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Three new thionic compounds, ()-2-(2-carboxyl-2-hydroxyethylthio)-ferulic acid (), ()-2-methoxy-4-(3-(methylsulfonyl)prop-1-en-1-yl)phenol (), and thiosenkyunolide C (), together with two new aromatic glycosides ( and ) were isolated from the rhizome of Hort. Two known compounds ( and ) were also obtained. Their structures were elucidated based on extensive spectroscopic data (UV, IR, 1D and 2D NMR, and HR-ESI-MS). Furthermore the absolute configurations were established by comparison of their calculated and experimental circular dichroism spectra and by a dimolybdenum tetraacetate [Mo(AcO)]-induced circular dichroism procedure. All compounds were evaluated against lipopolysaccharide (LPS)-induced NO production in BV2 cells, and compounds and showed strong inhibitory activities with IC values of 2.03 and 3.09 µmol/L, respectively (positive control curcumin, IC = 6.17 µmol/L). In addition, compound showed weak proteintyrosine phosphatase-1B (PTP1B) inhibitory activity.
ABSTRACT
Two new compounds, named lyciumlignan D () and lyciumphenyl propanoid A (), along with seven known compounds, were isolated from the root bark of. Their structures were elucidated using spectroscopic data (UV, IR, HR-ESI-MS, 1D and 2D NMR, CD), as well as by comparison with those of the literature. Compounds-were isolated from this genus for the first time. In theassay, compounds,, andexhibited stronger anti-inflammatory effects than the positive control curcumin at a concentration of 10 μmol/L.
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OBJECTIVE:To establish a method for the separation and detection of related substances in baicalein,identify its structure and preliminarily explore the degradation mechanism. METHODS:HPLC was adopted to detect the baicalein,related impurities and forced destruction of degradation products in synthesis process:the column was ES Industries? FluoroSep-RP Phenyl with mobile phase of 0.3%formic acid-methanol-acetonitrile(gradient elution)at a flow rate of 1.0 mL/min,the detection wavelength was 275 nm,the column temperature was 10℃,and the injection volume was 10μL. LC-MS/MS was conducted to identify the related substances and conjecture degradation mechanism:the column was ES Industries? FluoroSep-RP Phenyl with mobile phase of 0.3%formic acid- methanol (gradient elution)at a flow rate of 1.0 mL/min,the detection wavelength was 275 nm,column temperature was 10℃,and the injection volume was 10μL;ion source was electrospray ion source,positive and negative ions,nebulizer pressure was 55 psi and the drying gas flow was 11 L/min,drying gas temperature was 350℃,capillary voltage was 4.0 kV,detection modes were full-scan first-order MS and selective ion full-scan second-order MS,scan ranges were m/z 100-1000 (first-order MS) and 50-500(second-order MS),ionization voltage was 80-135 eV,and the collision energy was 10-30 eV. RESULTS:The linear range of baicalein was 2.4-480μg/mL(r=0.9999);RSDs of precision,stability and reproducibility tests were lower than 2.0%;the limit of quantitation was 7.2 ng,the limit of detection was 2.4 ng. Baicalein was well separated with related substance and 3 major degradation products,the related substance was chemical synthesis precursor wood butterfly;the degradation products were 6,7-quinone derivatives and 7,8-quinone derivatives,which were isomers;oxidative degradation products were benzoic acid phenyl ester derivatives. CONCLUSIONS:The main mechanisms of alkali degradation and oxidative degradation of baicalein include pyran, reciprocal rearrangement and oxidation reaction;the established method is specific and sensitive,and can be used for the detection of related substances in baicalein.
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To investigate the effects of a compound (FF16), compatibility of Rhodiola crenulata, Cordyceps militaris, and Rheum palmatum, on insulin resistance. The results showed that FF16 significantly improved the insulin sensitivity through decreasing AUC values in insulin tolerance tests by 24.1%, 38.5%; reducing the levels of serum insulin by 46.0%, 30.4%, of HOMA-IR by 52.4%, 81.2%; and reversing the lower GIR values by 119.3%, 202.4% in IRF mice and KKAy mice, respectively. In addition, in KKAy mice, the value of whole body insulin sensitivity index (ISWBI) was enhanced by 1.0 times, the abilities of the insulin-induced glucose uptake in liver, adipose and skeletal muscle were enhanced by 1.5, 2.8 and 2.2 times, respectively, in FF16-treated mice comparing with those in model mice. The recombinant human protein tyrosine phosphatase 1B (PTP1B) activity was inhibited by FF16 in vitro with the IC50 value of 0.225 mg x L(-1). The increased PTP1B expression in the liver was also reversed by 45.8% with the administration of FF16 in IRF mice. In conclusion, FF16 could improve insulin resistance by inhibiting the activity of PTP1B.
Subject(s)
Animals , Humans , Male , Mice , Biological Transport , Cordyceps , Chemistry , Drugs, Chinese Herbal , Pharmacology , Therapeutic Uses , Glucose , Metabolism , Insulin , Metabolism , Insulin Resistance , Metabolic Syndrome , Drug Therapy , Metabolism , Mice, Inbred C57BL , Protein Tyrosine Phosphatase, Non-Receptor Type 1 , Rheum , Chemistry , Rhodiola , ChemistryABSTRACT
Thirteen compounds were isolated from the flowers of Chrysanthemum indicum by chromatographic techniques. Their structures were elucidated by spectroscopic methods as acacetin-7-0-beta-D-glucopyranoside (1), luteolin (2), luteolin-7-O-beta-D-glucopyranoside (3), acaciin (4), acacetin 7-0-(6"-0-alpha-L-rhamnopyranosyl)-beta-sophoroside (5), 3-0-caffeoylquinic acid (6), syringaresinol 0-beta-D-glucopyranoside (7), 5,7-dihydroxychromone (8), uracil (9), p-hydroxybenzoic acid (10), 4-0-beta-D-glucopyranosyloxybenzoic acid (11), boscialin (12), blumenol A (13). Compounds 5, 7, 8, 11-13 were isolated from C. indicum for the first time.
Subject(s)
Chrysanthemum , Chemistry , Flowers , Chemistry , Organic ChemicalsABSTRACT
<p><b>OBJECTIVE</b>To study the chemical constituents from the leaves of Sterculia foetida.</p><p><b>METHOD</b>Compounds were isolated by chromatographic techniques. Their structures were elucidated by spectroscopic methods.</p><p><b>RESULT</b>Eight compounds were identified as 5,7,8-tetrahydroxy-4'-methoxyflavone-8-O-beta-D-glucoside (1), 5,7,8-tetrahydroxy-4'-methoxyflavone-7-O-beta-D-glucoside (2), quercetin-3-O-beta-D-glucoside (3), apigenin-6, 8-di-C-beta-D-glucoside (4), puerarin (5), 5,7,8,3'-tetrahydroxy-4'-methoxyflavone (6), 5,7,8-tetrahydroxy-3',4'-dimethoxyflavone (7), 5,7,8-tetrahydroxy-4'-methoxyflavone (8).</p><p><b>CONCLUSION</b>Compounds 1, 2 and 4-8 were isolated from this plant for the first time.</p>
Subject(s)
Plant Extracts , Plant Leaves , Chemistry , Sterculia , ChemistryABSTRACT
<p><b>OBJECTIVE</b>To study the chemical constituents of the bee-collected rape pollen.</p><p><b>METHOD</b>The compounds were isolated by column chromatography on silica gel; Sephadex LH-20 and C18. Their structures were elucidated on the basis of spectral analysis.</p><p><b>RESULT</b>Nine compounds were isolated from the bee-collected rape pollen and the structures of them were kaemferol-3-O-beta-D-glucosyl-(2-->1)-beta-D-glucoside (1), kaemferol-3,4'-di-O-beta-D-glucoside (2), quercetin-3-O-beta-D-glucosyl-(2-->1)-beta-D-glucoside (3), nicotinic acid (4), nicotinamide (5), trans-p-coumaric acid-4-O-beta-D-glucopyranoside (6), kaemferol (7), beta-sitosterol (8) and 5-hydroxymethylfurfural (9).</p><p><b>CONCLUSION</b>Compounds 1-6 were isolated from the bee-collected rape pollen for the first time.</p>
Subject(s)
Animals , Bees , Physiology , Brassica napus , Chemistry , Physiology , Coumaric Acids , Chemistry , Dextrans , Chemistry , Glucosides , Chemistry , Molecular Structure , Plant Extracts , Pharmacology , Pollen , Chemistry , Physiology , Propionates , Sitosterols , ChemistryABSTRACT
Aim To study the chemical constituents of Rhododendron ovatum Planch. Methods The chemical constituents were isolated and purified by silica gel column chromatography and identified on the basis of their physiochemical and spectral data. Results Seven compounds were isolated and identified. Their structures were established as 3,5,7-trihydroxylchromone 3-O-β-D-xylopyranoside (I), taraxerol (II), β-sitosterol (III), betulinic acid (IV), quercetin (V), quercetin-3-O-α-L-rhamnopyranoside (VI), and D-glucose (VII). Conclusion Compound I is a new compound. Compounds II-VII were isolated from this plant for the first time.