoglutaric acid graphic file with name fx41.gif Biosynthesis of Carotenoids in Chloroplasts (Liu et al., 2018)
Oxazolidine, 2-ethyl-2-methyl- graphic file with name fx42.gif
Heptanal graphic file with name fx43.gif
6-Methoxy-3-pyridazinethiol graphic file with name fx44.gif
3-Piperidinol graphic file with name fx45.gif Anti-tuberculosis agent (Markad et al., 2015)
1,3-Propanediol, 2-ethyl-2-(hydroxymethyl)- graphic file with name fx46.gif
Benzeneacetonitrile, 4-hydroxy- graphic file with name fx47.gif
Benzenebutanal, .gamma.,4-dimethyl- graphic file with name fx48.gif
2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-4,4,7a-trimethyl- graphic file with name fx49.gif Anti‑arthritic activity (Rhew et al., 2020)
Ethanamine, N-ethyl-N-nitroso- graphic file with name fx50.gif Boost immune system. (Zaitseva et al., 2018)
Propanoic acid, 2-methyl-, octyl ester graphic file with name fx51.gif Anti-Microbial properties (Hamedi et al., 2019)
3-Deoxy-d-mannoic lactone graphic file with name fx52.gif
d-Glycero-d-ido-heptose graphic file with name fx53.gif Inhibition of insulin secretion & Hexokinase (Scruel et al., 1998)
D-erythro-Pentose, 2-deoxy- graphic file with name fx54.gif
N-Methoxy-1-ribofuranosyl-4-imidazolecarboxylic amide graphic file with name fx55.gif
Formamide, N,N-dimethyl- graphic file with name fx56.gif
d-Talonic acid lactone graphic file with name fx57.gif
Sorbitol graphic file with name fx58.gif Help to prevent hyperglycemia (Wick et al., 1951)
Protect and rejuvenation of skin from oxidative stress (Manca et al., 2018)
Allo-Inositol graphic file with name fx59.gif Control the il6 level to reduce the inflammation (Bizzarri et al., 2020)
D-chiro-Inositol, 3-O-(2-amino-4-((carboxyiminomethyl)amino)-2,3,4,6-tetradeoxy-.alpha.-D-arabino-hexopyranosyl)- graphic file with name fx60.gif Type 2 Diabetes Treatment (Pintaudi et al., 2016)
Allo-Inositol graphic file with name fx61.gif Control the il6 level to reduce the inflammation (Bizzarri et al., 2020)
Scyllo-Inositol graphic file with name fx62.gif Treat mild to moderate Alzheimer's disease. (Choi et al., 2010)
Muco-Inositol graphic file with name fx63.gif Oligomer of muco-inositol act as glycosidase inhibitors (Freeman and Hudlicky, 2004)
Allo-Inositol graphic file with name fx64.gif Control the il6 level to reduce the inflammation (Bizzarri et al., 2020)
Inositol graphic file with name fx65.gif Inositol and its derivative are known for treatment of Polycystic ovary syndrome (PCOS) (Kamenov and Gateva,, Mariano and Gianfranco, 2014)
Cyclohexane, 1-methyl-4-(2-hydroxyethyl)- graphic file with name fx66.gif
Hexadecanoic acid, methyl ester graphic file with name fx67.gif Anti-inflammatory (Saeed et al., 2012)
n-Hexadecanoic acid (palmitic acid) graphic file with name fx68.gif Anti-inflammatory (Aparna et al., 2012)
Phenol, 2-methyl- graphic file with name fx69.gif
(1S)-Propanol, (2S)-[(tert.butyloxycarbonyl)amino]-1-phenyl- graphic file with name fx70.gif Human Immunodeficiency virus -1 (HIV-1) Protease Inhibitors (Ghosh et al., 2015)
9-Octadecenoic acid (Z)-, methyl ester graphic file with name fx71.gif Lubricant (Faujdar and Singh, 2021)
Phytol graphic file with name fx72.gif Control Ganoderma boninense (Plant disease) (ABDUL AZIZ,)
Antioxidant, Anti-inflammatory (Islam et al., 2018)
9,12,15-Octadecatrienoic acid, (Z,Z,Z)- graphic file with name fx73.gif Reduce complications in Covid-19 patients. (Weill et al., 2020)
Neuroprotective Properties. (Blondeau et al., 2015)
Octadecanoic acid graphic file with name fx74.gif Play role in food reward (Li et al., 2020)
Lowers High density lipoprotein (HDL) cholesterol (van Rooijen et al., 2021)
4-Allyl-3-(dimethylhydrazono)-2-methylhexane-2,5-diol graphic file with name fx75.gif
Benzyl .beta.-d-glucoside graphic file with name fx76.gif
4,6-dimethyl-2-propyl-1,3,5-dithiazinane graphic file with name fx77.gif
1,3-Benzenediol, 2-methyl- graphic file with name fx78.gif
9-Octadecenamide, (Z)- graphic file with name fx79.gif Anti-depressive effects (Ge et al., 2015)
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3.3. Free radical scavenging efficacy of aqueous and Methanolic extracts of M. Oleifera leaves at varying concentrations:

The aqueous extract of Moringa leaves have the IC50 at concentration of 4.65 µl/ml after incubating for 30 min Fig. 3 whereas the IC50 of Methanolic extract was found 1.83 µl/ml Fig. 4 which is significantly lower than the IC50 of Moringa aqueous extract. Various concentrations (1 µl/ml to 5 µl/ml) of Moringa aqueous and Methanolic extracts were also evaluated and compared at the defined interval of incubation time up to 160 min to identify the maximum FRSP for each concentration and the results are showcased in Fig. 5.

Fig. 3.

Fig. 3

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IC50 of Moringa O. leaves aqueous extract.

Fig. 4.

Fig. 4

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IC50 of Moringa O. leaves Methanolic extract.

Fig. 5.

Fig. 5

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Free radical scavenging potency (FRSP) comparison of Aqueous and Methanolic extract of varying concentration at various incubation time points.

4. Discussion

This study is among the very few reports where the phytochemical profile of Moringa extracts with their free radical scavenging potency studies have been reported. In this study, higher number of phytochemicals in methanolic extract (Table 3) of Moringa extract in comparison to aqueous (Table 1) could be due to difference in their polarity, which could have led to difference in the extraction of phytochemicals. These, phytochemicals have various industrial applications and medicinal properties like anti-tumor, anti-cancer, Insulin regulation, anti-oxidant etc. which makes it really a magical plant for food, medicine and suitable natural ingredient to explore its further applications in diverse areas like in cosmetics, personal care products etc.

Natural antioxidants are always of very high importance for health as a part of food and as a part of cosmetics for topical applications to combat the detrimental affects of free radicals on internal and external organs like skin aging etc. Both aqueous and methanolic Moringa extracts have excellent anti-oxidant/FRSP. However, in relative terms Methanolic extract found to have lower IC50 (1.83 µl/ml) Fig. 4 reflecting higher free radical scavenging ability in comparison to of aqueous extract having higher IC50 (4.65 µl/ml) Fig. 3. This could be mainly due to higher number of polyphenolic component extracted in Methanolic extracts and relatively at higher percentages, which is contributing towards higher scavenging potency at lower concentration. It has been found that Methanolic extract at 5 µl/ml gives the 88.5% FRSP and does not change significantly over the period of time and reaches maximum level of 92.8% FRSP. Whereas aqueous extract at 5 µl/ml show 35.8% FRSP at the initial time point and which further scavenge the DPPH free radical significantly up to 68.4% in 160 min Fig. 6, however still less FRSP of Moringa Aqueous extract than the Methanolic extract could be due to the same reason as explained above of having more polyphenolic components in Methanolic extract of Moringa as reflected in GC-MS results.

Fig. 6.

Fig. 6

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Free radical scavenging potency (FRSP) comparison of Aqueous and Methanolic extract of 5 µl/ml concentration at various incubation time points.

5. Conclusions

This study has investigated the Moringa aqueous extract and identified twenty-five phytochemicals and similarly in Methanolic extract fifty-four phytochemical components were identified. The higher number of these constituents in methanol may be due to polarity difference, which contributed to solubilize the various molecules. Few of phytochemicals reported here are rarely detected in plant extracts like 3,3′-Iminobispropylamine, Butanedioic acid, 2-hydroxy-2-methyl- etc. and have potential applications. In further studies these extracts have shown substantial free radical scavenging potency, IC50 of Moringa aqueous extract observed is 4.65 µl/ml and for methanolic extract 1.83 µl/ml. Also, found that Methanolic extract at 5 µl gives the 88.5% FRSP at initial time point and does not change significantly over the period of time and reaches maximum level of 92.8% FRSP. Whereas aqueous extract at 5 µl show 35.8% FRSP at the initial time point and which further scavenge the DPPH free radical significantly up to 68.4% in 160 min. These high FRSP make them very suitable ingredients for various applications like food, animal feed medicines, cosmetic etc. We are in the process of establishing the same in products of topical application to have skin benefits like prevention of skin damage, aging etc.

Declaration of Competing Interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgments

Authors are highly thankful to IFFCO group, UAE, especially Mr. Isa Allana, Managing director (MD), Serhad C. Kelemci, Chief executive officer (CEO), Mr. Sunil Singh, Technical director and NIT-Warangal’s director for their encouragement and continuous support for this study.

Footnotes

Peer review under responsibility of King Saud University.

References

  1. Abbas A. A. Z., Abu-Mejdad N. M. J., Atwan W. Z., Al-Masoudi A. N., 2016. Synthesis and Biological Evaluation of New Dipyridylpteridines, Lumazines, and Related Analogues. J. Heterocyclic Chem., HTTPS://DOI.ORG/10.1002/jhet.2651.
  2. Syamimi D.A.A., 2019. Phytol-Containing Seaweed Extracts as Control for Ganoderma boninense. J.O.P.R. 31(2), 238-247. HTTPS://DOI.ORG/10.21894/jopr.2019.0018.
  3. Ageel A.M., Parmar N.S., Mossa J.S., Al-Yahya M.A., Al-Said M.S., Tariq M. Anti-inflammatory activity of some Saudi Arabian medicinal plants. Agents Actions. 1986;17(3-4):383–384. doi: 10.1007/BF01982656. [DOI] [PubMed] [Google Scholar]
  4. Al-Ziaydi A.G., Imran M., Al-Shammari A.M., Kadhim H.S., Jabir M., 2020. The anti-proliferative activity of D-Mannoheptulose against breast cancer cell line through glycolysis inhibition AIP Conference Proceedings 2307, 020023. HTTPS://DOI.ORG/ 10.1063/5.0032958.
  5. Aparna V., Vijayan D., Mandal P., Karthe P., 2012. Anti-Inflammatory Property of n-Hexadecanoic Acid: Structural Evidence and Kinetic Assessment. J. Chem. Bio. D. D. 80(3), 434-9. HTTPS://DOI.ORG/10.1111/j.1747-0285.2012.01418.x. [DOI] [PubMed]
  6. Bizzarri M., Laganà A.S., Aragona D., Unfer V., 2020. Inositol and pulmonary function. Could myo-inositol treatment downregulate inflammation and cytokine release syndrome in SARS-CoV-2? Eur. Rev. Med. Pharmacol. Sci. 24 (6): 3426-3432 HTTPS://DOI.ORG/10.26355/eurrev_202003_20715. [DOI] [PubMed]
  7. Blondeau, N., Lipsky, R.H., Bourourou, M., Duncan, M.W., Philip, 2015. Alpha-Linolenic Acid: An Omega-3 Fatty Acid with Neuroprotective Properties—Ready for Use in the Stroke Clinic? HTTPS://DOI.ORG/10.1155/2015/519830. [DOI] [PMC free article] [PubMed]
  8. Brown H. C., West Lafayette W., 2001. Economical and Convenient Procedures for The Synthesis of Catecholborane. Patent No.: US 6,204,405 B1.
  9. Cancelas J., Acitores A., Penacarrillo M.L.V., Malaisse W.J., Valverde I. Activation of glycogen synthase a in hepatocytes exposed to alpha-D-glucose pentaacetate. I. J. Mol. Med. 2000;6(2):197–199. doi: 10.3892/ijmm.6.2.197. HTTPS://DOI.ORG/10.3892/ijmm.6.2.197. [DOI] [PubMed] [Google Scholar]
  10. Čechovská L., Cejpek K., Konečný M., Velíšek J. On the role of 2,3-dihydro-3,5-dihydroxy-6-methyl-(4H)-pyran-4-one in antioxidant capacity of prunes. Eur. Food Res. Technol. 2011;233(3):367–376. [Google Scholar]
  11. Choi J.-K., Carreras I., Dedeoglu A., Jenkins B.G. Detection of increased scyllo-inositol in brain with magnetic resonance spectroscopy after dietary supplementation in Alzheimer’s disease mouse models. J. Neuropharm. 2010;59(4-5):353–357. doi: 10.1016/j.neuropharm.2010.03.011. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Courtois P., Sener A., Malaisse W.J. D-mannoheptulose phosphorylation by hexokinase isoenzymes. Int. J. Mol. Med. 2001;7:359–363. doi: 10.3892/ijmm.7.4.359. HTTPS://DOI.ORG/10.3892/ijmm.7.4.359. [DOI] [PubMed] [Google Scholar]
  13. Gertjan J.M., Den Hartog, Agnes Boots W., Aline Adam-Perrot, Fred Brouns, Inge W.C.M Verkooijen, Antje R.Weseler, Guido R.M.M Haenen, Aalt Bast, 2010 Erythritol is a sweet antioxidant. PubMed, Nutrition 26(4), 449-58. HTTPS://DOI.ORG/10.1016/j.nut.2009.05.004. pub 2009 Jul 24. [DOI] [PubMed]
  14. Faujdar E., Singh R.K. Methyl oleate derived multifunctional additive for polyol based lubricants. Wear. 2021;466-467:203550. doi: 10.1016/j.wear.2020.203550. [DOI] [Google Scholar]
  15. Freeman, S., Hudlicky, T., 2004. New oligomers of conduritol-F and muco-inositol. Synthesis and biological evaluation as glycosidase inhibitors. J. BMCL. 14(5).1209-12. HTTPS://DOI.ORG//10.1016/j.bmcl.2003.12.050. [DOI] [PubMed]
  16. Gamal E.E.G., Khalifa S.A.K., Gameel A.S., Emad M.A. Traditional medicinal plants indigenous to Al-Rass province, Saudi Arabia. J. Med. Plants Res. 2010;4(24):2680–2683. [Google Scholar]
  17. Ge, L., Zhu, M.M., Yang, J.Y., Wang, F., Zhang, R., Zhang, J.H., Shen, J., Tian, H.F., Wu, C.F., 2015. Differential proteomic analysis of the anti-depressive effects of oleamide in a rat chronic mild stress model of depression. J.PBB. vol.131, 77-86. HTTPS://DOI.ORG/10.1016/j.pbb.2015.01.017. [DOI] [PubMed]
  18. Ghosh, A..K, Yu, X., Osswald, H.L., Agniswamy, J., Wang, Y.F., Amano, M., Weber, I.T., Mitsuya, H., 2015. Structure-based design of potent HIV-1 protease inhibitors with modified P1-biphenyl ligands: synthesis, biological evaluation, and enzyme-inhibitor X-ray structural studies. J Med Chem. 2015 Jul 9;58(13):5334-43. HTTPS://DOI.ORG/10.1021/acs.jmedchem.5b00676. [DOI] [PMC free article] [PubMed]
  19. Hagiyama K., Suzuki K., Ohtake M., Shimada M., Nanbu N., Takehara M., Ue M., Sasaki Y. Physical properties of substituted 1,3-dioxolan-2-ones. Chem. Let. 2008;37(2):210–211. HTTPS://DOI.ORG/10.1246/cl.2008.210. [Google Scholar]
  20. Hamedi A., Lashgari A.P., Pasdaran A. 2019 Antimicrobial Activity and Analysis of the Essential Oils of Selected Endemic Edible Apiaceae Plants Root from Caspian Hyrcanian Region (North of Iran) Pharm Sci. 2019;25(2):138–144. HTTPS://DOI.ORG/10.15171/PS.2019.21. [Google Scholar]
  21. He Y., Johnson J. L. H., Yalkowsky S. H., 2005. Oral formulation of a novel antiviral agent, PG301029, in a mixture of Gelucire 44/14 and DMA (2:1, wt/wt). AAPS PharmSciTech 6, E1–E5 (2005). HTTPS://DOI.ORG/10.1208/pt060101. [DOI] [PMC free article] [PubMed]
  22. Huang, A., Neil Brody, Liebman Tracey N, 2017. Dihydroxyacetone and sunless tanning: knowledge, myths, and current understanding. J. of the A. Acad. of Dermat. Vol-77, I-5, 991-992. HTTPS://DOI.ORG/10.1016/j.jaad.2017.04.1117. [DOI] [PubMed]
  23. Imad H.H., Hussein J.H., Muhanned A.K., Nidaa S.H. Identification of five newly described bioactive chemical compounds in methanolic extract of Mentha viridis by using gas chromatography – mass spectrometry (GC-MS) J. Pharmacognosy Phytother. 2015;7(7):107–125. [Google Scholar]
  24. Islam M.T., Ali E.S., Uddin S.J., Shaw S., Islam M.A., Ahmed M.I., Chandra Shill M., Karmakar U.K., Yarla N.S., Khan I.N., Billah M.M., Pieczynska M.D., Zengin G., Malainer C., Nicoletti F., Gulei D., Berindan-Neagoe I., Apostolov A., Banach M., Yeung A.W.K., El-Demerdash A., Xiao J., Dey P., Yele S., Jóźwik A., Strzałkowska N., Marchewka J., Rengasamy K.R.R., Horbańczuk J., Kamal M.A., Mubarak M.S., Mishra S.K., Shilpi J.A., Atanasov A.G. Phytol: A review of biomedical activities. F. Chem. T. 2018;121:82–94. doi: 10.1016/j.fct.2018.08.032. [DOI] [PubMed] [Google Scholar]
  25. Kaiser A., Gottwald A., Wiersch C., 2001. Effect of drugs inhibiting spermidine biosynthesis and metabolism on the in vitro development of Plasmodium falciparum. Parasitol Res 87, 963–972 (2001). HTTPS://DOI.ORG/10.1007/s004360100460. [DOI] [PubMed]
  26. Zdravko, K., Antoaneta, T.G., 2020. Inositols in PCOS Molecules 25(23):5566 HTTPS://DOI.ORG/10.3390/molecules25235566.
  27. Kanhar S., Sahoo A.K. Ameliorative effect of Homalium zeylanicum against carbon tetrachloride-induced oxidative stress and liver injury in rats. J. biopha. 2018;111:305–314. doi: 10.1016/j.biopha.2018.12.045. HTTPS://DOI.ORG/10.1016/j.biopha.2018.12.045. [DOI] [PubMed] [Google Scholar]
  28. Khorassani R., Hettwer U., Ratzinger A., Steingrobe B., Karlovsky P., Claassen N. Citramalic acid and salicylic acid in sugar beetroot exudates solubilize soil phosphorus. BMC Plant Bio. 2011;11(1):121. doi: 10.1186/1471-2229-11-121. [DOI] [PMC free article] [PubMed] [Google Scholar]
  29. Leone A., Spada A., Battezzati A., Schiraldi A., Aristil J., Bertoli S. Cultivation, genetic, ethnopharmacology, phytochemistry and pharmacology of Moringa oleifera leaves: an overview. Int. J. Mol. Sci. 2015;16:12791–12835. doi: 10.3390/ijms160612791. HTTPS://DOI.ORG/10.3390/ijms160612791. [DOI] [PMC free article] [PubMed] [Google Scholar]
  30. Li, Y., Wu, H., Zhang, R., Shu, G., Wang, S., Gao, P., Zhu, X., Jiang, Q., Wang, L., 2020. Diet containing stearic acid increases food reward-related behaviors in mice compared with oleic acid. J.brainresbull.vol.164, 45-54. HTTPS://DOI.ORG/10.1016/j.brainresbull.2020.08.012. [DOI] [PubMed]
  31. Liu S., He L., Yao K. The antioxidative function of alpha-ketoglutarate and its applications. Bio Med R.I. 2018;2018:1–6. doi: 10.1155/2018/3408467. [DOI] [PMC free article] [PubMed] [Google Scholar]
  32. Manca M.L., Palomo S.M., Caddeo C., Nacher A., Sales O.D., Peris J.E., Pedraz J.L., Fadda A.M., Manconi M. Sorbitol-penetration enhancer containing vesicles loaded with baicalin for the protection and regeneration of skin injured by oxidative stress and UV radiation. J. ijpharm. 2018;555:175–183. doi: 10.1016/j.ijpharm.2018.11.053. HTTPS://DOI.ORG /10.1016/j.ijpharm.2018.11.053. [DOI] [PubMed] [Google Scholar]
  33. Mariano B., Gianfranco C. Inositol: history of an effective therapy for polycystic ovary syndrome. Eur. Rev. Med. Pharmacol. Sci. 2014;18:1896–1903. [PubMed] [Google Scholar]
  34. Markad, S.D., Kaur, P., Kishore Reddy, B.K. 2015. Novel lead generation of an anti-tuberculosis agent active against non-replicating mycobacteria: exploring hybridization of pyrazinamide with multiple fragments. Med Chem Res 24, 2986–2992 (2015). HTTPS://DOI.ORG/10.1007/s00044-015-1352-6.
  35. Nishio T., Yoshikawa Y., Shew C.Y., Umezawa N., Higuschi T., Yoshikawa K. Specific effects of antitumor active norspermidine on the structure and function of DNA. Sci. Rep. 2019;9:14971. doi: 10.1038/s41598-019-50943-1. HTTPS://DOI.ORG/10.1038/s41598-019-50943-1. [DOI] [PMC free article] [PubMed] [Google Scholar]
  36. Ölgena S., Altanlarb N., Karataylıc E., Bozdayıc M. Antimicrobial and antiviral screening of novel indole carboxamide and propanamide derivatives. Z. Naturforsch. 2008;63c:189–195. doi: 10.1515/znc-2008-3-405. [DOI] [PubMed] [Google Scholar]
  37. Paliwal P., Sargolzaei S., Bhardwaj K.S., Bhardwaj V., Dixit C., Kaushik A. Grand challenges in bio-nanotechnology to manage the COVID-19 pandemic. Front. Nanotechnol. 2020;2 HTTPS://DOI.ORG/10.3389/fnano.2020.571284. [Google Scholar]
  38. Paquette L.A., Crich D., Fuchs P.L., Molander G.A. Encyclopedia of reagents for organic synthesis. Wiley, New York. 2009;2:1017. [Google Scholar]
  39. Pintaudi B., Di Vieste G., Bonomo M. The Effectiveness of Myo-Inositol and D-Chiro Inositol Treatment in Type 2 Diabetes. I. J Endocrinology. 2016;2016:1–5. doi: 10.1155/2016/9132052. [DOI] [PMC free article] [PubMed] [Google Scholar]
  40. Purena R., Seth R., Bhatt R. Protective role of Emblica officinalis hydro-ethanolic leaf extract in cisplatin induced nephrotoxicity in Rats. Tox. Rep. 2018;5:270–277. doi: 10.1016/j.toxrep.2018.01.008. HTTPS://DOI.ORG/10.1016/j.toxrep.2018.01.008. [DOI] [PMC free article] [PubMed] [Google Scholar]
  41. Rhew, ZI., Lee, J.H. & Han, Y. 2020. Aster yomena has anti-arthritic activity against septic arthritis induced by Candida albicans: its terpenoid constituent is the most effective and has synergy with indomethacin. ADV TRADIT MED (ADTM) 20, 213–221 (2020). HTTPS://DOI.ORG/10.1007/s13596-019-00405-w.
  42. Rodriguez-Garay B., Phillips G.C., Kuehn G.D. Detection of norspermidine and norspermine in Medicago sativa L. (Alfalfa) Plant Physiol. 1989;89(2):525–529. doi: 10.1104/pp.89.2.525. [DOI] [PMC free article] [PubMed] [Google Scholar]
  43. Saeed N.M., Demerdashb E. E., Abdel-Rahmana H.M., Algandabyc M. M., Al-Abbasid F. A., Abdel-Naim A. B., 2012. Anti-inflammatory activity of methyl palmitate and ethyl palmitate in different experimental rat models.J. TAAP. 264(1), 84-93. HTTPS://DOI.ORG/10.1016/j.taap.2012.07.020. [DOI] [PubMed]
  44. Sagiv A.E., Dikstein S., Ingber A., 2001 Feb. The efficiency of humectants as skin moisturizers in the presence of oil. PubMed, S.R&T, 7(1), 32-5. HTTPS://DOI.ORG/10.1034/j.1600-0846.2001.007001032.x. [DOI] [PubMed]
  45. Scruel, O., Vanhoutte, C., Sener, A., 1998. Interference of D-mannoheptulose with D-glucose phosphorylation, metabolism and functional effects: Comparison between liver, parotid cells and pancreatic islets. Mol Cell Biochem 187, 113–120 (1998). HTTPS://DOI.ORG/10.1023/A:1006812300200. [DOI] [PubMed]
  46. Shendurse A.M., Khedkar C.D. Encyclopedia of Food and Health. Elsevier; 2016. pp. 239–247. [DOI] [Google Scholar]
  47. Siddiqui N., Azad B., Alam M.S., Ali R. Indoles: role in diverse biological activities. IJPCR. 2010;2(4):121–127. [Google Scholar]
  48. Skoweranda J., Bukowska-Strzyzewska M., Bartnik R., Strzyżewski W. Molecular structure and some reactivity aspects of 2,6-diamino-4(3H)-pyrimidinone monohydrate. J. Chem. Cryst. 1990;20(2):117–121. [Google Scholar]
  49. Starostin K.E., Lapitskaya A.M., Ignatenko V.A., Pivnitsky K.K., Nikishin L.G. Practical synthesis of hex-5-ynoic acid from cyelohexanone. Russ. Chem. Bull. 2000;49:81–84. [Google Scholar]
  50. Sunkara S.P., Zwolshen H.J., Prakash J.N., Bowlin L.T. Progress in Polyamine Research. Plenum Press; New York: 1988. Mechanism of Antitumor activity of Norspermidine, a structural homologue of Spermidine; pp. 707–716. [DOI] [PubMed] [Google Scholar]
  51. Takebe Y., Iuchi K., Tsukamoto G., 1984. 4-Chloro-4-Methyl-5-Methylene-1,3-Dioxolan-2-One. Patent EP0147472 B1.
  52. Ullah R., Alqahtani S.A., Noman M.A.O., Alqahtani M.A., Ibenmoussa S., Bourhia M. A review on ethno-medicinal plants used in traditional medicine in the Kindgdom of Saudi Arabia. S. J. Bio. Sci. 2020;27:2706–2718. doi: 10.1016/j.sjbs.2020.06.020. HTTPS://DOI.ORG/10.1016/j.sjbs.2020.06.020. [DOI] [PMC free article] [PubMed] [Google Scholar]
  53. Rooijen, M.A.V, Plat, J., Blom, W.A.M., Zock, P.L. Mensink, R.P., 2020. Dietary stearic acid and palmitic acid do not differently affect ABCA1-mediated cholesterol efflux capacity in healthy men and postmenopausal women: A randomized controlled trial. HTTPS://DOI.ORG/10.1016/j.clnu.2020.08.016. [DOI] [PubMed]
  54. Varahachalam S.P., Lahooti B., Chamaneh M., Bagchi S., Chhibber T., Morris K., Bolanos F.J., Kim Y.N., Kaushik A. Nanomedicine for the SARS-CoV-2: state-of-the- art and future prospects. Int. J. Nanomed. 2021;16:539–560. doi: 10.2147/IJN.S283686. HTTPS://DOI.ORG/10.2147/IJN.S283686. [DOI] [PMC free article] [PubMed] [Google Scholar]
  55. Weill P., Plissonneau C., Legrand P., Rioux V., Thibault R. May omega-3 fatty acid dietary supplementation help reduce severe complications in Covid-19 patients? J. Biochi. 2020;179:275–280. doi: 10.1016/j.biochi.2020.09.003. HTTPS://DOI.ORG/10.1016/j.biochi.2020.09.003. [DOI] [PMC free article] [PubMed] [Google Scholar]
  56. Arne N., Wick, Mary C., Almen, Lionel Joseph., 2016. The Metabolism of Sorbitol., jps. Volume 40, Issue 11, November 1951, Pages 542-544. HTTPS://DOI.ORG10.1002/jps.3030401104. [DOI] [PubMed]
  57. Yu X., Zhao M., Liu F., Zeng S., Hu J. Identification of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one as a strong antioxidant in glucose–histidine Maillard reaction products. Food res. Int. 2013;51(1):397–403. [Google Scholar]
  58. Zaitseva, N.V., Ulanova, T.S., Dolgikh, O.V., 2018. Diagnostics of Early Changes in the Immune System Due to Low Concentration of N-Nitrosamines in the Blood. Bull Exp Biol Med 164, 334–338 (2018). HTTPS://DOI.ORG/10.1007/s10517-018-3984-2. [DOI] [PubMed]
  59. Zelikin A.N., Putnam D. Poly(carbonate-acetal)s from the dimer form of dihydroxyacetone. Macromolecules. 2005;38(13):5532–5537. [Google Scholar]

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