RESUMEN
Phytochemical study on the roots of a medicinal plant Ferula communis L. (Apiaceae) resulted in the isolation of 20 sesquiterpenes including 12 previously undescribed compounds, dauferulins A-L (1-12). The detailed spectroscopic analysis revealed 1-12 to be daucane-type sesquiterpenes with a p-methoxybenzoyloxy group at C-6. The absolute configurations of 1-12 were deduced by analysis of the ECD spectra. Dauferulins A-L (1-12), known sesquiterpenes (13-20), and analogues (14a-14l) derived from 6-O-p-methoxybenzoyl-10α-angeloyloxy-jeaschkeanadiol (14) were evaluated for their effects on AMPK phosphorylation in human hepatoma HepG2 cells as well as inhibitory activities against erastin-induced ferroptosis on human hepatoma Hep3B cells and IL-1ß production from LPS-treated murine microglial cells.
Asunto(s)
Carcinoma Hepatocelular , Ferula , Neoplasias Hepáticas , Sesquiterpenos , Humanos , Animales , Ratones , Ferula/química , Carcinoma Hepatocelular/tratamiento farmacológico , Estructura Molecular , Sesquiterpenos/química , Raíces de Plantas/químicaRESUMEN
Formohyperins A-F, previously undescribed meroterpenes, and grandone, a prenylated benzoylphloroglucinol being considered to be one of their biogenetic precursors, were isolated from the flowers of a Hypericaceous plant, Hypericum formosanum Maxim. Detailed spectroscopic analyses showed that formohyperins A-D were meroterpenes with an enolized 3-phenylpropane-1,3-dione moiety. Formohyperins E and F were elucidated as meroterpenes having a 4-benzoyl-5-hydroxycyclopent-4-ene-1,3-dione moiety. Formohyperins A-C and E were optically active, and their absolute configurations were deduced by comparison of the experimental and TDDFT calculated ECD spectra. In contrast, formohyperin D was concluded to be a racemate. Formohyperins A-F and grandone were found to show inhibitory activities against LPS-stimulated IL-1ß production from murine microglial cells with EC50 values of 13.2, 6.6, 8.5, 24.3, 4.1, 10.9, and 3.0 µM, respectively.
Asunto(s)
Hypericum , Floroglucinol , Ratones , Animales , Floroglucinol/farmacología , Floroglucinol/química , Hypericum/química , Flores , Microglía , Prenilación , Estructura MolecularRESUMEN
Phytochemical study on the whole plants of a Gentianaceous medicinal plant, Canscora lucidissima, gave one new acylated iridoid glucoside, canscorin A (1), and two new xanthone glycosides (2 and 3) together with 17 known compounds including five xanthones, eight xanthone glycosides, two benzophenone glucosides, caffeic acid, and loganic acid. Canscorin A (1) was assigned as a loganic acid derivative having a hydroxyterephthalic acid moiety by spectroscopic analysis together with chemical evidence, while 2 and 3 were elucidated to be a rutinosylxanthone and a glucosylxanthone, respectively. The absolute configurations of the sugar moieties of 2 and 3 were determined by HPLC analysis. The isolated compounds were evaluated for their inhibitory activities against erastin-induced ferroptosis on human hepatoma Hep3B cells and LPS-stimulated IL-1ß production from murine microglial cells.
Asunto(s)
Ferroptosis , Gentianaceae , Xantonas , Ratones , Humanos , Animales , Glucósidos Iridoides , Estructura Molecular , Glicósidos/farmacología , Glicósidos/química , Xantonas/farmacologíaRESUMEN
Three new farnesylated coumarins, communiferulins A-C (1-3), and a farnesylated chromone, ferchromone (4), were isolated from the roots of an Apiaceous plant Ferula communis. Their structures including the relative configurations were elucidated by a combination of spectroscopic analyses and calculations of the NMR data. Communiferulins A-C (1-3) had dihydrofuran rings fused to C-3 and C-4 of their coumarin moieties, while 3 possessed one additional furan ring. HPLC analyses using a chiral column showed 1-4 to be racemates, and the absolute configurations of (+)-1, (-)-1, (+)-2, and (-)-2 were deduced by comparison of their ECD spectra with TDDFT-calculated spectra. Communiferulins A (1) and B (2), and ferchromone (4) showed inhibitory activities on IL-1ß production from LPS-stimulated microglial cells.
Asunto(s)
Ferula , Ferula/química , Estructura Molecular , Extractos Vegetales/química , Espectroscopía de Resonancia Magnética , Cumarinas/farmacología , Cumarinas/química , Raíces de Plantas/químicaRESUMEN
Two new guaianolide sesquiterpenes, lanicepines A (1) and B (2), possessing unusual amino acid-derived substituents at C-13, were isolated from the flowering aerial parts of Saussurea laniceps, a traditional herbal medicine also known as "snow lotus". The structures of 1 and 2 were elucidated based on spectroscopic analysis including applications of the modified Mosher's method and Marfey's method as well as ECD calculations. Lanicepine A (1) contains a dihydropyridinone moiety with a carbamoyl and a hydroxymethyl group. This substituent was considered to consist of asparagine and a C4 unit. In contrast, lanicepine B (2) has a substituent that seems to be derived from l-proline and a C4 unit. Lanicepines A (1) and B (2) and two related known sesquiterpenes isolated from the same plant material, 11ß,13-dihydrodesacylcynaropicrin (3) and 11ß,13-dihydrodesacylcynaropicrin 8-O-ß-d-glucoside (4), demonstrated inhibitory activity against IL-1ß production from LPS-stimulated microglial cells.
Asunto(s)
Saussurea , Sesquiterpenos , Aminoácidos/análisis , Estructura Molecular , Componentes Aéreos de las Plantas/química , Saussurea/química , Sesquiterpenos/química , Sesquiterpenos de Guayano/químicaRESUMEN
Six dibenzo-1,4-dioxane derivatives (1-6) were isolated from the roots of a Hypericaceous plant Hypericum ascyron. Spectroscopic analyses revealed 2 and 4-6 to be new compounds. The partial racemic natures of 1-3 were concluded by chiral HPLC analyses, while 5 was confirmed to be a racemate. The absolute configurations 1-4 were deduced on the basis of ECD calculations. Biological activity evaluation of the dibenzo-1,4-dioxane derivatives along with two related compounds: hyperdioxanes A (7) and B (8), previously isolated from the same plant material by our group demonstrated that 7 exhibit an anti-HIV activity (IC50 5.3 µM, TI 7.2) while 8 showed an inhibitory effect on IL-1ß production (inhibition rate: 72.3% at 6.3 µM) from LPS-stimulated microglial cells.
Asunto(s)
Hypericum , Dioxanos , Estructura Molecular , Raíces de PlantasRESUMEN
Phytochemical study on a non-medicinal part of a plant material for herbal medicine, the roots of Schisandra chinensis, was conducted to isolate five new triterpenes, schinensins A-D (1-4) and 3-O-methylchangnanic acid (5), together with 21 known compounds including 10 triterpenes, one sterol, two sesquiterpenes, seven lignans, and one flavonoid. The structures of new triterpenes (1-5) were assigned on the basis of spectroscopic analyses aided with TDDFT ECD calculations. Schinensin A (1) was a dinortriterpene possessing 28-norschiartane skeleton, while schinensins B-D (2-4) were assigned as 3,4:9,10-disecocycloartane, 3,4-secocycloartane, and cycloartane triterpenes, respectively. In an evaluation of antiproliferative activities against human cancer cell lines, some triterpenes exhibited significant activities against human breast carcinoma MCF-7 cells as compared to the other cell lines (A549, HeLa, and RPMI8226).
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Schisandra/química , Triterpenos/farmacología , Antineoplásicos Fitogénicos/aislamiento & purificación , Humanos , Japón , Lignanos , Células MCF-7 , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Raíces de Plantas/química , Sesquiterpenos , Triterpenos/aislamiento & purificaciónRESUMEN
Phytochemical investigation on the aerial parts of a Lamiaceous medicinal plant Perovskia scrophulariifolia collected in Uzbekistan resulted in the isolation of two new 20-norabietane diterpenes, along with thirteen known diterpenes including one 20-norabietane, eight abietanes, one 6,7-secoabietane, and three icetexanes. The structures of new 20-norabietane diterpenes, perovsfolins C (1) and D (2), were elucidated by spectroscopic analyses aided with calculations of ECD spectra. Perovsfolin C (1) is the first 20-norabietane diterpene possessing a 1,11-epoxy moiety, while perovsfolin D (2) is a 20-norabitetane diterpene with a 2-hydroxy-1,4-quinone moiety as C-ring. Anti-neuroinflammatory activity of the isolated diterpenes on microglial cells was evaluated.
Asunto(s)
Antiinflamatorios/farmacología , Diterpenos/farmacología , Microglía/efectos de los fármacos , Salvia/química , Abietanos/aislamiento & purificación , Abietanos/farmacología , Antiinflamatorios/aislamiento & purificación , Células Cultivadas , Diterpenos/aislamiento & purificación , Humanos , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Componentes Aéreos de las Plantas/química , Plantas Medicinales/química , UzbekistánRESUMEN
Structurally unique C28 terpenoids, perovsfolins A (1) and B (2), were isolated from the aerial parts of an Uzbek medicinal plant, Perovskia scrophulariifolia (Lamiaceae). Their chemical structures including an unprecedented 6/8/6/6/6 pentacyclic carbon skeleton with a C6-C3 ester moiety were elucidated on the basis of spectroscopic analyses aided by density functional theory calculations as well as chemical evidence. Perovsfolin B (2) exhibited an anti-neuroinflammatory activity.
Asunto(s)
Antiinflamatorios/farmacología , Componentes Aéreos de las Plantas/química , Extractos Vegetales/química , Salvia/química , Terpenos/farmacología , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Estructura Molecular , Plantas Medicinales , Terpenos/química , Terpenos/aislamiento & purificaciónRESUMEN
Five new abietane diterpenes, lophachinins A-E (1-5), and eleven known related diterpenes were isolated from a Mongolian traditional herbal medicine, the aerial parts of Lophanthus chinensis (Lamiaceae). The structures of new diterpenes were assigned by spectroscopic analyses. Lophachinins A (1) and B (2) were abietane diterpene possessing an endoperoxy bridge at C-ring. In contrast, lophachinins C-E (3-5) had an abietane skeleton with an aromatized C-ring. The absolute configuration of 1 was elucidated by application of the modified Mosher's method, while those of 2, 3, and 5 were assigned by chemical conversions. The absolute configuration of lophachinin D (4) was deduced by ECD calculation. Anti-inflammatory activity of isolated diterpenes on microglial cells were evaluated.
Asunto(s)
Abietanos/farmacología , Antiinflamatorios/farmacología , Diterpenos/farmacología , Lamiaceae/química , Abietanos/aislamiento & purificación , Antiinflamatorios/aislamiento & purificación , Línea Celular Tumoral , Diterpenos/aislamiento & purificación , Humanos , Medicina Tradicional de Asia Oriental , Microglía/efectos de los fármacos , Estructura Molecular , Mongolia , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Componentes Aéreos de las Plantas/químicaRESUMEN
Four previously undescribed acylated iridoid glucosides, linaburiosides AâD, one undescribed iridoid, 7-deoxyiridolactonic acid, and one known acylated iridoid glucoside, iridolinarin C, were isolated from the aerial parts of a Mongolian traditional herbal medicine, Linaria buriatica. Linaburiosides AâD had an acyl moiety corresponding to 7-deoxyiridolactonic acid. Detailed spectroscopic analyses of linaburiosides AâD and 7-deoxyiridolactonic acid led to the assignment of their structures. The absolute configuration of 7-deoxyiridolactonic acid was elucidated by application of the PGME method; those of linaburiosides AâD were assigned on the basis of chemical conversions, as well as application of the modified Mosher's method. The absolute configuration of iridolinarin C was also elucidated in this study. Anti-inflammatory and antiproliferative activities of isolated compounds and their derivatives were evaluated.
Asunto(s)
Antiinflamatorios/farmacología , Glucósidos/farmacología , Iridoides/farmacología , Linaria/química , Fitoquímicos/farmacología , Células A549 , Acilación , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Glucósidos/química , Glucósidos/aislamiento & purificación , Humanos , Interleucina-1beta/antagonistas & inhibidores , Interleucina-1beta/biosíntesis , Iridoides/química , Iridoides/aislamiento & purificación , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Células MCF-7 , Microglía/efectos de los fármacos , Microglía/metabolismo , Conformación Molecular , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Células Tumorales CultivadasAsunto(s)
Enfermedades por Almacenamiento Lisosomal del Sistema Nervioso/genética , Enfermedades por Almacenamiento Lisosomal del Sistema Nervioso/terapia , 1-Desoxinojirimicina/análogos & derivados , 1-Desoxinojirimicina/uso terapéutico , Animales , Antiinflamatorios no Esteroideos/uso terapéutico , Aspirina/uso terapéutico , Trasplante de Médula Ósea , Modelos Animales de Enfermedad , Proteína Activadora de G (M2)/genética , Terapia Genética , Humanos , Mutación , beta-N-Acetilhexosaminidasas/genéticaRESUMEN
Four new guaianolides, sinodielides E-H (1-4), were isolated from the root of Sinodielsia yunnanensis WOLFF. Their structures were established by spectral evidence.
Asunto(s)
Plantas Medicinales/química , Sesquiterpenos de Guayano/química , China , Espectroscopía de Resonancia Magnética , Extractos Vegetales/química , Raíces de Plantas/química , Espectrofotometría Infrarroja , Espectrofotometría UltravioletaRESUMEN
Four new guaianolides, sinodielides A-D (1-4), were isolated from Sinodielsia yunnanensis WOLFF together with a known polyacetylene, falcarindiol, and two known coumarins, bergapten and scopoletin. Their structures were established by spectral and X-ray analyses.