benzofurans and loliolide

Skin is the largest organ of humans. Overexposure to ultraviolet (UV) is the primary environmental factor that causes skin damage. The compound, (-)-loliode, isolated from the brown seaweed

Topics: Animals; Apoptosis; Benzofurans; Cell Line; Dermis; Fibroblasts; Humans; Keratinocytes; Reactive Oxygen Species; Sargassum; Seaweed; Sunscreening Agents; Ultraviolet Rays; Zebrafish

Parkinsons Disease (PD) is the second most common neurodegenerative disease worldwide, and is characterized by a progressive degeneration of dopaminergic neurons. Without an effective treatment, it is crucial to find new therapeutic options to fight the neurodegenerative process, which may arise from marine resources. Accordingly, the goal of the present work was to evaluate the ability of the monoterpenoid lactone Loliolide, isolated from the green seaweed

Topics: Animals; Anti-Inflammatory Agents; Benzofurans; Cell Line, Tumor; Chlorophyta; Cytokines; DNA Fragmentation; Humans; Lactones; Macrophages; Membrane Potential, Mitochondrial; Mice; Molecular Structure; Monoterpenes; Neurodegenerative Diseases; Neuroprotective Agents; NF-kappa B; Nitric Oxide; RAW 264.7 Cells; Reactive Oxygen Species

Herein, we reported a novel approach for the preparative separation and purification of loliolide and epiloliolide from Ascophyllum nodosum. An amine-based microporous organic polymer (MOP) was used for the pretreatment of the nodosum extract via solid-phase extraction (SPE). The obtained extract was further purified using macroporous resin chromatography and preparative high-performance liquid chromatography (prep-HPLC). The loading and elution parameters of the MOP were evaluated using standard loliolide, and the optimized conditions were used during the SPE of the nodosum extract (37.5 g). After the pretreatment with MOP, the extract (2.79 g) was obtained and further purified using a D101 resin column followed by prep-HPLC. A pair of epimers were isolated and identified as loliolide (5.83 mg) and epiloliolide (2.50 mg) using high-resolution electrospray ionization tandem mass spectrometry (HRESI-MS), 1D- and 2D-nuclear magnetic resonance (NMR) spectroscopy. This study demonstrates the potential of MOPs in the separation and purification of monoterpenoids from complex plant samples.

Topics: Amines; Ascophyllum; Benzofurans; Chromatography, High Pressure Liquid; Polymers; Solid Phase Extraction

Topics: Animals; Anti-Inflammatory Agents; Aquatic Organisms; Benzofurans; Biological Products; Cell Line; Cell Proliferation; Humans; NLR Family, Pyrin Domain-Containing 3 Protein; Periodontal Ligament; Sargassum; Signal Transduction

Ultraviolet (UV) B exposure is a prominent cause of skin aging and a contemporary subject of interest. The effects are progressing through the generation of reactive oxygen species (ROS) that alter cell signaling pathways related to inflammatory responses. The present study evaluates the protective effects of (7aR)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one (HTT) isolated from the edible brown algae Sargassum horneri against UVB protective effects in human dermal fibroblasts (HDFs). HTT treatment dose-dependently suppressed intracellular ROS generation in HDFs with an IC

Topics: Aquatic Organisms; Benzofurans; Fibroblasts; Humans; Inhibitory Concentration 50; Oxidative Stress; Phytotherapy; Sargassum; Skin; Skin Aging; Ultraviolet Rays

Neighbor detection and allelochemical response are important mediators in plant-plant interactions. Although there is increasing knowledge about plant allelochemicals released in response to the presence of competitors and involved in neighbor-derived signaling, less is known about which signaling chemicals are responsible for the neighbor-induced allelochemical response. Here, we experimentally demonstrate that (-)-loliolide, a carotenoid metabolite, acts as a signaling chemical in barnyardgrass-rice allelopathic interactions. The production of the rice allelochemicals momilactone B and tricin was increased in the presence of five biotypes of barnyardgrass. (-)-Loliolide was found in all the biotypes of barnyardgrass and their root exudates and rhizosphere soils. There were significant positive relationships between rice allelochemicals and (-)-loliolide concentrations across the biotypes of barnyardgrass. Furthermore, (-)-loliolide elicited the production of momilactone B and tricin. Comparative transcriptomic analysis revealed regulatory activity of (-)-loliolide on the diterpenoid and flavonoid biosynthesis pathway. The expression of key genes involved in the biosynthesis of momilactone B (CPS4, KSL4, and MAS) and tricin (CYP75B3 and CYP75B4) was up-regulated by (-)-loliolide. These findings suggest that (-)-loliolide acts as a signaling chemical and participates in barnyardgrass-rice allelopathic interactions. Allelopathic rice plants can detect competing barnyardgrass through the presence of this signaling chemical and respond by increasing levels of their allelochemicals to achieve an advantage for their own growth.

Topics: Allelopathy; Benzofurans; Echinochloa; Lactones; Oryza; Plant Roots

Topics: Antineoplastic Agents; Benzofurans; Carcinoma, Hepatocellular; Cell Survival; Hep G2 Cells; Humans; Lactones; Liver Neoplasms; Microalgae; Molecular Structure; Monoterpenes

Topics: Benzofurans; beta Catenin; Cell Movement; Cell Proliferation; Cell Survival; Cells, Cultured; Culture Media, Conditioned; Dermis; Hair Follicle; HEK293 Cells; Humans; Keratinocytes; Monoterpenes; Phosphorylation; Proto-Oncogene Proteins c-akt; Wnt Signaling Pathway

The liver X receptors (LXRs) are major regulators of lipogenesis, and their reduced activation by an inhibitor could be a treatment strategy for fatty liver disease. Small molecules originating from dietary food are considered suitable and attractive drug candidates for humans in terms of safety. In this study, an edible plant,

Topics: Acetyl-CoA Carboxylase; Animals; Benzofurans; Diet, High-Fat; Fatty Acid Synthases; Furans; Humans; Lignans; Lipogenesis; Liver; Liver X Receptors; Male; Mice, Inbred C57BL; Non-alcoholic Fatty Liver Disease; Plant Extracts; Primulaceae; Sterol Regulatory Element Binding Protein 1; Triglycerides

Jasmonic acid (JA) plays an important role in the induction of herbivore resistance in many plants. However, JA-independent herbivore resistance has been suggested. An herbivore-resistance-inducing substance was isolated from

Topics: Animals; Arabidopsis; Benzofurans; Carotenoids; Cell Death; Herbivory; Nicotiana; Solanum lycopersicum; Spodoptera; Tetranychidae; Tobacco Mosaic Virus

Loliolide is a monoterpenoid hydroxylactone present in freshwater algae that has anti-inflammatory and antiaging activity; however, its effects on ultraviolet-damaged skin have yet to be elucidated. This study investigated the antiapoptosis and wound-healing effects of loliolide using HaCaT cells (a human keratinocyte cell line). Loliolide inhibited the expression of reactive oxygen species (ROS) induced by ultraviolet radiation as well as wrinkle formation-related matrix metalloproteinase genes and increased the expression of the damage repair-related gene SIRT1. The apoptosis signaling pathway was confirmed by Western blot analysis, which showed that loliolide was able to reduce the expression of caspases 3, 8, and 9, which are related to ROS-induced apoptosis. In addition, Western blotting, reverse-transcription polymerase chain reaction (PCR), and real-time PCR analyses showed that loliolide enhanced the expression of the epidermal growth factor receptor signaling pathway (PI3K, AKT) and migration factors, such as K6, K16, and K17; keratinocyte growth factor; and inflammatory cytokines, such as interleukin (IL)-1, IL-17, and IL-22 expressed during the cellular scratching process, suggesting a putative wound-healing ability. Because of the antiapoptosis and antiscratching effects on skin of both loliolide and loliolide-rich

Topics: Antioxidants; Apoptosis; Benzofurans; Cell Line; Cell Movement; Cell Survival; Gene Expression; Humans; Keratinocytes; Matrix Metalloproteinases; Molecular Structure

Loliolide is a monoterpenoid hydroxylactone found in many algae, including fresh water green algae,

Topics: Animals; Antineoplastic Agents; Antioxidants; Benzofurans; Cell Line; Cell Line, Tumor; Chlorophyta; Gene Expression Regulation, Neoplastic; Humans; Melanins; Melanoma; Mice; Microphthalmia-Associated Transcription Factor; Monophenol Monooxygenase; Oxidative Stress

Without a vaccine, hepatitis C virus (HCV) remains a global medical and socio-economic burden, predisposing about 170 million carriers worldwide to end-stage liver diseases including cirrhosis and hepatocellular carcinoma. Although the recently developed direct-acting antivirals (DAAs) have revolutionized hepatitis C treatment, most of them are unsuitable for monotherapy due to risks of resistance, thus necessitating combination with interferon (IFN)-alpha, ribavirin, or additional DAAs. More importantly, the high cost associated with the DAAs restricts their accessibility to most parts of the world. Developing novel cost-effective anti-HCV therapeutics may help expand the scope of antivirals and treatment strategies against hepatitis C. Herein, we applied an activity-based and fraction-guided analysis of extracts from the medicinal plant Phyllanthus urinaria (P. urinaria), which yielded fraction 13 (F13) as possessing the most potent inhibitory activity against early viral entry of cell-culture HCV infection. Chemical analysis (silica gel chromatography followed by ESI LC-MS plus (1)H and (13)C NMR) of F13 identified loliolide (LOD), a monoterpenoid lactone, as a novel inhibitor of HCV entry. Specifically, LOD could efficiently inactivate HCV free virus particles, abrogate viral attachment, and impede viral entry/fusion, with minimal effect on viral replication/translation, particle production, and induction of type I IFN host antiviral immune response. ELISA-based binding analysis confirmed the monoterpenoid's ability in efficiently blocking HCV particle attachment to the host cell surface. Furthermore, LOD could inhibit infection by several genotypic strains of HCV. This is the first report characterizing P. urinaria and its bioactive compound LOD as potent HCV entry inhibitors, which merit further evaluation for development as candidate antiviral agents against hepatitis C.

Topics: Antiviral Agents; Benzofurans; Biological Products; Cell Line; Cells, Cultured; Chemical Fractionation; Dose-Response Relationship, Drug; Genotype; Hepacivirus; Humans; Inhibitory Concentration 50; Phyllanthus; Plant Extracts; Virus Assembly; Virus Internalization; Virus Replication

Cellular senescence influences tumor suppression and progress, tissue repair and regeneration, tissue and organismal aging, and age-related diseases. Aging intervention might be an advantageous target for prevention and treatment of diverse age-related diseases. In this study, we investigated whether (-)-loliolide purified from the crude extract of Polygonum aviculare exerted inhibitory activity against cellular senescence in human dermal fibroblasts (HDFs). (-)-Loliolide diminished senescence-associated β-galactosidase activity (SA-β-gal), the level of p21 protein, and the level of reactive oxygen species in senescent cells induced by adriamycin treatment. (-)-Loliolide also attenuated SA-β-gal activity in HDFs under replicative senescence. These findings imply that (-)-loliolide rescues cellular senescence in HDFs and might be useful for the development of dietary supplements or cosmetics that ameliorate tissue aging or age-associated diseases.

Topics: Benzofurans; Cellular Senescence; Dermis; Dose-Response Relationship, Drug; Fibroblasts; Humans; Plant Extracts; Polygonum

Four new norsesquiterpenes wilfordonols A-D (1-4), along with three known compounds, sarmentol B (5), boscialin (6), and (+)-loliolide (7), were isolated from the leaves of Tripterygium wilfordii Hook.f.. The structures of the new compounds were elucidated on the basis of their spectroscopic analysis, and the absolute configuration of the compounds was confirmed by CD and modified Mosher's method. At a concentration of 10 μM, compounds 4, 6, and 7 inhibited signal transducer and activator of transcription 1 translocation by 34.27 ± 1.02%, 48.93 ± 1.76%, and 70.31 ± 2.20%, respectively.

Topics: Benzofurans; Cyclohexanols; Drugs, Chinese Herbal; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plant Leaves; Sesquiterpenes; Tripterygium

A bioassay-guided purification of an EtOAc extract of the leaves of Croton mauritianus using a chikungunya virus-cell-based assay led to the isolation of 12-O-decanoylphorbol-13-acetate (1) and the new 12-O-decanoyl-7-hydroperoxy-phorbol-5-ene-13-acetate (2), along with loliolide, vomifoliol, dehydrovomifoliol, annuionone D and bluemol C. The planar structure and the relative configuration of compound 2 were elucidated based on spectroscopic analysis, including 1D- and 2D-NMR experiments, mass spectrometry, and comparison with literature data. Compounds 1 and 2 inhibited chikungunya virus-induced cell death in cell culture with EC50s of 2.4±0.3 and 4.0±0.8 μM, respectively.

Topics: Antiviral Agents; Benzofurans; Butanols; Chikungunya virus; Croton; Cyclohexanones; Diterpenes; Microbial Sensitivity Tests; Norisoprenoids; Phorbol Esters; Plant Leaves; Virus Replication

Three chemicals, veratric acid, maltol, and (−)-loliolide, were isolated from crabgrass and their structures were identified by spectroscopic analysis. The chemicals were detected in crabgrass root exudates and rhizosphere soils, and their concentrations ranged from 0.16 to 8.10 μg/g. At an approximate concentration determined in crabgrass root exudates, all chemicals significantly inhibited the growth of wheat, maize, and soybean and reduced soil microbial biomass carbon. Phospholipid fatty acid profiling showed that veratric acid, maltol, and (−)-loliolide affected the signature lipid biomarkers of soil bacteria, actinobacteria, and fungi, resulting in changes in soil microbial community structures. There were significant relationships between crop growth and soil microbes under the chemicals' application. Chemical-specific changes in the soil microbial community generated negative feedback on crop growth. The results suggest that veratric acid, maltol, and (−)-loliolide released from crabgrass may act as allelochemicals interfering with crop growth and the soil microbial community.

Topics: Actinobacteria; Benzofurans; Biomarkers; China; Crops, Agricultural; Digitaria; Fungi; Glycine max; Gram-Negative Bacteria; Herbicides; Molecular Structure; Pheromones; Plant Exudates; Plant Roots; Pyrones; Soil; Soil Microbiology; Triticum; Vanillic Acid; Zea mays

The tea from the white mulberry (Morus alba L.) leaf is a worldwide known traditional medicine of type II diabetes. Here, we report the investigation of the dichloromethane-soluble fraction obtained in a 0.24% m/m yield from the hot water extract of mulberry leaves. A significant, dose-dependent activity was found by means of the 24-h glucose consumption of fully differentiated adipocytes both in the absence and presence of insulin. The fraction was characterized by HPLC-DAD, GC-MS and GC-FID. The main constituent (40.3% by means of GC-FID) was isolated and identified as loliolide by EIMS, HRESIMS and NMR spectroscopy. In the active fraction benzyl alcohol, ethyl benzoate, t-cinnamic acid, p-hydroxyacetophenone, t-coniferyl alcohol and synapil alcohol were also identified by GC-MS and quantified by GC-FID (0.7, 1.3, 1.5, 2.9, 7.5 and 2.6%, respectively).

Topics: 3T3-L1 Cells; Adipocytes; Animals; Benzofurans; Hypoglycemic Agents; Mice; Morus; Plant Extracts; Plant Leaves

A new eudesmanolide, 1β,3β-dihydroxy-eudesman-11(13)-en-6α,12-olide (1) was isolated and identified from Taraxacum mongolicum, together with two known compounds, 1β,3β-dihydroxyeudesman-6α,12-olide (2) and loliolide (3). The structure of 1 was established by analysis of its physical and spectroscopic data. 1 was found to have an inhibitory activity on nitric oxide production with an IC(50) of 38.9 μM in activated RAW 264.7 cells.

Topics: Animals; Benzofurans; Cell Line; Inhibitory Concentration 50; Macrophages; Mice; Nitric Oxide; Sesquiterpenes; Sesquiterpenes, Eudesmane; Taraxacum

Five new labdane diterpenes, thessalines A, B, and D, 14β-hydroxythessaline A, and 14β-hydroxythessaline B (1-5, resp.) were isolated from the aerial parts of Marrubium thessalum, along with the known labdane diterpene deacetylvitexilactone (6) and the methoxylated flavones 4',7-dimethylapigenin and salvigenin. (3S,5R)-Loliolide was also found in the same source. Their structures were established by 1D- and 2D-NMR (COSY, HSQC, HMBC, NOESY, and ROESY) and MS analyses. The plant produces a great variety of labdane-type diterpenes, with variations in functionalities, particularly in the side chain. Their structures could be of chemotaxonomic significance for the genus Marrubium.

Topics: Benzofurans; Diterpenes; Flavones; Marrubium; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plants, Medicinal

Loliolide content was determined in 13 marine algae including red, brown and green algae collected from the Black Sea, the Dardanelles and the Aegean Sea. Identification and quantification were performed by gas chromatography-mass spectrometry. The loliolide content in green alga is 1.76 microg g(-1), ranges from 0.14 to 4.35 microg g(-1) in red and from 0.18 to 4.83 microg g(-1) in brown algae. The results obtained are in the same range as previously reported for algae, as well as terrestrial plants. This article represents the first report of loliolide occurrence in green algae.

Topics: Benzofurans; Eukaryota; Molecular Structure

To study the chemical constituents of ethanolic extract from herbs of Dicliptera chinensis.. The compounds were separated by silica gel column chromatography, preparation TLC and reverse phase HPLC, their structures were identified by the spectroscopic methods of UV, NMR and MS.. Seven compounds were isolated from ethyl acetate extract. Their structure were identified as octasulphur (1), secoisolariciresinol dimethyl ether diacetate (2), 5-methoxy-4, 4'-di-O-methyl secolariciresinol (3), chinensinaphthol methyl ester (4), loliolide (5), beta-sitosterol 3-O-beta-D-glucopyranoside (6) and stigmasterol 3-O-beta-D-glucopyranoside (7).. All the compounds except 6 were obtained from the plants of Dicliptera for the first time.

Topics: Acanthaceae; Benzofurans; Glucosides; Plants, Medicinal; Sitosterols

To investigate the chemical constituents of red alga Corallina pilulifera.. Compounds were isolated by normal phase silica gel and Sephadex LH - 20 gel column chromatography, reverse phase HPLC and recrystallization. Their structures were elucidated by spectroscopic methods including MS, 1H-NMR, 13C-NMR, HSQC, HMBC. Cytotoxicity of the compounds was screened by using standard MTT method.. Seven compounds were isolated from red alga C. pilulifera, their structures were identified as (E) -phytol epoxide (1), phytenal (2), phytol (3), dehydrovomifoliol (4), loliolide (5), 3beta-hydroxy-5alpha, 6alpha-epoxy-7-megastigmene-9-one (6), 4-hydroxybenzaldehyde (7).. All of the compounds were obtained from this species for the first time. These compounds were inactive (IC50 > 10 microg x mL(-1)) in the MTT assay.

Topics: Benzaldehydes; Benzofurans; Cell Line, Tumor; Humans; Phytol; Rhodophyta

A mixture of loliolide 1 (> 85%) and paniculatadiol 2 (< 15%) was obtained from the ethyl acetate leaf extract of Pterocarpus indicus by silica gel chromatography, while the air-dried flowers afforded lupeol 3 and phytol esters 4. The structures of 1-4 were determined by NMR spectroscopy. Antimicrobial tests on a mixture of 1 and 2 indicated that it has moderate activity against Candida albicans and low activity against Pseudomonas aeruginosa, Escherichia coli, and Aspergillus niger. It was found inactive against Staphylococcus aureus, Bacillus subtilis, and Trichophyton mentagrophytes.

Topics: Anti-Infective Agents; Bacteria; Benzofurans; Flowers; Fungi; Molecular Structure; Pentacyclic Triterpenes; Plant Leaves; Pterocarpus; Terpenes; Triterpenes

Topics: Antineoplastic Agents, Phytogenic; Benzofurans; China; Galactitol; Gallic Acid; Plants, Medicinal; Pyrones; Succinates; Succinic Acid

Topics: Animals; Antineoplastic Agents; Benzofurans; Drug Screening Assays, Antitumor; Humans; Indian Ocean; KB Cells; Leukemia P388; Mollusca; Plants, Medicinal; Polycyclic Aromatic Hydrocarbons; Xanthophylls; Zeaxanthins