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Five undescribed compounds, including a triterpenoid ( 1 ), three phenylpropanoids [(±)- 2 and 4 ], and an aromatic compound ( 3 ), as well as six known analogues ( 5 - 10 ), were isolated from the resins of Liquidambar orientalis Mill. Their structures, including absolute configurations, were determined by using spectroscopic and computational methods, and the five new compounds displayed anti-inflammatory activities in LPS-induced RAW264.7 cells.

Liquidambar formosana Hance is a pinene-rich deciduous plant species in the Altingiaceae family that is used as a medicinal plant in China. However, the regulatory mechanisms underlying α-pinene and β-pinene biosynthesis in L. formosana leaves remain unknown. Here, a joint analysis of the volatile compounds and transcriptomes of L. formosana leaves was performed to comprehensively explore the terpene synthase (TPS) that may participate in α-pinene and β-pinene biosynthesis. Headspace solid-phase microextraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS) jointly detected volatile L. formosana leaves. Trees with high and low levels of both α-pinene and β-pinene were defined as the H group and L group, respectively. RNA sequencing data revealed that DXR (1-deoxy-D-xylulose-5-phosphate reductoisomerase), HDS [(E)-4-hydroxy-3-methylbut-2-eny-l-diphosphate synthase], and TPS may be the major regulators of monoterpenoid biosynthesis. We identified three TPSs ( LfTPS1, LfTPS2 , and LfTPS3 ), which are highly homologous to α-pinene and β-pinene synthases of other species in phylogenetic analysis. Four TPS genes ( LfTPS1 , LfTPS2 , LfTPS4 , LfTPS5 ) may be critically involved in the biosynthesis and regulation of α-pinene and β-pinene in L. formosana . Bioinformatic and transcriptomic results were verified using quantitative real-time PCR. We identified LfTPS1, LfTPS2 as candidate genes for α-pinene and β-pinene biosynthesis that significantly improve the yield of beneficial terpenoids.

Liquidambar styraciflua L. is an aromatic species, popularly used in traditional Chinese medicine to treat diarrhea, dysentery, coughs, and skin sores. The present study was designed to investigate the chemical composition and biological potential of extracts obtained from the fruits of this plant. For the chemical evaluation, it was used mainly liquid and gas chromatography, plus NMR, and colorimetric methods. The aqueous extract (EA) originated two other fractions: an aqueous (P-EA) and an ethanolic (S-EA). The three extracts were composed of proteins, phenolic compounds, and carbohydrates in different proportions. The analyses showed that the polysaccharide extract (P-EA) contained pectic polysaccharides, such as acetylated and methyl esterified homogalacturonans together with arabinogalactan, while the fraction S-EA presented phenolic acids and terpenes such as gallic acid, protocathecuic acid, liquidambaric acid, combretastatin, and atractyloside A. EA, P-EA, and S-EA showed antioxidant activity, with IC50 values of 4.64 µg/mL, 16.45 µg/mL, and 3.67 µg/mL, respectively. The cytotoxicity followed the sequence S-EA > EA > P-EA, demonstrating that the toxic compounds were separated from the non-toxic ones by ethanol precipitation. While the fraction S-EA is very toxic to any cell line, the fraction P-EA is a promising candidate for studies against cancer due to its high toxicity to tumoral cells and low toxicity to normal cells.

Background: Liquidambaris Fructus is the infructescences of Liquidambar formosana Hance and it has been used to treat some breast disease in Traditional Chinese Medicine. In the previous study we found the anti-breast cancer effect of triterpenoid in Liquidambaris Fructus. This study is a further investigation of the triterpenoids in Liquidambaris Fructus and aims to identify their anti-breast cancer targets, meanwhile, to estimate the rationality of the traditional applications of Liquidambaris Fructus., Methods: Triterpenoids in Liquidambaris Fructus were isolated and their structures were identified by NMR spectrums. Potential targets of these triterpenoids were predicted using a reverse pharmacophore mapping strategy. Associations between these targets and the therapeutic targets of breast cancer were analyzed by constructing protein-protein interaction network, and targets played important roles in the network were identified using Molecular Complex Detection method. Binding affinity between the targets and triterpenoids was studied using molecular docking method. Gene ontology enrichment analysis was conducted to reveal the biological process and signaling pathways that the identified targets were involved in., Results: Thirteen triterpenoids were identified and 6 of them were the first time isolated from Liquidambaris Fructus. Predicted ADME properties revealed a good druggability of these triterpenoids. We identified 18 protein targets which were closely related to breast cancer progression, especially triple-negative, basal-like or advanced stage breast cancers. The triterpenoids could bind with these targets as their inhibitors: hydrophobic skeleton is a favorable factor for them to stabilize at binding site and polar C17- or C3- substituent was necessary for binding. GO enrichment analysis indicated that inhibition of protein tyrosine kinases autophosphorylation might be the primary mechanism for the anti-breast cancer effect of the triterpenoids, and ErbB4 and EGFR were the most relevant targets., Conclusions: The study revealed that triterpenoids from Liquidambaris Fructus might exert anti-breast cancer effect by directly inhibit multiple protein targets and signaling pathways, especially ErbB4 and EGFR and related pathways. This study also brings up another hint that the traditional applications of Liquidambaris Fructus on hypogalactia should be reassessed systematically because it might suppress rather than promote lactation by inhibiting the activity of ErbB4.

A previously undescribed taraxerene-type triterpenoid possessing a class of rare natural taraxerene triterpenoid possessing skeleton with 14, 28-lactone, two undescribed oleane-type triterpenoids, and twenty-five known triterpenoids were isolated from Liquidambar formosana (Hamamelidaceae). The structures of undescribed compounds were determined on the basis of 1D and 2D NMR spectroscopic, HR-ESI-MS, and X-ray crystallographic data analysis. Among the isolates, ursolic acid, 3,6-dion-20(29)-lupen-28-oic acid, and 3-oxo-12α-hydroxyoleanan-28,13β-olide induced a significant apoptosis in SMMC7721 cells in the flow cytometer experiment with apoptosis rates of 94.5%, 57.3% and 89.9% at 8.0 μM, respectively, exhibiting near equivalent apoptosis-inducing abilities to that positive drug taxol (apoptotic rate of 71.2% at 1.4 μM). Mechanism studies suggested that these three compounds could regulate the mitochondrial pathway by up-regulating the expressions of pro-apoptotic factors (Bad and Bax) and activating caspase-3 and caspase-9 to induce apoptosis. Further studies indicated that the pro-apoptotic effects of these three compounds were associated with PI3K-AKT pathway inhibition. Taken together, these studies provide evidence that triterpenoids from L. Fructus are promising candidates for the hepatocellular carcinoma therapy., (Copyright © 2019 Elsevier Ltd. All rights reserved.)

Self-assembled supramolecular gels as a soft material have received extensive attention due to their excellent physicochemical properties such as variability, multiple responsiveness and appropriate viscoelasticity. At present, many self-assembled gels with physicochemical functions are constructed as drug delivery systems and used for the treatment of diseases. However, self-assembled gel drug delivery systems having pharmacological functions remain almost unexplored. Here, we present an anti-inflammatory pharmacologically active gel drug delivery system consisting of direct self-assembled small molecule naturally-occurring compounds (self-assembled small molecule natural products, SSNPs) derived from traditional Chinese medicine. The system not only exhibits excellent thixotropy, good topical safety and sustained release, but also achieves superior inflammatory therapeutic effects both in vivo and in vitro. Compared to non-pharmacologically active drug delivery systems, this system can increase the in vivo anti-inflammatory activity of drugs by nearly two-thirds. More importantly, its therapeutic effect even reached 141.54% of OTC drugs. The successful construction of an anti-inflammatory pharmacologically active gel drug delivery system not only makes full use of the self-assembly properties and biological activity of natural products, but also provides an important reference for the development of pharmacologically active drug delivery systems using SSNPs in the future.

Liquidambar styraciflua L., ALTINGIACEAE, popularly known as sweet gum or alligator tree, is an aromatic tree with a natural distribution in North America and acclimated in Brazil. In traditional medicine, L. styraciflua L is used for the treatment of stomach disorders, wounds, and coughs. The present study was designed to investigate the biological potential and chemical profile of extracts obtained from aerial parts of L. styraciflua L. The chemical profile was established using liquid chromatography-mass spectrometry analysis and the extracts were tested for total phenolics, flavonoids, and tannins using spectrophotometric assays. The anti-inflammatory activity of L. styraciflua L was tested using an inhibition of hyaluronidase enzyme assay, and cytotoxic activities were tested by the 3-(4,5-dimethylthiazol-2 yl)-2, 5-diphenyl tetrazolium bromide (MTT) assay. The synergy between the plant extracts with ciprofloxacin and tetracycline was studied by the checkerboard assay method against eight bacterial strains.The phytochemical investigation showed that the leaves and stem are rich in phenolics compounds (1419.34-1614.02 mg GAE/g, 875.21-1557.57 mg GAE/g, respectively), mainly flavonoids and hydrolyzable tannins. The samples of the stem exhibited the best anti-inflammatory activity. The butanol fraction of the stem was better than the commercial propolis extract. The hydroalcoholic extract of the stem and the propolis did not exhibit significant differences (p < 0.05) at any of the concentrations tested. A synergistic interaction was observed against the Gram-positive bacterial Enterococcus faecalis (hydroalcoholic extract of leaves and tetracycline) and Staphylococcus aureus (hydroalcoholic extract of stem and tetracycline). The IC50 values obtained for the extracts indicate the absence of toxicity and moderate cytotoxic for the hydroalcoholic extract of the stem. On the basis of our findings, L. styaciflua may be considered as a potential therapeutic source with high anti-inflammatory activity and synergistic interactions with antibiotics against bacteria., (Copyright © 2019 Elsevier B.V. All rights reserved.)

Biochar adsorption has been protruded as a sustainable green and economic process for water remediation. This technology is facing high challenges in removing different pollutants, owning to the stable chemical and physical features of biochar. Therefore, a novel nanocomposite of Liquidambar styraciflua fruit biochar-crosslinked-nanosilica (BC-Gl-NSi) was synthesized and characterized (surface area = 60.754 m 2  g -1 and particle size = 17.32-36.25 nm). The designed BC-Gl-NSi nanocomposite was explored for removal of uranyl ions by the batch adsorption technique under the influence of different factors including temperature, contact time, nanocomposite dosage, pH, uranyl ion concentration as well as co-existing ions. The adsorption process was principally confirmed to rely on the solution pH and reached 86.3% in pH 4.0. The results showed also that one-minute contact duration was sufficient to reach the maximum extraction of uranyl (30.0 mg L -1 ). Besides, [BC-Gl-NSi] exhibited excellent selectivity and good recovery of uranyl ions with other competing ions., (Copyright © 2019 Elsevier Ltd. All rights reserved.)

Background and Objective: The fruit of Fructus liquidambaris, which is recently being used for cancer treatment, has a history to be used as a traditional medicine in China for thousands of years., Materials and Methods: Ten kg of dried F. liquidambaris was obtained with 70% alcohol-water solution under reflux for three times. The condensed extract was obtained from petroleum ether, ethyl acetate and N-butyl alcohol, respectively. Ethyl acetate extract was subjected to silica gel column, Sephadex LH-20, ODS column chromatography and RP-HPLC column chromatography to yield a new compound (1). The structure was identified through intensive analysis of NMR and MS spectra. The antitumor mechanism of the furanocoumarin A on human lung cancer A549 cells was confirmed by detecting the apoptosis-related proteins., Results: Furanocoumarin A (1), a novel furanocoumarin constituent was isolated and identified from F. Liquidambaris. The IC50 value of furanocoumarin A on A549 cell lines was 65.28±5.36µM obtained by the method of MTT. The compound could induce the apoptosis of A549 cells by inducing 21.5% early apoptosis and 32.4% late apoptosis at the concentration of 60µmol/L. Western blot analysis indicated that protein expressions of p53, caspase 3 and Bax increased in a dose-dependent manner between the concentrations from 40 to 80µM. The protein expression of Bcl-2 decreased the concentration of 60 and 80µM. The ratio of Bcl-2 to Bax was inversely proportional to the dose concentration., Conclusion: Furanocoumarin A could be a novel anticancer agent from herbal medicine., (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.)

1. This study was carried out to investigate the effects of liquidambar essential oils (LEO) isolated from Turkish sweet gum (Liquidambar orientalis Mill.) leaves on growth performance, carcass, edible inner organs (EIO), gastrointestinal traits (gut), some blood metabolites and jejunum microbiota in broilers. 2. A total of 375 one-d-old male broilers (Ross 308) were randomly allocated to 5 treatments with 5 pens with 15 birds. The birds were fed on diets without antibiotics (CONT), with antibiotic (50 mg per kg, AB), with LEOs at 0.0405 (0.04LEO), 0.0811 (0.08LEO) or 0.1622 (0.16LEO) g/kg feed up to 42 d of age. The levels of LEOs included to diets were determined according to in vitro antimicrobial activity. 3. From d 1 to 42, the 0.08LEO treatment had higher live weight gain (LWG) compared to others. The 0.08LEO treatment increased feed intake (FI) compared to the CONT, AB and 0.04LEO. However, the feed conversion ratio (FCR) of these birds was lower than those in the AB and 0.16LEO treatments. From 1 to 42 d of age for LWG, the effects were quadratic and cubic, while those for FI and FCR were cubic and quadratic, respectively. Birds that fed 0.08LEO and AB diets had higher and lower carcass weights (CW) than those that fed other diets. The effect of LEO levels was cubic on the CW. The 0.08LEO and 0.16LEO decreased abdominal fat (AF) weight compared to the AB. The blood cholesterol decreased by the 0.04LEO and 0.08LEO treatments compared to the CONT. For the blood cholesterol, the effects of LEO levels were cubic. The 0.08LEO treatments decreased Escherichia coli counts in jejunum compared to the CONT and 0.16LEO. 4. Feeding a diet with LEO at 0.0811 g/kg might increase the LWG, FI and weights of carcass and AF, whereas it might decrease blood cholesterol and E. coli counts without affecting blood high-density lipoprotein, low-density lipoprotein, triglyceride, glucose, aspartate transaminase and alanine transaminase concentrations.

Porous carbon spheres with a diameter of 1-2 cm were prepared via a simple carbonization of the fruit of Liquidambar formosana. After carbonization, the spherical structure and inner finger-like pores were maintained with high resistance to impact. Due to the porous structure and the hydrophobic nature, the carbonized fruit of Liquidambar formosana can float on the water surface and show a super-fast oil or organic solvent sorption ability (sorption saturation can be achieved within 1-2 min). Moreover, about 99% of adsorbed oil can be easily removed from spheres via organic solvent such as ethanol or hexane, which shows good recyclability of samples. In general, considering the low-cost and abundance of raw material collected from nature and the facile synthetic process (only by carbonization), the centimeter-sized porous spheres via the carbonization of fruit of Liquidambar formosana are very promising to be used for the application of oil or organic solvent spill cleanup., (Copyright © 2016 Elsevier Ltd. All rights reserved.)

This study investigated the chemical composition, in vitro cytotoxicity, anti-mildew, and anti-wood-decay fungal activities of the essential oil isolated from the fruit of Liquidainbar formosana from Taiwan. The essential oil from the fresh fruit was isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC-MS. A total of 45 compounds were identified, representing 98.5% of the essential oil. The main components identified were a-pinene (16.8%), β-caryophyllene (10.1%), τ-muurolol (8.3%), τ-cadinol (7.6%), β-pinene (6.7%), and sabinene (5.7%). The essential oil exhibited cytotoxic activity against human oral, liver, and lung cancer cells. The active source compounds were β-caryophyllene, τ-cadinol, and τ-muurolol. The fruit essential oil was shown to have excellent anti-mildew and anti-wood-decay fungal activities, the active compounds being evaluated as τ-cadinol and τ-muurolol.

We examined the effects of the extract from leaves of Liquidambar formosana Hance on S180 cells and screened for antitumor active sites in the plant. Solvent extraction was conducted to prepare extracts from the leaves of L. formosana Hance and conduct preliminary separation, an MTT assay to determine the effect of leaf extract on the proliferation of S180 cells, and inverted microscopy to observe the effect of chloroform extract on the morphology of S180 cells. Double-staining (Annexin V/propidium iodide) with flow cytometry was conducted to determine the effect of the chloroform extract on S180 cell apoptosis. At some concentrations, the different extracts from the leaves of L. formosana Hance dose-dependently inhibited the proliferation of S180 cells. Among all extracts, the chloroform extract showed the strongest inhibitory effect on S180 cell proliferation. The IC50 values for the chloroform extract, ethyl acetate extract, n-butanol extract, and water layer were 0.238, 0.471, 0.844, and 0.411 mg/mL, respectively. We observed cell shrinkage, volume reduction, and varying sizes by inverted microscopy. Additionally, with increasing drug concentration, the number of cells decreased and debris increased. The cells showed typical apoptotic morphological changes. The chloroform extract induced the apoptosis of S180 cells in a dose-dependent manner. Different extracts from the leaves of L. formosana Hance inhibited the proliferation of S180 cells, and the chloroform extract was the main antitumor component. This extract from the leaves of L. formosana Hance inhibited the proliferation of S180 cells in part by inducing apoptosis.

Biomass was heated (200-240°C) in the presence of glycerol, for 4-12 min, under shear to disrupt the native cell wall architecture. The impact of this method, named glycerol thermal processing (GTP), on saccharification efficiency of the hardwood Liquidambar styraciflua, and a control cellulose sample was studied as a function of treatment severity. Furthermore, the enzymatic conversion of samples with varying compositions was studied after extraction of the structural polymers. Interestingly, the sweet gum processed materials crystallinity index increased by 10% of the initial value. The experiments revealed that the residual lignin was not a barrier to limiting the digestibility of cellulose after pretreatment yielding up to 70% glucose based on the starting wood material. Further xylan removal greatly improved the cellulose hydrolysis rate, converting nearly 70% of the cellulose into glucose within 24h, and reaching 78% of ultimate glucan digestibility after 72 h., (Copyright © 2015 Elsevier Ltd. All rights reserved.)

Metabolic synthesis of single cell oils (SCOs) for biodiesel application by heterotrophic oleaginous microorganisms is being hampered by the high cost of culture media. This study investigated the possibility of using loblolly pine and sweetgum autohydrolysates as economic feedstocks for microbial lipid production by oleaginous Rhodococcus opacus (R. opacus) PD630 and DSM 1069. Results revealed that when the substrates were detoxified by the removal of inhibitors (such as HMF-hydroxymethyl-furfural), the two strains exhibited viable growth patterns after a short adaptation/lag phase. R. opacus PD630 accumulated as much as 28.6 % of its cell dry weight (CDW) in lipids while growing on detoxified sweetgum autohydrolysate (DSAH) that translates to 0.25 g/l lipid yield. The accumulation of SCOs reached the level of oleagenicity in DSM 1069 cells (28.3 % of CDW) as well, while being cultured on detoxified pine autohydrolysate (DPAH), with the maximum lipid yield of 0.31 g/l. The composition of the obtained microbial oils varied depending on the substrates provided. These results indicate that lignocellulosic autohydrolysates can be used as low-cost fermentation substrates for microbial lipid production by wild-type R. opacus species. Consequently, the variety of applications for aqueous liquors from lignocellulosic pretreatment has been expanded, allowing for the further optimization of the integrated biorefinery.

Objective: To study the chemical constituents of the leaves of Liquidambarformosana., Methods: The chemical constituents were isolated and purified by column chromatography on silicagel, Sephadex LH-20 and MPLC. Their structures were elucidated on the basis of physicochemical properties and special analysis., Results: Eight compounds were isolated from the leaves of Liquidambar formosana, whose structures were elucidated as gallic acid (1), p-hydroxy-benzoic acid (2), 3-methoxy-4-hydroxy-benzoic acid (3), 3,5-dihydroxy-4-methoxy-benzoic acid (4) kaempferol (5), 3,4-dihydroxy-benzoic acid (6), 3,4-dihydroxy-5-methoxy-benzoic acid (7) and 3β,23,29-trihydroxy-olean-12-en-28-oic acid-β-D-glucopyranosyl ester (8)., Conclusion: Compounds 1-8 are isolated from the leaves of Liquidambar formosana for the first time.

This study investigated the fumigant toxicity of oriental sweetgum (Liquidambar orientalis) and valerian (Valeriana wallichii) essential oils and their components against the Japanese termite (Reticulitermes speratus). The fumigant toxicity of oriental sweetgum and valerian oil differed significantly according to exposure time. Oriental sweetgum showed toxicity at short exposure times (2 days), and the toxicity of valerian oil was high 7 days after treatment. The main constituents of oriental sweetgum and valerian oils were tested individually for their fumigant toxicity against Japanese termites. Among the test compounds, benzyl alcohol, acetophenone, 1-phenyl-1-ethanol, hydrocinnamyl alcohol, trans-cinnamyl aldehyde, trans-cinnamyl alcohol, cis-asarone, styrene, and cis-ocimene showed toxicity against Japanese termites 7 days after treatment. Hydrocinnamyl alcohol and trans-cinnamyl alcohol were found to be the major contributors to the fumigant antitermitic toxicity of oriental sweetgum oil. The acetylcholinesterase (AChE) inhibition activity of two oils and their constituents was tested to determine their mode of action. Only cis-ocimene showed strong AChE inhibition activity with an IC50 value of 0.131 mg/mL. Further studies are warranted to determine the potential of these essential oils and their constituents as fumigants for termite control.

The essential oil from Liquidambar formosana leaves (EOLF) was demonstrated to exhibit anti-inflammatory activity in mouse macrophages. EOLF reduced nitrite oxide generation, secretion levels of tumor necrosis factor-alpha and interleukin-6, and expression levels of prointerleukin-beta, inducible nitric oxide synthase, and cyclooxygenase-2 in lipopolysaccharide (LPS)-activated mouse macrophages. EOLF also reduced NLRP3 inflammasome-derived interleukin-1beta secretion. The underlying mechanisms for the EOLF-mediated anti-inflammatory activity were (1) reduction of LPS-induced reactive oxygen species generation; (2) reduction of LPS-induced activation of c-Jun N-terminal kinase, extracellular signal-regulated kinase, and p38 MAP kinase; (3) reduction of LPS-induced nuclear factor-kappaBeta activation. Furthermore, 25 compounds were identified in the EOLF using GC-FID and GC-MS and the major compounds were terpinen-4-ol (32.0%), beta-pinene (18.0%), gamma-terpinene (13.8%), and alpha-terpinene (9.7%). We found that LPS-induced nitrite oxide generation was inhibited significantly by terpinen-4-ol. Our results indicated that EOLF has anti-inflammatory activity and may provide a molecular rationale for future therapeutic interventions in immune modulation.

A rapid, sensitive and reliable liquid chromatography-tandem mass spectrometry method was developed and validated for the determination of betulonic acid in rat plasma. The plasma samples were prepared by protein precipitation. Chromatographic separation was achieved on an Agela MG-C18 analytical column (50 × 2.1 mm, 5 µm) using methanol-water-formic acid (80:20:0.1, v/v/v) as the mobile phase with a constant flow rate of 0.6 mL/min. Mass detection was conducted by electrospray ionization in positive ion multiple reaction monitoring mode. The calibration curves were linear over a concentration range of 3.00-3,000 ng/mL for the analyte. The intra-day and inter-day accuracy and precision were within the acceptable limits of ±15% at all concentrations. The method was successfully applied for the estimation of betulonic acid in rat plasma from a preclinical pharmacokinetics study.

Three new diterpenoids, liquidambolide A (1) and liquiditerpenoic acids A (2) and B (3), together with 10 known diterpenes were isolated from the resin of Liquidambar formosana Hance, whose structures were elucidated by detailed analysis on the NMR and HR-ESI-MS spectra.

It is well known that the isolation of monoamine oxidase (MAO) inhibitors from natural sources is an important strategy for drug development in the treatment of depression, Parkinson's disease and Alzheimer's disease. The present work describes developing a thin-layer chromatography (TLC) bioautographic method for detecting MAO inhibitors from plant extracts. The basic principle of the method is that the enzyme oxidises tryptamine into an aldehyde which in turn reacts with 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyltetrazolium bromide to form a blue formazan which makes a blue-coloured background on the TLC plates. Inhibitors of MAO produced white spots on the background. The new TLC bioautographic method has several advantages such as lower consumption of the enzyme, shorter experimental time, more easily observed background of TLC plate and better reproducibility. The detection limits were 10 ng for several known MAO inhibitors.

Objectives: This study aimed to evaluate the variations of the chemical composition and bioactivity of essential oils of Liquidambar styraciflua L. (Altingiaceae) collected in different seasons., Methods: The oils were analysed by GLC/FID and GLC/MS. The antioxidant activity was investigated by diphenylpicrylhydrazyl (DPPH) and superoxide anion radical scavenging assays and the deoxyribose degradation assay. Inhibition of both 5-lipoxygenase (5-LOX) and prostaglandin E2 (PGE2) production in hepatic cancer (HepG-2) cells were used to assess the anti-inflammatory activity. The cytotoxic activity was investigated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay., Key Findings: Altogether, 64 volatile secondary metabolites were identified. The major components of the leaf oil were d-limonene, α-pinene and β-pinene, and of the stem oil were germacrine D, α-cadinol, d-limonene, α-pinene, and β-pinene. Leaf and stem oils collected in spring could reduce DPPH● (IC50 = 3.17 and 2.19 mg/ml) and prevent the degradation of the deoxyribose sugar (IC50 = 17.55 and 14.29 μg/ml). The stem oil exhibited a higher inhibition of both 5-LOX and PGE2 than the leaf oil. The cytotoxic activity of leaf and stem oils was low in cancer cell lines (IC50 = 136.27 and 119.78 μg/ml in cervical cancer (HeLa) cells)., Conclusions: Essential oils of L. styraciflua exhibited an interesting anti-inflammatory activity with low cytotoxicity, supporting its traditional use to treat inflammation., (© 2013 Royal Pharmaceutical Society.)

The Chinese medicine storax is one of the resuscitation-inducing aromatic herbs used to treat stoke, epilepsy, convulsion, etc. In this review, authors summarized the progress on chemical compositions and anti-cerebral injury effects of storax. Gas chromatography-mass spectrometry (GC-MS) were used to determine the main chemical compositions of storax . And the anti-cerebral ischemia, anti-convulsion, and anti-memory defect effects of storax and its compound preparation were discussed. At last, authors have tried to propose a number of recommendations for the future research.

The goal of this study was to characterize the changes in biomass with torrefaction for near infrared reflectance (NIR) and attenuated total reflectance Fourier transform infrared (ATR-FTIR) spectroscopy for sweetgum, loblolly pine, and switchgrass. Calibration models were built for the prediction of proximate analysis after torrefaction. Two dimensional (2D) correlation spectroscopy between NIR and FTIR was found to precisely explain the depolymerization at key functional groups located within hemicellulose, cellulose, and lignin. This novel 2D technique also demonstrated the possibility of assigning key NIR wavenumbers based on mid IR spectra. Hemicellulose based wavenumbers were found to be most sensitive to torrefaction severity with complete degradation at 250-275°C. Lignin associated wavenumbers exhibited the least degradation to severity but was still detected with 2D correlation spectroscopy. Finally, calibration models for proximate analysis were performed and while both systems could be used for rapid monitoring, NIR performed better than FTIR., (Copyright © 2013 Elsevier Ltd. All rights reserved.)

The aim of this study is to investigate the effects of the storax balsam, which is a kind of sweet gum obtained from the Liquidambar orientalis Mill trees, on cell viability, cytotoxicity and genotoxicity in human lymphocyte in vitro. We studied the genotoxic effects of the extract of storax balsam (SE) using sister chromatid exchange (SCE) test system. Also the cytotoxic and inhibitory effects on cell proliferation of SE were evaluated using lactate dehydrogenase (LDH) assay and cell proliferation (WST-1) assay. The SCE frequency was increased when the cells were treated with 1.6 and 4.0 µg/mL SE concentrations (p < 0.05). Moreover, treatment of the cells with the same concentrations significantly depleted the cell number at 24th and 48th hours and elevated the LDH levels (p < 0.05) at 48th hour. These results suggest that SE can be used as an alternative antibacterial and antipathogenic agent due to its cytotoxic and genotoxic effects.

The interactions between xylan/lignin and cellulase enzymes play a key role in the effective hydrolysis of lignocellulosic biomass. Organosolv pretreated loblolly pine (OPLP) and sweetgum (OPSG) were used to quantitatively elucidate the distinct roles of residual xylan and lignin on enzymatic hydrolysis, based on the initial hydrolysis rates and the final hydrolysis yields. The initial hydrolysis rates of OPLP and OPSG were 1.45 (glucose) and 1.19 g/L/h (glucose), respectively, under the enzyme loading of 20 FPU/g glucan. The final glucan hydrolysis yields of OPLP and OPSG at 72 h were 76.4 and 98.9%, respectively. By correlating the amount of residual lignin and xylan to the initial hydrolysis rate and the final hydrolysis yield in OPLP and OPSG, a more accurate fundamental understanding of the roles of xylan and lignin in limiting the enzymatic hydrolysis has been developed. The higher amount of residual xylan (9.7%) in OPSG resulted in lower initial hydrolysis rate (1.19 g/L/h). The higher amount of residual lignin in OPLP (18.6%) resulted in lower final hydrolysis yield of glucan (76.4%). In addition, we observed in the simultaneous saccharification and fermentation (SSF) that ethyl xyloside was produced by the enzymatic catalysis of xylose/xylan and ethanol.

Two new flavan glycosides, (2S)-5,7,4'-trihydroxyflavan-7-O-β-D-glucopyranoside and (2S)-5,7,4'-trihydroxyflavan-5-O-β-D-glucopyranoside, and a new neolignan, (7S,8S)-3-methoxyl-3'-O-β-D-glucopyrannosyl-4':8,5':7-diepoxyneolignan-4,9'-diol, were isolated from the leaves of Liquidambar formosana Hance. Their structures were elucidated on the basis of spectroscopic data and chemical evidence.

Objective: To develop an HPLC method for content determination of dehydroabietic acid and abietic acid in aqueous alkali extract of Liquidambaris Resina., Method: The determination was carried out on a DIONEX C18 column (4.6 mm x 250 mm, 5 microm) eluted with acetonitrile and water containing 0.1% acetic acid. The flow rate was 1 mL x min(-1), and the detected wavelength was set at 210, 240 nm., Result: The peak areas and the sample quantity of the two components had good linear relationship in the range of 0.4-3.4 microg for dehydroabietic acid, and 0.6-4.8 microg for abietic acid. The average recoveries were 99.53%, 101.9%, respectively., Conclusion: The method was proved to be simple, accurate and used for the quality evaluation of Liquidambaris Resina.

Bio-oil produced from biomass by fast pyrolysis has the potential to be a valuable substitute for fossil fuels. In a recent work on pinewood, we found that pretreatment alters the structure and chemical composition of biomass, which influence fast pyrolysis. In this study, we evaluated dilute acid, steam explosion, and size reduction pretreatments on sweetgum, switchgrass, and corn stover feedstocks. Bio-oils were produced from untreated and pretreated feedstocks in an auger reactor at 450 °C. The bio-oil's physical properties of pH, water content, acid value, density, and viscosity were measured. The chemical characteristics of the bio-oils were determined by gas chromatography-mass spectrometry. The results showed that bio-oil yield and composition were influenced by the pretreatment method and feedstock type. Bio-oil yields of 52, 33, and 35 wt% were obtained from medium-sized (0.68-1.532 mm) untreated sweetgum, switchgrass, and corn stover, respectively, which were higher than the yields from other sizes. Bio-oil yields of 56, 46, and 51 wt% were obtained from 1% H(2)SO(4)-treated medium-sized sweetgum, switchgrass, and corn stover, respectively, which were higher than the yields from untreated and steam explosion treatments.

Two new lupene-type triterpenoids, 3β,6β-dihydroxylup-20(29)-en-28-oic acid β-glucopyranosyl ester (1) and 2α-acetoxyl-3β,6β-dihydroxylup-20(29)-en-28-oic acid β-glucopyranosyl ester (2), along with 18 known compounds, were isolated from Liquidambar formosana. The structures were elucidated on the basis of spectroscopic methods, including UV, IR, ESIMS, 1D- and 2D-NMR experiments, as well as by comparison of the spectral data with those of related compounds.

Two new pentacyclic triterpenes and eight known pentacyclic triterpenes were isolated from the petroleum ether extract of Liquidambaris Resina. The structural elucidation of these compounds was determined by spectroscopic data interpretation. Their cytotoxic and antiplatelet aggregation activities were examined to find potent cytotoxic and antiplatelet aggregation compounds from natural resources. The results showed that 3-keto oleane triterpenes had strong cytotoxicity against MDA-MB-435S cancer cells and that 28-carboxyl oleane triterpenes possessed significant inhibition of platelet aggregation induced by ADP., (Copyright © 2011 Elsevier B.V. All rights reserved.)

Liquidambar styraciflua L., also known as sweetgum, is an understory hardwood species that has widespread distribution in the southeast USA, especially in pine plantations. In addition to being a possible biorefinery feedstock, sweetgum contains shikimic acid, which is a precursor for the drug Tamiflu. Sweetgum bark was extracted with 65 degrees C water and yielded 1.7 mg/g of shikimic acid, while sweetgum de-barked wood yielded 0.2 mg/g of shikimic acid. Because shikimic acid can be extracted with water, the coupling of the phytochemical hot water extraction with dilute acid pretreatment was examined. The addition of a 65 degrees C shikimic acid extraction step coupled to pretreatment with 0.98% H(2)SO(4) at 130 degrees C for 50 min resulted in 21% and 17% increases in xylose percent recovery from bark and de-barked wood, respectively. These results indicate that, in addition to recovering a high value product, the 65 degrees C wash step also increases xylose recovery.

Since its establishment, a hybrid origin for Semiliquidambar has been proposed based on morphological intermediacy and sympatric distribution with Altingia and Liquidambar. This hypothesis, however, has lacked convincing molecular evidence. In this study, two nuclear genes, pin2 and cab4, and a chloroplast gene, matK, from Semiliquidambar cathayensis and its putative parental species Liquidambar and Altingia in Jianfengling, Hainan, and Heishiding and Nanling, Guangdong, China, were sequenced to test this hypothesis. Our results showed that L. formosana and L. acalycina were closely related and constituted an inseparable clade in the phylogenetic trees of both pin2 and cab4 genes. Phylogenetic analyses revealed two types of sequences for S. cathayensis, which were clustered with its putative parents, L. formosana-L. acalycina and A. obovata in Jianfengling, and with L. formosana-L. acalycina and A. chinensis in Heishiding and Nanling. The partial chloroplast matK gene sequences showed four nucleotide substitutions between L. formosana and A. obovata in Jianfengling; the sequences of the two individuals of S. cathayensis were identical with those of A. obovata. No diagnostic chloroplast markers including matK and three other chloroplast genes were found to distinguish L. formosana and A. chinensis in Heishiding and Nanling. Molecular data clearly demonstrated that S. cathayensis is of intergeneric hybrid origin between L. formosana-L. acalycina and A. obovata or A. chinensis and that A. obovata functions as the maternal parent in the hybridization event in Jianfengling, Hainan.

Nitrogen (N) cycling can be an important constraint on forest ecosystem response to elevated atmospheric CO(2). Our objective was to trace the movement of (15)N, injected into tree sap, to labile and stable forms of soil organic matter derived partly from the turnover of tree roots under elevated (545 ppm) and ambient (394 ppm) atmospheric CO(2) concentrations at the Oak Ridge National Laboratory (ORNL) FACE (Free-Air Carbon Dioxide Enrichment) Experiment. Twenty-four sweetgum trees, divided equally between CO(2) treatments, were injected with 3.2 g (15)N-ammonium sulfate (99 atom %), and soil samples were collected beneath the trees over a period of 89 weeks. For 16 cm deep soil samples collected beneath the study trees, there was 28% more fine root (less than or equal to 2 mm diameter) biomass under elevated CO(2) (P = 0.001), but no significant treatment effect on the amounts of necromass, coarse root biomass, or on the N concentrations in tree roots and necromass. Nitrogen-15 moved quickly into roots from the stem injection site and the (15)N content of roots, necromass, and labile organic matter (i.e. particulate organic matter, POM) increased over time. At 89 weeks post-injection, approximately 76% of the necromass (15)N originated from fine root turnover. Nitrogen-15 in POM had a relatively long turnover time (47 weeks) compared with (15)N in roots (16 to 22 weeks). Over the 1.7 year period of the study, (15)N moved from roots into slower cycling POM and the disparity in turnover times between root N and N in POM could impose progressive limitations on soil N availability with stand maturation irrespective of atmospheric CO(2), especially if the release of N through the decomposition of POM is essential to sustain forest net primary production., (Published in 2009 by John Wiley & Sons, Ltd.)

Commercial essential oils from 28 plant species were tested for their nematicidal activities against the pine wood nematode, Bursaphelenchus xylophilus. Good nematicidal activity against B. xylophilus was achieved with essential oils of coriander (Coriandrum sativum), Oriental sweetgum (Liquidambar orientalis), and valerian (Valeriana wallichii). Analysis by gas chromatography-mass spectrometry led to the identification of 26, 11, and 4 major compounds from coriander (Coriandrum sativum), Oriental sweetgum (Liquidambar orientalis), and valerian (Valeriana wallichii) oils, respectively. Compounds from each plant essential oil were tested individually for their nematicidal activities against the pine wood nematode. Among the compounds, benzaldehyde, trans-cinnamyl alcohol, cis-asarone, octanal, nonanal, decanal, trans-2-decenal, undecanal, dodecanal, decanol, and trans-2-decen-1-ol showed strong nematicidal activity. The essential oils described herein merit further study as potential nematicides against the pine wood nematode.

Hypertension is a lifestyle-related disease which often leads to serious conditions such as heart disease and cerebral hemorrhage. Angiotensin II (Ang II) plays an important role in regulating cardiovascular homeostasis. Consequently, antagonists that block the interaction of Ang II with its receptors are thought to be effective in the suppression of hypertension. In this study, we searched for plant compounds that had antagonist-like activity toward Ang II receptors. From among 435 plant samples, we found that EtOH extract from the resin of sweet gum Liquidambar styraciflua strongly inhibited Ang II signaling. We isolated benzyl benzoate and benzyl cinnamate from this extract and found that those compounds inhibited the function of Ang II in a dose-dependent manner without cytotoxicity. An in vivo study showed that benzyl benzoate significantly suppressed Ang II-induced hypertension in mice. In addition, we synthesized more than 40 derivatives of benzyl benzoate and found that the meta-methyl and 3-methylbenzyl 2'-nitrobenzoate derivatives showed about 10-fold higher activity than benzyl benzoate itself. Thus, benzyl benzoate, its derivatives, and benzyl cinnamate may be useful for reducing hypertension.

An efficient partial synthesis of 25-acetoxy-3alpha-hydroxyolean-12-en-28-oic acid (1), starting from oleanolic acid (2), has been developed in an efficient manner (13 steps, 21% yield), employing a photochemical reaction of nitrite 8 for the introduction of C-25 substituting group as the key step. Based on the comparison of its spectral data with those reported for compound 1 isolated from Liquidamber styraciflua, we found the structure in that paper was incorrectly assigned, and should be revised as 3alpha-acetoxy-25-hydroxyolean-12-en-28-oic acid (15).

Objective: To develop a RP-HPLC method for determination of cinnamic acid in rat plasma., Method: The plasma samples were acidified with acetic acid and extracted with chloroform. Cinnamic acid was separated on a Kromasil C18 column (250 mm x 4.6 mm, 5 microm) eluted with a mobile phase of methanol-acetonitrile-water-glacial acetic acid (25:20:55:0.3) at a flow rate of 1.0 mL x min(-1) and room temperature with UV detection at 278 nm, carbamazepine as internal standard., Result: The standard curve was linear over the range of 4.0 to approximately 400 ng x mL (-1) r = 0..99 9. The LOQ was 4.0 ng x mL(-1), the mean extraction recovery of the spiked samples at low, middle and high levels was 86.4%, while the mean method recovery was 100.3%. The RSD of intra-day and inter-day were both less than 6.0%., Conclusion: The method was sensitive, specific, accurate and precise, which was used to study the pharmacokinetic profile of cinnamic acid in rat plasma after oral administration of the Subing orally disintegrating tablets.

Lymantria xylina Swinhoe (Lepidoptera: Lymantriidae) is a serious defoliator of hardwood and fruit trees in Taiwan. The larvae of L. xylina feed on >63 species of host plants, belonging to 29 families. Because a large number of larvae are needed for the production of nucleopolyhedrosis virus (NPV) or other related studies, the development of a suitable artificial diet is very important for the mass rearing of this moth in the laboratory. In this study, eight artificial diets, modified from different formulas, and one host plant, Liquidambar formosana Hance, were used to feed L. xylina caterpillars. Through various bioassays (first instar survival trial and long- and short-term feeding trials), the most suitable diet for the L. xylina was selected by performance comparisons with L. formosana. After the first instar survival trial, two of the diets were discarded, because no larva survived on these diets. The results of the long-term feeding trial indicated that the larvae grew successfully on only three kinds of artificial diet. Finally, results of the short-term feeding trial revealed that a diet (diet A), modified from the gypsy moth, Lymantria dispar (L.), formula diet, was the most appropriate for the L. xylina. Larvae fed on diet A had better survival rate, pupal weight, adult size, efficiency of conversion, and relative growth rate than larvae fed on other diets; they did not grow as well as those fed on L. formosana, however, except for pupal and adult weight, and approximate digestibility. In summary, diet A was found to be the best of the artificial diets for the L. xylina and is suitable for mass rearing of this moth in the laboratory.

Objective: To establish a determination method of aristolochic acid A in Guanxisuhe preparations by RP-HPLC., Method: The instrument used was Hewlett-Packard 1100 HPLC with a Alltech C18 column (4.6 mm x 250 mm, 5 microm). The mobile phase was methanol-water-acetic acid (68: 32:1) and the flow rate was 1.0 mL x min(-1). The UV detection wavelength was 390 nm and the column temperature was at 35 degrees C. The extracted solvent for the preparations was methanol solution contained 10% formic acid., Result: The calibration curve was linear (r = 0.999 9) within the range of 0.119-1.89 microg for aristolochic acid A. The average recovery 99.0%, RSD 0.63%., Conclusion: The method with good linear relationship was convenient, quick, accurate, and suitable for the quality control of the aristolochic acid A in Guanxinsuhe and other traditional Chinese medicines containing aristolochic acid A.

Objective: To develop the identification and assay methods for betulonic acid in fruits of Liquidambar formosana., Method: TLC method was used for identification with silica gel G plate and petroleum ether(60-90 degrees C)-acetone (17:3) as a developing solvent. Betulonic acid in ethanol extract was separated on the ODS column with methanol-water-glacial acetic acid (87:13:0.1) as mobile phase. Flow-rate was 1.0 mL x min(-1), and column temperature 35 degrees C. ELSD drift-tube temperature was 82 degrees C, and gas flow 1.25 L x min(-1)., Result: The qualitative method is repeatable. Betulonic acid in ethanol extracts is well separated, relationship of logarithms of injection amount and peak area is linear (r = 0.9997) within the range of 0.65-3.25 microg. The average recovery is 98.0% and RSD of repeatability is 2.5%. 11 crude drugs purchased from different areas in the country were identified and quantified with the methods., Conclusion: The methods and data could be used for quality control of fruits of L. formosana.

Objective: To study the chemical constituents from the methanolic extract from the leaf of Liquidambar formosana Hance., Method: The compounds were separated with the column chromatographic and Prep HPLC, and their structures were identified by chemical and spectroscopic methods., Results: Three compounds were isolated from the methanolic extract. They were identified as: beta-sitosterol (I), alpha-amyrin (II) and oleanonic acid (III)., Conclusion: All of them were isolated from this plant for the first time.

In a search for cancer chemopreventive agents from natural sources, four lupane-type and seven oleanane-type triterpenoids, and ten synthetic analogs were screened as potential anti-tumor promoters by using the in vitro short-term 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced Epstein-Barr virus early antigen (EBV-EA) activation assay. Among them, 25-acetoxy-3alpha-hydroxyolean-12-en-28-oic acid (1) and 3beta,25-epoxy-3alpha-hydroxylup-20(29)-en-28-oic acid (2) were examined for anti-tumor promoting activity in a two-stage carcinogenesis assay on mouse skin with 7,12-dimethylbenz[a]anthracene (DMBA) and TPA as promoter. 25-Acetoxy-3alpha-hydroxyolean-12-en-28-oic acid (1) and 3beta,25-epoxy-3alpha-hydroxylup-20(29)-en-28-oic acid (2) showed moderate inhibitory activities.

In a search for inhibitory components from natural products against NFAT transcription factor, this study investigated the ethyl acetate extract of the fruits of Liquidambar formosana. Four oleanane triterpenoids were isolated and identified to be liquidambaric acid, oleanolic acid, 3alpha-acetoxy-25-hydroxy-olean-12-en-28-oic acid and lantanolic acid. Of these compounds, 3alpha-acetoxy-25-hydroxy-olean-12-en-28-oic acid (IC50: 4.63 microM) and lantanolic acid (IC50: 12.62 microM) exhibited strong inhibitory activity against the NFAT transcription factor.

Aim: To study the chemical composition in the fruits of Liquidambar formana Hance., Methods: Various column chromatographic techniques were used to separate and purify the constituents. Their physical and chemical properties and spectral data were measured for structural elucidation., Results: Eleven compounds were isolated and identified as beta-sitosterol (1), 3-oxo-11 alpha, 12 alpha-epoxyleanan-28, 13 beta-olide (2), 3-oxo-12 alpha-hydroxy-oleanan-28, 13 beta-olide (3), 3 alpha-acetyloxy-25-hydroxyolean-12-en-28-oic acid (4), oleanolic acid (5), ursolic acid (6), daucosterol (7), betulonic acid (8), gallic acid (9), nonacosane (10) and n-triacontanoic acid (11)., Conclusion: Among the isolated constituents, compound 4 is new compound, compound 3 is firstly isolated from the natural product and compound 5, 6, 7, 9, 10 and 11 are isolated from LuLuTong for the first time.