Separation and Purification of Total Phloroglucinols in Dryopteris crassirhizoma with DM-130 Macroporous Adsorption Resin

To improve the purity of the total phloroglucinols from Dryopteris crassirhizoma extracts, the separation and purification conditions of the total phloroglucinols from Dryopteris crassirhizoma were studied with DM-130 macroporous adsorption resin in this study. Adsorption rate, elution rate and purity of the total phloroglucinols were used as indexes to investigate the adsorption and desorption capacity of the total phloroglucinols with DM-130 macroporous adsorption resin. Through the study, the optimum sample concentration of the total phloroglucinols and maximum sample volume were 1.5 mg·mL^-1 and 7 BV （210 mL）, respectively. The optimum desorption conditions were achieved by using 80% ethanol as desorption solvent at elution flow rate of 1.0 mL·min^-1. The result showed DM-130 macroporous adsorption resin performed effective adsorption and desorption. After purification, the purity of the total phloroglucinols increased by 11.5-fold.

Two New Phloroglucinol Glycosides from Lysidice rhodostega Hance

Two new phloroglucinol glycosides, lysidiciside A (1) and lysidiciside B (2), were isolated from the roots of Lysidice rhodostega Hance. Their structures were determined as 1-[(3-methylbutyryl)phloroglucinol]-β-D- glucopyranoside (1), 1- [(3-methylbutyryl)phloro- glucinol]-β-D-glucopyranosyl-5-O-β-D-glucopyranoside (2) on the basis of chemical and spectral analysis .

无溶剂条件下离子液体催化香豆素衍生物的绿色合成(英文)

Brnsted acidic ionic liquids, namely 2-pyrrolidonium hydrogen sulfate, N-methyl-2-pyrrolidonium hydrogen sulfate, N-methyl-2-pyrrolidonium dihydrogen phosphate, (4-sulfobutyl)tris(4-sulfophenyl)phosphonium hydrogen sulfate, and triphenyl(propyl-3-sulfonyl)phosphonium toluenesulfonate, catalyzed efficient Pechmann condensation of phloroglucinol with β-keto ethyl/ methyl esters. 5,7-Dihydroxy-4-methylcoumarin and 5,7-dihydroxy-4-phenylcoumarin were prepared in good to excellent yields under mild, ambient, and solvent-free conditions. Pyrano[2,3-h] coumarins were then prepared by one-pot three-component reactions of 5,7-dihydroxy-4-subsituted coumarin, malononitrile, and aldehydes in the presence of catalytic amounts of Br nsted basic ionic liquids, namely 2-hydroxyethylammonium formate, 3-hydroxypropanaminium acetate, 1-butyl-3-methylimidazolium hydroxide, pyrrolidinium formate, and pyrrolidinium acetate, under thermal solvent-free conditions. The catalysts are environmentally benign and can be easily prepared, stored, and recovered without significant loss of activity.

Pyrohyperforin, A New Prenylated Phloroglucinol from Hypericum perforatum

Pyrohyperforin, a new prenylated phloroglucinol was isolated from Hypericum perforatum, its structure was established on the basis of spectral data.

Structurally Diverse Polymethylated Phloroglucinol Meroterpenoids from Baeckea frutescens

Phytochemical investigation of the MeOH extract of twigs and leaves of Baeckea frutescens led to the isolation of seven new polymethylated phloroglucinol meroterpenoids(PPMs),named baeckfrutones M-S(1-7).Their structures and absolute configurations were determined by spectroscopic analyses,chiral-phase HPLC analysis,and electronic circular dichroism(ECD)calculations.PPM 1 is a novel meroterpenoid possessing a 6/6/5/3 tetracyclic skeleton in PPMs,whereas 3 and 4 are the first hydroxytasmanone type phloroglucinol-monoterpene hybrids.(+)-2 and 7 displayed potent antiinflammatory activity with IC50 values of 20.86±0.60 and 36.21±1.18 lL,respectively.

Phloroglucinol, a nutraceutical for IR-induced cardiac damage in diabetic rats

Background:Myocardial injury due to ischemia‐reperfusion(IR)is aggravated in diabetes which is associated with oxidative stress.Alleviating oxidative stress via use of antioxidants has been shown to be effective at minimizing myocardial cell death and improving cardiac function.The aim of the present study was to evaluate the cardioprotective effect of phloroglucinol against myocardial reperfusion injury(MRI)in diabetic rats.Methods:Diabetes was induced in female rats with streptozotocin(50 mg/kg).The diabetic rats were orally treated with phloroglucinol(100 and 200 mg/kg daily for 28 days).After treatment the hearts were isolated and mounted on a Langendorff apparatus.The hearts were subjected to 15 minutes of IR to induce myocardial damage.Cardiac functions including heart rate(HR),resting and developed tension,and rate of change of contraction(+dP/dtmax)were recorded.Cardiac injury biomarkers lactate dehydrogenase(LDH)and creatine kinase(CK‐MB)were measured in the heart perfusate.Levels of the antioxidant enzymes reduced glutathione(GSH)and malondialdehyde(MDA)were measured.Hematoxylin and eosin(H&E)staining was also performed.Results:After IR injury,a decrease in HR and+dP/dtmax in hearts from diabetic rat was seen compared to healthy rat hearts,which was reversed by phloroglucinol treatment.Myocardial infarct size,measured by H&E staining,was increased in diabetic rats compared to healthy rats and an increase in the activity of LDH and CK‐MB in the heart perfusate in diabetic rats was decreased by phloroglucinol treatment.An increase in MDA levels and a decrease in levels of antioxidant enzymes were observed in diabetic rats,which was reversed with phloroglucinol treatment.Conclusion:Phloroglucinol treatment has potential therapeutic promise in the treatment of MRI in diabetes.

New Phloroglucinol Glycosides from Hypericum japonicum

Two new phloroglucinol glycosides, 2,6-dihydroxy-3,5-dimethyl-1-isobutyrylbenzene-4-O-beta-D-glucoside and 2,6-dihydroxy-3,5-dimethyl-1-(2-methylbutyryl) benzene-4-O-beta-D-glucoside were isolated from Hypericum japonicum. Their structures were determined by spectroscopic and chemical methods.

Potential of phloroglucinol to improve erectile dysfunction associated with streptozotocin-induced diabetes in rats

Objective: Diabetes is a common metabolic disease with several complications in its patients. Often, people living with diabetes develop erectile dysfunction (ED). The primary aim of this work was to investigate the effect of phloroglucinol in diabetes-induced ED in rats. Methods: Male Wistar rats were given 52 mg/kg of streptozotocin, by intraperitoneal injection, to induce diabetes and ED. Subsequently, animals were grouped into three groups: group 1, diabetic control;group 2, low-dose phloroglucinol (150 mg/kg body weight);and group 3, high-dose phloroglucinol (250 mg/kg body weight). A group of six normal rats served as a normal control. The rats were treated with phloroglucinol for six weeks and then were assessed for treatment effects. Sexual behavior, glycosylated hemoglobin Ale (HbAlc) values, serum testosterone, serum nitric oxide (NO), blood pressure and sperm count were measured after the end of treatment. Results: After a 6-week treatment period, the high dose of phloroglucinol significantly decreased HbAlc values in diabetic rats. Rats treated with phloroglucinol had increased serum testosterone, NO and sperm count. Animals treated with 250 mg/kg phloroglucinol performed similar to normal rats in the sexual behavioral study, suggesting the reversal of complications of ED. Conversely, a decrease in the blood pressure in treated groups was observed. Conclusion: The results highlight the protective effect of phloroglucinol in diabetes-induced ED in rats warranting further studies.

Euphoractone,a cytotoxic meroterpenoid with an unusual entabietane-phloroglucinol skeleton,from Euphorbia fischeriana Steud.

A novel meroterpenoid,euphoractone(1),was isolated from the extracts of the roots of Euphorbia fischeriana Steud.Its structure was determined by spectroscopic methods and X-ray crystallography.1 possesses an unusual ent-abietane-phloroglucinol skeleton.The plausible biosynthetic pathway for 1 was proposed.1 showed inhibitory activities against human lung cancer H23 and H460 cells with the IC_(50)values of 21.07±3.54 and 20.91±4.07 μmol/L.

Carbon nanodots:A metal-free,easy-to-synthesize,and benign emitter for light-emitting electrochemical cells

Light-emitting electrochemical cells(LECs)can be fabricated with cost-efficient printing and coating methods,but a current drawback is that the LEC emitter is commonly either a rare-metal complex or an expensive-to-synthesize conjugated polymer.Here,we address this issue through the pioneering employment of metal-free and facile-to-synthesize carbon nanodots(CNDs)as the emitter in functional LEC devices.Circular-shaped(average diameter=4.4 nm)and hydrophilic CNDs,which exhibit narrow cyan photoluminescence(peak=485 nm,full width at half maximum=30 nm)with a high quantum yield of 77%in dilute ethanol solution,were synthesized with a catalyst-free,one-step solvothermal process using low-cost and benign phloroglucinol as the sole starting material.The propensity of the planar CNDs to form emission-quenching aggregates in the solid state was inhibited by the inclusion of a compatible 2,7-bis(diphenylphosphoryl)-9,9’-spirobifluorene host compound,and we demonstrate that such pristine host-guest CND-LECs turn on to a peak luminance of 118 cd·m^(−2)within 5 s during constant current-density driving at 77 mA·cm^(−2).

Phloroglucinol Protects the Urinary Bladder Via Inhibition of Oxidative Stress and Inflammation in a Rat Model of Cyclophosphamide-induced Interstitial Cystitis

Background： Phloroglucinol plays an important role in oxidative stress and inflammatory responses. The effects of phloroglucinol have been proven in various disease models. The aim of the present study was to investigate the efficacy and possible mechanisms of phloroglucinol in the treatment of interstitial cystitis （IC）. Methods： Thirty-two female Sprague-Dawley （SD） rats were used in this study. IC was induced by intraperitoneal injection of cyclophosphamide （CYP）. Rats were randomly allocated to one of four groups （n = 8 per group）： A control group, which was injected with saline （75 mg/kg; i.p.） instead of CYP on days 1, 4, and 7; a chronic IC group, which was injected with CYP （75 mg/kg; i.p.） on days l, 4, and 7; a high-dose （30 mg/kg） phloroglucinol-treated group; and a low-dose （15 mg/kg） phloroglucinol-treated group. On day 8, the rats in each group underwent cystometrography （CMG）, and the bladders were examined for evidence of oxidative stress and inflammation. Statistical analysis was performed by analysis of variance （ANOVA） followed by least square difference multiple comparison po.s＇t-hoc test. Results： Histological evaluation showed that bladder inflammation in CYP-treated rats was suppressed by phloroglucinol. CMG revealed that the CYP treatment induced overactive bladder in rats that was reversed by phloroglucinol. Up-regulated tumor necrosis factor-or and interleukin-6 expression in the CYP-treated rats were also suppressed in the phloroglucinol treated rats. CYP treatment significantly increased myeloperoxidase activity as well as the decreased activities ofcatalase of the bladder, which was reversed by treatment with phloroglucinol. Conclusions： The application of phloroglucinol suppressed oxidative stress, inflammation, and overactivity in the bladder. This may provide a new treatment strategy for IC.

Effects of solvents and temperature on spherulites of self-assembled phloroglucinol tristearate

Herein,phloroglucinol tristearate(PhgTS)was used to study the crystallization process due to its unique symmetric structure containing a benzene ring and three aliphatic chains.Spherulites of crystallized PhgTS from four solvents under diverse conditions were analyzed in detail and their formation process was studied.Maltese cross is shown by PhgTS spherulites obtained from aprotic solvents via polarized optical microscopy.In comparison,no Maltese cross can be observed from branch-like crystals formed from protic solvents.Independent on the micro-scaled morphology,lamellae were found to be the basic blocks constructing both PhgTS spherulites and branch-like crystals,which were formed predominantly by stacked PhgTS molecules.Although differential characters of the solvents did not affect the formation of lamellas,the solvents played a crucial role in the formation of self-assembled microscaled morphologies.In particular,the morphologies of spherulites were strongly affected by the concentration of PhgTS solutions,surrounding tempera-ture and evaporation rate of solvents.Generally,a higher concentration of PhgTS led to more homogeneous spherulites,a lower evaporation rate resulted in more compact spherulites,and a higher surounding temperature generated preferentially more ring-banded spherulites of PhgTS.

Two new phenolic glycosides isolated from the fruits of Citrus aurantium

The present study was designed to investigate the chemical constituents of the fruit of Citrus aurantium L.. The compounds were isolated and purified by various chromatographic techniques, and their structures were elucidated on the basis of physicochemical properties and spectral data. Two new phenolic glycosides(compounds 1 and 2) were obtained and identified as 1-O-3, 5-dihydroxyphenyl-(6-O-4-hydroxybenzoyl)-β-D-glucopyranoside(1) and 1-O-3, 5-dihydroxyphenyl-(6-O-3-methoxy-4-hydroxy benzoyl)-β-D-glucopyranoside(2), respectively.

Temperature-controlled Cascade Reaction of Phloroglucinoltribenzyl Ether Promoted by Trifluoroacetic Anhydride and Trifluoroacetic Acid

We report the first trifluoroacetic anhydride- and trifluoroacetic acid-promoted cascade reaction with phtoroglucinoltribenzyl ether and carboxylic acid as starting materials. By simply varying the temperature of systems containing the same starting materials, different products were produced in high yields. A three-step consecutive reaction process was also proposed.