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PubMed2006

Clinical study on effect of Garlicin in stabilizing the carotid artery atherosclerotic plaque in patients with primary hypertension and coronary artery disease.

OBJECTIVE: To investigate the effect of garlicin in treating carotid artery atherosclerotic plaque (CAAP) in patients with primary hypertension and coronary heart disease (PHT-CHD). METHODS: Seventy-nine patients with PHT-CHD were randomly divided into the treated group (39 patients) treated with garlicin and fosinopril and the control group (40 patients) treated with fosinopril alone. The change of CAAP was evaluated by high frequency ultrasonic examination every six months, and the changes of intercellular adhesion molecule-1 (ICAM-1) and high sensitive C-reactive protein (hs-CRP) were measured by ELISA, with the observation proceeding for 52 weeks totally. RESULTS: By the end of the experiment, the number of complex plaques, Crouse integrals, intima-media thickness, serum ICAM-1 and hs-CRP were significantly lower in the treated group than those in the control group with significant difference (P < 0.05). CONCLUSION: Garlicin could stabilize CAAP to a certain extent and shows a definite vascular protective effect in patients with PHT-CHD.

Aged↗
PubMed1994

Effect of diallyl trisulfide on the activation of T cell and macrophage-mediated cytotoxicity.

At high concentration (50 micrograms/ml), diallyl trisulfide (DATS) had an inhibitory effect on T cell activation (compared with control group, P < 0.05). But at appropriate concentrations (3.125-12.5 micrograms/ml), DATS augmented the activation of T lymphocytes by Con A (compared with control group, P < 0.01). The augmentation of T cell activation by DATS was related to its inhibitory effect on the production of nitric oxide (NO) by macrophages. In a wide range of concentrations (1-100 micrograms/ml), DATS can inhibit the production of NO by macrophages (P < 0.05, P < 0.01). In addition, DATS can antagonize the inhibition of tumor-derived immunosuppressive factors produced by S180 cells and Ehrlich ascitic cancer cells on the activation of T cells, and reduce the inhibitory rate significantly (P < 0.01). DATS, despite its inhibition of the production of NO by macrophages, can significantly enhance the production of hydrogen peroxide (H2O2) by macrophages. When macrophages were pretreated with DATS for 24 h, the cytotoxicity % of macrophages to three tumor cell lines was significantly higher than that in corresponding control group (P < 0.05, P < 0.01). In the presence of both DATS and LPS, the cytotoxicity of macrophages was further enhanced so that the cytotoxicity % of macrophages to tumor cells was significantly higher than either that in the presence of DATS alone or that in the presence of LPS alone (P < 0.05, P < 0.01). These results indicate that DATS can augment the activation of T cells and enhance the anti-tumor function of macrophage, suggesting that DATS may be potentially useful in tumor therapy.

Allyl Compounds↗
PubMed1999

Treatment of hepatitis caused by cytomegalovirus with allitridin injection--an experimental study.

To demonstrate the anti-cytomegalovirus (CMV) activity of allitridin injection (AI), an active anti-infection component of garlic, the in vitro effects of AI on human CMV (HCMV) AD169 and 7 newly isolated strains from patients and its in vivo effect on mice of murine CMV (MCMV) hepatitis were assessed. It was found that plaque reduction rate reached 63.5% after infected cells were treated with cell maximal tolerable concentration (7.5 micrograms/ml) of AI. Meanwhile, flow cytometric analysis for effect of AI on expression of HCMV immediate-early antigen (IEA) showed that IEA inhibition rate of 7 isolated strains was in the range from 43.3% to 66.7%, with a mean of 58.4%, similar to that of AD169 strain (60.5%). On the other hand, in vivo anti-CMV activity of AI was evaluated in terms of liver pathological changes, liver function and viral replication. Six model mice with MCMV hepatitis received the treatment of AI for 2 weeks. The severity of liver damage, levels of sALT and MCMV IE genes expression in liver tissues in the treated mice were significantly lower than those of the corresponding untreated controls. Our results showed that AI had an obvious anti-CMV activity both in vitro and in vivo.

Allyl Compounds↗
PubMed2006

Identification of glutathione conjugates of 2, 3-dibromopropene in male ICR mice.

Hepatotoxic potential of 2, 3-dibromopropene (2, 3-DBPE) and its conjugation with glutathione (GSH) were investigated in male ICR mice. Treatment of mice with 20, 50, and 100 mg/kg of 2, 3-DBPE for 24 h caused elevation of serum alanine aminotransferase and aspartate aminotransferase activities. The hepatic content of GSH was not changed by 2, 3-DBPE. Meanwhile, the GSH content was slightly reduced when mice were treated with 2, 3-DBPE for 6 h and significantly increased 12 h after the treatment. Subsequently, a possible formation of GSH conjugate of 2, 3-DBPE was investigated in vivo. After the animals were treated orally with 20, 50, and 100 mg/kg of 2, 3-DBPE, the animals were subjected to necropsy 6, 12, and 24 h later. A conjugate of S-2-bromopropenyl GSH was identified in liver and serum treated with 100 mg/kg of 2, 3-DBPE by using liquid chromatography-electrospray ionization tandem mass spectrometry. The protonated molecular ions [M+H]+ of S-2-bromopropenyl GSH were observed at m/z 425.9 and 428.1 in the positive ESI spectrum with a retention time of 6.35 and 6.39 min, respectively. In a time-course study in livers following an oral treatment of mice with 100 mg/kg of 2, 3-DBPE for 6, 12, and 24 h, the 2, 3-DBPE GSH conjugate was detected maximally 6 h after the treatment. The present results suggested that 2, 3-DBPE-induced hepatotoxicity might be related with the production of its GSH conjugate.

Administration, Oral↗
PubMed2003

Mechanism studies on the CSI reaction with allyl ethers by varying p-substituent.

We examined the effect of p-substituents in p-substituted cinnamyl methyl ethers and 1-(p-substituted phenyl)allyl methyl ethers with CSI, and confirmed that the CSI reaction of allyl ethers (p-substituted ethers) is a competitive reaction of S(N)i and S(N)1 mechanism according to the stability of the carbocation. And, the only terminal allylic amine was obtained through the migration reaction in thermodynamic reaction condition.

Allyl Compounds↗
PubMed2003

Synthesis of allylthiopyridazine derivatives and inhibition of aflatoxin B1-induced hepatotoxicity in rats.

Five kinds of allylthiopyridazine derivatives were synthesized and their chemoprotective activities examined in rats exposed to aflatoxin B1-toxicant. Rats were pretreated with five allylthiopyridazine derivatives at daily oral doses of 50 mg/kg for 10 consecutive days, and during this period with one or three repeated doses of the potent hepatotoxin, aflatoxin B1. The hepatoprotective effects of the allylthiopyridazine derivatives against aflatoxin B1 (1 mg/kg, three times at intervals of 3 days, i.p., or at 3 mg/kg, once at final days, i.p.) administration were showed the significantly normal as compared with control in body and liver weights. Aspartate aminotransferase and alanine aminotransferase levels were markedly elevated after aflatoxin B1 administration, and pretreatment with allylthiopyridazine derivatives, before aflatoxin B1 administration, resulted in decreased levels of these enzymes. In addition, the allylthiopyridazine derivatives, K6 (3-methoxy-), K8 (3-chloro-), K16 (3-ethoxy-) and K17 (3-n-propoxy), induced elevated hepatic GSH levels. Four kinds of allylthiopyridazine derivatives investigated were effective against aflatoxin B1-induced hepatotoxicity.

Aflatoxin B1↗
PubMed2003

Synthesis and PGE2 inhibitory activity of vinylated and allylated chrysin analogues.

Vinylated and allylated chrysin analogues were prepared as congeners of prenylated flavonoids and evaluated their anti-inflammatory activity. 8-Substituted chrysin analogues were prepared from 2'-hydroxy-3'-iodo-4',6'-dimethoxyacetophenone in 3 steps. 3-Allylated chrysin analogues were prepared from chrysin in 3 steps. Synthesized chrysin analogues (4, 5 and 8) showed moderate inhibitory activities of PGE2 production from LPS-induced RAW 264.7 cells.

Allyl Compounds↗
PubMed1997

The histaminase activity of rat white adipocytes.

OBJECTIVE AND DESIGN: Investigate the reaction conditions which allow the measurement of high affinity histamine oxidation. MATERIAL: Isolated rat white adipocytes. METHODS: The histaminase activity of rat white adipocytes and its inhibition by B24 and MDL 72274 was measured fluorimetrically or radiochemically in different experimental conditions. RESULTS: Histamine oxidation by rat white adipocytes is enhanced by elevated pH and by the presence of bicarbonate ions. Under these conditions the oxidative deamination of histamine by white adipocytes, becomes comparable to that of other histaminases, suggesting that this amine oxidase activity may play a role in the catabolism of histamine in vivo. The specific semicarbazide-sensitive amine oxidase (SSAO) inhibitors MDL 72274 and B24 inhibit the oxidation of both histamine and benzylamine by the adipocyte preparation. CONCLUSIONS: Although there are kinetic differences between the behaviour of these two amine substrates, these results would be consistent with a SSAO being responsible for both activities.

Adipocytes↗
PubMed2002

Involvement of semicarbazide-sensitive amine oxidase-mediated deamination in atherogenesis in KKAy diabetic mice fed with high cholesterol diet.

AIMS/HYPOTHESIS: Semicarbazide-sensitive amine oxidase has been recognised to be a potential risk factor in vascular disorders associated with diabetic complications and to be related to mortality in patients suffering from heart disease. This enzyme, associated with the vascular system, catalyses the deamination of methylamine and aminoacetone, and also acts as an adhesion molecule related to leucocyte trafficking and inflammation. The deaminated products include the toxic aldehydes, formaldehyde and methylglyoxal, respectively, hydrogen peroxide and ammonia. MATERIALS AND METHODS: In this study, the KKAy mouse, a strain possessing features closely resembling those of Type II (non-insulin-dependent) diabetes mellitus has been used to substantiate the hypothesis. Vascular lesions were induced via chronic feeding of a high cholesterol diet. RESULTS: Both MDL-72974A, a selective mechanism-based semicarbazide-sensitive amine oxidase inhibitor and aminoguanidine effectively inhibited aorta semicarbazide-sensitive amine oxidase activity, and caused a substantial increase in urinary methylamine, and a decrease in formaldehyde and methylgloxal levels. Inhibition of semicarbazide-sensitive amine oxidase also reduced oxidative stress, as shown by a reduction of malondialdehyde excretion. Both MDL-72974A and aminoguanidine reduced albuminuria, proteinuria and the number of atherosclerotic lesions in animals fed with a cholesterol diet over a period of treatment for 16 weeks. CONCLUSION/INTERPRETATION: Increased semicarbazide-sensitive amine oxidase-mediated deamination could be involved in the cascade of atherogenesis related to diabetic complications.

Albuminuria↗
PubMed1999

An extractive membrane biofilm reactor for degradation of 1,3-dichloropropene in industrial waste water.

A bacterial biofilm, capable of mineralising a technical mixture of cis- and trans-1,3-dichloropropene (DCPE), was enriched on the biomedium side of an extractive membrane biofilm reactor (EMBR). The membrane separates the biomedium from the industrial waste water, in terms of pH, ionic strength and the concentration of toxic chemicals. The biofilm, attached to a silicone membrane, is able to mineralize DCPE after its diffusion through the membrane. Five bacterial strains with degradation capabilities were isolated from the metabolically active biofilm and further investigated in batch experiments. Two of them, Rhodococcus erythropolis strains EK2 and EK5, can grow with DCPE as the sole carbon source. Pseudomonas sp. EK1 uzilizes cis-3-chloroallylalcohol and cis-3-chloroacrylic acid, whereas the metabolite trans-3-chloroacrylic acid represents a dead-end product of the pathway of this strain. The other two strains, Delftia sp. EK3 and EK4, although unable to grow with DCPE as the carbon source, can transform DCPE and its upper-pathway intermediates at reasonable conversion rates. They may represent helper functions of the biofilm consortium, which mineralised up to 12.5 mmol DCPE per hour per gram of biomass protein. Higher feed rates in the EMBR (up to 15 mmol per hour per 100-l bioreactor volume) and shock loads corresponding to concentrations up to 1.8 mmol l-1 led to a significant increase in the freely floating bacterial biomass in the reactor medium (OD546 = 0.2). At the standard operating feed rate of 1.8 mmol h-1, the free biomass concentration was very low (OD546 = 0.04).

Allyl Compounds↗
PubMed2002

Old yellow enzyme confers resistance of Hansenula polymorpha towards allyl alcohol.

In the methylotrophic yeast, Hansenula polymorpha, peroxisomes are formed during growth on methanol as sole carbon and energy source and contain the key enzymes for its metabolism, one of the major enzymes being alcohol oxidase (AO). Upon a shift of these cells to glucose-containing medium, peroxisomes become redundant for growth and are rapidly degraded via a highly selective process designated macropexophagy. H. polymorpha pdd mutants are disturbed in macropexophagy and hence retain high levels of peroxisomal AO activity upon induction of this process. To enable efficient isolation of PDD genes via functional complementation, we make use of the fact that AO can convert allyl alcohol into the highly toxic compound acrolein. When allyl alcohol is added to cells under conditions that induce macropexophagy, pdd mutants die, whereas complemented pdd mutants and wild-type cells survive. Besides isolating bona fide PDD genes, we occasionally obtained pdd transformants that retained high levels of AO activity although their allyl alcohol sensitive phenotype was suppressed. These invariably contained extra copies of a gene cluster encoding homologues of Saccharomyces carlsbergensis old yellow enzyme. Our data suggest that the proteins encoded by these genes detoxify acrolein by converting it into less harmful components.

Alcohol Oxidoreductases↗
PubMed2004

Garlic metabolites fail to inhibit the activation of the transcription factor NF-kappaB and subsequent expression of the adhesion molecule E-selectin in human endothelial cells.

BACKGROUND: The transcription factor NF-kappaB is suggested to play a pivotal role in atherogenesis by regulating the expression of proinflammatory gene products such as adhesion molecules. Garlic is consumed as food or dietary supplement in order to benefit from its antiatherogenic effect. AIM OF THE STUDY: This study addresses the question whether the garlic metabolites diallyldisulfide (DADS) and allylmercaptane (AM) influence the TNF-alpha-induced activation of NF-kappaB and the NF-kappaB-regulated endothelial gene product E-selectin in human umbilical endothelial cells (HUVECs). METHODS: A putative effect of DADS and AM on NF-kappaB activity was examined by measuring NF-kappaB DNA binding activity by an electrophoretic mobility shift assay (EMSA) and on the NF-kappaB transactivation activity by a luciferase reporter gene assay. In addition, an effect of DADS and AM on the expression of the NF- kappaB-regulated gene product E-selectin was investigated by flow cytometry. RESULTS: We show that neither DADS nor AM (up to 100 micro M) inhibit TNF-alpha (1-10 ng/ml)-induced NF-kappaB DNA binding nor NF-kappaB transactivation activity. The TNF-alpha-induced expression of the endothelial adhesion molecule E-selectin was not reduced in response to DADS or AM. CONCLUSIONS: This study suggests that NF-kappaB is not a major target of garlic metabolites such as DADS or AM.

Allyl Compounds↗
PubMed2006

Bioconversion of ethyl 4-chloro-3-oxobutanoate by permeabilized fresh brewer's yeast cells in the presence of allyl bromide.

Ethyl(R)-4-chloro-3-hydroxybutanoate ((R)-CHBE) are obtained by cetyltrimetylammonium bromide (CTAB) permeabilized fresh brewer's yeast whole cells bioconversion of ethyl 4-chloro-3-oxobutanoate (COBE ) in the presence of allyl bromide. The results showed that the activities of alcohol dehydrogenase (ADH) and glucose-6-phosphate dehydrogenase (G6PDH) in CTAB permeabilized brewer's yeast cells increased 525 and 7.9-fold, respectively, compared with that in the nonpermeabilized cells and had high enantioselectivity to convert COBE to (R)-CHBE. As one of co-substrates, glucose-6-phosphate was preprepared using glucose phosphorylation by hexokinase-catalyzed of CTAB permeabilized brewer's yeast cells. In a two phase reaction system with n-butyl acetate as organic solvent and with 2-propanol and glucose-6-phosphate as co-substrates, the highest (R)-CHBE concentration of 447 mM was obtained with 110-130 g/l of the CTAB permeabilized cells at optimized pH, temperature, feeding rate and the shake speed of 125 r/min. The yield and enantiomeric excess (ee) of (R)-CHBE reached 99.5 and 99%, respectively, within 6 h.

2-Propanol↗
PubMed2004

Inhibition of the benzo[a]pyrene-induced toxicity by allyl sulfides in human epidermal keratinocytes.

Diallyl sulfide (DAS) and diallyl disulfide (DADS) at 25 microg ml(-1)decreased the benzo[a]pyrene (B[a]P)-induced colony growth inhibition of human epidermal keratinocytes. DAS and DADS decreased B[a]P-DNA and B[a]P-protein adducts by 65% and 49-55%, respectively. The B[a]P-induced ethoxyresorufin O-deethylase activity, a marker enzyme for cytochrome P450 1, was decreased from 3 to 1.7-1.9 nmol min(-1) mg(-1) microsomal protein by DAS and DADS treatments. The activity of glutathione S-transferase, a detoxifying enzyme for B[a]P, but was decreased by DADS, but was unaffected by DAS.

Allyl Compounds↗
PubMed2005

Diallyl trisulfide inhibits tumor necrosis factor-alpha expression in inflammed mucosa of ulcerative colitis.

The present study aimed to investigate the effect of diallyl trisulfide (DATS) on tumor necrosis factor (TNF)-alpha expression in inflammed mucosa of ulcerative colitis and its possible mechanism. Colonic biopsies from ulcerative colitis were treated with 0, 1, 5, and 10 microM DATS for 24 hr. Lactate dehydrogenase (LDH) activities and concentrations of TNF-alpha in supernatants were measured. mRNA expressions of TNF-alpha in biopsies were analyzed by RT-PCR. The expression of NF-kappaB P65 in tissues was studied by immunohistochemistry. Concentrations of TNF-alpha in supernatants of biopsies treated with 5 and 10 microM DATS were lower than those of untreated biopsies. There were fewer lamina propria mononuclear cells whose NF-kappaB P65 expression in nuclei was positive, and less mRNA expression of TNF-alpha in biopsies treated with 10 microM DATS than in untreated biopsies. There were no differences in LDH activities in supernatants between tissues treated with DATS and untreated tissues. DATS could downregulate TNF-alpha production and inhibit NF-kappaB activation in lamina propria mononuclear cells of inflammed mucosa, without any effect on the viability of colonic tissue cells.

Adult↗