INTRODUCTION:

The flora of Kazakhstan has approximately 5850 species of plants, including cultivated and imported plants.

Most (85%) are herbaceous plants, and more than 730 species are endemic, of which 175 species are vegetation of steppe regions, 250 species are desert and semidesert zones, and 600 species are rare and endangered. More than 1000 types are used in folk medicine^1-3. The first lists, including plants of Central Kazakhstan, were described in Lessing's works. They were compiled during his travels in 1834 and included approximately twenty plants (Christian Friedrich Lessing (1809-1862) Beitrag zur Flora des südlichen Urals un des Steppen. Linnaea, XI, 1835, 145-213)^4-6. The genus Scabiosa, according to some sources, represents approximately 80 species in the world, while others represent approximately 100 species. There are six species of this genus in Jordan, and 16 in Russia^7-8. There are 6 species of the genus Scabiosa growing in Kazakhstan, two of which are pale yellow scabiosa and iset scabiosa in Central Kazakhstan. We obtained subcritical carbon dioxide extracts from Lomelosia isetensis (L.) Soják, Scabiosa ochroleuca L. and Dipsacus strigosus Willd^9-12. According to Plants of the World (WFO) and the World Checklist of Vascular Plants (WCVP) online database the genera Dipsacus and Scabiosa and Lomelosia Raf. currently belong to the Caprifoliaceae Juss. family (honeysuckle family). The genera Dipsacus and Scabiosa were previously classified taxonomically in the Dipsaceae. The Caprifoliaceae Juss. family includes 33 accepted genera. The genus Dipsacus includes 21 recognized species, the genus Scabiosa 68 recognized species and Lomelosia Raf. includes 63 recognized species^13-14.

The optimal parameters with the maximum extract yield were as follows: pressure - 6,991-7, 295 106 Pa (69-72 atm); temperature -18-21^oC and extraction time -18-20 h¹⁵. The total yield was 0.57% for iset scabiosa, 0.46% for pale yellow scabiosa, and 1% for yellow-flowered teasel in terms of air–dry raw materials. The study of carbon dioxide extracts using chromatography-mass spectrometric analysis allowed us to establish that α-santonin is one of the main components of the three CO₂-extracts^16-17. The biological activity of carbon dioxide extracts, shown in vitro studies and their nontoxicity reveal the prospects of subcritical carbon dioxide extraction in production.

Our early studies on the stability of carbon dioxide extracts of iset scabiosa and scabiosa pale yellow to elevated temperatures established a temperature range from the beginning of destruction to complete burnout of samples corresponding to 52-369^oC, which indicates the possibility of storing carbon dioxide extracts of iset scabiosa and scabiosa pale yellow under normal conditions¹⁸. Researchers have also found that compounds containing exocyclic methylene group conjugated with lactone carbonyl group have pronounced antiprotozoal activity¹⁹. In studies on greenhouse plants (cucumbers), carbon dioxide extract of scabiosa pale yellow has shown high fungicidal activity against the putrefactive bacterium Bac. cellulosae hydrogenicus and Pythium debaryanum, which destroy the root system of cucumbers.

The sesquiterpene lactone, α-santonin, was previously isolated from Artemisia cina Berg, ex Poljak.and it was used as an anthelmintic drug^20-22. Artemisia cina Berg, ex Poljak. has been included in the Red Book of the USSR since 1978 and currently has the following status: "A species with declining numbers"²³. α-Santonin has been found in plants of the Asteraceae family: Inuba helenium, Artemisia L., Artemisia lercheana Weber ex Stechm., Artemisia santonica L. f. citralifera N. Rubtz, Artemisia spicigera C.Koch., Artemisia szovitsiana (Bess.) A.Grossh., Artemisia maritima L., Artemisia kurramensis Qazilb, Artemisia szovitsiana (Bess.) A.Grossh., Artemisia sogdiana Bunge, Artemisia campestris (var. Marschalliana) Spreng, Artemisia compacta Fisch^24-26, and a plant of the Apiaceae family Ferula L., Ferulago setifolia C.Koch^27-28.

MATERIALS AND METHODS:

The work was carried out at the School of Pharmacy of the "Medical University of Karaganda» Noncommercial Joint-Stock Company («MUK» NCJSC).

Determination of IR-spectra was carried out at the Department Physical and Analytical Chemistry of the Academician E.A. Buketov Karaganda State University.

The aboveground parts of scabiosa pale yellow (Scabiosa ochroleuca L.) were harvested in 2016, July, during the full flowering phase, in the territory of the village of Kerney in the Bukhar-Zhyrau district (Kazakhstan, Karaganda region).

Aboveground parts of iset scabiosa (Scabiosa isetensis L.) collected in the mountains of Ulytau (Kazakhstan, Karaganda region), during the flowering–fruiting phase, from July-August 2016.

Grass Dipsacus strigosus Willd, manufacturer: "Marislavna", Individual Entrepreneur Veselova Maria Vyacheslavovna, TU 9 197 – 004 - 01771 88917 – 2013, manufactured in September 2015, assembled and harvested in Krasnodar Krai, Republic of Adygea.

Carbon dioxide extracts obtained from the herb scabiosa pale yellow, iset scabiosa and yellow-flowered teasel (Dipsacus strigosus Willd)¹⁶

Alcohol and an aqueous extracts from CO₂-meal (waste from the production of carbon dioxide extract) of Scabiosa ochroleuca L.

Comparison preparations:

Collection material of the herbarium of the Faculty of Biology and Geography of the Karaganda State University named after academician E. A. Buketov. The herbarium code of Scabiosa isetensis L. - 2013.07.2014 (Col.: Buiratau Mountains); Scabiosa ochroleuca L. - 2010.06.11.01.14 (Col.: Karkaraly Mountains).

The working standard (WS) sample was α-santonin. C₁₅H₁₈O₃. CAS 481-06-1. 10mg. Analytical standard. Powder or crystals of colorless or white color. Melting point. = 172-173 ^oC. HPLC ≥ 95%, humidity ≤ 5%. The manufacturer is Sigma-Aldrich GmbH (Germany). Official dealer: LLP "LaborFarma", Almaty.

Reagents:

In experimental studies, chemical reagents and solvents of the qualification of especially pure, chemically pure, pure were used for the analysis.

Acetonitrile. C₂H₃N. CAS 75-05-8. (State Pharmacopoeia of the Republic of Kazakhstan vol. 1, p. 339).

Distilled water. CAS 7732-18-5. (State Pharmacopoeia of the Republic of Kazakhstan, vol. 1, p. 347).

Chloroform. CHCl₃. CAS 67-66-3. (State Pharmacopoeia of the Republic of Kazakhstan vol. 1, p. 440).

Ethanol (96%). C₂N₆O. CAS 64-17-5]. (State Pharmacopoeia of the Republic of Kazakhstan vol. 2, p. 581).

Methods:

1.1 GC/MS analysis

1.2 IR spectroscopy:

IR spectra were recorded on an FSM 1201 infrared Fourier spectrometer in tablets with potassium bromide, in the range from 4000 cm^-1 to 500 cm^-1.

1.2 UV spectrophotometry:

UV spectra were taken on an Agilent Cary 60 UV-Vis instrument, in the range from 190 to 400nm.

1.3 HPLC analysis:

The analysis of the studied samples was carried out by reverse-phase HPLC on the Agilent 1260 Infinity device in isocratic mode under the following conditions:

· Analytical column filled with sorbent Zorbax SB-C18, 4.6 x 150mm, with a particle size of 5 microns;

· Composition of the mobile phase: acetonitrile – water in a ratio of 2:3;

· Detection at a wavelength of 240nm, 254nm;

· Column temperature – 18-20^oC;

· The speed of the mobile phase is 0.500ml/min;

· The volume of the injected sample is 10µl.

The test to verify the suitability of the chromatographic system was carried out according to the methodology of the State Pharmacopoeia XI, vol. 1, 2.2.29, p.110.

Processing of the results was performed using Agilent Lab Advisor software.

Experimental:

Alcohol and aqueous extracts from carbon dioxide extraction waste were obtained by infusion in 70% ethyl alcohol and distilled water. Then, 350g of air-dried mass was placed in a stainless steel container, 70% ethyl alcohol was added, and the mixture was allowed to infuse for 3 days. The extract was filtered and concentrated using an IKARV 10 Digital rotary evaporator at 40-45^oC, based on the Research Institute "New Materials", KarSTU.

2.1 GC/MS analysis.

The following procedure was used to process the extracts: 10ml of ethanol was added to the sample and placed in a freezer at -20°C for 1hour. The extract was filtered from lipophilic ballast substances to paper filter at normal pressure. The obtained samples were diluted in 1:5 ethyl alcohol and injected into a gas chromatograph for qualitative and quantitative determination of components.

GC/MS analysis of CO₂-extract used conditions corresponding to previously published materials were used^16-17.

2.2 IR spectroscopy:

In the study of carbon dioxide extracts by IR spectroscopy in disks with potassium bromide, peak density ranged from 4000 cm-1 to 500 cm-1.

2.3 UV spectrophotometry:

The ultraviolet spectrum of a 0.01% solution of a sample of carbon dioxide extract from the herb Scabiosa ochroleuca in ethanol was taken in the range from 190 to 400nm, with a UV-Vis scan rate of 600.000nm/min; a UV-Vis data interval of 1.00nm; and a UV-Vis average time of 0.1000 sec.

Wavelength (λ, nm): 235.0; 202.0; 195.0; 193.0; 191.0

Absorbtion 0.689; 1.609; 0.426; 0.343; 0.333.

2.4 HPLC analysis:

Determination of α-santonin content in the grass of the studied plants by high-performance liquid chromatography (State Pharmacopoeia of the Republic of Kazakhstan, vol. 1, 2.2.29).

Preparation of a solution of a working standard sample of α-santonin: 0.011g (exact weight) of the working standard sample of α-santonin was placed in a measuring flask with a capacity of 25ml and dissolved in a mixture of acetonitrile: water (2:3). The volume of the solution was brought to the mark with the same solvent and mixed.

Approximately 2.0g (exact weight) of crushed raw material was placed in a round-bottomed flask with a capacity of 100ml, 50ml of chloroform was added, and the flask was attached to a reverse refrigerator, heated in a water bath at a temperature of 50-60^oC for 10 minutes and cooled. The extraction was repeated 2 more times. The extracts were combined and the solvent was evaporated on a rotary evaporator. The remainder was quantitatively transferred with a solution of the mobile phase into a measuring flask with a capacity of 25ml, the volume of the solution with the mobile phase was brought to the mark and mixed (the test solution). The resulting solution through with a 0.45µm (microns) pore size membrane filter was filtered.

Twenty milliliters (20ml) of the obtained filtrate and a solution of the working standard sample of α-santonin were alternately chromatographed on a liquid chromatograph with a UV detector, and at least 5 chromatograms were obtained for each of the solutions.

To verify the suitability of the chromatographic system before analyzing the tested solutions, 10ml of the filtrate of the working standard sample of α-santonin was chromatographed, and 5 chromatograms were obtained under the conditions described above.

Based on the test results:

· The efficiency of the chromatographic column calculated for the peak of α-santonin on chromatograms of the working standard sample of α-santonin was 15525 theoretical plates (at least 2000 t.p., State Pharmacopoeia XI, vol. 1);

· the peak symmetry coefficient calculated for the peak of α-santonin on the chromatograms of the solution of the working standard sample of α-santonin is 0.85 (no more than 2.0, State Pharmacopoeia XI vol. 1);

· The relative standard deviation calculated for the peak area of α-santonin on the chromatograms of the working standard sample of α-santonin was 0.94% (no more than 2.0%, State Pharmacopoeia XI, vol. 1).

Determination of α-santonin content in carbon dioxide extracts by high-performance liquid chromatography.

Test solution. CO₂-extract (0.033 g, extract weight) of from the herb scabiosa pale yellow, iset scabiosa was placed in 25ml measuring flask and dissolved in 10ml of a mixture of acetonitrile:water (2:3) when heated in a water bath. They were cooled and the volume of the solution was brought to the mark with the same solvent and mixed. The resulting solution through with a 0.45 µm (microns) pore size membrane filter was filtered.

The presence of α-santonin was established by comparing the retention time of the α-santonin peak on HPLC chromatograms of alcohol and aqueous extracts from CO₂ meal of carbon dioxide extraction of pale yellow grass scabiosa and a standard sample.

RESULTS AND DISCUSSION:

3.1 GC/MS analysis. On the GC/MS-chromatograms of the tested samples of the carbon dioxide extracts of herb scabiosa pale yellow, iset scabiosa and yellow-flowered Teasel, in accordance with Figures 1-3, at 101.694, 101.489 and 101.43 minutes, a peak with at M/z 246 appears, which corresponds to the molecular ion of sesquiterpene lactone α-santonin^16-17, which was identified as one of the main components of carbon dioxide extracts of Scabiosa ochroleuca L. (21.8%), Scabiosa isetensis L. (29.1%) and of Dipsacus strigosus Wild. (23.1%).

Figures 1-3 show GC/MS-chromatograms of carbon dioxide extracts of scabiosa pale yellow, iset scabiosa and yellow-flowered Teasel.

Figure 1. GC/MS-chromatogram of carbon dioxide extract of Scabiosa ochroleuca L.

Figure 2. GC/MS-chromatogram of carbon dioxide extract of Lomelosia isetensis (L.) Soják,

Figure 3. GC/MS-chromatogram of carbon dioxide extract of Dipsacus strigosus Willd.

3.2 IR spectroscopy:

The following absorption bands were detected in the IR spectra: a) carbon dioxide extract from the herb scabiosa pale yellow IR spectrum (KBr, n, cм^-1): 2920.24, 62.81; 1751.37,88.64; 1465.91,94.33; b) carbon dioxide extract from the herb iset scabiosa. IR spectrum (KBr, n, cм^-1): 2927.95. 45.54; 1735.94.73.84, 1465.91.82.32, 1172.72.87.63; c) carbon dioxide extract from the herb Yellow-flowered teasel. IR spectrum (KBr, n, cм^-1): 2935.67, 42.07; 1728.23, 65.7; 1465.91.82.32.

The presence of absorption bands at 2920.24. 62.81 cm^-1; 2927.95. 45.54 cm^-1 and 2935.67, 42.07 cm^-1 are characteristic of the valence vibrations of simple C-H bonds. The presence of an absorption band in the region of 1751.37.88.64 cm^-1; 1735.94.73.84 cm^-1 and 1728.23, 65.7 cm^-1indicates the presence of carbonyl of the lactone ring (C=O γ-lactone), and in the region of 1465.91.94.33 cm^-1; 1465.91.82.32 cm^-1 indicates the presence of an exocyclic methylene group conjugated with the carbonyl of γ-lactone²⁹.

IR spectra of alcohol and aqueous extracts from CO₂-meal of the herb Scabiosa ochroleuca L. The following absorption bands were detected by IR spectroscopy:

a) Alcohol extract from the waste of carbon dioxide extraction of the herb scabiosa pale yellow. IR spectrum (KBr, n, cм^-1): 3372 (strongly broadened band of associated valence vibrations O-H); 2971; 2926 (valence vibrations C-H); 1688 (valence vibrations C=O); 1626 (valence vibrations of aromatic bonds C=C); 1447 (valence vibrations of the C-H methyl group); 1379; 1271 (deformation vibrations of C-O); 1046; 926; 880; 607;

b) An aqueous extract from the waste of carbon dioxide extraction of the herb scabiosa pale yellow. IR spectrum (KBr, n, cм^-1): 3351.14 (strongly broadened band of associated valence vibrations O-H); 2928 (valence vibrations C-H); 1604 (valence vibrations of aromatic bonds C=C); 1404; 1264; 1075.64; 889.24; 817.84; 776.87; 613.00. In the studied spectra, the intense absorption bands approximately 926 cm^-1; 889 cm^-1; 880 cm^-1; 817 cm^-1; 776 cm^-1; 613 cm^-1; 607 cm^-1correspond to valence vibrations of the carbon skeleton (C−H) and nonplanar deformation (−CH) vibrations (=CH−) and (−CH₂−) groups. The intense bands at 1447.19 cm^-1and 1404.66 cm^-1 are attributed to the presence of an exocyclic methylene group conjugated with γ-lactone carbonyl, as are the closely spaced absorption bands 1688.61 cm^-1; 1626.19 cm^-1 and 1604.43 cm^-1due to the presence of ester (C=O) and carboxyl groups. Respectively in addition to the band (C = O), bands at 1264.54 1264.54 cm^-1; 1271.30 cm^-1; and 1046.08 cm^-1 (C–O) were assigned to ester groups the positions of which strongly depend on neighboring groups and bonds in the molecule, and can vary from 1040 to 1280 cm^-1. The high-intensity band of the valence vibrations at 3372.35 cm^-1 and 3351.14 cm^-1corresponds to the (-OH) group.

3.3 UV spectrophotometry:

The ultraviolet spectrum of a 0.01% solution of a sample of carbon dioxide extract from the herb Scabiosa ochroleuca L. in 96% ethyl alcohol, in the range between of 190 to 400nm, had an absorption maximum at a wavelength of 235nm, which is characteristic of an exocyclic methylene group conjugated with a γ-lactone carbonyl³⁰.

3.4 Determination of the content of α-santonin in the herbs of the studied plants by HPLC

The obtained HPLC chromatograms for determining the content of α-santonin in the raw material of Lomelosia isetensis (L.) Sojak. (Figure 4) and in the raw material of scabiosa pale yellow (Figure 5), and in a working standard sample of α-santonin (Figure 6). The retention time of α-santonin was 12.00±0.3min.

Figure 4. HPLC chromatogram of the quantitative content α-santonin in the grass of Lomelosia isetensis (L.) Sojak,

Figure 5. HPLC chromatogram of the quantitative content α-santonin in the grass of pale yellow scabiosa

Figure 6. HPLC chromatogram of the working standard sample of α-santonin

The presence of α-santonin in plants of the Caprifoliaceae Juss. family was confirmed.

CONCLUSION:

Studies of extracts from Scabiosa ochroleuca L., Lomelosia isetensis (L.) Soják. and Dipsacus strigosus Wild. provide prerequisites for further research and development of new medicines based on the plant raw materials Caprifoliaceae Juss. family.

CONFLICT OF INTEREST:

The authors have no conflicts of interest regarding this investigation.

This research has been/was/is funded by the Committee of Science of the Ministry of Science and Higher Education of the Republic of Kazakhstan (Grant No. BR 24992761).

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Received on 17.02.2024 Revised on 15.07.2024

Accepted on 23.10.2024 Published on 20.01.2025

Available online from January 27, 2025

Research J. Pharmacy and Technology. 2025;18(1):239-244.

DOI: 10.52711/0974-360X.2025.00037

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