Phytochemical Constituents of Phyllanthus urinaria

Extensive column chromatography separation of the MeOH extract from the aerial parts of Phyllanthus urinaria afforded seventeen compounds (1 - 17). The structures of the compounds were elucidated by physicochemical and spectroscopic methods to be 5′-β-D-glucopyranosyloxyjasmonic butyl ester (1), (+)-cucurbic acid (2), dendranthemoside B (3), boscialin 4′-O-β-D-glucoside (4), 4,5-dihydroblumenol A (5), (6R,9R)-megastigman-4-ene-9,13-diol (6), (3S,5R,6S,9R)-3,6-dihydroxy-5,6-dihydro-β-ionol (7), (6S,9R)-roseoside (8), mallophenol B (9), icariside B 5 (10), corchoinoside B (11), canangaionoside (12), 5,6-epoxy-3-hydroxy-7-megastigmen-9-one (13), icariside B 2 (14), (7E)-2β,3β-dihydroxy-megastigm-7-en-9-one (15), betulalbuside A (16), and loliolide (17). The compounds 1, and 3 - 16 were isolated for the first time from this plant. The absolute stereochemistry of compound 1 was newly determined. The isolated compounds were tested for cytotoxic activity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay, but all the compounds showed weak cytotoxic activities.

Chemical Constituents of Impatiens balsamina Stems and Their Biological Activities

The purification of the MeOH extract from Impatiens balsamina by repeated column chromatography led to the isolation of one new tetrahydronaphthalene (1), together with eleven known compounds (2 – 12). The structure of the new compound (1) was determined by spectral data analysis (1H and 13C-NMR, 1H-1H COSY, HSQC, HMBC, NOESY, and HR-ESI-MS). Isolated compounds (1 – 12) were evaluated for their inhibitory effects on NO production in LPS-activated murine microglial BV-2 cells and their effects on NGF secretion from C6 glioma cells. Compounds 3, 7, and 10 reduced NO levels in LPS-activated murine microglial cells with IC50 values of 26.89, 25.59, and 44.21 µM, respectively. Compounds 1, 5, and 9 upregulated NGF secretion to 153.09 ± 4.66, 156.88 ± 8.86, and 157.34 ± 3.30%, respectively.

Phytochemical Constituents of Capsella bursa-pastoris and Their Anti-inflammatory Activity

Phytochemical investigation of 80% MeOH extract of the aerial parts of Capsella bursa-pastoris yielded fourteen compounds (1 – 14). The structures of the compounds were elucidated by spectroscopic methods to be methyl-1-thio-β-D-glucopyranosyl disulfide (1), 10-methylsulphinyl-decanenitrile (2), 11-methyl-sulphinyl-undecanenitrile (3), 1-O-(lauroyl)glycerol (4), phytene-1, 2-diol (5), (3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (6), loliolide (7), β-sitosterol (8), 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (9), 1-feruloyl-β-D-glucopyranoside (10), pinoresinol-4′-O-β-D-glucopyranoside (11), luteolin (12), quercetin-3-O-β-D-glucopyranoside (13), and luteolin 6-C-β-glucopyranoside (14). Although compound 1 was reported as synthetic compound, 1 was first isolated from natural source. NMR spectral data assignments of 1, 2 and 3 were reported for the first time, and compounds 1 – 14 were for the first time reported from this plant source. The anti-inflammatory effects of 1 – 14 were evaluated in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells. Compounds 12 exhibited strong inhibitory effects on nitric oxide production in LPS-activated BV-2 cells with IC50 values of 9.70 µM.

A New Steroidal Glycoside from Allium macrostemon Bunge

A phytochemical investigation of Allium macrostemon Bunge (Liliaceae) afforded the new pregnane steroidal glycoside, named allimacroside F (1), along with three known glycosides, benzyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (2), phenylethyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (3), (Z)-3-hexenyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (4). The identification and structural elucidation of a new compound (1) was carried out based on spectral data analyses (¹H-NMR, ¹³C-NMR, ¹H-¹H COSY, HSQC, HMBC, and NOESY) and HR-FAB-MS.

A New Neolignan Derivative, Balanophonin Isolated from Firmiana simplex Delays the Progress of Neuronal Cell Death by Inhibiting Microglial Activation

Excessive activation of microglia causes the continuous production of neurotoxic mediators, which further causes neuron degeneration. Therefore, inhibition of microglial activation is a possible target for the treatment of neurodegenerative disorders. Balanophonin, a natural neolignoid from Firmiana simplex, has been reported to have anti-inflammatory and anti-cancer effects. In this study, we aimed to evaluate the anti-neuroinflammatory effects and mechanism of balanophonin in lipopolysaccharide (LPS)-stimulated BV2 microglia cells. BV2 microglia cells were stimulated with LPS in the presence or absence of balanophonin. The results indicated that balanophonin reduced not only the LPS-mediated TLR4 activation but also the production of inflammatory mediators, such as nitric oxide (NO), prostaglandin E2 (PGE2), Interleukin-1β (IL-1β), and tumor necrosis factor-α (TNF-α), in BV2 cells. Balanophonin also inhibited LPS-induced inducible nitric oxide synthase (iNOS), and cyclooxygenase-2 (COX2) protein expression and mitogen activated protein kinases (MAPKs), including extracellular signal-regulated kinase (ERK1/2), c-Jun N-terminal kinase (JNK), and p38 MAPK. Interestingly, it also inhibited neuronal cell death resulting from LPS-activated microglia by regulating cleaved caspase-3 and poly ADP ribose polymerase (PARP) cleavage in N2a cells. In conclusion, our data indicated that balanophonin may delay the progression of neuronal cell death by inhibiting microglial activation.

Effects of Caffeic Acid, Myristicin and Rosemarinic Acid on the Gene Expression and Production of Airway MUC5AC Mucin

Perilla frutescens was empirically used for controlling airway inflammatory diseases in folk medicine. We investigated whether caffeic acid, myristicin and rosemarinic acid derived from Perilla frutescens significantly affect the gene expression and production of mucin from airway epithelial cells. Confluent NCI-H292 cells were pretreated with caffeic acid, myristicin or rosemarinic acid for 30 min and then stimulated with phorbol 12-myristate 13-acetate (PMA) for 24 h. The MUC5AC mucin gene expression and production were measured by reverse transcription - polymerase chain reaction (RT-PCR) and enzyme-linked immunosorbent assay (ELISA), respectively. Additionally, we examined whether caffeic acid, myristicin or rosemarinic acid affects MUC5AC mucin production indued by epidermal growth factor (EGF) and tumor necrosis factor-α (TNF-α), the other two stimulators of production of airway mucin. The results were as follows: (1) Caffeic acid, myristicin and rosemarinic acid inhibited the gene expression and production of MUC5AC mucin induced by PMA from NCI-H292 cells, respectively; (2) Among the three compounds derived from Perilla frutescens, only rosemarinic acid inhibited the production of MUC5AC mucin induced by EGF or TNF-α, the other two stimulators of production of airway mucin. These results suggest that rosemarinic acid derived from Perilla frutescens can regulate the production and gene expression of mucin, by directly acting on airway epithelial cells and, at least in part, explains the traditional use of Perilla frutescens as remedies for diverse inflammatory pulmonary diseases.

Phenolic Compounds from the Leaves of Stewartia pseudocamellia Maxim. and their Whitening Activities

The half-dried leaves of Stewartia. pseudocamellia were extracted with hot water (SPE) and partitioned with n-hexane (SPEH), dichloromethane (SPED), and ethyl acetate (SPEE) successively. SPE and SPEE showed significant inhibitory effects against melanogenesis and tyrosinase activities. By bioassay-guided isolation, ten phenolic compounds were isolated by column chromatography from SPEE. The whitening effect of the isolated compounds from SPEE were tested for the inhibitory activities against melanogenesis using B16 melanoma cells, in vitro inhibition of tyrosinase, and L-3,4-dihydorxy-indole-2-carboxylic acid (L-DOPA) auto-oxidation assay. A cytotoxic activity assay was done to examine the cellular toxicity in Raw 264.7 macrophage cells. Of the compounds isolated, gallic acid and quercetin revealed significant inhibitory activities against melanogenesis compared to arbutin. In particular, quercetin exhibited similar inhibitory activities against tyrosinase and L-DOPA oxidation without cytotoxicity. These results suggested that SPE could be used as a potential source of natural skin-whitening material in cosmetics as well as in food products.

Expectorant and Antitussive Effect of Hedera helix and Rhizoma coptidis Extracts Mixture

PURPOSE: This study aims to investigate the additive effect of the Hedera helix (HH) and Rhizoma coptidis (RC) extracts mixture on antitussive and expectorant activities in animals. MATERIALS AND METHODS: The expectorant assay was performed with phenol red secretion in mice trachea. Mice or guinea pigs were randomly divided into groups of 8 each, including negative and positive control groups. After gastric administration of the test extracts in mice, 2.5% phenol red solution (0.2 mL) was intraperitoneally injected. Trachea was dissected and optical density of tracheal secretion was measured. After gastric administration of the test extracts in guinea pigs, the antitussive activities were assessed using a citric acid-induced cough measurement. RESULTS: The extracts of HH and RC significantly increased tracheal secretion and inhibited cough. The mixture of HH and RC extracts in a 1:1 concentration at a dose of 200 mg/kg showed a more potent effect on phenol red secretion (25.25+/-3.14) and cough inhibition (61.25+/-5.36) than the individual use of each extracts [phenol red secretion; HH 13.39+/-4.22 (p=0.000), RC 20.78+/-2.50 (p=0.010), cough inhibition; HH 9.89+/-4.14 (p=0.010), RC 30.25+/-7.69 (p=0.000)]. A 3:1 ratio mixture of HH to RC demonstrated an optimal expectorant effect (p<0.001), and this mixture showed expectorant and antitussive effects in a dose-dependent manner. CONCLUSION: This study provides evidence for antitussive and expectorant effect of a 3:1 mixture of HH and RC, which may be a useful therapeutic option for respiratory diseases.

Inhibition of Proinflammatory Cytokine Generation in Lung Inflammation by the Leaves of Perilla frutescens and Its Constituents

This study was designed to find some potential natural products and/or constituents inhibiting proinflammatory cytokine generation in lung inflammation, since cytokines such as tumor necrosis factor-alpha (TNF-alpha) and interleukin-6 (IL-6) are pivotal for provoking airway inflammation. In our preliminary screening procedure, the 70% ethanol extract of the leaves of Perilla frutescens (PFE) was found to clearly inhibit TNF-alpha production in the lung at 100 mg/kg, after intranasal lipopolysaccharide treatment of mice. Based on this result, ten constituents including phenylpropanoids (allyltetramethoxybenzene, caffeic acid, dillapiole, elemicin, myristicin, nothoapiole, rosmarinic acid methyl ester, rosmarinic acid) and monoterpenes (perilla aldehyde and perilla ketone) were successfully isolated from the extract. Among them, elemicin and myristicin were found for the first time to concentration-dependently inhibit IL-1beta-treated IL-6 production from lung alveolar epithelial cells (A549) at concentrations of 10-100 microM. These findings suggest that the phenylpropanoids including elemicin and myristicin have the potential to be new inhibitory agents against lung inflammation and they may contribute, at least in part, to the inhibitory activity of PFE on the lung inflammatory response.

Inhibition of Proinflammatory Cytokine Generation in Lung Inflammation by the Leaves of Perilla frutescens and Its Constituents

This study was designed to find some potential natural products and/or constituents inhibiting proinflammatory cytokine generation in lung inflammation, since cytokines such as tumor necrosis factor-alpha (TNF-alpha) and interleukin-6 (IL-6) are pivotal for provoking airway inflammation. In our preliminary screening procedure, the 70% ethanol extract of the leaves of Perilla frutescens (PFE) was found to clearly inhibit TNF-alpha production in the lung at 100 mg/kg, after intranasal lipopolysaccharide treatment of mice. Based on this result, ten constituents including phenylpropanoids (allyltetramethoxybenzene, caffeic acid, dillapiole, elemicin, myristicin, nothoapiole, rosmarinic acid methyl ester, rosmarinic acid) and monoterpenes (perilla aldehyde and perilla ketone) were successfully isolated from the extract. Among them, elemicin and myristicin were found for the first time to concentration-dependently inhibit IL-1beta-treated IL-6 production from lung alveolar epithelial cells (A549) at concentrations of 10-100 microM. These findings suggest that the phenylpropanoids including elemicin and myristicin have the potential to be new inhibitory agents against lung inflammation and they may contribute, at least in part, to the inhibitory activity of PFE on the lung inflammatory response.