lignans and ethyl-acetate

Topics: Lignans; Matrix Metalloproteinase 2; Pinus; Plant Extracts; Plant Leaves

Magnoliae Flos is a traditional herbal medicine used to treat nasal congestion associated with headache, empyema, and allergic rhinitis. In our preliminary screening of crude drugs used in Japanese Kampo formulas for melanin synthesis, the methanol extract of Magnoliae Flos was found to exhibit strong melanin synthesis activity. However, there have been no studies evaluating the effects of Magnoliae Flos or its constituents on melanogenesis. The present study aimed to isolate the active compounds from Magnoliae Flos that activate melanin synthesis in melanoma cells and three-dimensional human skin equivalent, and to investigate the molecular mechanism underlying melanin induction. The methanol extract of Magnoliae Flos induced an increase of melanin content in both B16-F1 and HMV-II cells. A comparison of melanin induction by three fractions prepared from the extract showed that the ethyl acetate fraction markedly induced melanin synthesis. Bioassay-guided separation of the ethyl acetate fraction resulted in the isolation of seven lignans (1:  - 7: ). Among them, (+)-magnolin (5: ) strongly induced melanin synthesis and intracellular tyrosinase activity. Furthermore, the ethyl acetate fraction and 5: clearly induced melanin content in a three-dimensional human skin equivalent. Molecular analysis revealed that 5: triggered the protein expression of tyrosinase, tyrosinase-related protein-1, and tyrosinase-related protein-2. Further analysis of transcriptional factors and signaling pathways demonstrated that 5: induces the protein expression of tyrosinase, tyrosinase-related protein-1, and tyrosinase-related protein-2 activated by the protein kinase A- and p38 mitogen-activated protein kinase-dependent pathways, leading to cAMP-responsive element-binding protein phosphorylation and microphthalmia-associated transcription factor expression. These findings demonstrate the potential of 5: as a potent therapeutic agent for hypopigmentation.

Topics: Animals; Cell Line, Tumor; Cyclic AMP-Dependent Protein Kinases; Humans; Lignans; Melanins; Melanoma; Melanoma, Experimental; Methanol; Microphthalmia-Associated Transcription Factor; Monophenol Monooxygenase; p38 Mitogen-Activated Protein Kinases; Signal Transduction

Staphylococcus aureus and Methicillin-resistant S. aureus (MRSA) remains one of the major concerns of healthcare associated and community-onset infections worldwide. The number of cases of treatment failure for infections associated with resistant bacteria is on the rise, due to the decreasing efficacy of current antibiotics. Notably, Acrophialophora levis, a thermophilous fungus species, showed antibacterial activity, namely against S. aureus and clinical MRSA strains. The ethyl acetate extract of culture filtrate was found to display significant activity against S. aureus and MRSA with a minimum inhibitory concentration (MIC) of 1 μg/mL and 4 μg/mL, respectively. Scanning electron micrographs demonstrated drastic changes in the cellular architecture of metabolite treated cells of S. aureus and an MRSA clinical isolate. Cell wall disruption, membrane lysis and probable leakage of cytoplasmic are hallmarks of the antibacterial effect of fungal metabolites against MRSA. The ethyl acetate extract also showed strong antioxidant activity using two different complementary free radicals scavenging methods, DPPH and ABTS with efficiency of 55% and 47% at 1 mg/mL, respectively. The total phenolic and flavonoid content was found to be 50 mg/GAE and 20 mg/CAE, respectively. More than ten metabolites from different classes were identified: phenolic acids, phenylpropanoids, sesquiterpenes, tannins, lignans and flavonoids. In conclusion, the significant antibacterial activity renders this fungal strain as a bioresource for natural compounds an interesting alternative against resistant bacteria.

Topics: Acetates; Anti-Bacterial Agents; Antioxidants; Biological Factors; Flavonoids; Hydroxybenzoates; India; Lignans; Methicillin-Resistant Staphylococcus aureus; Microbial Sensitivity Tests; Microscopy, Electron, Scanning; Sesquiterpenes; Sordariales; Tannins

Application of a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, macroporous adsorbent resin, and reversed-phase HPLC, led to the isolation of 173 compounds including irdidoids, monoterpenes, sesquiterpenes, triterpenes, lignans, flavonoids, and simple aromatic derivatives from the ethyl acetate-soluble fraction of the whole plants of Valeriana jatamansi(Valerianaceae), and their structures were elucidated by spectroscopic methods including 1D, 2D NMR UV, IR, and MS techniques. Among them, 77 compounds were new. In previous reports, we have described the isolation, structure elucidation, and bioactivities of 68 new and 25 known compounds. As a consequence, we herein reported the isolation and structure elucidation of the remaining 9 new and 71 known compounds, the structure revision of valeriotriate A(8a), as well as cytotoxicity of some compounds.

Topics: Acetates; Chromatography, High Pressure Liquid; Flavonoids; Iridoids; Lignans; Molecular Structure; Monoterpenes; Phytochemicals; Plant Extracts; Sesquiterpenes; Triterpenes; Valerian

An efficient method for the rapid extraction, separation and purification of bioactive lignans, arctiin and arctigenin, from Fructus arctii by microwave-assisted extraction coupled with high-speed countercurrent chromatography was developed. The optimal extraction conditions of arctiin and arctigenin were evaluated by orthogonal array. Arctigenin could be converted from arctiin by hydrochloric acid hydrolysis. The separations were performed at a preparative scale with two-phase solvents composed of ethyl acetate-ethanol-water (5 : 1 : 5, v/v/v) for arctiin, and n-hexane-ethyl acetate-ethanol-water (4 : 4 : 3 : 4, v/v/v/v) for arctigenin. From 500 mg of crude extract sample, 122.3 mg of arctiin and 45.7 mg of arctigenin were obtained with the purity of 98.46 and 96.57%, and the recovery of 94.3 and 81.6%, respectively. Their structures were determined by comparison with the high-performance liquid chromatography retention time of standard substance as well as UV, FT-IR, electrospray ion source (ESI)-MS, (1)H-NMR and (13)C-NMR spectrum. According to the antioxidant activity assay, arctigenin had stronger 1,1-diphenyl-2-picrylhydrazyl free radicals scavenging activity.

Topics: Acetates; Arctium; Biphenyl Compounds; Chromatography, High Pressure Liquid; Countercurrent Distribution; Ethanol; Free Radical Scavengers; Furans; Glucosides; Hexanes; Hydrochloric Acid; Hydrolysis; Lignans; Liquid-Liquid Extraction; Microwaves; Picrates; Plant Extracts; Solvents; Water

To study the chemical constituents of Zanthoxyli Cortex.. The chemical constituents were isolated and purified by silica gel and HP-20, MCI gel, Sephadex LH -20 column chromatography, RP-18 and PTLC. Their structures were elucidated by the analysis of spectral data and chemical properties.. Ten compounds were isolated from EtOAc extract and their structures were identified as: asarinin (I), fargesin (II), eudesmin (III), (1R, 2R, 5R, 6S)-2-(3,4-dimethoxyphenyl)-6-(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3.3.0]-octane(IV), dimethoxysamin(V), rel-(1R,5R,6S)-6-(3,4-dimethoxyphen-yl)-3,7-dioxabicyclo-[3.3.0]-octan-2-one(VI), Magnone A(VII), beta-sitoste-rol( VIII), beta-armyrin(IX), beta-amyrone(X).. These compounds isolated from Zanthoxyli Cortex's Ethyl acetate extract are all known compounds. Fargesin(II) and beta-amyrone(X) are isolated from Zanthoxyli Cortex for the first time.

Topics: Acetates; Benzodioxoles; Dioxoles; Furans; Lignans; Magnetic Resonance Spectroscopy; Plant Bark; Plant Extracts; Rutaceae; Triterpenes

Piper regnellii (Miq.) C. DC. var. pallescens (C. DC.) Yunck (Piperaceae) is a medicinal plant traditionally used in Brazil to treat infectious diseases. The extracts obtained of the leaves from P. regnellii were investigated for their antibacterial activities against methicillin-resistant Staphylococcus aureus (MRSA). The ethyl acetate extract presented a good activity against MRSA, with minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) of 16 microg/mL. Based on this finding, the ethyl acetate extract was fractionated by silica gel column chromatography into nine fractions. The hexane fraction was active against MRSA (MIC at 4 microg/mL). Further column chromatography separation of the hexane fraction afforded the pure compound eupomatenoid-5. The structure of the compound was established by spectral data (1H and 13C NMR HSQC, HMBC, gNOE, IR and MS). Eupomatenoid-5 was the only compound active on the bacterium. The antibacterial property of P. regnellii extract provides preliminary scientific validation for the traditional medicinal use of this plant. The active compound eupomatenoid-5 should be further studied in animal models to verify in vivo efficacy and toxicity.

Topics: Acetates; Anti-Bacterial Agents; Benzofurans; Chromatography, Gel; Lignans; Methicillin-Resistant Staphylococcus aureus; Microscopy, Electron, Scanning; Phenols; Piper; Plant Extracts; Plant Leaves; Silica Gel; Silicon Dioxide

Aerial parts of Daphne oleoides Schreber ssp. oleoides (Thymelaeaceae) are used to treat rheumatoid arthritis and lumbago in Turkish folk medicine. In order to evaluate folkloric utilization, in vitro inhibitory effects of the ethyl acetate extract and fractions obtained from this extract on interleukin 1 (IL-1alpha, IL-1beta) and tumour necrosis factor (TNF-alpha) biosynthesis were studied. Through chemical isolation techniques and activity-guided fractionation process, seventeen compounds were isolated and their structures were elucidated (numbered 1-17). Diterpenoids genkwadaphnin (3) and 1,2-dehydrodaphnetoxin (6) and a coumarin derivative daphnetin (9) showed potent inhibitory activity and were found to be the main active ingredients. Furthermore, gnidilatin (4), gnidilatin-20 palmitate (5), genkwadaphnin-20-palmitate (7) and gnidicin-20-palmitate (8), having diterpenoid structure, and eudesmine (12), wikstromol (13) and matairesinol (14), having lignan structure, were determined to possess moderate inhibitory activity and may have a contributory role in the effect of the remedy.

Topics: Acetates; Antineoplastic Agents, Phytogenic; Cytokines; Diterpenes; Dose-Response Relationship, Drug; Enzyme-Linked Immunosorbent Assay; Free Radical Scavengers; Furans; Humans; Interleukin-1; Lignans; Models, Chemical; Plant Extracts; Plants, Medicinal; Tumor Necrosis Factor-alpha; Umbelliferones