RESUMEN
Two new isocoumarin derivatives, eleuthemarins A (1) and B (2), were isolated from the Arctic fungus Eleutheromyces sp. CPCC 401592. Their structures and absolute configurations were elucidated through spectroscopic methods, quantum chemical calculations of NMR shifts, and calculated electronic circular dichroism. This is the first report for the chemical investigation of the genus Eleutheromyces. Compounds 1 and 2 showed selective cytotoxic activities against H460, A549, and HCT116 cancer cell lines with IC50 values in the range of 24.1-57.3 µM, respectively. Compound 1 displayed weak antibacterial activities.
Asunto(s)
Ascomicetos , Isocumarinas , Humanos , Isocumarinas/farmacología , Isocumarinas/química , Antibacterianos/química , Espectroscopía de Resonancia Magnética , Células HCT116 , Estructura MolecularRESUMEN
The crude extract of the Arctic fungus Phoma muscivora CPCC 401424 displayed anti-influenza A virus activities which led us to investigated their secondary metabolites. Four new chromone derivatives, phomarcticones A-D (1-4) and five known chromone analogs (5-9) have been isolated from Arctic fungus Phoma muscivora CPCC 401424. Compounds 3 and 4 possess rare sulfoxide groups in chromone derivatives. Their structures and absolute configurations were elucidated by extensive analysis of spectroscopic data, electronic circular dichroism, and comparison with reported data. Compounds 3, 7, and 9 showed significant anti-influenza A virus activities with the IC50 values of 24.4, 4.2, and 2.7 µM, respectively.
Asunto(s)
Antivirales , Cromonas , Antivirales/química , Cromonas/farmacología , Cromonas/química , Hongos , Dicroismo Circular , Estructura MolecularRESUMEN
Forsyqinlingines C (1) and D (2), two C9 -monoterpenoid alkaloids bearing a rare skeleton, were isolated from the ripe fruits of Forsythia suspensa. Their structures, including absolute configurations, were fully elucidated by extensive spectroscopic data and ECD experiments. The plausible biogenetic pathway for compounds 1 and 2 was also proposed. In vitro, two C9 -monoterpenoid alkaloids showed anti-inflammatory activity performed by the inhibitory effect on the release of ß-glucuronidase in rat polymorphonuclear leukocytes (PMNs), as well as antiviral activity against influenza A (H1N1) virus and respiratory syncytial virus (RSV).
Asunto(s)
Alcaloides/química , Antiinflamatorios/química , Antivirales/química , Forsythia/química , Monoterpenos/química , Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Animales , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Antivirales/aislamiento & purificación , Antivirales/farmacología , Forsythia/metabolismo , Frutas/química , Frutas/metabolismo , Glucuronidasa/metabolismo , Subtipo H1N1 del Virus de la Influenza A/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Conformación Molecular , Neutrófilos/citología , Neutrófilos/efectos de los fármacos , Neutrófilos/metabolismo , Factor de Activación Plaquetaria/farmacología , Ratas , Virus Sincitiales Respiratorios/efectos de los fármacosRESUMEN
Biotransformation of the neo-clerodane diterpene, scutebarbatine F (1), by Streptomyces sp. CPCC 205437 was investigated for the first time, which led to the isolation of nine new metabolites, scutebarbatine F1-F9 (2-10). Their structures were determined by extensive high-resolution electrospray ionization mass spectrometry (HRESIMS) and NMR data analyses. The reactions that occurred included hydroxylation, acetylation, and deacetylation. Compounds 2-4 and 8-10 possess 18-OAc fragment, which were the first examples of 13-spiro neo-clerodanes with 18-OAc group. Compounds 7-10 were the first report of 13-spiro neo-clerodanes with 2-OH. Compounds 1-10 were biologically evaluated for the cytotoxic, antiviral, and antibacterial activities. Compounds 5, 7, and 9 exhibited cytotoxic activities against H460 cancer cell line with inhibitory ratios of 46.0, 42.2, and 51.1%, respectively, at 0.3 µM. Compound 5 displayed a significant anti-influenza A virus activity with inhibitory ratio of 54.8% at 20 µM, close to the positive control, ribavirin.
RESUMEN
Five alkaloids, including two previously undescribed alkaloids, named forsyshiyanines A and B, attributable to the rare skeletons 4b,5,6,7,8,8a,9,10-octahydrobenzo[f]quinoline and (6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)methyl, respectively, along with three known ones (3-5), were isolated from the ripe fruits of Forsythia suspensa. The chemical structures including absolute configurations of two undescribed compounds were established using integrated spectroscopic techniques, electronic circular dichroism calculations, and single-crystal x-ray diffraction analysis. In vitro, five alkaloids showed anti-inflammatory activities, with the inhibition rates of the release of ß-glucuronidase from polymorphonuclear leukocytes of rats being in the range 47.9%-56.0% at a concentration of 10 µM. Moreover, five compounds exhibited anti-viral activities against influenza A virus and respiratory syncytial virus, with IC50 values in the range of 7.3-32.5 µM and EC50 values in the range 3.7-14.1 µM.
Asunto(s)
Alcaloides , Forsythia , Alcaloides/farmacología , Animales , Antiinflamatorios/farmacología , Antivirales/farmacología , Estructura Molecular , Ratas , EsqueletoRESUMEN
Two unique trinorlabdane diterpenoid alkaloids, forsyqinlingines A (1) and B (2), were isolated from the ripe fruits of Forsythia suspensa. Their structures, including absolute stereochemical configurations, were fully elucidated from extensive spectroscopy experiments, single-crystal X-ray diffraction, and electronic circular dichroism (ECD). In addition, a plausible biosynthetic pathway for the formation of compounds 1 and 2 in Forsythia suspensa was also proposed. In vitro, the two C17-labdane diterpenoid alkaloids exhibited anti-inflammatory activities by inhibiting the release of ß-glucuronidase in rat polymorphonuclear leukocytes (PMNs), and antiviral activities against influenza A (H1N1) virus and respiratory syncytial virus (RSV).
RESUMEN
Three new phenolic metabolites, daldispols A-C (1-3), two new chromone derivatives, (5R,7R)-5,7-dihydroxy-2-methyl-5,6,7,8-tetrahydro-4H-chromen-4-one (9) and (5R,7R)-5,7-dihydroxy-2-propyl-5,6,7,8-tetrahydro-4H-chromen-4-one (10), together with five known phenolic compounds (4-8) and two known chromone compounds (11 and 12) were isolated from the endolichenic fungus Daldinia sp. CPCC 400770. Their structures were elucidated on the basis of spectroscopic methods, electronic circular dichroism (ECD), and comparison with reported data. Compounds 1, 3, 4, 9, and 11 exhibited significant anti-influenza A virus (IAV) activities with IC50 values of 12.7, 6.4, 12.5, 16.1, and 9.0 µM, respectively, and compound 8 displayed significant anti-ZIKV activity with inhibitory ratio of 42.7% at 10 µM. The results demonstrated that the fungus Daldinia sp. CPCC 400770 might be a rich source for discovering anti-IAV secondary metabolites as potential novel leading compounds.
RESUMEN
Five previously undescribed labdane diterpenoids, named Forsypensins A-E, were isolated from the fruits of Forsythia suspensa. The structures and relative configurations of the compounds were elucidated via extensive spectroscopic methods, and their absolute configurations were fully confirmed by single crystal X-ray diffraction analyses using Cu Kα radiation and electronic circular dichroism data. The five labdane diterpenoids showed in vitro anti-inflammatory activity in rat polymorphonuclear leukocytes, inhibiting the rates of ß-glucuronidase release by 43.6%-49.2% at concentrations of 10 µM. The compounds also had anti-viral activity against influenza A (H1N1) virus and respiratory syncytial virus (RSV), with IC50 values in the range 21.8-27.4 µM, and EC50 values in the range 10.5-15.4 µM, respectively.
Asunto(s)
Diterpenos , Forsythia , Subtipo H1N1 del Virus de la Influenza A , Animales , Antiinflamatorios , Estructura Molecular , RatasRESUMEN
Eight labdane diterpenoids, including two new labdane diterpenoids, named forsyshiyanins A-B (2-3), along with six known ones (1, 4-8), were isolated from the fruits of Forsythia suspensa. The new structures including their absolute configurations were elucidated by extensive spectroscopic analyses, X-ray diffraction and computational calculation. In vitro, eight labdane diterpenoids showed anti-inflammatory activities, with the inhibition rates of release of ß-glucuronidase from polymorphonuclear leukocytes of rats being in the range 46.8-51.0% at concentrations of 10 µM, as well as anti-viral activities against influenza A (H1N1) virus and respiratory syncytial virus (RSV), with the IC50 values in the range 18.4-26.2 µM and EC50 values in the range 10.5-14.4 µM, respectively.
Asunto(s)
Antiinflamatorios/farmacología , Antivirales/farmacología , Diterpenos/farmacología , Forsythia/química , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Antivirales/química , Antivirales/aislamiento & purificación , Cristalografía por Rayos X , Diterpenos/química , Diterpenos/aislamiento & purificación , Perros , Frutas/química , Células Hep G2 , Humanos , Subtipo H1N1 del Virus de la Influenza A/efectos de los fármacos , Gripe Humana/tratamiento farmacológico , Células de Riñón Canino Madin Darby , Modelos Moleculares , Ratas , Infecciones por Virus Sincitial Respiratorio/tratamiento farmacológico , Virus Sincitiales Respiratorios/efectos de los fármacosRESUMEN
Diaphragma juglandis fructus is the dry wooden diaphragm inside walnuts and a byproduct in food processing of walnut kernels. The purpose of our research is to enrich the information on compounds in Diaphragma juglandis fructus to further discover and exploit its potential nutritional value. In this study, new quali-quantitative analytical approaches were developed to identify and determine bioactive compounds in Diaphragma juglandis fructus. Two-hundred compounds, including hydrolyzable tannins, flavonoids, phenolic acids, and quinones, were identified by UHPLC-Q-Orbitrap HRMS, more than 150 of which were first discovered in Diaphragma juglandis fructus. Among them, 21 major dietary polyphenols with health-promoting effects were successfully quantified using UHPLC-MS/MS, with total contents of 2.88-6.18 mg/g. This successful characterization and quantification of bioactive compounds in Diaphragma juglandis fructus gives a better understanding of its potential nutritional value and supports efficiently developing and reusing it instead of discarding it as agrofood waste.
Asunto(s)
Cromatografía Líquida de Alta Presión/métodos , Diafragma/química , Medicamentos Herbarios Chinos/química , Espectrometría de Masas en Tándem/métodos , Flavonoides/química , Frutas/química , Hidroxibenzoatos/química , Quinonas/químicaRESUMEN
Four undescribed flavonoid alkaloids, as two pairs of enantiomers, were initially isolated as a racemate from the whole plant of Scutellaria moniliorrhiza. By means of chiral HPLC, four isomers, named scumonilines A-D, were successfully separated, and their chemical structures including absolute configurations were established by mass as well as NMR spectroscopy and CD technique. In vitro, four flavonoid alkaloids showed anti-inflammatory activities, with IC50 values against the release of ß-glucuronidase from polymorphonuclear leukocytes of rats being in the range 5.16-5.85 µΜ. Moreover, four compounds were evaluated for their inhibitory activities against aldose reductase, and gave IC50 values in the range 2.29-3.03 µΜ.
Asunto(s)
Aldehído Reductasa/antagonistas & inhibidores , Alcaloides/farmacología , Antiinflamatorios no Esteroideos/farmacología , Inhibidores Enzimáticos/farmacología , Flavonoides/farmacología , Scutellaria/química , Aldehído Reductasa/metabolismo , Alcaloides/química , Alcaloides/aislamiento & purificación , Animales , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/aislamiento & purificación , Flavonoides/química , Flavonoides/aislamiento & purificación , Glucuronidasa/antagonistas & inhibidores , Glucuronidasa/metabolismo , Humanos , Estructura Molecular , Neutrófilos/efectos de los fármacos , Neutrófilos/metabolismo , Ratas , Relación Estructura-ActividadRESUMEN
Two new flavonoid glucuronate esters, named scuregeliosides A and B (1 and 2), as well as three known ones, chrysin-7-O-ß-d-glucuronic acid methyl ester (3), 5,7,4'-trihydroxyflavone-8-O-ß-d-glucuronic acid methyl ester (4) and apigenin-7-O-ß-d-glucuronic acid ethyl ester (5), were isolated from the ethanolic extract of the whole plant of Scutellaria regeliana. Their chemical structures were elucidated on the basis of comprehensive spectroscopic analyses. Five compounds were screened for anti-inflammatory activity in vitro. As the results, the inhibition rates of release of ß-glucuronidase from rat polymorphonuclear leukocytes were in the range of 42.2 - 47.1% at a concentration of 10 µm.
Asunto(s)
Antiinflamatorios no Esteroideos/farmacología , Ésteres/farmacología , Flavonoides/farmacología , Glucuronatos/farmacología , Glucuronidasa/antagonistas & inhibidores , Glicoproteínas/farmacología , Scutellaria/química , Animales , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/aislamiento & purificación , Ésteres/química , Ésteres/aislamiento & purificación , Flavonoides/química , Flavonoides/aislamiento & purificación , Glucuronatos/química , Glucuronatos/aislamiento & purificación , Glucuronidasa/metabolismo , Glicoproteínas/química , Glicoproteínas/aislamiento & purificación , Estructura Molecular , Neutrófilos/enzimología , RatasRESUMEN
By means of preparative HPTLC and column chromatography over silica gel and Sephadex LH-20, nineteen flavonoids were isolated and purified from the whole plants of Scutellaria moniliorrhiza. Based on the physico-chemical properties and spectral data, their structures were identified asï¼ apigenin (1), luteolin (2), wogonin (3), oroxylin A (4), 6-methoxynaringein (5), 5,7,4'-trihydroxy-6,8-dimethoxyflavone (6), 5,7,8-trimethoxyflavone (7), 3,5,6,7-tetramethoxyflavone (8), 7-hydroxy-4',5,6,8-tetramethoxyflavone (9), 5,7,2'-trihydroxy-6-methoxyflavanone (10), 5,7,4'-trihydroxy-6-methoxyflavone (11), 5,7-dihydroxy-6,8-dimethoxy -flavone (12), 5,2',6'-trihydroxy-7,8-dimethoxyflavone (13), 5,7,2'-trihydroxy-8-methoxyflavone (14), 5,2'-dihydroxy-7,8-dimethoxyflavanone (15), 2'-hydroxy-5,7,8-trimethoxyflavone (16), 5-hydroxy-7,8-dimethoxyflavone (17), 5,2'-dihydroxy-7,8-dimethoxyflavone (18), and 5-hydroxy-6,7,8-trimethoxyflavone (19). For the first time, compounds 1-19 were isolated from S. moniliorrhiza, and compounds 6, 8, 9, 12, 19 were isolated from the Scutellaria genus.
Asunto(s)
Flavonoides/análisis , Scutellaria/química , FlavonasRESUMEN
Three new neo-clerodane diterpenoids, named scutestrigillosins A-C (1-3), were isolated from the whole plant of Scutellaria strigillosa. Their chemical structures including absolute configurations were established on the basis of detailed physical data analyses. In vitro, the isolated three new compounds exhibited significant cytotoxic activities against four tumor cell lines (HONE-1, P-388, MCF7 and HT29), and gave IC50 values in the range 3.5-7.7µM.
Asunto(s)
Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Diterpenos de Tipo Clerodano/química , Diterpenos de Tipo Clerodano/farmacología , Scutellaria/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Diterpenos de Tipo Clerodano/aislamiento & purificación , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Neoplasias/tratamiento farmacológicoRESUMEN
Two new neo-clerodane diterpenoids, named scutestrigillosins D and E (1 and 2), were isolated from the whole plant Scutellaria strigillosa. Their structures were established on the basis of detailed physical data analyses. In vitro, two new compounds exhibited cytotoxic activities against four tumor cell lines (HONE-1, P-388, MCF7, and HT29), and gave IC50 values in the range of 3.4-8.9 µΜ.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Diterpenos de Tipo Clerodano/aislamiento & purificación , Diterpenos de Tipo Clerodano/farmacología , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Antineoplásicos Fitogénicos/química , Diterpenos de Tipo Clerodano/química , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Células HT29 , Humanos , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Extractos Vegetales/química , Scutellaria/químicaRESUMEN
By means of preparative HPTLC and column chromatography over silica gel and Sephadex LH-20, fourteen diterpenoids were isolated and purified from the whole plants of Scutellaria galericulata. Based on the physico-chemical properties and spectral data, their structures were elucidated and identified asï¼scutebarbatine D(1), scutolide A(2), scutolide K(3), scutebata J(4), scutebata I(5), 6-O-acetylscutehenanine A(6), barbatin C(7), scutolide E(8), barbatine C(9), scutebarbatine Y(10), scutebarbatine B(11), scutestrigillosin A(12), scutebata O(13), scutolide B(14). Compounds 1-14 were isolated from S. galericulata for the first time.
Asunto(s)
Diterpenos de Tipo Clerodano/aislamiento & purificación , Scutellaria/química , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Extractos Vegetales/químicaRESUMEN
By means of preparative HPTLC and column chromatography over silica gel and Sephadex LH-20, ten sesquiterpenes were isolated and purified from the whole plants of Solanum septemlobum Bunge. Based on the physico-chemical properties and spectral data, their structures were elucidated and identified as: lyratol D(1), solajiangxin B(2), 1 ,2-dehydrocyperone(3), solanerianone A (4), dehydrocarissone(5), ligucyperonol(6), nardoeudesmol A(7), solajiangxin F(8), and lyratol B(9), solajiangxin D(10). For the first time, compounds 1-10 were isolated from Solanum septemlobum, and compounds 5-7 were obtained from the genus Solanum.
Asunto(s)
Medicamentos Herbarios Chinos/química , Sesquiterpenos/química , Solanum/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Espectrometría de Masas , Estructura Molecular , Sesquiterpenos/aislamiento & purificaciónRESUMEN
By means of preparative HPTLC and column chromatography over silica gel and Sephadex LH-20, nine diterpenoids were isolated and purified from the whole plants of Scutellaria strigillosa. Based on the physico-chemical properties and spectral data, their structures were elucidated as: 6-O-acetyl-7-O-nicotinoylscutebarbatine G(1), 6-O-nicotinoyl-7-O-acetylscutebarbatine G(2), 6,7-di-O-nicotinoylscutebarbatine G(3), scutebarbatine K(4), scutebarbatine B(5), 6-O-acetylscutehenanine A(6), 6-O-nicotinoylbarba- tin A(7), 6,7-di-O-acetoxylbarbatin A(8), scutebarbatine F(9). Compound 1 is a new diterpenoid, and compounds 2-9 were isolated from Scutellaria strigillosa for the first time.
Asunto(s)
Diterpenos/química , Medicamentos Herbarios Chinos/química , Scutellaria/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
Two new sesquiterpenoid derivatives, attributable to eudesmane-type (1-2, named septemlobin D and 11,12-O-isopropylidenesolajiangxin F), were isolated from the whole plant of Solanum septemlobum. Their structures were elucidated on the basis of integrated spectroscopic techniques, mainly HR-FAB-MS, 1D and 2D-NMR ((1)H-(1)H COSY, HMQC, HMBC and ROESY). In vitro, two sesquiterpenoid derivatives were found to show significant cytotoxicity against three cancer cell lines (P-388, HONE-1 and HT-29), and gave IC50 values in the range of 3.0-7.3 µM.
Asunto(s)
Antineoplásicos Fitogénicos/química , Sesquiterpenos de Eudesmano/química , Solanum/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Medicamentos Herbarios Chinos/química , Células HT29 , Humanos , Estructura Molecular , Sesquiterpenos de Eudesmano/aislamiento & purificaciónRESUMEN
Ten compounds were isolated and purified by column chromatography over silica gel, preparative TLC, and Sephadex LH-20 from the whole plant of Solanum lyratum. The structures were elucidated on the basis of physico-chemical properties and spectral data as 1beta-hydroxy-1 ,2-dihydro-alpha-santonin (1) , boscialin (2) , blumenol C (3), 3beta-hydroxy-5alpha, 6alpha-epoxy-7-megastigmen-9-one(4), dehydrovomifoliol(5) , blumenol A(6), (1'S,2R,5S, 10R) -2-(1', 2'-dihydroxy-l1'-methylethyl) -6,10-dimethylspiro[4,5] dec-6-en-8-one(7) , (1'R,2R,5S,10R)-2-( 1',2'-dihydroxy-l '-methylethyl) -6,1 l0-dimethylspiro[4,5]dec-6-en-8-one( 8) , 2-(1',2'-dihydroxy-1 '-methylethyl) -6,1 0-dimethyl-9-hydroxyspiro [4,5] dec-6-en-8-one (9) , and grasshopper ketone (10). Compounds 1-10 were isolated from this plant for the first time.