ABSTRACT
Seven lignans and eight phenylpropanoids, including one new lignan, 7S,8R,8'R-5,5'-dimethoxyariciresinol-4-O-ß-D-glucopyranoside (1), were isolated from the liquid juice of Phyllostachys edulis. Their structures were established by extensive spectroscopic analyses. The absolute configuration of the new compound was determined by comparing its experimental electronic circular dichroism (ECD) spectra with calculated ECD spectra. All compounds were evaluated for their anti-inflammatory activity and xanthine oxidase inhibitor activity, and the results showed that compound 9 exhibited a moderate activity in these two bioassays. In addition, all the compounds can be detected in health panda faeces by LC-MS.
Subject(s)
Lignans , Poaceae/chemistry , Propionates/pharmacology , Animals , Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/pharmacology , Circular Dichroism , Feces/chemistry , Lignans/isolation & purification , Lignans/pharmacology , Mass Spectrometry , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Plant Extracts/chemistry , Propionates/isolation & purification , Ursidae , Xanthine Oxidase/antagonists & inhibitorsABSTRACT
Chinese chive (jiu cai) is a popular vegetable in China and has a unique flavour and aroma. The molecular basis of the characteristic fragrance and nutritional properties of Chinese chive has not been previously identified. Sequential extractions in a series of solvents and high-performance liquid chromatography were used to isolate 40 compounds from Chinese chive. The compounds were identified based on high-resolution electrospray ionization mass spectra, 1D and 2D nuclear magnetic resonance techniques, and circular dichroism spectra. Eight novel compounds were identified-four new pyrazines, which have distinctive flavour; one new lignan; and three new flavonoids-together with 32 known compounds. Several of these compounds have potential applications as health-promoting dietary supplements, food additives, or seasonings. Additionally, the volatile organic compounds in fresh and steamed Chinese chive were compared, and the toxicological activity of extracts from fresh and steamed Chinese chive was tested in normal rat liver (IAR20) and kidney (NRK) cells. The results showed that Chinese chive is toxic to liver and kidney cells when fresh, but is safe after heating. This could explain why it is traditional to eat cooked Chinese chive. A possible metabolic rule regarding pyrazines is postulated based on this data, and a human metabolic pathway is suggested for two of the novel compounds which have the highest amount of Chinese chive extracts.
Subject(s)
Chive/chemistry , Cooking , Crops, Agricultural/chemistry , Flavonoids/isolation & purification , Lignin/isolation & purification , Plant Extracts/isolation & purification , Pyrazines/isolation & purification , Animals , Cell Line , Cell Survival/drug effects , Chromatography, High Pressure Liquid , Dietary Supplements , Flavonoids/chemistry , Food Additives , Kidney/cytology , Kidney/drug effects , Kidney/metabolism , Lignin/chemistry , Liver/cytology , Liver/drug effects , Liver/metabolism , Odorants , Plant Extracts/toxicity , Pyrazines/chemistry , Rats , Spectrum Analysis/methods , VolatilizationABSTRACT
One new compound, 2H, 3H-cyclopent[b] furo [2',3':4,5] naphtho [2,4-d] heptlactone-[3,7] furan-6aceticacid, 3-(acetyloxy)-8-(3-furyl)-2a, 4a, 4b, 4c,5,5a, 6, 6a, 8, 9,9a, 10a,10b-13 hydrogen-2a,5a,6a,5-tetramethyl-3-[[(2E)-2-methyl-1-oxo-2-butenyl]oxy]-methyl ester, named azadirachta R (1), along with 10 known ones, Azadirachta A, AZ-B, AZ-D, AZ-H, AZ-I, nimbin, deacetylnimbin, salannin, deacetylsalannin and azadiradione were isolated from the crude extracts of neem (Azadirachta indica A. Juss) seeds, which were determined by UV, IR, HR-ESI-MS and NMR data analyses. According to the in vitro antibacterial activity experimental results, this compound showed good antibacterial activity to two bacteria, the minimum inhibitory concentration and the minimum bactericidal concentration of compound 1 to two kinds of bacteria are 50 and 25 mg/L, respectively, which were determined by resazurin colour-micro-dilution method. The experimental results provide a theoretical basis for the comprehensive utilisation of azadirachtin compounds in the future.
Subject(s)
Anti-Bacterial Agents/pharmacology , Azadirachta/chemistry , Limonins/chemistry , Anti-Bacterial Agents/chemistry , Drug Evaluation, Preclinical/methods , Limonene , Limonins/isolation & purification , Limonins/pharmacology , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Molecular Structure , Plant Extracts/chemistry , Seeds/chemistry , Triterpenes/chemistry , Triterpenes/isolation & purificationABSTRACT
Bamboo shoots are a delicacy in Asia. Two novel compounds, adenine-(1'R,2'R,3'R)-cyclic butanetetraol carbonate (16) and (-)-(7R,8S)-(4-hydroxy-3-methoxyphenylglycerol 9-O-ß-D-[6-O-4-hydroxy-3-methoxybenzoyl])-glucopyranoside (20), together with 12 known nucleosides (1-12), 3 amino acids (13-15), ß-carboline (17), and 2 megastigmane glycosides (18, 19) were isolated from bamboo shoots (Phyllostachys pubescens). Their structures and absolute configurations were rigorously determined by detailed spectroscopic analysis, and the composition of carbohydrates in bamboo shoots was qualitatively detected and quantitatively analyzed with ion chromatography. A simple, rapid, sensitive, and accurate HPLC-UV analysis was built for routine edible quality control of bamboo shoots, and 12 major components of bamboo shoots were quantitatively analyzed. The major chemical constituents of bamboo shoots were determined to be carbohydrates, amino acids, and nucleotides. These findings are correctives to the usual view of bamboo shoots chemical composition, and the previous research reports about the chemical composition of bamboo shoots may have taken the aromatic amino acids and nucleotides for flavonoids and phenolic acids.
Subject(s)
Drugs, Chinese Herbal/chemistry , Glycosides/isolation & purification , Poaceae/chemistry , Amino Acids/analysis , Carbohydrates/analysis , Carbolines/analysis , Chromatography, High Pressure Liquid , Cyclohexanones/analysis , Glucosides/analysis , Glycosides/chemistry , Molecular Structure , Norisoprenoids/analysis , Nuclear Magnetic Resonance, Biomolecular , Nucleotides/analysis , StereoisomerismABSTRACT
Obesity is a medical condition of excess body fat negatively influencing morbidity and mortality via non-communicable disease risks. Adipogenesis, the process in which preadipocytes differentiate into adipocytes, plays a pivotal role in obesity. Our previous study proved that tannic acid (TA) showed anti-adipogenesis effect in 3T3-L1 preadipocytes. However, the precise mechanism involved in the inhibition in adipocytes differentiation by TA is unclear, and thus this is the subject of the present investigation. In this study, we determined the effect of TA on different stages of 3T3-L1 preadipocytes differentiation, and found that when treating in the early stage of differentiation, TA reduced lipid accumulation significantly. However, TA did not reduce lipid accumulation when treating in mid- and late-stages of adipocyte differentiation. To further study which gene TA had an impact on in the early stage of differentiation, we identified a number of genes associated with lipid metabolism. The results showed that compared to the control group, the mRNA levels of FAS, C/EBPα, and PPARγ were significantly decreased (p < 0.05), whereas the mRNA levels of adipsin, ap2 were increased (p < 0.05). However, TA had no effect on mRNA levels of ACC1 and ACC2. Western blot results showed that TA down-regulated the expression of PPARγ, which is a major factor in preadipocyte differentiation. In addition, TA did not affect the PI3 K/AKT pathway. These results indicate that the anti-adipogenesis effect of TA involves down-regulation of PPARγ in the early stage of 3T3-L1 preadipocyte differentiation. Some potential limitations of this study should be considered. All the results in this study were based on cell experiments. However, the human bioavailability of TA is not clear. In the present study, the concentration of TA was 5 µM; therefore, there were concerns about whether oral intake of TA could reach the effective concentrations. This important point needs to be clarified in vivo.
Subject(s)
Adipocytes, White/metabolism , Adipogenesis , Anti-Obesity Agents/metabolism , Dietary Supplements , Down-Regulation , PPAR gamma/antagonists & inhibitors , Tannins/metabolism , 3T3-L1 Cells , Adipocytes, White/cytology , Animals , CCAAT-Enhancer-Binding Protein-alpha/antagonists & inhibitors , CCAAT-Enhancer-Binding Protein-alpha/genetics , CCAAT-Enhancer-Binding Protein-alpha/metabolism , Cell Proliferation , Complement Factor D/chemistry , Complement Factor D/genetics , Complement Factor D/metabolism , Fatty Acid Synthases/antagonists & inhibitors , Fatty Acid Synthases/genetics , Fatty Acid Synthases/metabolism , Fatty Acid-Binding Proteins/agonists , Fatty Acid-Binding Proteins/genetics , Fatty Acid-Binding Proteins/metabolism , Kinetics , Lipid Metabolism , Mice , PPAR gamma/genetics , PPAR gamma/metabolism , RNA, Messenger/metabolism , Up-RegulationABSTRACT
Two new compounds, xylitol 1-O-(6'-O-p-hydroxylbenzoyl)-glucopyranoside (1) and bambulignan B (2), together with three known ones gastrodin (3), glucovanillin (4), and rel-(7S,7'R,8R,8'S)-4,4'-dihydroxy-3,3',5,5'-tetramethoxy-7,7'-epoxyligna-9,9'-diol-9(or)9'-O-ß-glucopyranoside (5), were isolated from the 95% EtOH extract of the dry leaves of Pleioblastus amarus (Keng) keng f. Their structures were determined by UV, IR, HR-ESI-MS, CD, and 1D and 2D NMR data analyses as well as GC experiments.
Subject(s)
Drugs, Chinese Herbal/isolation & purification , Glucosides/isolation & purification , Lignans/isolation & purification , Poaceae/chemistry , Xylitol/analogs & derivatives , Xylitol/isolation & purification , Drugs, Chinese Herbal/chemistry , Glucosides/chemistry , Lignans/chemistry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Leaves/chemistry , Xylitol/chemistryABSTRACT
By studying on absorption spectrum of red compound coming from the reaction system of Fe2+ and 1, 10-phenanthroline and the capacity of antioxidant TBHQ and bamboo leaf extract for scavenging hydroxyl free radical, some results were drawn as follows: the determining wavelength of bamboo leaf extract for scavenging hydroxyl free radical by spectrophotometric method is 509.1 nm, and IC50 (the value of antioxidant concentration at scavenging half of hydroxyl free radical)was used as the index to evaluate scavenging capacity. The determined IC50 values were TBHQ (0.040), M20 (0.378), M40 (0.323), M60 (0.334), and bamboo leaf extract could be used as natural antioxidant.