In this paper, the correlation between the chemical constituents of Chinese herbal medicines Daphnes Cortex and the ecological factors and soil factors was studied, which provided a reference for the selection of suitable areas for artificial cultivation of Daphne giraldii and wild tending. The geographic information system(GIS) was applied to obtain the ecological factor information of 23 collection sites of Daphnes Cortex, and the soil factor information was determined by the standard procedure in the soil test standard manual. Combining the information of 93 chemical constituents of Daphnes Cortex in 23 collection sites the correlation between components and ecological factors and soil factors was analyzed by statistical methods. The correlation analysis showed that the longitude, annual average rainfall, annual sunshine intensity, annual average temperature in the ecological factors, soil type, effective copper and pH value were the dominant factors affecting the chemical composition of Daphnes Cortex.
China ; Copper ; Daphne/chemistry* ; Drugs, Chinese Herbal ; Geographic Information Systems ; Hydrogen-Ion Concentration ; Plants, Medicinal/chemistry* ; Rain ; Soil/chemistry* ; Sunlight ; Temperature

AIM: To evaluate the anti-HIV activity and mechanism of action of wikstroelide M, a daphnane diterpene from Daphne acutiloba Rehder (Thymelaeaceae). METHODS: The anti-HIV activities of wikstroelide M against different HIV strains were evaluated by cytopathic effect assay and p24 quantification assay with ELISA. The inhibitory effect of wikstroelide M on HIV reverse transcription was analyzed by real-time PCR and ELISA. The effect of wikstroelide M on HIV-1 integrase nuclear translocation was observed with a cell-based imaging assay. The effect of wikstroelide M on LEDGF/p75-IN interaction was assayed by molecular docking. RESULTS: Wikstroelide M potently inhibited different HIV-1 strains, including HIV-1IIIB, HIV-1A17, and HIV-19495, induced a cytopathic effect, with EC50 values ranging from 3.81 to 15.65 ng·mL⁻¹. Wikstroelide M also had high inhibitory activities against HIV-2ROD and HIV-2CBL-20-induced cytopathic effects with EC50 values of 18.88 and 31.90 ng·mL⁻¹. The inhibitory activities of wikstroelide M on the three HIV-1 strains were further confirmed by p24 quantification assay, with EC50 values ranging from 15.16 to 35.57 ng·mL⁻¹. Wikstroelide M also potently inhibited HIV-1IIIB induced cytolysis in MT-4 cells, with an EC50 value of 9.60 ng·mL⁻¹. The mechanistic assay showed that wikstroelide M targeted HIV-1 reverse transcriptase and nuclear translocation of integrase through disrupting the interaction between integrase and LEDGF/p75. CONCLUSION Wikstroelide M may be a potent HIV-1 and HIV-2 inhibitor, the mechanisms of action may include inhibition of reverse trascriptase activity and inhibition of integrase nuclear translocation through disrupting the interaction between integrase and LEDGF/p75.
Anti-HIV Agents ; pharmacology ; therapeutic use ; Cell Line ; Daphne ; chemistry ; Diterpenes ; pharmacology ; HIV Infections ; drug therapy ; virology ; HIV Integrase ; metabolism ; HIV Integrase Inhibitors ; pharmacology ; therapeutic use ; HIV Reverse Transcriptase ; antagonists & inhibitors ; HIV-1 ; drug effects ; enzymology ; HIV-2 ; drug effects ; Humans ; Intercellular Signaling Peptides and Proteins ; metabolism ; Phytotherapy ; Plant Extracts ; pharmacology ; therapeutic use ; Virus Integration ; drug effects ; Virus Replication ; drug effects

OBJECTIVETo study the chemical constituents from Daphne acutiloba.

METHODThe constituents were separated by column chromatography, and their structures were elucidated by spectroscopic data analyses.

RESULTFifteen compounds were isolated from the EtOAc extract and identified as wikstroelide M (1), vesiculosin (2), prostratin (3), 7-hydroxy-coumarin (4), 7,8-di-hydroxy-coumarin (5), isodaphnoside (6), daphnorine (7), rutamontine (8), daphnolin (9), daphneticin (10), (+)-pinoresinol-beta-D-glucoside (11), oleodapnone (12), oleodaphnal (13), ergosterol peroxide (14) and cholest-5-en-3beta-ol (15).

CONCLUSIONAll the compounds except for 4, 5 and 14 were obtained from the stems of this plant for the first time.

Coumarins ; chemistry ; isolation & purification ; Daphne ; chemistry ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Furans ; chemistry ; isolation & purification ; Lignans ; chemistry ; isolation & purification ; Mass Spectrometry

OBJECTIVETo study chemical constituents from rhizome of Daphne papyracea var. crassiuscula.

METHODEthyl acetate fraction of 75% ethanol extracts from rhizome of D. papyracea var. crassiuscula, and its strucutre was identified by spectral method.

RESULTNine compounds were separated and identified as daphneticin (1), daphnetin (2), hydrangetin (3), daphnoretin (4), 1-4'-hydroxyphenyl-5-phenyl-2 (E)-en-1-pentanone (5), daphneolon (6), 3beta-O-acetyl-olean-12-en (7), and (+)-usnic acid (8).

CONCLUSIONCompounds 1-8 were separated from D. papyracea var. crassiuscula for the first time. Compound 8 was separated from the genus for first time.

Chromatography, High Pressure Liquid ; Daphne ; chemistry ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Rhizome ; chemistry

By investigating the interaction between components from Flos Genkwa (FG) and Radix et Rhizoma Glycyrrhizae (RRG) and the dissolution profile of toxic components in co-decoction, the characteristics and possible mechanism of incompatibility were revealed. Ultra-high performance liquid chromatography quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF/MS) and ultra-high performance liquid chromatography triple-quadrupole mass spectrometry (UPLC-TQ/MS) were used to analyze multi-components in different herb extractions prepared by different ratios of FG/FG processed by vinegar (FGV) and RRG, which reflect the interaction and characteristics of multiple components in incompatibility combinations. The results showed that the components dissolution was influenced by compatibility ratio with certain regularity. Whether FG processed by vinegar or not, with the increase of RRG in co-decoction, the dissolution of diterpenes, especially for yuanhuacine, yuanhuadine and yuanhuajine, the toxic ingredients of FG, increased significantly. From these results, the material basis and one possible mechanism of incompatibility between FG and RRG is the increasing dissolution of diterpenes, toxic components of FG in co-decoction process, which caused by interaction between multi-components in these two herbs.
Acetic Acid ; chemistry ; Chromatography, High Pressure Liquid ; Daphne ; chemistry ; Diterpenes ; analysis ; Drug Incompatibility ; Flowers ; chemistry ; Glycyrrhiza uralensis ; chemistry ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Rhizome ; chemistry ; Spectrometry, Mass, Electrospray Ionization ; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization ; Tandem Mass Spectrometry ; Terpenes ; analysis

OBJECTIVETo study the chemical constituents of Daphne odora var. margirmta.

METHODThe compounds were isolated and purified by column chromatography of silica gel, ODS, Sephadex LH-20, and their structures were identified by UV, 1H-NMR, 13C-NMR, MS and CD spectroscopic methods.

RESULTTen compounds were elucidated as wikatrols B (1), kaempferol (2), daphnodorin B (3), daphnodorin D2 (4), daphnodorin A (5), daphnodorin C (6), daphnodorin D1 (7), daphnodorin I (8), daphnetin (9), daphnoretin (10).

CONCLUSIONCompounds 1,2,4 were obtained from this plant for the first time,and compound 1 was isolated firstly from the genus Daphne.

Daphne ; chemistry ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Plant Roots ; chemistry

OBJECTIVETo determine the contents of tiliroside [kaempferol 3-O-beta-D-(6 " -p-coumaroyl) glucopyranoside] in the Daphne genkwa.

METHODThe separation was performed on ZORBAX XDB C18 column (4.6 mm x 250 mm, 5 microm), using acetonitrile and water/acetic acid mixture (1,000/1) (gradient elution: 0-18 min, 26 : 74; 18-33 min, 80 : 20) as mobile phase with the rate of 1.0 mL x min(-1) at 25 degrees C, the wavelength for measurement was 310 nm.

RESULTThe linearity was in the range of 0.1-5.0 microg (n=6), and the correlation coefficient was 0.9999. The average recovery for compound tiliroside was 101.50% (RSD 0.90%) (n=6).

CONCLUSIONThis method is accurate, reliable and reproducible to determine tiliroside in the D. genkwa.

Acetonitriles ; chemistry ; Chromatography, High Pressure Liquid ; methods ; Daphne ; chemistry ; Flavonoids ; isolation & purification ; Oils, Volatile ; pharmacology ; Plant Stems ; chemistry

OBJECTIVETo investigate the modulation of Glycyrrhiza inflata and Daphne genkwa on the permeability characteristics of rhodamine 123 (R123), one P-glycoprotein (P-gp) substrate, across the jejunum membranes. And then approach the possible permeability mechanism of the drugs after co-administration of G. inflata and D. genkwa in gastrointestinal tract.

METHODThe permeability of R123 or fluorescein sodium (CF) via Wistar rat jejunum membranes was evaluated by in vitro diffusion chamber system after oral administration of four different decoctions and 0.9% sodium chloride (20 mL x kg(-1)) for 1 week. And the concentration of R123 or CF was determined by the fluorospectrophotometry. The apparent permeability coefficient (P(app)) was calculated by the equation P(app) = dQ/d(t) x (1/A x C0), where P(app) was expressed in cm/s, dQ/dT was the slope of the linear portion of the permeation curves, A was the diffusion area, and C0 was the initial concentration of rebamipide in the donor side, and then compare their differences were compared with control group.

RESULTAfter oral administration of G. inflata decoction, D. genkwa decoction and decoction of the combination of the previous decoctions, the absorptive directed transport of R123 was significantly increased (P < 0.05, compared with control group). On the other hand, D. genkwa could also decrease the permeability of secretory directed transport (P(app) = 2.98 +/- 0.59), while no action of G. inflata was found on the secretory transport of R123 ( P(app) = 5.24 +/- 3.98) across the jejunum tissues, while P(app) of control group was 4.38 +/- 1.18. Meanwhile, G. inflata had no effect on transport of CF across the jejunum tissues, though the other three groups could decrease the permeability of CF, as compared with control group.

CONCLUSIONG. inflata may slightly inhibit P-glycoprotein function in the intestinal membrane, while D. genkwa may be a relatively strong inhibitor of P-gp. For another, some compositions in D. genkwa inhibit P-gp function, and some others strengthen the tight junction between cells in the intestinal membrane to decrease permeability of CF. As the inhibitory action to P-gp was enhanced by combination of G. inflata and D. genkwa, based on the results, it may be one of the mechanisms of creating toxicity once co-administration of G. inflata and D. genkwa.

Animals ; Cell Membrane Permeability ; drug effects ; Daphne ; chemistry ; Drugs, Chinese Herbal ; chemistry ; pharmacology ; Glycyrrhiza ; chemistry ; In Vitro Techniques ; Jejunum ; drug effects ; metabolism ; Male ; Random Allocation ; Rats ; Rats, Wistar ; Rhodamine 123 ; pharmacokinetics

OBJECTIVETo study the constituents with the pain-relieving activity from the stem rind of Daphne giraldii.

METHODThe partition of the ethanol extract and chromatographic separation of the fractions were carried out by the monitoring of anelgesic pharmacological activity. The structures of the isolated compounds were determined by MS and NMR.

RESULTFour compounds were isolated from the pain-relieving fraction. Three of them were identified as diterpenes, gniditrin (1), gnidicin (2) and daphnetoxin (3). Compound 4 was determined as Z-octadecyl caffeate.

CONCLUSIONCompounds 1, 2 and 4 were isolated from the plant for the first time.

Analgesics ; chemistry ; isolation & purification ; pharmacology ; Caffeic Acids ; chemistry ; isolation & purification ; pharmacology ; Daphne ; chemistry ; Diterpenes ; chemistry ; isolation & purification ; pharmacology ; Heterocyclic Compounds, 4 or More Rings ; chemistry ; isolation & purification ; pharmacology ; Molecular Structure ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry

AIMTo investigate the chemical constituents of the secondary metabolites of the roots of Daphne genkwa.

METHODSThe roots of D. genkwa were extracted with 95% ethanol at 60-70 degrees C for 7 days to obtain the crude extract. The crude extract was purified by silica gel and Sephadex LH-20 column chromatography as well as the HPLC techniques. The structures of the isolates were elucidated by combined spectroscopic methods including 1D and 2D NMR, MS, UV, IR and CD.

RESULTSThree new biflavonoids were isolated from the ethanol extract of the roots of D. genkwa and their structures were identified as daphnodorin H-3-methyl ether (1), daphnodorin H-3"-methyl ether (2) and daphnodorin G-3"-methyl ether (3).

CONCLUSIONCompounds 1, 2 and 3 are three new biflavonoids.

Biflavonoids ; chemistry ; isolation & purification ; Daphne ; chemistry ; Ethanol ; Molecular Conformation ; Molecular Structure ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry