No abstract available.
Benzofurans ; Depsides ; Diabetic Nephropathies

OBJECTIVETo study the chemical changes of salvianolic acid B and lithospermic acid of Salvia miltiorrhiza under the conditions of high temperature and high pressure and explore the reaction mechanism.

METHODS. miltiorrhiza extracts, salvianolic acid B and lithospermic acid were put in the reactor under the conditions of high temperature and high pressure (120 degrees C, 0.2 MPa), and the chemical changes and stability was studied.

RESULTSalvianolic acid A was the primary product in salvianolic acid B and lithospermic acid's conversion process, and lithospermic acid was an intermediate in the conversion process of salvianolic acid B. Compared with salvianolic acid B, lithospermic acid could convert into more salvianolic acid A and fewer other products in the same conditions. Salvianolic acid A was not stable under the conditions of high temperature and high pressure, and could sequentially convert into other small molecules.

CONCLUSIONReferring to the chemical conversion of salvianolic acid B and lithospermic acid, a method of large-scale preparation of salvianolic acid A can be developed.

Benzofurans ; analysis ; Caffeic Acids ; analysis ; Depsides ; analysis ; Hot Temperature ; Lactates ; analysis ; Pressure ; Salvia miltiorrhiza ; chemistry

Caffeic acid and its oligomers are the main water-soluble active constituents of the traditional Chinese medicine(TCM) Arnebiae Radix. These compounds possess multiple biological activities such as antimicrobial, antioxidant, cardiovascular protective, liver protective, anti-liver fibrosis, antiviral and anticancer activities. The phenylpropanoid pathway in plants is responsible for the biosynthesis of caffeic acid and its oligomers. Glycosylation can change phenylpropanoid solubility, stability and toxic potential, as well as influencing compartmentalization and biological activity. In view of the important role played by de-glycosylation in the regulation of phenylpropanoid homeostasis, the biosynthesis of caffeic acid and its oligomers are supposed to be under the control of relative UDP-glycosyltransferases(UGTs). Through the data mining of Arnebia euchroma transcriptome, we cloned 15 full-length putative UGT genes. After recombinant expression using the prokaryotic system, the crude enzyme solution of the putative UGTs was examined for the glycosylation activities towards caffeic acid and rosmarinic acid in vitro. AeUGT_01, AeUGT_02, AeUGT_03, AeUGT_04 and AeUGT_10 were able to glycosylate caffeic acid and/or rosmarinic acid resulting in different mono-and/or di-glycosylated products in the UPLC-MS analyses. The characterized UGTs were distantly related to each other and divided into different clades of the phylogenetic tree. Based on the observation that each characterized UGT exhibited substrate or catalytic similarity with the members in their own clade, we supposed the glycosylation abilities towards caffeic acid and/or rosmarinic acid were evolved independently in different clades. The identification of caffeic acid and rosmarinic acid UGTs from A. euchroma could lead to deeper understanding of the caffeic acid oligomers biosynthesis and its regulation. Furthermore, these UGTs might be used for regiospecific glycosylation of caffeic acid and rosmarinic acid to produce bioactive compounds for potential therapeutic applications.
Boraginaceae/genetics* ; Caffeic Acids ; Chromatography, Liquid ; Cinnamates ; Cloning, Molecular ; Depsides ; Glycosyltransferases/genetics* ; Phylogeny ; Tandem Mass Spectrometry

Six new (1-6) and seven known depsidones (7-13) were isolated from the culture of an ant (Monomorium chinensis)-derived fungus Spiromastix sp. MY-1. Their structures were elucidated by extensive spectroscopic analysis including high resolution MS, 1D and 2D NMR data. The new bromide depsidones were obtained through supplementing potassium bromide in the fermentation medium of Spiromastix sp. MY-1. All isolated compounds showed various bioactivities against the tested phytopathogenic bacteria. Particularly, new bromide compound 4, named spiromastixone S, exhibited the strongest activity against Xanthomonas oryzae pv. oryzae with a MIC value of 5.2 μmol·^-1.
Animals ; Anti-Bacterial Agents ; Ants ; Bromides ; Depsides ; Fungi ; Lactones ; Microbial Sensitivity Tests ; Molecular Structure

OBJECTIVETo investigate the chemical constituents of Euphorbia pekinensis roots. METHODS Column and liquid chromatography were used for the isolation of chemical constituents, and their chemical structures were determined using a spectroscopic method.

RESULTS AND CONCLUSIONFour compounds were isolated and identified as ziyu glycoside I (1), 3β-α-L-arabinopyranosyloxyurs-12,19(29)-dien-28-oic acid 28-β-D-glucopyranosyl ester (2), lithospermic acid B (3), and senarguine B (4), which were obtained for the first time from the roots of Euphorbia pekinensis.

Benzofurans ; chemistry ; isolation & purification ; Depsides ; chemistry ; isolation & purification ; Euphorbia ; chemistry ; Glycosides ; chemistry ; isolation & purification ; Plant Roots ; chemistry

To improve the quality control specification of Perillae Fructus, the identification methods and assay were developed. Rosmarinic acid, luteolin and apigenin in the sample were identified by TLC. The content of rosmarinic acid was determined by HPLC. The linear calibration curve of rosmarinic acid was obtained in the ranges of 19.4-194.2 g x L(-1) (R2 = 0.9999). The arerage coveriy (n=9) for the assay was 99.8% (RSD 3.6%). The established methods are accuracy, sensitivity and reproducible, and can be used for the quality control of Perillae Fructus.
Apigenin ; analysis ; Chromatography, High Pressure Liquid ; Chromatography, Thin Layer ; Cinnamates ; analysis ; Depsides ; analysis ; Luteolin ; analysis ; Perilla frutescens ; chemistry ; Reproducibility of Results

OBJECTIVETo develop a HPLC method for simultaneous determination of caffeic acid, rosmarinic acid, oleanolic acid and ursolic acid in Spica Prunellae.

METHODAfter ultrasonic extraction with 75% ethanol solution containing 1% formic acid, the ethanol-extract of Spica Prunellae was analyzed on an Elite SinoChrom ODS-AP column using gradient elution of 0.01% phosphoric acid (A) and acetonitrile (B) at a flow rate of 0.9-1.0 mL x min(-1). A wavelength switch program was used for detection at 330 nm (0-33 min) and 203 nm (33-40 min). The column temperature was set at 20 degrees C and injection volume was 50 microL.

RESULTThe calibration curves of all analytes were linear. The average recoveries were 93.7%-105.2% with RSDs not more than 4.5%. The contents of caffeic acid, rosmarinic acid, ursolic acid and oleanolic acid in Spica Prunellae were 0.0401-0.0968, 0.99-2.57, 0.243-0.556, 4.06-8.13 mg x g(-1), respectively.

CONCLUSIONThe described method is sensitive, convenient and accurate, and is suitable for the simultaneous determination of caffeic acid, rosmarinic acid, oleanolic acid and ursolic acid in Spica Prunellae.

Caffeic Acids ; analysis ; Calibration ; Chromatography, High Pressure Liquid ; methods ; Cinnamates ; analysis ; Depsides ; analysis ; Oleanolic Acid ; analysis ; Prunella ; chemistry ; Triterpenes ; analysis

The difference between three representative components of total salvianolic acids in pharmacodynamic activity were compared by three different pharmacological experiments: HUVECs oxidative damage experiment, 4 items of blood coagulation in vitro experiment in rabbits and experimental myocardial ischemia in rats. And the effects of contribution rate of each component were calculated by multi index comprehensive evaluation method based on CRITIC weights. The contribution rates of salvianolic acid B, rosmarinic acid and Danshensu were 28.85%, 30.11%, 41.04%. Apparent oil/water partition coefficient of each representative components of total salvianolic acids in n-octyl alcohol-buffer was tested and the total salvianolic acid components were characterized based on a combination of the approach of self-defined weighting coefficient with effects of contribution rate. Apparent oil/water partition coefficient of total salvianolic acids was 0.32, 1.06, 0.89, 0.98, 0.90, 0.13, 0.02, 0.20, 0.56 when in octanol-water/pH 1.2 dilute hydrochloric acid solution/ pH 2.0, 2.5, 5.0, 5.8, 6.8, 7.4, 7.8 phosphate buffer solution. It provides a certain reference for the characterization of components.
Animals ; Benzofurans ; chemistry ; pharmacology ; Cinnamates ; chemistry ; pharmacology ; Depsides ; chemistry ; pharmacology ; Lactates ; chemistry ; pharmacology ; Male ; Rabbits ; Rats ; Rats, Sprague-Dawley ; Solubility

OBJECTIVE: To evaluate the effect of rosmarinic acid (RA) on mitophagy and hypertrophy of cardiomyocytes exposed to high glucose (HG). METHODS: Rat cardiomyocytes (H9c2) exposed to HG (25 mmol/L) were treated with 50 μmol/L RA or with both RA treatment and Parkin siRNA transfection, with the cells cultured in normal glucose (5.5 mmol/L) and HG as the controls. The expressions of PINK1, Parkin and LC3II/LC3I in the cells were detected by Western blotting. The formation of mitochondrial autophagosomes was observed by transmission electron microscope. Flow cytometry was employed to detect the level of reactive oxygen species (ROS) and apoptotic rate of the cells. The activities of respiratory chain complex enzymes were measured by spectrophotometry. Fluorescence enzyme labeling and RESULTS: RA treatment significantly increased the expression levels of PINK1, Parkin and LC3-II/I ( CONCLUSIONS RA can protect rat cardiomyocytes against oxidative stress injury and cardiomyocyte hypertrophy induced by HG by activating Parkin-mediated mitophagy.
Animals ; Cinnamates ; Depsides ; Glucose ; Hypertrophy ; Mitophagy ; Myocytes, Cardiac ; Protein Kinases ; Rats ; Reactive Oxygen Species ; Ubiquitin-Protein Ligases/genetics*

Rosmarinic acid,a hydrosoluble polyphenolic hydroxyl compound,is the active ingredient in such traditional Chinese medicines as Menthae Haplocalycis Herba,Salviae Miltiorrhizae Radix et Rhizoma,Rosemary,Perillae Folium. Because of its good anti-inflammatory,anti-oxidant and anti-tumor effects,it is widely used in food,medicine and other fields. However,the metabolic process and metabolites of rosmarinic acid in vivo have not been completely defined. In this study,an efficient method of ultra-high performance liquid chromatography combined with linear ion trap-Orbitrap(UHPLC-LTQ-Orbitrap) mass spectrometer was used to analyze the metabolites in vivo of rosmarinic acid in rats. Plasma,urine and feces samples were collected after oral administration of rosmarinic acid. After biological samples were processed by solid phase extraction,Acquity UPLC  BEH C18 column(2. 1 mm × 100 mm,1. 7 μm) was used with 0. 1% formic acid(A)-acetonitrile(B) solution as the mobile phase at the speed of 0. 30 m L·min-1 and temperature of 35 ℃ under gradient conditions. The plasma,urine,feces and the blank samples were then analyzed by ESI-LTQ-Orbitrap under both negative and positive ion modes. Based on the accurate mass measurement(<5),MS/MS fragmentation patterns,standards and literatures,a total of 36 metabolites were screened out and identified in the biological samples collected from rats after intragastric administration. Three were identified 3 from rat plasma,31 from urine,and 7 from feces. The main metabolic pathways of rosmarinic acid in rats can be divided into five parts. Rosmarinic acid were first decomposed into small molecules,such as trans-caffeic acid,coumaric acid,m-hydroxybenzoic acid and Danshensu,which were followed by sulfation,methylation,glucuronic acid conjugation and glucose conjugation. The results showed that UHPLC-LTQ-Orbitrap mass spectrometer could be used to analyze the metabolism of rosmarinic acid in rats,and provide reference for further studies on toxicology,pharmacodynamics and secondary development of Chinese medicine.
Animals ; Chromatography, High Pressure Liquid ; Cinnamates/metabolism* ; Depsides/metabolism* ; Drugs, Chinese Herbal/metabolism* ; Rats ; Tandem Mass Spectrometry ; Rosmarinic Acid