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OBTAINING COLLOID COMPOSITIONS BASED ON PEGANUM HARMALA
EXTRACTS AND NANOSILVER
F. F. Hoshimov,
O. K. Ergashev,
M.F. Orifboeva-Fayzullaeva.
Namangan State Technical University, Uzbekistan
A.A. Rakhmonov
Namangan State University, Uzbekistan
Abstract:
The article provides information on the compounds contained in the Peganum harmala
plant, the use of plant parts and individual compounds. The sum of extractive substances was
isolated and their yields were determined by extracting different parts of the Peganum harmala
plant with water. Nanosilver compositions of the extracts were prepared and their IR spectra
were obtained.
Keywords:
Peganum harmala, harmaline, harmine, harmalol, peganin, extraction, nanosilver,
reducing agent, stabilizer, composition, IR spectrum, yield.
Introduction.
Peganum harmala is rich in resources, widely distributed in the world, and has a
medicinal history of over 2000 years. Traditional use in disinfectants and mosquito control has
led to its successful application in the treatment and prevention of diseases in humans, animals,
and plants. The plant Peganum harmala, popularly known as Peganum harmala, contains a large
number of biologically active substances, especially alkaloids. Peganum harmala alkaloids are
also psychoactive compounds in humans. Plant extracts have insecticidal properties against pests
of agricultural plants. Infectious diseases cause great harm to the health of humans, animals, and
plants, and they occur worldwide due to the diversity of pathogens and their high infectivity.
Effective prevention and treatment of infectious diseases are major medical problems.
Antimicrobial drugs play an important role in the prevention and treatment of infectious diseases
[1, 2].
Despite the continuous development and progress in medical science, many pathogens have
developed drug resistance to antimicrobial drugs due to genetic changes, reducing the
effectiveness of antibiotics and greatly limiting their clinical application. In addition, the
development of antibiotics has almost come to a standstill in the past decade due to the long
R&D cycles of antibiotics, high R&D costs and low commercial profits [3]. Therefore, there is
an urgent need for new antimicrobial drugs to eliminate diseases caused by drug-resistant
microorganisms. P. harmala L. - belongs to the family Zygophyllaceae (in some sources
Nitrariaceae). In Uzbekistan, it is called "isiriq" and is a plant that has been used for various
purposes since ancient times. P. harmala is a plant distributed mainly in the Middle East, North
Africa and Central Asia. The plant is usually not grazed by animals due to its bitter taste.
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Figure 1. Peganum harmala L.: a) leaf, b) flower, c) fruit, d) seed.
P. harmala is a perennial herb with a strong odor, blooming in May-July, growing in steppes and
hills, 40-70 cm high. The root is multi-headed, woody, thick, 3-5 cm in diameter. The stem is
branched, bare, densely leafy. The leaves are alternate, 4-5 cm long, 5-6 cm wide, three-edged at
the base, and the segments are also divided into linear segments. The flowers are white, the fruit
is a three-celled capsule with a diameter of 0.6-1 cm, the fruits ripen from late June to August, 1-
2 mm long (Figure 1).
In recent years, many studies have shown that more and more natural products of plants have
special biological activities as natural antibiotics, which play an important role in the prevention,
treatment and reduction of the spread of disease. Peganum harmala L., a perennial plant
belonging to the Zygophyllaceae family. Phytochemical studies have shown that the main
chemical components in the plant are alkaloids, flavonoids, esters and trace elements [4-7].
However, there are few studies on the production and practical application of nanosilver-
containing alkaloid extracts, and the content is limited to the synthesis of nanosilver using the
extract using the “Green” method. Based on this, we aimed to obtain a drug with bactericidal and
fungicidal properties from the extract of the Peganum harmala plant containing nanosilver.
Literature review.
The pharmacological, chemical and biological activity of Peganum harmala
has been studied for more than 100 years. Peganum harmala contains a wide variety of
compounds. More than 308 compounds have been isolated from Peganum harmala, of which 97
are alkaloids, 24 are flavonoids, 10 are triterpenoids, 3 are anthraquinones, 2 are
phenylpropanoids, 18 are carbohydrates, 17 are amino acids, 99 are volatile oils, 26 are fatty
acids, 26 are linoleic acids, 3 are carotenes, and 6 other trace elements. Among these compounds,
the highest content is the β-carboline alkaloids (βC). The alkaloid content is up to 10% in the
seeds, followed by the roots, and the lowest in the leaves. Their main compounds include
harmine, harmaline, harmalol, harman, and harmol; several new compounds have been reported
in recent years (Table 1) [8].
Table 1.
Formula and structure of the most abundant alkaloids of Peganum harmala
Name
Formula
IUPAC name
Structure
C
13
H
12
N
2
O 7-Methoxy-1-methyl-9H-
pyrido[3,4-b]indole
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C
13
H
14
N
2
O 4,9-dihydro-7-methoxy-1-methyl-
3H-pyrido[3,4-b]indole
Tetragidrogarmin C
13
H
16
N
2
O 7-Methoxy-1,2,3,4-tetrahydro-
garmine
C
12
H
10
N
2
1-methyl-9H-β-carboline
There are a large number of alkaloids, quinazoline and indole derivatives. Of the total number of
alkaloids, harmaline, harmine (banisterine), harmalol and L-peganine (vazizine) were isolated for
the first time in pure form, while pegamine, peganol, deoxypeganine, peganidin and others were
isolated in recent years. It is known that 50% of the total amount of alkaloids in the seeds is
harmine, pregamines, harminates, and up to 78% of the total amount of alkaloids in the grass is
peganine. It has also been found that young roots contain twice as many alkaloids as old ones,
with harmine prevailing. As the above-ground part of the plant develops, the amount of alkaloids
and the proportion of peganine in it decreases, while the amount of harmine increases. The
qualitative composition of alkaloids largely depends on the place where the plant grows. In
addition to alkaloids, red dye and drying oily oil are isolated from the seeds of the plant. The
herb contains protein (24%), fatty oil (4%) and extractives (31%). The raw material is used to
obtain the drug deoxypeganine hydrochloride, which has anticholinesterase activity. The drug is
used for lesions of the peripheral nervous system.
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Figure 2. Structures of the last 20 new compounds isolated from Peganum harmala.
In addition to the above, other alkaloids such as harminic acid (methyl 7-methoxy-β-carboline-1-
carboxylate),
harmalic
acid
(7-methoxy-3,4-dihydro-β-carboline-1-carboxylic
acid),
harmanamide (1-carbamoyl-7-methoxy-β-carboline), and acetylnorgarnine (1-acetyl-7-methoxy-
β-carboline) are also found in large quantities. The latest novel compounds from Peganum
harmala have been named as follows: (−)-pegarmalin A (1), (+)-pegarmalin A (2), pegaharmines
F–K (3–8), (S)- and (R)-1-(2-aminobenzyl)-3-hydroxypyrrolidin-2-one β-D-glucopyranosyl-
(1→6)-β-D-glucopyranoside (9, 10), (S)- and (R)-vasicinone β-D-glucopyranosyl-(1→6)-β-D-
glucopyranoside (11, 12), N-[3-(2-amino-4-methoxyphenyl)-3-oxopropyl] acetamide (14),
pegagarines A–F (15–20) (Figure 2)[9].
The various compounds are the material basis for its broad-spectrum antimicrobial activity. Due
to the diversity of secondary metabolites of Peganum harmala and the development of
technology, new compounds have been discovered from plant extracts. The antimicrobial
activity of these new compounds has been poorly studied. The antibacterial effect of Peganum
harmala has been demonstrated in many gram-positive and gram-negative bacteria. It has also
been found that seed and root extracts have a synergistic effect when used together with drugs
such as neomycin, colistin and carbenicillin. In conclusion, it has been shown that the harmine
alkaloid can be used in the development of drugs for the treatment of infectious diseases [10-12].
Smoke from Peganum harmala seeds can act as an air disinfectant to reduce the concentration of
bacteria in the air [40]. In residential areas, the rate of destruction of airborne bacteria after 5 g of
seeds was as high as 71.4%, with smoke generation for 5 minutes. In an educational setting, the
elimination rate of airborne bacteria after 10 minutes of fumigation from 10 g of seeds reached
92.8% [13].
Peganum harmala has been shown to have fungicidal effects on various pathogenic fungi. As can
be seen from the current studies, there are many fungicidal studies on Peganum harmala, which
show good fungicidal activity of Peganum harmala. The active component is mainly the extract
of the seeds. However, studies on screening fungicidal compounds and optimizing the structure
of highly antibacterial compounds are rare. It is an urgent need to identify the active compounds
and optimize the lead compounds in future studies [14, 15].
The inhibitory effects of Peganum harmala on various animal viruses and plant viruses have been
reported. Current studies have reported the antiviral activity of various components of Peganum
harmala. Most of these studies have only reported on the antiviral effects of Peganum harmala
extracts, but studies on screening for antiviral compounds in extracts are rare, and studies on the
antiviral mechanism of Peganum harmala are even less. Therefore, more research is still needed
in these aspects [16-18].
Peganum harmala has been shown to have significant antiparasitic and acaricidal activities. At
present, Peganum harmala seed extract has good inhibitory effects on pathogens. Therefore,
further studies using modern molecular biology and other tools are needed [19-21].
The inhibitory activity of Peganum harmala against a wide range of microorganisms may
account for its therapeutic effects on many pathogen-related diseases, such as wound healing,
skin inflammation, hemorrhoids, and cough. Peganum harmala is a potential source for the
prevention or treatment of infectious diseases of plants such as rust and wilt due to its
insecticidal effect and inhibition of the activity of various plant pathogens [22, 23]. Peganum
harmala has antibacterial, anti-inflammatory, anti-leukemia and psoriasis effects, and has many
clinical pharmacological effects such as memory enhancement, and is clinically used to treat
cough, hypertension, diabetes, jaundice, colic, malaria, Alzheimer's disease and other diseases.
Reports on the bactericidal, fungicidal, antiviral and antiparasitic effects of Peganum harmala are
increasing year by year. However, the antifungal and antimicrobial effects and mechanisms of
Peganum harmala have not been described in detail.
The isolation of these substances and the development of biologically active systems based on
them are of great importance in the fields of medicine, agriculture and nanotechnology. In
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particular, colloidal systems enriched with nanosilver particles are widely used due to their
antibacterial and antioxidant properties. In this regard, this work is devoted to the isolation of
extracts from various parts of the Peganum harmala plant and the synthesis of colloidal systems
containing nanosilver based on these extracts.
Methods.
The plant was harvested and dried in June-July. Extractions from plant parts were
carried out at a temperature of 60oC, in acidic and neutral media, in a mass ratio of raw
material:solvent = 1:10. Nanosilver synthesis was carried out chemically, in the presence of
AgNO3 reducing agents sodium citrate and glucose. Distilled water was used as a solvent in all
reactions. The IR spectra of the samples were obtained on a Shimadzu FTIR spectrophotometer.
Results and analysis.
Isolation of alkaloids from different parts of the Peganum harmala plant -
leaves, stems, seeds and seed coat - by acetic acid extraction method, determination of the mass
yield of substances in each part, synthesis of nanosilver and synthesis of nanosilver-containing
compositions and study of IR spectra. Preparation of the plant for extraction. The dried Peganum
harmala plant was separated into structural vegetative parts - leaves, stems, seeds and seed coat.
The structural parts were ground separately to a size of 1 mm (Figure 3).
Figure 3. Scheme of separation of raw materials into components.
The extraction process was carried out as follows. For extraction, 10 grams of samples were
taken from each component and placed in 4 numbered beakers. 50 ml of 1% acetic acid solution
was poured onto each sample and the extraction process was carried out with constant stirring
using a magnetic stirrer for 30 minutes at a temperature of 60°C. After the specified time, the
mixtures were filtered, the filtrate and residue were separated. The above process was repeated
twice more with the residue. All the filtrates obtained were combined and concentrated, and the
extracts were finally filtered through blue ribbon filter paper. The colors of the obtained extracts
were different. The extract obtained from Peganum harmala leaves was dark brown, the extract
from seeds was brown, the extract from stems was light yellow, and the extract from seed coat
was cloudy yellow (Figure 4).
Figure 4. Scheme of extracting Peganum harmala at 60
o
C temperature (
extraction time
-
30
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minutes, extraction - 3 times, raw material:extractant = 1:5 mass ratio).
Determination of extraction yield. In order to determine the extraction yield, 10 ml of each
extract was weighed on an analytical balance to the nearest 4 decimal places. Then, it was dried
in a drying cabinet at 100°C until constant mass was reached, and the dry residue was reweighed
on an analytical balance under the above conditions. Dry mass and yield were calculated as a
percentage (Table 2). The total volume of extracts and the yield in terms of dry matter were
calculated using the following formula:
C
%=
m
1
m
2
∗100%
Where:
m
1
is the mass of the dry residue,
m
2
is the mass of the extract.
Table 2.
Yield of extract sums from parts of the Peganum harmala plant
№ Sample
Extract volume, ml
Dry residue, g
Yield, %
1
Leaf
75
0.65
6.5%
2
Stem
90
1.60
16%
3
Seed
98
1.10
11%
4
Seed husk
90
0,32
3,2%
These are the sum of extractive compounds. It is known from the literature that the Peganum
harmala plant contains extractive groups of natural compounds - salts of inorganic and organic
substances, alkaloids, proteins, carbohydrates, amino acids, water-soluble vitamins, hydrolyzable
tannins, glycosidated forms of flavonoids, coumarins.
In the second stage of experiments, experiments were carried out to obtain a colloidal solution
containing nanosilver based on the sum of Peganum harmala extracts. AgNO
3
was used as a
source of silver nanoparticles (AgNP), sodium citrate and glucose as reducing agents, polyvinyl
alcohol (PVA) and carboxylmethylcellulose sodium salt (CMS-Na) as stabilizers.
Biostimulant nanosilver is widely used in agriculture to increase crop yield and protect plants. It
can be used for pre-sowing seed treatment, soil cultivation, foliar spraying and plant nutrition.
Nanosilver-containing biostimulants promote nutrient absorption, activate physiological
processes in plants, and increase resistance to stress and diseases. Studies conducted by scientists
show the effectiveness of using nanosilver-containing biostimulants in various crops and their
effect on yield. Nanosilver-containing biostimulants are a promising method for increasing crop
yield and protecting plants in agriculture. Methods for obtaining, properties, and applications of
nanosilver-containing biostimulants have been studied in a number of studies, which allows them
to be used to improve agricultural production. To prepare the AgNP system in a “green” way, as
described in the literature, a 0.1 M solution of AgNO
3
was added directly to the Peganum
harmala extract. However, turbidity was observed immediately after the AgNO
3
solution was
added to the extract. In this case, as in the case of tobacco extract, the extract became turbid [24-
27].
This once again confirmed that some compounds in the extracts containing alkaloids react with
Ag+ ions and form a precipitate.
In subsequent experiments, work was carried out to obtain a stable colloidal system containing
AgNP with bactericidal properties by first preparing a colloidal solution of AgNP and then
adding it to a solution of Peganum harmala.
For this, silver nitrate was used as a source of AgNP, sodium citrate as reducing agents in
reaction 1, glucose in reaction 2, and polyvinyl alcohol as a stabilizer. The required
stoichiometric amounts of reagents were calculated and dissolved in distilled water. The optimal
conditions for obtaining nanosilver were found by changing the reaction time, stirring intensity,
concentration of reagents and stabilizers. The reactions were carried out at room temperature,
adding an equal volume of reducing solutions to the solution of the stabilizer and silver nitrate
mixture, and constantly stirring the solutions.
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Reaction 1: 12AgNO
3
+ 4Na
3
C
6
H
5
O
7
+ 6H
2
O → 12 Ag↓ + 12NaNO
3
+ 4C
6
H
8
O
7
+ 3O
2
Reaction 2:
2AgNO
3
+ C
6
H
12
O
6
+ NaOH→ 2Ag↓ + C
6
H
12
O
7
+ NaNO
3
Initially, solutions were prepared at 20°C. Then, a silver nitrate solution with a concentration of
500 mg/ml was prepared. Nanosilver samples were prepared by mixing the stabilizer and silver
nitrate solutions and adding an equal volume of reducing solution to the resulting mixtures with
constant stirring. For example, to obtain nanosilver of the desired size, 20 ml of an aqueous
solution of sodium citrate (0.1 M) was slowly added to a mixture of 20 ml of PVA (2.04%) and
silver nitrate (0.0463 M) to initiate a reaction between the solutions. The reaction of the solution
with Ag
+
ions was carried out for 5 minutes at 20°C with constant stirring. The color change of
the solution provides visual information about the completion of the reaction, as well as the
formation of a colloidal solution of nanosilver (Table 3).
Table 3
Nanosilver composites obtained by reducing AgNO
3
in the presence of various reducing
agents and polyvinyl alcohol (20°C).
The IR spectrum of Peganum harmala leaf extract revealed the following information. The
absorption region around 3309 cm⁻¹ is a characteristic broad peak associated with the stretching
vibrations of the ـOH or 0NH groups corresponding to hydrogen bonds or amine groups. These
peaks indicate the presence of phenolic and alkaloid compounds. The region 3000-2800 cm⁻¹ is a
characteristic peak corresponding to the -CH and -NH groups. This indicates the presence of
harmine and harmine-like alkaloids. The absorption region around 2378 cm⁻¹ and 2308 cm⁻¹ are
peaks associated with the asymmetric vibrations of carbonyl or carboxyl groups. The absorption
at 1636 cm⁻¹ is characteristic of the vibrations of carbonyl (C=O) or amide groups.
№ Reducing
agents
Change
Photo
1
Glucose
After 24 hours, the solution turned light
brown and remained transparent.
2
Sodium citrate After 24 hours, the solution turned gray-
black and became cloudy.
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Figure 5. IR spectrum of Peganum harmala leaf extract.
The absorption region around 1396 cm⁻¹ is due to stretching vibrations of N-O or C-N groups.
The absorptions around 1137 cm⁻¹ and 1010 cm⁻¹ are due to vibrations of the CO group, which
are characteristic of ether or glycoside structures. This indicates the presence of carbohydrates or
other compounds containing oxygen. The peaks in the absorption region 635-411 cm⁻¹ are due to
deformation vibrations of various bonds of the aromatic ring (Figure 5).
Figure 6. IR spectrum of Peganum harmala leaf extract containing nanosilver.
The IR spectrum of Peganum harmala leaf extract containing nanosilver showed the following:
the absorptions around 3295 cm⁻¹ differ from the previous spectrum by shifting to the higher
frequency region. This broad peak indicates the presence of -OH or -NH groups, which indicates
the presence of phenols, phenolic glycosides, amines and hydrogen bonds. The absorption region
at 2378–2311 cm⁻¹ is almost the same as the previous spectrum and is associated with carbonyl
groups. The region around 1636 cm⁻¹ is characteristic of the C=O stretching vibrations of
carbonyl groups in amides or carbonyl compounds of aromatic systems. The region around 1559
cm⁻¹ indicates the deformation vibrations of the C-H, N-H groups of aromatic compounds and is
characteristic of phenolic and aromatic amines present in the extract. The absorption regions at
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1218 and 1043 cm⁻¹ shifted to higher frequencies compared to the previous spectrum. They are
associated with C-O or C-N groups characteristic of esters and glycosides present in the extract.
The absorption region at 447 cm⁻¹ also shifted to higher frequencies by 36 cm⁻¹ compared to the
previous spectrum. This low-frequency vibration indicates the presence of silver complexes or
silver nanoparticles (Figure 6).
Conclusion:
The yield of extract sums from different parts of Peganum harmala plant ranged
from a minimum of 3% in the seed coat to a maximum of 16% in the stem. It was impossible to
obtain the sums of nanosilver-containing extracts by directly treating the extracts with AgNO
3
,
because the extract became cloudy and precipitates formed when AgNO
3
solution was added.
Then, colloidal solutions containing nanosilver were synthesized in the presence of reducing
agents glucose and sodium citrate, and polyvinyl alcohol was used as a stabilizer. A composition
with bactericidal-fungicidal properties was obtained by combining the extracts of the plant and
the colloidal solutions containing nanosilver. The IR spectra of the obtained extracts showed that
the extracts contained groups characteristic of alkaloids, carbohydrates, aromatic compounds,
and absorption frequencies characteristic of nanosilver.
The development of broad-spectrum insecticide, fungicide, and antimicrobial drugs based on the
compounds contained in Peganum harmala is an important research direction, and the research
conducted is an attempt in this direction. These results indicate the bright prospects of Peganum
harmala as a natural source of next-generation drugs, and also serve to further elucidate its
therapeutic mechanisms. Field tests are planned to study the insecticidal, fungicidal, and
biostimulatory properties of the obtained compositions.
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