(±)-Talapyrones A-F (1-6), six pairs of dimeric polyketide enantiomers featuring unusual 6/6/6 and 6/6/6/5 ring systems, were isolated from the fungus Talaromyces adpressus. Their structures were determined by spectroscopic analysis and HR-ESI-MS data, and their absolute configurations were elucidated using a modified Mosher's method and electronic circular dichroism (ECD) calculations. (±)-Talapyrones A-F (1-6) possess a 6/6/6 tricyclic skeleton, presumably formed through a Michael addition reaction between one molecule of α-pyrone derivative and one molecule of C₈ poly-β-keto chain. In addition, compounds 2/3 and 4/5 are two pairs of C-18 epimers, respectively. Putative biosynthetic pathways of 1-6 were discussed.
Polyketides/isolation & purification* ; Talaromyces/chemistry* ; Stereoisomerism ; Molecular Structure ; Circular Dichroism ; Pyrones/chemistry*

Lomatogonium rotatum (L.) Fries, Gentianopsis barbata (Froel) Ma, and Gentianella acuta (Michx.) Hulten, the three kinds of Digeda-species Mongolian medicinal materials belonging to the family Gentianaceae, bad been widely used for the treatment of liver diseases. To analyze comparatively the content of swertiamarin and swertisin among these three kinds of Digeda-species Mongolian medicinal materials. HPLC method was applied for qualitative and quantitative analysis of swertiamarin and swertisin. The Phenomenex C18 (4.6 mm x 250 mm, 5 μm) was used, chromatographic methanol and water as mobile phase, the flow rate was 1.5 mL x min(-1) with UV detected at 237 nm, column oven temperature was 25 degrees C. Results showed that the contents of swertiamarin and swertisin were closely related the different species and producing areas. The content range of swertiamarin in L. rotatum from different habitats was 1.73% - 2.72%, 0.43% - 0.96% for the swertisin content; the content of swertiamarin in G. barbata from Alxa Left Banner was 0.38%, and the content of swertiamarin and swertisin in G. barbata from the others habitats and G. Acuta from different habitats were all detected qualitatively. The contents of swertiamarin and swertisin among these medicinal plants showed a significant difference due to the different species and producing areas. As a consequence, these medicinal plants should not be put together for clinical applications.
Apigenin ; analysis ; Chromatography, High Pressure Liquid ; Gentianaceae ; chemistry ; classification ; Gentianella ; chemistry ; classification ; Iridoid Glucosides ; analysis ; Medicine, Mongolian Traditional ; Mongolia ; Plant Extracts ; analysis ; Pyrones ; analysis

OBJECTIVETo develop an HPLC method for simultaneous determination of swertiamarin, gentiopicroside, sweroside, mangiferin, erythrocentaurin, and to detect these five constituents in eight Qingyedans derived from Swertia mileensis, S. cincta, S. patens, S. punicea, S. delavayi, S. nervosa, S. macrosperma and S. yunnanensis.

METHODThe separation was carried out on a Thermo BDS Hypersil C18 (4. 6 mm x 250 mm, 5 microm) column eluted with mobile phase of water containing 0. 1% phosphoric acid and methanol (B) in gradient program (0-10 min, 18%-20% B; 10-30 min, 20%-35% B; 30-35 min, 35%-60% B). The column temperature was 32 degrees C , and the detection wavelength was set at 250, 260, 225 nm. The flow rate was 0. 7 mL . min-1 from 0 to 30 min, and be increased to 1. 0 mL . min-1 in 35 min.

RESULTThe five compounds were well separated. The linear response ranges of swertiamarin, gentiopicroside, sweroside, mangiferin, erythrocentaurin were 0. 072-13. 39, 0. 1204. 518, 0. 060-5. 050, 0. 025-1. 518, and 0. 031-0. 210 microg, respectively. The mean recoveries of five compounds were 97.03% -102. 7% (RSD 1. 8% -6.2% ). There are swertiamarin, gentiopicroside and sweroside in most samples, and mangiferin in half samples. But erythrocentaurin was only detected in a few samples. The contents of five compounds were different in different samples. The contents of swertiamarin in S. mileensis, S. patens, S. yunnanensis and S. delavayi are up to 34. 47-118.05 mg . g-1, the contents of gentiopicroside are up to 25. 91 mg . g-1 in S. cincta. In S. puncea all contents of swertiamarin, gentiopicroside, sweroside and mangiferin are higher, especially the content of sweroside. There are Xiao-Qingyedans and Da-Qingyedans called in markets, and they can be identified by the contents of swertiamarin, gentiopicroside and sweroside. S. punicea can be identified by the content of sweroside, and the ratio gentiopicroside/total content can be used for identification of S. cincta from other seven Qingyedan species.

CONCLUSIONThe method was certified to be accurate and reliable and can be used for identification and quality evaluation of traditional Chinese medicine Qingyedan derived from Swertia species.

Chromatography, High Pressure Liquid ; methods ; Iridoid Glucosides ; analysis ; Pyrones ; analysis ; Swertia ; chemistry

OBJECTIVETo establish a method for quickly investigating the absorption ingredients which could be used as the index of quality control of Gentianae Radix et Rhizoma.

METHODThe absorption ingredients of Gentianae Radix et Rhizoma were investigated by using the model of in vitro everted intestinal sac (VEIS). The intestinal sac liquors of jejunum and ileum were collected at 6 intervals (15, 30, 45, 60, 90, 120 min) and gentiopicroside, loganin acid, swertiamarin and sweroside were detected by HPLC as the representative marker. The accumulative absorption quantity of gentiopicroside, loganin acid, swertiamarin and sweroside were calculated, respectively.

RESULTSix components could be detected in intestinal sac. In different concentrations of Gentianae Radix et Rhizoma, gentiopicroside and swertiamarin in various intestinal sections were the linear absorption (R2 > 0.9), conformed to zero order absorption rate. In jejunum the constant of absorption rate (Ka) of gentiopicroside and swertiamarin increased with the raised dosage of Gentianae Radix et Rhizoma (P < 0.05), which indicated a passive absorption manner, and the value of Ka of high and middle dosage of those in ileum were higher than that of low dosage, and the difference of Ka between high and middle dosage were not significant, which indicated a positive absorption manner. The Ka of high and middle dosage of sweroside in ileum and jejunum were higher than that of low dosage (P < 0.05), and the difference of Ka between high and middle dosage were not significant, which indicated a positive absorption manner. The Ka of loganin acid in jejunum and ileum increased along with the raised dosage of Gentianae Radix et Rhizoma (P < 0.05), which indicated a passive absorption manner.

CONCLUSIONSEMAC could be used as a tool to investigate the absorption ingredients of Gentianae Radix et Rhizoma. Drug in intestine sac was selective, and the absorption part of intestine was also different.

Absorption ; Animals ; Chromatography, High Pressure Liquid ; Drugs, Chinese Herbal ; pharmacokinetics ; Gentiana ; chemistry ; Ileum ; metabolism ; Iridoid Glucosides ; pharmacokinetics ; Jejunum ; metabolism ; Male ; Pyrones ; pharmacokinetics ; Rats ; Rats, Wistar

OBJECTIVETo study the rubrofusarin glucosides from whole plants of Berchemia polyphylla var. leioclada, and their scavenging activities for 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical.

METHODThe chemical constituents were isolated and purified via repeated silica gel and Sephadex LH-20 column chromatography. Their structures were elucidated by spectral analysis and the compounds were tested for their scavenging activities on DPPH radical.

RESULTThree rubrofusarin glucosides compounds were isolated and identified as rubrofusarin-6-O-beta-D-glucopyranoside (1), rubrofusarin-6-O-beta-D-(6'-O-acetyl) glucopyranoside (2), rubrofusarin-6-O-alpha-L-rhamnosyl-(1-6) -O-beta-D-glucopyranside (3). Three isolated compounds showed strong scavenging activities on DPPH radical, the concentration of half elimination ratio( micromol x L(-1)) of VitC and Compounds 1-3 were 18.2, 40.5, 23.3 and 13.6, respectively.

CONCLUSIONCompounds 1-3 were isolated from this plant for the first time and compound 2 was a new compound. They showed significant antioxidant activity, and the scavenging activity of compound 3 was a little stronger than that of VitC.

Biphenyl Compounds ; metabolism ; Free Radical Scavengers ; chemistry ; pharmacology ; Glucosides ; chemistry ; pharmacology ; Nuclear Magnetic Resonance, Biomolecular ; Picrates ; metabolism ; Pyrones ; chemistry ; pharmacology ; Rhamnaceae ; chemistry

OBJECTIVETo develop an HPLC method for the quantification of six active components in three species (Swertia davidi, S. nervosa and S. mussotii) .

METHODThe determination was performed on a Hypersil BDS colunm (4. 6 mm x 200 mm, 5 microm). Acetonitrile and 0.5% phosphoric acid solution were used as the mobile phases with a gradient elution. The flow rate was 1.0 mL x min(-1). The UV detection wavelength was at 240, 274, 325 and 334 nm. The column oven temperature was at 25 degrees C.

RESULTSix components were separated commendably in 60 minutes. The calibration curves of swertiamarin, gentiopicroside, norswertianolin, swertianolin, demethylbellidifolin and bellidifolin were in good linearity over the range of 0.520-20.8, 0.202-8.06, 0.107-4.28, 0.097-3.86, 0.094-3.77, 0.101-4.02 microg, respectively (r = 0.999 9). The average recoveries were 98.7%, 98.1%, 98.3%, 98.8%, 98.1% and 98.6%, respectively, and the RSD were less than 3.0% (n = 6).

CONCLUSIONThe method is accurate,simple and reproducible, and can be used to control the quality of Swertia.

Chromatography, High Pressure Liquid ; instrumentation ; methods ; Drugs, Chinese Herbal ; analysis ; Glucosides ; analysis ; Iridoid Glucosides ; Iridoids ; analysis ; Pyrones ; analysis ; Swertia ; chemistry ; Xanthones ; analysis

To study the chemical constituents of Sparganium stoleniferum Buch. -Ham, various chromatographic techniques were used to separate and purify the chemical constituents. Their physicochemical properties and spectral data were used to elucidate the structures. Five compounds have been isolated by using silica gel column chromatography. They are beta-sitosterol plamitate (I), SanLeng diphenyllactone (II), SanLeng diphenylacetypene (III), 6,7,10-trihydroxy-8-octadecenoic acid (IV) and daucosterol plamitate (V). Compound II, III are two new compounds.
Benzoates ; chemistry ; isolation & purification ; Magnoliopsida ; chemistry ; Molecular Structure ; Plant Tubers ; chemistry ; Plants, Medicinal ; chemistry ; Pyrones ; chemistry ; isolation & purification ; Sitosterols ; chemistry ; isolation & purification ; Xanthones ; chemistry ; isolation & purification

OBJECTIVETo isolate and identify the chemical constituents of 95% alcohol extract from Swertia delavayi.

METHODThe compounds were isolated and purified by column chromatogrphy and their structures were identified by the physicochemical properties and spectral analyses.

RESULTSeven compounds were isolated and identified as oleanolic acid (1), gentiopcroside (2), swertiamarin (3), daucosterol (4), swertiadecoraxanthone-II (5), isovitexin (6), isoorientin (7).

CONCLUSIONCompounds 2-7 were isolated from S. delavayi for the first time. While the compound 6 was firstly reported from the genus Swertia.

Apigenin ; chemistry ; Glucosides ; chemistry ; Iridoid Glucosides ; Iridoids ; chemistry ; Luteolin ; chemistry ; Magnetic Resonance Spectroscopy ; Oleanolic Acid ; chemistry ; Pyrones ; chemistry ; Sitosterols ; chemistry ; Spectrometry, Mass, Electrospray Ionization ; Swertia ; chemistry

OBJECTIVETo establish a RP-HPLC method for the determination of swertiamarin, sweroside, gentiopicrin and oleanolic acid in different parts of Swertia pseudochinesis.

METHODA Zorbax SB-C18 (4.6 mm x 250 mm, 5 microm) column was used with acetonitrile-water (10:90) and methnol-water(86:14) at detection wavelengths of 238 nm, 246 nm, 274 nm and 207 nm for swertiamarin, sweroside, gentiopicrin and oleanolic acid respectively. The flow rate was 1.0 mL x min(-1) and the column temperature was 25 degrees C.

RESULTAll of the compounds were based--isolated. The linear ranges of swertiamarin, sweroside, gentiopicrin and oleanolic acid were 0.068 9-0.344 4(r = 0.999 2) , 0.001 1-0.014 0 (r2 = 0. 999 8), 0.001 1-0.013 4 (r2 = 0.999 9) and 0.001 1-0.008 8 mg x mL(-1) (r2 = 0. 999 6), respectively.

CONCLUSIONThe method is simple and accurate, which can be used for quality control of S. pseudochinesis.

Chromatography, High Pressure Liquid ; methods ; Flowers ; chemistry ; Glucosides ; analysis ; Iridoid Glucosides ; Iridoids ; analysis ; Oleanolic Acid ; analysis ; Plant Leaves ; chemistry ; Plant Roots ; chemistry ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry ; Pyrones ; analysis ; Reproducibility of Results ; Swertia ; chemistry ; Triterpenes ; analysis

AIMTo seek for new components as BACE inhibitors from Aloe arborescens.

METHODSThe chemical constituents were isolated by chromatographic methods and their structures were elucidated on the basis of spectral analysis.

RESULTSEight compounds were isolated and their structures identified as 6'-O-isobutyryl aloenin A (1), aloenin A (2), aloe-emodin (3), (E)-2-acetonyl-8-(2'-O-feruloxyl)-beta-D-glucopyranosyl-7-methoxy-5-methyl-chromone (4), 7-O-methylaloeresin A (5), babarloin A (6), elgonica-dimer A (7), and elgonica-dimer B (8), separately.

CONCLUSIONCompound 1 is a new compound, and compound 4 was isolated from A. arborescens for the first time. Pharmacological tests indicated that 2, 4, 5 and 6 have moderate inhibitory active on BACE.

Aloe ; chemistry ; Amyloid Precursor Protein Secretases ; antagonists & inhibitors ; metabolism ; Anthraquinones ; chemistry ; isolation & purification ; pharmacology ; Aspartic Acid Endopeptidases ; antagonists & inhibitors ; metabolism ; Chromones ; chemistry ; isolation & purification ; pharmacology ; Enzyme Inhibitors ; chemistry ; isolation & purification ; pharmacology ; Glucosides ; chemistry ; isolation & purification ; pharmacology ; Humans ; Molecular Conformation ; Molecular Structure ; Plant Components, Aerial ; chemistry ; Plant Extracts ; chemistry ; isolation & purification ; pharmacology ; Plants, Medicinal ; chemistry ; Pyrones ; chemistry ; isolation & purification ; pharmacology