RESUMEN
Toosendanin (TSN) is a natural anti-cancer compound that is isolated from the traditional Chinese herbal Melia toosendan Sieb et Zucc. However, the research effect of TSN in the treatment of Triple negative breast cancer (TNBC) is still far from ideal. In this work, we investigated TSN and its derivatives in terms of their actions against MDA-MB-231 and HCC1806 TNBC cell lines. The results indicated that TSN and its derivative 11 showed excellent antitumor activity. Preliminary mechanistic studies showed that both compounds TSN and 11 induced S-phase arrest and G2/M phase cell number decrease in HCC1806 cells. Also, TSN and 11 significantly reduced the protein level of the well-known cancer suppressor gene p53, reduced the phosphorylation of AKT and ERK, and also induced the accumulation of phosphorylated p38 and p21.
Asunto(s)
Medicamentos Herbarios Chinos , Neoplasias de la Mama Triple Negativas , Humanos , Neoplasias de la Mama Triple Negativas/tratamiento farmacológico , Apoptosis , Medicamentos Herbarios Chinos/farmacología , Línea Celular , Línea Celular Tumoral , Proliferación CelularRESUMEN
Two new seco-prezizaane-type sesquiterpenes, 2ß-hydroxy-6-deoxyneoanisatin (1) and 3,4-anhydro-2-oxo-1α-hydroxy-6-deoxyneoanisatin (2), and two new prenylated C6 -C3 compounds, illilanceofunones A (3) and B (4), were obtained from the fruits of Illicium lanceolatum, along with four known prenylated C6 -C3 compounds (5-8). Their structures were proposed through HR-ESI-MS, 1 H, 13 C, and 2D NMR data interpretation. Moreover, the absolute configuration of 1 and 2 were further assigned by single-crystal X-ray diffraction analysis and electronic circular dichroism (ECD) calculations, respectively. Illihenryipyranol A (6) exhibited neuroprotective activity against MPP+ -induced PC12â cell damage in a dose-dependent manner.
Asunto(s)
Illicium/química , Fármacos Neuroprotectores/química , Sesquiterpenos/química , Animales , Supervivencia Celular/efectos de los fármacos , Dicroismo Circular , Frutas/química , Frutas/metabolismo , Illicium/metabolismo , Espectroscopía de Resonancia Magnética , Conformación Molecular , Fármacos Neuroprotectores/aislamiento & purificación , Fármacos Neuroprotectores/farmacología , Células PC12 , Extractos Vegetales/química , Prenilación , Ratas , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
Simonsinol is a natural sesqui-neolignan firstly isolated from the bark of Illicium simonsii. In this study, the anti-inflammatory activity of simonsinol was investigated with a lipopolysaccharide (LPS)-stimulated murine macrophages RAW264.7 cells model. The results demonstrated that simonsinol could antagonize the effect of LPS on morphological changes of RAW264.7 cells, and decrease the production of nitric oxide (NO), tumor necrosis factor α (TNF-α), and interleukin 6 (IL-6) in LPS-stimulated RAW264.7 cells, as determined by Griess assay and enzyme-linked immunosorbent assay (ELISA). Furthermore, simonsinol could downregulate transcription of inducible nitric oxide synthase (iNOS), TNF-α, and IL-6 as measured by reverse transcription polymerase chain reaction (RT-PCR), and inhibit phosphorylation of the alpha inhibitor of NF-κB (IκBα) as assayed by Western blot. In conclusion, these data demonstrate that simonsinol could inhibit inflammation response in LPS-stimulated RAW264.7 cells through the inactivation of the nuclear transcription factor kappa-B (NF-κB) signaling pathway.
Asunto(s)
Antiinflamatorios/farmacología , Lignanos/farmacología , Lipopolisacáridos/farmacología , FN-kappa B/metabolismo , Transducción de Señal/efectos de los fármacos , Animales , Supervivencia Celular/efectos de los fármacos , Interleucina-6/biosíntesis , Interleucina-6/genética , Ratones , Inhibidor NF-kappaB alfa/metabolismo , Óxido Nítrico/biosíntesis , Óxido Nítrico Sintasa de Tipo II/genética , Fosforilación/efectos de los fármacos , Células RAW 264.7 , Transcripción Genética/efectos de los fármacos , Factor de Necrosis Tumoral alfa/biosíntesis , Factor de Necrosis Tumoral alfa/genéticaRESUMEN
To establish a quality constant evaluation system of Alismatis Rhizoma decoction pieces,in order to provide reference for regulating the market circulation of this decoction pieces. A total of 18 batches of Alismatis Rhizoma decoction pieces were collected from different pharmaceutical factories,and the morphological parameters of each sample were tested. The content of alisol B 23-acetate in Alismatis Rhizoma decoction pieces was determined by HPLC in the 2015 edition of Chinese Pharmacopoeia,and the parameters such as quality constant and relative quality constant were calculated. The quality constant range of 18 batches of Alismatis Rhizoma decoction pieces was 0. 390-2. 076. If 18 batches of Alismatis Rhizoma decoction pieces were divided into 3 grades,taking 80% of the maximum quality constant as first grade,50% to 80% as second grade,and the rest as third grade,then the quality constant of firstgrade samples was ≥1. 66,the quality constant of second-grade samples was ≥1. 04 and <1. 66,and the quality constant of third-grade samples was <1. 04. The established quality constant evaluation method is objective and feasible,which can be used to classify the grade of Alismatis Rhizoma decoction pieces and provide a reference method to control the quality of this decoction pieces.
Asunto(s)
Alisma/química , Medicamentos Herbarios Chinos/normas , Cromatografía Líquida de Alta Presión , Control de Calidad , Rizoma/químicaRESUMEN
In this study, four new lignan glucosides, named difengpiosides A-D (1-4), were isolated from the stem barks of Illicium difengpi, together with seven known compounds 5-11. Their structures were identified on the basis of spectroscopic analyses (1D and 2D NMR, HRESIMS, CD) and a comparison with literature data. All the compounds were evaluated for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells.
Asunto(s)
Glucósidos/química , Glucósidos/farmacología , Illicium/química , Lignanos/análisis , Óxido Nítrico/análisis , Animales , Glucósidos/aislamiento & purificación , Lipopolisacáridos/farmacología , Ratones , Estructura Molecular , Corteza de la Planta/química , Extractos Vegetales/química , Tallos de la Planta/química , Células RAW 264.7RESUMEN
Five selective 11ß-hydroxysteroid dehydrogenase type 1 (11ß-HSD1) competitive inhibitors, hupehenols A-E (1-5), were isolated from Viburnum hupehense. The structure elucidation indicated that compounds 1-5 are new 20,21,22,23,24,25,26,27-octanordammarane triterpenoids. Their structures were established on the basis of NMR spectroscopic and mass spectrometric analysis. Hupehenols A-E (1-5) showed inhibition against human 11ß-HSD1, with hupehenols B (2) and E (5) having IC50 values of 15.3 and 34.0 nM, respectively. Moreover, hupehenols C (3) and D (4) are highly selective inhibitors of human 11ß-HSD1 when compared to murine 11ß-HSD1.
Asunto(s)
11-beta-Hidroxiesteroide Deshidrogenasa de Tipo 1/antagonistas & inhibidores , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Viburnum/química , Animales , Medicamentos Herbarios Chinos/química , Humanos , Ratones , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Componentes Aéreos de las Plantas/química , Relación Estructura-Actividad , Triterpenos/químicaRESUMEN
Fourteen compounds were isolated from 95% ethanol extract by silica gel, MCI, and ODS column chromatography. These compounds were respectively identified as quercetin (1), kaempferol (2), (+)-catechin (3), fraxin (4), protocatechuic acid (5), gallic acid (6), methyl gallate (7), ethyl gallate (8), apocynol A (9), baccatin (10), cerevisterol (11), ellagic acid (12), 3, 3',4'-tri-0-methylellagic acid(13) and N-benzoyl-L-phenylalaninyl-N-benzoyl-L-phenylalaninate(14) by analyzing their spectral data and comparing with the previously reported literatures. Except for gallic acid (6), all other compounds were isolated from this plant for the first time. Compounds 1, 2 and 6 showed moderate anti-proliferation activities on tumor cells.
Asunto(s)
Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/toxicidad , Euphorbiaceae/química , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Humanos , Plantas Medicinales/química , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
Sixteen compounds have been isolated from the EtOAc fraction of 95% ethanolic extract of Sophora dunnii through silica gel, Sephadex LH-20 and semi-prerarative HPLC column chromatographies. Their structures were identified on the basis of NMR and MS spectra data as phaseollidin (1), L-maackiain (2), 2-(2',4'-dihidroxyphenyl)-5,6-methylenedioxy benzofuran (3), 8-demethyl-farrerol (4), liquiritigenin (5), genistein (6), 6-methylgenistein (7), 5-O-methyl genistein (8), 7,2',4'-trihydroxys-5-methoxy-isoflavanone (9), 7, 3', 4'-trihydroxy-isoflavanone (10), erythribyssin D (11), calycosin (12), trans-resveratrol (13), cis-resveratrol (14), stigmasterol (15), ß-sitosterol (16). Among these, compounds 1-14 and 16 were isolated from this plant for the first time.
Asunto(s)
Medicamentos Herbarios Chinos/química , Sophora/química , Fraccionamiento Químico , Medicamentos Herbarios Chinos/aislamiento & purificación , Estructura Molecular , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
Three new ergosterols featuring with a highly conjugated ring system, psathrosterols C-E (1-3), have been isolated from the fungus Psathyrella rogueiana. The structures with the absolute configurations were elucidated by means of spectroscopic methods and single crystal X-ray diffraction. Compounds 1-3 exhibit inhibitory activity against NO production with IC50 values ranging from 8.4 to 21.8 µM. Compound 1 inhibits the LPS-induced proliferation of B lymphocyte cells with an IC50 value of 12.3 µM.
Asunto(s)
Antiinflamatorios , Ergosterol , Inmunosupresores , Ergosterol/aislamiento & purificación , Ergosterol/farmacología , Ergosterol/análogos & derivados , Ergosterol/química , Estructura Molecular , Ratones , Animales , Antiinflamatorios/farmacología , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/química , Inmunosupresores/farmacología , Inmunosupresores/química , Inmunosupresores/aislamiento & purificación , Células RAW 264.7 , Óxido Nítrico , Linfocitos B/efectos de los fármacos , China , Proliferación Celular/efectos de los fármacosRESUMEN
Five new compounds, including two sesquiterpenoid glycosides (1 and 2), two monoterpenoid glycosides (3 and 4), and a quinovose ester (5), together with four known compounds (6-9) were isolated from branches and leaves of Pittosporum pulchrum Gagnep. Their structures were established by 1D and 2D NMR, HR-ESI-MS, IR and UV spectral analyses. This is the first time to investigate the chemical constituents of P. pulchrum. Subsequently, the anti-inflammatory and antioxidant activities of different solvent fractions of ethanol extract and isolated compounds were evaluated. Dichloromethane and ethyl acetate fractions dramatically inhibited the production of NO in a concentration-dependent manner in LPS-induced RAW264.7 cells. Ethyl acetate and n-butanol fractions showed excellent DPPH radical scavenging activities with IC50 values of 24.31 µg/mL and 27.81 µg/mL, respectively. Compounds 7 and 8 might be potential natural antioxidants with IC50 values of 16.13 µM and 24.81 µM, respectively.
Asunto(s)
Antiinflamatorios , Antioxidantes , Fitoquímicos , Hojas de la Planta , Hojas de la Planta/química , Ratones , Células RAW 264.7 , Animales , Estructura Molecular , Antioxidantes/farmacología , Antioxidantes/aislamiento & purificación , Antioxidantes/química , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Antiinflamatorios/farmacología , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/química , Glicósidos/aislamiento & purificación , Glicósidos/farmacología , Glicósidos/química , Óxido Nítrico/metabolismo , Tallos de la Planta/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Sesquiterpenos/química , China , Monoterpenos/aislamiento & purificación , Monoterpenos/farmacologíaRESUMEN
ETHNOPHARMACOLOGICAL RELEVANCE: Callicarpa longissima is a typical Yao ethnomedicine that has been used to treat arthritis in China. Our previous study found that the dichloromethane extract (DCME) of C. longissima showed anti-inflammatory activity in vitro. However, the anti-inflammatory mechanism and detailed chemical composition of DCME remain unclear, which lead to the original interest of this study. AIM OF THE STUDY: The study aimed to evaluate the anti-inflammatory properties of the DCME from C. longissima and further explore the accurate chemical components responsible for this active extract. MATERIALS AND METHODS: The anti-inflammatory activity of DCME in vivo was tested with carrageenan-induced mice paw edema model. Its anti-inflammatory mechanism was explored with LPS-stimulated RAW264.7 macrophages model. The compounds in DCME were isolated by repeated column chromatography and their structures were identified on the basis of nuclear magnetic resonance spectroscopy. The anti-inflammatory activities of the isolates in vitro were also tested by suppressing releases of inflammatory mediators (NO, IL-6 and TNF-α) in RAW264.7 macrophages model. In addition, the molecular docking analysis, which evaluated the potential interaction between the compounds and Toll-like receptor 4 (TLR4) and nuclear factor κB (NF-κB), was performed. RESULTS: DCME effectively alleviated the mice paw edema induced by carrageenan. In LPS-stimulated RAW264.7â¯cells, DCME significantly decreased the production of interleukin (IL)-6 and tumor necrosis factor α (TNF-α) via inhibiting their mRNA transcription, down-regulated the expression of TLR4 and myeloid differentiation factor 88, inhibited the phosphorylation of alpha inhibitor of NF-κB (IκBα), NF-κB p65, and degradation of IκBα. Twelve diterpenoid phenols were identified from DCME, and they not only showed different inhibitory effects on the production of NO, IL-6 and TNF-α in LPS-stimulated RAW264.7â¯cells, but also could bind to TLR4 and NF-κB as analyzed by molecular docking. CONCLUSIONS: Taken together, DCME from C. longissima could inhibit inflammatory response both in vitro and in vivo, which is mainly attributed to the synergistic effect of abundant diterpenoid phenols through inhibiting the TLR4/NF-κB signaling pathway, and might be a promising agent for the treatment of inflammatory diseases.
Asunto(s)
Callicarpa , Diterpenos , Animales , Ratones , FN-kappa B/metabolismo , Inhibidor NF-kappaB alfa/metabolismo , Cloruro de Metileno/efectos adversos , Interleucina-6/metabolismo , Carragenina/farmacología , Factor de Necrosis Tumoral alfa/metabolismo , Receptor Toll-Like 4/metabolismo , Lipopolisacáridos/farmacología , Simulación del Acoplamiento Molecular , Transducción de Señal , Antiinflamatorios/efectos adversos , Diterpenos/farmacología , Edema/inducido químicamente , Edema/tratamiento farmacológicoRESUMEN
11ß-Hydroxysteroid dehydrogenase 1 (11ß-HSD1) represents a promising drug target for metabolic syndrome, including obesity and type 2 diabetes. Our initial screen of a collection of natural products from Danshen led to the identification of tanshinones as the potent and selective 11ß-HSD1 inhibitors. To improve the druggability and explore the structure-activity relationships (SARs), more than 40 derivatives have been designed and synthesized using tanshinone IIA and cryptotanshinone as the starting materials. More than 10 derivatives exhibited potent in vitro 11ß-HSD1 inhibitory activity and good selectivity over 11ß-HSD2 across human and mouse species. Based on the biological results, SARs were further discussed, which was also partially rationalized by a molecular docking model of 1 bound to the 11ß-HSD1. Remarkably, compounds 1, 17 and 30 significantly inhibited 11ß-HSD1 in 3T3-L1 adipocyte and in livers of ob/ob mice, which merits further investigations as anti-diabetic agents. This study not only provides a series of novel selective 11ß-HSD1 inhibitors with promising therapeutic potentials in metabolic syndromes, but also expands the boundaries of the chemical and biological spaces of tanshinones.
RESUMEN
Four new terpenoids, metaseglyptorin A (1), metasequoic acid C (2), 12α-hydroxy-8,15-isopimaradien-18-oic acid (3), and (-)-acora-2,4(14),8-trien-15-oic acid (4), and three new norlignans, metasequirins D-F (5-7), were isolated from Metasequoia glyptostroboides, together with 15 known compounds. Structures of the new compounds were determined by analysis of their spectroscopic data, and the absolute configuration of 7 was established by the modified Mosher method. All of the compounds were evaluated for cytotoxicity against five human tumor cell lines.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Lignanos/aislamiento & purificación , Plantas Medicinales/química , Terpenos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Cupressaceae , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Humanos , Lignanos/química , Lignanos/farmacología , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Hojas de la Planta/química , Terpenos/química , Terpenos/farmacologíaRESUMEN
Two new oleanane triterpenoids (1-2) and one new vibsane-type diterpenoid (3), together with 7 known compounds (4-10), were isolated from the leaves of Viburnum chingii. The structures of compounds 1-3 were elucidated by means of spectroscopic methods including extensive 1D- and 2D-NMR technique. Cytotoxicity of compounds 1-10 were tested against HL-60, SMMC-7721, A-549, SK-BR-3, and PANC-1 cell lines. Compound 3 showed significant cytotoxicity against HL-60, SK-BR-3, and PANC-1 cell lines.
Asunto(s)
Antineoplásicos Fitogénicos/química , Diterpenos/química , Ácido Oleanólico/química , Triterpenos/química , Viburnum/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/toxicidad , Línea Celular Tumoral , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Diterpenos/toxicidad , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Espectroscopía de Resonancia Magnética , Conformación Molecular , Ácido Oleanólico/aislamiento & purificación , Ácido Oleanólico/farmacología , Ácido Oleanólico/toxicidad , Hojas de la Planta/química , Triterpenos/aislamiento & purificación , Triterpenos/toxicidadRESUMEN
Four new acylphloroglucinols with an unusual 6/6/5 spirocyclic skeleton, hyperbeanols A-D (1-4), were isolated from the methanol extract of Hypericum beanii along with 16 known compounds. Their structures were established on the basis of spectroscopic and X-ray diffraction analysis. Hyperbeanols A-C were three stereoisomers different only at the relative configuration of C-4 and C-13, which were distinguished by the nuclear Overhauser effect spectroscopy (NOESY) spectroscopic data in combination with the single X-ray analysis of hyperbeanol A (1). The cytotoxic activity of hyperbeanols A-D against the cancer cell lines SK-BR-3, HL-60, SMMC-7721, PANC-1, MCF-7, and K562 was also evaluated.
Asunto(s)
Antineoplásicos Fitogénicos/química , Hypericum/química , Floroglucinol/análogos & derivados , Fitoterapia , Extractos Vegetales/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Evaluación Preclínica de Medicamentos , Ensayos de Selección de Medicamentos Antitumorales , Células HL-60 , Humanos , Estructura Molecular , Floroglucinol/química , Floroglucinol/metabolismo , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , EstereoisomerismoRESUMEN
Illicium difengpi is well-known as its stem barks that have been widely used in the Traditional Chinese Medicine (TCM) for therapy rheumatoid arthritis and traumatic injury. To comprehensive utilization of resources, the phytochemical investigation on the branches and leaves of this plant was carried out, which led to the isolation of an undescribed neolignan along with three known lignans. Their structures were elucidated on the basis of extensive spectroscopic data and the new compound was elucidated as a neolignan possessing a dihydropyran ring formed by a unique conjugation way and named difengpienol C. Difengpienol C showed the strongest anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated RAW264.7 cells, which powerfully inhibited nitric oxide (NO), interleukin 6 (IL-6), tumor necrosis factor α (TNF-α) production and suppressed the mRNA transcription of inducible nitric oxide synthase (iNOS), IL-6 and TNF-α. Besides, difengpienol C blocked the activation of TLR4/MyD88/NF-κB signaling pathway. Therefore, difengpienol C might be a potent agent for anti-inflammatory drug development, and the non-traditional medicinal parts of Illicium difengpi can be identified as the source of natural anti-inflammatory molecules.
Asunto(s)
Antiinflamatorios/farmacología , Illicium/química , Lignanos/farmacología , Animales , Antiinflamatorios/aislamiento & purificación , China , Interleucina-6 , Lignanos/aislamiento & purificación , Ratones , Estructura Molecular , FN-kappa B , Óxido Nítrico , Óxido Nítrico Sintasa de Tipo II , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Hojas de la Planta/química , Plantas Medicinales/química , Células RAW 264.7 , Transducción de Señal , Receptor Toll-Like 4 , Factor de Necrosis Tumoral alfaRESUMEN
Nine new germacrane sesquiterpenes, trijugins A-I (1-9), a new lupane triterpenoid, 3alpha-O-acetyl-20(29)-lupen-2alpha-ol (10), and 24 known terpenoids were isolated from Salvia trijuga. The structure of compound 1 was confirmed by single-crystal X-ray diffraction. Compounds 1-10 and 32 were evaluated for their cytotoxicity against five human tumor cell lines. Compounds 9 and 32 exhibited moderate toxicity effects against several cell lines.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Salvia/química , Sesquiterpenos de Germacrano/aislamiento & purificación , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Cristalografía por Rayos X , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Células HL-60 , Humanos , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/farmacología , Triterpenos/químicaRESUMEN
Two new C(30)-epimeric polycyclic polyprenylated acylphloroglucinols (PPAPs), named uralodins B and C (1 and 2, resp.), were isolated from the aerial parts of Hypericum henryi subsp. uraloides together with two new chromone glucosides, urachromones A and B (3 and 4, resp.), as well as 16 known compounds. Their structures were established by extensive NMR techniques and MS analysis. The epimers 1 and 2 always behaved like a single compound when examined by TLC, and were separated by HPLC. Their configuration was distinguished by comparative analysis of the NMR data with known analogues together with the ROESY experiment. All the isolated PPAPs were evaluated for their cytotoxic activities against HepG2, SGC7901, HL-60, and K562 cell lines. Compound 1 showed modest cytotoxic activities against SGC7901 and HL-60 cell lines, and 2 showed modest cytotoxic activities against HepG2, SGC7901, HL-60, and K562 cell lines.
Asunto(s)
Cromonas/química , Glucósidos/química , Hypericum/química , Floroglucinol/química , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales , Glucósidos/aislamiento & purificación , Glucósidos/toxicidad , Células HL-60 , Células Hep G2 , Humanos , Células K562 , Conformación Molecular , Floroglucinol/aislamiento & purificación , Floroglucinol/toxicidadRESUMEN
A phytochemical investigation on the stems of Mappianthus iodoides led to the isolation of a new naturally occurring prenylated isoflavone, mappianthone A (1), together with seven known analogues (2-8). The structure of 1 was elucidated by extensive spectroscopic methods and the known compounds were identified by comparison with data reported in the literature. All isolated compounds were evaluated for their antiproliferative activities against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 in vitro. Compounds 1-8 showed significant antiproliferative effects against several human cancer cell lines with IC50 values ranging from 0.16 to 12.68 µM. [Formula: see text].
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Isoflavonas/farmacología , Magnoliopsida/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Concentración 50 Inhibidora , Isoflavonas/química , Isoflavonas/aislamiento & purificación , Estructura Molecular , Fitoquímicos/análisis , Fitoquímicos/aislamiento & purificación , PrenilaciónRESUMEN
Two rare N-ß-D-glucopyranosyl-1H-indole-3-acetic acid conjugates, N-[2-(1-ß-D-glucopyranosyl)-1H-indol-3-yl)acetyl]-L-glutamic acid (1) and N-[2-(1-ß-D-glucopyranosyl)-1H-indol-3-yl)acetyl]-L-aspartic acid (2) were isolated from Ginkgo biloba. The structures were elucidated by analyses of HRMS and NMR spectroscopic data. In addition, a simplified and efficient synthetic route for compounds 1 and 2 is also disclosed to determine the absolute configurations of them. This concise syntheses of compounds 1 and 2 may facilitate studies of the biology of this type alkaloids. Compounds 1 and 2 were also tested for their cytotoxic and anti-inflammatory activities. The biological evaluation showed that compounds 1 and 2 led to the decrease of interleukin (IL)-6, nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 at mRNA level in lipopolysaccharide (LPS)-stimulated murine macrophage RAW264.7 cells.