Separation and purification of benzylester glucosides and derivatives from tubers of Gymnadenia conopsea (L.) R. Br. by linear gradient counter-current chromatography combined with elution-extrusion mode.

Tubers of Gymnadenia conopsea (L.) R. Br. (Orchidaceae), a traditional medicine and food homologous plant, has a broad application and development prospect in the food and drug industries. Benzylester glucosides, the main effective active components in this plant, are difficult to separate due to their similar structures and high polarity. In this study, linear gradient counter-current chromatography was used to separate benzylester glucosides and derivatives, combined with elution-extrusion mode. The main separation parameters were optimized, including the ratio of mobile phase and sample loading. Finally, seven compounds were successfully separated, including 4-hydroxybenzyl alcohol (1), 4-hydroxybenzaldehyde (2), dactylorhin B (3), loroglossin (4), dactylorhin A (5), 4-(ethoxymethyl) phenol (6), and militarine (7). The structures were analyzed by mass spectrometry and nuclear magnetic resonance spectrometry. According to our findings, the established method was an efficient approach to separate benzylester glucosides and derivatives from tubers of G. conopsea. The established strategy could be applied to purify other similar high-polarity compounds from complex natural products.

Electrospun nanofibers-based thin film microextraction for enrichment of phthalate esters in biodegradable plastics.

In this work, a novel electrospun nanofiber (PAN/TpBD; 2,4,6-triformylphloroglucinol [Tp] and benzidine [BD]; polyacrylonitrile [PAN]) was fabricated via a facile electrospinning method and utilized as adsorbent in thin film microextraction (TFME) of phthalate esters (PAEs) (dimethyl phthalate, diethyl phthalate, diallyl phthalate, dibutyl phthalate, and dioctyl phthalate) in biodegradable plastics. The prepared PAN/TpBD combines the strong stability of nanofibers with increased exposure sites for covalent organic frameworks and enhanced interactions with the target, thus improving the enrichment effect on the target. The extraction efficiency of PAN/TpBD reached above 80%. Based on PAN/TpBD, a TFME-high-performance liquid chromatography method was established, and the experimental parameters were optimized. Under the optimal extraction conditions, the PAEs of this method varied linearly in the range of 10-10 000 µg/L with low detection limits (0.69-2.72 µg/L). The intra-day and inter-day relative standard deviation values of the PAEs were less than 8.04% and 8.73%, respectively. The adsorbent can achieve more than 80% recovery of the five targets after six times reuse. The developed method was successfully applied for the determination of trace PAEs in biodegradable plastics with recoveries ranging from 80.1% to 113.4% and relative standard deviations were less than 9.45%. The as-synthesized PAN/TpBD adsorbent exhibited great potential in PAE analysis.

Reversed-Phase Medium-Pressure Liquid Chromatography Purification of Omega-3 Fatty Acid Ethyl Esters Using AQ-C18.

Omega-3 fatty acids are in high demand due to their efficacy in treating hypertriglyceridemia and preventing cardiovascular diseases. However, the growth of the industry is hampered by low purity and insufficient productivity. This study aims to develop an efficient RP-MPLC purification method for omega-3 fatty acid ethyl esters with high purity and capacity. The results indicate that the AQ-C18 featuring polar end-capped silanol groups outperformed C18 and others in retention time and impurity separation. By injecting pure fish oil esters with a volume equivalent to a 1.25% bed volume on an AQ-C18 MPLC column using a binary isocratic methanol-water (90:10, v:v) mobile phase at 30 mL/min, optimal omega-3 fatty acid ethyl esters were obtained, with the notable purity of 90.34% and a recovery rate of 74.30%. The total content of EPA and DHA produced increased from 67.91% to 85.27%, meeting the acceptance criteria of no less than 84% set by the 2020 edition of the Pharmacopoeia of the People's Republic of China. In contrast, RP-MPLC significantly enhanced the production efficiency per unit output compared to RP-HPLC. This study demonstrates a pioneering approach to producing omega-3 fatty acid ethyl esters with high purity and of greater quantity using AQ-C18 RP-MPLC, showing this method's significant potential for use in industrial-scale manufacturing.

Three Undescribed Protoilludane-Type Sesquiterpene Aryl Esters from Armillaria gallica.

Three previously undescribed protoilludane-type sesquiterpene aryl esters, armillanals A-C (1-3), along with seven known ones (4-10) were obtained from Armillaria gallica Marxm. & Romagn. Compounds 1 and 2 were a rare class of sesquiterpenes featuring the Δ2(3) and Δ12(13)-protoilludane skeleton. Their structures were established by extensive spectroscopic methods. Based on electronic circular dichroism (ECD) calculations, the absolute configurations of three new compounds (1-3) were determined. The anti-inflammatory activity of compounds 1-10 was screened and compound 3 could dose-dependently decrease the level of lactate dehydrogenase, showing IC50 value of 4.525 µM.

Antiplatelet and Anticoagulant Effects of Two New Phenylpropanoid Sucrose Esters and Other Secondary Metabolites from the Aerial Part of Canna edulis.

This study isolated pure compounds from Canna edulis aerial parts and assessed their antiplatelet and anticoagulant potential. Structural elucidation resulted in the identification of two new compounds: caneduloside A (1) and caneduloside B (2), and eleven known compounds: 6'-acetyl-3,6,2'-tri-p-coumaroyl sucrose (3), 6'-acetyl-3,6,2'-triferuloyl sucrose (4), tiliroside (5), afzelin (6), quercitrin (7), 2-hydroxycinnamaldehyde (8), cinnamic acid (9), 3,4-dimethoxycinnamic acid (10), dehydrovomifoliol (11), 4-hydroxy-3,5-dimethoxybenzaldehyde (12), and (S)-(-)-rosmarinic acid (13). Compounds 3, 4, 6-9, 13 were previously reported for antithrombotic properties. Hence, antithrombotic tests were conducted for 1, 2, 5, 10-12. All tested compounds demonstrated a dose-dependent antiaggregatory effect, and 10 and 12 were the most potent for both ADP and collagen activators. Additionally, 10 and 12 showed anticoagulant effects, with prolonged prothrombin time and activated partial thromboplastin time. The new compound 1 displayed antiplatelet and anticoagulant activity, while 2 mildly inhibited platelet aggregation. C. edulis is a potential source for developing antithrombotic agents.

Discovery, semisynthesis and neurite outgrowth-promoting activity of novel merrillianone/cycloparviforalone based esters as neurotrophic agents.

Natural products (NPs) are very important sources for the development of new drugs. Merrillianone and cycloparvifloralone, isolated from the roots, stems, and fruits of Illicium henryi Diels, are two natural sesquiterpene compounds. In continuation of our effort to discovery more effective neurotrophic compounds from NPs, a series of novel merrillianone/cycloparviforalone based esters 2a-i, 3a-g and 3i-q were prepared and their structures were characterized by 1H NMR, 13C NMR and IR spectral analyses. Furthermore, the spatial structure of compound 2h was unambiguously confirmed by X-ray crystallography. The neurite outgrowth-promoting activity results indicated that most of the target derivatives exhibited more potent neurite outgrowth-promoting activity than merrillianone and cycloparviforalone. Among all target derivatives, the neurite outgrowth-promoting activity of compounds 2a, 3a and 3b was about 2-fold stronger than that of their precursors merrillianone and cycloparviforalone, respectively. Besides, compounds 2a and 3a displayed relatively low cytotoxicity to normal GES-1 cells. Moreover, these derivatives had good hydrolytic stability. Finally, some interesting results of the structure-activity relationships (SARs) were also discussed. This work will pave the way for the development of merrillianone/cycloparviforalone derivatives as potential neurotrophic agents.

Shrimp Oil Extracted from Shrimp Processing By-Product Is a Rich Source of Omega-3 Fatty Acids and Astaxanthin-Esters, and Reveals Potential Anti-Adipogenic Effects in 3T3-L1 Adipocytes.

The province of Newfoundland and Labrador, Canada, generates tons of shrimp processing by-product every year. Shrimp contains omega (n)-3 polyunsaturated fatty acids (PUFA) and astaxanthin (Astx), a potent antioxidant that exists in either free or esterified form (Astx-E). In this study, shrimp oil (SO) was extracted from the shrimp processing by-product using the Soxhlet method (hexane:acetone 2:3). The extracted SO was rich in phospholipids, n-3 PUFA, and Astx-E. The 3T3-L1 preadipocytes were differentiated to mature adipocytes in the presence or absence of various treatments for 8 days. The effects of SO were then investigated on fat accumulation, and the mRNA expression of genes involved in adipogenesis and lipogenesis in 3T3-L1 cells. The effects of fish oil (FO), in combination with Astx-E, on fat accumulation, and the mRNA expression of genes involved in adipogenesis and lipogenesis were also investigated. The SO decreased fat accumulation, compared to untreated cells, which coincided with lower mRNA expression of adipogenic and lipogenic genes. However, FO and FO + Astx-E increased fat accumulation, along with increased mRNA expression of adipogenic and lipogenic genes, and glucose transporter type 4 (Glut-4), compared to untreated cells. These findings have demonstrated that the SO is a rich source of n-3 PUFA and Astx-E, and has the potential to elicit anti-adipogenic effects. Moreover, the SO and FO appear to regulate adipogenesis and lipogenesis via independent pathways in 3T3-L1 cells.

Separation and Identification of Resveratrol Butyrate Ester Complexes and Their Bioactivity in HepG2 Cell Models.

Resveratrol butyrate ester (RBE) complexes have demonstrated higher antioxidant capacity and anti-fat accumulation activity in previous studies. In this study, silica gel, high-performance liquid chromatography, and 1H nuclear magnetic resonance were used for separation and identification of RBE complex components. With the exception of resveratrol, five different structures of ester derivatives were separated from silica gel: 3,4'-di-O-butanoylresveratrol (ED2, 18.8%), 3-O-butanoylresveratrol (ED4, 35.7%), 4'-O-butanoylresveratrol (ED5, 4.4%), 3,5,4'-tri-O-butanoylresveratrol (ED6, 1.5%), and 3,5-di-O-butanoylresveratrol (ED7, 0.7%). Among the ester derivatives obtained, ED2 and ED4 were the main ester derivatives in the RBE complex. Thus, the cellular antioxidant activities of the RBE mixture, ED2, and ED4 were evaluated. Results showed that the antioxidant capacity of ED2 and ED4 was higher than that of the RBE mixture, demonstrating that the number and position of butyrate esterification sites are related to cell survival rate and antioxidant capacity. This study is the first to report the successful isolation, structural identification, and cellular biological antioxidant activity of RBE complex derivatives, which are key characteristics for the potential practical application of RBE complexes.

A Novel Antibacterial Component and the Mechanisms of an Amaranthus tricolor Leaf Ethyl Acetate Extract against Acidovorax avenae subsp. citrulli.

The aim of the present investigation was to determine the active ingredients in Amaranthus tricolor L. leaves and develop a biological pesticide. Organic solvent extraction, column chromatography, liquid chromatography, ODS-C18 reverse elution, Sephadex LH-20 gel filtration, H spectrum, and C spectrum were used to isolate the pure product for an assessment of the agricultural activity and bacteriostatic mechanisms. The results showed that the activity of the crude extract following carbon powder filtration was 1.63-fold that of the non-filtered extract. Further isolation was performed to obtain two pure products, namely, hydroxybenzoic acid (HBA) and benzo[b]furan-2-carboxaldehyde (BFC), and their molecular formulas and molecular weights were C7H6O3 and 138.12, and C9H6O2 and 146.12, respectively. Our study is the first to determine that HBA has bacteriostatic activity (MIC 125 µg/mL) and is also the first to isolate BFC from A. tricolor. The ultrastructure observation results showed that HBA caused the bacteria to become shriveled, distorted, and deformed, as well as exhibit uneven surfaces. After HBA treatment, 70 differentially expressed metabolites were detected in the bacteria, of which 9 were downregulated and 61 were upregulated. The differentially expressed metabolites were mainly strigolactones, organic acids and derivatives, fatty acids, benzene and substituted benzene derivatives, amino acids and associated metabolites, and alcohols and amines. Among all of the downregulated differentially expressed metabolites, MEDP1280 was the most critical, as it participates in many physiological and biochemical processes. The enrichment analysis showed that the differentially expressed metabolites mainly participate in tyrosine metabolism, biosynthesis of amino acids, cysteine and methionine metabolism, and arginine and proline metabolism. Additionally, HBA was found to disrupt cell membrane permeability and integrity, causing the leakage of substances and apoptosis. The physiological and biochemical test results showed that HBA could increase the pyruvate levels in bacteria but could decrease the activities of respiratory enzymes (malate dehydrogenase (MDH) and NADH oxidase) and antioxidant enzymes (superoxide dismutase (SOD) and glutathione peroxidase (GSH-PX)). Inverse molecular docking was used to study the binding between HBA and respiratory and antioxidant enzymes. The results showed that HBA could bind to MDH, NADH oxidase, SOD, and GSH-PX, suggesting that these enzymes may be the effector targets of HBA. Conclusion: The optimal active ingredient in A. tricolor that can inhibit Acidovorax avenae subsp. citrulli was identified as HBA. HBA mainly disrupts the cell membrane, damages the metabolic system, and inhibits respiration and antioxidant enzyme activity to control bacterial growth. These results provide a reference for the further development of biological pesticides.

Evaluation of the Removal of Selected Phthalic Acid Esters (PAEs) in Municipal Wastewater Treatment Plants Supported by Constructed Wetlands.

Phthalic acid esters (PAEs) have a negative impact on living organisms in the environment, therefore, are among the group of Endocrine Disrupting Compounds (ECDs). Unfortunately, conventional methods used in municipal wastewater treatment plants (MWWTPs) are not designed to eliminate PAEs. For this reason, the development of cheap and simple but very effective techniques for the removal of such residues from wastewater is crucial. The main aim of this study was the evaluation of the removal of six selected PAEs: diethyl phthalate (DEP), di-n-octyl phthalate (DOP), di-n-butyl phthalate (DBP), benzyl butyl phthalate (BBP), bis(2-ethylhexyl) phthalate (DEHP) and dimethyl phthalate (DMP), in real MWWTPs supported by constructed wetlands (MWWTP-CW system). For the first time, the possibility of using three new plants for this purpose, Cyperus papyrus (papyrus), Lysimachia nemorum (yellow pimpernel) and Euonymus europaeus (European spindle), has been presented. For determining the target PAEs in wastewater samples, a method of SPE (Solid-Phase Extraction)-GC-MS(SIM) was developed and validated, and for plant materials, a method of UAE (Ultrasound-Assisted Extraction)-SPE-GC-MS(SIM) was proposed. The obtained data showed that the application of the MWWTP-CW system allows a significant increase in the removal of DEP, DBP, BBP and DEHP from the wastewater stream. Euonymus europaeus was the most effective among the tested plant species for the uptake of analytes (8938 ng × g-1 dry weight), thus, this plant was found to be optimal for supporting conventional MWWTPs.

Structural Characterization of Unusual Fatty Acid Methyl Esters with Double and Triple Bonds Using HPLC/APCI-MS2 with Acetonitrile In-Source Derivatization.

Double and triple bonds have significant effects on the biological activities of lipids. Determining multiple bond positions in their molecules by mass spectrometry usually requires chemical derivatization. This work presents an HPLC/MS method for pinpointing the double and triple bonds in fatty acids. Fatty acid methyl esters were separated by reversed-phase HPLC with an acetonitrile mobile phase. In the APCI source, acetonitrile formed reactive species, which added to double and triple bonds to form [M + C3H5N]+• ions. Their collisional activation in an ion trap provided fragments helpful in localizing the multiple bond positions. This approach was applied to fatty acids with isolated, cumulated, and conjugated double bonds and triple bonds. The fatty acids were isolated from the fat body of early-nesting bumblebee Bombus pratorum and seeds or seed oils of Punicum granatum, Marrubium vulgare, and Santalum album. Using the method, the presence of the known fatty acids was confirmed, and new ones were discovered.

Chemical Components and Antibacterial Activity of the Essential Oil of Six Pyrrosia Species.

The present study was aimed at analyzing the chemical components of the essential oil from six Pyrrosia species by GC/MS and evaluating their in vitro antibacterial activities. Seventy volatile compounds were identified in the essential oil of six Pyrrosia samples. The identified volatile components were divided into following nine categories: aldehydes, terpenoids, fatty acids, ketones, furans, hydrocarbons, alcohols, esters, and phenols. The major components of the essential oil were 2,4-pentadienal, phytol and nonanal. The antimicrobial assays showed that the essential oils from Pyrrosia samples exhibited a broad-spectrum antimicrobial activity. However, P. lingua had the highest antibacterial activity against Staphylococcus aureus (ATCC 25923) with a minimum inhibitory concentration (MIC) of 2.5 µL/mL. This article is the first report of the chemical components and antimicrobial activity of the essential oil from six Pyrrosia species, which will lay the foundation for developing medicinal resources from Pyrrosia fronds.

Volatile Profile in Yogurt Obtained from Saanen Goats Fed with Olive Leaves.

The aim of this study was to evaluate the development of volatile compounds in yogurt samples obtained from goats fed a dietary supplementation with olive leaves (OL). For this purpose, thirty Saanen goats were divided into two homogeneous groups of 15 goats each: a control group that received a standard diet (CG) and an experimental group whose diet was supplemented with olive leaves (OLG). The trial lasted 28 days, at the end of which the milk of each group was collected and used for yogurt production. Immediately after production, and after 7 days of storage at 4 °C in the absence of light, the yogurt samples were characterized in terms of fatty acid profile, oxidative stability and volatile compounds by the solid-phase microextraction (SPME)-GC/MS technique. Dietary OL supplementation positively affected the fatty acid composition, inducing a significant increase in the relative proportion of unsaturated fatty acids, mainly oleic acid (C18:1 cis9) and linolenic acid (C18:3). With regard to the volatile profile, both in fresh and yogurt samples stored for 7 days, the OL supplementation induced an increase in free fatty acids, probably due to an increase in lipolysis carried out by microbial and endogenous milk enzymes. Specifically, the largest variations were found for C6, C7, C8 and C10 free fatty acids. In the same samples, a significant decrease in aldehydes, mainly heptanal and nonanal, was also detected, supporting-at least in part-an improvement in the oxidative stability. Moreover, alcohols, esters and ketones appeared lower in OLG samples, while no significant variations were observed for lactones. These findings suggest the positive role of dietary OL supplementation in the production of goats' milk yogurt, with characteristics potentially indicative of an improvement in nutritional properties and flavor.

Sunflower wax recovered from oil tank settlings: Revaluation of a waste product from the oilseed industry.

BACKGROUND: The sunflower oil industry produces a large amount of waste that is not currently commercially exploited, as in the case of oil-tank settlings. The recovery of a high value-added by-product, such as sunflower wax, would increase the commercial value of this waste. In this original research paper, a method that allows the recovery and purification of this by-product was developed. The wax was characterized and its potential use as an organogelator agent was investigated. RESULTS: The waste sample was composed of 45.1% oily material, 16.9% of this being impure waxes. Purification was performed through two different methods, obtaining three waxes with different degrees of purity. All the waxes were composed of wax esters with a range of 40-60 carbon atoms, exhibiting traces of carotenes, free fatty acids, and free fatty alcohols. The presence of phospholipids was observed in two of them. The third wax presented a higher total wax ester content and physicochemical characteristics (color and thermal behavior) similar to those of commercial sunflower waxes, and was the most efficient organogelator agent, requiring only a small amount of wax (1.5%) to structure high oleic sunflower oil. CONCLUSION: It was verified that sunflower wax could be recovered from oil-tank settlings. A purification method that allowed sunflower wax with similar physicochemical properties to those of commercial waxes to be obtained was also developed. The purified waxes were capable of structuring high oleic sunflower oil. © 2019 Society of Chemical Industry.

Application of magnetized MOF-74 to phthalate esters extraction from Chinese liquor.

In this study, magnetized MOF-74 (Ni) was prepared using an ultrasound-assisted synthesis method. This novel functional magnetic adsorbent was characterized using various techniques. Using the prepared material as adsorbents, a magnetic solid-phase extraction method coupled with high-performance liquid chromatography was proposed for determining four phthalate esters in Chinese liquor samples. The extraction parameters, including solution pH, adsorbent amount, extraction time, and eluent type and volume, were optimized. Under the optimized conditions, proposed method showed good linearity within the range of 1.53-200 µg/L for diphenyl phthalate, 2.03-200 µg/L for butyl benzyl phthalate, 7.02-200 µg/L for diamyl phthalate, and 6.03-200 µg/L for dicyclohexyl phthalate, with correlation coefficients > 0.9944, low limits of detection (0.46-2.10 µg/L, S/N = 3), and good extraction repeatability (relative standard deviations of 3.7%, n = 6). This method was successfully used to analyze phthalate esters in Chinese liquor samples with recoveries of 74.4-104.8%. Two phthalate esters were detected in two samples, both at concentrations that satisfied the Chinese national standard, indicating this method has practical application prospects. The extraction efficiency of this method was also compared with conventional solid-phase extraction using commercial C18 cartridges. The results demonstrated that the proposed magnetic solid-phase extraction is a simple, time-saving, efficient, and low-cost method.

Two new phenylpropanoid esters from Bulbophyllum retusiusculum.

Two new phenylpropanoid esters bobulretulates A (1) and B (2), together with eleven known compounds, were isolated from the whole plants of Bulbophyllum retusiusculum. Their structures were elucidated by means of extensive spectroscopic analysis.

Moose and Caribou as Novel Sources of Functional Lipids: Fatty Acid Esters of Hydroxy Fatty Acids, Diglycerides and Monoacetyldiglycerides.

Fatty acid esters of hydroxy fatty acids (FAHFA), diglycerides (DG) and monoacetyldiglycerides (MAcDG) are gaining interest as functional lipids in pharmaceuticals and functional food formulations for managing and treating metabolic or inflammatory diseases. Herein, we investigated whether the antler and/or meat of two Cervids (moose and caribou) are novel sources of FAHFA, DG and MAcDG. We observed FAHFA present in moose and caribou composed mainly of polyunsaturated families, and that the esterification occurred frequently at the C5-hydroxy fatty acid moiety, most noticeably arachidonic acid 5-hydroxyeicosatrienoic acid (ARA-5-HERA). Moose antler, caribou and moose meat also contained significant levels of both 1,2-DG and 1,3-DG lipids. The 1,3-DG molecular species consisted mainly of 16:0/18:1, 18:0/16:0, and 18:0/18:1. On the other hand, major 1,2-DG species consisted of DG 18:0/18:0, 16:0/16:0 and 18:1/18:1 molecular species with higher levels in the antler compared to the meat. The molecular species composition of MAcDG was very simple and consisted of 14:2/18:2/2:0, 16:0/18:2/2:0, 16:0/18:1/2:0 and 18:0/18:1/2:0 with the first species 14:2/18:2/2:0 predominating in the tip of moose antlers. Increasing access to and knowledge of the presence of these functional lipids in foods will enhance their intake in the diet with potential implications in improving personal and population health.

5-Hydroxyferulic acid methyl ester isolated from wasabi leaves inhibits 3T3-L1 adipocyte differentiation.

To investigate the compounds present in wasabi leaves (Wasabia japonica Matsumura) that inhibit the adipocyte differentiation, activity-guided fractionation was performed on these leaves. 5-Hydroxyferulic acid methyl ester (1: 5-HFA ester), one of the phenylpropanoids, was isolated from wasabi leaves as a compound that inhibits the adipocyte differentiation. Compound 1 suppressed the intracellular lipid accumulation of 3T3-L1 cells without significant cytotoxicity. Gene expression analysis revealed that 1 suppressed the mRNA expression of 2 master regulators of adipocyte differentiation, PPARγ and C/EBPα. Furthermore, 1 downregulated the expression of adipogenesis-related genes, GLUT4, LPL, SREBP-1c, ACC, and FAS. Protein expression analysis revealed that 1 suppressed PPARγ protein expression. Moreover, to investigate the relationship between the structure and activity of inhibiting the adipocyte differentiation, we synthesized 12 kinds of phenylpropanoid analog. Comparison of the activity among 1 and its analogs suggested that the compound containing the substructure that possess a common functional group at the ortho position such as a catechol group exhibits the activity of inhibiting the adipocyte differentiation. Taken together, our findings suggest that 1 from wasabi leaves inhibits adipocyte differentiation via the downregulation of PPARγ.

Isolation, Synthesis and AChE Inhibitory Potential of Some Novel Cinnamyl Esters of Taraxerol, the Major Metabolite of the Mangrove Bruguiera cylindrica.

Systematic chemical screening of the leaves of Bruguiera cylindrica, the tree mangrove of Rhizophoraceae family, afforded five single and pure compounds. The structures of the isolated compounds were established by their spectroscopic data as taraxerol (1), 3ß-(E)-coumaroyltaraxerol (2), 3ß-(Z)-coumaroyltaraxerol (3), ß-sitosterol (4), and eicosanol (5). In view of significant accumulation and interesting biological activities, taraxerol (1) was chemically transformed to synthesize a series of ten cinnamyl esters in very good to excellent yields. The synthesized analogues along with the parent compound were evaluated for their AChE inhibitory potential, BBB permeability and cytotoxicity against Neuro 2A cell line. Among the tested samples, compound 9 showed promising AChE inhibition with significantly low IC50 values, low cytotoxicity and high BBB permeability. Hence, compound 9 can be considered as a lead molecule for further development as potent AChE inhibitor.

New Flavonoid Glucuronate Esters with Anti-inflammatory Activities from Scutellaria regeliana.

Two new flavonoid glucuronate esters, named scuregeliosides A and B (1 and 2), as well as three known ones, chrysin-7-O-ß-d-glucuronic acid methyl ester (3), 5,7,4'-trihydroxyflavone-8-O-ß-d-glucuronic acid methyl ester (4) and apigenin-7-O-ß-d-glucuronic acid ethyl ester (5), were isolated from the ethanolic extract of the whole plant of Scutellaria regeliana. Their chemical structures were elucidated on the basis of comprehensive spectroscopic analyses. Five compounds were screened for anti-inflammatory activity in vitro. As the results, the inhibition rates of release of ß-glucuronidase from rat polymorphonuclear leukocytes were in the range of 42.2 - 47.1% at a concentration of 10 µm.