Параметри стандартизації трави Alfredia nivea KAR.&KIR.

The Kazakhstan flora is rich in promising poorly-studied plants, which are traditionally used in folk medicine, but their introduction into medical practice requires additional in-depth research using modern scientific methods. Alfredia nivea KAR&KIR of the Asteraceae family, which is us...

Повний опис

Збережено в:
Бібліографічні деталі
Опубліковано в:Журнал органічної та фармацевтичної хімії
Дата:2023
Том:21
Випуск:1
Сторінки:46-53
ISSN:2518-1548
Автори та афіліації:
  • Almat G. Rustemkulov — Asfendiyarov Kazakh National Medical University
  • Tetiana M. Gontova — National University of Pharmacy of the Ministry of Health of Ukraine
  • Balzhan G. Makhatova — Asfendiyarov Kazakh National Medical University
  • Aisana E. Rustemkulova — Asfendiyarov Kazakh National Medical University
  • Ubaidilla M. Datkhayev — Asfendiyarov Kazakh National Medical University — ORCID: 0009-0009-8876-6927
  • Oleh M. Koshovyi — National University of Pharmacy of the Ministry of Health of Ukraine
Автори: Rustemkulov, Almat G., Gontova, Tetiana M., Makhatova, Balzhan G., Rustemkulova, Aisana E., Datkhayev, Ubaidilla M., Koshovyi, Oleh M.
Формат: Стаття
Мова:Англійська
Опубліковано: National University of Pharmacy 2023
Теми:
Онлайн доступ:https://ophcj.nuph.edu.ua/article/view/276004
Теги: Додати тег
Немає тегів, Будьте першим, хто поставить тег для цього запису!
Назва журналу:Journal of Organic and Pharmaceutical Chemistry
Завантажити файл: Pdf

Репозитарії

Journal of Organic and Pharmaceutical Chemistry
_version_ 1874364446741102592
author Rustemkulov, Almat G.
Gontova, Tetiana M.
Makhatova, Balzhan G.
Rustemkulova, Aisana E.
Datkhayev, Ubaidilla M.
Koshovyi, Oleh M.
author_facet Rustemkulov, Almat G.
Gontova, Tetiana M.
Makhatova, Balzhan G.
Rustemkulova, Aisana E.
Datkhayev, Ubaidilla M.
Koshovyi, Oleh M.
author_institution_txt_mv [ { "author": "Almat G. Rustemkulov", "institution": "Asfendiyarov Kazakh National Medical University", "orcid": "" }, { "author": "Tetiana M. Gontova", "institution": "National University of Pharmacy of the Ministry of Health of Ukraine", "orcid": "" }, { "author": "Balzhan G. Makhatova", "institution": "Asfendiyarov Kazakh National Medical University", "orcid": "" }, { "author": "Aisana E. Rustemkulova", "institution": "Asfendiyarov Kazakh National Medical University", "orcid": "" }, { "author": "Ubaidilla M. Datkhayev", "institution": "Asfendiyarov Kazakh National Medical University", "orcid": "0009-0009-8876-6927" }, { "author": "Oleh M. Koshovyi", "institution": "National University of Pharmacy of the Ministry of Health of Ukraine", "orcid": "" } ]
author_orcid_str_mv 0009-0009-8876-6927
author_sort Rustemkulov, Almat G.
baseUrl_str https://ophcj.nuph.edu.ua/oai
collection OJS
container_end_page 53
container_issue 1
container_start_page 46
container_title Журнал органічної та фармацевтичної хімії
container_volume 21
datestamp_date 2026-08-23T20:00:17Z
description The Kazakhstan flora is rich in promising poorly-studied plants, which are traditionally used in folk medicine, but their introduction into medical practice requires additional in-depth research using modern scientific methods. Alfredia nivea KAR&KIR of the Asteraceae family, which is used in folk medicine as a neurotropic agent, is an interesting object for introduction into official medical and pharmaceutical practice.Aim. To create new medicines based on Alfredia nivea herb, it is necessary to develop methods for quality control of this raw material, therefore, the aim of the research was to determine the parameters for standardization of the Alfredia nivea KAR & KIR. herb.Materials and methods. The study objects were samples of the A. nivea herb collected in Kungei Alatau, 4.3 km southeast of the Karabulak village, Eastern Karabulak canyon, Almaty Region, Kazakhstan. The macroscopic and microscopic studies of the A. nivea herb were performed according to the methodology of the European pharmacopeia (EuPh) 2.8.23 “Microscopic examination of the medicinal plant raw material”. The macroscopic studies were performed using a magnifying glass and a MBS-9 binocular microscope, the microscopic studies were done using MS Microscopes 10 (oculars X5, X10, X15, lenses x10,x40), Micromed XS-4130 (oculars WF15X, lenses x40/0.65, x10/0.25) with a microphotonozzle (China). Identification of the main substances was carried out by the TLC method, testing and the quantitative determination of the flavonoid content were performed according to the EuPh methods.Results and discussion. Morphological and anatomical features of the A. nivea herb have been determined; on their basis Identifications A and B have been proposed; TLC Identification C of the main BAS of the raw material has been developed; indicators of purity tests have been determined. It has been proposed to carry out the quantitative determination by the content of flavonoids.Conclusions. The parameters of the A. nivea herb standardization have been determined on the basis of the following indicators: macroscopic and microscopic features, TLC identification of the main BAS of the raw material (hyperoside, rutin, quercetin and chlorogenic acid), related impurities (not more than 2 %), stems with a diameter of more than 20 mm (not more than 10 %), the loss on drying (not more than 13 %), the total ash (not more than 10 %) and at least 0.5 % flavonoids calculated with reference to rutin.
doi_str_mv 10.24959/ophcj.23.276004
first_indexed 2025-07-23T04:43:16Z
format Article
fulltext ISSN 2308-8303 (Print) / 2518-1548 (Online) 46 Original Research http://ophcj.nuph.edu.ua UDC 615.322:582.998 A. G. Rustemkulov2, T. M. Gontova1, B. G. Makhatova2, A. E. Rustemkulova2, U. M. Datkhayev2, О. M. Коshovyi1 Standardization Parameters of Alfredia nivea KAR.&KIR Herb 1 National University of Pharmacy of the Ministry of Health of Ukraine, 53 Pushkinska str., 61002 Kharkiv, Ukraine 2 Asfendiyarov Kazakh National Medical University, 94 Tole bi str., 050000 Almaty, Kazakhstan Abstract The Kazakhstan flora is rich in promising poorly-studied plants, which are traditionally used in folk medicine, but their intro- duction into medical practice requires additional in-depth research using modern scientific methods. Alfredia nivea KAR&KIR of the Asteraceae family, which is used in folk medicine as a neurotropic agent, is an interesting object for introduction into official medical and pharmaceutical practice. Aim. To create new medicines based on Alfredia nivea herb, it is necessary to develop methods for quality control of this raw material, therefore, the aim of the research was to determine the parameters for standardization of the Alfredia nivea KAR & KIR. herb. Materials and methods. The study objects were samples of the A. nivea herb collected in Kungei Alatau, 4.3 km southeast of the Karabulak village, Eastern Karabulak canyon, Almaty Region, Kazakhstan. The macroscopic and microscopic studies of the A. nivea herb were performed according to the methodology of the European pharmacopeia (EuPh) 2.8.23 “Microscopic examination of the medicinal plant raw material”. The macroscopic studies were performed using a magnifying glass and a MBS-9 binocular microscope, the microscopic studies were done using MS Microscopes 10 (oculars X5, X10, X15, lenses x10, x40), Micromed XS-4130 (oculars WF15X, lenses x40/0.65, x10/0.25) with a microphotonozzle (China). Identification of the main substances was carried out by the TLC method, testing and the quantitative determination of the flavonoid content were performed according to the EuPh methods. Results and discussion. Morphological and anatomical features of the A. nivea herb have been determined; on their basis Identifications A and B have been proposed; TLC Identification C of the main BAS of the raw material has been developed; indicators of purity tests have been determined. It has been proposed to carry out the quantitative determination by the content of flavonoids. Conclusions. The parameters of the A. nivea herb standardization have been determined on the basis of the following in- dicators: macroscopic and microscopic features, TLC identification of the main BAS of the raw material (hyperoside, rutin, quercetin and chlorogenic acid), related impurities (not more than 2 %), stems with a diameter of more than 20 mm (not more than 10 %), the loss on drying (not more than 13 %), the total ash (not more than 10 %) and at least 0.5 % flavonoids calculated with reference to rutin. Keywords: Alfredia nivea; herb; standardization; quality control methods А. Г. Рустемкулов2, Т. М. Гонтова1, Б. Г. Махатова2, А. Є. Рустемкулова2, У. М. Датхаєв2, О. М. Кошовий1 1 Національний фармацевтичний університет Міністерства охорони здоров’я України, вул. Пушкінська, 53, м. Харків, 61002, Україна 2 Казахський національний медичний університет імені С. Д. Асфендіярова, вул. Толе бі, 94, м. Алмати, 050000, Казахстан Параметри стандартизації трави Alfredia nivea KAR.&KIR. Анотація Флора Казахстану багата на перспективні маловивчені рослини, які застосовують у народній медицині, але для їх впро- вадження в медичну практику потрібні додаткові глибокі дослідження, за допомогою сучасних наукових методів. Цікавим об’єктом для впровадження в офіцинальну медичну та фармацевтичну практику є Альфредія снігова (Alfredia nivea KAR. & KIR.) родини Asteraceae, яку в народній медицині використовують як нейротропний засіб. Мета. Для створення нових лікарських засобів на основі трави Альфредії снігової необхідно розробити методи контролю якості цієї сировини, тому метою досліджень було визначити параметри стандартизації трави A. nivea KAR. & KIR. ISSN 2308-8303 (Print) / 2518-1548 (Online) 47 Journal of Organic and Pharmaceutical Chemistry 2023, 21 (1) Матеріали та методи. Об’єктами дослідження були зразки трави Альфредії снігової (A. nivea), заготовлені в Кунгей Алатау, за 4,3 км південно-східніше від с. Карабулак, ущ. Східний Карабулак, Алматинської області, Казахстан. Макро- і мі- кроскопічні дослідження трави Альфредії снігової виконували згідно з методикою Європейської фармакопеї (ЄФ) 2.8.23 «Мікроскопічне дослідження лікарської рослинної сировини». Для макроскопічних досліджень використовували лупу та бінокулярний мікроскоп МБС-9, для мікроскопічних – мікроскопи МС 10 (окуляр х5, х10, х15, об’єктиви х10, x40), Micromed XS-4130 (окуляр WF15X, об’єктиви х40/0,65, х10/0,25) з мікрофотонасадкою (КНР). Ідентифікували основні речовини мето- дом ТШХ, випробування та кількісне визначення за вмістом флавоноїдів здійснювали відповідно до методик ЄФ. Результати та їх обговорення. Визначено морфологічні й анатомічні ознаки трави Альфредії снігової, на основі яких запропоновано Ідентифікації А та В, розроблено ТШХ Ідентифікацію С основних БАР сировини, визначено показни- ки випробувань на чистоту, а також запропоновано проводити кількісне визначення за вмістом флавоноїдів. Висновки. Визначено параметри стандартизації трави Альфредії снігової за такими показниками: макро- та мікро- скопічні ознаки, ТШХ ідентифікація основних БАР сировини (гіперозид, рутин, кверцетин та хлорогенова кислота), сторонні домішки (не більше 2 %), наявність стебел діаметром понад 20 мм (не більше 10 %), втрата в масі під час висушування (не більше 13 %), загальна зола (не більше 10 %) і не менше 0,5 % флавоноїдів у перерахунку на рутин. Ключові слова: Альфредія снігова; Alfredia nivea; трава; стандартизація; методи контролю якості Citation: Rustemkulov, A. G.; Gontova, T. M.; Makhatova, B. G.; Rustemkulova, A. E.; Datkhayev, U. M.; Коshovyi, О. M. Standardization parameters of Alfredia nivea Kar. & Kir herb. Journal of Organic and Pharmaceutical Chemistry 2023, 21 (1), 46 – 53. https://doi.org/10.24959/ophcj.23.276004 Received: 29 December 2022; Revised: 30 January 2023; Accepted: 10 February 2023 Copyright© 2023, A. G. Rustemkulov, T. M. Gontova, B. G. Makhatova, A. E. Rustemkulova, U. M. Datkhayev, О. M. Коshovyi. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0). Funding: The authors received no specific funding for this work. Conflict of interests: The authors have no conflict of interests to declare. ■ Introduction The Kazakhstan flora is rich in promising poorly-studied plants, which are traditionally used in folk medicine, but their introduction into me- dical practice requires additional in-depth re- search using modern scientific methods [1, 2]. Alfredia nivea KAR&KIR of the Asteraceae fami- ly, which is used in folk medicine as a neurotro- pic agent, is an interesting object for introduc- tion into official medical and pharmaceutical practice in Kazakhstan [3]. A. nivea is a perennial plant of 25 – 70 cm height with leathery, oblong-lanceolate, pinnate- ly lobed leaves. The venation is pinnate, the la- teral veins at the ends turn into sharp yellowish spines. The leaf blade is grayish-green on the upper side, whitish-pubescent on the lower side. The inflorescence is a spherical head of pink tubu- lar flowers with a multi-row involucre. The plant blooms in July, fruits ripen in August – Septem- ber. It grows in the subalpine and alpine belts of the mountains, along the stepped rocky slopes, in spruce-fir forests. It is found in Tarbagatai, Dzungarian, Trans-Ili and Küngöy Ala-Too Range Alatau [4 – 6]. The plant’s raw material reserves are sufficient for the needs of Kazakhstan. Plants of the Alfredia genus are insufficient- ly studied. Most of the studies are devoted to A. cernua L. Thus, extracts of this species have been shown to affect the central nervous system and improve memory [7, 8]. It has also been found that A. cernua extracts have nootropic properties, contribute to the improvement of indicators of orientation-exploratory behavior, the preserva- tion of the passive escape reflex during hypoxic shock, and the increase of physical performance in mice [9, 10]. The most pronounced effect was observed with the use of the A. cernua extract obtained with 95 % ethanol [10, 11]. It has also been shown that the extract of the A. nivea above-ground part in 95 % ethanol in the dose of 100 mg kg–1 restores exploratory behavior and reflex safety after hypoxic trauma [12]. Thus, the A. nivea herb is a promising raw material for creating new neurotropic medicines. Previously, the standardization of the A. cer- nua herb [13], the macroscopic and microscopic study of the A. nivea herb were carried out, and its diagnostic signs were determined [14]. These data were taken into account when developing a project of quality control methods for the A. ni- vea herb. Therefore, the aim of the research was to de- termine the parameters of the standardization of the A. nivea KAR. & KIR. herb. ■ Materials and methods The study objects were samples of the A. nivea herb collected in Kungei Alatau, 4.3 km south- east of the Karabulak village, Eastern Karabulak canyon, Almaty Region, Kazakhstan (1762 m abo- ve the city, N 43°02’30.2”, E 078°34’16.0”) July ISSN 2308-8303 (Print) / 2518-1548 (Online) 48 Журнал органічної та фармацевтичної хімії 2023, 21 (1) 06, 2021. The identity of the plant was determi- ned by professor Tetiana M. Gontova, D. Sc., Na- tional University of Pharmacy (Kharkiv, Ukrai- ne) [4, 15]. Voucher specimens were deposited at the School of Pharmacy, Asfendiyarova Kazakh Na- tional Medical University (Almaty, Kazakhstan, No. 432 – 435). The raw material was dried at room temperature [16, 17] in a well-ventilated area for ten days and stored in paper bags [18, 19]. The macroscopic and microscopic studies of the raw material were performed according to the methodology described in the European Pharma- copeia (EuPh) 2.8.23 “Microscopic examination of the medicinal plant raw material” [18, 20]. The macroscopic studies were conducted using a magnifying glass and a MBS-9 binocular micro- scope. The study of the anatomical structure of the A. nivea herb was carried out on samples of the whole and cut raw material according to the requirements of the EuPh. The herb was fixed in a mixture of 96 % ethanol R – glycerin R – pu- rified water R (1:1:1). The structure of stems and leaves was studied on transverse sections. The epidermal of the organs was considered from the surface according to generally accepted me- thods [18, 21]. The raw material was crushed ac- cording to the requirements of the EuPh mono- graph 2.9.12 “Sit analysis” and clarified with the help of chloral hydrate R [18, 20]. The studies of transverse and longitudinal sections, epider- mis and preparations from the surface were car- ried out using MS Microscopes 10 (oculars X5, X10, X15, lenses x10, x40), Micromed XS-4130 (oculars WF15X, lenses x40/0.65, x10/0.25) with a microphotonozzle (China). The results of the study were recorded using the Canon IXUS 220 HS camera. To develop the identification method for the main biologically active substances (BAS) in the A. nivea herb, the TLC method was used [18, 22]. Merck Silica Gel F254 plates were used for chro- matography. Purity of solvents used for the pre- paration of chromatographic systems were of che- mically pure and analytical grades. The ratio of solvents indicated by numbers were taken in vo- lumetric units. The content of related impurities (2.8.2), the loss on drying (2.2.32), the total ash content (2.4.16) were determined according to the re- quirements of the EuPh [18, 23, 24]. Assay of flavonoids. The assay of flavonoids was determined in accordance with the metho- dology of the EuPh by the spectrophotometric me- thod calculated with reference to rutin [18, 25]. About 5.0 g of Alfredia herb (accurate weight) crushed to the size of particles passing through a sieve with a diameter of 2 mm was placed in a 200 mL ground joint flask, 50 mL of 70 % etha- nol solution was added. The flask was connected to a condenser and heated on a water bath for 30 min, periodically shaken to wash off partic- les of the raw material from the walls. The mix- ture was cooled and filtered through cotton wool, so that the particles of the raw material did not get on the filter. The cotton wool was transferred to the ground joint flask for extraction, and the new portion of the extractant was added. The ex- traction was repeated twice under the conditions described above, and the extract was filtered in the same flask. The combined extract was evap- orated up to ¼ of the initial volume. The evapo- rated extract was quantitatively transferred to a 50.0 mL measuring flask, cooled and was di- luted with 70 % ethanol solution to the volume (Solution A). 2.0 mL of Solution A was placed into a measu- ring 25 mL flask, 2.0 mL of 3 % aluminum chloride solution in 96 % ethanol R was added, the volume was diluted with 70 % ethanol solution and mixed. In 30 min, the solution was filtered through the paper filter, throwing away the first portions of the filtrate, and the optical density was meas- ured on a Specol 1500 spectrophotometer (Swit- zerland) at a wavelength of 410 nm in a 10 mm cuvette. Reference solution contained 2.0 mL of Solution A, diluted with 70 % ethanol to the vol- ume in a 25 mL flask. In parallel, experiment with a Standard solu- tion of rutin (pharmacopoeial standard) was car- ried out in the same conditions. 1.0 mL of 3 % alu- minum chloride solution was added to 1.0 mL of the Standard solution of rutin, and the volume was diluted to 25.0 mL with 70 % ethanol. As a referen- ce, 1.0 mL of the Standard solution of rutin diluted with 70 % ethanol to the volume of 25 mL was used. The content of flavonoids in the raw material was calculated with reference to rutin (%) by the following equation [28, 29]: X, % � A × a × × × × ×1 0 50 1 25 100 100 , A × a × × × × – w0 1 25 2 50 (100 ) where А1 – is the optical density of the Test solu- tion; А0 – is the optical density of the Standard solu- tion of rutin; а1 – is the accurate weight of raw material, g; а0 – is the accurate weight of rutin, g; w – is the loss on drying,  %. ISSN 2308-8303 (Print) / 2518-1548 (Online) 49 Journal of Organic and Pharmaceutical Chemistry 2023, 21 (1) Preparation of the standard solution of rutin. About 0.01 g (accurate weight) of rutin (pharma- copoeial standard FS 42-2508-87) dried at 135 oC to the constant mass, was placed into a 25.0 mL measuring flask, dissolved in 96 % ethanol, di- luted with the same solvent to the volume and mixed. Preparation of a 3 % aluminum chloride solu- tion in 96 % ethanol. According to the State stan- dard 3759-85, 3.0 g of aluminum chloride (chemi- cally pure) was dissolved in 96 % ethanol in a 100.0 mL measuring flask, diluted with the same solvent to the volume and mixed. ■ Results and discussion Source. The raw material is a dried herb, which includes whole or cut leaves, flowers and stems of A. nivea KAR. & KIR. (Asteraceae). The herb was collected in summer, the below ground parts were removed, and then the soil was dried to obtain the intact form. Alternatively, the herb was sliced while fresh, and dried immediately to obtain the sliced form of the A. nivea herb. Based on the results of the macroscopic ana- lysis of the A. nivea herb [14], such macroscopic signs, which served as the basis for the develop- ment of Identification A, were determined. The stem is usually unbranched in the lower part, slightly branched in the upper part, rough, slightly ribbed, 20 – 60 cm long, 5 mm in diameter. It is externally grayish-green, tomentose-pubes- cent. The texture is hard. Rosette leaves are 15 – 35 cm long and 2.5 – 6.0 cm wide; stem leaves are short-petiolate or sessile, 5.0 – 7.0 cm long and 1.5 – 2.5 cm wide, leathery, linear-lanceolate and lanceolate, pinnatipartite, with a pinnate vena- tion with prominent lignified veins and long sharp ends; non-tomentose and green on the adaxial surface and grayish green, abundant tomentose- pubescent on the abaxial surface. The petiole of the rosette leaf is elongated-triangular in out- line with elongated “wings” directed upwards at an angle of 45 degrees, narrow at the ends. The inflorescence is a spherical drooping flo- wer head up to 6.0 cm in diameter with a 3 – 5-row, tiled involucre made of hard lanceolate, pointed leaflets with filmy fring-rowed outgrowths on the sides. The tubular pink flowers are 5-tooth, thin, up to 3.0 cm in length; numerous sepals are mo- dified to thin long hairs; stamens and the pis- til protrude from the corolla tube; the cypsela is up to 6.0 mm, pale yellowish with variegated brown spots and stripes on the surface. Based on the results of the microscopic ana- lysis of the A. nivea herb [14], such microscopic signs, which served as the basis for the develop- ment of Identification B, were determined. The stem and leaves are tomentose-pubescent with covering and rarely glandular trichomes; co- vering trichomes are of three types – long filamen- tous hairs with a 2-cell base, large multicellular wide lumen hairs with collapsed cells; and multi- cellular narrow lumen hairs with collapsed cells; glandular hairs are of 2 types – 1-headed with a 1-celled stalk, and headed with a multicellular stalk and a multicellular head with collapsed cells. The stem is rounded with slightly protruding ribs. The cells of the epidermis are covered with a layer of a folded cuticle; prosenchymatous cells are straight-walled with slightly thickened walls and simple straight pores. The central cylinder is of transitional type. The collenchyma is angular and lacunar; parenchyma cells are collenchymatous; the endoderm is distinct; open collateral bundles are with a well-developed sclerenchyma, xylem vessels are porous and spiral. Leaf is dorsiventral; the cells of the upper and lower epidermis above the veins are prosenchy- matous, straight-walled, with slightly thickened walls and straight pores; between the veins the cells of the upper epidermis are 5 – 6-angle, iso- diametric and on the lower – parenchymal, si- nuous-walled, with slightly thickened walls; the stomata are frequent only on the lower epider- mis. The stomatal apparatus is anomocytic. The adaxial surface of the leaf is rarely pu- bescent with thin long hairs, and abaxial – den- sely pubescent with filamentous hairs with a 2-cell base and less often multicellular hairs with col- lapsed cells. The cells of the outer and inner epi- dermis of the involucre leaflets are elongated, slightly thickened and straight-walled with light brown contents. The inner epidermis is covered with filamentous trichromes. The cells of the pe- tal epidermis are prosenchymatous, thin-walled or heavily thick-walled, straight-walled with co- lorless, rarely brown contents; the epidermis is covered with a weakly expressed folding cuticle; vessels are thin spiral. The style of the pistil is densely covered with short conical hairs. Pollen grains are rounded, yellow-brown, the structure of ectine is slightly spiny. The powdered raw material. The powder is yellowish-green in color, examined under a mic- roscope using Chloral hydrate solution R. The pow- der shows the following diagnostic signs: frag- ments of epidermis (Figure 1, A) composed of cells ISSN 2308-8303 (Print) / 2518-1548 (Online) 50 Журнал органічної та фармацевтичної хімії 2023, 21 (1) A B C D E F G H I J K L M Figure 1. Microscopic features of the powder ISSN 2308-8303 (Print) / 2518-1548 (Online) 51 Journal of Organic and Pharmaceutical Chemistry 2023, 21 (1) with prosenchymatous straight-walled and slightly thick-walled cells with simple straight pores (Fi- gure 1, B); cells with light brown contents (Figu- re 1, C); stomata of the anomocytic type (Figure 1, A); fragments of the angular and lacunar collenchy- ma (Figure 1, D); collenchymatous cells of the pa- renchyma (Figure 1, E); open collateral bundles (Figure 1, F); sclerenchyma (Figure 1, G), porous and spiral vessels; long filamentous hairs with a 2-cell base, large multicellular wide lumen hairs with collapsed cells (Figure 1, H), and multicellu- lar narrow lumen hairs with collapsed cells (Fi- gure 1, I); glandular hairs of 2 types – 1-headed with a 1-celled stalk (Figure 1, J), and headed with a multicellular stalk and a multicellular head with collapsed cells (Figure 1. K); styles with short conical hairs (Figure 1, L); rounded, yellow-brown pollen grains with slightly spiny ectine (Figure 1, M). Identification C of BAS of the A. nivea herb was developed using the TLC method with stan- dards of hyperoside, quercetin, rutin and chloro- genic acid in the system: ethylacetate R – aqua R – formic acid R – acetic acid anhydrous R (72:14:7:7). For this analysis, 300 mg of the Alfredia herb was extracted with 3 mL of methanol for 30 min at 40 oC on a water bath with ultrasound irra- diation. 15 μL of the extract was applied to the chromatogram. The standards were prepared by dissolving 1 mg of the standards in 10 mL of pure methanol. After spraying the plate with diphenyl- borinic acid 2-aminoethyl ester R, macrogol 400 R the zones at the level of quercetin, hyperoside, rutin and chlorogenic acid were detected in UV light [28]. A photo of the sequence of zones on the chro- matogram of the A. nivea the test extract and the reference solutions are presented in Figure 2. The main substances found in the TLC chroma- togram are quercetin, chlorogenic acid, rutin and hyperoside. Other additional fluorescent zones can be found on the chromatogram of the test extract, but they do not play an important role when iden- tifying the raw material. Also, using the chroma- togram obtained in the same conditions, after spraying the plate with the Drangendorff rea- gent [29], it was determined that there were no alkaloids in the raw material. In the lower part of the chromatogram of the reference solutions, a yellow fluorescent zone corresponding to rutin, as well as the blue fluo- rescent zone corresponding to chlorogenic acid, and the yellow fluorescent zone corresponding to hyperoside, were found. The yellow fluorescent zone corresponding to quercetin was detected in the upper part of the chromatogram. On the chromatogram of the test extract, the intense fluorescent yellow zone at the level of the refer- ence solution of rutin was detected. At the level of the reference solution of chlorogenic acid the intense blue fluorescent zone was also deter- mined. Since the zones of rutin and quercetin are most clearly identified and have a significant area du- ring the TLC analysis, it has been noticed that they dominate in the raw material, therefore, the quantitative determination of BAS in the A. ni- vea herb should be carried out by the assay of fla- vonoids calculated with reference to rutin adapt- ing the methodology of the EuPh [18]. The results of determining related impuri- ties, indicators “loss on drying during drying”, “total ash” and the quantitative content of flavo- noids are given in Table. The tests were proposed to be carried out ac- cording to the following indicators: related im- purities (2.8.2), namely, stems with a diameter of more than 20 mm – not more than 10 %; other impurities – not more than 2 %; the loss on dry- ing (2.2.32) – not more than 13.0 % (1.000 g of the raw material crushed into a powder at a tem- perature of 105oC for 2 h); the total ash (2.4.16) – not more than 10 %. 1 2 3 Figure 2. The TLC chromatogram of A. nivea phenolic compounds: 1. the standards of quercetin, chlorogenic acid, rutin; 2. hyperoside; 3. the A. nivea herb extract ISSN 2308-8303 (Print) / 2518-1548 (Online) 52 Журнал органічної та фармацевтичної хімії 2023, 21 (1) The assay was proposed to be carried out by the content of flavonoids – at least 0.5 % calcula- ted with reference to rutin (C27N30O16; M.M. 610.5) in the dry raw material. ■ Conclusions The parameters of the A. nivea herb stan- dardization have been determined on the basis of the following indicators: macroscopic and mic- roscopic features, TLC identification of the main BAS of the raw material (hyperoside, rutin, quer- cetin and chlorogenic acid), related impurities (not more than 2 %), stems with a diameter of more than 20 mm (not more than 10 %), the loss on drying (not more than 13 %), the total ash (not more than 10 %) and at least 0.5 % flavo- noids calculated with reference to rutin. ■ References 1. Zhumashova, G.; Kukula-Koch, W.; Koch, W.; Baj, T.; Sayakova, G.; Shukirbekova, A.; Głowniak, K.; Sakipova, Z. Phytochemical and an- tioxidant studies on a rare Rheum cordatum Losinsk. Species from Kazakhstan. Oxidative Medicine and Cellular Longevity 2020, 2019, Article ID 5465463. https://doi.org/10.1155/2019/5465463. 2. Sayakova, G.; Boshkayeva, A.; Ibadullayeva, G.; Khamitova, A.; Begimova, G. Actual prospects of using some types of larch growing in Kazakhstan in medicine. Journal of medicine and life 2022, 15 (8), 1038 – 1046. https://doi.org/10.25122/jml-2021-0373. 3. Kiyekbayeva, L. N.; Datkhayev, U. M.; Derbisbekova, U. B.; Akhtaeva, N. C.; Litvinenko, Y. A. Phytochemical investigation and technology production of alkaloids in the Kazakh endemic plant Echinops albicaulis Kar.Et Kir. (Asteraceae). International Journal of Green Phar- macy 2017, 11 (2, Suppl. issue), S312 – S319. https://doi.org/10.22377/ijgp.v11i02.1041. 4. Catalogue of Life China: 2022 Annual Checklist, Beijing, China. http://www.gbifchina.org.cn/resource?r=species2000-2022-annual#anchor- citation (accessed January 17, 2023). 5. Novozhilova, E. V.; Boyko, E. V. Morphological and anatomical structure of the cypselas of Alfredia (Asteraceae: Cardueae). Turczani- nowia 2019, 22 (4), 42 – 56. 6. Korneyev, S. V. Revision of species of the genus Tephritis Latreille 1804 (Diptera: Tephritidae) with entire apical spot. Zootaxa 2013, 3620 (1), 067 – 088. http://dx.doi.org/10.11646/zootaxa.3620.1.3. 7. Shilova, I. V.; Kuvacheva, N. V.; Kolmakova, A. A.; Losev, V. N.; Minakova, M. Y. Biologically Active Substances in the Aqueous Frac- tion of Alfredia cernua (L.) Cass. Extract Possessing Antiamnesic Properties. Pharm. Chem. J. 2021, 54 (12), 1239 – 1242. https://doi. org/10.1007/s11094-021-02349-5. 8. Shilova, I. V.; Baranovskaja, N. V.; Mustafin, R. N.; Suslov, N. I. Features of the composition macro elements and trace elements of the extract of Alfredia cernua (L.) Cass., possessing psychotropic effect. Khimiya Rastitel’nogo Syr’ya 2019, 4, 191 – 198. https://doi. org/10.14258/jcprm.2019045422. 9. Shilova, I. V.; Kukina, T. P.; Suslov, N. I.; Sal’nikova, O. I.; Mustafin, R. N. Studies of the Lipophilic Components of a Dense Extract of the Herb Alfredia Cernua and its Nootropic Properties. Pharm. Chem. J. 2014, 48 (3), 181 – 185. https://doi.org/10.1007/s11094-014- 1074-y. 10. Mustafin, R. N.; Suslov, N. I.; Shilova, I. V.; Kuvacheva, N. V. Influence of Alfredia cernua extracts on the behavior, memory, and physical work capacity of experimental animals. Eksperimental’naya i klinicheskaya farmakologiya 2010, 73 (1), 16 – 19. 11. Mustafin, R. N.; Shilova, I. V.; Suslov, N. I.; Kuvacheva, N. V.; Amelchenko, V. P. Nootropic Activity of Extracts from Wild and Cultivated Alfredia Cernua. Bulletin of Experimental Biology and Medicine 2011, 150 (3), 333 – 335. https://doi.org/10.1007/s10517-011-1135-0. 12. Shilova, I. V.; Suslov, N. I. Nejroprotektornaya aktivnost biologicheski aktivnyh veshestv Alfredia nivea [Neuroprotective activity of bio- logically active substances from Alfredia nivea, in Russian]. In The role of metabolomics in the improvement of biotechnological means of production, Proceedings of the 2nd International scientific conference, June 06 – 07, 2019, 223 – 227. Table. The results of the analysis of the A. nivea herb Indicators Standardization Samples of the raw material 1 2 3 4 5 6 Description According to the parameters developed + + + + + + Identification A. External signs – macroscopy According to the parameters developed + + + + + + Identification B. Anatomical signs – microscopy According to the parameters developed + + + + + + Identification C. TLC method According to the parameters developed + + + + + + Impurities Stems with a diameter of more than 20 mm not more than 10 % 8.7 6.2 9.6 7.1 8.5 8.0 Related impurities – not more than 2 % 1.5 1.8 1.0 1.5 1.0 0.5 Loss on drying Not more than 13.0 % 8.7 9.3 7.2 9.7 8.5 11.0 Total ash Not more than 10 % 7.2 6.6 8.6 5.3 8.2 8.9 The content of flavonoids calculated with reference to rutin Not less than 0.5 % 0.74 0.69 0.63 0.76 0.60 0.58 Note: «+» – meets the requirements ISSN 2308-8303 (Print) / 2518-1548 (Online) 53 Journal of Organic and Pharmaceutical Chemistry 2023, 21 (1) 13. Kuvacheva, N. V.; Shilova, I. V. Standartizaciya travy alfredii ponikshej [Standardization of the herb Alfredia cernua, in Russian]. Voprosy biologicheskoj, medicinskoj i farmacevticheskoj himii 2011, 5, 9 – 12. 14. Rustemkulov, A.; Gontova, T.; Makhatova, B.; Rustemkulova, A.; Gemedzhieva, N.; Shormanova, A.; Starchenko, G.; Raal, A.; Datkhaev, U.; Koshovyi, O. Macro and microscopic analysis of Alfredia nivea KAR. & KIR herb. ScienceRise: Pharmaceutical Science 2023, 1, 41 – 49. https://doi.org/10.15587/2519-4852.2023.274766. 15. Baitenov, M. S. Flora Kazakhstana. Illyustrirovannyj opredelitel rodov i semejstv (Tom 1) [Kazakhstan flora. Illustrated guide to genera and families (Vol. 1), in Russian]. Almaty, 1999. 16. Shynkovenko, I. L.; Ilyina, Т. V.; Kovalyova, А. М.; Goryacha, O. V.; Golembiovska, O. I.; Koshovyi, O. M. Saponins of the extracts of Ga- lium aparine and Galium verum. News of Pharmacy 2018. 4, 16 – 23. https://doi.org/10.24959/nphj.18.2225. 17. Vlasova, І. K.; Koshovyi, O. M. Standardization of dry extracts from large cranberry leaves. Journal of organic and pharmaceutical chemis- try 2022, 20 (3), 40 – 45. https://doi.org/10.24959/ophcj.22.265845. 18. European Pharmacopoeia. 10th Ed. Council of Europe, Strasbourg. 2019. 19. Shanaida, M.; Hudz, N; Korzeniowska, K.; Wieczorek, P. Antioxidant activity of essential oils obtained from aerial part of some Lami- aceae species. International Journal of Green Pharmacy 2018, 12 (3), 200 – 204. https://doi.org/10.22377/ijgp.v12i03.1952. 20. Vlasova, I.; Gontova, T.; Grytsyk, L. et al. Determination of standardization parameters of Oxycoccus macrocarpus (Ait.) Pursh and Oxy- coccus palustris Pers. Leaves. ScienceRise: Pharmaceutical Science 2022, 3, 48 – 57. http://doi.org/10.15587/2519-4852.2022.260352. 21. Kiyekbayeva, L. N.; Akhtaeva, N. Z.; Datkhayev, U. M.; Omarkhan, A. B.; Litvinenko, Y. A.; Tynybekov, B. M.; Berkenov, A. K. Pharmacognosy signs of aerial parts medicinal plant Echinops albicaulis KAR. & KIR. Asian Journal of Pharmaceutical and Clinical Research 2017, 10 (6), 346 – 348. https://doi.org/10.22159/ajpcr.2017.v10i6.18037. 22. Koshovyi, O.; Romanenko Ye.; Komissarenko A. The study of the phenolic composition of the dry extract of motherwort herb and its psychotropic activity. American Journal of Science and Technologies 2016, 3 (1), 1055 – 1059. 23. Krivoruchko, E.; Markin, A.; Samoilova, V.; Ilina, T.; Koshovyi, O. Research in the chemical composition of the bark of Sorbus aucuparia. Ceska a Slovenska farmacie: casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti 2018, 67 (3), 113 – 115. 24. Myha, M.; Koshovyi, O.; Gamulya, O.; Ilina, T.; Borodina, N.; Vlasova, I. Phytochemical study of Salvia grandiflora and Salvia officinalis leaves for establishing prospects for use in medical and pharmaceutical practice. ScienceRise: Pharmaceutical Science 2020, 1, 23 – 28. https://doi.org/10.15587/2519-4852.2020.197299. 25. Koshovyi, O.; Granica, S.; Piwowarski, J.P.; Stremoukhov, O.; Kostenko, Y.; Kravchenko, G.; Krasilnikova, O.; Zagayko, A. Highbush Blue- berry (Vaccinium corymbosum L.) Leaves Extract and Its Modified Arginine Preparation for the Management of Metabolic Syndrome— Chemical Analysis and Bioactivity in Rat Model. Nutrients 2021, 13, 2870. https://doi.org/10.3390/nu13082870. 26. Chaika, N.; Koshovyi, O.; Ain, R.; Kireyev, I.; Zupanets, A.; Odyntsova, V. Phytochemical profile and pharmacological activity of the dry extract from Arctostaphylos uva-ursi leaves modified with phenylalanine. ScienceRise: Pharmaceutical Science 2020, 6, 74 – 84. https:// doi.org/10.15587/2519-4852.2020.222511. 27. Shinkovenko, I. L.; Kashpur, N. V.; Ilyina, T. V.; Kovalyova, A. M.; Goryacha, O. V.; Koshovyi, O. M.; Toryanyk, E. L.; Kryvoruchko, O. V. The immunomodulatory activity of the extracts and complexes of biologically active compounds of Galium verum L. herb. Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti 2018, 67 (1), 25 – 29. 28. Koshovyi, O. M. Fenolnyi sklad deiakykh predstavnykiv pidrodu Sclarea rodu Salvia [Phenolic composition of some representatives of the subgenus Sclarea of the genus Salvia, in Ukrainian]. Current issues in pharmacy and medicine: science and practice 2012, 3, 11–14. 29. Raal, A.; Meos, A.; Hinrikus, T.; Heinämäki, J.; Romāne, E.; Gudienė, V.; Jaktas, V.; Koshovyi, O.; Kovaleva, A.; Fursenco, C.; Chiru, T.; Nguyen, H. T. Dragendorff’s reagent: Historical perspectives and current status of a versatile reagent introduced over 150 years ago at the University of Dorpat, Tartu, Estonia. Die Pharmazie – An International Journal of Pharmaceutical Sciences 2020, 75 (7), 299 – 306. https://doi.org/10.1691/ph.2020.0438. Information about the authors: Almat G. Rustemkulov, Postgraduate Student of the “Pharmaceutical Production Technology” Program, Asfendiyarov Kazakh National Medical University; https://orcid.org/0000-0002-1792-9399; e-mail: arustemkulov@gmail.com. Tetiana M. Gontova, D.Sc. in Pharmacy, Professor of the Pharmacognosy Department, National University of Pharmacy of the Ministry of Health of Ukraine; https://orcid.org/0000-0003-3941-9127; e-mail: tetianaviola@ukr.net. Balzhan G. Makhatova, Postgraduate Student, Associate Professor of Engineering Disciplines and Good Practices Department, Asfendiyarov Kazakh National Medical University; https://orcid.org/0000-0002-0206-0416; e-mail: makhatova.b@kaznmu.kz. Aisana E. Rustemkulova, Postgraduate Student of the “Pharmaceutical Production Technology” Program, Asfendiyarov Kazakh National Medical University; https://orcid.org/0000-0003-2363-7576; e-mail: rustemkulova.a@gmail.com. Ubaidilla M. Datkhaev, D.Sc. in Pharmacy, Professor, Vice-Rector for Corporate Development, Asfendiyarov Kazakh National Medical University; https://orcid.org/0000-0002-2322-220X. Oleh M. Koshovyi (corresponding author), D.Sc. in Pharmacy, Professor of the Pharmacognosy Department, National University of Pharmacy of the Ministry of Health of Ukraine; https://orcid.org/0000-0001-9545-8548; e-mail for correspondence: oleh.koshovyi@gmail.com.
id oai:ojs.journals.uran.ua:article-276004
institution Journal of Organic and Pharmaceutical Chemistry
issn 2518-1548
keywords_txt_mv
language English
last_indexed 2026-08-24T01:00:32Z
publishDate 2023
publisher National University of Pharmacy
record_format ojs
resource_txt_mv ophcjnupheduua/54/035918d20ad5d78327de8f1d00431254.pdf
spelling oai:ojs.journals.uran.ua:article-2760042026-08-23T20:00:17Z Standardization Parameters of Alfredia nivea KAR.&KIR Herb Параметри стандартизації трави Alfredia nivea KAR.&KIR. Rustemkulov, Almat G. Gontova, Tetiana M. Makhatova, Balzhan G. Rustemkulova, Aisana E. Datkhayev, Ubaidilla M. Koshovyi, Oleh M. Альфредія снігова Alfredia nivea трава стандартизація методи контролю якості Alfredia nivea herb standardization quality control methods The Kazakhstan flora is rich in promising poorly-studied plants, which are traditionally used in folk medicine, but their introduction into medical practice requires additional in-depth research using modern scientific methods. Alfredia nivea KAR&KIR of the Asteraceae family, which is used in folk medicine as a neurotropic agent, is an interesting object for introduction into official medical and pharmaceutical practice.Aim. To create new medicines based on Alfredia nivea herb, it is necessary to develop methods for quality control of this raw material, therefore, the aim of the research was to determine the parameters for standardization of the Alfredia nivea KAR & KIR. herb.Materials and methods. The study objects were samples of the A. nivea herb collected in Kungei Alatau, 4.3 km southeast of the Karabulak village, Eastern Karabulak canyon, Almaty Region, Kazakhstan. The macroscopic and microscopic studies of the A. nivea herb were performed according to the methodology of the European pharmacopeia (EuPh) 2.8.23 “Microscopic examination of the medicinal plant raw material”. The macroscopic studies were performed using a magnifying glass and a MBS-9 binocular microscope, the microscopic studies were done using MS Microscopes 10 (oculars X5, X10, X15, lenses x10,x40), Micromed XS-4130 (oculars WF15X, lenses x40/0.65, x10/0.25) with a microphotonozzle (China). Identification of the main substances was carried out by the TLC method, testing and the quantitative determination of the flavonoid content were performed according to the EuPh methods.Results and discussion. Morphological and anatomical features of the A. nivea herb have been determined; on their basis Identifications A and B have been proposed; TLC Identification C of the main BAS of the raw material has been developed; indicators of purity tests have been determined. It has been proposed to carry out the quantitative determination by the content of flavonoids.Conclusions. The parameters of the A. nivea herb standardization have been determined on the basis of the following indicators: macroscopic and microscopic features, TLC identification of the main BAS of the raw material (hyperoside, rutin, quercetin and chlorogenic acid), related impurities (not more than 2 %), stems with a diameter of more than 20 mm (not more than 10 %), the loss on drying (not more than 13 %), the total ash (not more than 10 %) and at least 0.5 % flavonoids calculated with reference to rutin. Флора Казахстану багата на перспективні маловивчені рослини, які застосовують у народній медицині, але для їх впровадження в медичну практику потрібні додаткові глибокі дослідження, за допомогою сучасних наукових методів. Цікавим об’єктом для впровадження в офіцинальну медичну та фармацевтичну практику є Альфредія снігова (Alfredia nivea KAR. & KIR.) родини Asteraceae, яку в народній медицині використовують як нейротропний засіб.Мета. Для створення нових лікарських засобів на основі трави Альфредії снігової необхідно розробити методи контролю якості цієї сировини, тому метою досліджень було визначити параметри стандартизації трави A. nivea KAR. & KIR.Матеріали та методи. Об’єктами дослідження були зразки трави Альфредії снігової (A. nivea), заготовлені в Кунгей Алатау, за 4,3 км південно-східніше від с. Карабулак, ущ. Східний Карабулак, Алматинської області, Казахстан. Макро- і мікроскопічні дослідження трави Альфредії снігової виконували згідно з методикою Європейської фармакопеї (ЄФ) 2.8.23 «Мікроскопічне дослідження лікарської рослинної сировини». Для макроскопічних досліджень використовували лупу та бінокулярний мікроскоп МБС-9, для мікроскопічних – мікроскопи МС 10 (окуляр х5, х10, х15, об’єктиви х10, x40), Micromed XS-4130 (окуляр WF15X, об’єктиви х40/0,65, х10/0,25) з мікрофотонасадкою (КНР). Ідентифікували основні речовини методом ТШХ, випробування та кількісне визначення за вмістом флавоноїдів здійснювали відповідно до методик ЄФ.Результати та їх обговорення. Визначено морфологічні й анатомічні ознаки трави Альфредії снігової, на основі яких запропоновано ідентифікації А та В, розроблено ТШХ ідентифікацію С основних БАР сировини, визначено показники випробувань на чистоту, а також запропоновано проводити кількісне визначення за вмістом флавоноїдів.Висновки. Визначено параметри стандартизації трави Альфредії снігової за такими показниками: макро- та мікроскопічні ознаки, ТШХ ідентифікація основних БАР сировини (гіперозид, рутин, кверцетин та хлорогенова кислота), сторонні домішки (не більше 2 %), наявність стебел діаметром понад 20 мм (не більше 10 %), втрата в масі під час висушування (не більше 13 %), загальна зола (не більше 10 %) і не менше 0,5 % флавоноїдів у перерахунку на рутин. National University of Pharmacy 2023-06-03 Article Article application/pdf https://ophcj.nuph.edu.ua/article/view/276004 10.24959/ophcj.23.276004 Journal of Organic and Pharmaceutical Chemistry; Vol. 21 No. 1 (2023); 46-53 Журнал органической и фармацевтической химии; Том 21 № 1 (2023); 46-53 Журнал органічної та фармацевтичної хімії; Том 21 № 1 (2023); 46-53 2518-1548 2308-8303 en https://ophcj.nuph.edu.ua/article/view/276004/273040 Copyright (c) 2023 Almat G. Rustemkulov, Tetiana M. Gontova, Balzhan G. Makhatova, Aisana E. Rustemkulova, Ubaidilla M. Datkhayev, Oleh M. Koshovyi http://creativecommons.org/licenses/by/4.0
spellingShingle Альфредія снігова
Alfredia nivea
трава
стандартизація
методи контролю якості
Rustemkulov, Almat G.
Gontova, Tetiana M.
Makhatova, Balzhan G.
Rustemkulova, Aisana E.
Datkhayev, Ubaidilla M.
Koshovyi, Oleh M.
Параметри стандартизації трави Alfredia nivea KAR.&KIR.
title Параметри стандартизації трави Alfredia nivea KAR.&KIR.
title_alt Standardization Parameters of Alfredia nivea KAR.&KIR Herb
title_full Параметри стандартизації трави Alfredia nivea KAR.&KIR.
title_fullStr Параметри стандартизації трави Alfredia nivea KAR.&KIR.
title_full_unstemmed Параметри стандартизації трави Alfredia nivea KAR.&KIR.
title_short Параметри стандартизації трави Alfredia nivea KAR.&KIR.
title_sort параметри стандартизації трави alfredia nivea kar.&kir.
topic Альфредія снігова
Alfredia nivea
трава
стандартизація
методи контролю якості
topic_facet Альфредія снігова
Alfredia nivea
трава
стандартизація
методи контролю якості
Alfredia nivea
herb
standardization
quality control methods
url https://ophcj.nuph.edu.ua/article/view/276004
work_keys_str_mv AT rustemkulovalmatg standardizationparametersofalfredianiveakarampkirherb
AT gontovatetianam standardizationparametersofalfredianiveakarampkirherb
AT makhatovabalzhang standardizationparametersofalfredianiveakarampkirherb
AT rustemkulovaaisanae standardizationparametersofalfredianiveakarampkirherb
AT datkhayevubaidillam standardizationparametersofalfredianiveakarampkirherb
AT koshovyiolehm standardizationparametersofalfredianiveakarampkirherb
AT rustemkulovalmatg parametristandartizacíítravialfredianiveakarampkir
AT gontovatetianam parametristandartizacíítravialfredianiveakarampkir
AT makhatovabalzhang parametristandartizacíítravialfredianiveakarampkir
AT rustemkulovaaisanae parametristandartizacíítravialfredianiveakarampkir
AT datkhayevubaidillam parametristandartizacíítravialfredianiveakarampkir
AT koshovyiolehm parametristandartizacíítravialfredianiveakarampkir