RESUMEN
Two new iridoid glycosides, piasezkiiosides A (1) and B (2), were isolated from aqueous extract of the whole plant of Rehmannia piasezkii. Their structures were established from the spectroscopic data, chemical transformation, and X-ray diffraction analysis. Compound 1 exhibited weak hepatoprotective activity against APAP-induced HepG2 cell damage.
Asunto(s)
Glicósidos Iridoides , Rehmannia , Glicósidos Iridoides/farmacología , Glicósidos Iridoides/química , Glicósidos Iridoides/aislamiento & purificación , Humanos , Células Hep G2 , Estructura Molecular , Rehmannia/química , Medicamentos Herbarios Chinos/farmacología , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/aislamiento & purificaciónRESUMEN
Four new iridoid glycosides (1-4), rehmaglutosides L-O, were isolated from the air-dried roots of Rehmannia glutinosa. Their structures were established from the spectroscopic data obtained and by chemical evidence. The known mellittoside (5) and ajugol (6) were also obtained in the current investigation, and the structure of mellittoside was unequivocally defined using X-ray diffraction data. Compounds 1-6 were tested for their cytotoxicity against five human tumor cell lines and proliferation effects on Lactobacillus Reuteri.
Asunto(s)
Glicósidos , Rehmannia , Humanos , Glicósidos/farmacología , Glicósidos/química , Rehmannia/química , Glicósidos Iridoides/farmacologíaRESUMEN
Seven new pentasaccharides (1-7), rehmaglupentasaccharides A-G, were isolated from the air-dried roots of Rehmannia glutinosa. Their structures were established from the spectroscopic data obtained and by chemical evidence. The known verbascose (8) and stachyose (9) were also obtained in the current investigation, and the structure of stachyose was unequivocally defined using X-ray diffraction data. Compounds 1-9 were tested for their cytotoxicity against five human tumor cell lines, influence on dopamine receptor activation, and proliferation effects against Lactobacillus reuteri.
Asunto(s)
Rehmannia , Humanos , Rehmannia/química , Línea Celular , Raíces de Plantas/químicaRESUMEN
Three new cyclopentanoid monoterpenes, neopiscrocins A-C (1-3), together with 14 known compounds (4-17), were isolated from the roots of Picrorhiza scrophulariiflora. The structres of these compounds were elucidated on the basis of their spectroscopic data. All compounds were evaluated for cytotoxicity against six human tumor cell lines (PC9, PANC1, HCT-116, Hep-G2, BGC-823, and MCF-7), hepatoprotective activity and anti-inflammatory activity.
RESUMEN
Five new fatty acids with a terminal 3-oxo-cyclopentene ring, cyclopentenone acids A-E (1-5), were isolated from the ethanol extract of the seeds of Hydnocarpus anthelminthica. The structures of these compounds were elucidated on the basis of their spectroscopic data and chemical evidence. Compounds 1-3 were evaluated for their anti-inflammatory activity based on the inhibition of NO production in microglial BV2 cells, and all of them showed weak anti-inflammatory activities.
Asunto(s)
Ácidos Grasos , Semillas , Antiinflamatorios , Ácidos Grasos/análisis , Ácidos Grasos/farmacología , Estructura Molecular , Semillas/químicaRESUMEN
Three new erythrina alkaloids, eryalkals A (1), B (2), and C (3), were isolated from the roots of Erythrina corallodendron L. Their structures, including their absolute configurations, were elucidated based on analyses of HR-ESI-MS, 1D/2D NMR and single-crystal X-ray diffraction techniques. The isolated erythrina alkaloids were screened for the antioxidant and cytotoxic activities. All the compounds showed no antioxidant activity and cytotoxic activities.
Asunto(s)
Alcaloides , Erythrina , Antioxidantes , Estructura Molecular , Raíces de PlantasRESUMEN
Four new ionones and ionone glycosides (1-4) were isolated from the whole plant of Rehmannia piasezkii Maxim. Their planar structures as well as absolute configuration were confirmed via spectroscopic analysis, ECD calculation, and X-ray crystallography. Compounds 1-4 were tested for their cytotoxicity against five human tumor cell lines and ability to inhibit LPS-activated NO production in the BV2 cell line.
Asunto(s)
Rehmannia , Humanos , Rehmannia/química , Norisoprenoides/química , Glicósidos/farmacología , Glicósidos/química , Estructura Molecular , Línea Celular TumoralRESUMEN
As part of an ongoing project on Rehmannia species, three new pyridine alkaloides (glutinosines A - C), and one new iridoid analogue (rehmaglutin E), were isolated from the leaves of Rehmannia glutinosa. The structures of the new compounds were established by extensive spectroscopic analysis and electronic circular dichroism calculations.
Asunto(s)
Alcaloides , Rehmannia , Rehmannia/química , Iridoides , Estructura Molecular , Hojas de la Planta/química , Alcaloides/análisis , PiridinasRESUMEN
The present study investigated the chemical constituents from the dry seeds of Hydnocarpus anthelminthica. The compounds were isolated and purified from the dry seeds of H. anthelminthica by various chromatographic techniques including column chromatography over silica gel and Sephadex LH-20 and reversed-phase HPLC. Their structures were identified by spectroscopic analysis. The in vitro cytotoxic activities were determined by MTT assay. Ten compounds were isolated and identified as 2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(2-hydroxy-5-methoxyphenyl)-3-oxo-1-propanol(1), threo-1,2-bis-(4-hydroxy-3-methoxyphenyl)-propane-1,3-diol(2), erythro-1,2-bis-(4-hydroxy-3-methoxyphenyl)-propane-1,3-diol(3), 2-(4-hydroxy-3-methoxyphenyl)-3-(2-hydroxy-5-methoxyphenyl)-3-oxo-1-propanol(4), 3-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-propan-1-one(5), chrysoeriol(6), evofolin B(7), apigenin-3'-methoxy-7-O-rutinoside(8), luteolin(9), and vitexin(10). Compound 1 is a new compound. Compounds 4 and 5 were isolated from this genus for the first time. All compounds showed no significant cytotoxic activity.
Asunto(s)
1-Propanol , Propano , 1-Propanol/análisis , Propano/análisis , Semillas/químicaRESUMEN
Ten new bisbenzylisoquinoline alkaloids (1-10) and eight known analogues (11-18) were obtained from the roots of Stephania tetrandra. The structures of these compounds were determined by spectroscopic methods, single-crystal X-ray diffraction, electronic circular dichroism analyses, and chemical method. Compounds 1, 15, and 16 showed the better anti-inflammatory activities with IC50 values of 15.26 ± 2.99, 6.12 ± 0.25, and 5.92 ± 1.89 µM, respectively. Compound 18 possessed cytotoxic activities against MCF-7, HCT-116, and HepG2 cell lines with IC50 values of 2.81 ± 0.06, 3.66 ± 0.26, and 2.85 ± 0.15 µM, respectively.
Asunto(s)
Antiinflamatorios/farmacología , Antineoplásicos Fitogénicos/farmacología , Bencilisoquinolinas/farmacología , Óxido Nítrico/antagonistas & inhibidores , Raíces de Plantas/química , Stephania tetrandra/química , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Bencilisoquinolinas/química , Bencilisoquinolinas/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Ratones , Estructura Molecular , Óxido Nítrico/biosíntesis , Relación Estructura-ActividadRESUMEN
Eight new iridoids (1-8) and an ionone glucoside (9), together with 31 known compounds (10-40), were isolated from the whole plants of Rehmannia henryi. The structures of these compounds were elucidated on the basis of their spectroscopic data and chemical evidence.
Asunto(s)
Iridoides/química , Norisoprenoides/química , Rehmannia/química , Estructura MolecularRESUMEN
Five new iridoids (1-5), jiohenrins A-E, together with sixteen known compounds (6-21), were isolated from the whole plants of Rehmannia henryi. The structures of these compounds were elucidated on the basis of their spectroscopic data.
Asunto(s)
Iridoides/aislamiento & purificación , Rehmannia/química , Línea Celular Tumoral , Humanos , Iridoides/química , Iridoides/farmacología , Imagen por Resonancia MagnéticaRESUMEN
This project is to investigate lignans from the seed of Hydnocarpus anthelminthica. Thirteen lignans were isolated from the 95% ethanol extract of the seed of H. anthelminthica, by polyamide resin, Sephadex LH-20, ODS column chromatography and preparative HPLC. Their structures were elucidated as(+)-syringaresinol(1), lirioresinol A(2),(+)-medioresinol(3),(7R,8R,8'R)-4'-guaiacylglyceryl-evofolin B(4), leptolepisol C(5),(-)-(7R,7'R,7â³R,8S,8'S,8â³S)-4',4â³-dihydroxy-3,3',3â³,5,5',5â³-hexamethoxy-7,9':7',9-diepoxy-4,8â³-oxy-8,8'-sesquineolignan-7â³,9â³-diol(6),(-)-(7R,7'R,7â³R,8S,8'S,8â³S)-4',4â³-dihydroxy-3,3',3â³,5,5'-pentamethoxy-7,9':7',9-diepoxy-4,8â³-oxy-8,8'ses-quineolignan-7â³,9â³-diol(7), ceplignan(8), hydnocarpusol(9), isohydnocarpin(10),(-)-hydnocarpin(11), hydnocarpin(12), and hydnocarpin-D(13) by spectroscopic data analysis. Compounds 1-8 were obtained from the genus Hydnocarpus for the first time.
Asunto(s)
Lignanos/análisis , Magnoliopsida/química , Extractos Vegetales/análisis , Semillas/química , Estructura Molecular , Fitoquímicos/análisisRESUMEN
This project is to investigate chemical compositions from the roots of Erythrina corallodendron. Through the methods of silica gel,ODS,Sephadex LH-20 column chromatography and preparative HPLC,15 compounds were isolated from the 95% ethanol extract of the roots of E. corallodendron. Based on spectroscopic techniques,the structures of these compounds were identified as 10,11-dioxoerythraline( 1),erythrinine( 2),erythraline( 3),11-methoxyerythraline( 4),cristanines B( 5),erythratine( 6),erysotrine( 7),medioresinol( 8),( ±)-ficusesquilignan A( 9),( +)-pinoresinol( 10),nicotinic acid( 11),dibutyl phthalate( 12),vanillic acid( 13),3-hydroxy-1-( 4-hydroxy-3-methoxyphenyl)-1-propanone( 14),and syringic acid( 15). Compounds 8-10 are isolated from genus Erythrina for the first time and all compounds are isolated from E. corallodendron for the first time. Furthermore,this paper screened the antioxidant and cytotoxic activities of the compounds using models of liver microsomal oxidation inhibition and MTT.
Asunto(s)
Erythrina/química , Fitoquímicos/análisis , Raíces de Plantas/química , Antioxidantes/análisis , Cromatografía Líquida de Alta Presión , Microsomas Hepáticos/efectos de los fármacos , Extractos Vegetales/análisisRESUMEN
Six new iridal-type triterpenoids containing an unprecedented cyclopentane ring, polycycloiridals E-J (1-6), were isolated from a large-scale re-extraction of Iris tectorum. A possible biosynthesis pathway is postulated. The known spirioiridotectal D (7) was also obtained in the current investigation, and its structure was unequivocally defined using X-ray diffraction data. Compound 7 suppressed LPS-activated NO production in the BV2 cell line with an IC50 value of 0.54 µM.
Asunto(s)
Ciclopentanos/aislamiento & purificación , Género Iris/química , Rizoma/química , Triterpenos/aislamiento & purificación , Ciclopentanos/química , Ciclopentanos/farmacología , Estructura Molecular , Extractos Vegetales/química , Triterpenos/química , Triterpenos/farmacología , Difracción de Rayos XRESUMEN
Three new flavonoid glycosides (1-3) and one new aristololactam N-glycoside (4) were isolated from the rhizome of Aristolochia championii. The structures of compounds 1-4 were elucidated on the basis of their spectroscopic data and chemical evidence (UV, IR, HR-ESI-MS, 1D and 2D NMR). Their structures were determined as 8-(5-formyl-2-furanmethyl)-isorhamentin 3-O-robinobioside (1), 8-(5-methyl-2-furanoyl)-isorhamentin 3-O-robinobioside (2), 8-formylisorhamentin 3-O-robinobioside (3), and N-ß-D-glucopyranosylaristololactam V (4), respectively.
Asunto(s)
Aristolochia/química , Flavonoides/aislamiento & purificación , Glicósidos/aislamiento & purificación , Rizoma/química , Medicamentos Herbarios Chinos/química , Flavonoides/química , Glicósidos/química , Estructura Molecular , EstereoisomerismoRESUMEN
Phytochemical investigation of the rhizomes of Iris tectorum resulted in the isolation and characterization of three new apocynin derivatives, apocynin-4-O-ß-D-(6'-O-syringyl)glucopyranoside (1), scrophenoside C-7-ethyl ether (2, 3), together with a new naturally occurring compound but known by synthesis, apocynin-4-O-ß-D-xylopyranoside (4), and five known ones (5-9). Their structures were elucidated on the basis of spectroscopic data interpretation.
Asunto(s)
Acetofenonas/aislamiento & purificación , Género Iris/química , Acetofenonas/química , Glicósidos/química , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Extractos Vegetales/química , Rizoma/químicaRESUMEN
Nine new iridoid glycosides, rehmachingiiosides A-I (1-9), together with 16 known analogues, were isolated from the whole plants of Rehmannia chingii. The structures of compounds 1-9 were elucidated on the basis of spectroscopic data analysis and from chemical evidence. Furthermore, in two vitro assays, compounds 5 and 10 showed an inhibitory effect on LPS-induced NO production with IC50 values of 2.5 and 7.3 µM, and compounds 4, 6, and 10-12 (when evaluated at 10 µM) exhibited evidence of hepatoprotective effects against APAP-induced HepG2 cell damage.
Asunto(s)
Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Glicósidos Iridoides/aislamiento & purificación , Glicósidos Iridoides/farmacología , Rehmannia/química , Acetaminofén/farmacología , Animales , Medicamentos Herbarios Chinos/química , Células Hep G2 , Humanos , Concentración 50 Inhibidora , Glicósidos Iridoides/química , Lipopolisacáridos/farmacología , Hígado/efectos de los fármacos , Ratones , Microglía/efectos de los fármacos , Estructura Molecular , Óxido Nítrico/biosíntesis , Resonancia Magnética Nuclear BiomolecularRESUMEN
Five new compounds, including a rare phenyldihydronaphthalene lignanamide (1), an unusual hybrid-norlignan derivative (2), a rare cycloheptenone oxide derivative (3), one new acorane-type sesquiterpenoid (4), and one new guaiane-type sesquiterpenoid (5), together with seven known compounds (6-12), have been isolated from the rhizomes of Acorus tatarinowii. The structures of compounds 1-5 were determined by means of extensive spectroscopic methods. To the best of our knowledge, this is first report of a phenyldihydronaphthalene lignanamide and hybrid-norlignan and cycloheptenone oxide derivatives from the genus Acorus. In addition, compound 5 represents the first guaiane-type sesquiterpenoid with an epoxy group located between C-6 and C-9 from natural sources. Compounds 1-12 were evaluated for their in vitro cytotoxicity against five tumor cell lines. Among them, 2, 3, 5, and 10 exhibited moderate cytotoxicity with IC50 values of 2.11-9.23 µM.
Asunto(s)
Acorus/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Lignanos/aislamiento & purificación , Sesquiterpenos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Lignanos/química , Lignanos/farmacología , Estructura Molecular , Rizoma/química , Sesquiterpenos/química , Sesquiterpenos/farmacologíaRESUMEN
Nine new compounds, together with 16 known analogs, were isolated from the whole plants of Rehmannia chingii. The structures of compounds 1-9 were elucidated on the basis of their spectroscopic data and chemical evidence. In addition, the new compounds were tested for their hepatoprotective activities against APAP-induced HepG2 cell damage and their ability to inhibit LPS-induced nitric oxide production in the murine microglia BV2 cell line. Compounds 2 and 5 exhibited pronounced hepatoprotective activities against APAP-induced HepG2 cell damage at a concentration of 10 µM, and compounds 4 and 9 showed moderate inhibitory activity against microglial inflammation factor with IC50 values of 3.51 and 7.11 µM, respectively.