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Project №АР05134198 «The Study of the Biosynthesis of Terpenoids In Project №АР05134198 «The study of the biosynthesis January – December 2019 of terpenoids in plants and the search for new pharmacologically active bimolecular compounds» In 2019, the Research Institute of Biological Safety Problems took part in the implementation of this project. For chemical modification, sesquiterpenic lactones of Based on the isolated terpenoids, flavonoids and alkaloids, For the reporting period, an application was filed for a grossheimin from Chartolepis intermedia Boiss., arglabin new hybrid derivatives were synthesized for the first time: receiving of protection document 2019/0611.1 dated and argolide from the CO2 extract of Artemisia glabella Kar. quercetinylgrossheimin (according to the Heck reaction) and 22.08.2019. Hydrochloride 3-oxo-8α-hydroxy-1,5,7α, et Kir., flavonoids pinostrobin from an alcoholic extract of β-cytisinylgrossheimin (according to the Michael reaction). 4,6,8,11β(H)-guaia-10(14)en-11(13-cytisinyl)-12,6-olide, Populus balsamifera L. buds and quercetin from an alcoholic Based on sesquiterpene lactones arglabin and grossheimin, which has an anthelmintic activity. extract of Hypericum perforatum L. were isolated and 4 of their new cytisinyl and anabasinyl derivatives were accumulated. synthesized. Grossmizin oxime was developed as the initial synton for chemical modifications. Amounts of extractive substances were accumulated from 5 In experiments conducted at the Research Institute of 2 articles were published in peer-reviewed foreign journals species of plants (Artemisia santolinifolia Turcz. ex Besser, Biological Safety Problems (under agreement No. 48 of with impact factor: Ferula ovina Boiss., Ferula kelleri Koso-Pol., Ferula March 27, 2019), leaves and buds of Artemisia glabella Kar. Molecules. – 2019. – Vol. 24, No 350. – P. 1-18 .(Impact songarica Pall. ex Spreng, Handelia trichophylla (Schrenk.) et Kir. were determinated as terpenoid-containing organs. Factor according to Web of Science database 3.38); Heimerl). From the sum of extractives of Ferula kelleri Koso- Promising genes of syntheses GAS, GAO, and COS of the Expert Opinion on Therapeutic Patents. – 2019. - Vol. 29, Pol. the new natural compound 5-(1-ethoxyvinyl)-2-methyl- biosynthetic pathway of sesquiterpenic lactones were No 9. – P. 689-702 (Impact Factor according to Scopus benzene-1,3-diol was isolated and the structure of the its identified in them for the first time. A comparative analysis of database 1.318); molecule was established, and the ester of aromatic acid the obtained sequences in BLAST showed their high (more Abstracts of 3 reports in the collection of the XIII and terpenoid alcohol of the humulan structure, ferocinin, than 90%) identity with the genes of the enzymes of the International Symposium on the Chemistry of Natural was identified. From Artemisia santolinifolia Turcz. ex Besser GAS/GAO/COS module of other Asteraceae Compounds October 16-19, 2019, Shanghai, China and the coumarin scopoletin was isolated and identified, from representatives. Data on genes-"candidates" for GAS and International Scientific and Practical Conference “Actual Handelia trichophylla (Schrenk.) Heimerl - dimeric COS isolated from Artemisia glabella Kar. et Kir., will be Problems of Biodiversity and Biotechnology”, October 1, sesquiterpene lactone handelin. published in the Information Base of NCBI National Center 2019. for Biotechnological Information (USA). The structure of the isolated compounds and synthesized According to the results of bioscreening, α- * JSC International Research and Production Holding new derivatives was established on the basis of the data of cytisinylgrossheimin hydrochloride is a promising compound “Phytochemistry”, under the Agreement with the Committee of Science of the MES RK No. 79 dated March 2, 2018, implements grant projects IR-, UV-, 1H, 13C NMR spectroscopy and X-ray diffraction for an in-depth study of its anthelmintic activity. for 2018-2020 in priority areas "Science of Life and Health" and analysis. "Rational use of natural, including water resources, geology, processing, new materials and technologies, safe products and structures“ Project №АР05133096 «Pharmacognostic research of January – December 2019 plants and taxon chemosystematics of the Asteraceae family» Co-executing organizations took part in the implementation of this project: Institute of Botany and Phytointroduction and the Central Siberian Botanical Garden of the SB RAS. A comparative analysis of the anatomical and morphological Together with the Central Siberian Botanical Garden of the Locations of growth have been identified and operational and diagnostic features, as well as the results of SB RAS (under Agreement No. 57 of April 10, 2019) and the reserves of Artemisia annua L. have been assessed in the histochemical studies of 6 species of plants of the subgenus Institute of Botany and Phytointroduction (under Agreement villages of Uzynagash, Shilikbai of Zhambyl district, in the Artemisia Less (Artemisia absinthium L., Artemisia annua L., No. 55 of April 01, 2019), a comparative analysis of vicinity of the villages of Sayan, Kainar and Kaskelen of the Artemisia frigida Willd., Artemisia rupestris L., Artemisia anatomical and morphological and diagnostic features as Karasai district, in the villages of Akshi, Avat, Turgen and sieversiana Ehrh. Ex Willd., Artemisia santolinifolia Turcz. ex well as the results of histochemical studies of 5 species of Enbek of Enbekshikazakhskyi district of Almaty region. Besser.) was carried out. Differences were revealed in the plants of the subgenus Dracunculus (Bess.) Rydb. The integrity of plant raw materials was determined, shape of the stem, leaves, the number and structure of (Artemisia dracunculus L., Artemisia quinqueloba Trautv., merchandising parameters of plants of the genus Artemisia L conducting bundles, pubescence (presence or absence, type Artemisia marschalliana Spreng., Artemisia scoparia Waldst. were established. of hairs), and the shape of epidermal cells, which are the & Kit., Artemisia tomentella Trautv.) was carried out. It was hallmarks of plant species. For the first time, the results of a revealed that the studied species differ in stem shape, leaf histochemical study on cross-sections of leaves and surface shape, number and structure of conducting bundles, preparations of flowers of the studied plants were obtained; pubescence (presence or absence, hair type), stomatal the presence of terpenoids and polyphenolic compounds apparatus type, form of epidermal cells. According to the was revealed. results of histochemical studies of cross-sections of leaves and surface preparations of flowers of the studied plants, the content of terpenoids, coumarins and polyphenolic compounds was determined. A pharmacognostic study and standardization of Peganum According to the results of the study of sesquiterpene For the reporting period, an application was filed for a patent harmala L. raw materials was carried out, an analytical lactones and coumarins of the species of subgenus of the Republic of Kazakhstan. Application No. 2019/0484.1 regulatory document “Peganum harmala, roots” was Artemisia Less. and Dracunculus (Bess.) Rydb., dated July 9, 2019 “Method for the obtaining of regenerated developed. representatives of these classes of natural compounds are plants Centaurea bipinnatifida (Trautv.) Tzvel.” defined as chemotaxonomic markers of studied taxa. 2 articles were published in journals Plant resources. – 2019. – Vol. 55, №3. – P.334-342 (impact factor RSCI - 0.331). News of the National Academy of Sciences of the Republic of Kazakhstan. Series of biology and medicine – 2019. - №2 - Р. 42-48 (according to Kazakhstan citation base 0,036). Project №АР05130476 «Technology of water-soluble January – December 2019 substances and finished dosage forms based on natural flavonoids and terpenoids» The effect of mechanochemical processing on the water A one-stage technology has been developed for producing a The technology for producing a complex of pinostrobin solubility of arglabin native substance was studied. An water-soluble substance of arglabin by mechanochemical oxime with disodium salt of glycyrrhizic acid and increase in the proportion of polysaccharide in a mixture of processing of arglabin native with an auxiliary substance - mechanocomposite of arglabin native with arglabin with arabinogalactan slightly increases the solubility polyvinylpyrrolidone, in a ball mill with a steel drum for 1 polyvinylpyrrolidone was optimized. of the mechanocomposite. It was found that during hour, in which the mechanocomposite of arglabin native mechanoprocessing, there is no disordering of the crystal dissolves within 20 minutes. structure of arglabin and its molecular dispersion in the polysaccharide matrix. Laboratory regulations have been developed and approved Experimental-industrial regulations for the production of For the reporting period, a conclusion was received from for the production of a complex of pinostrobin oxime with complex of pinostrobin oxime with disodium salt of 17.10.2019 on the grant of a patent of the Republic of disodium salt of glycyrrhizic acid LR-40761819-02-19 and a glycyrrhizic acid OPR FD65005037R-05-19 and Kazakhstan on the application 2018/053.1 dated 26.07.2018 mechanocomposite of arglabin native with mechanocomposite of arglabin native with "Method for producing a water-soluble substance based on polyvinylpyrrolidone LR-40761819-03-19. polyvinylpyrrolidone OPR FD65005037R-06-19 were pinostrobin oxime." developed and introduced into pharmaceutical
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