Structure-diversified terpenoids from Salvia prattii and their protective activity against alcoholic liver diseases.

Eleven previously unreported compounds (1-11), including five diterpenoids (1-5) and six sesquiterpenoids (6-11), together with two known diterpenoids (12-13), have been isolated from the roots of Salvia prattii. Their structures were comprehensively elucidated through spectroscopic methods, and their configurations were established using computational 13C nuclear magnetic resonance and electronic circular dichroism. Compound 1 was found to be an abietane-type diterpenoid with a novel rearrangement generated from the cleavage of the C-4/5 chemical bond, 20-methyl shift, and the rearrangement of the C-10 side chain. Compounds 2-3 were the third and fourth examples of arrangement seco-norabietanes with a spiro-lactone ring. We evaluated all compounds for their protective effects against alcoholic liver diseases (ALD). Compound 2 exhibited potential protective activity and hence can be used as a novel anti-ALD candidate.

Isolation of Two New Phenolic Glycosides from Castanopsis chinensis Hance by Combined Multistep CC and HSCCC Separation and Evaluation of Their Antioxidant Activity.

The characteristics of high polarity and susceptibility to oxidation in phenolic glycosides increase the difficulty of their separation from natural products. In the present study, two new phenolic glycosides with similar structures were isolated from Castanopsis chinensis Hance using a combination of multistep CC and high-speed countercurrent chromatography. Preliminary separation of the target fractions was carried out by Sephadex LH-20 chromatography (100-0% EtOH in H2O). High-speed countercurrent chromatography with an optimized solvent system of N-Hexane/Ethyl acetate/Methanol/Water (1:6:3:4, v/v/v/v) with a satisfactory stationary phase retention and separation factor was used for further separation and purification of the phenolic glycosides. Consequently, two new phenolic glycoside compounds were obtained with purities of 93.0% and 95.7%. 1D-NMR and 2D-NMR spectroscopy, mass spectrometry, and optical rotation were employed to identify their structures, which were assigned as chinensin D and chinensin E. The antioxidant and α-glucosidase inhibitory activities of these two compounds were evaluated using a DPPH antioxidant assay and a α-glucosidase inhibitory assay. Both compounds showed good antioxidant activity with IC50 values of 54.5 ± 0.82 µg/mL and 52.5 ± 0.47 µg/mL. The α-glucosidase inhibitory activity of the compounds was poor. The successful isolation and structure identification of the two new compounds provides materials not only for a systematic isolation method of phenolic glycosides with similar structures, but also for the screening of antioxidants and enzyme inhibitors.

The complete chloroplast genome sequence of Castanopsis fordii Hance (Fagaceae).

Castanopsis fordii Hance 1884 is a typical evergreen broad-leaved forest plant in the south subtropical and middle subtropical regions of China. It has high utilization value in wood production and soil erosion protection. Here, we first reported and characterized the complete chloroplast (cp) genome sequence of C. fordii based on Illumina paired-end sequencing data. The complete cp genome sequence of C. fordii was 160,853 base pairs (bp) in length which contained two inverted repeats (IRs) of 25,699 bp separated by a large single-copy (LSC) and a small single copy (SSC) of 90,474 bp and 18,981 bp, respectively. The cpDNA contained 129 genes, comprising 85 protein-coding genes, 36 tRNA genes, 8 rRNA genes. The overall GC content of the plastome was 36.8%. Phylogenetic analysis base on 14 chloroplast genomes indicated that C. fordii was closely related to the species C. tibetana and C. concinna in Fagaceae.

Two new isoflavones from the barks of Dalbergia hancei Benth.

Two new isoflavone compounds, Dalhancei A (1) and Dalhancei B (2), along with a known compound epicatechin (3) were isolated from 80% methanol extract of the barks of Dalbergia hancei Benth. The structures of compounds 1-3 were elucidated by comparison with the literature and physical data analysis, including optical rotation, MS, 1D and 2D NMR spectra. Compounds 1 and 2 showed weak inhibitory activity against tyrosinase at 16.22 mmol/L, with inhibition rates of 42.23 ± 0.18% and 45.68 ± 0.17%, respectively; compound 1 exhibited weak inhibitory activity against α-glucosidase with the inhibition rate of 43.72 ± 0.22% at 5.41 mmol/L, compounds 2 and 3 had better α-glucosidase inhibitory activity than compound 1 with IC50 values of 0.90 ± 0.18 and 0.41 ± 0.17 mmol/L, respectively.

Two truxinate derivatives and a phenyldilactone from the leaves of Castanopsis eyrei.

Phytochemical investigation of the Leaves of Castanopsis eyrei led to the isolation of two new natural truxinate derivatives and a new phenyldilactone. The structures of the new natural compounds were determined by spectroscopic methods and chemical evidence as 3,3',4,4'-tetrahydroxy-ß-truxillic acid (1), 3,3',4,4'-tetrahydroxy-δ-truxillic acid (2), 3'-hydroxymaysedilactone A (3). Establishment of a Caenorhabditis elegans lipid metabolism model using GFP and mCherry fluorescently labeled lipid droplets to screen compound 3 for its activity in reducing lipid accumulation.

Triterpene hexahydroxydiphenoyl ester and phenol glucosides from the leaves of Castanopsis eyrie (Champ. ex Benth.) Hutch.

As a part of our systematic study on Castanopsis genus (Fagaceae), one new triterpene hydrolysable tannin (1) and two new phenol glucosides (2 and 3) were isolated from the leaves of Castanopsis eyrei (Champ. ex Benth.) Hutch. Compound 1 was identified as a triterpene hexahydroxydiphenoyl (HHDP) ester. This type of compounds has only been isolated from Castanopsis genus. The structures of 1-3 were elucidated by the combination of spectroscopic analysis (MS, 1 D and 2 D NMR) and chemical evidence.

Structural Characterization and Assessment of Anti-Inflammatory Activities of Polyphenols and Depsidone Derivatives from Melastoma malabathricum subsp. normale.

The roots of Melastoma malabathricum subsp. normale (D. Don) Karst. Mey have been used in traditional ethnic medicine systems in China to treat inflammation-triggered ailments, such as trauma, toothache, and fever. Therefore, the aim of this study is to screen for compounds with anti-inflammatory activity in the title plant. The extract of M. malabathricum subsp. normale roots was separated using various chromatographic methods, such as silica gel, ODS C18, MCI gel, and Sephadex LH-20 column chromatography, as well as semi-preparative HPLC. One new complex tannin, named whiskey tannin D (1), and an undescribed tetracyclic depsidone derivative, named guanxidone B (2), along with nine known polyphenols (2-10) and three known depsidone derivatives (12-14) were obtained from this plant. The structures of all compounds were elucidated by extensive NMR and CD experiments in conjunction with HR-ESI-MS data. All these compounds were isolated from this plant for the first time. Moreover, compounds 1-4, 8, and 10-14 were obtained for the first time from the genus Melastoma, and compounds 1, 2, and 11-14 have not been reported from the family Melastomataceae. This is the first report of complex tannin and depsidone derivatives from M. malabathricum subsp. normale, indicating their chemotaxonomic significance to this plant. Compounds 1-12 were investigated for their anti-inflammatory activities on the production of the nitric oxide (NO) in lipopolysaccharide (LPS)-stimulated RAW264.7 cells, and compounds 1, 11, and 12 showed anti-inflammatory activities with IC50 values of 6.46 ± 0.23 µM, 8.02 ± 0.35 µM, and 9.82 ± 0.43 µM, respectively. The structure-activity relationship showed that the catechin at glucose C-1 in ellagitannin was the key to its anti-inflammatory activity, while CH3O- at C-16 of aromatic ring A in depsidone derivatives had little effect on its anti-inflammatory activity. The study of structure-activity relationships is helpful to quickly discover new anti-inflammatory drugs. The successful isolation and structure identification of these compounds, especially complex tannin 1, not only provide materials for the screening of anti-inflammatory compounds, but also provide a basis for the study of chemical taxonomy of the genus Melastoma.

Life cycle assessment of heavy metal contaminated sites: phytoremediation and soil excavation.

Phytoextraction by native Taiwanese chenopod (Chenopodium formosanum Koidz.) and Napier grass (Pennisetum purpureum) for heavy metals such as chromium (Cr), nickel (Ni), and copper (Cu) was reported first. Maximum bioconcentration factors of Cu and Cr were 8.8 and 12.5 by Taiwanese chenopod. Napier grass cultivar Taishi No.4 plants demonstrated higher survivals than that of Taiwanese chenopod, under heavy metal stress in soils. All heavy metal accumulation and biomass data were employed, as well as historical engineering data were collected for conventional excavation-and-refill remediation of two sites. Life cycle assessment (LCA) was conducted for comparing environmental performances of phytoextraction and conventional remediation for two contaminated sites. Assuming one-year growth, three harvests were done and biomass was collected and sent to the nearest municipal incinerators, phytoextraction by both plants demonstrated superior environmental performances than conventional methods for contaminated site remediation. High quantities of fuels to haul the soils of conventional methods mainly contributed to the greenhouse gas emission. Phytoextraction has the most advantages for sites with lesser extents of pollution and time restraints. Environmental performances of phytoremediation were even better if energy recovered from biomass incineration is counted. Novelty statement Phytoextraction by native Taiwanese chenopod and Napier grass was firstly reported. Life cycle assessment was conducted for comparing the phytoextraction and conventional remediation. Phytoextraction demonstrated superior environmental performances. Energy reutilization of biomass recovered made phytoremediation more sustainable.

Structural Characterization and Assessment of Anti-Inflammatory and Anti-Tyrosinase Activities of Polyphenols from Melastoma normale.

Polyphenols, widely distributed in the genus Melastoma plants, possess extensive cellular protective effects such as anti-inflammatory, anti-tyrosinase, and anti-obesity, which makes it a potential anti-inflammatory drug or enzyme inhibitor. Therefore, the aim of this study is to screen for the anti-inflammatory and enzyme inhibitory activities of compounds from title plant. Using silica gel, MCI, ODS C18, and Sephadex LH-20 column chromatography, as well as semipreparative HPLC, the extract of Melastoma normale roots was separated. Four new ellagitannins, Whiskey tannin C (1), 1-O-(4-methoxygalloyl)-6-O-galloyl-2,3-O-(S)-hexahydroxydiphenoyl-ß-d-glucose (2), 1-O-galloyl-6-O-(3-methoxygalloyl)-2,3-O-(S)-hexahydroxydiphenoyl-ß-d-glucose (3), and 1-O-galloyl-6-O-vanilloyl-2,3-O-(S)-hexahydroxydiphenoyl-ß-d-glucose (4), along with eight known polyphenols were firstly obtained from this plant. The structures of all isolates were elucidated by HRMS, NMR, and CD analyses. Using lipopolysaccharide (LPS)-stimulated RAW2 64.7 cells, we investigated the anti-inflammatory activities of compounds 1-4, unfortunately, none of them exhibit inhibit nitric oxide (NO) production, their IC50 values are all > 50 µM. Anti-tyrosinase activity assays was done by tyrosinase inhibition activity screening model. Compound 1 showed weak tyrosinase inhibitory activity with IC50 values of 426.02 ± 11.31 µM. Compounds 2-4 displayed moderate tyrosinase inhibitory activities with IC50 values in the range of 124.74 ± 3.12-241.41 ± 6.23 µM. The structure-activity relationships indicate that hydroxylation at C-3', C-4', and C-3 in the flavones were key to their anti-tyrosinase activities. The successful isolation and structure identification of ellagitannin provide materials for the screening of anti-inflammatory drugs and enzyme inhibitors, and also contribute to the development and utilization of M. normale.

Enhancement of phytoextraction by Taiwanese chenopod and Napier grass by soapnut saponin and EDDS additions.

Employment of biosurfactants and biodegradable chelants could further promote sustainability of soil and groundwater remediation tasks. Biosurfactant (soapnut saponin) and biodegrading chelants (ethylenediamine-N,N'-disuccinic acid (EDDS)) were employed to enhance the phytoextraction by native Taiwanese chenopod (Chenopodium formosanum Koidz.), Napier grass (Pennisetum purpureum) cultivar Taishi No. 4, and soapwort (Saponaria officinalis). Ethylene diamine tetraacetic acid (EDTA) was also employed as the control. Contaminated soils as silty clay loam texture was collected from a defunct rice paddy, containing chromium (Cr), cadium (Cd), and copper (Cu). Addition of both soapnut saponin and EDDS proportionally increased bioaccumulation factors (BCFs) of aboveground biomass for all three plants. Taiwanese chenopod demonstrated the best BCF values among three plants, with BCF increased from 0.76 to 2.6 and 1.3 for Cu under the presence of the highest dosages of EDDS and saponin. Plant aboveground biomass did exhibit negative correlation toward biomass metal concentrations. Presence of saponin did exhibit the least negative slopes among the correlations of all three additives for three plants. Taiwanese chenopod did exhibit the least negative slopes among the correlations of all three additives for three plants. Above observations suggested that saponin may have some protection for plants, especially for Napier grass. Taiwanese chenopod could possess more tolerance toward heavy metals than Napier grass does.

Bioethanol production from recovered napier grass with heavy metals.

Using plants to absorb and accumulate heavy metals from polluted soil, followed by the recycling of explants containing heavy metals, can help achieve the goal of reverting contaminated soil to low heavy-metal content soil. However, the re-use of recovered explants can also be problematic. Meanwhile, bioethanol has become a popular energy source. In this study, napier grass was used for the remediation of soil contaminated with heavy metals (artificially contaminated soil). The influence of bioethanol production from napier grass after phytoremediation was also investigated. The concentration of Zn, Cd, and Cr in the contaminated soil was 1000, 100, and 250 mg/kg, respectively. After napier grass phytoremediation, the concentration (dry biomass) of Zn, Cd, and Cr in the explants was 2701.97 ± 173.49, 6.1 ± 2.3, and 74.24 ± 1.42 mg/kg, respectively. Biomass production in the unpolluted soil was 861.13 ± 4.23 g. The biomass production ratio in high Zn-polluted soil was only 3.89%, while it was 4.68% for Cd and 21.4% for Cr. The biomass obtained after napier grass phytoremediation was pretreated using the steam explosion conditions of 180 °C, for 10 min, with 1.5% H2SO2, followed by enzymatic hydrolysis. The efficiency of enzymatic hydrolysis for Zn-polluted biomass was 90% of the unpolluted biomass, while it was 77% for Cd, and approximately the same for Cr. The fermentation efficiency of the heavy-metal-containing biomass was higher than the control biomass. The fermentation ethanol concentration obtained was 8.69-12.68, 13.03-15.50, and 18.48-19.31 g/L in Zn, Cd, and Cr environments, respectively. Results show that the heavy metals had a positive effect on bacteria fermentation. However, the fermentation efficiency was lower for biomass with severe heavy metal pollution. Thus, the utilization of napier grass phytoremediation for bioethanol production has a positive effect on the sustainability of environmental resources.

Two new arylalkenyl α,ß-unsaturated δ-lactones with cytotoxic activity from the leaves and twigs of Cryptocarya concinna.

Tow new arylalkenyl α,ß-unsaturated δ-lactones named cryptoconcatones K (1) and L (2) were obtained from the leaves and twigs of Cryptocarya concinna. Their structures were established on the basis of spectroscopic data (MS, 1D and 2D NMR). Compounds 1 and 2 showed cytotoxic activities with IC50 values of 4.5 and 3.9 µM against Huh7 cancer cell line, respectively.

Nitric Oxide Inhibitory Activity and Absolute Configurations of Arylalkenyl α,ß-Unsaturated δ/γ-Lactones from Cryptocarya concinna.

During an ongoing exploration of potential anti-inflammatory agents from medicinal plants, eight new arylalkenyl α,ß-unsaturated δ-lactones, cryptoconcatones A-H (1-8), and two unusual arylalkenyl α,ß-unsaturated γ-lactones, cryptoconcatones I and J (9 and 10), were identified from the leaves and twigs of Cryptocarya concinna. The structures of these compounds were established based on spectroscopic data (MS, 1D/2D NMR), and their absolute configurations were determined with Riguera's method, the modified Mosher's method, chemical derivatization, and the Snatzke chirality rule. Compounds 4-6 and 8-10 showed inhibitory activity toward nitric oxide (NO) production in lipopolysaccharide-induced RAW 264.7 macrophages, particularly compounds 4 and 8-10, with IC50 values of 3.2, 4.2, 3.4, and 7.5 µM, respectively.

Fabrication of Novel Hydrogel with Berberine-Enriched Carboxymethylcellulose and Hyaluronic Acid as an Anti-Inflammatory Barrier Membrane.

An antiadhesion barrier membrane is an important biomaterial for protecting tissue from postsurgical complications. However, there is room to improve these membranes. Recently, carboxymethylcellulose (CMC) incorporated with hyaluronic acid (HA) as an antiadhesion barrier membrane and drug delivery system has been reported to provide excellent tissue regeneration and biocompatibility. The aim of this study was to fabricate a novel hydrogel membrane composed of berberine-enriched CMC prepared from bark of the P. amurense tree and HA (PE-CMC/HA). In vitro anti-inflammatory properties were evaluated to determine possible clinical applications. The PE-CMC/HA membranes were fabricated by mixing PE-CMC and HA as a base with the addition of polyvinyl alcohol to form a film. Tensile strength and ultramorphology of the membrane were evaluated using a universal testing machine and scanning electron microscope, respectively. Berberine content of the membrane was confirmed using a UV-Vis spectrophotometer at a wavelength of 260 nm. Anti-inflammatory property of the membrane was measured using a Griess reaction assay. Our results showed that fabricated PE-CMC/HA releases berberine at a concentration of 660 µg/ml while optimal plasticity was obtained at a 30 : 70 PE-CMC/HA ratio. The berberine-enriched PE-CMC/HA had an inhibited 60% of inflammation stimulated by LPS. These results suggest that the PE-CMC/HA membrane fabricated in this study is a useful anti-inflammatory berberine release system.