RESUMEN

Two new prenylated flavonoids named sinoflavonoids NJ and NK (1-2), along with ten known compounds were isolated from the fruits of Podophyllum hexandrum Royle. The chemical structures were determined through NMR spectroscopic data and MS analysis. Sinoflavonoid NJ (1) with an unusual 5,11-dioxabenzo[b]fluoren-10-one skeleton was firstly reported from Berberidaceae. The isolated flavonoids were tested with LPS-induced RAW 264.7 mouse macrophages model for their anti-inflammatory activity. Sinoflavonoid NJ (1) showed the most potent inhibition on nitric oxide production with IC50 value as 0.06 µM.

Asunto(s)

Berberidaceae , Flavonoides , Animales , Ratones , Flavonoides/química , Frutas/química , Berberidaceae/química , Antiinflamatorios/farmacología , Antiinflamatorios/análisis

RESUMEN

One new dibenzyltyrolactone lignan dysoslignan A (1), three new arylnaphthalide lignans dysoslignan B-C (2-4), along with fourteen known metabolites (5-18), were isolated from the roots and rhizomes of Dysosma versipellis. Their structures and stereochemistry were determined from analysis of NMR spectroscopic and circular dichroism (CD) data. Compound 2 represents the first report of naturally occurring arylnaphthalide lignan triglycoside. The cytotoxic activities of all isolated compounds were evaluated against A-549 and SMMC-7721 cell lines. Compounds 7-10 and 14-16 were more toxic than cisplatin in two tumor cell lines. This investigation clarifies the potential effective substance basis of D. versipellis in tumor treatment.

Asunto(s)

Berberidaceae , Lignanos , Raíces de Plantas , Rizoma , Células A549 , Antineoplásicos/efectos adversos , Antineoplásicos/toxicidad , Berberidaceae/química , Berberidaceae/metabolismo , Dicroismo Circular , Cisplatino/efectos adversos , Cisplatino/toxicidad , Lignanos/química , Lignanos/aislamiento & purificación , Lignanos/metabolismo , Lignanos/toxicidad , Espectroscopía de Resonancia Magnética , Neoplasias/tratamiento farmacológico , Raíces de Plantas/química , Raíces de Plantas/metabolismo , Rizoma/química , Rizoma/metabolismo , Línea Celular Tumoral

RESUMEN

Six new flavonols, including four glucosylated flavonols (dysosmaflavonoid A-D), one phenylpropanoid-substituted flavonol (dysosmaflavonoid E), and one phenyl-substituted flavonol (dysosmaflavonoid F), together with five known analogues, were isolated from the roots and rhizomes of Dysosma versipellis. Their structures were elucidated by comprehensive analysis of their NMR, IR, UV, HRESIMS, and HPLC data. The antioxidant activities of all isolated compounds were examined by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay. Compounds 2, 3, 5-8, and 12 exhibited significant DPPH scavenging capacity with IC50 values of 33.95, 39.02, 31.17, 32.79, 31.85, 30.48, and 23.75 µM, respectively, in comparison with Trolox (IC50, 15.80 µM). Compound 12 displayed more potent DPPH radical scavenging activity than prenylated and (or) glucosided derivatives (2-4, or 10). The preliminary structure-activity relationship showed that the catechol structure in flavonol is essential for DPPH radical scavenging effect.

Asunto(s)

Berberidaceae , Flavonoles , Flavonoles/farmacología , Flavonoles/química , Estructura Molecular , Antioxidantes/farmacología , Antioxidantes/química , Berberidaceae/química , Relación Estructura-Actividad , Depuradores de Radicales Libres/química , Compuestos de Bifenilo , Picratos/química

RESUMEN

Two new pyrrole alkaloids methyl-E-mangolamide (1) and methyl-Z-mangolamide (2), four new megastigmane glycosides nandinamegastigmanes I-IV (3-6), and eight known compounds (7-14) were isolated from the methanol extract of the fruits of Nandina domestica. The structures of the new compounds were elucidated based on chemical and spectroscopic evidence. The absolute stereochemistry of nandinamegastigmane I (3) was established upon comparing the experimental and predicted electronic circular dichroism (ECD) data. Among the isolated compounds, 1 and 2 showed cell death-inducing activity on the Adriamycin-treated HeLa cells. In addition, one of the mechanisms for cell death-inducing activity of 1 and 2 was suggested as inhibition of P-glycoprotein.

Asunto(s)

Subfamilia B de Transportador de Casetes de Unión a ATP/antagonistas & inhibidores , Alcaloides/farmacología , Berberidaceae/química , Muerte Celular/efectos de los fármacos , Alcaloides/aislamiento & purificación , Frutas/química , Glicósidos/aislamiento & purificación , Células HeLa , Humanos , Japón , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología

RESUMEN

Two new isoquinoline alkaloids, 6 R,6aS-N-nantenine Nß-oxide (1), 6S,6aS-N-nantenine Nα-oxide (2), along with nine known alkaloids, nantenine (3), oxonantenine (4), protopine (5), nornantenine (6), N-methyl-laurotetanine (7), isocorydine (8), O-methyflavinantine (9), N-methyl-2,3,6-trimethoxymorphinan-dien-7-one Nß-oxide (10) and (+)-10-O-methylhernovine Nß-oxide (11) were isolated from the seeds of Nandina domestica. Their structures were elucidated by extensive analyses of spectroscopic data (IR, UV, HRESIMS, 1 D and 2 D NMR), ECD calculation and comparison with the related literatures. In addition, the cytotoxicity against A549 cells of these alkaloids was determined by the MTT assay.

Asunto(s)

Alcaloides , Berberidaceae , Isoquinolinas/farmacología , Células A549 , Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Berberidaceae/química , Humanos , Isoquinolinas/aislamiento & purificación , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Extractos Vegetales , Semillas/química

RESUMEN

Two new flavonoid glucosides, sinoflavonoidgs A (1) and B (2), along with three known analogues 3-5, were isolated from the fruits of Sinopodophyllum hexandrum. Their structures were established on the basis of extensive spectroscopic (UV, IR, HR-ESI-MS, 1H-NMR, 13C-NMR, HSQC, HMBC) and chromatographic (HPLC) analysis. The isolation of compounds 1-2 represents the first report of ring B-glucosided flavonoids from the genus Sinopodophyllum. The cytotoxic activities of all isolated compounds were evaluated in comparison with etoposide against four cell lines (MCF-7, HepG2, HeLa, KB). The antioxidant activities of all isolated compounds were examined by DPPH free radical-scavenging assay. The preliminary structure-activity relationships showed that the glycosilation of 3-methoxyquercetin at C-3' resulted in a greater decrease of cytotoxic and antioxidant activity.

Asunto(s)

Berberidaceae/química , Flavonoides/aislamiento & purificación , Frutas/química , Glucósidos/aislamiento & purificación , Espectroscopía de Resonancia Magnética con Carbono-13 , Línea Celular Tumoral , Cromatografía Líquida de Alta Presión , Flavonoides/química , Glucósidos/química , Humanos , Concentración 50 Inhibidora , Espectroscopía de Protones por Resonancia Magnética

RESUMEN

The first racemic total synthesis of the isoquinoline-benzylisoquinoline alkaloid muraricine is reported herein. Pharmacological characterization identified muraricine as a moderate inhibitor of P-glycoprotein, a crucial factor of multidrug resistance in cancer. When combined with vincristine, muraricine partly reversed the chemoresistance of vincristine-resistant leukemia cells at a nontoxic concentration. Furthermore, no cytotoxic effects on noncancerous human cells in therapeutically relevant concentrations were observed.

Asunto(s)

Miembro 1 de la Subfamilia B de Casetes de Unión a ATP/antagonistas & inhibidores , Alcaloides/farmacología , Antineoplásicos Fitogénicos/farmacología , Isoquinolinas/farmacología , Alcaloides/síntesis química , Alcaloides/química , Antineoplásicos Fitogénicos/síntesis química , Antineoplásicos Fitogénicos/química , Berberidaceae/química , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Resistencia a Antineoplásicos/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Células Hep G2 , Células Endoteliales de la Vena Umbilical Humana/efectos de los fármacos , Humanos , Isoquinolinas/síntesis química , Isoquinolinas/química , Estructura Molecular , Relación Estructura-Actividad

RESUMEN

Dysosma pleiantha (Hance) Woodson is one of the endangered traditional Chinese medicinal herbs, highly valued for its medicinal properties by Taiwan's mountain tribes. The present study aims to develop an efficient protocol for callus biomass by optimizing suitable culture medium, carbon source culture condition, and enhanced production of pharmaceutically important podophyllotoxin, kaempferol, and quercetin from callus culture of D. pleiantha under the influence of different additives. Best callus induction was achieved in Gamborg's medium (B5) with 1 mg/L 2,4-dichlorophenoxyacetic acid (2,4-D) along with 0.2 mg/L kinetin under dark condition. Tender leaves of D. pleiantha showed the maximum of 86% callus induction among the different explants tested. Highest leaf callus proliferation was noted in B5 medium with 1 mg/L 2,4-D incubated under complete darkness. In addition, it was found that B5 medium with 1 mg/L 2,4-D along with 2 g/L peptone produced more leaf callus biomass and enhanced production of podophyllotoxin (16.3-fold), kaempferol (12.39-fold), and quercetin (5.03-fold) compared to control. Therefore, D. pleiantha callogenesis can provide an alternative source for enhanced production of secondary compounds regardless of the exploitation of its natural plant population.

Asunto(s)

Berberidaceae/química , Medicamentos Herbarios Chinos/metabolismo , Quempferoles/biosíntesis , Plantas Medicinales/química , Podofilotoxina/biosíntesis , Quercetina/biosíntesis , Berberidaceae/metabolismo , Medicamentos Herbarios Chinos/química , Quempferoles/química , Medicina Tradicional China , Estructura Molecular , Plantas Medicinales/metabolismo , Podofilotoxina/química , Quercetina/química

RESUMEN

The aim of this review is to collect together the results of the numerous studies over the last two decades on the pharmacological properties of palmatine published in scientific databases like Scopus and PubMed, which are scattered across different publications. Palmatine, an isoquinoline alkaloid from the class of protoberberines, is a yellow compound present in the extracts from different representatives of Berberidaceae, Papaveraceae, Ranunculaceae, and Menispermaceae. It has been extensively used in traditional medicine of Asia in the treatment of jaundice, liver-related diseases, hypertension, inflammation, and dysentery. New findings describe its possible applications in the treatment of civilization diseases like central nervous system-related problems. This review intends to let this alkaloid come out from the shade of a more frequently described alkaloid: berberine. The toxicity, pharmacokinetics, and biological activities of this protoberberine alkaloid will be developed in this work.

Asunto(s)

Berberidaceae/química , Alcaloides de Berberina/farmacocinética , Alcaloides de Berberina/uso terapéutico , Medicina Tradicional/métodos , Animales , Modelos Animales de Enfermedad , Perros , Humanos , Ratas

RESUMEN

Sixteen new prenylated flavonoids, sinoflavonoids P-Z (1-11) and sinoflavonoids NA-NE (12-16), were isolated from the fruit of Sinopodophyllum hexandrum, along with eight known analogues (17-24). Their structures were elucidated on the basis of extensive spectroscopic data (HR-ESI-MS, 1H-NMR, 13C-NMR, HSQC, HMBC). The cytotoxic activities of compounds 1-18, 20, and 22 were evaluated by MTT assay. Compound 6 showed the most potent cytotoxicity in MCF-7, and HepG2 cell lines, with IC50 values of 6.25 and 3.83 µM, respectively.

Asunto(s)

Berberidaceae/química , Flavonoides/química , Frutas/química , Supervivencia Celular/efectos de los fármacos , Flavonoides/farmacología , Células Hep G2 , Humanos , Concentración 50 Inhibidora , Células MCF-7

RESUMEN

Using the White as basic medium, the effects of the exogenous IBA and endophytic fungal elicitor on the growth of in vitro roots cultures of Dysosma versipellis and production of podophyllotoxin were investigated in this study. The results showed that the IBA and the endophytic fungus Zasmidium syzygii elicitor could increase the content of podophyllotoxin of in vitro roots of D. versipellis after 3 weeks. The White medium added with 3 mg·L~(-1) IBA induced the highest increase of podophyllotoxin(1 830.86 µg·g~(-1)), which was 2.07 folds greater than the control, and followed by 1.5 mg·L~(-1) IBA, fungal elicitor, 1 mg·L~(-1) IBA, 0.5 mg·L~(-1) IBA and 4.5 mg·L~(-1) IBA, which was 1.82, 1.71, 1.63, 1.43 and 1.1 folds greater than the control, respectively. The results also showed that the growth of roots was certain positively correlated with the change of IBA concentration. Therefore, 3 mg·L~(-1) IBA was the most suitable for the production of podophyllotoxin in the in vitro roots of D. versipellis, and the stimulating effect of Z. syzygii fungal elicitor was between 1.5 mg·L~(-1) and 1 mg·L~(-1) IBA, which was a potential natural elicitor to induce the accumulation of podophyllotoxin in future production.

Asunto(s)

Ascomicetos , Berberidaceae/química , Raíces de Plantas/crecimiento & desarrollo , Podofilotoxina/biosíntesis , Técnicas de Cultivo de Tejidos , Endófitos , Raíces de Plantas/efectos de los fármacos

RESUMEN

Counter-current chromatography (CCC) is a unique, liquid-liquid partition chromatography process. Both the mobile and stationary phases are liquids, so no solid support matrix is used. CCC has gained wide acceptance as a preparative technique in a variety of fields. Because the mobile and stationary phases are both liquids, gradient elution is difficult to perform with CCC. Phase equilibrium must be maintained, so any change in the composition of one phase may induce a compositional change in the other. In this work, a new linear gradient elution method was developed for CCC. Biphasic solvent systems containing heptane, ethyl acetate, methanol, and water (HepEMWat) in various ratios were prepared and used to optimize both isocratic and linear gradient CCC separation with methanol. We first separated a test mixture of four standard compounds with partition coefficients ranging from 0.8 to 7.8. The separation resembled a reversed-phase process, and elution was performed while progressively decreasing the polarity of the mobile phase. Target molecules with small partition coefficients eluted first in the lower phase of the optimized HepEMWat solvent system. Elution of constituents with large partition coefficients was quite slow under isocratic conditions. Separation time was significantly reduced when elution was performed with a linear gradient using methanol and the optimal HepEMWat system. Elution with a 3:7:4:6 (v/v/v/v) HepEMWat system took approximately 200 min. This included an 80-min isocratic step, followed by gradient elution with methanol from 0% to 30%. The optimized methanol linear gradient CCC method was then used to separate a complex mixture of natural products isolated from Sinopodophyllum hexandrum (Royle) Ying roots. Twelve compounds with a wide range of polarities were well-resolved in a single separation. We have developed a convenient and cost-effective strategy for the separation of complex mixtures. No tedious mobile phase preparation step is required. The volume of unused mobile phase is minimal, so little solvent is wasted. The method is an important advance for the separation of mixtures that contain many compounds with a large range of polarities and partition coefficients, which are common features of natural products.

Asunto(s)

Berberidaceae/química , Productos Biológicos/aislamiento & purificación , Distribución en Contracorriente/métodos , Metanol/química , Cromatografía Líquida de Alta Presión/métodos , Extractos Vegetales/aislamiento & purificación , Solventes/química , Agua/química

RESUMEN

8,2'-Diprenylquercetin 3-methyl ether, a natural product with prominent anti-breast cancer activity, is the main active constituent of Sinopodophylli Fructus. A high-performance liquid chromatography with a diode array detector coupled with electrospray ionization ion trap time-of-flight multistage mass spectrometry (HPLC-DAD-ESI-IT-TOF-MSn) method was established and applied to profile and identify the metabolites of 8,2'-diprenylquercetin 3-methyl ether as well as study their distribution in rat organs for the first time. A total of 100 new metabolites were tentatively identified in rats. The metabolic reactions of 8,2'-diprenylquercetin 3-methyl ether in rats in vivo were hydroxylation, methylation, glucuronidation, dehydrogenation, sulfation, polymerization and cysteine conjugation as well as the specific reactions of leucine/isoleucine, proline, and vitamin C conjugation. The detected metabolites included 77 in faeces, 50 in urine, 11 in plasma, 50 in the small intestine, 32 in the stomach, 23 in the liver, 9 in the lungs, 9 in the spleen, 8 in the heart, and 6 in the kidneys. The results indicated that the small intestine, stomach, and liver were the major organs for the distribution of 8,2'-diprenylquercetin 3-methyl ether metabolites. Furthermore, 27 metabolites showed various bioactivities predicted by the analysis of "PharmMapper", among which 9 metabolites showed anti-cancer activity. These results are very useful for understanding the metabolism and pharmacological actions as well as the effective forms and toxic actions of 8,2'-diprenylquercetin 3-methyl ether in vivo; moreover, they will lay the foundation for further studies on the metabolism of prenylflavonoid compounds.

Asunto(s)

Quercetina/análogos & derivados , Animales , Berberidaceae/química , Cromatografía Líquida de Alta Presión , Frutas/química , Masculino , Estructura Molecular , Quercetina/metabolismo , Ratas , Ratas Sprague-Dawley , Espectrometría de Masa por Ionización de Electrospray , Distribución Tisular

RESUMEN

Synthesis of biogenic metal nanoparticles using plant extract has gained considerable attention in recent years. The present study aims to synthesize and investigate the cytotoxic effect of silver nanoparticles (AgNPs) from Dysosma pleiantha rhizome extract. The green biosynthesis of AgNPs was verified by ultraviolet visible spectrometer, and characterized using fourier transform infrared spectroscopy, transmission electron microscopy and scanning electron microscopy. Results of microscopic studies revealed that the synthesized AgNPs were a spherical shape with an average size of 76 nm. We also examined the anti-cancer activity of biologically synthesized AgNPs. The dose-dependent cytotoxicity was observed in the breast cancer cell lines MDA-MB-231 and MDA-MB-453 treated with biogenically synthesized AgNPs, and the IC50 was recorded at 33.521  and 36.25 µM respectively. The DNA fragmentation analysis showed that the MDA-MB-231 cells treated with increasing concentrations of AgNPs significantly triggered the fragmentation of DNA. In addition, the synthesized AgNPs exhibited dose dependent cytotoxic potential against human gastric cancer cell lines and the IC50 was recorded at 7.14 µM. Thus, the green biosynthesized AgNPs from D. pleiantha rhizome can be used in the novel development of anticancer drugs.

Asunto(s)

Antineoplásicos Fitogénicos/síntesis química , Antineoplásicos Fitogénicos/farmacología , Berberidaceae/química , Nanopartículas del Metal , Extractos Vegetales/farmacología , Rizoma/química , Plata , Antineoplásicos Fitogénicos/química , Supervivencia Celular/efectos de los fármacos , Humanos , Nanopartículas del Metal/química , Extractos Vegetales/química , Plata/química , Análisis Espectral

RESUMEN

Nandina domestica (Berberidaceae) has been used in traditional medicine for the treatment of cough. This plant is distributed in Korea, Japan, China, and India This study aimed to investigate the anti-inflammatory phytochemicals obtained from the N. domestica fruits. We isolated a biflavonoid-type phytochemical, robustaflavone (R), from N. domestica fruits through bioactivity-guided fractionation based on its capacity to inhibit inflammation. The anti-inflammatory mechanism of R isolated from N. domestica has not yet been studied. In the present study, we evaluated the anti-inflammatory activities of R using lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. We have shown that R reduces the production of nitric oxide (NO), pro-inflammatory cytokine interleukin-1 beta (IL-1ß), and IL-6. Western blot analysis showed that R suppresses the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), and downregulates the expression of LPS-induced nuclear factor-kappa B (NF-κB) and the phosphorylation of extracellular-regulated kinases (pERK 1/2). Moreover, R inhibited IL-8 release in LPS-induced human colonic epithelial cells (HT-29). These results suggest that R could be a potential therapeutic candidate for inflammatory bowel disease (IBD).

Asunto(s)

Berberidaceae/química , Biflavonoides/aislamiento & purificación , Biflavonoides/farmacología , Regulación hacia Abajo , Mediadores de Inflamación/metabolismo , Animales , Biflavonoides/química , Muerte Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Fraccionamiento Químico , Ciclooxigenasa 2/metabolismo , Regulación hacia Abajo/efectos de los fármacos , Enterocitos/efectos de los fármacos , Enterocitos/metabolismo , Quinasas MAP Reguladas por Señal Extracelular/metabolismo , Células HT29 , Humanos , Interleucina-1beta/metabolismo , Interleucina-6/metabolismo , Interleucina-8/biosíntesis , Lipopolisacáridos/farmacología , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Ratones , FN-kappa B/metabolismo , Óxido Nítrico/biosíntesis , Óxido Nítrico Sintasa de Tipo II/metabolismo , Fosforilación/efectos de los fármacos , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Extractos Vegetales/farmacología , Células RAW 264.7

RESUMEN

The tumor suppressor p53 plays essential roles in cellular protection mechanisms against a variety of stress stimuli and its activation induces apoptosis or autophagy in certain cancer cells. Here, we identified protopine, an isoquinoline alkaloid isolated from Nandina domestica, as an activator of the p53 pathway from cell-based natural compound screening based on p53-responsive transcription. Protopine increased the p53-mediated transcriptional activity and promoted p53 phosphorylation at the Ser15 residue, resulting in stabilization of p53 protein. Moreover, protopine up-regulated the expression of p21WAF1/CIP1 and BAX, downstream genes of p53, and inhibited the proliferation of HCT116 colon cancer cells. Apoptosis was elicited by protopine as indicated by caspase-3/7 activation, poly ADP ribose polymerase cleavage, and increased population of Annexin V-FITC-positive cells. Furthermore, protopine induced the formation of microtubule-associated protein 1 light chain 3 (LC3) puncta and LC3-II turnover, typical biochemical markers of autophagy, in HCT116 cells. Our findings suggest that protopine exerts its antiproliferative activity by stimulating the p53 pathway and may have potential as a chemopreventive agent for human colon cancer.

Asunto(s)

Apoptosis/efectos de los fármacos , Autofagia/efectos de los fármacos , Benzofenantridinas/aislamiento & purificación , Benzofenantridinas/uso terapéutico , Alcaloides de Berberina/aislamiento & purificación , Alcaloides de Berberina/uso terapéutico , Neoplasias del Colon/tratamiento farmacológico , Ranunculales/química , Apoptosis/fisiología , Autofagia/fisiología , Benzofenantridinas/farmacología , Berberidaceae/química , Berberidaceae/clasificación , Alcaloides de Berberina/farmacología , Neoplasias del Colon/metabolismo , Neoplasias del Colon/patología , Inhibidor p21 de las Quinasas Dependientes de la Ciclina/metabolismo , Relación Dosis-Respuesta a Droga , Células HCT116 , Humanos , Extractos Vegetales/química , Extractos Vegetales/farmacología , Estabilidad Proteica/efectos de los fármacos , Ranunculales/clasificación , Células Tumorales Cultivadas , Proteína p53 Supresora de Tumor/metabolismo , Regulación hacia Arriba/efectos de los fármacos

RESUMEN

The discovery of few isolated populations of Gymnospermium scipetarum (since now considered as an amphi-Adriatic endemic) in the S-Apennines prompted to investigate, also for conservation purposes, some aspects of its reproductive biology. We aim: (1) to determine if insects play an important role in pollination; (2) to describe the pollinator community; (3) to detect floral scent composition. Experiments of insect exclusion were carried out in the field using 24 flowering individuals: one raceme was capped whereas the nearest one was used as control to ascertain differences in seed set. Pollinator community was detected during the blooming phase of two consecutive flowering seasons by visual observation; insect identification was made at the highest possible taxonomic resolution with the help of digital photographs. In order to determine the chemical composition of the volatiles, we used SPME sampling of cultivated plants. Mann-Whitney U test reveals significant differences for treatment in mean seed set with very low values for capped flowers, thus clearly indicating as insects are crucial for successful pollination. During the 42 h of observations we detected 326 visitors belonging to only three guilds: 79% were Diptera, 20% Hymenoptera and 1% Coleoptera. We identified overall 36 floral organic compounds with only two compounds common to the other studied Berberidaceae. Ambrox was never identified before in the floral scents of any angiosperm. The presence in the scent of several aldehydes and one ketone (benzophenone) could be related to the detected dominance of muscoid flies as pollinators. Floral morphology and composition of the pollinators community indicate a generalist pollination behaviour probably related to its phenology and habitat preference. The possibility of being pollinated also by muscoid flies can be considered an advantage for the reproductive fitness of the species, since these Diptera are abundant in the mountain pastures surrounding the forest habitat of Gymnospermium.

Asunto(s)

Berberidaceae/fisiología , Flores/química , Insectos/fisiología , Polinización , Animales , Berberidaceae/química , Biota , Italia , Odorantes/análisis , Reproducción , Compuestos Orgánicos Volátiles/análisis

RESUMEN

A biflavonoid, amentoflavone isolated from Nandina domestica and characterized by NMR spectral-data analyses was assessed for its antioxidant, and antibacterial potential in vitro and in food-model systems. Amentoflavone exhibited potent antioxidant ability (19.21-75.52%) on scavenging DPPH, ABTS, superoxide, and hydroxyl radicals. Fluorescent images confirmed bacterial membrane depolarization of both the tested pathogens Staphylococcus aureus and Escherichia coli, with a significant reduction in cell viabilities at their respective MIC of 62.5 and 125 µg/mL. Increasing rates of membrane permeability observed in 260 nm-absorbing material, potassium ion, extracellular ATP, and relative electrical conductivity assays confirmed antibacterial mechanistic role of amentoflavone as also evidenced by microscopic studies of SEM and TEM. There was a marked inhibitory effect of amentoflavone with a significant reduction in cell counts of S. aureus and E. coli in minced chicken and apple juice at 4 °C, thus suggesting its nutritional enhancing efficacy as a natural antioxidant and antimicrobial agent.

Asunto(s)

Antibacterianos/farmacología , Berberidaceae/química , Biflavonoides/farmacología , Malus/microbiología , Productos Avícolas/microbiología , Animales , Pollos , Escherichia coli/efectos de los fármacos , Staphylococcus aureus/efectos de los fármacos

RESUMEN

This paper reports the in silico prediction of biological activities of lignans from Diphylleia cymosa and Podophyllum hexandrum combined with an in vitro bioassays. The extracts from the leaves, roots and rhizomes of both species were evaluated for their antibacterial, anticholinesterasic, antioxidant and cytotoxic activities. A group of 27 lignans was selected for biological activities prediction using the Active-IT system with 1987 ligand-based bioactivity models. The in silico approach was properly validated and several ethnopharmacological uses and known biological activities were confirmed, whilst others should be investigated for new drugs with potential clinical use. The extracts from roots of D. cymosa and from rhizomes and roots of P. hexandrum were very effective against Bacillus cereus and Staphylococcus aureus, while podophyllotoxin inhibited the growth of Staphylococcus aureus and Escherichia coli. D. cymosa leaves and roots showed anticholinesterasic and antioxidant activities, respectively. The evaluated extracts showed to be moderately toxic to THP-1 cells. The chromatographic characterization indicated that podophyllotoxin was the major constituent of P. hexandrum extract while kaempferol and its hexoside were the main constituents of D. cymosa leaves and roots, respectively. These results suggest that the podophyllotoxin could be the major antibacterial lignan, while flavonoids could be responsible for the antioxidant activity.

Asunto(s)

Berberidaceae/química , Simulación por Computador , Extractos Vegetales/farmacología , Podophyllum/química , Antibacterianos/farmacología , Antioxidantes/farmacología , Muerte Celular/efectos de los fármacos , Línea Celular , Inhibidores de la Colinesterasa/farmacología , Cromatografía Líquida de Alta Presión , Humanos , Lignanos/química , Lignanos/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Extractos Vegetales/química , Curva ROC , Reproducibilidad de los Resultados , Espectrometría de Masa por Ionización de Electrospray , Espectrometría de Masas en Tándem

RESUMEN

The separation of natural products is grueling and time-consuming work with repeated isolations needed to obtain purified compounds. However, using counter-current chromatography, a unique liquid-liquid partition chromatography, constituents can usually be purified efficiently. During the separation of flavone dimers from Dysosma versipellis (Hance) by counter-current chromatography, the separation resolution and sample loading was impeded by the emulsification of the sample. By screening, trifluoroacetic acid was selected as the solvent modifier to eliminate the emulsification. Then, a quaternary solvent system of hexane/ethyl acetate/methanol/water (4:6:5:5 v/v/v/v) with trifluoroacetic acid at a low concentration of 0.5% v/v was used to purify the components from D. versipellis. Compared to that without trifluoroacetic acid, the separation resolution as well as the sample loading both increased greatly. In addition, flavone dimers in low concentrations could be enriched and purified at high sample loading. As a result, five podophyllotoxins and 11 flavonoids were purified and characterized by interpretation of spectroscopic data, in which two of eight flavone dimers were new and a known flavone dimer was first separated from this species.

Asunto(s)

Berberidaceae/química , Productos Biológicos/aislamiento & purificación , Flavonas/aislamiento & purificación , Ácido Trifluoroacético/química , Productos Biológicos/química , Cromatografía Líquida de Alta Presión , Distribución en Contracorriente , Dimerización , Flavonas/química