Constituents of Chimaphila japonica and Their Diuretic Activity.

Three new phenols (1-3), one new cyclohexanol (4), two known phenols (5-6), and six known flavonoids (7-12) were isolated from the n-butanol of the 75% ethanol extract of all plants of Chimaphila japonica Miq. Among them, compound 5 was named and described in its entirety for the first time, and compounds 9 and 10 were reported in C. japonica for the first time. The structures of all compounds were confirmed using a comprehensive analysis of 1D and 2D NMR and HRESIMS data. Biological results show that compounds 4, 7, and 11 exhibited potent diuretic activity. The modes of interaction between the selected compounds and the target diuretic-related WNK1 kinase were investigated in a preliminary molecular docking study. These results provided insight into the chemodiversity and potential diuretic activities of metabolites in C. japonica.

Simultaneous analysis of natural and artificial sweeteners in sugar-free drinks and urine samples by column-switching UHPLC-charged aerosol detection method.

Sweeteners are considered an alternative to high-calorie foods or drinks and have been widely used globally. However, the simultaneous separation and detection of high-polarity natural and artificial sweeteners are challenging owing to their broad-spectrum physical and chemical properties. Herein, we developed a column-switching UHPLCCAD method and used it for detecting and quantitating 12 sweeteners, including natural sweeteners (erythritol, mannitol, xylitol, sorbitol and stevioside) and artificial sweeteners (acesulfame potassium, saccharin sodium salt, sodium cyclamate, sucralose, aspartame, alitame and neotame). The LOD and LOQ were 0.932-6.25 µg/mL and 3.10-20.83 µg/mL, respectively, and the method demonstrated excellent linearity (R² ≥ 0.9990), good precision (intraday and interday precision was 0.59-6.88 %), and high recovery (average recoveries were 85.16-108.64 %). This method was applied to determine the sweeteners in 15 sugar-free drinks purchased from the local Chinese supermarkets. What's more, natural sweetener erythritol and artificial sweetener acesulfame potassium were suspected over addition in sugar-free drinks. Meanwhile the method was applied to the sweeteners in various sugar-free drinks and the dynamic monitoring of transit and excretion in vivo after drinking. Those prove that the method can be used to the detection of sugar free drinks and quality control of the sweeteners. The study highlights the potential of UHPLC-charged aerosol detection technology in detection of multiple components in food industry.

Enhancement of growth in Ulva prolifera by diurnal temperature difference combined with nitrogen enrichment.

Many studies have documented the responses of Ulva prolifera to environmental factors. However, the diurnal temperature differences and interactive effects of eutrophication are usually ignored. In this study, we selected U. prolifera as material to examine the effects of diurnal temperature on growth, photosynthesis and primary metabolites under two nitrogen levels. We cultured U. prolifera seedlings under two temperature conditions (22-22 °C: 22 °C during day and night; 22-18 °C: 22 °C during day and 18 °C at night) and two nitrogen levels (LN: 0.1235 mg L-1; HN: and 0.6 mg L-1). The results showed that 1) HN-grown thalli had higher growth rates, the chlorophyll a (Chl a) content, photosynthesis, superoxide dismutase (SOD) activity, soluble sugar, and protein contents under the two temperature conditions; 2) The growth of thalli was enhanced by 22-18 °C condition compared with 22-22 °C, but the increase was only significant under HN condition; 3) 22-18°C-grown thalli had a lower net photosynthetic rate, maximal quantum yield (Fv/Fm), and dark respiration rate (Rd) than those grown at 22-22 °C; 4) No significant effects of diurnal temperature difference were detected on the SOD activity and soluble sugar content under LN and HN conditions, while the soluble protein content was enhanced by 22-18 °C under LN condition; 5) The nitrogen affected metabolite variations in U. prolifera more significantly than the diurnal temperature difference. The metabolite levels in the tricarboxylic acid cycle, amino acid, phospholipids, pyrimidine, and purine metabolism pathways increased under HN condition. The levels of glutamine, γ-aminobutyrate (GABA), 1-aminocyclopropane-1-carboxylate (ACC), glutamic acid, citrulline, glucose, sucrose, stachyose, and maltotriose were enhanced by 22-18 °C, especially under HN condition. These results identify the potential role of the diurnal temperature difference and offer new insight into the molecular mechanisms for U. prolifera responses to eutrophication and temperature.

Darkness and low nighttime temperature modulate the growth and photosynthetic performance of Ulva prolifera under lower salinity.

In order to understand how darkness/irradiance and low nighttime temperature might alter physiology of Ulva prolifera under lower salinity conditions, we analyzed the growth rates, water content, superoxide dismutase (SOD) activity, total soluble proteins (SPs) and carbohydrates content at the end of dark and light period under three temperature levels (25-25 °C treatment: 25 °C for day and night; 15-15 °C treatment: 15 °C for day and night; 25-15 °C treatment: 25 °C for day with 15 °C for night) and two salinity conditions (15, 25), meanwhile, the pigment content (chlorophyll a and b), chlorophyll fluorescence and photosynthetic oxygen evolution also were determined during light phase. We found that the U. prolifera showed higher growth rate and SOD activity during dark phase at 25 °C, but this dark-induced increase could not be observed at 15 °C. The reasons for this increase varied, however, maybe not included water content and SPs for no significant difference in water content observed under all the treatments, as well as lower SPs content for dark period aside that at 15 °C and salinity 15. Compared to other two temperature treatments, the thalli grown at 25-15 °C showed higher growth rate and the photosynthetic oxygen evolution rate in light phase under salinity 15 conditions, although the maximum relative electron transport rate (rETRmax) showed higher value under 25 °C treatment. These results indicate that the darkness and the lower nighttime temperature maybe responsible reason for the rapid growth of these green tide algae.

Salinity mediates the effects of nitrogen enrichment on the growth, photosynthesis, and biochemical composition of Ulva prolifera.

To study the combined effects of multiple nitrogen (N) sources and salinity on the growth and physiology on macroalgae, we cultured Ulva prolifera under three N levels (N0, 0.1235 mg L-1; N1, 0.6 mg L-1; and N2, 4.4 mg L-1; the ratios were 18:74:8 for NH4-N, NO3-N, and NO2-N, respectively) and three salinity conditions (15, 25, and 35). Then, the growth, pigment content, photosynthetic performance, superoxide dismutase (SOD) activity, and contents of soluble protein and carbohydrates were measured. The results showed the following: (1) Compared to that grown at salinity 25, the growth of U. prolifera decreased under salinity 35, especially under the N0 and N2 levels, but there were no significant effects of salinity 15 under any of the N levels. (2) There were no significant effects of salinity on the chlorophyll a (Chla) content, but compared to the content at salinity 25, the chlorophyll b (Chlb) content was enhanced by salinity 15 and 35; lower ratio values between Chla and carotenoids (Car) occurred under the salinity 25 treatment. Under each salinity condition, the pigments were enhanced by a high N level. (3) A relatively higher salinity level decreased the photosynthetic oxygen evolution rate, while a higher N level increased this value. Compared to the rate at salinity 25, the dark respiration rate (Rd) significantly increased at salinity 15 under the N0 condition. (4) SOD activity was enhanced by a high N level, but no significant effects of salinity were observed. (5) The carbohydrate content was enhanced at salinity 35 under the N0 and N1 levels, and under salinity 15, this value increased with increasing N levels. In conclusion, although the growth of U. prolifera decreased at high N levels under high salinity conditions, a high N level induced an increase in photosynthesis, while no significant decrease in growth occurred. These findings indicate that low salinity and high N levels may be nonnegligible reasons why this species thrives, and low salinity was the better choice when this species was used for wastewater treatment.

Photoperiod mediates the effects of elevated CO2 on the growth and physiological performance in the green tide alga Ulva prolifera.

Ulva spp., an increasingly important food, are the dominant species of the large-scale green tides. In this study, both the growth and the physiological responses of the Ulva prolifera were studied after cultured in three different light and dark regimes (12:12, 14:10 and 16:8-h light/dark) in combination with current (420 µatm; LC) and increased (1000 µatm; HC) levels of atmospheric CO2. Grown rate of U. prolifera was significantly enhanced by increased CO2 under the three light:dark regimes, especially under 16:8 h-light:dark, indicating that growth was C-unsaturated at present CO2 levels. U. prolifera showed a significantly higher growth rate and lower dark respiration rate (Rd) at 16:8 h-light:dark treatment than at 12:12 h-light/dark treatment, regardless of the CO2 treatment. The photochemical performance was largely unaffected by elevated CO2 and daylength. These results suggest that U. prolifera in a future CO2 enriched coastal water, seems to be resilient to higher CO2 concentrations, and this could be enhanced by longer daylength.

Two new conjugated ketonic fatty acids from the stem bark of Juglans mandshurica.

The present study was designed to isolate and characterize novel chemical constituents of the stem bark of Juglans mandshurica Maxim. (Juglandaceae). The chemical constituents were isolated and purified by various chromatographic techniques. The structures of the compounds were elucidated on the basis of spectral data (1D and 2D NMR, HR-ESI-MS, CD, UV, and IR) and by the comparisons of spectroscopic data with the reported values in the literatures. Two long chain polyunsaturated fatty acids (1 and 2) were obtained and identified as (S)-(8E,10E)-12-hydroxy-7-oxo-8,10-octadecadienoic acid (1) and (S)-(8E, 10E)-12-hydroxy-7-oxo-8,10-octadecadienoic acid methyl ester (2). To the best of our knowledge, this is the first report on the isolation and structural elucidation of the two new conjugated ketonic fatty acids from this genus.

Two new diarylheptanoids isolated from the roots of Juglans mandshurica.

Two new diarylheptanoids, ( - )-threo-3',4″-epoxy-1-(4-hydroxyphenyl)-7-(3-methoxyphenyl)heptan-2,3-diol (1) and (1α,3ß,5α,6α)-1,5-epoxy-3,6-dihydroxy-1,7-bis(3-methoxy-4-hydroxy-phenyl)-heptane (2), along with one known diarylheptanoid, rhoiptelol B (3), were isolated from the roots of Juglans mandshurica. The structures of compounds 1 and 2 were identified based on HR-ESI-MS, 1D and 2D NMR including (1)H-(1)H COSY, HMQC, HMBC and NOESY spectroscopic methods.

Chemical constituents from the aerial parts of Melandrium firmum.

Two new anthraquinones, melrubiellin C (1) and melrubiellin D (2), were isolated from the aerial parts of Melandrium firmum Rohrbach, together with eight known compounds (3-10). The structures of these compounds were elucidated using 1D and 2D NMR (COSY, HMQC, HMBC and NOESY) experiments. All isolated compounds were tested for their cytotoxicity against NCI-H460, Hep G2, MKN-28 and A-549 cells. Of these 10 compounds, 1 and 2 exhibited moderate cytotoxicity with IC50 values ranging from 9.54 to 32.41 µM.

A new chromene from the fruiting bodies of Chroogomphus rutilus.

A new chromene, acetic acid 2R-(4,8-dimethylnona-3,7-dienyl)-8-hydroxy-2-methyl-2H-chromen-6-yl ester (1), was isolated from the fruiting bodies of Chroogomphus rutilus, together with six known compounds (2-7). The structures of these compounds were identified based on 1D and 2D NMR, including (1)H-(1)H COSY, HMQC and HMBC spectroscopic methods. Of these seven compounds, 2 and 3 showed cytotoxicity against HSC-T6, SK-Hep1 and A549 cell lines.

Cytotoxic anthraquinone dimers from Melandrium firmum.

Two new anthraquinone dimers, melrubiellin A (1) and melrubiellin B (2), were isolated from the aerial part of Melandrium firmum Rohrbach, along with seven known compounds (3-9). The structures of these compounds were elucidated by spectral analyses, including 1D and 2D NMR (COSY, HMQC, HMBC and NOESY) experiments. Compound 1 and 2 exhibited significant cytotoxicity towards HeLa, NCI-H460, Hep G2, Hep 3B and MKN-28 cell lines with IC50 values ranging from 5.26 to 81.16 µM.

A new phenolic glycoside from Juglans mandshurica.

A new phenolic glycoside, 6-O-(4'-hydroxy-3',5'-dimethoxybenzoyl)-d-glucopyranose (4), and nine known compounds (1-3 and 5-10) were isolated from Juglans mandshurica Maxim. Compound structures were elucidated by NMR, HR-ESI-MS and acid hydrolysis. Compounds 5 and 6 are reported from this genus for the first time. Among compounds 1-10, only 1 exhibited cytotoxicity against MGC-803, A549, K562, JAR, HeLa, CaSKi and SiHa cell lines (IC50: 2.0, 5.3, 2.3, 6.9, 4.0, 6.6 and 2.7 µM, respectively).

(--)-Catechin glycosides from Ulmus davidiana.

Extensive chromatographic separation of the n-BuOH soluble fraction obtained from the stem and root barks of U. davidiana resulted in five hitherto unknown compounds together with a known one (-)-catechin 1. Structures of the five compounds were elucidated by chemical and spectroscopic analyses, to be (-)-catechin-7-O-gallate-5-O-(5″″-trans-caffeoyl)-ß-D-apiofuranoside-3-O-ß-D-apiofuranosyl-(1 → 2)-ß-D-glucopyranoside 2, (-)-catechin-7-O-gallate-5-O-(5″″-trans-caffeoyl)-ß-D-apiofuranoside-3-O-ß-D-glucopyranoside 3, (-)-catechin-7-O-gallate-5-O-ß-D-apiofuranoside-3-O-(2″-O-galloyl)-ß-D-glucopyranoside 4, (-)-catechin-7-O-gallate-5-O-(5″″-trans-caffeoyl)-ß-D-apiofuranoside 5, and (-)-catechin-7-O-gallate-5-O-(5″″-trans-feruloyl)-ß-D-apiofuranoside 6.

Anti-asthmatic effects of Angelica dahurica against ovalbumin-induced airway inflammation via upregulation of heme oxygenase-1.

Asthma is a chronic immune inflammatory disease characterized by variable airflow obstruction. The present study was undertaken to assess the effects of an Angelica dahurica Bentham et Hooker ethanolic extract (AD) on airway inflammation in an ovalbumin (OVA)-induced airway inflammation model. Mice that received AD displayed significantly lower airway eosinophilia, cytokine levels, including interleukin (IL)-4, IL-5, and tumor necrosis factor (TNF)-alpha levels, mucus production and immunoglobulin (Ig)E, compared with OVA-induced mice. In our experiments, AD treatment reduced airway inflammation and suppressed oxidative stress in the OVA-induced asthma model, partly via induction of heme oxygenase (HO)-1. The effects of AD on OVA-induced HO-1 induction were partially reversed by the HO-1 inhibitor, tin protoporphyrin (SnPP). Our results clearly indicate that AD is a suppressor of airway allergic inflammation, and may thus be effectively used as an anti-inflammatory drug in the treatment of asthma.

Epifriedelanol from the root bark of Ulmus davidiana inhibits cellular senescence in human primary cells.

Since cellular senescence involves organismal aging as well as diverse diseases, aging intervention might contribute to inhibit the aging process as well as aging-associated diseases. We tried to search for effective compounds from the root bark of ULMUS DAVIDIANA that are able to inhibit cellular senescence in human fibroblasts (HDFs) and human umbilical vein endothelial cells (HUVECs). Twenty-two compounds from the root bark of U. DAVIDIANA were isolated and screened for their inhibitory effects on adriamycin-induced cellular senescence by measuring senescence-associated ß-galatosidase (SA- ß-gal) activity. Among twenty-two compounds isolated, epifriedelanol (3), ssioriside (15), and catechin-7-O- ß-D-glucopyranoside (22) had inhibitory effects on adriamycin-induced cellular senescence in HDFs. Friedelin (2), epifriedelanol (3), and catechin-7-O- ß-apiofuranoside (18) were active in HUVECs. In particular, epifriedelanol (3) suppressed adriamycin-induced cellular senescence as well as replicative senescence in HDFs and HUVECs. These results suggest that epifriedelanol (3) reduces cellular senescence in human primary cells and might be used to develop dietary supplements or cosmetics that modulate tissue aging or aging-associated diseases.

Topoisomerase I and II inhibitory constituents from the bark of Tilia amurensis.

Two coumarins (1 and 6), one flavan-3-ol (2), one fatty acid (3), and two lignan glycosides (4 and 5) were isolated from the EtOAc and CH(2)Cl(2) extract of the bark of Tilia amurensis. Their chemical structures were identified by comparing their physicochemical and spectral data with those of published in literatures. Compounds 4, 5, and 6 were isolated from Tilia genus for the first time. Compounds 2 and 3 showed potent inhibitory activity against both DNA topoisomerase I (IC(50) values; 49 microM and 4 microM, respectively, with 18 microM of positive control compound, comptothecin) and DNA topoisomerase II (IC(50) values; 13 microM and 3 microM, respectively, with 50 microM of positive control compound, etoposide). However, all compounds did not showed cytotoxicity against the human colon adenocarcinoma cell line (HT-29), the human breast adenocarcinoma cell line (MCF-7), and human liver hepatoblastoma cell line (HepG-2).

Lignans from the roots of Saururus chinensis.

Four new lignans, saucerneol F (1), saucerneol G (2), saucerneol H (3), and saucerneol I (4), were isolated from the EtOAc extract of the roots of Saururus chinensis, together with one known compound, saucerneol D (5). The structures of compounds 1-4 were elucidated by spectroscopic analysis. These compounds showed cytotoxic activities against HT-29, MCF-7, and HepG-2 cell lines.

Inhibitory constituents against cyclooxygenases from Aralia cordata Thunb.

Seven diterpenes, four polyacetylenes, a lipid glycerol, and two sterols were isolated from the methylene chloride fraction of the root of Aralia cordata. Their chemical structures were determined as (-)-pimara-8(14),15-dien-19-oic acid (2), pimaric acid (3), (-)-kaur-16-en-19-oic acid (4), 17-hydroxy-ent-kaur-15-en-19-oic acid (9), 7alpha-hydroxy-(-)-pimara-8(14),15-dien-19-oic acid (10), 16alpha,17-dihydroxy-(-)-kauran-19-oic acid (11), 16-hydroxy-17-isovaleroyloxy-ent-kauran-19-oic acid (12), falcarindiol (5), dehydrofalcarindiol (6), dehydrofalcarindiol-8-acetate (7), falcarindiol-8-acetate (8), alpha-mono palmitin (13), stigmasterol (1), and daucosterol (14) by the spectral evidences. These compounds were tested with COX-1 and COX-2 inhibition assays. This study found that compounds 2, 4, 5, 6, 7, 8, and 10 inhibited COX-1 dependent conversion of the exogenous arachidonic acid to PGE2 in a dose-dependent manner with IC50 values of 134.2 microM, 121.6 microM, 170 microM, 50.4 microM, 11.7 microM, 99.6 microM, and 69.6 microM, respectively. But, most of these compounds weakly inhibited COX-2 dependent PGE2 generation. Among them, only compound 4 showed relatively significant inhibitory activity (IC50: 127.6 microM).