RESUMEN
Three new flavan derivatives including two methylene-linked flavan-3-ol dimers, bis(8-epiafzelechinyl)methane (1), and 8,8-(epiafzelechin-afzelechin)methane (2), a flavan-3-ol monomer, (-)-3-O-acetyl-epiafzelechin (3) and four known related compounds (4-7) were isolated from the leaves and stems of Cassia nodosa. Their structures were elucidated by extensive spectroscopic analyses and CD data. The isolates were evaluated for their antioxidant, α-glucosidase inhibitory, cytotoxic and neuroinflammatory activities, and compound 3 exhibited remarkable radical scavenging activities in both the DPPH and ABTS models with IC50 values of 2.65±1.25, and 4.78±0.91 µg/mL, respectively.
RESUMEN
In this study, a transversal ultrasonic vibration-assisted riveting (TUVAR) process was developed to improve the uniformity of CFRP riveted lap joint interference-fit size, which provided a possibility for the quantization of riveted joint interference-fit sizes. The relationship between the process parameters of vibration amplitude, vibration duration, and roughness with interference-fit sizes by algorithms, through the minimum coefficient variance of interference-fit size (ICV-min) to confirm the riveting process parameters of the quantized average interference-fit sizes (IA). The experimental verification results showed that the mean absolute percentage error of measured IA and predicted IA is less than 10%. Furthermore, the tensile tests were carried out to investigate the effect of interference-fit size {1.4%, 1.6%, 1.8%, and 2.0%} on mechanical performances of CFRP riveted lap joints by TUVAR, and the tensile strength presents first-up then down with the interference-fit size increase, the maximum ultimate tensile strength is the riveted lap joint with the interference-fit size of 2.0%. Hence, the quantitative optimization method can well predict the riveting process parameters corresponding to the most uniform interference-fit size.
RESUMEN
Horsfiequinone G (1), a dimeric diarylpropane featuring an unprecedentedly oxo-6/7/6 fused ring system, a new flavane, horsfielenide F (2), three naturally occurring spirocyclic monomers containing all-carbon quaternary centers, horspirotone A (3), horspirotone B (4), and methyl spirobroussonin B (5), along with horsfiequinone A (6) were isolated from Horsfieldia kingii. Their structures and absolute configurations were determined by the inspection of extensive spectroscopic data and electronic circular dichroism (ECD) calculations. Biological evaluations of these isolates revealed that compounds 1 - 3 and 5 - 6 exhibited specifically immunosuppressive activities against Con A-induced T lymphocytes with IC50 values ranging from 2.07 to 12.34 µM (selectivity indices = 2.3-25.2). Compound 1 also suppressed the secretion of inflammatory factors like IL-1ß and IL-6 in RAW264.7 cells which could present a new class of nonsteroidal anti-inflammatory agent. Finally, the primary structure-activity relationship (SAR) was also discussed.
Asunto(s)
Antiinflamatorios no Esteroideos , Inmunosupresores , Antiinflamatorios no Esteroideos/farmacología , Carbono , Dicroismo Circular , Inmunosupresores/farmacología , Estructura Molecular , Relación Estructura-ActividadRESUMEN
Two new bibenzyl-phenylpropane hybrids, dendrophenols A and B (1 and 2), along with nine known bibenzyls, were isolated from the aerial part of Dendrobium devonianum Paxt. Their structures were determined by extensive spectroscopic methods and methylation. Bioassays revealed that compounds 1-9 were specifically immunosuppressive to T lymphocytes with IC50 values ranging from 0.41 to 9.4â µM, of which compounds 1 (IC50 =1.62â µM) and 2 (IC50 =0.41â µM) were promising immunosuppressive agents for T lymphocytes with the selectivity indices of 19.9 and 79.5, respectively.
Asunto(s)
Bibencilos , Dendrobium , Bibencilos/farmacología , Bibencilos/química , Dendrobium/química , Depuradores de Radicales Libres/química , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
Two new isopentenyl bibenzyls, denchrysotonols A and B (1-2), along with 26 known phenolic compounds, were isolated from the stems of cultivated Dendrobium chrysotoxum Lindl. Their chemical structures were clearly elucidated by extensive spectroscopic analysis. Biological evaluation of isolated compounds revealed that phenanthrenes (14, 16-17, 20, and 22) and fluorenone 25 exhibited anti-inflammatory activities which inhibited nitric oxide (NO) production in LPS-activated RAW264.7 macrophages with the IC50 values ranging from 9.4 to 32.5â µM. Moreover, bibenzyls (1-2 and 7) showed good anti-proliferative activities against triple-negative breast cancer (TNBC) cells (HCC1806, MDA-MB-231, and MB-MB-468) with the IC50 values ranging from 8.1 to 18.6â µM, of which 1 and 2 seemed preferentially inhibit MDA-MB-231 cells.
Asunto(s)
Bibencilos , Dendrobium , Antiinflamatorios/farmacología , Bibencilos/química , Bibencilos/farmacología , Dendrobium/química , Macrófagos , Estructura Molecular , Fenoles/farmacologíaRESUMEN
Three new diarylpropanes (1-3), including two diarylpropane glycosides, and three known ones, were isolated from 70% aqueous acetone extract of the twigs and leaves of Horsfieldia kingii. Their structures were elucidated by spectroscopic analysis. Bioactive evaluation of inhibition on DDC enzyme assay showed that the new compounds were inactive.
Asunto(s)
Flavonoides/aislamiento & purificación , Myristicaceae/química , Inhibidores de Descarboxilasas de Aminoácidos Aromáticos/química , Inhibidores de Descarboxilasas de Aminoácidos Aromáticos/farmacología , Dopa-Decarboxilasa/metabolismo , Flavonoides/química , Flavonoides/farmacología , Glicósidos/química , Glicósidos/farmacología , Humanos , Extractos Vegetales/química , Hojas de la Planta/química , Espectroscopía de Protones por Resonancia MagnéticaRESUMEN
Chemical investigation of the twigs of Cryptocarya impressinervia yielded 23 known compounds including 8 lignans, 3 phenylpropionates, 1 xanthone, 3 flavonoids, 1 phenylpropanoid, 1 substitued phenol, 1 triterpenoid, 3 sterols and 2 aliphatic compounds. All the compounds was isolated from C. impressinervia for the first time. 9,9'-O-Di-feruloyl-(-)-secoisolariciresinol (1) displayed significant cytotoxic activities on five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW-480), with IC50 values of 3.58, 4.55, 6.39, 5.09 and 4.80 µM, respectively. Rhusemialin A (2) showed significant activity against HL-60 with IC50 of 3.69 µM. Dihydrosinapyl ferulate (3) displayed moderate cytotoxic activities against five tested human cancer cell lines. To the best of our knowledge, this is the first report on the constituents of C. impressinervia and cytotoxic activities of compounds 1-3 on the tested cancer cell lines.
Asunto(s)
Cryptocarya/química , Lignanos/farmacología , Antineoplásicos/farmacología , Antineoplásicos Fitogénicos/química , Butileno Glicoles/farmacología , Muerte Celular/efectos de los fármacos , Línea Celular Tumoral , Flavonoides/química , Humanos , Concentración 50 Inhibidora , Lignanos/química , Triterpenos/química , Triterpenos/farmacologíaRESUMEN
Twenty-seven compounds, including a new diarypropane and two new lignans were isolated from the twigs and leaves of Endocomia macrocoma. Their structures were elucidated by spectroscopic analysis. Cytotoxicity evaluation of the new compounds against five human tumor lines showed no inhibitory effects.[Formula: see text].
Asunto(s)
Lignanos/aislamiento & purificación , Myristicaceae/química , Propano/aislamiento & purificación , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Lignanos/química , Lignanos/farmacología , Estructura Molecular , Extractos Vegetales/química , Hojas de la Planta/química , Propano/química , Propano/farmacologíaRESUMEN
Two new eremophilane sesquiterpenoides, 6α,9α-dihydroxyeremophilenolide (1), and 1ß,10ß-dihydroxyeremophilenolide (2), along with ten known eremophilane sesquiterpenoides (3-12) were isolated from the aerial parts of Ligularia dictyoneura (Franch.) Hand.-Mazz. Their structures were elucidated by means of extensive spectroscopic analysis. Compounds 3-6 were assessed for their cytotoxicity against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW-480), and the result showed that they had no activity.
Asunto(s)
Ligularia/química , Sesquiterpenos Policíclicos/química , Sesquiterpenos Policíclicos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Estructura Molecular , Componentes Aéreos de las Plantas/química , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
Twelve dihydrostilbenes (including five new analogues) were prepared by the Witting-Hornor reaction from appropriate aromatic aldehydes and phosphonate esters, followed by hydrogenation in five steps. The in vitro inhibition activity against human neutrophil elastase (HNE) of these dihydrostilbenes was evaluated, and three 1,2-dihydroxylated dihydrostilbenes (6b, 6j, and 6l) exhibited stronger inhibitory activity against HNE than other analogues.
Asunto(s)
Dihidrostilbenoides , Elastasa de Leucocito , Humanos , Estructura MolecularRESUMEN
Horisfieldones A (1) and B (2), two dimeric diarylpropanes featuring an unprecedentedly aromatic ring-contracted framework, were isolated from Horsfieldia kingii. Their structures and absolute configurations were determined by the inspection of extensive spectroscopic data and electronic circular dichroism calculations. Molecular modeling analysis, in vitro enzyme-based bioassays, and structure-activity relationship analysis of these isolates revealed that (+)-1 (IC50 = 35.1 ± 3.9 µM, SI > 11.4) could present a new class of human DOPA decarboxylase inhibitor.
Asunto(s)
Dopa-Decarboxilasa/farmacología , Propano/farmacología , Dicroismo Circular , Dopa-Decarboxilasa/química , Humanos , Concentración 50 Inhibidora , Modelos Moleculares , Estructura Molecular , Propano/análogos & derivados , Propano/química , Relación Estructura-ActividadRESUMEN
Two new phenylpropanoid esters bobulretulates A (1) and B (2), together with eleven known compounds, were isolated from the whole plants of Bulbophyllum retusiusculum. Their structures were elucidated by means of extensive spectroscopic analysis.
Asunto(s)
Orchidaceae/química , Fenilpropionatos/aislamiento & purificación , Ésteres/química , Ésteres/aislamiento & purificación , Fenilpropionatos/químicaRESUMEN
Two new picrotoxane-type sesquiterpenoid lactones, dendrowillins A (1) and B (2), together with five known sesquiterpenoids, (-)-picrotin (3), α-dihydropicrotoxinin (4), dendronobilin B (5), amoenin (6), and (-)-10ß,13,14-trihydroxyalloaromadendrane (7), were isolated from the whole plants of Dendrobium williamsonii. Their structures were elucidated by means of extensive spectroscopic analysis.
Asunto(s)
Dendrobium/química , Lactonas/química , Sesquiterpenos/química , Estructura MolecularRESUMEN
A new galloyl glucoside, 2,6-di-O-acetyl 1-O-galloyl ß-D-glucose (1), along with five known phenolic compounds were isolated from the whole plants of Lotus corniculatus. Their structures were elucidated by means of extensive spectroscopic analysis. Compound 1 was assessed for its cytotoxicity against five human tumour lines (HL-60, SMMC-7721, A-549, MCF-7 and SW-480), and the result showed that it had no activity.
Asunto(s)
Glucósidos/química , Lotus/química , Extractos Vegetales/química , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales , Glucósidos/aislamiento & purificación , Glucósidos/farmacología , Humanos , Taninos Hidrolizables , Estructura Molecular , Fenoles/química , Fenoles/aislamiento & purificación , Análisis EspectralRESUMEN
Two new dibenzylbutyrolactol lignans and three known dibenzylbutyrolactone lignans were isolated from the twigs and leaves of Horsfieldia kingii. Their structures were elucidated by spectroscopic analysis. Cytotoxicity evaluation of these compounds against five human tumour lines showed no inhibitory effects.
Asunto(s)
Lignanos/aislamiento & purificación , Myristicaceae/química , Extractos Vegetales/química , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Lignanos/química , Lignanos/toxicidad , Estructura Molecular , Hojas de la Planta/química , Análisis EspectralRESUMEN
A new neolignan, 5-(3â³-acetoxypropyl)-2-(4'-hydroxy-3'-methoxyphenyl)-7-methoxy-3-methylbenzofuran (1) along with nine analogues were isolated from the thorns of Gleditsia japonica var. delavayi by solvent extraction and repeated column chromatography. Their structures were elucidated by means of extensive spectroscopic analysis including 1D, 2D-NMR techniques and HR-ESIMS. All the isolates were reported for the first time from this species.
Asunto(s)
Gleditsia/química , Lignanos/aislamiento & purificación , Lignanos/química , Estructura Molecular , Estructuras de las Plantas/química , Análisis EspectralRESUMEN
A new phenanthrene, bobulretin A (1), and a new 9,10-dihydrophenanthrene, bobulretin B (2) along with four known bibenzyls (3-6) were isolated from the whole plants of Bulbophyllum retusiusculum. Their structures were elucidated by means of extensive spectroscopic analysis. Bobulretin B (2), isolated as enantiomer mixture with unequal proportions, was verified by analysis on a chiral OD-H HPLC column. Compounds 1, 3 and 4 were evaluated for their α-glucosidase inhibitory activity. Neither of them showed obvious activity.
Asunto(s)
Orchidaceae/química , Fenantrenos/química , Bibencilos/química , Bibencilos/aislamiento & purificación , China , Estructura Molecular , Fenantrenos/aislamiento & purificación , alfa-GlucosidasasRESUMEN
A new (propylphenyl)bibenzyl derivative, dendrowillol A (1), along with 22 known compounds were isolated from the whole plants of Dendrobium williamsonii. Their structures were elucidated by means of extensive spectroscopic analysis. Cytotoxicity evaluation against five human tumour lines showed that all the compounds tested displayed very weak cytotoxicity when compared with the positive control taxol, but selective inhibitory effects on HL-60 for several compounds tested were observed, with IC50 values ranging from 4.48 to 11.04 µM.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Bibencilos/farmacología , Dendrobium/química , Antineoplásicos Fitogénicos/química , Compuestos de Bencilo/farmacología , Bibencilos/química , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales , Células HL-60 , Humanos , Concentración 50 Inhibidora , Lignanos/química , Lignanos/farmacología , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
Five compounds, including a new dimeric diarylpropane, were isolated from the petroleum ether extract of the twigs and leaves of Horsfieldia tetratepala. The structures of these compounds were elucidated by spectroscopic analysis. Moreover, the antiproliferative activities of these compounds were tested on cancer cell lines, but none is active.