Phenylethanoid Glycosides From Callicarpa kwangtungensis Chun Attenuate TNF-α-Induced Cell Damage by Inhibiting NF-κB Pathway and Enhancing Nrf2 Pathway in A549 Cells.

Background: Acute lung injury (ALI) is a complicated and severe lung disease, which is often characterized by acute inflammation. Poliumoside (POL), acteoside (ACT) and forsythiaside B (FTB) are phenylethanoid glycosides (PGs) with strong antioxidant, anti-inflammatory, and anti-apoptotic properties, which are extracted from Callicarpa kwangtungensis Chun (CK). The aim of this study was to investigate the protective effects of POL, ACT, and FTB against TNF-α-induced damage using an ALI cell model and explore their potential mechanisms. Methods and Results: MTT method was used to measure cell viability. Flow cytometry was used for detecting the apoptosis rate. Reactive oxygen species (ROS) activity was determined using fluorescence microscope. The expression of mRNA in apoptosis-related genes (Caspase 3, Caspase 8, and Caspase 9) were tested by qPCR. The effects of POL, ACT, FTB on the activities of nuclear factor erythroid-2 related factor 2 (Nrf2), nuclear factor kappa-B (NF-κB) and the expression of their downstream genes were assessed by western blotting and RT-PCR in A549 cells. In the current study, POL, ACT, and FTB dose-dependently attenuated TNF-α-induced IL-1ß, IL-6 and IL-8 production, cell apoptosis, the expression of apoptosis-related genes (Caspase 3, Caspase 8, and Caspase 9) and ROS activity. POL, ACT, and FTB not only increased in the mRNA levels of antioxidative enzymes NADPH quinone oxidoreductase (NQO1), glutamate cysteine ligase catalytic subunit (GCLC), heme oxygenase (HO-1), but also decreased the mRNA levels of IL-1ß, IL-6 and IL-8. Furthermore, they upregulated the expression of Keap1 and enhanced the activation of Nrf2, while decreased the expression of phosphor-IκBα (p-IκBα) and nuclear p65. In addition, no significant changes were observed in anti-inflammatory and antioxidant effects of POL, ACT, FTB following Nrf2 and NF-κB p65 knockdown. Conclusion: Our study revealed that POL, ACT, and FTB alleviated oxidative damage and lung inflammation of TNF-α-induced ALI cell model through regulating the Nrf2 and NF-κB pathways.

New glycosylsphingolipids from Psychotria serpens L.

In clinical, Psychotria serpens L. was often substitute for Caulis trachelospermi to treat cancer in China. Meanwhile, EtOAc and n-BuOH fractions of MeOH extract of P. serpens L. show power activity against H460, HepG2, Hela, and PC9/GR cell lines, and no toxic effects against normal 16HBE cell lines. In our ongoing search for bioactive novel compounds from Chinese material medica, one new type of glycosylsphingolipids Psychotramide (1a-1c) were isolated from P. serpens L., and their structures were identified through spectroscopic techniques including NMR (1D and 2D) and MS (LC-MS, and GC-MS).

[Interaction of phenylethanoid glycosides and calf thymus DNA].

In physiological condition, the interaction of acteoside and forsythoside B with calf thymus DNA using neutral red (NR) as a fluorescence probe were investigated by fluorescence, UV-visible spectrophotometry, viscosity, DNA melting techniques, and molecular docking. It is observed that acteoside and forsythoside B can react with DNA. The major mode of recognition between drug and DNA is groove binding by hydrogen bonds, and the interaction of acteoside with DNA is stronger than that of forsythoside B.

Structure-activity relationships of antioxidant activity in vitro about flavonoids isolated from Pyrethrum tatsienense.

AIM: Antioxidant activity is one of the important indexes for estimating medicinal value for the traditional Chinese medicine. The aim of this study is to investigate the antioxidant activity of 11 flavonoids mainly revealing luteolin as mother nucleus isolated from Pyrethrum tatsienense. MATERIALS AND METHODS: The antioxidant activity of 11 flavonoids was measured in vitro using the classical 1,1-diphenyl-2-picrylhydrazyl removal method. The percentages of scavenging activity of 11 flavonoids were analyzed by taking the choice of a-tocopherol as positive drugs, and the scavenging activity was plotted against the sample concentration to obtain the IC50 values. RESULTS: Ten flavonoids containing phenolic hydroxyl groups have different levels of antioxidant activity. Antioxidant activity mainly depends on the numbers and the substitutional positions of phenolic hydroxyls in B ring. When C-3', 4' positions in B ring of flavonoids are replaced by hydroxyl groups, the antioxidant activity improved remarkably. Phenolic hydroxyl groups in A ring contribute some to antioxidant activity because of the electrophilic effect of C ring, and the numbers and substitutional positions of methoxyl and glycosyl have a little effect on the antioxidant activity. CONCLUSION: Structure-activity relationships of antioxidant activity about flavonoids isolated from P. tatsienense are concluded, which will be beneficial to deep understanding the pharmacological functions of this Tibetan medicine in vivo from the point of antioxidation.

Diterpenoid alkaloids and flavonoids from Delphinium trichophorum.

Five hetisane-type C20-diterpenoid alkaloids, trichodelphinines A-E, one delnudine-type C20-diterpenoid alkaloid, trichodelphinine F and three known flavonoids, quercetin, quercetin 3-O-ß-D-glucopyranoside, and quercetin 3-O-ß-D-glucopyranoside-7-O-α-L-arabinopyranoside, were isolated from whole plants of Delphinium trichophorum Franch. Their structures were elucidated on the basis of extensive spectroscopic analysis, including HSQC, HMBC, (1)H-(1)H COSY, NOESY and X-ray crystallographic analysis, and from chemical evidence. The cytotoxic activities of the diterpenoid alkaloids were evaluated using the MTT method, and the IC50 values of their cytotoxicity against A549 cancer cells ranged from 12.03 to 52.79 µM.

Investigation on the differences of four flavonoids with similar structure binding to human serum albumin.

Flavonoids are structurally diverse and the most ubiquitous groups of polyphenols distributed in the various plants, which possess intensive biological activities. In this study, the interaction mechanisms between four flavonoids containing one glucose unit with similar molecular weight isolated from the Tibetan medicinal herb Pyrethrum tatsienense, namely, apigenin-7-O-ß-D-glucoside(1), luteolin-7-O-ß-D-glucoside(2), quercetin-7-O-ß-D-glucoside(3), quercetin-3-O-ß-D-glycoside(4), and human serum albumin(HSA), were investigated by fluorescence, UV-vis absorbance, circular dichroism, and molecular modeling. The effects of biological metal ions Mg2+, Zn2+, and Cu2+ on the binding affinity between flavonoids and HSA were further examined. Structure-activity relationships of four flavonoids binding to HSA were discussed in depth and some meaningful conclusions have been drawn by the experiment data and theoretical simulation. In addition, an interesting phenomenon was observed that the microenvironment of the binding site I in HSA has hardly changed in the presence of 4 differentiating from the other three flavonoids on the basis of conformation investigations.

[Study on chemical constituents of Callicarpa peii].

OBJECTIVE: To study the chemical constituents of Callicarpa peii. METHODS: The chemical constituents were isolated and purified by chromatographic methods and elucidated by spectral analysis, including UV, IR, MS, 1H-NMR and 13C-NMR. RESULTS: Ten compounds were obtained and identified as oleanolic acid (1), 2beta, 3beta,19alpha-trihydroxy-12-en-28-ursolic acid (2), luteolin -7,4'-dimethylether (3), luteolin -3', 4', 7, -trimethylether (4), luteolin -4'-methylether (5), hydnocarpin (6), luteolin (7), lyoniresinol 3alpha-O-beta-D-glucopyranoside (8), kelampayoside A (9), kaempferol -3-O-glucuronide (10). CONCLUSION: All these compounds are isolated from Callicarpa peii for the first time and compounds 3, 4, 6, 8 and 10 are isolated from this genus for the first time.

Phenylethanoid glycosides from the stems of Callicarpa peii (hemostatic drug).

Two new trisaccharide intermediates of phenylethanoid glycosides, peiioside A(1)/A(2) (1a/1b) and peiioside B (2), were isolated from the n-BuOH fraction of MeOH extract of the stems of Callicarpa peii H.T. Chang, together with five biogenetic relevant known compounds 3-7. The structures of compounds 1 and 2 were elucidated by extensive spectroscopic methods (especially 2D-NMR techniques) and acid-catalyzed hydrolysis as O-α-l-rhamnopyranosyl-(1″→3')-O-[ß-d-apiofuranosyl-(1‴→6')] -4'-O-[(E)-caffeoyl]-d-glucopyranoside] (1a/1b), 3,4-dihydroxy-ß-phenylethoxy-O-[ß-d-apiofuranosyl-(1‴→6')-α-l-rhamnopyranosyl-(1″→3')-O-ß-d-glucopyranoside] (2), respectively. On the basis of the isolated compounds, a presumable biogenetic pathway of the biologically interesting phenylethanoid glycosides about forsythoside B (3) and acteoside (4) isolated from this species was proposed. Isolation of five related intermediates (1-2, 5-7) provided further support for the biogenetic path. This is the first report about phytochemical research on C. peii and the biogenetic hypothesis of forsythoside B and acteoside.

Investigation of the interaction between two phenylethanoid glycosides and bovine serum albumin by spectroscopic methods.

Two phenylethanoid glycosides, acteoside and forsythoside B, were first isolated from the traditional Chinese herb Callicarpa peii H.T. Chang. The interaction between the two phenylethanoid glycosides and bovine serum albumin (BSA) was investigated by fluorescence, UV-vis absorbance and circular dichroism (CD). The results showed that the quenching mechanism in the drug-BSA binary systems was a combination of static quenching and non-radiative energy transfer. Displacement experiments confirmed that the drug bound to the site I of BSA. UV-vis and CD measurements indicated that the binding of the drug to BSA induced conformational changes in BSA.

catena-Poly[[[pentaaquaeuropium(III)]-µ-5-sulfonatoisophthalato-κO,O:O,O] 4,4'-bipyridine N,N'-dioxide hemisolvate trihydrate].

In the crystal structure of the title compound, {[Eu(C(8)H(3)O(7)S)(H(2)O)(5)]·0.5C(10)H(8)N(2)O(2)·3H(2)O}(n), the Eu(III) coordination polymer displays a ribbon motif as the 5-sulfoisopthalate anion uses one of carboxyl -CO(2) units to chelate to a Eu atom and the other to bind to other two Eu atoms; the sulfonyl -SO(3) unit is not involved in coordination. Adjacent ribbons are linked by O-H⋯O hydrogen bonds, generating a three-dimensional network. The 4,4'-bipyridine-N,N'-dioxide mol-ecule lies on an inversion centre and is hydrogen-bonded to the complex network. The coordination geometry of the Eu atom is a monocapped square anti-prism.

Bis{(1-methyl-imidazol-2-ylmeth-yl)[2-(2-pyridyl)eth-yl]amine-κN,N',N''}zinc(II) bis-(hexa-fluoridophosphate).

Two tridentate N-heterocyclic ligands chelate the Zn(II) atom in the title compound, [Zn(C(12)H(16)N(4))(2)](PF(6))(2), conferring a fac-octa-hedral geometry. The Zn(II) atom lies on a center of inversion. The cation is linked to the anion by an N-H⋯F hydrogen bond.

[Preparation and spectra of the complexes of the first series transition metals with diphenic acid].

The ligand diphenic acid has been synthesized and the corresponding complexes of transition metal Co, Ni and Mn with diphenic acid have been prepared and characterized by the elementary analysis, IR spectra and ultraviolet-visible spectra. The results of IR show that the vas and vs of -CO2- in the complexes are lower than those of ligand diphenic acid, which can be explained by the coordinating between metal and ligand. In addition, compared with the complex IR spectra, the IR spectra of ligand became complicated due to the ligand polymerization through hydrogen bond. The UV-Vis spectra show that the ligand has three absorption peaks at 288, 273 and 270 nm, respectively, and these are slightly shifted in the complexes. Because the metal d-d absorption is weak, only in Co(C14H8O4) x 2H2O there is a d-d absorption at 537 nm.