RESUMO
INTRODUCTION: Scrophulariae Radix (SR) has been extensively used in traditional Chinese medicine (TCM) for thousands of years. However, the processing methods and production areas of Scrophularia ningpoensis have undergone notable historic changes. Thus, their effects on the bioactive constituents of SR still need to be studied further. OBJECTIVES: This study aimed to establish an objective and comprehensive method to identify the correlation of bioactive constituents of SR with variety, place of origin and processing method for evaluating their qualities. METHODOLOGY: An accurate and rapid high-performance liquid chromatography-diode array detector (HPLC-DAD) method for the simultaneous determination of 11 marker components (aucubin, harpagide, 6-O-methyl-catalpol, harpagoside, verbascoside, isoverbascoside, angoroside C, cinnamic acid, l-tyrosine, l-phenylalanine, and l-tryptophan) was established to evaluate the quality of SR for the first time. In addition, the effects of different production areas and processed methods on the target compounds were studied by analysing 66 batches of SR samples with chemometrics methods, including similarity evaluation of chromatographic fingerprints of TCM, principal component analysis (PCA), and partial least squares-discriminant analysis (PLS-DA). RESULTS: Compared with "sweating", short-term "steaming" and "slice-drying" could largely preserve the bioactive constituents of SR. When using the model established through PLS-DA, five components were identified as the most significant variables for discrimination. Furthermore, the score plots of PCA and the similarity evaluation revealed that variety had a more notable influence on the quality of SR than the place of origin. CONCLUSION: An objective approach of HPLC fingerprint coupled with chemometrics analysis and quantitative assessment could be applied to discriminate different processed SR and evaluate the qualities of SR rapidly.
Assuntos
Medicamentos de Ervas Chinesas , Scrophularia , Cromatografia Líquida de Alta Pressão/métodos , Quimiometria , Medicamentos de Ervas Chinesas/química , Scrophularia/química , ChinaRESUMO
Two new lignans (1-2) and a new octaketide (12), together with twenty-nine known compounds (3-11, 13-32) were isolated and identified from the aerial part of Pogostemon cablin. Their chemical structures were revealed mainly through NMR and MS data. The absolute configuration of 1 and 2 was deduced by comparing its experimental CD with the calculated ECD spectra. The inhibitory activities of the isolated compounds on LPS-stimulated nitric oxide (NO) production in RAW 264.7 cells were investigated. At a concentration of 25â µM, compounds 1 and 11 showed approximately equal NO inhibitory effects to that of aminoguanidine.
Assuntos
Lignanas , Pogostemon , Camundongos , Animais , Lignanas/química , Pogostemon/química , Glicosídeos/química , Células RAW 264.7 , Componentes Aéreos da Planta/química , Estrutura Molecular , Óxido NítricoRESUMO
Scrophulariae Radix (SR) is one of the oldest and most frequently used Chinese herbs for oriental medicine in China. Before clinical use, the SR should be processed using different methods after harvest, such as steaming, "sweating", and traditional fire-drying. In order to investigate the difference in chemical constituents using different processing methods, the two-dimensional (2D) 1H-13C heteronuclear single quantum correlation (1H-13C HSQC)-based metabolomics approach was applied to extensively characterize the difference in the chemical components in the extracts of SR processed using different processing methods. In total, 20 compounds were identified as potential chemical markers that changed significantly with different steaming durations. Seven compounds can be used as potential chemical markers to differentiate processing by sweating, hot-air drying, and steaming for 4 h. These findings could elucidate the change of chemical constituents of the processed SR and provide a guide for the processing. In addition, our protocol may represent a general approach to characterizing chemical compounds of traditional Chinese medicine (TCM) and therefore might be considered as a promising approach to exploring the scientific basis of traditional processing of TCM.
Assuntos
Medicamentos de Ervas Chinesas , Cromatografia Líquida de Alta Pressão/métodos , Medicamentos de Ervas Chinesas/química , Medicina Tradicional Chinesa , Metabolômica/métodos , Raízes de Plantas/químicaRESUMO
Linariifolioside II (1) and (2S)-2-hydroxy-5-oxoproline methyl ester (2), two new compounds along with 13 known compounds were obtained from the aerial part of Pseudolysimachion linariifolium Holub subsp. dilatatum (Nakai & Kitag.) D.Y. Hong. Their chemical structures were revealed mainly through NMR and MS data. The absolute configuration of 2 was deduced by comparing its experimental CD with the calculated ECD spectra. At a concentration of 1â mm, total antioxidant capacities of compounds 1-15 were measured using a rapid ABTS method inâ vitro. Compounds 1, 3-5, and 11-14 exhibited approximately equal antioxidant capacity to that of vitamin C (Vc).
Assuntos
Antioxidantes/farmacologia , Medicamentos de Ervas Chinesas/farmacologia , Lactamas/farmacologia , Fenóis/farmacologia , Extratos Vegetais/farmacologia , Veronica/química , Antioxidantes/química , Antioxidantes/isolamento & purificação , Benzotiazóis/antagonistas & inibidores , Relação Dose-Resposta a Droga , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Lactamas/química , Lactamas/isolamento & purificação , Medicina Tradicional Chinesa , Estrutura Molecular , Fenóis/química , Fenóis/isolamento & purificação , Componentes Aéreos da Planta/química , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Ácidos Sulfônicos/antagonistas & inibidoresRESUMO
Bavachinin (BVC), one of the main bioactive prenylated flavonoids derived from Psoralea corylifolia Linn, has a wide variety of pharmacological effects, such as antiangiogenic, antitumor, antiallergic, anti-inflammatory and antibacterial activities, especially as a pan-peroxisome proliferator-activated receptors agonist. A rapid and sensitive method for quantifying BVC in rat plasma was developed and validated through ultra-high-performance liquid chromatography coupled with electrospray-ionization tandem mass spectrometry. Furthermore, a complete metabolic investigation of BVC was performed through ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. In the pharmacokinetic analysis, BVC exhibited rapid oral absorption (Tmax = 0.68 ± 0.21 h), good elimination (T1/2 = 2.27 ± 1.63 h) following oral administration and poor absolute bioavailability (5.27%). Moreover, 11 metabolites of BVC in plasma, urine, bile and feces were characterized. The main metabolic pathways of BVC involved isomeriszation, glucuronidation, sulfonation, hydroxylation, methoxylation and reduction. In conclusion, the present study provides a sensitive quantitative method with a lower limit of quantification of 1 ng/mL and an improved comprehension of the physiological disposition of BVC.
Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Flavonoides/análise , Flavonoides/farmacocinética , Espectrometria de Massas por Ionização por Electrospray/métodos , Animais , Flavonoides/química , Flavonoides/metabolismo , Modelos Lineares , Masculino , Modelos Moleculares , Ratos , Ratos Sprague-Dawley , Reprodutibilidade dos Testes , Sensibilidade e Especificidade , Espectrometria de Massas em Tandem/métodosRESUMO
Eutypenoids A-C (1-3), pimarane diterpenoid alkaloid and two ring A rearranged pimarane diterpenoids, were isolated from the culture of Eutypella sp. D-1 obtained from high-latitude soil of the Arctic. Their structures, including absolute configurations, were authenticated on the basis of the mass spectroscopy (MS), nuclear magnetic resonance (NMR), X-ray crystallography, and electronic circular dichroism (ECD) analysis. The immunosuppressive effects of eutypenoids A-C (1-3) were studied using a ConA-induced splenocyte proliferation model, which suggested that 2 exhibited potent immunosuppressive activities.
Assuntos
Abietanos/isolamento & purificação , Ascomicetos/química , Imunossupressores/isolamento & purificação , Abietanos/química , Abietanos/farmacologia , Animais , Regiões Árticas , Proliferação de Células/efeitos dos fármacos , Dicroísmo Circular , Concanavalina A/farmacologia , Cristalografia por Raios X , Imunossupressores/química , Imunossupressores/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Camundongos , Camundongos Endogâmicos BALB C , Microbiologia do Solo , Baço/citologia , Baço/efeitos dos fármacosRESUMO
CONTEXT: Sea cucumbers have been consumed as tonic, food, and nutrition supplements for many years. OBJECTIVE: The objective of this study is to investigate the antiobesity and lipid-lowering effects of sea cucumber extracts in in vitro and in vivo models and elucidate the mechanism of action of the extracts on obesity and dyslipidemia. MATERIALS AND METHODS: The 60% ethanol extracts from the body walls of 10 different sea cucumbers were investigated for the inhibition of pancreatic lipase (PL) activity in vitro. The optimal active extract (SC-3) was further chemically analyzed by LC-MS and UV. And 0.1% and 0.2% of SC-3 was mixed with a high-fat diet to treat C57/BL6 mice for 6 weeks or 2 weeks as preventive and therapeutic study. The body weight, serum, and liver lipid profile in the mice were investigated. RESULTS: The crude extract of Pearsonothuria graeffei Semper (Holothuriidae) inhibited the PL activity by 36.44% of control at 0.5 µg/mL. SC-3 and echinoside A inhibited PL with an IC50 value at 2.86 µg/mL and 0.76 µM. 0.1% of SC-3 reduced the body weight (23.0 ± 0.62 versus 26.3 ± 0.76 g), the serum TC (2.46 ± 0.04 versus 2.83 ± 0.12 mmol/L), TG (0.19 ± 0.08 versus 0.40 ± 0.03 mmo/L), and LDL-c (0.48 ± 0.02 versus 0.51 ± 0.02 mmol/L), and liver TC (1.19 ± 0.17 versus 1.85 ± 0.13 mmol/mg) and TG (6.18 ± 0.92 versus 10.87 ± 0.97 mmol/mg) contents of the obese C57BL/six mice on a high-fat diet. DISCUSSION AND CONCLUSION: Sea cucumber may be used for developing antiobesity and antihyperlipidemia drugs.
Assuntos
Fármacos Antiobesidade/farmacologia , Inibidores Enzimáticos/farmacologia , Lipase/antagonistas & inibidores , Receptores X do Fígado/efeitos dos fármacos , Fígado/efeitos dos fármacos , Obesidade/prevenção & controle , Pâncreas/enzimologia , Saponinas/farmacologia , Pepinos-do-Mar/metabolismo , Transdução de Sinais/efeitos dos fármacos , Adipócitos Brancos/efeitos dos fármacos , Adipócitos Brancos/metabolismo , Animais , Fármacos Antiobesidade/isolamento & purificação , Dieta Hiperlipídica , Modelos Animais de Doenças , Relação Dose-Resposta a Droga , Inibidores Enzimáticos/isolamento & purificação , Feminino , Células Hep G2 , Holoturina/análogos & derivados , Holoturina/farmacologia , Humanos , Absorção Intestinal/efeitos dos fármacos , Lipase/metabolismo , Lipídeos/sangue , Fígado/metabolismo , Receptores X do Fígado/metabolismo , Camundongos Endogâmicos C57BL , Obesidade/sangue , Obesidade/etiologia , Saponinas/isolamento & purificação , Fatores de Tempo , Regulação para Cima , Aumento de Peso/efeitos dos fármacosRESUMO
The single-electrode readout method has been applied to a coplanar grid (CPG) array CdZnTe detector in order to halve the number of preamplifiers previously needed and to facilitate imaging applications of CPG detectors. A method of predetermining the width of the optimum collecting electrodes has also been proposed, using the calculated optimum relative gain factor G. Meanwhile, a detailed process for calculating the charge induction efficiency (CIE) is presented. To simplify the calculation process, the computational formula of the CIE was deduced through the integration of the weighting potential. For performance evaluation, a 2 × 2 CPG-array CdZnTe detector was elaborately designed and tested with (137)Cs at 662 keV. Experimental results showed the capability of using the CPG-array CdZnTe detector with single collecting electrode readout for γ-ray imaging applications, with the same complexity of associated readout electronics as that of the pixelated CdZnTe detectors.
RESUMO
We have previously shown that scropolioside B has higher anti-inflammatory activity than catalpol does after the inhibition of nuclear factor (NF)-κB activity and IL-1ß expression, maturation, and secretion. Various scropoliosides were extracted, isolated, and purified from Scrophularia dentata Royle ex Benth. We then compared their anti-inflammatory activities against LPS-induced NF-κB activity, cytokines mRNA expression, IL-1ß secretion, and cyclooxygenase-2 activity. The inhibitory effects of the scropoliosides varied depending on whether the 6-O-substituted cinnamyl moiety was linked to C'' 2-OH, C''3-OH, or C''4-OH, and on the number of moieties linked, which is closely related to the enhancement of antiinflammatory activity. Among these compounds, scropolioside B had the strongest antiinflammatory effects.
Assuntos
Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Glucosídeos Iridoides/química , Glucosídeos Iridoides/farmacologia , Ácido Araquidônico/metabolismo , Citocinas/genética , Citocinas/metabolismo , Ativação Enzimática/efeitos dos fármacos , Expressão Gênica , Células HEK293 , Humanos , NF-kappa B/metabolismo , Ressonância Magnética Nuclear Biomolecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Relação Estrutura-AtividadeRESUMO
Chronic inflammation is associated with various chronic illnesses including immunity disorders, cancer, neurodegeneration, and vascular diseases. Iridoids are compounds with anti-inflammatory properties. However their anti-inflammatory mechanism remains unclear. Here, we report that scropolioside B, isolated from a Tibetan medicine (Scrophularia dentata Royle ex Benth.), blocked expressions of TNF, IL-1, and IL-32 through NF-κB pathway. Scropolioside B inhibited NF-κB activity in a dose-dependent manner with IC50 values of 1.02 µmol/L. However, catalpol, similar to scropolioside B, was not effective in inhibiting NF-κB activity. Interestingly, scropolioside B and catalpol decreased the expression of NLRP3 and cardiolipin synthetase at both the mRNA and protein level. Our results showed that scropolioside B is superior in inhibiting the expression, maturation, and secretion of IL-1ß compared to catalpol. These observations provide further understanding of the anti-inflammatory effects of iridoids and highlight scropolioside B as a potential drug for the treatment of rheumatoid arthritis and atherosclerosis.
Assuntos
Anti-Inflamatórios/farmacologia , Citocinas/antagonistas & inibidores , Inflamassomos/efeitos dos fármacos , Interleucina-1beta/antagonistas & inibidores , Glucosídeos Iridoides/farmacologia , Anti-Inflamatórios/isolamento & purificação , Proteínas de Transporte/genética , Proteínas de Transporte/metabolismo , Expressão Gênica/efeitos dos fármacos , Células HEK293 , Humanos , Inflamassomos/imunologia , Inflamassomos/metabolismo , Glucosídeos Iridoides/isolamento & purificação , Medicina Tradicional Chinesa , Proteínas de Membrana/genética , Monócitos/efeitos dos fármacos , Monócitos/imunologia , Monócitos/metabolismo , NF-kappa B/metabolismo , Proteína 3 que Contém Domínio de Pirina da Família NLR , Scrophularia/química , Transdução de Sinais/efeitos dos fármacosRESUMO
Phytochemical investigation of the roots of Scrophularia buergeriana Miq. (Scrophulariaceae), resulted in the isolation of a new iridoid derivative named as buergerinin (1). Its structure was elucidated as rel-(1R, 5R, 6R)-(2-oxa-bicyclo[3.3.0]oct-7-en-6, 7-diyl)dimethoxypropane based mainly on MS and 1D and 2D NMR spectroscopic analyses.
Assuntos
Iridoides/química , Raízes de Plantas/química , Scrophularia/química , Iridoides/isolamento & purificação , Espectroscopia de Ressonância Magnética , Espectrometria de MassasRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: The dried aerial parts of Veronica linariifolia subsp. dilatata (Nakai & Kitag.) D.Y.Hong named Shui Man Jing (SMJ) is a traditional Chinese medicine with a long history of clinical use in the treatment of chronic bronchitis and coughing up blood, however, its role on acute lung injury (ALI) has not been revealed yet. AIM OF THE STUDY: To assess the efficiency of SMJ on ALI and to investigate whether it inhibited endothelial barrier dysfunction by regulating the EGFR/Akt/ZO-1 pathway to alleviate ALI in vivo and in vitro based on the result of network pharmacology. MATERIALS AND METHODS: An in vivo model of ALI was established using inhalation of atomized lipopolysaccharide (LPS), and the effects of SMJ on ALI were evaluated through histopathological examination and inflammatory cytokines, lung histology and edema, vascular and alveolar barrier disruption. Network pharmacology was applied to predict the mechanism of SMJ in the treatment of ALI. The crucial targets were validated by RT-PCR, Western Blotting, molecular docking, immunohistochemistry and immunofluorescence methods in vivo and in virto. RESULTS: Administration of SMJ protected mice against LPS-induced ALI, including ameliorating the histological alterations in the lung tissues, and decreasing lung edema, protein content of bronchoalveolar lavage fluid, infiltration of inflammatory cell and secretion of cytokines. SMJ exerted protective effects in ALI by inhibiting endothelial barrier dysfunction in mice and bEnd.3 cell. SMJ relieved endothelial barrier dysfunction induced by LPS through upregulating the EGFR expression. SMJ also increased the phosphorylation of Akt, and ZO-1 expression both in vivo and in vitro. CONCLUSION: SMJ attenuates vascular endothelial barrier dysfunction for LPS-induced ALI via EGFR/Akt/ZO-1 pathway, and is a promising novel therapeutic candidate for ALI.
Assuntos
Lesão Pulmonar Aguda , Lipopolissacarídeos , Humanos , Masculino , Camundongos , Animais , Lipopolissacarídeos/metabolismo , Proteínas Proto-Oncogênicas c-akt/metabolismo , Simulação de Acoplamento Molecular , Lesão Pulmonar Aguda/induzido quimicamente , Lesão Pulmonar Aguda/tratamento farmacológico , Lesão Pulmonar Aguda/metabolismo , Pulmão , Células Endoteliais , Citocinas/metabolismo , Edema/metabolismo , Receptores ErbB/metabolismoRESUMO
Atopic dermatitis is a chronic relapsing skin disease characterized by recurrent, pruritic, localized eczema, while PDE4 inhibitors have been reported to be effective as antiatopic dermatitis agents. 3',4-O-dimethylcedrusin (DCN) is a natural dihydrobenzofuran neolignan isolated from Magnolia biondii with moderate potency against PDE4 (IC50 = 3.26 ± 0.28 µM) and a binding mode similar to that of apremilast, an approved PDE4 inhibitor for the treatment of psoriasis. The structure-based optimization of DCN led to the identification of 7b-1 that showed high inhibitory potency on PDE4 (IC50 = 0.17 ± 0.02 µM), good anti-TNF-α activity (EC50 = 0.19 ± 0.10 µM), remarkable selectivity profile, and good skin permeability. The topical treatment of 7b-1 resulted in the significant benefits of pharmacological intervention in a DNCB-induced atopic dermatitis-like mice model, demonstrating its potential for the development of novel antiatopic dermatitis agents.
Assuntos
Dermatite Atópica , Lignanas , Inibidores da Fosfodiesterase 4 , Camundongos , Animais , Dermatite Atópica/induzido quimicamente , Dermatite Atópica/tratamento farmacológico , Inibidores da Fosfodiesterase 4/farmacologia , Inibidores da Fosfodiesterase 4/uso terapêutico , Dinitroclorobenzeno/farmacologia , Dinitroclorobenzeno/uso terapêutico , Lignanas/farmacologia , Lignanas/uso terapêutico , Inibidores do Fator de Necrose Tumoral/farmacologia , Inibidores do Fator de Necrose Tumoral/uso terapêutico , Citocinas/farmacologia , PeleRESUMO
Blueberry leaves (BBL) are a natural source with strong antioxidant activity, but bioactive compounds and their seasonal variation remain vague. Here, two major classes of compounds including four caffeoylquinic acids and eight flavonoids were identified in two southern highbush cultivars ("Lanmei" #1 and "Jewel") grown in China. Major bioactive compounds were discovered using an online HPLC post-column derivatization system and determined as neochlorogenic acid (NeoCA), chlorogenic acid (CA), rutin, hyperoside, and isoquercitrin. CA contributed the most to the BBL antioxidant activity. "Lanmei" showed significant advantages in terms of rutin content and antioxidant activity over "Jewel" (P < 0.05). The highest CA content (CAC) of juvenile "Jewel" leaves reached 17.9%. July was the optimum harvest time for both cultivars after fruiting stage. Total phenolic content (TPC) and Trolox equivalent antioxidant capacity (TEAC) of fresh BBL were accurately predicted by a portable near-infrared (NIR) device in a rapid, low-cost, and non-destructive way in situ.
Assuntos
Antioxidantes , Mirtilos Azuis (Planta) , Folhas de Planta , Estações do Ano , Espectroscopia de Luz Próxima ao Infravermelho , Folhas de Planta/química , Mirtilos Azuis (Planta)/química , Antioxidantes/química , Antioxidantes/análise , China , Espectroscopia de Luz Próxima ao Infravermelho/métodos , Extratos Vegetais/química , Flavonoides/análise , Flavonoides/químicaRESUMO
Six new iridoid derivatives (1-6)ï¼together with twelve known compounds (7-18), were isolated and identified from the dried fruits of Catalpa ovata G. Don. Their chemical structures were mainly established through the relative spectroscopic data, while the absolute configurations of compounds 2 and 3 were elucidated on the electronic circular dichroism calculations. Their antioxidant activities were evaluated by activating the Nrf2 transcriptional pathway in 293 T cells in vitro. Among them, Compounds 1, 3, 4, 6-8, 10-12, 14, 15, 17 and 18 showed significant Nrf2 agonistic effect compared with the control group at 25 µM. Finally, The hypothetical biosynthetic pathway for 1-13 was discussed.
Assuntos
Antioxidantes , Bignoniaceae , Antioxidantes/farmacologia , Antioxidantes/química , Estrutura Molecular , Iridoides/farmacologia , Iridoides/química , Fator 2 Relacionado a NF-E2 , Dicroísmo Circular , Bignoniaceae/químicaRESUMO
Thirteen undescribed ursane-type triterpenoids, named as sangosides A-M (1-13), including two nor-ursanes, one split ring-ursane and ten ursanes, along with thirty-six known triterpenoids (14-49) were isolated and identified from the roots of Sanguisorba officinalis (Rosaceae). Their structures and absolute configurations were elucidated through spectroscopic data, single-crystal X-ray crystallography and electronic circular dichroism analysis. Their Nrf2 activation activity was evaluated in 293 T cells in vitro. Compounds 2, 5-7, 9-13, 19, 25, 26, 28-39, 41 and 46 showed significant Nrf2 agonistic effects compared with the control group at 25 µM, their cytotoxicity and dose-effect relationship were further studied in a dose-dependent manner. Their structure-activity relationships analysis suggested that the pentacyclic triterpenoids (10, 11, 30-34 and 41) contains two pairs of double bonds on the C & E rings and the ursane-type triterpenoids (25 and 26) with a carbonyl to C-2 and a hydroxyl group at C-3 all showed a considerably Nrf2 activation activity. These results suggested that S. officinalis was worthy of further investigation to find small molecule Nrf2 activators and facilitate their utilization as natural antioxidants.
Assuntos
Sanguisorba , Triterpenos , Triterpenos/química , Sanguisorba/química , Estrutura Molecular , Fator 2 Relacionado a NF-E2RESUMO
The dried flower buds of Magnolia biondii Pamp (herbal name, Xin-Yi) are a traditional Chinese medicine with a long history of clinical use in the treatment of allergic rhinitis and sinusitis. However, the constituents responsible for its antiallergic effects remain clearly unidentified. In the present study, totally 33 lignans were obtained from M. biondii. Among them, two novel furofuran lignans (1 and 2), two novel tetrahydrofuran lignans (3 and 4), and other 16 known lignans were isolated first time from M. biondii. The antiallergic effects of compounds 1-33 on mouse bone marrow-derived mast cells (BMMCs) degrunaliton were evaluated and results showed that compounds 7, 8, 13, 15 and 18 could significantly inhibited ß-hex release on BMMCs. The results proved that furofuran and tetrahydrofuran lignans were the main constituents in M. biondii and their antiallergic effects were related with suppressing mast cell activation.
RESUMO
A new oleanane-type triterpenoid glycoside, 3beta-O-(f-D-xylopyranosyl-(1-->2)-[beta-D-glucopyranosyl (1-->4)-beta-D-glucopyranosyl-(1 -->3)]-beta-D-fucopyranosyl-11, 13(18) diene-olean-23alpha, 28 diol (1), along with three known phenylethyl glycosides (2-4), was isolated from the root of traditional Chinese medicine Scrophularia ningpoensis. Among them, compounds 2 and 3 were obtained from Scrophularia genus for the first time. The structure of compound 1 was elucidated on the basis of spectroscopic method including 1D, 2D NMR and HR-ESI-MS.
Assuntos
Medicamentos de Ervas Chinesas/isolamento & purificação , Glicosídeos/isolamento & purificação , Scrophularia/química , Triterpenos/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Glicosídeos/química , Estrutura Molecular , Raízes de Plantas/química , Plantas Medicinais/química , Triterpenos/químicaRESUMO
Five new sesquiterpenes, namely, guaianes A-E (1-5), including one novel carbon skeleton guaiane-type sesquiterpene derivatives (1), together with thirteen known compounds (6-18), were isolated from the aerial parts of Pogostemon cablin (Blanco.) Benth. Their chemical structures were mainly established through the relative spectroscopic data, while the absolute configurations of compounds 1-5 were elucidated on the base of single-crystal X-ray diffraction analysis and electronic circular dichroism (ECD) calculations. All compounds were tested for their inhibiting effects on NO production in LPS-stimulated BV2 microglia cells as well as the cell viabilities. The results showed that compounds 2-16 and 18 possessed moderately anti-inflammatory activities at a concentration of 50 µM.
Assuntos
Ácido Nítrico/antagonistas & inibidores , Extratos Vegetais/farmacologia , Pogostemon/química , Sesquiterpenos/farmacologia , Cromatografia em Camada Fina , Cristalografia por Raios X , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Ácido Nítrico/metabolismo , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/metabolismo , Polarimetria de Varredura a Laser , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos de Guaiano/química , Sesquiterpenos de Guaiano/isolamento & purificação , Sesquiterpenos de Guaiano/farmacologia , Análise EspectralRESUMO
Harpagide (1) and harpagoside (2) are two iridoid glycosides existing in many medicinal plants. Although they are believed to be the main bioactive compounds related to the anti-inflammatory efficacy of these plants, the mechanisms of their anti-inflammatory activities remain unclear. The results of our present study showed that 1 and 2 had no effects on inhibitions of cyclooxygenase (COX)-1/2 enzyme activity, tumor necrosis factor-α (TNF-α) release, and nitric oxide (NO) production in vitro. However, the hydrolyzed products of 1 and 2 with ß-glucosidase treatment showed a significant inhibitory effect on COX-2 activity at 2.5-100 µM in a concentration-dependent manner. Our further study revealed that the hydrolyzed 2 product was structurally the same as the hydrolyzed 1 product (H-harpagide (3)). The structure of 3 was 2-(formylmethyl)-2,3,5-trihydroxy-5-methylcyclopentane carbaldehyde, with a backbone similar to prostaglandins and COX-2 inhibitors such as celecoxib. All of them have a pentatomic ring with two adjacent side chains. The result of molecular modeling and docking study showed that 3 could bind to the COX-2 active domain well through hydrophobic and hydrogen-bonding interactions, whereas 1 and 2 could not, implying that the hydrolysis of the glycosidic bond of 1 and 2 is a pre-requisite step for their COX-2 inhibitory activity.