lignans and syringaresinol

The bark and leaves of Eucommia ulmoides Oliv (Eucommiaceae) and "Siberian ginseng" (Ezoukogi in Japanese) prepared from the root bark or stem bark of Eleutherococcus senticosus Maxim (Acanthopanax senticosus Harms) have been used as tonic and anti-stress drug. The extracts of Eucommia showed anti-hypertensive, anti-complementary, anti-oxidative, and anti-gastric ulcer effects, and promoting collagen synthesis, accelating granuloma formation, and other pharmacological effects. The Siberian ginseng exhibited anti-fatigue, anti-stress, immuno-enhancing effect, CNS activity, and anti-depressive effect. By now, 40, 28, and 10 compounds have been isolated from Eucommia ulmoides bark, Eucommia ulmoides leaves, and Siberian ginseng, respectively, and their structures were elucidated. Their pharmacological activities were mainly due to lignans and iridoid glycosides.

Topics: Adjuvants, Immunologic; Animals; Anti-Ulcer Agents; Antihypertensive Agents; Antioxidants; Collagen; Coumarins; Depression; Eleutherococcus; Eucommiaceae; Fatigue; Furans; Glucosides; Humans; Iridoid Glucosides; Iridoids; Lignans; Plant Extracts; Rats; Stress, Physiological

Osteoarthritis (OA) is a now regarded as a worldwide whole joint disease with synovial inflammation, cartilage degeneration, and subchondral sclerosis. Non-steroidal anti-inflammatory drugs (NSAIDs) are commonly used drugs for OA treatment which only relieve the symptoms and restrain the progression of OA. However, various severe adverse effects often occur in patients with long-term NSAIDs use, which heavily burdens the healthcare system and impacts the quality of life. Therefore, it is much imperative to identify alternative drugs with increased efficacy. Syringaresinol (Syr), a naturally occurring phytochemical which belonging to the lignan group of polyphenols, shows anti-tumor and anti-oxidant activities, which to benefit human health. Studies has shown Syr can regulate the inflammatory response by modulating the secretion and expression level of cytokines IL-6, IL-8, and tumor necrosis factor (TNF)-α. it also shows the inhibitory effect on NF-κB pathway in mouse cells. In the present study, we aimed to demonstrate the anti-inflammatory effects of Syr in OA. In vitro Syr treatment in IL-1β-activated mouse chondrocytes significantly restrained the expression of NO, PGE2, IL-6, TNF-α, INOS, COX-2 and MMP-13. Moreover, it considerably ameliorated the degradation of aggrecan and collagen II. Furthermore, the phosphorylation of the NF-kB signaling pathway was significantly suppressed by Syr. Moreover, in vivo, the cartilage degeneration was attenuated and the increased Osteoarthritis Research Society International (OARSI) scores were reversed in the DMM + Syr group, comprared to those in the DMM group. In sum, our study demonstrated that Syr can attenuate the inflammation in vitro and further verified its effect on OA in vivo. Thus, Syr might be a potent therapeautic alternative for OA treatment.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Cells, Cultured; Chondrocytes; Humans; Inflammation; Interleukin-1beta; Interleukin-6; Lignans; Mice; NF-kappa B; Osteoarthritis; Quality of Life

Lignans have attracted much attention from researchers because of their wide distribution and industrial applications in plants, as well as the remarkable diversity of their biological activities. As the literature has mainly focused on the extraction and identification of monomeric compounds of lignans, most lignans in Dendrobium officinale, a traditional Chinese medicine with a long cultivation history and rich sources, have not been detected using quality control methods. The aim of this study was to identify the lignans in Dactilon officinale.. High-performance liquid chromatography (HPLC) coupled with diode array detection and HPLC multiple-stage tandem mass spectrometry was used to identify the chemical constituents of D. officinale. Simultaneously, the characteristic chromatograms of D. officinale were established. Additionally, a method was established to determine the content of syringaresinol-4,4'-di-O-β-D-glucoside, syringaresinol-4-O-β-D-glucoside and syringaresinol.. Thirty-three lignans, including 17 tetrahydrofuran lignans, two dibenzylbutane lignans, three aryl tetrahydronaphthalene lignans and 11 8-O-4'-neolignans, were tentatively identified from the methanol extract of the stems of D. officinale. This is the first report of 8-O-4'-neolignans from D. officinale. In addition, a total of eight characteristic peaks were marked in characteristic chromatograms, which were identified as lyoniresinol-9'-O-β-D-glucoside, syringaresinol-4,4'-di-O-β-D-glucoside, 8-hydroxy-syringaresinol-4-O-β-D-glucoside, 5,5'-dimethoxy-lariciresinol-4-O-β-D-glucoside, syringaresinol-4-O-β-D-glucoside, 4-hydroxy-3,3',5,5'-tetramethoxy-8,4'-oxyneoligna-7'-ene-9,9'-diol-9-O-β-D-glucoside, 4-hydroxy-3,3',5,5'-tetramethoxy-8,4'-oxyneoligna-7'-ene-9,9'-diol-4-O-β-D-glucoside and syringaresinol. Our results showed that no significant difference occurred in lignan composition among the 99 batches of D. officinale from different sources. However, the peak areas of the lignans of D. officinale planted under simulated wild culture were generally higher than those in greenhouses, and showed an upward trend with the increase in growth years. The average contents of syringaresinol-4,4'-di-O-β-D-glucoside, syringaresinol-4-O-β-D-glucoside and syringaresinol were 10.112-179.873, 51.227-222.294 and 6.368-120.341 μg/g, respectively.. This study provided a basis for improving the quality control of D. officinale and could provide references for the identification of lignans in other Dendrobium species.

Topics: Dendrobium; Glucosides; Lignans; Mass Spectrometry

Acute lung injury (ALI) is a common lung disease characterized by severe acute inflammatory lung injury in patients with sepsis. Syringaresinol (SYR) has been reported to have anti-apoptotic and anti-inflammatory effects, but whether it could prevent pyroptosis to improve sepsis-induced ALI remains unclear. The purpose of this work was to examine the impact of SYR on sepsis-induced ALI and investigate the underlying mechanisms. The ALI model was induced by caecal ligation and puncture (CLP) in C57BL/6 mice, structural damage in the lung tissues was determined using haematoxylin and eosin (HE) staining, and the levels of related inflammatory cytokines and macrophage polarization were examined by enzyme-linked immunosorbent assays (ELISAs) and flow cytometry, respectively. The activation of the NLRP3 inflammasome and the protein levels of TLR4, NF-κB and MAPKs was measured by western blotting. The results demonstrated that SYR pretreatment significantly reduced lung tissue histological damage, inhibited the production of proinflammatory cytokines and albumin in bronchoalveolar lavage fluid (BALF), and decreased myeloperoxidase (MPO) levels, thereby alleviating lung tissue injury. Meanwhile, septic mice treated with SYR displayed a higher survival rate and lower percentage of M1 macrophages in the BALF and spleen than septic mice. In addition, lung tissues from the CLP + SYR group exhibited downregulated protein expression of NLRP3, ASC, GSDMD caspase-1 p20 and TLR4, along with decreased phosphorylated levels of NF-κB, ERK, JNK and P38, indicating that SYR administration effectively prevented CLP-induced pyroptosis in the lung. SYR also suppressed LPS-induced pyroptosis in RAW 264.7 cells by inhibiting the activation of the NLRP3 inflammasome, which was abolished by an oestrogen receptor-β (ERβ) antagonist (PHTPP). In conclusion, SYR exerted protective effects on CLP-induced ALI via the oestrogen receptor-β signalling pathway.

Topics: Acute Lung Injury; Animals; Furans; Lignans; Mice; Mice, Inbred C57BL; Pyroptosis; Receptors, Estrogen; Sepsis

The mortality of sepsis-induced cardiac dysfunction (SICD) is very high due to the complex pathophysiological mechanism. Syringaresinol (SYR) is a natural abstract which possesses anti-inflammatory property. The present study aims was to identify the protective impact of SYR on sepsis-induced cardiac dysfunction and investigate the specific mechanisms. We found that SYR improved the cardiac function and alleviated myocardial injury in mice that subjected to cecal ligation and puncture, in addition, SIRT1 expression was significantly elevated after SYR treatment compared to sepsis group both in vivo and in vitro, along with suppression of NLRP3 activation and proinflammatory cytokines release. However, SIRT1 inhibitor EX427 abolished the impact of SYR on LPS-induced pyroptosis in cardiomyocytes. Furthermore, molecular docking analysis predicted that there is high affinity between SYR and estrogen receptor (ER), ER inhibitor ICI182780, the specific ERβ inhibitor PHTP and the specific ERαinhibitor AZD9496 were used to examine the role of ER in the protective effect of SYR against SICD, and the results suggested that ER activation was essential for the cardioprotective function of SYR. In conclusion, SYR ameliorates SICD via the ER/SIRT1/NLRP3/GSDMD pathway.

Topics: Animals; Cardiotonic Agents; Cinnamates; Disease Models, Animal; Fulvestrant; Furans; Heart; Heart Diseases; Humans; Indoles; Inflammation; Lignans; Male; Mice; Molecular Docking Simulation; Myocardium; Pyroptosis; Receptors, Estrogen; Sepsis; Sirtuin 1

Phytoestrogens are dietary estrogens having similar structure as of estrogen. Some of these phytoestrogens are androgen receptor (AR) antagonists and exhibit preventive role in the prostate cancer. However, in androgen-independent prostate cancer (AIPC) the ARs were mutated (T877A, W741L, F876L, etc.) and these mutant ARs convert the antagonist to agonist. Our aim in this study is to find phytoestrogens that could function as an antagonist with wild and mutant ARs. The phytoestrogens were analyzed for binding affinity with wild and mutant ARs in agonist and antagonist conformations. The point mutations were carried out using Chimera. The antagonist AR conformation was modeled using Modeller. We hypothesize that the compounds having binding affinity with agonist AR conformation could not function as a full or pure antagonist. Most of the phytoestrogens have binding affinity with agonist AR conformation contradicting previous results. For example, genistein which is a widely studied isoflavone has known AR antagonist property. However, in our study, it had good binding affinity with agonist AR conformation. Hence, to confirm our hypothesis, we tested genistein in LNCaP (T877A mutant AR) cells by qPCR studies. The genistein functioned as an antagonist only in the presence of an androgen indicting a partial agonist type of activity. The

Topics: Androgen Receptor Antagonists; Furans; Humans; Lignans; Male; Molecular Docking Simulation; Molecular Dynamics Simulation; Prostatic Neoplasms; Prostatic Neoplasms, Castration-Resistant; Receptors, Androgen

Albiziae Cortex (AC) is a well-known traditional Chinese medicine with sedative-hypnotic effects and neuroprotective ability. However, the bioactive components of AC responsible for the neuro-protective actitivity remain unknown. Here, we investigated the anti-neuroinflammatory effects of (-)-syringaresinol (SYR) extracted from AC in microglia cells and wild-type mice. As a result, (-)-SYR significantly reduced lipopolysaccharide (LPS)-induced production of interleukin - 6 (IL-6), tumor necrosis factor α (TNF-α), interleukin -1 beta (IL-1β), cycloxygenase-2 (COX-2), and nitric oxide (NO) in BV2 microglia cells. (-)-SYR also significantly reduced M1 marker CD40 expression and increased M2 marker CD206 expression. Moreover, we found that (-)-SYR inhibited LPS-induced NF-κB activation by suppressing the translocation of NF-κB p65 into the nucleus in a concentration-dependent manner. Meanwhile, estrogen receptor β (ERβ) was found to be implied in the anti-inflammatory activity of (-)-SYR in BV2 microglia. In vivo experiments revealed that administration of (-)-SYR in mice significantly reduced microglia/astrocytes activation and mRNA levels of proinflammatory mediators. Taken together, our data indicated that (-)-SYR exerted the anti-neuroinflammatory effects by inhibiting NF-κB activation and modulation of microglia polarization, and via interaction with ERβ. The anti-neuroinflammatory activity of (-)-SYR may provide a new therapeutic avenue for the treatment of brain diseases associated with inflammation.

Topics: Albizzia; Animals; Anti-Inflammatory Agents; Cell Survival; Cytokines; Estrogen Receptor beta; Furans; Lignans; Lipopolysaccharides; Macrophage Activation; Male; MAP Kinase Signaling System; Mice; Mice, Inbred C57BL; Microglia; Neuroinflammatory Diseases; Oncogene Protein v-akt; Transcription Factor RelA

Ultraviolet (UV) irradiation induces detrimental changes in human skin which result in photoaging. UV-induced intracellular changes cause degradation of extracellular matrix (ECM). UV-stimulated cleavage of collagen in ECM occurs via matrix metalloproteinases (MMPs). (±)-syringaresinol (SYR), a phytochemical which belongs to the lignan group of polyphenols, was investigated for its ability to reverse the UVA-induced changes in human HaCaT keratinocytes and dermal fibroblasts (HDFs) in vitro. Effect of SYR on UVA-induced changes was investigated by production and activation of MMPs and its transcriptional upstream effectors; mitogen-activated protein kinases (MAPKs) and pro-inflammatory mediators. Levels of expression were determined using ELISA, RT-PCR and immunoblotting. UVA irradiation stimulated the production of MMP-1 and inhibited collagen production. SYR treatment suppressed MMP-1 and enhanced collagen production in UVA-irradiated HaCaT keratinocytes and HDFs. SYR repressed the UV-induced phosphorylation of p38, ERK and JNK MAPKs in HaCaT keratinocytes while only suppressing JNK phosphorylation in HDFs. In addition, SYR was able to inhibit UVA-induced production of inflammatory cytokines; TNF-α, COX-2, IL-1β and IL-6. Moreover, SYR suppressed the activator protein-1 (AP-1), a heterodimer of phosphorylated transcription factors c-Jun and c-Fos. SYR-treatment decreased nuclear levels of activated c-Fos and c-Jun as a mechanism to inhibit UVA-induced transcriptional activities leading to MMP-1 production. In conclusion, current results demonstrated that SYR could inhibit UVA-induced upregulation of MMP-1 by suppressing MAPK/AP-1 signaling in HaCaT keratinocytes and HDFs. Therefore, SYR was suggested as a potential compound with antiphotoaging properties against UVA-induced skin aging.

Topics: Collagen; Enzyme-Linked Immunosorbent Assay; Fibroblasts; Furans; HaCaT Cells; Humans; Inflammation; Keratinocytes; Lignans; MAP Kinase Signaling System; Matrix Metalloproteinase 1; p38 Mitogen-Activated Protein Kinases; Phosphorylation; Skin; Skin Aging; Transcription Factor AP-1; Ultraviolet Rays

Syringaresinol (SYR) is a phenolic compound, which could be found in various cereals and medicinal plants. It exerts both anti-inflammatory and antioxidant pharmacological properties. However, little is known about the effect of SYR on modulating diabetic cardiomyopathy. The present study aimed to investigate the pharmacodynamic effect of SYR on diabetic cardiomyopathy and the underlying molecular mechanism.. In STZ-induced type 1 diabetic mice, orally administration with SYR in every other day for 8 weeks significantly improves cardiac dysfunction and preventes cardiac hypertrophy and fibrosis. The macrophage infiltration and oxidative stress biomarkers are also suppressed by SYR without affecting hyperglycemia and body weight. In neonatal cardiomyocytes, high glucose-induced cell apoptosis and fibrosis are potently decreased by SYR, and the inflammatory response and oxidant stress are also alleviated by SYR incubation. Mechanistically, SYR may exert protective effects by restoring suppression of antioxidant kelch-like ECH-associated protein 1 (Keap1)/nuclear factor-E2-related factor 2 (Nrf2) system and abnormal activation of transforming growth factor-β (TGF-β)/mothers against decapentaplegic homolog (Smad) signaling pathway in vitro and in vivo.. The results indicated that SYR could be a potential therapeutic agent for the treatment of diabetic cardiomyopathy by inhibiting inflammation, fibrosis, and oxidative stress. The signaling pathway of Keap1/Nrf2 and TGF-β/Smad could be used as therapeutic targets for diabetic complications.

Topics: Animals; Apoptosis; Cardiotonic Agents; Diabetes Mellitus, Experimental; Diabetes Mellitus, Type 1; Diabetic Cardiomyopathies; Fibrosis; Furans; Hyperglycemia; Kelch-Like ECH-Associated Protein 1; Lignans; Male; Mice, Inbred C57BL; Myocarditis; Myocytes, Cardiac; NF-E2-Related Factor 2; Oxidative Stress

Phytochemical investigation of the whole plant of Filago vulgaris Lam. (Asteraceae) resulted in the isolation and characterization of seven compounds, including a rare methoxylated flavonol (araneol), tetrahydrofurofuranolignans (pinoresinol and syringaresinol), p-hydroxybenzaldehyde, vanillin, vanillic acid and scopoletin. The structures of the compounds were determined by NMR and mass spectroscopy. All compounds were first obtained from this species and reported for the genus Filago. Our results demonstrate that highly methoxylated flavonols lacking substituents on ring B and lignans can be regarded as taxonomic markers for the tribe Inuleae. The lipophilic extract of F. vulgaris was found to have antiproliferative activity against HeLa cells (62.1±0.9% inhibition at 30 μ/ml), and araneol was highly effective against this tumour cell line (IC

Topics: Asteraceae; Cell Line, Tumor; Cell Proliferation; Flavonoids; Flavonols; Furans; HeLa Cells; Humans; Lignans; MCF-7 Cells; Plant Extracts

A new lignan, named oleralignan (

Topics: Antioxidants; Free Radical Scavengers; Furans; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Extracts; Portulaca; Spectrometry, Mass, Electrospray Ionization

Topics: Astragalus Plant; Astragalus propinquus; Benzofurans; China; Drugs, Chinese Herbal; Furans; Glucosides; Heterocyclic Compounds, 4 or More Rings; Isoflavones; Lignans; Molecular Structure; Phenols; Plant Roots

Aging is characterized by accumulation of chronic and irreversible oxidative damage, chronic inflammation, and organ dysfunction. Superoxide dismutase (SOD) serves as a major enzyme for cellular superoxide radical metabolism and physiologically regulates cellular redox balance throughout the body. Copper/zinc superoxide dismutase-deficient (SOD1

Topics: Animals; Atrophy; Biopsy, Needle; Blotting, Western; Copper; Forkhead Box Protein O3; Furans; Immunohistochemistry; Lignans; Matrix Metalloproteinase 2; Mice; Mice, Hairless; Polymerase Chain Reaction; Skin Aging; Superoxide Dismutase; Superoxide Dismutase-1; Treatment Outcome

A new sesquiterpene kalinturoside A (1), and 17 known compounds friedelan-3-ol (2), 24-ethyl-5a-cholesta-7, 22(E)-dien-3-one (3), friedelin (4), syringaresinol (5), α-spinasterol (6), ciwujiatone (7), syringic acid (8), scopoletin (9), apocynin (10), 1-(3-hydroxy-4, 5-dimethoxyphenyl)ethan-1-one (11), apigenin (12), 5-hydroxymethylfurfural (13), stigmasterol-3-O-β-d-glucopy-ranoside (14), bidenoside C (15), citrusin (16), irioresinol A (17) and syringaresinol-4-O-β-d-glucopyranoside (18) were isolated from the herbs of Kalimeris integrifolia. The structures of these compounds were elucidated using spectroscopic techniques such as NMR and MS. All of the compounds were isolated from this genus for the first time.

Topics: Alkynes; Antineoplastic Agents, Phytogenic; Asteraceae; Cell Line, Tumor; Drug Screening Assays, Antitumor; Drugs, Chinese Herbal; Furaldehyde; Furans; Glucosides; Humans; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Sesquiterpenes; Stigmasterol; Triterpenes

Many neuromodulating drugs acting on the nervous system originate from botanical sources. These plant-derived substances modulate the activity of receptors, ion channels, or transporters in neurons. Their properties make the substances useful for medicine and research. Here, we show that the plant lignan (+)-syringaresinol (SYR) suppresses excitatory synaptic transmission via presynaptic modulation. Bath application of SYR rapidly reduced the slopes of the field excitatory postsynaptic potentials (fEPSPs) at the hippocampal Schaffer collateral (SC)-CA1 synapse in a dose-dependent manner. SYR preferentially affected excitatory synapses, while inhibitory synaptic transmission remained unchanged. SYR had no effect on the conductance or the desensitization of AMPARs but increased the paired-pulse ratios of synaptic responses at short (20-200 ms) inter-stimulus intervals. These presynaptic changes were accompanied by a reduction of the readily releasable pool size. Pretreatment of hippocampal slices with the G

Topics: Animals; Central Nervous System Stimulants; Dose-Response Relationship, Drug; Electric Stimulation; Excitatory Amino Acid Antagonists; Female; Furans; Glutamic Acid; HEK293 Cells; Hippocampus; Humans; In Vitro Techniques; Lignans; Male; Mice; Patch-Clamp Techniques; Picrotoxin; Quinoxalines; Receptors, AMPA; Signal Transduction; Synaptic Transmission

In this study, we evaluated cytotoxicity of chemicals isolated from Torricellia tiliifolia DC. on Spodoptera litura (SL-1) cell line. Among the isolated compounds, 4-hydroxy-3-methoxycinnamaldehyde, 3,5-dimethoxy-4-hydroxycinnamaldehyde, and syringaresinol inhibited SL-1 cell survival in both dose- and time-dependent manners. Meanwhile, the in vivo insecticidal activity test revealed that 4-hydroxy-3-methoxycinnamaldehyde and 3,5-dimethoxy-4-hydroxycinnamaldehyde showed obvious insecticidal activities. These two compounds exhibited toxicity to SL-1 cells by inducing cellular morphological changes including shape change, cell shrinkage, vacuolation, cell membrane blebbing and chromatin condensation and apoptosis. 4-hydroxy-3-methoxycinnamaldehyde and 3,5-dimethoxy-4-hydroxycinnamaldehyde showed the most effect on mitochondrial membrane depolarization at 24h and 72h respectively and induced the apoptosis at a late time point 72h. Our results suggest that 4-hydroxy-3-methoxycinnamaldehyde and 3,5-dimethoxy-4-hydroxycinnamaldehyde inhibit SL-1 survival by inducing apoptosis.

Topics: Acrolein; Animals; Apoptosis; Cell Line; Dose-Response Relationship, Drug; Furans; Lignans; Magnoliopsida; Membrane Potential, Mitochondrial; Plant Extracts; Spodoptera

Two new sucrose derivatives, namely, belamcanosides A (

Topics: Adaptor Proteins, Vesicular Transport; Cell Survival; Cholesterol; Furans; Gene Expression Regulation; Hep G2 Cells; Humans; Hydroxymethylglutaryl CoA Reductases; Iris Plant; Lignans; Phenols; Plant Extracts; Quercetin; Receptors, LDL; Seeds; Squalene Monooxygenase; Stilbenes

We examined the anti-inflammatory effects of (+)-syringaresinol (SGRS), a lignan isolated from Rubia philippinensis, in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells using enzyme-based immuno assay, Western blotting, and RT-PCR analyses. Additionally, in vivo effects of SGRS in the acute inflammatory state were examined by using the carrageenan-induced hind paw edema assay in experimental mice. As a result, treatment with SGRS (25, 50, and 100 μM) inhibited protein expression of lipopolysaccharide-stimulated inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and nuclear factor kappa B (NF-κB) as well as production of nitric oxide (NO), prostaglandin E2 (PGE2), tumor necrosis factor-alpha (TNF-α), interleukin-1beta (IL-1β), and interleukin-6 (IL-6) induced by LPS. Moreover, SGRS also reduced LPS-induced mRNA expression levels of iNOS and COX-2, including NO, PGE2, TNF-α, IL-1β, and IL-6 cytokines in a dose-dependent fashion. Furthermore, carrageenan-induced paw edema assay validated the in vivo anti-edema effect of SGRS. Interestingly, SGRS (30 mg/kg) suppressed carrageenan-induced elevation of iNOS, COX-2, TNF-α, IL-1β, and IL-6 mRNA levels as well as COX-2 and NF-κB protein levels, suggesting SGRS may possess anti-inflammatory activities.

Topics: Animals; Anti-Inflammatory Agents; Dose-Response Relationship, Drug; Edema; Extracellular Signal-Regulated MAP Kinases; Furans; Inflammation Mediators; Lignans; Lipopolysaccharides; MAP Kinase Signaling System; Mice; Mice, Inbred ICR; NF-kappa B; RAW 264.7 Cells

In this study, the characterization of chemical constituents and biological activity of the roots of

Topics: Antioxidants; Chromatography, High Pressure Liquid; Coumarins; Furans; Glucosides; Humans; Inhibitory Concentration 50; Inositol; Lignans; Magnetic Resonance Spectroscopy; Phenol; Plant Extracts; Plant Roots; Receptors, Scavenger; Taraxacum

Topics: Amines; Benzhydryl Compounds; Epoxy Resins; Furans; Green Chemistry Technology; Lignans; Phenols; Polymers

Sixteen lignanoids were isolated from an aqueous extract of the commonly used Chinese traditional medicine Dangshen, the dried roots of Codonopsis pilosula, by using a combination of various chromatographic techniques, including silica gel, macroporous adsorbent resin, MCI resin, sephadex LH-20, and reversed phase semi-preparative HPLC. On the basis of spectral data analysis, their structures were elucidated and identified as（-）-（7R,7’R,8R,8’S）-4,4’-dihydroxy-3,3’,5,5’,7-pentamethoxy-2,7’-cyclolignane（1）,（-）-（7R,8S）- dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranosyl-（1’’’→2’’）-β-D-glucopyranoside（2）,（-）-（7R,8S）- dihydrodehydrodiconiferyl alcohol（3）,（+）-（7S,8R）-dehydrodiconiferyl alcohol（4）,（+）-balanophonin（5）,（+）- demethoxypinoresinol（6）,（+）-pinoresinol（7）,（+）-epipinoresinol（8）,（-）-syringaresinol（9）,（-）-medioresinol（10）,（-）-lariciresinol（11）,（-）-secoisolariciresinol（12）,（-）-ent-isolariciresinol（13）,（+）-（7S,8S）-3-methoxy-3’,7- expoxy-8,4’-neolignan-4,9,9’-triol（14）,（+）-（7S,8R）-3’,4-dihydroxy-3-methoxy-8,4’-neolignan（15）, and（-）-（7R,8R）-3’,4-dihydroxy-3-methoxy-8,4’-neolignan（16）. All these compounds were isolated from C. pilosula for the first time, while compound 1 is a new natural product of 2,7’-cyclolignan and 2 is a new 4’,7-epoxy- 8,3’-neolignan diglucoside. Compound 12 showed activity against Fe(2+)-cysteine induced rat liver microsomal lipid peroxidation with an inhibition ratio of（63.4 ± 8.3） % at 1×10(-5) mol·L(-1).

Topics: Animals; Butylene Glycols; Codonopsis; Drugs, Chinese Herbal; Furans; Lignans; Microsomes, Liver; Molecular Structure; Plant Extracts; Plant Roots; Rats

To study the phenylpropanoid constituents of Smilax trinervula.. The chemical constituents were isolated and purified by macroporous adsorption resin chromatography, gel chromatography and high performance liquid chromatography. Their structures were identified by spectroscopic analysis and comparison with literatures.. Nine phenylpropanoid compounds were isolated and their structures were identified as( +)-lyoniresin-4-yl β-D-glucopyranoside( 1),(-)-8’-epilyoniresin-4-yl β-glucopyranoside( 2),( +)-lyoniresin-4’-yl β-glucopyranoside( 3),(-)-lyoniresinol-2α-O-β-D-glucopyranoside( 4),( +)-lyoniresinol( 5),icariol A2( 6),icariol A2-4-O-β-D-glucopyranoside( 7),7S,7’S,8R,8’R-icariol A2-9-O-β-D-glucopyranoside( 8) and( +)-syringaresinol-4’-O-β-D-glucopyranoside( 9).. All the compounds are isolated from Smilax genus for the first time.

Topics: 1-Propanol; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Furans; Lignans; Plant Extracts; Smilax

To investigate the chemical constituents of Clematis aethusifolia,a traditional Mongolian medicine for resolving hard lump.. Bioactive guided isolation and purification of Clematis aethusifolia was performed by normal and reverse phase column chromatography, Sephadex LH-20 and preparation HPLC. The structures were identified by 1D,2D-NMR and MS spectral analysis and comparison with literature data. Cytotoxicity of compounds were determined by CCK-8 cell staining method for detecting growth inhibition to five kinds of human solid tumor cell lines.. Eight compounds were isolated and identified as vanillicacid( 1),protocatechuic acid( 2),( +)-pinoresinol diglucoside( 3),( +)-pinoresinol-4’-O-β-D-glucopyranoside( 4),( +)-syringaresinol-4’-O-β-Dglucopyranoside( 5),7,9,9’-trihydroxy-3,3’-dimethoxy-8-O-4’-neolignan-4-O-β-D-glucopyranoside( 6),butyl-β-D-fructopyranoside( 7),butyl-β-D-fructofuranoside( 8). Compounds 2,8 showed strong cytotoxic activity.. All the compounds are isolated from this plant for the first time, Results: Eight compounds were isolated and identified as vanillicacid( 1), protocatechuic acid( 2),( +)-pinoresinol diglucoside( 3),( +)-pinoresinol-4’-O-β-D-glucopyranoside( 4),( +)-syringaresinol-4’-O-β-Dglucopyranoside( 5),7,9,9’-trihydroxy-3,3’-dimethoxy-8-O-4’-neolignan-4-O-β-D-glucopyranoside( 6),butyl-β-D-fructopyranoside( 7),butyl-β-D-fructofuranoside( 8). Compounds 2,8 showed strong cytotoxic activity. compounds 3,6 ~ 8 are isolated from Clematis genus for the first time, compounds 6 and 8 are isolated from Ranunculaceae family for the first time. Compounds 2,8 may be the effective components in Clematis aethusifolia.

Topics: Chromatography, High Pressure Liquid; Clematis; Drugs, Chinese Herbal; Furans; Humans; Lignans; Magnetic Resonance Spectroscopy; Medicine, Mongolian Traditional

A new 9,10-dihydrophenanthrene,1,5-dihydroxy-3,4,7-trimethoxy-9,10-dihydrophenanthrene (1) was isolated and identified from the whole plants of Dendrobium moniliforme, as well as 24 known compounds including hircinol (2), (2R*,3S*)-3-hydroxymethyl-9-methoxy-2-(4'-hydroxy-3',5'-dimethoxyphenyl)-2,3,6,7-tetrahydro-phenanthro[4,3-b]furan-5,11-diol (3), diospyrosin (4), aloifol I (5), moscatilin (6), 3,4'-dihydroxy-3',4,5-trimethoxybibenzyl (7), gigantol (8), 3,3'-dihydroxy-4,5-dimethoxybibenzyl (9), longicornuol A (10), N-trans-cinnamoyltyramine (11), paprazine (12), N-trans-feruloyl 3'-O-methyldopamine (13), moupinamide (14), dihydroconiferyl dihydro-p-coumarate (15), dihydrosinapyl dihydro-p-coumarate (16), 3-isopropyl-5-acetoxycyclohexene-2-one-1 (17), p-hydroxybenzaldehyde (18), vanillin (19), p-hydroxyphenylpropionic acid (20), vanillic acid (21), protocatechuic acid (22), (+)-syringaresinol (23), β-sitosterol (24) and daucosterol (25). Compounds 3, 4, 13, 16, 17 and 20 were isolated from the Dendrobium genus for the first time, and compounds 2, 5, 7, 9-12, 14, 15, 18, 21 and 22 were originally obtained from D. moniliforme.

Topics: Benzaldehydes; Bibenzyls; Cinnamates; Coumaric Acids; Dendrobium; Furans; Guaiacol; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Phenanthrenes; Phenylpropionates; Plants, Medicinal; Sitosterols; Spectrometry, Mass, Electrospray Ionization; Tyramine

Glycosides were isolated from the fruit of Camptotheca acuminata and identified using NMR, MS, UV and IR spectrometries. 10-O-(1-β-D-glycosyl) camptothecin (1) was identified for the first time in a natural material. In addition, compounds 2-4 were firstly reported from the fruits of C. acuminata and indentified as syringaresinol-4, 4'-O-bis-β-D-glucoside (2), hyperoside (3) and pumiloside (4), respectively. Two known compounds, vincoside-lactam (5) and strictosidinic acid (6), were also obtained.

Topics: Camptotheca; Camptothecin; Carbohydrates; Carbolines; Fruit; Furans; Glucosides; Glycosides; Hydrolysis; Lignans; Magnetic Resonance Spectroscopy; Quercetin; Spectrometry, Mass, Electrospray Ionization

Activation of peroxisome proliferator-activated receptors (PPARs) plays a crucial role in cellular energy metabolism that directly impacts mitochondrial biogenesis. In this study, we demonstrate that syringaresinol, a pharmacological lignan extracted from Panax ginseng berry, moderately binds to and activates PPARβ with KD and EC50 values of 27.62±15.76μM and 18.11±4.77μM, respectively. Subsequently, the expression of peroxisome proliferator-activated receptor γ coactivator-1α together with PPARβ transcriptional targets, mitochondrial carnitine palmitoyltransferase 1 and uncoupling protein 2, was also enhanced in terms of both mRNA and protein levels. The activation of these proteins induced mitochondrial biogenesis by enrichment of mitochondrial replication and density within C2C12 myotubes. Importantly, knockdown of PPARβ reduced the syringaresinol-induced protein expression followed by the significant reduction of mitochondrial biogenesis. Taken together, our results indicate that syringaresinol induces mitochondrial biogenesis by activating PPARβ pathway.

Topics: Animals; Carnitine O-Palmitoyltransferase; Cell Line; Furans; Gene Expression; Lignans; Mice; Mitochondria; Myoblasts; Panax; PPAR-beta; RNA Interference; RNA, Messenger; RNA, Small Interfering; Uncoupling Protein 2

Acid-catalyzed degradation of lignin in toluene containing methanol selectively yields C6-C2 lignin monomers and releases lignin oligomers, a potential raw feedstock for epoxy resins. We herein characterize the structures of the lignin oligomers by focusing on the changes in the interunit linkage types during solvolysis. The oligomeric lignin products were analyzed via thioacidolysis and 2D-HSQC-NMR. The results show that lignin oligomers ranging from monomers to tetramers are released through considerable cleavage of the β-O-4 linkages. The lignin oligomers from Cryptomeria japonica (softwood) mainly comprise β-5, β-1, and tetrahydrofuran β-β linkages, whereas Eucalyptus globulus (hardwood) yields oligomers rich in β-1 and syringaresinol β-β linkages. Both wood samples exhibit selective release of β-β dimers and a relative decrease in 5-5 and 4-O-5 bonds during solvolysis. The method presented for the separation of lignin oligomers without β-O-4 linkages and with linkages unique to each wood species will be useful for the production of lignin-based materials.

Topics: Cryptomeria; Eucalyptus; Furans; Gas Chromatography-Mass Spectrometry; Lignans; Lignin; Magnetic Resonance Spectroscopy; Molecular Structure; Wood

Topics: Aging; Animals; Area Under Curve; Bifidobacterium; CD3 Complex; Female; Forkhead Box Protein O3; Furans; Gastrointestinal Microbiome; Immunosenescence; Lactobacillus; Lignans; Male; Mice, Inbred C57BL; Mice, Inbred ICR; Rats, Sprague-Dawley; T-Lymphocyte Subsets; Verrucomicrobia

Hypoxia-inducible factor 1 (HIF-1) is a master regulator of hypoxic response and has been a prime therapeutic target for ischemia/reperfusion (I/R)-derived myocardial dysfunction and tissue damage. There is also increasing evidence that HIF-1 plays a central role in regulating aging, both through interactions with key longevity factors including Sirtuins and mTOR, as well as by directly promoting longevity in Caenorhabditis elegans.We investigated a novel function and the underlying mechanism of syringaresinol, a lignan compound, in modulation of HIF-1 and protection against cellular damage and death in a cardiomyocyte model of I/R injury. Syringaresinol caused destabilization of HIF-1α following H/R and then protected against hypoxia/reoxygenation (H/R)-induced cellular damage, apoptosis, and mitochondrial dysfunction in a dose-dependent manner. Knock-down of FOXO3 by specific siRNAs completely abolished the ability of syringaresinol to inhibit HIF-1 stabilization and apoptosis caused by H/R. Syringaresinol stimulated the nuclear localization and activity of FOXO3 leading to increased expression of antioxidant genes and decreased levels of reactive oxygen species (ROS) following H/R. Our results provide a new mechanistic insight into a functional role of syringaresinol against H/R-induced cardiomyocyte injury and death. The degradation of HIF-1α through activation of FOXO3 is a potential therapeutic strategy for ischemia-related diseases.

Topics: Animals; Antioxidants; Apoptosis; Caspase 3; Cell Death; Cell Hypoxia; Cell Line; Cell Survival; Flow Cytometry; Forkhead Box Protein O3; Forkhead Transcription Factors; Furans; Hypoxia-Inducible Factor 1, alpha Subunit; Lignans; Microscopy, Fluorescence; Mitochondria; Myocardium; Myocytes, Cardiac; Oxygen; Rats; Reactive Oxygen Species; Reperfusion Injury; RNA, Small Interfering; Up-Regulation

Syringaresinol exists either exclusively as one enantiomer or enantiomeric mixtures in plant foods. We found that (+)-syringaresinol, but not (-)-syringaresinol, upregulates silent information regulator two ortholog 1 (SIRT1) gene expression, and thus, Panax ginseng berry with predominantly high contents of (+)-syringaresinol exhibits higher activity in inducing SIRT1 gene expression than Acanthopanax senticosus Harms stem with almost equal proportion of the two enantiomers. These findings highlight the importance of the absolute configuration of syringaresinol for the biological activity.

Topics: Eleutherococcus; Forkhead Box Protein O3; Forkhead Transcription Factors; Fruit; Furans; Human Umbilical Vein Endothelial Cells; Humans; Lignans; Panax; Plant Extracts; Promoter Regions, Genetic; Real-Time Polymerase Chain Reaction; Reverse Transcriptase Polymerase Chain Reaction; RNA, Messenger; Sirtuin 1; Stereoisomerism; Surface Plasmon Resonance

A new γ-alkylated-γ-butyrolactone, named melongenolide A (1), along with nine known compounds were obtained from the roots of Solanum melongena, and their structures were identified as melongenolide A (1), (+)-syringaresinol (2), (+)-lyoniresinol (3), 5,5'-dimethoxy lariciresinol (4), (+)-(7R,8R)-4-hydroxy-3,3',5'-trimethoxy-8',9'-dinor-8,4'-oxyneoligna-7, 9-diol-7'-aldehyde (5), kaempferol-3-O-(2″,6″-di-O-p-trans-coumaroyl)-β-glucoside (6), arjunolic acid (7), vanillic acid (8), scoparone (9), and β-sitosterol (10). Compounds 2, 6, and 7 showed potent inhibitory effects on nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages, with IC50 values being 5.62 ± 0.86, 11.47 ± 0.98, and 27.75 ± 1.26 μmol·L(-1), respectively.

Topics: 4-Butyrolactone; Animals; Furans; Inflammation; Inhibitory Concentration 50; Kaempferols; Lignans; Macrophages; Mice; Nitric Oxide; Plant Extracts; Plant Roots; RAW 264.7 Cells; Solanum melongena; Triterpenes

To study the chemical components from the leaves of Fatsia japonica and their antitumor activities in vitro.. All compounds were separated and purified by column chromatography over silica gel, Sephadex LH-20 and preparative HPLC. Their structures were identified by physical and chemical properties and spectral methods including 1H-NMR and 13C-NMR. Antitumor assay was measured by MTT method.. 18 compounds were isolated and identified as palmitic acid (1), β-hydroxypropiovanillone (2), adenosine (3), β-sitosterol (4), daucosterol (5), oleanolic acid (6), echinocystic acid (7), betulinic acid (8), hederagenin(9), hederagenin-3-O-α-L-rhamnopyranosyl(1-->2)-α-L-arabinopyranoside(10), acacetin(11), quercetin(12), quercetin-3-O-β-D-glucopyranoside(13), isovitexin(14), isovitexin-7-O-glucoside(15), astragalin(16), methylpluviatolide(17), and syringaresinol-4-O-β-D-glucopyranoside(18).. All compounds are isolated from the leaves of Fatsia japonica for the first time except compound 1. The ethyl acetate extract and compounds 6, 10, 12 and 18 at the concentration of 0. 5 mg/mL showed inhibitory effect against the proliferation of colon cell line A549 with the inhibitory rate over 90% in vitro.

Topics: Antineoplastic Agents, Phytogenic; Araliaceae; Betulinic Acid; Cell Line, Tumor; Chromatography, High Pressure Liquid; Flavones; Furans; Glucosides; Humans; Kaempferols; Lactones; Lignans; Oleanolic Acid; Pentacyclic Triterpenes; Phytochemicals; Plant Leaves; Sitosterols; Triterpenes

To study the chemical constituents from root of Artocarpus styracifolius.. Tne constituents were isolated from the root of Artocarpus styracifolius by column chromatography over silica gel, RP-18 silica gel, MCI GEL CHP-20P, macroporous resin HP-20, Sephadex LH-20, Toyopearl HW-40C and by preparative HPLC. Their structures were elucidated by analysis of physical and chemical properties and spectral data.. Nine compounds were isolated and their structures were identified as p-hydroxy benzoic acid (1), syringic acid (2), 2,4-dihydroxy benzaldehyde (3), (+)-lyoniresinol (4), 5,5'-dimethoxysecoisolariciresinol (5), (+)- syringaresinol (6), scopoletin (7), xylarolide (8) and trans-oxyresveratrol (9).. Compounds 2, 5, 6 and 8 are isolated from Moraceae for the first time. Compounds 1, 4 and 7 are firstly characterized in the genus Artocarpus, compounds 3 and 9 are characterized in Artocarpus styracifolius for the first time.

Topics: Artocarpus; Chromatography, High Pressure Liquid; Furans; Gallic Acid; Lignans; Phytochemicals; Plant Extracts; Plant Roots; Scopoletin; Stilbenes

To study the chemical constituents from the stems and leaves in Drypetes hainanensis.. The constituents were isolated and purified by various chromatography, and the structures were identified by extensive spectral analysis.. Eleven compounds were isolated and identified as syringaresinol-4-O-glycoside (1), koaburaside (2), abietin (3) syringin (4), kelampayoside A (5), 7,7'-bis-(4-hydroxy-3,5-dimethoxyphenyl)-8,8'-dihydroxymethyl-tetrahydrofuran-4-O-β-glucopyranoside (6), amentoflavone (7), 3,4,5-trimethoxyphenyl-β-D-glucopyranoside (8),1,4-di-O-methyl-myo-inositol (9), glycerol (10) and succinic acid (11).. All the compounds are isolated from this plant for the first time.

Topics: Drugs, Chinese Herbal; Furans; Glucosides; Glycosides; Lignans; Magnoliopsida; Phenylpropionates; Phytochemicals; Plant Leaves; Plant Stems; Plants, Medicinal

To investigate the chemical constituents of Selaginella sinensis (Desv.) Spring.. Chromatographic separations on Diaion HP-20, silica gel, and Sephadex LH-20 were used. The structures of the isolates were elucidated on the basis of spectroscopic analysis, as well as chemical methods.. Eight compounds were obtained and their structures were identified as sinensioside A (1), syringaresinol-4- O-β-D-glucopyranoside (2), (+)-medioresinol-4-O-β-D-glucopyranoside (3), pinoresinol-4, 4'-di-O-β-D-glucopyranoside (4), quercetin (5), eucomic acid (6), shikimic acid (7), and 2, 3-dihydroamentoflavone (8).. Compound 1 is a new dihydrobenzofuran sesquilignan glycoside from Selaginella sinensis.

Topics: Benzofurans; Furans; Glucosides; Lignans; Molecular Structure; Plant Extracts; Plant Stems; Quercetin; Selaginellaceae

The Stewartia koreana Nakai (SK) had been used in oriental traditional medicine as a remedy for acute gastroenteritis, liver diseases, quadriplegia and pain. The antioxidant activity guided isolation 80% methyl extract from stems of SK yielded eight phenolic compounds. We evaluated the anti-oxidative and anti-inflammatory effects of these compounds via assays of 1,1-diphenyl-2-picrylhydazyl (DPPH) radicals and inhibition of nitric oxide (NO) production in lipopolysaccharide-stimulated RAW 264.7 macrophage cells. The results demonstrated that syringaresinol (6) exhibited significant DPPH radical-scavenging activity and inhibitory effects on NO production compared with its positive controls, ascorbic acid and L-NMMA, respectively.

Topics: Animals; Anti-Inflammatory Agents; Antioxidants; Ascorbic Acid; Biphenyl Compounds; Free Radical Scavengers; Furans; Lignans; Lipopolysaccharides; Macrophages; Mice; Molecular Structure; Nitric Oxide; omega-N-Methylarginine; Oxidation-Reduction; Phenols; Picrates; Plant Stems; Theaceae

To study the chemical constituents of Mallotus paniculatus.. Column chromatography were used for the isolation and purification. Spectroscopic methods including 1H-NMR, 13C-NMR and MS were used for the identification of structures.. Six compounds were isolated from the CHCl3 extract of 75% alcohol extract of the whole plant and identified to be quercetin( 1), kaempherol(2), hesperetin (3), 7,3'-O-dimethylluteolin (4), p-sitosterol (5) and syringaresinol (6).. All the compounds above were isolated from this plant for the first time.

Topics: Furans; Lignans; Mallotus Plant; Quercetin; Sitosterols

Increased SIRT1 expression exerts beneficial effects in transgenic animal models, ameliorating the onset and progression of aging-related disease phenotypes in various organs including the heart. The potential beneficial effects of SIRT1 have made SIRT1 a prime therapeutic target for age-related diseases and considerable efforts led to the identification of small molecule activator of SIRT1 protein. Thus far, however, a small molecule activator of SIRT1 gene expression has not been reported. Here, we report that syringaresinol, isolated from Panax ginseng berry pulp, is an activator of SIRT1 gene expression. Using human umbilical endothelial cells (HUVECs), we show that syringaresinol treatment induced binding of FOXO3 to the SIRT1 promoter in a sequence-specific manner, leading to induction of SIRT1 expression. Increased SIRT1 expression in HUVECs by syringaresinol treatment delayed cellular senescence and improved various markers of endothelial functions in a FOXO3 dependent manner. Collectively, these findings bring to light a new transcription activator of SIRT1 that may have therapeutic potential.

Topics: Cells, Cultured; Forkhead Box Protein O3; Forkhead Transcription Factors; Furans; Gene Expression Regulation; Human Umbilical Vein Endothelial Cells; Humans; Lignans; Promoter Regions, Genetic; Sirtuin 1

One alkyl glycoside, saussurostelloside A (1), two phenolic glycosides, saussurostellosides B1 (2) and B2 (3), and 27 known compounds, including eleven flavonoids, seven phenolics, six lignans, one neolignan, one phenethyl glucoside and one fatty acid, were isolated from an ethanol extract of Saussurea stella (Asteraceae). Their structures were elucidated by NMR, MS, UV, and IR spectroscopic analysis. Of the known compounds, (+)-medioresinol-di-O-β-D-glucoside (7), picraquassioside C (10), and diosmetin-3'-O-β-D-glucoside (27) were isolated from the Asteraceae family for the first time, while (+)-pinoresinol-di-O-β-D-glucoside (6), di-O-methylcrenatin (11), protocatechuic acid (14), 1,5-di-O-caffeoylquinic acid (17), formononetin (28), and phenethyl glucoside (29) were isolated from the Saussurea genus for the first time. The anti-inflammatory activities of three new compounds (1-3), five lignans ((-)-arctiin (4), (+)-pinoresinol-4-O-β-D-glucoside (5), (+)-pinoresinol-di-O-β-D-glucoside (6), (+)-medioresinol-di-O-β-D-glucoside (7) and (+)-syringaresinol-4-O-β-D-glucoside (8)), one neolignan (picraquassioside C (10)), and one phenolic glycoside (di-O-methylcrenatin (11)) were evaluated by testing their inhibition of the release of β-glucuronidase from PAF-stimulated neutrophils. Only compound 5 showed moderate inhibition of the release of β-glucuronidase, with an inhibition ratio of 39.1%.

Topics: Animals; Anti-Inflammatory Agents; Coumaric Acids; Disaccharides; Female; Flavonoids; Furans; Glucosides; Glucuronidase; Glycosides; Hydroxybenzoates; Inflammation; Isoflavones; Lignans; Male; Molecular Structure; Neutrophils; Phytotherapy; Plant Extracts; Platelet Activating Factor; Quinic Acid; Rats, Wistar; Saussurea

Higher intake of lignans, diphenolic plant compounds, may reduce the risk of certain types of cancer and cardiovascular diseases. We assessed the dietary intake of four lignans: matairesinol, secoisolariciresinol, lariciresinol and pinoresinol. Furthermore, for the breads we supplemented the data with two more lignans: syringaresinol and medioresinol. Study subjects were 172 men and 97 women aged 40-75 years, residing in Riga, the capital of Latvia, all living at home, eating habitual food. Median total lignan intake was 2259 (range 1169-5759) μg/day. Secoisolariciresinol contributed 58% and syringaresinol 22% of lignan intake. Bread was the major food source of lignans in men (86%), whereas in women it was bread (57%) and flaxseed (35%).

Topics: Adult; Aged; Bread; Butylene Glycols; Cardiovascular Diseases; Diet; Feeding Behavior; Female; Flax; Furans; Humans; Latvia; Lignans; Male; Middle Aged; Neoplasms; Phenols; Phytoestrogens; Plant Extracts; Sex Factors

Nitric oxide (NO) produced by endothelial NO synthase (eNOS) plays an important role in vascular functions, including vasorelaxation. We here investigated the pharmacological effect of the natural product syringaresinol on vascular relaxation and eNOS-mediated NO production as well as its underlying biochemical mechanism in endothelial cells. Treatment of aortic rings from wild type, but not eNOS(-/-) mice, with syringaresinol induced endothelium-dependent relaxation, which was abolished by addition of the NOS inhibitor N(G)-monomethyl-L-arginine. Treatment of human endothelial cells and mouse aortic rings with syringaresinol increased NO production, which was correlated with eNOS phosphorylation via the activation of Akt and AMP kinase (AMPK) as well as elevation of intracellular Ca(2+) levels. A phospholipase C (PLC) inhibitor blocked the increases in intracellular Ca(2+) levels, AMPK-dependent eNOS phosphorylation, and NO production, but not Akt activation, in syringaresinol- treated endothelial cells. Syringaresinol-induced AMPK activation was inhibited by co-treatment with PLC inhibitor, Ca(2+) chelator, calmodulin antagonist, and CaMKKβ siRNA. This compound also increased eNOS dimerization, which was inhibited by a PLC inhibitor and a Ca(2+)-chelator. The chemicals that inhibit eNOS phosphorylation and dimerization attenuated vasorelaxation and cGMP production. These results suggest that syringaresinol induces vasorelaxation by enhancing NO production in endothelial cells via two distinct mechanisms, phosphatidylinositol 3-kinase/Akt- and PLC/Ca(2+)/CaMKKβ-dependent eNOS phosphorylation and Ca(2+)-dependent eNOS dimerization.

Topics: Animals; Aorta; Enzyme Activation; Furans; Gene Deletion; Human Umbilical Vein Endothelial Cells; Humans; Lignans; Mice; Mice, Inbred C57BL; Nitric Oxide; Nitric Oxide Synthase Type III; Phosphatidylinositol 3-Kinases; Phosphoinositide Phospholipase C; Phosphorylation; Protein Multimerization; Proto-Oncogene Proteins c-akt; Vasodilation

To study the chemical constituents of the dichloromethane extracted from pine needles of Cedrus deodara.. Compounds were isolated and purified from the dichloromethane extract of pine needles by chromatography on silica gel and Sephadex LH-20. Their structures were identified on the basis of spectroscopic analysis and physicochemical property.. Nine compounds were isolated and purified. Their structures were identified as stigmasterol (1), oleanolic acid (2), parahydroxybenzaldehyde (3), beta-sitosterol (4), syringaresinol (5), daucosterol (6), p-hydroxybenzoic acid (7), gallicin (8) and gallic acid (9).. Compounds 1-3, 5 -9 are isolated from pine needles of this genus for the first time.

Topics: Cedrus; Furans; Lignans; Magnetic Resonance Spectroscopy; Methylene Chloride; Oleanolic Acid; Plant Extracts; Plant Leaves; Sitosterols; Solvents; Stigmasterol

A phytochemical investigation of Chromolaena odorata resulted in the isolation of five new compounds, 5aα,6,9,9aβ,10-pentahydro-10β-hydroxy-7-methylanthra[1,2-d][1,3]dioxol-5-one (1), 1,2-methylenedioxy-6-methylanthraquinone (2), 3-hydroxy-1,2,4-trimethoxy-6-methylanthraquinone (3), 3-hydroxy-1,2-dimethoxy-6-methylanthraquinone (4), and 7-methoxy-7-epi-medioresinol (5), together with 12 known compounds, odoratin (6), 3β-acetyloleanolic acid (7), ursolic acid (8), ombuin (9), 4,2'-dihydroxy-4',5',6'-trimethoxychalcone (10), (-)-pinoresinol (11), austrocortinin (12), tianshic acid (13), cleomiscosin D (14), (-)-medioresinol (15), (-)-syringaresinol (16), and cleomiscosin A (17). All the compounds were evaluated for their PPARγ transactivation activity, and compound 6 showed moderate activity with an EC(50) value of 3.10 μM.

Topics: Anthraquinones; Chromolaena; Dioxoles; Drugs, Chinese Herbal; Flavonoids; Furans; Hepatocytes; Humans; Lignans; Luciferases; Molecular Structure; PPAR gamma; Sesquiterpenes; Stereoisomerism

A novel flavone, named 4'-methoxy-3',5,7-trihydroxy-8-(1''-(3''',4''',5'''-trihydroxyphenyl)ethyl)flavone (1), was isolated from Sarcopyramis nepalensis, along with two known compounds syringaresinol (2) and aralidioside (3). Their structures were established by the spectroscopic analysis, especially by 2D NMR. All of the three compounds were isolated from the plant for the first time.

Topics: Flavones; Furans; Lignans; Melastomataceae; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular

To investigate the chemical constituents of Kalopanax septemlobus.. Chromatographic techniques including silica gel, gel, semi-preparative HPLC and PTLC as well as recrystallization were employed in the isolation and purification, and the structures were elucidated by spectral analysis and physical and chemical properties.. 6 compounds were identified as liriodendrin (1), (-) -syringarenol (2), trans-coniferyl aldehyde (3), trans-caffeic acid (4), beta-daucosterol (5), beta-sitosterol (6).. Compounds 2 -5 are obtained from this genus for the first time.

Topics: Acrolein; Aldehydes; Caffeic Acids; Furans; Kalopanax; Lignans; Molecular Structure; Plant Bark; Plant Roots; Plants, Medicinal; Sitosterols

To study the chemical constituents of the plant of Sarcandra glabra and provide reference for the study of the bioactive substances.. The compounds were isolated from the EtOH extract by various chromatographic methods and their structures were elucidated by their physico-chemical properties and the analysis of their spectral data.. Nine compounds were isolated and identified as isoscopletin (1), syringaresinol monoside (2), styraxjaponoside B (3), 5-O-caffeoylshikimic acid (4), shizukanolide E (5), isoastilbin (6), neoisoastilbin (7), astilbin (8), neoastilbin (9).. Compounds 1-7 were isolated from S. glabra for the first time.

Topics: Cholestenones; Drugs, Chinese Herbal; Flavonoids; Flavonols; Furans; Lignans; Magnoliopsida; Plant Bark; Plant Stems; Shikimic Acid

To investigate the chemical constituents of the flowers of Chrysanthemum indicum.. The chemical constituents were isolated by various column chromatographic methods. The structures were identified by spectral data.. Twelve compounds were isolated and identified as acacetin (1), tricin (2), 2',4'-dihydroxychalcone(3), 5-hydroxy-4',7-dimethoxyflavon(4),7hydroxyflavonone (5), isorhamnetin (6),5,6,7-trihydroxy- 3',4', 5'-trimethoxyflanon (7 ), quercetin (8) , (3 beta, 5 alpha, 6 beta, 7 beta, 14 beta)-eudesmen-3,5,6,11-tetrol (9), syringaresinol (10), liriodendrin (11), and genkwanin (12).. Compounds 3-7, 10-12 were isolated from this species for the first time, and compounds 3, 5, 7, 10, 11 were obtained from genus Chrysanthemum for the first time.

Topics: Chalcones; Chrysanthemum; Flavones; Flavonoids; Flavonols; Flowers; Furans; Glucosides; Lignans; Quercetin

A new triterpenoid, 3,4-seco-lupane-20(29)-ene-3,28-dioic acid, together with three known lignans, (-)-schisandrin B, (-)-sesamin and (-)-syringaresinol, was isolated from the pulp of Acanthopanax senticosus (Rupr. et Maxim) Harms. Their structures were elucidated by means of physicochemical properties and spectroscopic methods (1D, 2D-NMR and MS).

Topics: Cyclooctanes; Dioxoles; Eleutherococcus; Furans; Lignans; Molecular Structure; Plants, Medicinal; Polycyclic Compounds; Triterpenes

To study the chemical constituents from Solanum nigrum.. Compounds were isolated and purified by silica gel, Sephadex LH-20 and preparative HPLC. Their structures were identified by physicochemical properties and spectral analysis.. Six compounds were isolated and identified as (+)-pinoresinol (I), (+)-syringaresinol (II), (+)-medioresinol (III), scopoletin (IV), tetracosanoic acid (V) and beta-sitosterol (VI).. Compounds I - III are isolated from this genus for the first time, while compounds IV and V are isolated from this plant for the first time.

Topics: Anti-Inflammatory Agents; Chromatography, High Pressure Liquid; Fatty Acids; Furans; Lignans; Plants, Medicinal; Scopoletin; Sitosterols; Solanum nigrum

Leaves and wood of Peltostigma guatemalense, a novel species of the family Rutaceae, yielded a total of 14 secondary metabolites, i.e. methyl p-hydroxy benzoate, phenylacetic acid, beta-sitosterol, lupeol, syringaresinol, scopoletin, gardenin B (1), and seven alkaloids: gamma-fagarine (2), skimmianine (3), kokusaginine (4), 7-O-isopentenyl-gamma-fagarine (5), anhydro-evoxine (6), evoxine (7) and 4-methoxy-1-methyl-quinolin-2-one (8). The compounds have been identified by spectroscopic methods. Antibacterial and antimalarial in vitro activity of the isolated compounds were also determined. Methyl p-hydroxy benzoate and quinolone (8) were the most effective on Plasmodium falciparium strains.

Topics: Alkaloids; Animals; Anti-Bacterial Agents; Antimalarials; Bacteria; Furans; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Pentacyclic Triterpenes; Plant Extracts; Plasmodium falciparum; Quinolines; Rutaceae; Sitosterols; Triterpenes

Two new compounds, cinnamic aldehyde cyclic d-galactitol 3'R,4'S-acetal (1) and cinnamomumolide (2), along with six known compounds, syringaresinol (3), lyoniresinol (4), 5,7,3'-trimethoxyl-( - )-epicatechin (5), 5,7-dimethoxyl-3',4'-di-O-methylene-( +/- )-epicatechin (6), 2-methoxyl-4-hydroxy cinnamyl aldehyde (7), and glucosyringic acid (8), have been isolated from the dried tender stems of Cinnamomum cassia. Their structures were elucidated based on spectroscopic data. Compound 2 was elucidated as 8-methoxyl-9-hydroxy-3',4'-methylenedioxy-3S,4R-diphenyl butyrolactone, named cinnamomumolide, which exhibited activity in protecting against the injury caused by hydrogen peroxide oxidation on human umbilical vein endothelial cells, with an EC(50) value of 10.7 microM. Compounds 3-8 were isolated from the title plant for the first time.

Topics: 4-Butyrolactone; Anisoles; Cinnamates; Cinnamomum aromaticum; Drugs, Chinese Herbal; Endothelial Cells; Furans; Galactitol; Humans; Hydrogen Peroxide; Lignans; Molecular Structure; Naphthalenes; Oxidation-Reduction; Plant Stems; Umbilical Cord; Wounds and Injuries

To study the active constituents of Dendrobium aphyllum.. Various chromatographic techniques were used to isolate and purify the constituents, their physico-chemical properties and spectral data are determinated to elucidate the structure.. Eight compounds were isolated and identified as: 4'-methoxyl-tricin (1), tricin (2), 7, 3', 5'-tri-O-methyl-tricetin (3), syringic acid (4), ( + )-syring-aresinol (5), D-allitol (6), sucrose (7), icariside D2 (8).. Compounds 1-3, 6-8 were isolated from genus Dendrobium for the first time, additionally, the others were obtained firstly from the plant.

Topics: Dendrobium; Drugs, Chinese Herbal; Flavonoids; Furans; Gallic Acid; Glucosides; Lignans; Magnetic Resonance Spectroscopy; Plant Stems; Sucrose; Sugar Alcohols

To study the chemical constituents of the stems of Clematis parviloba.. The compounds were isolated and purified by repeated column chromatography with silica gel, Sephadex LH-20 and HPLC. Their structures were identified by spectroscopic data together with physical and chemical property.. Ten compounds have been isolated from the stems of C. parviloba, and identified as: (+) pinoresionol (1), (+) pinoresionol-4'-O-p-D-glucopyranoside (2), ( +) pinoresionol4, 4'-O-bis-beta-D-glucopyranoside (3), (-) syringaresinol (4), (+) syringaresinol-4'-O-beta-D-glucopyranoside (5), (-)episyringaresinol (6), (+) medioresinol-4'-O-beta-D-glucopyranoside (7), (+) lariciresinol-4-O-beta-D-glucopyranoside (8), (+) lariciresinol-4'-O-beta-D-glucopyranoside (9), (+) lariciresinol-4, 4'-O-bis-beta-D-glucopyranoside (10), respectively.. Compounds 6, 7 were isolated from this genus for the first time, and the other ones were isolated from this plant for the first time.

Topics: Chromatography, Gel; Chromatography, High Pressure Liquid; Clematis; Drugs, Chinese Herbal; Furans; Glucosides; Lignans; Magnetic Resonance Spectroscopy; Plant Stems; Spectrometry, Mass, Electrospray Ionization

We examined the effect of (-)-syringaresinol, a furofuran-type lignan isolated from Daphne genkwa, on cell cycle regulation in HL-60 human promyelocytic leukemia cells in vitro. (-)-Syringaresinol decreased the viability of HL-60 cells by inducing G(1) arrest followed by apoptosis in a dose- and time-dependent manner. The G(0)/G(1) phase of the cell cycle is regulated by cyclin-dependent kinases (Cdk), cyclins and cyclin-dependent kinase inhibitors (Cdki). We show by western blot analysis, that the (-)-syringaresinol-induced G(1) arrest was mediated through the increased expression of Cdki proteins (p21(cip1/waf1) and p27(kip1)) with a simultaneous decrease in cdk2, cdk4, cdk6, cyclin D(1), cyclin D(2), and cyclin E expression. The induction of apoptosis after treatment with (-)-syringaresinol for 24 h was demonstrated by morphological changes, DNA fragmentation, altered ratio of Bax/Bcl-2, cleavage of poly(ADP-ribose) polymerase and flow cytometry analysis. (-)-Syringaresinol also induced cytochrome c release and activation of caspase-3 and caspase-9. To our knowledge, this is the first time that (-)-syringaresinol has been reported to potently inhibit the proliferation of human promyelocytic HL-60 cells through G(1) arrest and induction of apoptosis. These findings suggest that (-)-syringaresinol may be a potential chemotherapeutic agent for the treatment of cancer.

Topics: Antineoplastic Agents; Apoptosis; Cell Proliferation; Cytochromes c; Furans; G1 Phase; HL-60 Cells; Humans; Lignans; Poly(ADP-ribose) Polymerases; Proto-Oncogene Proteins c-bcl-2

(-)-Syringaresinol and tricin, isolated from the AcOEt-soluble extract of the whole plants of Sasa borealis (Gramineae), showed inhibitory effects on the P-glycoprotein in adriamycin-resistant human breast cancer cells, MCF-7/ADR.

Topics: ATP Binding Cassette Transporter, Subfamily B, Member 1; Bambusa; Cell Line, Tumor; Chromatography, Thin Layer; Flavonoids; Furans; Humans; Lignans; Spectrum Analysis

Four new diepoxylignan glycosides, pinoresinol-4'-O-[6' '-O-(E)-feruloyl]-beta-D-glucopyranoside (1), pinoresinol-4'-O-[4' ',6' '-O-(E)-diferuloyl]-beta-D-glucopyranoside (2), pinoresinol-4'-O-[3' ',6' '-O-(E)-diferuloyl]-beta-D-glucopyranoside (3), and syringaresinol- 4'-O-[4' ',6' '-O-(E)-diferuloyl]-beta-D-glucopyranoside (4), together with three known compounds, pinoresinol (5), syringaresinol (6), and pinoresinol-4'-O-beta-D-glucopyranoside (7), were isolated from the n-butanol extract of Rhus javanica var. roxburghiana, and their structures were established using various spectroscopic techniques. Three glycosides (2-4) of the lignans showed moderate inhibition of multiplication of the tobacco mosaic virus.

Topics: Furans; Glycosides; Lignans; Plant Roots; Rhus; Tobacco Mosaic Virus; Virus Replication

A methanol extract from unripe Japanese apricot showed inhibitory activity of Helicobacter pylori motility. Inhibitory compound 1 was isolated and identified as (+)-syringaresinol (1) by spectoroscopic means. (+)-Syringaresinol (1) inhibited >90% of the H. pylori motility at a concentration of 500 microg/ml and the IC50 value was 50 microg/ml.

Topics: Furans; Helicobacter pylori; Lignans; Methanol; Prunus; Solvents; Spectrophotometry, Infrared; Spectroscopy, Fourier Transform Infrared

To investigate the chemical constituents of Dendrobium chrysotoxum.. The chemical constituents were isolated by various column chromatographic methods and structurally elucidated by spectral evidences.. Ten compounds were obtained and identified as (+)-syringare sinol (1), 5alpha, 8alpha-epidioxy-24( R)-methycholesta-6, 22-dien-3beta-ol (2), trans-3-(4-hydroxy-3-methoxyphenyl)-acrylic acid octacosyl ester (3), defusin (4), 3, 4-dihydroxy benzoic acid (5), 3, 4-dimethoxy-benzoic acid (6), vanillic acid (7), 3, 4-dimethoxy-benzoic acid methyl ester (8), 3, 5-dibromo-2-aminobenzaldehyde (9), heptadecanoic acid 2, 3-dihydroxy-propyl ester (10).. Compounds 1, 2 and 6-10 were isolated from this plant for the first time.

Topics: Dendrobium; Furans; Lignans; Plant Stems; Plants, Medicinal; Vanillic Acid

To study the chemical constituents from Serissa serissoides DC. roots.. Seven compounds were obtained from the 80% ethanol extract of Serissa serissoides roots by repeated column chromatography over silica gel, Sephadex LH-20 and Polyamide. Their structures were identified by analysis of their spectral data and physics character.. Seven compounds obtained from the plant leaves were identified as: (+)-pinoresinol(1), (-)-syringaresinol( 2), (+)-meduiresinol(3), (-)-olivil(4), beta-sitosterol(5), oleanolic acid(6) and daucosterol(7).. They are all known compounds. Compound 2 and 4 was obtained from this genus plants for the first time, and compounds 1,3 and 7 as known compounds were obtained from the root of the plant firstly.

Topics: Furans; Lignans; Molecular Structure; Oleanolic Acid; Plant Leaves; Plant Roots; Plants, Medicinal; Rubiaceae; Sitosterols

An organic extract prepared from Rinorea anguifera was investigated in order to identify the natural principle(s) responsible for stabilization of a topoisomerase I-DNA covalent binary complex. Bioassay-guided fractionation resulted in the isolation of mauritianin and (+)-syringaresinol as new topoisomerase I inhibitors, and also of the known inhibitor camptothecin.

Topics: Camptothecin; DNA; DNA Topoisomerases, Type I; Enzyme Inhibitors; Furans; Humans; Kaempferols; Lignans; Plant Extracts; Plants, Medicinal; Structure-Activity Relationship; Topoisomerase I Inhibitors

To study the chemical constituents from the whole plant of Dracocephalum moldavica.. The compounds were isolated by using column chromatography with RA polystyrene resin, polyamide and silica gel as packing materials, and the structures of the compounds were identified by means of spectral data.. eight compounds were identified as apigenin(I), luteolin(II), kaempferol(III), isorhamnetin(IV), tilianin(V), agastachoside(VI), acacetin-7-O-(6-O-Malonyl-beta-D-glucopyranoside) (VII) and syringaresinol(VIII).. Compounds I, II and III were isolated from genus Dracocephalum for the first time and compounds IV, VII and VIII were isolated from Dracocephalum moldavuca for the first time.

Topics: Apigenin; Chromatography, Thin Layer; Furans; Lamiaceae; Lignans; Luteolin; Plants, Medicinal

The aerial part of Leptadenia arborea has been shown to contain pinoresinol (1), syringaresinol (2), leucanthemitol (3) and E-ferulaldehyde (4). These known compounds are being reported for the first time from this plant. Among them, syringaresinol has shown an inhibitory effect against acetylcholinesterase. The IC(50) (the concentration of 50% enzyme inhibition) value of this compound was 200 microg/ml.

Topics: Acetylcholinesterase; Apocynaceae; Cholinesterase Inhibitors; Furans; Humans; Inhibitory Concentration 50; Lignans; Phytotherapy; Plant Components, Aerial; Plant Extracts

In the present study, liriodendrin isolated by activity-guided fractionation from the ethyl acetate (EtOAc) extracts of the stem bark of Acanthopanax senticosus, was evaluated for anti-inflammatory and antinociceptive activities. Liriodendrin (5, 10 mg/kg/day, p. o.) significantly inhibited the increase of vascular permeability induced by acetic acid in mice and reduced an acute paw edema induced by carrageenan in rats. When the analgesic activity was measured by the acetic acid-induced writhing test and hot plate test, liriodendrin showed a dose-dependent inhibition in animal models. In addition, syringaresinol, the hydrolysate of liriodendrin, more potently inhibited the LPS-induced production of NO, PGE 2 and TNF-alpha production of macrophages than liriodendrin. Consistent with these observations, the expression level of iNOS and COX-2 enzyme was decreased by syringaresinol in a concentration-dependent manner. These results suggest that the anti-inflammatory and antinociceptive effects of liriodendrin after oral administration were attributable to the in vivo transformation to syringaresinol, which may function as the active constituent.

Topics: Analgesics; Animals; Anti-Inflammatory Agents, Non-Steroidal; Chemical Fractionation; Cyclooxygenase 2; Dinoprostone; Eleutherococcus; Furans; Glucosides; Isoenzymes; Korea; Lignans; Lipopolysaccharides; Male; Mice; Mice, Inbred ICR; Nitric Oxide; Nitric Oxide Synthase; Nitric Oxide Synthase Type II; Pain Measurement; Plant Bark; Plant Stems; Prostaglandin-Endoperoxide Synthases; Rats; Rats, Sprague-Dawley; Tumor Necrosis Factor-alpha

Five compounds were isolated from the roots of Patrinia scabra Bunge separated and purified on sillica gel column chromatography. Their structures were elucidated on the physico-chemical properties and spectral data as lariciresinol(I), syringaresinol(II), scopoletin(III), quercetin(IV), ferulaic acid(V). All compounds were obtained from P. scabra for the first time. In vitro biological test of these compounds showed that syringaresinol was able to stimulate T and B lymphocyte proliferation.

Topics: B-Lymphocytes; Cell Division; Drugs, Chinese Herbal; Furans; Lignans; Patrinia; Plant Roots; Plants, Medicinal; Scopoletin; T-Lymphocytes

Syringaresinol isolated from Epimedium koreanum NAKA1 and Magnolia officinalis REHD. et WILS. was subjected to optical resolution by chiral HPLC to give (+)- and (-)-enantiomers. The two syringaresinol enantiomers, as well as a mixture of their glucosides, showed dose-dependent neuritogenesis in a concentration range from 0.24 to 24 microM in PC12h cells.

Topics: Animals; Chromatography, High Pressure Liquid; Epimedium; Furans; Humans; Lignans; Magnetic Resonance Spectroscopy; Magnolia; Nerve Regeneration; Neurites; Neurons; PC12 Cells; Rats; Spectrophotometry, Ultraviolet; Stereoisomerism

A new lignan named as hibiscuside, (+)-pinoresinol 4-O-[beta-glucopyranosyl (1--->2)-alpha-rhamnoside] (1), and a known lignan, syringaresinol (2) were isolated from the root bark of Hibiscus syriacus together with two feruloyltyramines (3,4) and three known isoflavonoids (5,6,7). The structures of these compounds have been established on the basis of their NMR, mass UV spectra. Among these phenolic compounds, 6"-O-acetyldaidzin (5), 6"-O-acetylgenistin (6), and 3-hydroxydaidzein (7) with IC(50) values of 8.2, 10.6, and 4.1 microM, respectively, significantly inhibited lipid peroxidation in rat liver microsomes. Hibiscuside (1), E- and Z-N-feruloyl tyramines (3,4) exhibited moderate antioxidant activity.

Topics: Animals; Antioxidants; Bridged Bicyclo Compounds, Heterocyclic; Disaccharides; Furans; Glycosides; In Vitro Techniques; Lignans; Lipid Peroxidation; Malvaceae; Microsomes, Liver; Rats

A trace monomeric compound was isolated from the aerial part of Siphonostegia chinensis, and determined by X-ray diffraction as a lignanoid compound named syringaresinol. It is obtained from this plant as well as from Scrophulariaceae for the first time.

Topics: Drugs, Chinese Herbal; Furans; Lignans; Molecular Conformation; X-Ray Diffraction

Topics: Animals; Antineoplastic Agents, Phytogenic; Furans; Leukemia P388; Lignans; Mice; Plants