RESUMEN
In the present study, six new compounds namely, picralactones CH (1-6) along with nine known compounds (7-15) were isolated from the branches and leaves of Picrasma chinese P.Y. Chen. Their structures were determined with the help of spectroscopic techniques such as NMR, HR-ESI-MS, UV, IR and CD. Cytotoxicity of all compounds was evaluated against MDA-MB-231, SW-620 and HepG2 human cancer cell lines. Compound 4 showed cytotoxic activities.
Asunto(s)
Antineoplásicos Fitogénicos , Picrasma , Hojas de la Planta , Cuassinas , Humanos , Estructura Molecular , Picrasma/química , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/aislamiento & purificación , Hojas de la Planta/química , Línea Celular Tumoral , Cuassinas/farmacología , Cuassinas/aislamiento & purificación , Cuassinas/química , Fitoquímicos/farmacología , Fitoquímicos/aislamiento & purificación , Tallos de la Planta/química , Pueblos del Este de AsiaRESUMEN
Eight previously undescribed diterpenoids, caesamins A-H (1-8), were separated and identified from the seeds of Caesalpinia minax Hance. Their structures were characterized by extensive spectroscopic data and X-ray crystallographic analysis. Structurally, caesamin A (1) is the first cassane-type diterpenoid with a C23 carbon skeleton containing an unusual isopropyl. Caesamin F (6) represents the first example of cleistanthane diterpenoid from the genus Caesalpinia. Caesamins B (2) and F (6) exhibited inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages with IC50 values of 45.67 ± 0.92 and 42.99 ± 0.24 µM, comparable to positive control 43.69 ± 2.62 µM of NG-Monomethyl-L-arginine. Furthermore, the chemotaxonomic significance of the isolates was discussed.
Asunto(s)
Caesalpinia , Diterpenos , Óxido Nítrico , Semillas , Caesalpinia/química , Diterpenos/química , Diterpenos/farmacología , Diterpenos/aislamiento & purificación , Ratones , Semillas/química , Animales , Células RAW 264.7 , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico/biosíntesis , Estructura Molecular , Lipopolisacáridos/farmacología , Lipopolisacáridos/antagonistas & inhibidores , Macrófagos/efectos de los fármacos , Relación Estructura-Actividad , Relación Dosis-Respuesta a DrogaRESUMEN
Two new prostaglandin-like compounds callicarboric acids A-B (1-2), along with six known compounds (3-8) were isolated from the stems of Callicarpa arborea Roxb. Their structures were determined with the help of modern spectroscopic techniques such as NMR, UV, IR, HR-ESI-MS, ECD, and ORD with the assistance of quantum chemical calculations. Compound 1 exhibited remarkable anti-NLRP3 inflammasome activation potential, demonstrating an IC50 value of 0.74â µM. Additionally, by reducing GSDMD-NT production, inhibiting caspase-1 activation, and suppressing IL-1ß secretion, it effectively mitigated NLRP3 inflammasome-induced pyroptosis in J774A.1 cells. These findings indicate that compound 1 possesses the capability to be a valuable candidate for further research and development as an NLRP3 inflammasome inhibitor.
Asunto(s)
Callicarpa , Inflamasomas , Proteína con Dominio Pirina 3 de la Familia NLR , Prostaglandinas/farmacología , PiroptosisRESUMEN
Three new compounds callicarpenoids A-C (1-3), were isolated from the stems of Callicarpa arborea Roxb together with fifteen known compounds (4-18). The structures of these compounds were elucidated using advanced spectroscopic techniques, including 1D and 2D NMR, UV, IR, HR-ESI-MS, ECD, ORD, and quantum chemical calculations. Compound 3, a rare rearranged diterpenoid with a fused 5/6-ring system demonstrated strong potential as an inhibitor of the NLRP3 inflammasome activation with an IC50 value of 3.153â µM. It effectively reduced GSDMD-NT production, inhibited caspase-1 activation, and suppressed IL-1ß secretion, thereby mitigating NLRP3 inflammasome-induced pyroptosis in J774A.1 cells. These findings suggest that compound 3 warrants further research and development as a promising NLRP3 inflammasome inhibitor.
Asunto(s)
Callicarpa , Diterpenos de Tipo Clerodano , Inflamasomas , Proteína con Dominio Pirina 3 de la Familia NLR , Diterpenos de Tipo Clerodano/farmacología , Callicarpa/química , Espectroscopía de Resonancia MagnéticaRESUMEN
Eleven diterpenoids, wulfenioidins D-N (1-11), classified into five distinct carbon skeletons with one unreported framework, and four modified abietane diterpenoids were isolated from the whole plant of Orthosiphon wulfenioides. The structures and absolute configurations were characterized by spectroscopic methods, single-crystal X-ray diffraction, and electronic circular dichroism analyses. Compounds 3 and 5 exhibited activity against Zika virus (ZIKV) with EC50 values of 8.07 and 8.50 µM, respectively, and showed no significant cytotoxicity toward Vero cells at 100 µM. Western blot and immunofluorescence experiments showed that compounds 3 and 5 interfered with the replication of the ZIKV by inhibiting the expression of the ZIKV envelope (E) protein.
Asunto(s)
Diterpenos , Orthosiphon , Infección por el Virus Zika , Virus Zika , Animales , Chlorocebus aethiops , Células Vero , Diterpenos/química , Estructura MolecularRESUMEN
Wulfenioidones A - K (1-11) were abietane diterpenoids with highly oxidized 6/6/6 aromatic tricyclic skeleton isolated from the whole plant of Orthosiphon wulfenioides, and their planar structures and absolute configurations were elucidated by spectroscopic data interpretation, electronic circular dichroism calculation as well as X-ray crystallography analysis. Bioactivity screening indicated that compounds 1-4, 6 and 8 exhibited lactate dehydrogenase (LDH) inhibition effect with IC50 values ranging from 0.23 to 3.43 µM by preventing the mononuclear macrophage cell pyroptosis induced by double signal stimulation of LPS and nigericin. Western Blot analyses of Caspase-1 and IL-1ß down-regulation exhibited that compound 1 could selectively inhibit NLRP3 inflammasome, and the cell morphological observation further supported that compound 1 prevented macrophage cell pyroptosis.
Asunto(s)
Inflamasomas , Orthosiphon , Proteína con Dominio Pirina 3 de la Familia NLR , Abietanos/farmacología , Abietanos/química , MacrófagosRESUMEN
Four new norceanothane-type triterpenes, cyclopalin A-D (1-4), and sixteen known compounds (5-20) were obtained from the fruits of Cyclocarya paliurus. Their structures were determined by spectroscopic data, experimental electronic circular dichroism (ECD) and X-ray single crystal analyses. All isolated compounds were assayed for their anti-HIV-1IIIB activity. Compound 18 exhibited potent anti-HIV-1IIIB activity with an EC50 value of 1.32 µM (SI = 151.52).
Asunto(s)
Juglandaceae , Triterpenos , Triterpenos/química , Frutas , Análisis Espectral , Juglandaceae/química , Hojas de la Planta/químicaRESUMEN
Persistent activation of hepatic gluconeogenesis is a main cause of fasting hyperglycemia in patients with type 2 diabetes (T2D), and the salt-induced kinase 1 (SIK1) acts as a key modulator in regulating hepatic gluconeogenesis. Recently, we first reported phanginin A (PA, 1), a natural cassane diterpenoid isolated from the seeds of Caesalpinia sappan, exhibited potent anti-diabetic effect through activation of SIK1 and increasing PDE4 activity to inhibit hepatic gluconeogenesis pathway by suppressing the cAMP/PKA/CREB pathway in the liver. In present study, we designed and prepared 25 PA derivatives and their structure-activity relationship (SAR) for gluconeogenesis inhibitory activity were established. Among them, compound 7 exhibited remarkable inhibitory activity on hepatic gluconeogenesis by enhancing the SIK1 phosphorylation and ameliorated the hyperglyceamia of type 2 diabetic mice. Our results supported that compound 7 could be served as a potential candidate for the treatment of T2D.
Asunto(s)
Diabetes Mellitus Experimental , Diabetes Mellitus Tipo 2 , Animales , Diabetes Mellitus Experimental/inducido químicamente , Diabetes Mellitus Experimental/tratamiento farmacológico , Diabetes Mellitus Experimental/metabolismo , Diabetes Mellitus Tipo 2/tratamiento farmacológico , Diabetes Mellitus Tipo 2/metabolismo , Gluconeogénesis , Hígado , Ratones , Proteínas Serina-Treonina Quinasas , Transducción de SeñalRESUMEN
Ten previously undescribed cassane diterpenoids, cassabonducins A-J, and eleven known compounds were isolated from the seeds of Caesalpinia bonduc. The structures of the undescribed compounds were elucidated by extensive analysis of spectroscopic data (IR, HRESIMS, and 1H, 13C and 2D NMR) and their absolute configurations were determined by the ECD data and single-crystal X-ray diffraction analysis. ε-Caesalpin-â ¦ was obtained from natural resources for the first time. Cassabonducin A possessed noteworthy inhibitory activity against LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages with IC50 value of 6.12 µM. Cassabonducin D and neocaesalpin N showed moderate α-glucosidase inhibition at the concentration of 50 µM with inhibitory capacities of 47.17% and 43.83%, respectively.
Asunto(s)
Caesalpinia , Diterpenos , Diterpenos/farmacología , Espectroscopía de Resonancia Magnética , Estructura Molecular , Óxido Nítrico , Semillas , alfa-GlucosidasasRESUMEN
A phytochemical study on the stem bark of Metasequoia glyptostroboides led to the isolation of sixty-one diterpenoids and sesquiterpenoids, including seventeen previously undescribed compounds, metaglyptins A-Q. Their structures were elucidated by extensive analysis of spectroscopic data (IR, UV, HRESIMS, and 1H, 13C and 2D NMR). The absolute configurations of metaglyptins I, J, and O were determined by the ECD data and single-crystal X-ray diffraction analysis. The undescribed compounds were evaluated for their cytotoxicity against HeLa, AGS, and MDA-MB-231 cancer cell lines. The results revealed that metaglyptin A exhibited moderate cytotoxicity against MDA-MB-231â¯cell line with IC50 value of 20.02⯵M.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Cupressaceae/química , Diterpenos/farmacología , Corteza de la Planta/química , Tallos de la Planta/química , Sesquiterpenos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Cristalografía por Rayos X , Diterpenos/química , Diterpenos/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Células HeLa , Humanos , Modelos Moleculares , Conformación Molecular , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Relación Estructura-ActividadRESUMEN
A rare carotane-type sesquiterpenoid, forkienin A (1), a new eudesmane-type sesquiterpenoid, forkienin B (2), and a new natural eudesmane-type sesquiterpenoid, forkienin C (3), were isolated from the twigs and leaves of Fokienia hodginsii, along with eight known sesquiterpenoids. The structures of the new compounds were elucidated on the basis of their spectroscopic analysis, including 1D and 2D NMR methods. All compounds were evaluated for cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Hojas de la Planta/química , Tallos de la Planta/química , Sesquiterpenos de Eudesmano/aislamiento & purificación , Sesquiterpenos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Células HL-60 , Humanos , Estructura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacología , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacologíaRESUMEN
Five cassane diterpenes were isolated from the 95% ethanol extract of the seeds of Caesalpinia bonduc (Leguminosea) by a combination of various chromatographic methods, including silica gel, Sephadex LH-20, and semi-preparative HPLC. On the basis of spectroscopic techniques, their structures were identified as 3ß-acetoxy-cassa-12,14(17),15-trien-7ß-ol (1), caesalmin C (2), caesall E (3), caesalpinin MJ (4), and 1-deacetylcaesalmin C (5). Among them, compound 1 is a new compound and 2, 4, 5 were isolated from the plant for the first time.
Asunto(s)
Caesalpinia/química , Diterpenos/química , Semillas/química , Diterpenos/aislamiento & purificación , Estructura Molecular , Extractos Vegetales/químicaRESUMEN
Three rearranged labdane-type diterpenoids, hypophyllins A-C (1-3), and a caged labdane diterpenoid possessing a 8,9-dioxatricyclic[4.2.1.13,7]decane moiety, hypophyllin D (4), as well as two new biogenetically related diterpernoids, hypophyllins E (5) and F (6), were isolated from the aerial parts of Hypoestes phyllostachya "Rosea". The absolute configurations of 1-4 were determined by X-ray diffraction analysis. The plausible biogenetic pathway for 1-4 was also proposed. Compounds 4 and 5 showed potent vasorelaxant activity on endothelium-intact thoracic aorta rings precontracted with KCl.
Asunto(s)
Acanthaceae/química , Aorta Torácica/efectos de los fármacos , Diterpenos/farmacología , Endotelio Vascular/efectos de los fármacos , Vasodilatadores/farmacología , Animales , Diterpenos/química , Diterpenos/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Conformación Molecular , Componentes Aéreos de las Plantas/química , Cloruro de Potasio/farmacología , Ratas , Estereoisomerismo , Relación Estructura-Actividad , Vasodilatadores/química , Vasodilatadores/aislamiento & purificaciónRESUMEN
Phytochemical investigation of the flowers of Inula japonica led to isolation of nine sesquiterpenoids, inujaponins A-I, as well as eighteen known ones. These sesquiterpenoids belong to six skeletal-types, including eudesmane, 1,10-seco-eudesmane, germacrane, guaiane, 4,5-seco-guaiane, and pseudoguaiane sesquiterpenoids. Their structures were established by extensive spectroscopic analysis. The absolute configurations of inujaponin A, eupatolide, and deacetylovatifolin were determined by Cu-Kα X-ray crystallographic analysis. Most of the isolated compounds exhibited potent cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cancer cell lines, with IC50 values ranging from 1.57 to 22.58 µM. Some selected compounds also possessed significant inhibitory activity against LPS-induced NO production in RAW264.7 macrophages with IC50 values ranging from 1.42 to 8.99 µM.
Asunto(s)
Flores/química , Inula/química , Sesquiterpenos de Eudesmano/aislamiento & purificación , Animales , Cristalografía por Rayos X , Células HL-60 , Humanos , Concentración 50 Inhibidora , Lipopolisacáridos/farmacología , Macrófagos/efectos de los fármacos , Ratones , Conformación Molecular , Estructura Molecular , Óxido Nítrico/biosíntesis , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacología , Sesquiterpenos de Guayano/química , Sesquiterpenos de Guayano/aislamiento & purificación , Sesquiterpenos de Guayano/farmacologíaRESUMEN
Objective: To study the chemical constituents of Inula japonica. Methods: Silica gel, Sephadex LH-20,MCI and semipreparative HPLC were used to isolate and purify the constituents of Inula japonica,and the chemical structures were elucidated by chemical properties, MS and NMR analysis. Results: 14 compounds were isolated and their structures were identified as ivangustin( 1),1-acetoxy-6α-hydroxyeriolanolide( 2), 1ß-hydroxyalantolactone( 3),tomentosin( 4),11,13-dihydroinuchinenolide B( 5), britanlin A( 6),vomifoliol( 7), 17-hydroxy-16α-ent-kauran-19-oic acid( 8), 12-hydroxygeranylgeraniol ( 9), dihydroquercetin( 10), kaempferol( 11), quercetin( 12), dihydroconiferyl alcohol( 13) and fareanol( 14). Conclusion: Compounds 5,6,9,13 and 14 are isolated from this plant for the first time.