RESUMEN
Acute pancreatitis (AP) is an inflammatory disease of the exocrine pancreas. Disruptions in organelle homeostasis, including macroautophagy/autophagy dysfunction and endoplasmic reticulum (ER) stress, have been implicated in human and rodent pancreatitis. Syntaxin 17 (STX17) belongs to the soluble N-ethylmaleimide-sensitive factor attachment protein receptor (SNARE) subfamily. The Qa-SNARE STX17 is an autophagosomal SNARE protein that interacts with SNAP29 (Qbc-SNARE) and the lysosomal SNARE VAMP8 (R-SNARE) to drive autophagosome-lysosome fusion. In this study, we investigated the role of STX17 in the pathogenesis of AP in male mice or rats induced by repeated intraperitoneal injections of cerulein. We showed that cerulein hyperstimulation induced AP in mouse and rat models, which was characterized by increased serum amylase and lipase activities, pancreatic edema, necrotic cell death and the infiltration of inflammatory cells, as well as markedly decreased pancreatic STX17 expression. A similar reduction in STX17 levels was observed in primary and AR42J pancreatic acinar cells treated with CCK (100 nM) in vitro. By analyzing autophagic flux, we found that the decrease in STX17 blocked autophagosome-lysosome fusion and autophagic degradation, as well as the activation of ER stress. Pancreas-specific STX17 knockdown using adenovirus-shSTX17 further exacerbated pancreatic edema, inflammatory cell infiltration and necrotic cell death after cerulein injection. These data demonstrate a critical role of STX17 in maintaining pancreatic homeostasis and provide new evidence that autophagy serves as a protective mechanism against AP.
Asunto(s)
Ceruletida , Pancreatitis , Masculino , Ratones , Animales , Ratas , Humanos , Enfermedad Aguda , Ceruletida/toxicidad , Modelos Animales de Enfermedad , Pancreatitis/inducido químicamente , Autofagia/fisiología , Proteínas SNARE/metabolismo , EdemaRESUMEN
Nine previously undescribed butyrolactone and sesquiterpene derivatives, named cyclopentanone A (1), subamolides F and G (2 and 3), secosubamolide F (4), rupestonic acids J - L (5-7), linderaguaianols A and B (8 and 9), together with six known ones 10-15 were isolated from the roots of Lindera glauca. Their structures, including their absolute configurations were elucidated by extensive spectroscopic analysis, quantum chemical calculations, and Mo2(AcO)4-induced circular dichroism. Compound 1 that possessed a unique five-membered cyclopentane skeleton with a side chain was rarely found from natural sources. The biogenetic pathway for 1-4 was postulated. Secosubamolide F (4) inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW264.7 cells with IC50 value of 1.73 ± 0.18 µM and also significantly suppressed the production of iNOS. The binding interactions between 4 and iNOS were investigated using docking analyses.
Asunto(s)
Inhibidores Enzimáticos/farmacología , Lindera/química , Óxido Nítrico Sintasa de Tipo II/antagonistas & inhibidores , Óxido Nítrico/antagonistas & inhibidores , Raíces de Plantas/química , Sesquiterpenos/farmacología , Animales , Relación Dosis-Respuesta a Droga , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/aislamiento & purificación , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Ratones , Estructura Molecular , Óxido Nítrico/biosíntesis , Óxido Nítrico Sintasa de Tipo II/metabolismo , Células RAW 264.7 , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Relación Estructura-ActividadRESUMEN
The present study is to establish the fingerprints for the quality evaluation of Ilicis Pubescentis Radix by HPLC-UV. The chromatographic conditions were defined as Phenomenex Luna C18(4.6 mm × 250 mm, 5 µm). Mobile phase was acetonitrile-0.05% phosphoric acid in gradient elution, and the flow rate was 0.8 mL·min⻹.Column temperature was 30 °C and the injection volume was 10 µLï¼The detection wavelength was 210 nm. According to the similarity evaluation, the chemometric method was used to assess the quality of Ilicis Pubescentis Radix. The fingerprints of 16 batches of Ilicis Pubescentis Radix were established. There were 29 common peaks in the fingerprints and 12 common peaks were identified by reference substances. Fingerprints similarity of samples were greater than 0.92. The samples were classified into three groups by hierarchical cluster analysis combined with principal component analysis (PCA) and orthogonal partial least squares-discriminant analysis (OPLS-DA), and seven components were the main markers that cause differences in the different batches of samples. By comparing the on-line UV spectra of chromatographic peaks, the chromatographic fingerprint was divided into three regions: region A showed seventeen main peaks (mainly lignans and phenolic acids); region B showed eight main peaks, which were proved as saponins; region C showed four main peaks, which were proved as other components. The established HPLC-UV fingerprint is highly specific, and can be used to evaluate the quality consistency of different batches of Ilicis Pubescentis Radix.
Asunto(s)
Medicamentos Herbarios Chinos/análisis , Ilex/química , Fitoquímicos/análisis , Raíces de Plantas/química , Cromatografía Líquida de Alta Presión , Análisis por Conglomerados , Análisis de Componente Principal , Control de CalidadRESUMEN
Context The roots of Ilex asprella (Hook. et Arn.) Champ. ex Benth. (Aquifoliaceae) are widely used in Chinese medicine to treat influenza, amygdalitis, pertussis, etc. Their mechanism of action is still unknown, which raises the need to identify new bioactive compounds in this plant. Objective In this study, we isolated a novel saponin containing sulphonic groups, namely, asprellcoside A (1) and a known phenolic glycoside compound (2) from the roots of Ilex asprella and evaluated their bioactivities. Materials and methods Molecular structures were elucidated by analysing their spectral and chemical properties. The viability of A549 cells was tested using a MTT assay. Ability of the compounds to inhibit viruses was determined using the neuraminidase activity assay. Their anti-inflammatory effects were tested using the IP-10 activity assay using various concentrations (compound 1: 0.6, 0.2, 0.6, 1.70, 5.00 and 15.00 µM; compound 2: 0.4, 1.2, 3.6, 11.0, 33.0 and 100 µM). Their inhibitory effect on platelet aggregation induced by adenosine diphosphate (ADP) in rabbit plasma was determined at 60 and 80 µM. Results Both compounds inhibit influenza virus strain A/PuertoRico/8/1934 (H1N1) strongly with EC50 values of 4.1 and 1.7 µM, respectively. Both compounds inhibit the secretion of IP-10 with EC50 values of 6.6 and 2.5 µM, respectively. Compound 1 alone inhibited platelet aggregation significantly, with the rate of suppression being 47 ± 8 and 38 ± 3%, at 60 and 80 µM, respectively. Conclusions The results suggest that both compounds may be valid therapeutics against influenza virus infection and that compound 1 may be a novel agent for treating thrombosis.
Asunto(s)
Antiinflamatorios/farmacología , Antivirales/farmacología , Glicósidos/farmacología , Extractos Vegetales/farmacología , Inhibidores de Agregación Plaquetaria/farmacología , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Antivirales/química , Antivirales/aislamiento & purificación , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Citocinas/metabolismo , Perros , Relación Dosis-Respuesta a Droga , Glicósidos/química , Glicósidos/aislamiento & purificación , Humanos , Ilex/química , Mediadores de Inflamación/metabolismo , Subtipo H1N1 del Virus de la Influenza A/efectos de los fármacos , Subtipo H1N1 del Virus de la Influenza A/enzimología , Células de Riñón Canino Madin Darby , Estructura Molecular , Neuraminidasa/antagonistas & inhibidores , Neuraminidasa/metabolismo , Fitoterapia , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Raíces de Plantas , Plantas Medicinales , Agregación Plaquetaria/efectos de los fármacos , Inhibidores de Agregación Plaquetaria/química , Inhibidores de Agregación Plaquetaria/aislamiento & purificación , Conejos , Relación Estructura-ActividadRESUMEN
Phytochemical investigation on the extract of endophytic fungus Tolypocladium sp. SHJJ1 resulted in the identification of a pair of previously undescribed pyridoxatin atropisomers [1 (M/P)] and three new indole diterpenoids (3-5), together with a pair of known pyridoxatin atropisomers [2 (M/P)] and ten known indole diterpenoids (6-15). Their structures, including their absolute configurations were elucidated by extensive spectroscopic analysis, quantum chemical calculations, and X-ray diffraction. Among the undescribed natural products, [1 (M/P)] that two rapidly interconverting atropisomers are the third example to report in the pyridoxatin atropisomers. Except for compounds 1 (M/P) and 2 (M/P), all other compounds were tested for their cytotoxicity using HepG2, A549, and MCF-7 human cell lines. Compound 9 displayed moderate cytotoxicity against the HepG2, A549, and MCF-7 cell lines with IC50 values of 32.39 ± 1.48 µM, 26.06 ± 1.14 µM, and 31.44 ± 1.94 µM, respectively, which was similar to the positive drug cisplatin (with IC50 values of 32.55 ± 1.76 µM, 18.40 ± 1.43 µM, and 27.31 ± 1.22 µM, respectively).
Asunto(s)
Diterpenos , Indoles , Humanos , Diterpenos/farmacología , Diterpenos/aislamiento & purificación , Diterpenos/química , Estructura Molecular , Indoles/aislamiento & purificación , Indoles/farmacología , Indoles/química , Antineoplásicos/farmacología , Antineoplásicos/aislamiento & purificación , Antineoplásicos/química , Endófitos/química , China , Hypocreales/química , Línea Celular Tumoral , Ascomicetos/químicaRESUMEN
Two new 2-(2-phenylethyl)chromones (1-2), two new sesquiterpenes (12-13), and twelve known compounds (3-11, 14-16) were isolated from agarwood of Aquilaria sinensis. These structures were confirmed by HRESIMS, 1D and 2D NMR spectra. The absolute configurations of two new sesquiterpenes were determined by comparing the experimental and calculated ECD spectra. Among them, 7,8-dihydroxy-2-[2-(4'-methoxyphenyl)ethyl]chromone (2) was the first time found that the hydroxyl groups at both C-7/C-8 in agarwood. And Aseudesm B (13), the aldehyded methyl group at C-5 of eucalyptane sesquiterpenes was first discovered in natural products. In the bioassays, all compounds were evaluated for their inhibitory activity against lipopolysaccharide-activated nitric oxide (NO) production in RAW264.7 cells. Compounds 2-5, 7, 9-10, and 13-14 revealed notable inhibitory effects against NO production with IC50 values ranging from 4.0 to 13.0 µM.
Asunto(s)
Sesquiterpenos , Thymelaeaceae , Cromonas/farmacología , Estructura Molecular , Flavonoides/química , Antiinflamatorios/farmacología , Antiinflamatorios/química , Thymelaeaceae/química , Sesquiterpenos/química , Óxido Nítrico , Madera/químicaRESUMEN
Biotransformation of ursane-type triterpenoid ilexgenin A by endophytic fungi Lasiodiplodia sp. MQD-4 and Pestalotiopsis sp. ZZ-1, isolated from Ilex pubescences and Callicarpa kwangtungensis respectively, was investigated for the first time. Six previously undescribed metabolites (1-6) with 23-norursane triterpenoids skeleton were isolated and their structures were unambiguously established by the analysis of spectroscopic data and single-crystal X-ray crystallographic experiments. Decarboxylation, oxidation, and hydroxylation reactions were observed on the triterpenoid skeleton. Especially, the decarboxylation of C-23 provided definite evidence to understand the biogenetic process of 23-norursane triterpenoids. Moreover, the qualitative analysis of the extract of I. pubescences showed metabolites 1, 3, 4, and 6 could be detected in the originated plant, indicating biotransformation by endophytic fungi is a practical strategy for the isolation of novel natural products. Finally, all isolates were evaluated for the protective activities against H2O2-induced HUVECs dysfunction in vitro. Compound 5 could improve the viability of endothelial cells and decrease the level of intracellular ROS.
Asunto(s)
Biotransformación , Endófitos , Células Endoteliales de la Vena Umbilical Humana , Ilex , Triterpenos , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Triterpenos/metabolismo , Endófitos/química , Endófitos/metabolismo , Estructura Molecular , Humanos , Ilex/microbiología , Ascomicetos/química , Ascomicetos/metabolismo , ChinaRESUMEN
The aim of this study is to investigate the protection effect of tanshinone IIA (Tan) against triptolide (TP)-induced liver injury and the mechanisms involved. Acute liver injury was induced by intraperitoneal injection of TP (1 mg x kg(-1)) in mice. The activities of AST, ALT and LDH in serum and the levels of GSH, GST, GSH-PX, SOD, CAT and MDA in liver tissue were detected. The histopathological changes of liver tissues were observed after HE staining. Nrf2 translocation in liver tissue was detected by Western blotting, and real-time PCR was used to measure the expression levels of GCLC, NQO1 and HO-1 mRNA. The results showed that pretreatment with Tan significantly prevented the TP induced liver injury as indicated by reducing the activities of AST, ALT and LDH (P < 0.01). Tan pretreatment also prevented TP-induced oxidative stress in the mice liver by inhibiting MDA and restoring the levels of GSH, GST, SOD and CAT (P < 0.05). Parallel to these changes, pretreatment with Tan could attenuate histopathologic changes induced by TP. Furthermore, the results indicated that Tan pretreatment caused nuclear accumulation of Nrf2 as well as induction of mRNA expression of antioxidant response element (ARE)-driven genes such as GCLC, NQO1 and HO-1. These results indicated that Tan could protect against TP-induced acute liver injury via the activation of Nrf2/ARE pathway.
Asunto(s)
Abietanos/farmacología , Elementos de Respuesta Antioxidante/efectos de los fármacos , Enfermedad Hepática Inducida por Sustancias y Drogas/metabolismo , Factor 2 Relacionado con NF-E2/metabolismo , Animales , Enfermedad Hepática Inducida por Sustancias y Drogas/patología , Diterpenos/toxicidad , Medicamentos Herbarios Chinos/farmacología , Compuestos Epoxi/toxicidad , Glutamato-Cisteína Ligasa/genética , Glutamato-Cisteína Ligasa/metabolismo , Hemo-Oxigenasa 1/genética , Hemo-Oxigenasa 1/metabolismo , Hígado/metabolismo , Hígado/patología , Masculino , Proteínas de la Membrana/genética , Proteínas de la Membrana/metabolismo , Ratones , Ratones Endogámicos C57BL , NAD(P)H Deshidrogenasa (Quinona)/genética , NAD(P)H Deshidrogenasa (Quinona)/metabolismo , Fenantrenos/toxicidad , ARN Mensajero/metabolismo , Transducción de Señal/efectos de los fármacosRESUMEN
Four new chromone compounds diaporspchromanones A-C (1-3) and diaporspchromanone H (4), together with three known compounds (5-7) were separated from the marine derived fungus Diaporthe sp. XW12-1. The structures of the new compounds, including their absolute configurations, were elucidated by extensive spectroscopic analysis and the Mosher's ester method. Among them, diaporspchromanones A-C (1-3) possess a 3-substituted-chroman-4-one skeleton, which are rarely found in natural sources. In the bioassays, all compounds were evaluated for their inhibitory activity against lipopolysaccharide-activated nitric oxide (NO) production in RAW264.7 cells. Compounds 2 and 3 showed potent anti-inflammatory effects than the positive control (indomethacin, IC50, 70.33 ± 0.95 µM) (p < 0.05) with IC50 values of 19.06 ± 3.60 and 9.56 ± 0.18 µM, respectively.
Asunto(s)
Cromonas , Hongos , Animales , Ratones , Cromonas/farmacología , Estructura Molecular , Hongos/química , Células RAW 264.7RESUMEN
Seven previously undescribed meroterpenoids, peniscmeroterpenoids H - N (1-7), were isolated from the marine-derived fungus Penicillium sclerotiorum GZU-XW03-2. Their structures were established by the spectroscopic methods and the electronic circular dichroism (ECD) calculations. Peniscmeroterpenoid H was a 6/6/6/5/6 rearranged pentacyclic meroterpenoid, featuring a unique 2-oxaspiro[5.5] undeca-4,7-dien-3-one motif. Peniscmeroterpenoids I and J (2 and 3) owned rare 6(D)/5(E) fused rings were not common in natural products, and compound 2 was the second example of a berkeleyone analogue stripped of the methyl ester fragment. Peniscmeroterpenoid K (4) was the first case where the C-24 was oxidized. In bioassay, compound 5 showed moderate anti-inflammatory activity.
Asunto(s)
Hongos , Penicillium , Estructura Molecular , Penicillium/química , Dicroismo CircularRESUMEN
A new triterpenoid saponin and fourteen known triterpenoids were isolated from the methanol extract of the stems and leaves of Callicarpa integerrima Champ, which is used in Chinese folk medicine for stopping bleeding, expelling the wind, dissipating stagnation, and treating scrofula, by using various chromatographies, such as silica gel, Sephadex LH-20 and RP-C18 column chromatography. Their structures were identified as a new compound 2alpha, 3beta, 19alpha, 23-tetrahydroxy-olean-12-en-28-oic acid-28-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-glucopyranoside (1), together with fourteen known compounds: oleanolic acid (2), 3-acetyl oleanolic acid (3), 3beta-O-acetyl ursolic acid (4), 2alpha-hydroxy-ursolic acid (5), 2alpha, 3beta, 19alpha, 23-tetrahydroxy-urs-12-en-28-oic acid (6), alpha-amyrin-3-O-beta-D-glucopyranoside (7), pomolic acid (8), betulinic acid (9), ursolic acid (10), 2alpha, 3beta, 19alpha, 23-tetrahydroxy-olean-12-en-28-oic acid (arjungenin) (11), 2alpha-hydroxy-oleanolic acid (12), hederagenin (13), 2alpha, 19alpha-dihydroxy-ursolic acid (14) and pruvuloside A (15), by the spectroscopic techniques of NMR, HMBC, IR and MS, separately. All these compounds were obtained from this plant for the first time, and compounds 3, 4 and 15 were isolated from genus Callicarpa L. for the first time.
Asunto(s)
Callicarpa/química , Ácido Oleanólico/análogos & derivados , Saponinas/aislamiento & purificación , Triterpenos/aislamiento & purificación , Conformación Molecular , Estructura Molecular , Ácido Oleanólico/química , Ácido Oleanólico/aislamiento & purificación , Triterpenos Pentacíclicos , Hojas de la Planta/química , Tallos de la Planta/química , Plantas Medicinales/química , Saponinas/química , Triterpenos/química , Ácido Betulínico , Ácido UrsólicoRESUMEN
Seven undescribed meroterpenoids, peniscmeroterpenoids A - G, were isolated from the marine-derived fungus Penicillium sclerotiorum GZU-XW03-2. Their structures were established by the spectroscopic methods and the electronic circular dichroism (ECD) calculations. Peniscmeroterpenoid A possessed an unprecedented and highly oxidized 6/7/6/5/5 pentacyclic system, featuring a unique tetrahydrofuro [2,3-b]furan-2(3H)-one motif. Peniscmeroterpenoids B - E owned rare 6(D)/5(E) fused rings were not common in natural products, and peniscmeroterpenoid E is the first example of a berkeleyone analogue stripped of the methyl ester fragment. In bioassays, peniscmeroterpenoids A and D inhibited the production of nitric oxide (NO) in RAW264.7 cells with IC50 values of 26.60 ± 1.15 and 8.79 ± 1.22 µM. Moreover, peniscmeroterpenoid D significantly suppressed the production of pro-inflammatory mediators (COX-2, IL-1ß and IL-6) and the protein expression of the enzyme iNOS.
Asunto(s)
Penicillium , Animales , Antiinflamatorios/química , Hongos , Ratones , Estructura Molecular , Penicillium/química , Células RAW 264.7RESUMEN
Four new cytochalasans, arbuschalasins A-D (1-4), along with thirteen known analogues (5-17), were isolated from the solid rice medium of endophytic fungus Xylaria arbuscula. Arbuschalasins A-B feature a rare 5/6/6/6 fused ring system while arbuschalasin D was characterized as the first example of natural cytochalasans that possesses a 5/5/11 fused scaffold. The structures of 1-4 were assigned by spectroscopic data, with their absolute structures being determined by electronic circular dichroism (ECD) calculations. All of the isolates were evaluated against the human colorectal adenocarcinoma cell lines (HCT15). Compounds 6 and 7 showed significant inhibitory effects (IC50 values were 13.5 and 13.4 µM, respectively), being more active than those of the positive control, fluorouracil (103.1 µM).
Asunto(s)
Ascomicetos/química , Citocalasinas/aislamiento & purificación , Rhizophoraceae/microbiología , Línea Celular Tumoral , Supervivencia Celular , Citocalasinas/química , Fermentación , Humanos , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
Eleven undescribed and three known pterocarpans were isolated and identified from the traditional Chinese medicine "Huang-qi", Astragali Radix (the root of Astragalus membranaceus var. mongholicus (Bunge) P.K.Hsiao). The structures of these pterocarpans were determined using spectroscopic, X-ray crystallographic, quantum chemical calculation, and chemical methods. Pterocarpans, almost exclusively distributed in the family of Leguminosae, are the second largest subgroup of isoflavanoids. However, pterocarpan glycoside number is limited, most of which are glucosides, and only one pterocarpan apioside was isolated from nature. Notably, nine rare apiosyl-containing pterocarpan glycosides were isolated and identified. The hypoglycemic activities of all these compounds were evaluated using α-glucosidase and DPP-IV inhibitory assays respectively, and some isolates displayed the α-glucosidase inhibitory function. The antioxidant activities of all compounds were evaluated using the ORAC and DPPH radical scavenging assays, respectively. All compounds exhibited varying degrees of oxygen radical absorbance capacity, and some compounds displayed DPPH radical scavenging ability.
Asunto(s)
Astragalus propinquus , Pterocarpanos , Astragalus propinquus/química , Glicósidos , Medicina Tradicional China , alfa-GlucosidasasRESUMEN
The study is to develop an HPLC method for simultaneous determination of rhamnazin (1), rhamnocitrin (2), rhamnetin (3), rhamnazin-3-O-beta-D-glucopyranoside (4), rhamnazin-3-O-beta-D-xylopyranosyl-(1-->4)-beta-D-glucopyranoside (5), rhamnazin-3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranoside (6), and rhamnocitrin-3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranoside (7) in Nervilia fordii. The separation was performed on a Kromasil C18 column (250 mm x 4.6 mm, 5 microm) with 0.4% phosphoric acid-acetonitrile as the mobile phase in a gradient elution at a flow rate of 1.0 mL x min(-1). The detect wavelength was set at 256 nm, and the column temperature was set at 40 degrees C. There were good linear relationships between the logarithm values of concentrations and those of the peak areas of seven flavonoids (1-7) in the range of 0.55-70.00 microg x mL(-1) (r = 0.9997), 0.86-110.00 microg x mL(-1) (r = 0.9997), 0.39-50.00 microg x mL(-1) (r = 0.999 7), 0.55-70.00 microg x mL(-1) (r = 0.999 5), 1.33-170.00 microg x mL(-1) (r = 0.9998), 1.33-170.00 microg x mL(-1) (r = 0.9998), 0.16-20.00 microg x mL(-1) (r = 0.9995), respectively. The recoveries of the seven flavonoids were between 97.19%-99.45%, the relative standard deviations (RSDs) were between 0.91%-2.69%. The established method is rapid, accurate with high repeatability, which could provide scientific evidence for the quality control of Nervilia fordii.
Asunto(s)
Flavonoides/análisis , Orchidaceae/química , Cromatografía Líquida de Alta Presión , Medicamentos Herbarios Chinos/análisis , Quempferoles/análisis , Hojas de la Planta/química , Plantas Medicinales/química , Control de Calidad , Quercetina/análogos & derivados , Quercetina/análisisRESUMEN
Two new diterpenoids, including a seco-isopimarane type (1) and an abietane type (2), were isolated from Biscogniauxia sp. (71-10-1-1). Their structures, including absolute configurations, were elucidated by NMR spectroscopic analyses, X-ray crystallography, 13C chemical shifts calculations, and ECD calculations. This is the first report of diterpenoids from Biscogniauxia sp. Furthermore, short-term memory enhancement against Alzheimer's disease (AD), anti-inflammatory, and cytotoxic activities of 1-2 were also evaluated. The results showed that compound 1 exhibited short-term memory enhancement activity against AD.
RESUMEN
Two new acetylated flavan glycosides (2S,4R)-4,5,7-trihydroxy-4'-methoxy-6,8-dimethylflavan-5-O-ß-D-6-acetylglucopyranoside-7-O-ß-D-glucopyranoside (1) and (2S,4R)-5,7-dihydroxy-4,4'-dimethoxy-6,8-dimethylflavan-5-O-ß-D-6-acetylglucopyranoside-7-O-ß-D-glucopyranoside (2) were isolated from the rhizomes of Abacopteris penangiana. Their structures were elucidated on the basis of spectroscopic methods including IR, HR-ESI-MS, 1D and 2D NMR, and chemical evidences.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Helechos/química , Flavonoides/aislamiento & purificación , Glucósidos/aislamiento & purificación , Glicósidos/aislamiento & purificación , Acetilación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Flavonoides/química , Flavonoides/farmacología , Glucósidos/química , Glucósidos/farmacología , Glicósidos/química , Glicósidos/farmacología , Células Hep G2 , Humanos , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Rizoma/químicaRESUMEN
OBJECTIVE: To analyze the compositions of the essential oil from the leaves of Callicarpa integerrima. METHODS: GC-MS method was used. RESULTS: 42 chemical constituents, accounting for 97.62% of total content were identified. CONCLUSION: The main components were beta-caryophyllene (33.74%), Elixene (12.86%), tau-Cadinene (9.57%) and (-) -Spathulenol (8.99%). Besides, some sesquiterpenes and their oxides, such as Copaene (4.21%), Globulol (3.81%), alpha-Caryophyllene (2.48%), 2-Naphthalenemethanol, decahydro-alpha, alpha, 4a-trimethyl-8-methylene-[2R-(2alpha, 4aalpha, 8alphabeta)]-(2.37%) and 1,6-Cyclodecadiene (2.24%) had also relatively high contents.
Asunto(s)
Callicarpa/química , Aceites Volátiles/química , Plantas Medicinales/química , Sesquiterpenos/análisis , Cromatografía de Gases y Espectrometría de Masas , Peso Molecular , Sesquiterpenos Monocíclicos , Aceites Volátiles/aislamiento & purificación , Hojas de la Planta/química , Sesquiterpenos PolicíclicosRESUMEN
OBJECTIVE: To study on the chemical constituents of Callicarpa kochiana. METHODS: The chemical constituents were isolated by chromatographic methods and structurally elucidated by spectral analysis. RESULTS: Twelve compounds were obtained and identified as alpha-amyrin(I), 2beta, 3beta, 19alpha-trihydroxy-12-en-28-ursolic acid (II), oleanolic aicd (III), alpha-amyrin-3-0-beta-D-glucopyranoside (IV), ursolic acid (V), betulinic acid (VI), 2alpha, 3beta,23-trihydroxy-12-en-28-oic-0-beta-D-glucopyranoside (VII), 0-hydroxybenzoic acid (VI), pomolic acid (IX), myrianthic acid (X), beta-sitosterol (XI), dauricine (XII). CONCLUSION: All of these compounds are isolated from Callicarpa kochiana for the first time and compounds II, IV, VII, VIII, IX and X are reported for the first time from Callicarpa genus.
Asunto(s)
Callicarpa/química , Plantas Medicinales/química , Triterpenos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura Molecular , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/química , Ácido Oleanólico/aislamiento & purificación , Hojas de la Planta/química , Tallos de la Planta/química , Espectrofotometría Ultravioleta , Triterpenos/química , Ácido UrsólicoRESUMEN
Six previously undescribed cassane diterpenoids, named caesalminaxins O-T (1-6), together with 28 known compounds (7-34), were isolated from the seeds of Caesalpinia minax Hance. Their structures, including their absolute configurations were elucidated by extensive spectroscopic analysis, X-ray diffraction, and quantum chemical calculations. Among the undescribed diterpenoids, compound 6 that possessed an unusual enol group at C-7 with a highly deshielded 1H NMR signal was the first example in cassane diterpenoids. All of the isolates were evaluated for their inhibitory activity against lipopolysaccharide-activated NO production in RAW264.7 cells. Compound 16 showed moderate inhibitory activity with an IC50 value of 17.3⯵M, which was more potent than the positive control (indomethacin, IC50â¯=â¯29.7⯵M).