This experiment focused on investigating the chemical constituents of the plant Artemisia porrecta Krasch.ex Poljakov, resulting in the isolation and characterization of twenty-seven sesquiterpene lactones belonging to the eudesmanolides, germacronolides, melampolides, and heliangolide types. These compounds include ten undescribed sesquiterpene lactones, Porrectolide A-I, 11-epi-Deacetylherbolide D and seventeen known ones. All known compounds were isolated from this plant for the first time. Their structures were established by 1D, 2D NMR spectroscopic and HR-ESI-MS data, electronic circular dichroism, and single crystal X-ray diffraction analysis. Evaluations of the anti-inflammatory activity revealed that 6 had moderate anti-inflammatory activity on lipopolysaccharide-induced nitric oxide production in RAW264.7 cells with the IC50 value of 14.57 ± 0.24 μM.
A new flavonol glycoside that was called rosanoside was isolated from the aerial part of the plant Oxytropis rosea. Its structure was established by analyzing data from 1H and 13C NMR spectra and DEPT, HSQC, and HMBC experiments. Rosanoside had the structure rhamnocitrin-3-O-(6′′-crotonoyl-β-D-glucopyranoside).
A new compound, 5β,6β-epoxy-20α,24β,25α-trihydroxy-1,3-dioxowitha-2-enolide (1), and two known compounds, gracillin (2) and 5α-hydroxylaxogenin (3), have been isolated from the aerial part of Saponaria officinalis. High-resolution mass spectrometry and 1D and 2D NMR spectroscopy analysis data were used to establish the structure of the new compound. The antimicrobial activity of the new compound against some opportunistic strains of microorganisms and its cytotoxicity against two cancer cell lines and two healthy cell lines in vitro were studied. 5β,6β-Epoxy-20α,24β,25α-trihydroxy-1,3-dioxowitha-2-enolide was found to be most active against three bacterial strains: Staphylococcus aureus, Bacillus subtilis, and Pseudomonas aeruginosa, with inhibition zone diameters of 21.04 ± 0.10 mm, 22.08 ± 0.12 mm, and 18.12 ± 0.13 mm, respectively. Compound 1 also showed significant cytotoxicity against HEp-2 and HeLa cell lines (IC50 = 23.2 μM and 54.9 μM, respectively).
New amides of 3- O -acetyl-18 β - H -glycyrrhetic acid with several aromatic and heterocyclic amines were synthesized. The chemical structures of the synthesized compounds were elucidated by UV, IR and NMR spectroscopic and mass spectrometric methods.
Экстракт, полученный из надземной части Datura stramonium обработкой 90 %-ным этиловым спиртом, фракционировали различными органическими растворителями. При использовании экстракционного бензина получили 0,28 % экстрактивных веществ, хлороформа — 2,24 %, этилацетата — 1,19 %, н-бутанола — 12,43 % к массе сырья. Шесть витанолидов, такие как датуралактон (I), (22R)-7α,27-гидрокси-1-оксовита-2,5,24-триенолид (II), датурататурин А (III), витастрамонолид (IV), (22R)-27-гидрокси-7α-метокси-1-оксовита-3,5,24-триенолид (V) и датураметелин Н (VI) выделены из надземной части Datura stramonium, который был собран в Ферганской области Республики Узбекистан. Их структура была выяснена на основе обширных ИК-, УФ- и ЯМР-спектроскопических исследований. Доказано наличие веществ II, III, V в надземной части Datura stramonium, произрастающего в Узбекистане, а вещество VI впервые выделено из надземной части Datura stramonium. Изучена цитотоксичность химически чистого датураметелина H на линиях раковых клеток, таких как эпителиальная карцинома шейки матки HeLa, аденокарцинома молочной железы HBL-100 (АТСС НТВ 124), аденокарцинома гортани HEp-2 (ATCC:CCL-23), T-лимфобластная лейкемия CCRF-CEM (ATCC:CCL-19), и установлено, что он проявляет выраженную цитотоксичность в концентрации 100 мкМ лишь в отношении клеток T-лимфобластной лейкемии in vitro.
The new alkaloid lindelofamine N-oxide (1) and the known 1-exo-carboxypyrrolizidine (2) and the quaternary salt of the isoquinoline alkaloid O-methylarmepavine methyliodide (3) were isolated from Lindelofia macrostyla (Bunge) Popov for the first time. The structures were established by NMR spectroscopy, the absolute configuration was determined using X-ray diffraction analysis of the chiral centers of the last two as 1R,4R,8S and 1S, respectively. The new carboxylic acid (2S,3R)-2-hydroxy-2-isopropyl-3-[(E)-2-methylbut-2-enoyl]oxybutanoic acid, the structure and absolute configuration (2S,3R) of which were proven by NMR spectroscopy and an XSA, was also isolated.
Polysaccharide constituents including water-soluble polysaccharides, pectic substances, and hemicelluloses were isolated from Datura stramonium L. (Solanaceae) leaves. Their monosaccharide compositions were established. The monomer compositions of the isolated biopolymers included neutral and acidic monosaccharides. Prebiotic activity was found for the water-soluble polysaccharides isolated by cold water.
The alkaloid composition of Rindera oblongifolia was studied, in which the pyrrolizidine alkaloids echinatine and trachelanthamine N-oxide, as well as two new quaternary salts namely rinderidine and the oblongifolidine were isolated. The structures of the isolated new alkaloids were elucidated by NMR spectroscopy. The absolute configuration of lindelofine, trachelanthamine N-oxide, rinderidine and oblongifolidine was established by single crystal X-ray diffraction as: 1 R, 4 R, 8 R, 2'S, 3'R; 1 R, 4S, 8S, 2'S, 3'R; 4 R, 7S, 8 R, 2'S, 3'S; 4 R, 7S, 8 R, 2'S, 3'S (7''S, 8''R) respectively. Both new pyrrolizidine alkaloids showed no cytotoxicity against four cancer cell lines such as HeLa, НEр-2, HBL-100 and CCRF-CEM.
The extract obtained from the aerial part of Datura stramonium by treatment with EtOH (90
The compositions of the essential oil and benzine fraction (F-1) of the EtOH extract of gum resin and starting gum resin of Ferula tadshikorum were studied using GC-MS and NMR spectroscopy. The main chemical constituents of these samples were shown to be a mixture of cis- and trans-1-propenyl 1-(methylthio)propyl disulfides with the cis-isomer quantitatively exceeding the trans-isomer in all samples. The results allowed GC-MS and NMR spectroscopy to be used to select the optimal method for extracting resins from F. tadshikorum to produce a giardicidal drug with reactive S-containing compounds and to standardize the resin extracted from F. tadshikorum collected in Uzbekistan.
New cytisine-thienopyrimidine hybrid molecules were synthesized by reacting cytisine with 4-chlorothieno [2,3- d ]pyrimidines in the presence of Et 3 N. The solvent effect on the course of the reaction was studied. The structures of the obtained compounds were elucidated using IR, 1 H and 13 C NMR spectroscopy and TLC-MS spectrometry. X-ray crystal structure analyses of the synthesized compounds were performed.
The new sesquiterpene lactone 11-epi-dehydroisoleucomisin was isolated from the aerial part of Artemisia juncea Kar. & Kir. Its structure and the absolute configurations of the chiral centers were established as 7R,8S,11S using a combination of mass spectrometry; IR, UV, and NMR spectroscopy; and an X-ray crystal structure analysis.
The new natural saponin 3β,16α-dihydroxy-23-oxo-oleanan-28,13β-olide (1) was isolated from the aerial part of Saponaria officinalis. Its structure was established by analyzing 1D and 2D NMR spectroscopic and high-resolution mass-spectrometric data. The antimicrobial activity of the new saponin against the microorganisms Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Candida albicans was studied.
The new natural phytoecdysteroid 20-hydroxyecdysone 25-O-benzoate (1) was isolated from the aerial parts of Silene popovii. The structure of the new compound was elucidated using 1D and 2D NMR and HPTLC-MS analyses.
The eudesmane-type sesquiterpene lactones 8α-hydroxyartemin, α-santonin, and 4,5α-epoxy-8α-hydroxy-6,8,11β(H)-eudesm-6,12-olide (8α-hydroxy-4α,5α-epoxytaurin) and the monoterpenoid p-menthane-1,2,4- triol were isolated for the first time from the EtOH extract of Artemisia ferganensis and chemically characterized. X-ray crystal structure analyses of the isolated sesquiterpene lactones established the absolute configurations of their chiral centers as 1R,5R,6S,7R,8S,10S,11S; 6S,7S,10S,11S; and 4R,5R,6S,7R,8S,10R,11S, respectively. The crystal and molecular structure of p-menthane-1,2,4-triol was found to correspond to the racemate of higher polarity without polymorphism in the crystal.