Acrolein, known as one of the most common reactive carbonyl species, is a toxic small molecule affecting human health in daily life. This study is focused on the scavenging abilities and mechanism of ferulic acid and some other phenolic acids against acrolein. Among the 13 phenolic compounds investigated, ferulic acid was found to have the highest efficiency in scavenging acrolein under physiological conditions. Ferulic acid remained at (3.04±1.89)% and acrolein remained at (29.51±4.44)% after being incubated with each other for 24 h. The molecular mechanism of the detoxifying process was also studied. Detoxifying products, namely 2-methoxy-4-vinylphenol (product 21) and 5-(4-hydroxy-3-methoxyphenyl)pent-4-enal (product 22), were identified though nuclear magnetic resonance (NMR) and gas chromatography-mass spectrometry (GC-MS), after the scavenging process. Ferulic acid showed significant activity in scavenging acrolein under physiological conditions. This study indicates a new method for inhibiting damage from acrolein.
Acrolein/toxicity* ; Coumaric Acids/pharmacology* ; Glutathione/physiology* ; Hydroxybenzoates/pharmacology* ; Magnetic Resonance Spectroscopy ; Structure-Activity Relationship

OBJECTIVETo study the anti-complementary phenolic acids from Lonicera japonica.

METHODThe anti-complementary activity-directed isolation was carried out with the hemolysis test as guide. All isolation was evaluated for their in vitro anti-complementary activities. The structures were identified by various spectroscopic data including ESI-MS, 1H-NMR, 13C-NMR data.

RESULTFourteen compounds were isolated from the EtOAc fraction of L. japonica extracts, including 8 phenolic acids: 5-O-caffeoylquinic acid (1), chlorogenic (2), 4-O-caffeoylquinic acid (3), 3,5-di-O-caffeoylquinic acid (4), 4,5-di-O-caffeoylquinic acid (5), 3,4-di-O-caffeoylquinic acid (6), caffeic acid (7) and methyl caffeate acid (8); 3 iridoids: secologanoside (9), sweroside (10) and secoxyloganin (11); and 3 flavonoids: luteolin (12), quercetin (13) and kaempferol (14). Compounds 1-9 and 11-14 showed anti-complementary activity in different extents and 3,5-di-O-caffeoylquinic acid (4) exhibited the most significant activity against the classical pathway.

CONCLUSIONCompound 14 is obtained from this plant for the first time, phenolic acids are the main anti-complementary constituents of L. japonica and 3,5-di-O-caffeoylquinic acid(4) is a potential complement inhibitor with strong activity, which worthy to be studied further in the future.

Complement Inactivating Agents ; chemistry ; isolation & purification ; pharmacology ; Hydroxybenzoates ; chemistry ; isolation & purification ; pharmacology ; Lonicera ; chemistry

OBJECTIVETo explore potency material bases of Xuebijing (XBJ) formula, and to analyze its effects at the molecular network level.

METHODSTotally 16 sepsis-related targets were selected and classified into three categories such as inflammation, immune, and coagulation referring to biological roles. Then molecular database of chemical compositions in XBJ formula were constructed to explore mutual actions with inflammation, immune, and coagulation targets.

RESULTSDanshen root and safflower, with more effector molecules with immune and coagulation targets, have extensive anticoagulation and anti-inflammation effects. The former 10 molecules with better mutual actions with sepsis targets were sequenced as tryptophane, danshensu, gallic acid, salvianolic acid D, protocatechuic acid, salvianolic acid A, danshensu C, vanillic acid, rosmarinic acid, phenylalanine. There existed two phenomena in XBJ formula as follows. One component had stronger actions with multi-targets, for example, danshensu had actions with 13 targets. Meanwhile, different components acted on the same target protein, for example, 8 molecules acted with MD-2.

CONCLUSIONXBJ formula had certain potential synergistic effects with sepsis targets, which could provide certain referential roles for findina new type anti-septic drugs.

Caffeic Acids ; Drugs, Chinese Herbal ; chemistry ; pharmacology ; therapeutic use ; Gallic Acid ; Hydroxybenzoates ; Inflammation ; Lactates ; Sepsis ; drug therapy

OBJECTIVETo study the effect of borneol on the pharmacokinetics of protocatechuic acid (PA) in rabbits.

METHODA method for determinating PA in rabbit plasma by high performance liquid chromatography (HPLC) was established. The 12 healthy New Zealand rabbits were randomly divided into 2 groups. PA concentration in plasma samples of rabbits was determined by HPLC after oral administration of PA (30 mg x kg(-1)) and PA combined with borneol (protocatechuic acid 30 mg x kg(-1) + borneol 15 mg x kg(-1)). The data were processed by DAS 2.0 software to calculate the pharmacokinetic parametes.

RESULTChromatographic peaks were separated well by the HPLC method. Regression analysis of the data of PA concentration against its peak area showed a good straight line in the range of 0.04-2.0 mg x L(-1) (r = 0.9983). In comparison with PA alone, the pharmacokinetics parameters of PA (t1/2Ka, T(max), V1/F, CL/F) in the PA + borneol combination group were decreased, while the AUC(0-infinity) was increased.

CONCLUSIONBorneol could significantly promote absorption, increase the dose absorption and slow elimination of PA in rabbits. Borneol could improve the bioavailability of PA.

Animals ; Bornanes ; pharmacology ; Chromatography, High Pressure Liquid ; Female ; Hydroxybenzoates ; blood ; pharmacokinetics ; Linear Models ; Male ; Rabbits ; Regression Analysis ; Reproducibility of Results

OBJECTIVEObserving the effect of phenolic acids from Arnebia euchroma assist mifepristone in anti-early pregnancy of SD rattus norvegicus.

METHODFeed the SD rattus norvegicus with phenolic acids from A. euchroma during the 7 th to 9 th day, and then we observe the restaining rate of pregnancy. At the same time, we determine the progesterone level in blood serum in the ways of radioimmunoassay.

RESULT720 g x kg(-1) enolic aids from A. euchroma can markedly increase the restaining rate of pregnancy (P < 0.05) than that only mifepristone dose (8.0 g x kg(-1)). In addition, the number of everage still bith increase, however, to the pogesterone level in blood serum. It has little effect.

CONCLUSIONThe effect of phenolic acids from A. euchroma assist mifepristone in anti-early pregnancy of SD rattus norvegicus is clear, and it dosen't work in the ways of decreasing the pogesterone level.

Abortifacient Agents ; chemistry ; pharmacology ; Animals ; Boraginaceae ; chemistry ; Female ; Hydroxybenzoates ; chemistry ; pharmacology ; Male ; Mifepristone ; pharmacology ; Pregnancy ; drug effects ; Progesterone ; blood ; Radioimmunoassay ; Rats ; Rats, Sprague-Dawley

OBJECTIVETo assess and compare the in vitro anti-oxidative activities among Siwu Decoction Serial Recipes, their composed crude herbs, and main aromatic acids they contained.

METHODSTheir anti-oxidative activities (including Siwu Decoction and correlated recipes such as Taohong Siwu Decoction, Xiangfu Siwu Decoction, Shaofu Zhuyu Decoction, and Xiongqiong Decoction, 16 kinds of crude herbs, and main aromatic acids they contained) were determined using 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical clearance method.

RESULTSThe selected five decoctions showed obvious activities of scavenging free radicals. Siwu Decoction was better than other decoctions in scavenging free radicals and Xiongqiong Decoction was the least. Among the 16 kinds of crude herbs, red peony root, white peony root, safflower, ligustici chuanxiong, common aucklandia root showed the strongest activities, while peach seed showed the poorest activities. Among aromatic acids, gallic acid, protocatechuic acid, vanillic acid, caffeic acid, chlorogenic acid, p-coumaric acid, and ferulic acid showed obvious anti-oxidative activities in scavenging free radicals, showing obvious dose-effect correlation. p-hydroxybenzoic acid, benzoic acid, and cinnamic acid showed no activities on scavenging free radicals (P > 0.05).

CONCLUSIONSiwu Decoction and aromatic acids contained in correlated decoctions played significant roles in anti-oxidative activities.

Antioxidants ; pharmacology ; Biphenyl Compounds ; Caffeic Acids ; pharmacology ; Chlorogenic Acid ; pharmacology ; Coumaric Acids ; pharmacology ; Dose-Response Relationship, Drug ; Drugs, Chinese Herbal ; pharmacology ; Free Radicals ; metabolism ; Gallic Acid ; pharmacology ; Hydroxybenzoates ; pharmacology ; Picrates

To investigate roles of nitric oxide (NO) signal in accumulations of phenolic acids in abscisic.acid (ABA)-induced Salvia miltiorrhiza hairy roots, S. miltiorrhiza hairy roots were treated with different concentrations of sodium nitroprusside (SNP)-an exogenous NO donor, for 6 days, and contents of phenolic acids in the hairy roots are determined. Then with treatment of ABA and NO scavenger (2-(4-carboxy-2-phenyl)-4,4,5,5-tetramethylimidazoline-1- oxyl-3-oxide, c-PTIO) or NO synthase inhibitor (NG-nitro-L-arginine methyl ester, L-NAME), contents of phenolic acids and expression levels of three key genes involved in phenolic acids biosynthesis were detected. Phenolic acids production in S. miltiorrhiza hairy roots was most significantly improved by 100 µmoL/L SNP. Contents of RA and salvianolic acid B increased by 3 and 4 folds. ABA significantly improved transcript levels of PAL (phenylalanine ammonia lyase), TAT (tyrosine aminotransferase) and RAS (rosmarinic acid synthase), and increased phenolic acids accumulations. However, with treatments of ABA+c-PTIO or ABA+L-NAME, accumulations of phenolic acids and expression levels of the three key genes were significantly inhibited. Both NO and ABA can increase accumulations of phenolic acids in S. miltiorrhiza hairy roots. NO signal probably mediates the ABA-induced phenolic acids production.
Abscisic Acid ; pharmacology ; Benzofurans ; metabolism ; Free Radical Scavengers ; pharmacology ; Hydroxybenzoates ; metabolism ; Nitric Oxide ; metabolism ; Phenylalanine Ammonia-Lyase ; metabolism ; Plant Roots ; metabolism ; Salvia miltiorrhiza ; metabolism ; Tyrosine Transaminase ; metabolism

Danshen, the dried root or rhizome of Salvia miltiorrhiza Bge., is a traditional and folk medicine in Asian countries, especially in China and Japan. In this review, we summarized the recent researches of Danshen in traditional uses and preparations, chemical constituents, pharmacological activities and side effects. A total of 201 compounds from Danshen have been reported, including lipophilic diterpenoids, water-soluble phenolic acids, and other constituents, which have showed various pharmacological activities, such as anti-inflammation, anti-oxidation, anti-tumor, anti-atherogenesis, and anti-diabetes. This article intends to provide novel insight information for further development of Danshen, which could be of great value to its improvement of utilization.
Diterpenes ; chemistry ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; pharmacology ; therapeutic use ; Hydroxybenzoates ; chemistry ; Molecular Structure ; Oils, Volatile ; chemistry ; Phytochemicals ; chemistry ; isolation & purification ; pharmacology ; therapeutic use ; Plant Roots ; chemistry ; Quality Control ; Salvia miltiorrhiza ; chemistry

To study the chemical constituents of Bauhinia glauca subsp. pernervosa, eleven phenolic acids were isolated from a 95% ethanol extract by using a combination of various chromatographic techniques including column chromatography over silica gel, ODS, MCI, Sephadex LH-20, and semi-preparative HPLC. By spectroscopic techniques including 1H NMR, 13C NMR, 2D NMR, and HR-ESI-MS, these compounds were identified as isopropyl O-beta-(6'-O-galloyl)-glucopyranoside (1), ethyl O-beta-(6'-O-galloyl)-glucopyranoside (2), 3, 4, 5-trimethoxyphenyl-(6'-O-galloyl)-O-beta-D-glucopyranoside (3), 3, 4, 5-trimethoxyphenyl-beta-D-glucopyranoside (4), gallic acid (5), methyl gallate (6), ethyl gallate (7), protocatechuic acid (8), 3, 5-dimethoxy-4-hydroxybenzoic acid (9), erigeside C (10) and glucosyringic acid (11). Among them, compound 1 is a new polyhydroxyl compound; compounds 2, 10, and 11 were isolated from the genus Bauhinia for the first time, and the other compounds were isolated from the plant for the first time. Compounds 6 and 8 showed significant protein tyrosine phosphatase1B (PTP1B) inhibitory activity in vitro with the IC50 values of 72.3 and 54.1 micromol x L(-1), respectively.
Bauhinia ; chemistry ; Benzoates ; chemistry ; isolation & purification ; pharmacology ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; pharmacology ; Gallic Acid ; analogs & derivatives ; chemistry ; isolation & purification ; pharmacology ; Glucosides ; chemistry ; isolation & purification ; pharmacology ; Hydroxybenzoates ; chemistry ; isolation & purification ; pharmacology ; Phenols ; chemistry ; isolation & purification ; pharmacology ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry ; Protein Tyrosine Phosphatase, Non-Receptor Type 1 ; metabolism

OBJECTIVETo observe the effects of a biotic elicitor fungal hyphae extract, an abiotic elicitor methyl jasmonate and their synergistic action on the accumulation of phenolic acids and tanshinones in Salvia miltiorrhiza hairy root.

METHODDifferent elicitors were added to S. miltiorrhiza hairy root, which was subcultured for 21 days, the dry weight and contents of phenolic acids and tanshinones were determined at different harvest-time.

RESULTS. miltiorrhiza hairy root growth was significantly inhibited by all three treatments and the accumulation of cryptotanshinone and dihydrotanshinone were promoted by each elicition. As for the accumulation of phenolic acids, there were differences between fungal elicitor and methyl jasmonate treatments, they were promoted by methyl jasmonate while inhibited in a certain extent by fungal hyphae extract.

CONCLUSIONFungal elicitor, methyl jasmonate and their synergistic action have significant influence on accumulation of components in S. miltiorrhiza hairy root, and the effect varies between phenolic acids and tanshinones. There is no correlation between production of water-soluble ingredients and fat-soluble components on the whole under three different treatments.

Acetates ; pharmacology ; Cyclopentanes ; pharmacology ; Diterpenes, Abietane ; metabolism ; Fungal Proteins ; metabolism ; pharmacology ; Hydroxybenzoates ; metabolism ; Membrane Glycoproteins ; metabolism ; pharmacology ; Oxylipins ; pharmacology ; Phytophthora ; chemistry ; metabolism ; Plant Extracts ; metabolism ; Plant Roots ; drug effects ; growth & development ; metabolism ; microbiology ; Salvia miltiorrhiza ; drug effects ; growth & development ; metabolism ; microbiology