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Rhus verniciflua Stokes (RVS), used as a food additive and a traditional herbal medicine, has both antioxidant and antitumor activities which are known to be closely associated with the polyphenolic compounds that it contains. In the present study, we purified a fraction from a crude acetone extract of RVS, named RCMF (RVS chloroform-methanol fraction), and evaluated its ability to scavenge free radicals and inhibit cell growth. In addition, the active compounds responsible for the activities were identified. Results showed that RCMF contained an antioxidant potential and strongly suppressed the proliferative capability of B lymphoma cells. RCMF-mediated suppression of cell growth was verified to be apoptotic, based on the increased DNA fragmentation and low fluorescence intensity in the nuclei after propidium iodide staining, and also on the appearance of DNA laddering. Finally, EI-MS, 1H-NMR, and 13C-NMR spectra confirmed that RCMF contained flavonoid derivatives, including protocatechuic acid, fustin, fisetin, sulfuretin, and butein, suggesting that these flavonoid derivatives are the main active compounds responsible for the antioxidant and antiproliferative activities of RCMF.

Glycoprotein of Rhus verniciflua Stokes (RVS glycoprotein) was isolated and identified using SDS-PAGE. To study the anti-apoptotic effects of RVS glycoprotein on mouse splenocytes, splenocytes were exposed to 100 nM TPA (61.68 ng/ml) for 3 h with or without RVS glycoprotein (100 microg/ml). Results from our experiment showed that RVS glycoprotein protects from splenocyte apoptosis induced by 12-O-tetradecanoylphorbol 13-acetate (TPA). We also studied the effects of RVS glycoprotein on the proliferation of T/B cells and the production of cytokines. Our results showed that Concanavalin A (Con A)-induced T cell proliferation and the production of interleukin-2 (IL-2)/interleukin-4 (IL-4) were reduced, and that Lipopolysaccharide (LPS)-induced B cell proliferation and the Tumor necrosis factor alpha (TNF-alpha) were reduced significantly by the addition of 50 microg/ml RVS glycoprotein (P<0.01), compared to the control. These results indicate that RVS glycoprotein has the capacity to modulate apoptosis, cytokine production and T/B cell proliferation in splenocytes.

A study has been made of the semi-synthesis of 1,3-diols (anacardic alcohols) from natural phenolic lipid resources from Anacardium occidentale and Anacardium giganteum which have given C15 and C11 derivatives, respectively. An isomeric 1,3-diol (isoanacardic alcohol) has been obtained from cardanol separated from technical cashew nut-shell liquid. Homologous 1,3-diols have been synthesised from a range of synthetic 2-alkyl-, 3-alkyl- and 4-alkylphenols and from 6-alkylsalicylic acids. The natural 1,2-diol, urushiol, from Rhus vernicifera has been purified. All these lipidic compounds have been studied for their complexation and the potential recovery of boron as boric acid.

The antioxidant efficacy of rosemary (Rosmarinus officinalis L.), sage (Salvia fruticosa L.), and sumac (Rhus coriaria L.) extracts and combinations at 4% concentrations (wt/vol, extract/oil) were investigated. Methanolic extracts of rosemary, sage, sumac, and their combinations were applied to peanut oil stored at 80 degrees C for 24 h. The antioxidant effect was determined by measuring the peroxide value. All extracts showed antioxidant effects compared with control. But the antioxidant effect of all extracts was low compared with that of butylated hydroxytoluene. Rosemary extract (except for 3 and 4 h) exhibited the most antioxidant effect compared with other individual extracts. Of blends, the most effective ones were sage plus sumac combinations. Sumac extract is also promising as a source of natural antioxidants.

As a defense mechanism of the leaves of Rhus javanica (Anacardiaceae) against the aphid Melaphis chinensis (Aphididae) attack, tannic acid is rapidly accumulated and forms galls along the midrib of the leaves resulting in a unique natural medicine Gallae Rhois. Tannic acid was found to inhibit the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by tyrosinase (EC 1.14.18.1) with an IC50 of 22 microM. The aphid would detoxify the ingested toxic tannic acid to relatively nontoxic gallic acid, whereas the non-adapted pink bollworm Pectinophora gossypiella larvae are sensitive to the ingested tannic acid.

Rhus verniciflua Stokes (RVS) has been used as a traditional herbal medicine. Several earlier studies indicated that an ethanol extract of RVS has both anti-oxidant and anti-tumor properties, although the mechanism for the activity remains to be elucidated. In this report, we prepared a highly purified ethanol extract from RVS, named REEE-1 (Rhus ethanol eluted extract-1), and investigated the mechanism involved in its growthinhibitory effect on the human B and T lymphoma cell lines, BJAB and Jurkat, respectively. Results from tritium uptake proliferation assays showed that the proliferative capacities of both BJAB and Jurkat cells were strongly suppressed in the presence of REEE-1. This was further confirmed through trypan blue exclusion experiments that revealed a dose-dependent decrease in viable cell numbers after REEE-1 treatment. REEE-1-mediated suppression of cell growth was verified to be apoptotic, based on the increase in DNA fragmentation, low fluorescence intensity in nuclei after propidium iodide staining, and the appearance of DNA laddering. In particular, REEE-1 exerted its anti-oxidant activity through the inhibition of hydroxyl radical-mediated degradation by iron ion chelation rather than direct scavenging of hydroxyl radicals. Furthermore, REEE-1 was revealed to be a potential scavenger of superoxide anions. Collectively, our findings suggest that REEE-1 is a natural anti-oxidant that could be used as a cancer chemo-preventive and therapeutic agent.

Biflavonoids detected in trace amounts in an earlier investigation of the twigs of Rhus pyroides have now been found in the root bark of this species. These new flavonoids belong to a rare bichalcone class and have been identified as 2',4',4' ',2' ",4' "-pentahydroxy-4-O-5' "-bichalcone (rhuschalcone II, 2), 2',4',4' ',2' "-tetrahydroxy-4' "-methoxy-4-O-5' "-bichalcone (rhuschalcone III, 3), 4,2',4' ',2' "-tetrahydroxy-4' "-methoxy-4'-O-5' "-bichalcone (rhuschalcone IV, 4), 4,2',4',4' ',2' ",4' "-hexahydroxy-3,5' "-dihydrochalcone-chalcone (rhuschalcone V, 5), and 4,2',4',4' ',2' ",4' "-hexahydroxy-3,5' "-bichalcone (rhuschalcone VI, 6), repectively. Also obtained was the known compound rhuschalcone I (1). Their structures were determined by spectroscopic and chemical methods, and for 1-3 by total synthesis. All the bichalcones (1-6) tested exhibited selective cytotoxic activity against the HT29 and HCT-116 colon tumor cell lines.

The effect of pH on Cu(I) and Cu(II) forms of the isolated soluble domain of the stellacyanin from Rhus vernicifera (SCu), the Japanese lacquer tree, has been studied by electronic and NMR spectroscopy and using direct electrochemical measurements. A pK(a) value of 10.1-10.4 is observed for the alkaline transition in this oxidized phytocyanin and results in a slightly altered active-site structure, as indicated by changes in the visible and paramagnetic (1)H NMR spectra. Electrochemical studies show that the pK(a) value for this transition in SCu(I) (reduced SCu) is 11.0. These results are compared with those recently obtained for other phytocyanins, and in particular umecyanin. In all cases, the alkaline transition is caused by the deprotonation of the surface lysine residue adjacent to the axial ligand. This lysine residue is completely conserved in known phytocyanin sequences. Also highlighted in these studies are the remarkable active-site similarities between stellacyanin and umecyanin.

The present study examined the inhibitory effect of aqueous extract from the gall of Rhus chinensis (AEGRC) on alpha-glucosidase activity, an enzyme responsible for digestion of carbohydrate to monosaccharides in the process of intestinal absorption. AEGRC inhibited Bacillus alpha-glucosidase acitvity with an IC(50) of 0.9 micro g/ml. Its inhibition on alpha-glucosidase was determined to be noncompetitive and reversible when the enzyme-substrate mixture was simultaneously treated with AEGRC as an inhibitor. In addition, when it was orally administered to rats with sucrose (2g/kg), AEGRC (250-1000mg/kg) significantly suppressed the increase of blood glucose levels after sucrose loading in a dose dependent manner. These results suggest that AEGRC might exert anti-diabetic effect by suppressing carbohydrate absorption from intestine, and thereby reducing the postprandial increase of blood glucose.

The antioxidant activities of sumach (Rhus coriaria L.) extracts and butylated hydroxyanisole (BHA) at various concentrations were tested in natural peanut oil stored at 65 degrees C for 35 days. The concentrations (weight/volume) of extracts added into oil were 1.0%, 3.0%, and 5.0%, and those of BHA were 0.1%, 0.3%, and 0.5%. Antioxidant effect was determined by the measurement of peroxide value. After 7 days of storage, BHA and extracts of sumach were active in varying degrees against autoxidation of peanut oil, compared with the control test (P <.01). The sumach extracts generally inhibited the formation of hydroperoxide, as did BHA. After 28 days of storage, antioxidant effects of extracts were significantly decreased when compared with BHA. The decrease in the antioxidant activity of extracts might have resulted from the decrease of polyphenolic constituents. The results showed that high concentrations can enhance the potency of the antioxidant effect of sumach extract.

Rhus coriaria L. (Anacardiaceae) is a well-known spice in the Middle-East and grown in the Central and East Anatolia region of Turkey. A methanolic extract (water-soluble part constituents) of R. coriaria, was found to be an uncompetitive inhibitor of xanthine oxidase and scavenger of superoxide radical in vitro with IC50 values of 172.5 microg/mL and 232 microg/mL respectively. Superoxide radicals were generated either by an enzymatic or a non-enzymatic system, and scavenging ability was evaluated by the inhibition of nitroblue tetrazolium reduction. This study provides evidence that a crude extract of R. coriaria exhibits interesting antioxidant properties, expressed either by the capacity to scavenge superoxide radical or to uncompetitively inhibit xanthine oxidase.

A synthesis of (15:1)-urushiol, urushiol monoene, 3-[(Z)-pentadec-8-enyl] catechol, 1,2-dihydroxy-3-[(Z)-pentadec-8-enyl] benzene, one of the toxic principles of Rhus toxicodendron and of Rhus vernicifera is described. 6-Chlorohexan-1-ol protected at the OH group with ethyl vinyl ether reacted with 2,3-dimethoxybenzaldehyde in the presence of lithium to give, after removal of the protective group with methanolic 4-toluenesulphonic acid, 1-(2,3-dimethoxyphenyl) heptane-1,7-diol. Catalytic hydrogenolysis in ethanol with palladium-carbon selectively afforded 7-(2,3-dimethoxyphenyl)heptane-1-ol accompanied by a small proportion of the 7-(3-methoxyphenyl)heptane-1-diol, formed by demethoxylation. Reaction of the dimethoxy compound with boron tribromide resulted in both bromination and demethylation to give 7-(2,3-dihydroxyphenyl) heptylbromide. This bromide in tetrahydrofuran (THF) containing hexamethylphosphoric triamide reacted with excess lithium oct-1-yne to give 3-(pentadec-8-enyl)catechol which, by catalytic hydrogenation in ethyl acetate containing quinoline, selectively formed the required cis product, 3-[(Z)-pentadec-8-enyl]catechol which was identical chromatographically and spectroscopically with urushiol monoene separated from the natural product.

Two new antioxidative and cytotoxic compounds, 10'(Z),13'(E),15'(E)-heptadecatrienylhydroquinone (1) and 10'(Z),13'(E)-heptadecadienylhydroquinone (2), as well as the known 10'(Z)-heptadecenylhydroquinone (3), were isolated from an EtOH extract of the sap of Rhus succedanea. The structures were elucidated by spectral analyses. These compounds showed antioxidative and cytotoxic activities against five cancer cell lines.

Rhus verniciflua Stokes (RVS) is a widely used herbal plant with various biological properties. Our previous study using cultured neuronal cells showed that an ethanol extract of RVS had strong antioxidant properties. In this study, we characterized the antioxidant activity of the RVS ethanol extract and identified the active compounds responsible for this activity. From the RVS ethanol extract, we derived three water-eluted fractions and another three fractions eluted by organic solvents, and determined that the water-eluted fractions are what protect against reactive oxygen species (ROS) generated by iron and enzymes. Water-eluted fraction F(2) was the most efficient antioxidant. Moreover, DNA fragmentation and terminal deoxynucleotidyl transferase (TdT)-mediated dUTP nick-end labeling (TUNEL) staining experiments revealed that F(2) also protects against thymocyte apoptosis mediated by hydroxyl radicals. Finally, EI-MS, (1)H-NMR, and (13)C-NMR spectra signals confirmed that the fraction contained flavonoid derivatives, including fustin, quercetin, butein, and sulfuretin. These results suggest that the flavonoid derivatives in F(2) are the compounds in the RVS ethanol extract that act as antioxidants.

The biflavanone (2S,2"S)-7,7"-di-O-methyltetrahydroamentoflavone and five known flavonoids, 7-O-methylnaringenin, 7,3'-O-dimethylquercetin, 7-O-methylapigenin, 7-O-methylluteolin, and eriodictyol were isolated from the leaves of Rhus retinorrhoea Steud, Ex Olive. The biflavanone exhibited moderate antimalarial activity with IC50 0.98 microg/ml against Plasmodium falciparum (W2 Clone) and weak activity against P. falciparum (D6 Clone) with IC50 2.8 microg/ml. Nevertheless, it did not display any cytotoxicity. 7-O-Methylnaringenin showed weak antimicrobial activity against Candida albicans, C. krusei, Staphylococcus aureus, Mycobacterium smegmatis, M. intracellulare, and M. xenopi with MIC approximately 100 microg/ml. Characterization of each compound was based on spectral analysis and comparison with reported data.

Three new dammarane triterpenes and semialactic acid were isolated from the stem bark of Rhus javanica. The structures of these triterpenes, named semialactone, isofouquierone peroxide and fouquierone, were elucidated by 2D-NMR analysis (HMQC, 1H-1H COSY and HMBC), and the 13C-NMR data of semialatic acid is revised.

Laser irradiation in the 450 nm region brings about irreversible changes in the copper sites of Rhus vernicifera lactase and its type 2 Cu-depleted derivative. The absorption band at 614 nm disappears after &#95; 2 hr of irradiation with a 200 mW laser beam; the amount of the paramagnetic detectable copper does not decrease, indicating no reduction of these types of copper. No apparent rearrangement of the protein backbone occurs, as ultaviolet dichroic spectra of the enzyme before and after the irradiation do not show appreciable differences. Stellacyanin is insensitive to laser radiation at any wavelength.

The resonance Raman spectra of native stellacyanin and its Ni(II) derivative has been investigated. Raman intensity as a function of the exciting frequency shows minima at about 440--460 nm. Moreover, the resonance Raman spectra of the Ni(II) derivative indicate similar symmetry and nature of ligands, namely, one cysteine and at least one histidine.Optical electronegativity of the ligand involved in the intense visible absorption band of native stellacyanin and the corresponding transition of the Ni(lI) derivative confirm this assumption. The origin of the 450 nm band is also discussed.