RESUMEN
(±)-Patulignans A-C (1-3), three unique pairs of lignan enantiomers were isolated from the leaves of Melicope patulinervia. Patulignan A (1) possesses an unprecedented dimethyloxonane moiety in nature, meanwhile patulignans B (2) and C (3) are epimers carrying a novel dimethyl-1,6-dioxaspiro[4.5]decane skeleton. Their structures were established by spectroscopy methods and electronic circular dichroism (ECD) calculations. Compounds 1-3 showed significant inhibitory activity against α-glucosidase.
Asunto(s)
RutaceaeRESUMEN
Six new obovatol trimeric neolignans, houpulignans A-F (1-6) were isolated from the leaves of Magnolia officinalis var. biloba. Their structures were determined on the basis of the interpretation of HRESIMS, NMR data, and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 are the first examples of neolignans derived from three units of obovatol bearing a rare 1,4-benzodioxepane moiety. Compound 3 possesses a benzodihydropyran ring, meanwhile three units of obovatol in 4-6 are connected by an alkyl chain. Compounds 1-3 inhibited NO production in LPS-stimulated RAW264.7 cells with IC50 values of 8.01, 20.21, and 4.05 µM, respectively.
Asunto(s)
Compuestos de Bifenilo/química , Compuestos de Bifenilo/farmacología , Lignanos/química , Lignanos/farmacología , Magnolia/química , Óxido Nítrico/antagonistas & inhibidores , Éteres Fenílicos/química , Éteres Fenílicos/farmacología , Animales , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Ratones , Óxido Nítrico/metabolismo , Extractos Vegetales/química , Extractos Vegetales/farmacología , Hojas de la Planta/química , Células RAW 264.7RESUMEN
Five new phloroglucinol derivatives, eucalyptins C-G (1-5), together with 13 known analogues (6-18) were isolated from the fruits of Eucalyptus globulus. The structures and absolute configurations of 1-5 were established by means of spectroscopic data analysis, computational calculation methods, and single-crystal X-ray diffraction. Compounds 1-18 were investigated for their immunosuppressive effects in vitro, and 1, 2, 6, and 7 displayed moderate inhibitory activities with IC50 values of 11.8, 10.2, 18.2, and 19.1 µM, respectively. The stimulation index (SI) of 1 was 64.2 and was compared to that of cyclosporine A (SI = 149.57). Further study demonstrated that 1 exhibited an immunosuppressive effect through inducing apoptosis and inhibiting cytokine secretion.
Asunto(s)
Eucalyptus/química , Inmunosupresores/farmacología , Floroglucinol/farmacología , Animales , Células Cultivadas , Cristalografía por Rayos X , Citocinas/metabolismo , Humanos , Inmunosupresores/química , Concentración 50 Inhibidora , Ratones , Ratones Endogámicos BALB C , Estructura Molecular , Floroglucinol/químicaRESUMEN
One new compound, 4,7-dihydroxy-2-hydroxymethyl-5,6-dimethoxyanthraquinone (1), along with eight known compounds (2-9) were isolated from the methanol extracts of the aerial parts of Chamaecrista pumila (Lam.) K. Larsen. Their chemical structure was determined based on spectroscopic data interpretation and comparison with the reported data. The inhibitory effects of them on α-amylase and α-glucosidase were performed. The results showed that compounds 4, 6, 8, and 9 against potent α-glucosidase with the inhibition values of 98.14 ± 0.05, 98.19 ± 0.04, 97.01 ± 0.49, 84.43 ± 0.6% at 50 µM, respectively. Compounds 4 and 6 displayed significance against α-amylase at 200 µM with inhibition values of 22.35 ± 1.10 and 60.47 ± 0.91%.
Asunto(s)
Chamaecrista , Inhibidores de Glicósido Hidrolasas , Inhibidores de Glicósido Hidrolasas/farmacología , Inhibidores de Glicósido Hidrolasas/química , Hipoglucemiantes/farmacología , alfa-Glucosidasas/química , alfa-Amilasas/química , Extractos Vegetales/química , Componentes Aéreos de las Plantas/químicaRESUMEN
Four new lignans, patulinones A-D (1-4) and three new acetophenone derivatives, patulinones E-G (5-7) were isolated from the leaves of Melicope patulinervia. Their structures were elucidated on the basis of the interpretation of HR-ESIMS, NMR, CD data. All the isolated compounds were evaluated for α-glucosidase inhibitory activity. Of the isolates, compound 4 was found to exhibit the strongest inhibition against α-glucosidase with IC50 value of 6.02 ± 0.46 µM.
Asunto(s)
Acetofenonas/farmacología , Inhibidores de Glicósido Hidrolasas/farmacología , Lignanos/farmacología , Rutaceae/química , Acetofenonas/aislamiento & purificación , China , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Lignanos/aislamiento & purificación , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Hojas de la Planta/químicaRESUMEN
Six new oligomeric neolignans including two trimeric neolignans (1 and 2) and four dimeric neolignans (3-6) were isolated from the leaves of Magnolia officinalis var. biloba. Their structures were determined based on HR-ESIMS and NMR data, as well as electronic circular dichroism (ECD) calculations. Compound 1 is formed from two obovatol moieties directly linked to an aromatic ring of the remaining obovatol moiety, which is an unprecedented type of linkage between monomers. All isolates were assessed for their inhibitory effects on NO production in LPS-stimulated RAW 264.7 macrophage cells. Compounds 1 and 3 showed significantly inhibitory activities with IC50 values of 6.04 and 3.26 µmol·L-1, respectively.