RESUMO
As part of our chemical studies on the medical plants in Uzbekistan aimed at searching for new drug leads, we have examined the aerial parts of Mediasia macrophylla. This has resulted in the isolation of four new glucosides, together with 30 known compounds. The structures of new compounds were elucidated as (1'S)-(4-hydroxyphenyl) ethane-1',2'-diol 2'-O-ß-glucopyranoside (1), 3-(4'-methoxyphenyl)-propanol 1-O-ß-glucopyranoside (2), 2-methoxy-3-hydroxy-5-(E)-propenyl-phenol 1-O-ß-glucopyranoside (3), 1-O-angeloyl-ß-glucopyranose (4), on the basis of spectral analysis.
Assuntos
Apiaceae/química , Glucosídeos/química , Componentes Aéreos da Planta/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , UzbequistãoRESUMO
Polyacetylenic glucosides (1-5) were isolated from the MeOH extract of Mediasia macrophylla, and their structures were established by spectroscopic analyses. Compounds 2-4 were the first examples of C(10)-polyacetylenic glucosides found in the family Umbelliferae, while compound 1 was a unique polyacetylenic glucoside possessing an alpha-pyrone moiety.
Assuntos
Alcinos/isolamento & purificação , Apiaceae/química , Glucosídeos/isolamento & purificação , Extratos Vegetais/química , Pironas/química , Alcinos/química , Glucosídeos/química , Estrutura Molecular , Componentes Aéreos da PlantaRESUMO
A new codonopsine-related alkaloid and 13 known compounds were isolated from the aerial parts of Codonopsis clematidea (Campanulaceae). The structure of the new compound was elucidated by two-dimensional nuclear magnetic resonance and other spectral examinations.
Assuntos
Alcaloides/isolamento & purificação , Anisóis/isolamento & purificação , Codonopsis/química , Componentes Aéreos da Planta/química , Pirrolidinas/isolamento & purificação , Alcaloides/química , Anisóis/química , Cromatografia Líquida de Alta Pressão , Espectroscopia de Ressonância Magnética , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Pirrolidinas/químicaRESUMO
Monoterpene glycosides (1-5, and 7), together with 14 known compounds, were isolated from the methanol extract of the roots of Paeonia hybrida. These compounds included a paeoniflorin-related glycoside with a hybrid structure of paeoniflorin and paeonovicinoside (1), a monoterpene glucoside biogenetically related to lactiflorin (2), a paeoniflorin-related monoterpene (3), arbiflorin-related monoterpenes (4 and 5), and a tymol-related monoterpene glycoside (7). Their structures were elucidated by extensive spectroscopic examinations.
Assuntos
Glicosídeos/isolamento & purificação , Paeonia/química , Terpenos/isolamento & purificação , Benzoatos/química , Hidrocarbonetos Aromáticos com Pontes/química , Glucosídeos/química , Glicosídeos/química , Espectroscopia de Ressonância Magnética , Medicina Tradicional Chinesa , Metanol/química , Estrutura Molecular , Monoterpenos , Raízes de Plantas/química , Terpenos/químicaRESUMO
The ethyl acetate-soluble fraction from a MeOH extract of the roots of Ferula varia gave six new sesquiterpene lactones (1-6) and five known sesquiterpenes (7-11). Their structures were established on the basis of spectroscopic evidence. The cytotoxic activities of 1-11 were evaluated against selected human cancer cell lines. Compound 4 showed significant selective cytotoxicity against multidrug-resistant cancer cells (KB-C2). The cytotoxicities of compounds 1, 3, 5, 8, and 11 against KB-C2 cells were enhanced in the presence of nontoxic concentrations of colchicine.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Ferula/química , Lactonas/isolamento & purificação , Lactonas/farmacologia , Plantas Medicinais/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Colchicina/análise , Colchicina/farmacocinética , Resistência a Múltiplos Medicamentos/efeitos dos fármacos , Resistencia a Medicamentos Antineoplásicos/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Células KB , Lactonas/química , Estrutura Molecular , Raízes de Plantas/química , Sesquiterpenos/química , UzbequistãoRESUMO
Two eudesmanes, two abietanes, two podocarpanes and other nine known compounds were isolated from the dried fruits of Juniperus polycarpus var. seravschanica. Their structures were established on the basis of analysis of spectroscopic evidence. Some of the isolated terpenoids showed antimalarial activity.
Assuntos
Juniperus/química , Terpenos/análise , Abietanos/análise , Abietanos/química , Abietanos/farmacologia , Animais , Antimaláricos/análise , Antimaláricos/química , Antimaláricos/farmacologia , Diterpenos/análise , Diterpenos/química , Diterpenos/farmacologia , Frutas/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/análise , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Plasmodium falciparum/efeitos dos fármacos , Plasmodium falciparum/crescimento & desenvolvimento , Sesquiterpenos/análise , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Sesquiterpenos de Eudesmano/análise , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacologia , Terpenos/química , Terpenos/farmacologiaRESUMO
Two new polyprenylated benzophenones, a new polyprenylated phloroglucinol, and six new xanthone derivatives were isolated from the aerial parts of the Uzbekistan medicinal plant Hypericum scabrum. Their structures were elucidated on the basis of spectroscopic evidence. The isolated compounds showed moderate cytotoxicity for human tumor cells.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Benzofenonas/isolamento & purificação , Hypericum/química , Plantas Medicinais/química , Xantonas/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Benzofenonas/química , Benzofenonas/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Células Tumorais Cultivadas , Uzbequistão , Xantonas/química , Xantonas/farmacologiaRESUMO
Two new stilbene derivatives, (E)-resveratrol 3-(6' '-galloyl)-O-beta-D-glucopyranoside (1) and (E)-resveratrol 3-(4' '-acetyl)-O-beta-D-xylopyranoside (2), and five known stilbene derivatives (3-7) were isolated from the dried aerial parts of Calligonum leucocladum. Their structures were established on the basis of spectroscopic evidence. Compound 1 showed antioxidant activity and a restorative effect of the inhibition of oxacillin to oxacillin/methicillin-resistant Staphylococcus aureus.
Assuntos
Glucosídeos/isolamento & purificação , Plantas Medicinais/química , Polygonaceae/química , Estilbenos/isolamento & purificação , Resistência a Múltiplos Medicamentos , Glucosídeos/química , Glucosídeos/farmacologia , Resistência a Meticilina , Estrutura Molecular , Oxacilina/farmacologia , Resveratrol , Staphylococcus aureus/efeitos dos fármacos , Estilbenos/química , Estilbenos/farmacologia , UzbequistãoRESUMO
The ethyl acetate soluble extract of the dried roots of Ferula penninervis gave 17 new sesquiterpenes [15 of the guaiane-type, ferupennins A-O (1-15), and two of the eudesmane-type, 1alpha-hydroxy-2-oxo-5alpha,7beta,11betaH-eudesm-3-en-6alpha,12-olide (16) and penninervin (17)] and nine known sesquiterpenes. The structures of the new compounds were elucidated on the basis of spectroscopic evidence and X-ray analysis. The absolute configuration of ferupennin A (1) was determined by a modified Mosher method.
Assuntos
Ferula/química , Plantas Medicinais/química , Sesquiterpenos/isolamento & purificação , Acetatos , Acetilação , Adulto , Cristalografia por Raios X , Ensaio de Imunoadsorção Enzimática , Humanos , Interleucina-1/sangue , Interleucina-2/sangue , Interleucina-4/sangue , Lipopolissacarídeos/farmacologia , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Raízes de Plantas/química , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Espectrofotometria Ultravioleta , Fator de Necrose Tumoral alfa/metabolismo , UzbequistãoRESUMO
The ethyl acetate-soluble fraction from a methanol extract of Ferula foetida has afforded six new sulfide derivatives, (E)-3-methylsulfinyl-2-propenyl sec-butyl disulfide (foetisulfide A) (1), (Z)-3-methylsulfinyloxy-2-propenyl sec-butyl disulfide (foetisulfide B) (2), (E)-3-methylsulfinyloxy-2-propenyl sec-butyl disulfide (foetisulfide C) (3), bis(3-methylthio-2E-propenyl) disulfide (foetisulfide D) (4), 3,4,5-trimethyl-2-thiophenecarboxylic acid (foetithiophene A) (5), 3,4,5-trimethyl-2-(methylsulfinyloxymethyl)thiophene (foetithiophene B) (6), along with six known compounds. The structures of 1-6 were established on the basis of spectroscopic studies, with the elucidation of 5 confirmed by single-crystal X-ray crystallography.
Assuntos
Ferula/química , Plantas Medicinais/química , Sulfetos/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Cristalografia por Raios X , Medicina Tradicional , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Raízes de Plantas/química , Estereoisomerismo , Sulfetos/química , Tiofenos/química , Tiofenos/isolamento & purificação , UzbequistãoRESUMO
An unusual new sesquiterpene derivative, kuhistaferone (1), was isolated from the fruits of the Uzbekistan medicinal plant Ferula kuhistanica. The structure of 1 was established on the basis of spectroscopic evidence. Compound 1 showed moderate cytotoxicity against the human colon tumor cell line HCT116.
Assuntos
Antibacterianos/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Ferula/química , Plantas Medicinais/química , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Antibacterianos/química , Antibacterianos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Neoplasias do Colo , Ensaios de Seleção de Medicamentos Antitumorais , Frutas/química , Humanos , Concentração Inibidora 50 , Meticilina/farmacologia , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Células Tumorais Cultivadas/efeitos dos fármacos , UzbequistãoRESUMO
Nine new polyprenylated benzoylphloroglucinol derivatives, hyperibones A-I (1-9), were isolated from the aerial parts of the Uzbekistan medicinal plant Hypericum scabrum. Their structures were determined mainly on the basis of spectroscopic evidence (2D NMR and HRMS). Compounds 1, 2, and 4 showed mild in vitro antibacterial activity against methicillin-resistance Staphylococus aureus (MRSA) and methicillin-sensitive Staphylococus aureus (MSSA).
Assuntos
Antibacterianos/isolamento & purificação , Hypericum/química , Resistência a Meticilina/fisiologia , Floroglucinol/análogos & derivados , Floroglucinol/isolamento & purificação , Plantas Medicinais/química , Staphylococcus aureus/efeitos dos fármacos , Antibacterianos/química , Antibacterianos/farmacologia , Cromatografia Líquida de Alta Pressão , Resistência Microbiana a Medicamentos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Floroglucinol/química , Floroglucinol/farmacologia , Espectroscopia de Infravermelho com Transformada de Fourier , UzbequistãoRESUMO
The n-hexane and ethyl acetate extracts of the stems and the ethyl acetate extracts of roots from Prangos pabularia afforded an gamma-pyrone derivative and furanocoumarin derivatives with three glucose and gamma-pyrone (pabularin A, B and C), along with 26 previously known compounds (18 coumarins, six terpenoids and two glycosides). Their structures were established on the basis of spectroscopic studies. Of these, 16 coumarin derivatives isolated from P. pabularia were tested for antibacterial activity and inhibition of cytokine release.