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PubMed1994

Possible nutritional factors in induced pemphigus.

Today it is generally accepted that every drug that possesses an active thiol group in its molecule is capable of inducing pemphigus. Some plants, in particular those belonging to the Allium group, contain several active compounds with stable disulfide and thiol groups in their molecule. The Allium group contains many important vegetables like onion, leek and garlic. Examples of molecules with an active thiol group are: CH2 = CH-CH2-S-S-CH2-CH = CH2 (diallyl disulfide) or CH2 = CH-CH2-S(O)S-CH2-CH = CH2 (allicin). It is suggested that some foods, in particular vegetables of the Allium group that contain active thiol groups in their molecule, could contribute to the induction of pemphigus. In general, nutritional factors should be added to the list of exogenous factors that are capable of inducing pemphigus.

Allium↗
PubMedDate not supplied

Novel carbamate metabolites of mofegiline, a primary amine monoamine oxidase B inhibitor, in dogs and humans.

Mofegiline or MDL 72,974A ((E)-4-fluoro-beta-fluoromethylene benzene butanamine hydrochloride) is a selective enzyme-activated irreversible inhibitor of monoamine oxidase B, which is under development for use in the treatment of Parkinson's disease. Male beagle dogs were given single p.o. (20 mg/kg) and i.v. (5 mg/kg) doses of [14C]-Mofegiline. Total radioactivity excreted in urine and feces over 96 hr was, respectively, 75.5 +/- 3.8 and 6.3 +/- 3.4% of the dose after p.o. and 67.9 +/- 0.5 and 3.9 +/- 2.4% after i.v. administration. Unchanged drug in urine represented 3% of the dose after po and less than 1% after i.v. administration. Mofegiline was thus extensively metabolized in dogs, and urinary excretion was the major route of elimination of metabolites. HPLC, with on-line radioactivity detection, showed the presence of four major peaks (M1, M2, M3, and M4), representing respectively 50, 9, 5, and 0.5% of the administered dose excreted in 0-24 hr urine. TSP-LC-MS, FAB-MS, and NMR spectra of the purified metabolites were obtained. M1, the major metabolite in dogs, was shown to have undergone defluorination of the beta-fluoromethylene moiety, and one carbon addition. Its structure was confirmed to be a cyclic carbamate. M2 was a N-carbamoyl O-beta-D-glucuronide conjugate of parent drug. The formation of M1 and M2 is likely to involve initial reversible addition of CO2 to the primary amine function. M3 was a N-succinyl conjugate of the parent drug. M4 had also undergone defluorination to yield a urea adduct of an unsaturated alpha, beta aldehyde. Structures of M1 and M3 were further confirmed by comparing their MS and NMR spectra with those of authentic reference compounds. TSP-LC-MS ion chromatograms of human urine, obtained from two male volunteers after p.o. administration of 24 mg of drug, showed selected molecular ion peaks with the same retention time as the metabolites identified in dogs. In humans, these common metabolites represented a similar percentage of the administered dose to that in dogs. The present study demonstrates that NMR, TSP-LC-MS are complementary analytical techniques, which allow structural identification of unhydrolyzed drug conjugates. The formation of carbamates of amine-containing drugs may be more common than previously reported.

Administration, Oral↗
PubMed2005

Growth suppressing effect of garlic compound diallyl disulfide on prostate cancer cell line (PC-3) in vitro.

Prostate cancer is the most predominant cancer in men and prostate cancer related death increases every year. Till date, there is no effective therapy other than androgen ablation therapy. At this stage, induction of apoptosis is considered as a better strategy to control cancer. Previous studies reported that aged garlic extract suppresses cancer growth and enhances immune system against cancer. In the present study, diallyl disulfide, oil soluble organosulfur compound of garlic, was studied for its antiproliferative effect on prostate cancer cells in vitro. The suppression of cell growth was demonstrated by [(3)H]thymidine incorporation assay. Induction of DNA damage was assessed by agarose gel electrophoresis. The results showed that diallyl disulfide inhibited the growth of prostate cancer cells in a dose dependent manner, compared to the control. At 50 microM and 100 microM concentrations, diallyl disulfide induced DNA damage in PC-3 cells. It is concluded that diallyl disulfide, component of aged garlic extract, inhibits proliferation of prostate cancer cells through the induction of apoptosis.

Allyl Compounds↗
PubMed2006

Induction of apoptosis and histone hyperacetylation by diallyl disulfide in prostate cancer cell line PC-3.

Prostate cancer is the most invasive and frequently occurred cancer in men. In the initial stages, it is androgen dependent and the androgen ablation therapy is effective at this stage. In the final stages, it becomes androgen-independent and is unresponsive to androgen ablation therapy. At this stage, induction of apoptosis is considered as a better strategy to control cancer. Histone acetylation and deacetylation are involved in transcriptional activation and transcriptional repression, respectively. Diallyl disulfide (DADS) induced histone hyperacetylation can be correlated with the expression of antiproliferative genes. Induction of apoptosis by DADS has been correlated with histone acetylation. In the present study, DADS, oil soluble organosulfur compound of garlic, has been studied for its effect on histone acetylation and induction of apoptosis in prostate cancer cells in vitro. The induction of apoptosis has been demonstrated by annexin V-FITC binding assay. Extent of apoptosis has been assessed measuring the activity of caspase-3. The results have shown that DADS induced apoptosis in prostate cancer cells in a dose dependent manner. At both 25 and 40 microM concentrations, DADS increased the number of both early and late apoptotic cells. Histone hyperacetylation was also observed in DADS treated cells. It is concluded that DADS, induces apoptosis by influencing histone acetylation in prostate cancer cells.

Acetylation↗
PubMed1989

Pesticide residues in groundwater in The Netherlands: state of observations and future directions of research.

In the first stage of a programme of sampling and analysis for pesticide residues in groundwater in The Netherlands, the upper groundwater below four vulnerable soils was analysed for nearly 2,5 years in eight sampling rounds. Of 18 compounds analysed, including some metabolites, 1,3-dichloropropene, aldicarb, ethoprophos dinoseb, metamitron, atrazine, desethyl- and desisopropylatrazine, metolachlor and ethylenethioureum were repeatedly detected in the groundwater in concentrations above 0.1 micrograms.dm-3, the limit for pesticides in drinking water set by the EC. These observations were made below fields with potatoe-, maize- and bulb flower culture, all on low-humic to moderately humic sandy soils. No residues were found below a cracked light clay on a sandy subsoil. On the locations sampled evidence was found for complete in situ removal in the upper groundwater of 1,3-dichloropropene, high persistence of aldicarb residues and partial in situ degradation of dinoseb.

2,4-Dinitrophenol↗
PubMed2006

Induction of apoptosis and transient increase of phosphorylated MAPKs by diallyl disulfide treatment in human nasopharyngeal carcinoma CNE2 cells.

This study was undertaken to elucidate the effect of diallyl disulfide (DADS), an oil-soluble organosulfur compound found in garlic, in suppressing human nasopharyngeal carcinoma cells. A potent increase (of at least 9-fold) in apoptotic cells has accompanied 1) a decrease in cell viability, 2) a increase of the fraction of S-phase cells by up to 63.8%, and 3) a transient increase of the phospho-p38 and phospho-p42/44 (phosphorylated p38 MAPK and phosphorylated p42/44 MAPK) in a time- and concentration-dependent manner. These results indicate that DADS can induce apoptosis in human nasopharyngeal carcinoma cells via, at least partly, S-phase block of the cell cycle, related to a rise in MAPK phosphorylation.

Allyl Compounds↗
PubMed2002

Differential effects of garlic oil and its three major organosulfur components on the hepatic detoxification system in rats.

The objective of this study was to compare the modulatory effect of garlic oil and its three organosulfur compounds, diallyl sulfide (DAS), diallyl disulfide (DADS), and diallyl trisulfide (DATS), on rat hepatic detoxification enzyme activity, and protein and mRNA expression. Rats were orally administered garlic oil (80 or 200 mg/kg bw), DAS (20 or 80 mg/kg bw), DADS (80 mg/kg bw), or DATS (70 mg/kg bw) three times a week for 6 weeks. Control rats received corn oil. According to the results, garlic oil and DAS in dosages of 200 and 80 mg/kg bw, respectively, significantly increased pentoxyresorufin O-dealkylase (PROD) activity as compared with the that of the control rats (P < 0.05). In contrast, N-nitrosodimethylamine demethylase activity in rats that received DADS and DATS was significantly lower than that in the control rats (P < 0.05). Ethoxyresorufin O-deethylase and erythromycin demethylase activities were not influenced by garlic oil, DAS, DADS, or DATS. To the phase II enzyme, garlic oil, DADS, and DATS significantly increased the glutathione S-transferase (GST) activity toward ethacrynic aicd (P < 0.05). Immunoblot assay showed that the protein contents of cytochrome P450 1A1, 2B1, and 3A1 were increased by garlic oil and each of three allyl sulfides, and the change among the allyl sulfides was in the order of DAS > DADS > DATS. The placental form of GST (PGST) level was also increased by garlic oil and the three allyl sulfides, but the increase among the allyl sulfides was DATS congruent with DADS > DAS. P450 2E1, however, was suppressed by each garlic component. Northern blot results indicated that the changes in P450 1A1, 2B1, 3A1, and PGST mRNA levels by garlic components were similar to those noted in the protein levels. These results indicate that the modulatory effect of garlic oil on hepatic drug-metabolizing enzymes can be attributed to its three major allyl sulfide components DAS, DADS, and DATS. These three allyl sulfides vary in modulatory activity, and this variation is related to the number of sulfur atoms in the molecule.

Allyl Compounds↗
PubMed1992

Inhibition of benzo[a]pyrene-induced bone marrow micronuclei formation by diallyl thioethers in mice.

Diallyl thioethers (DATEs), naturally occurring compounds present in garlic, were investigated for their putative ability to inhibit benzo[a]pyrene-induced genotoxicity in ICR and C3H strains of mice. The mouse bone marrow micronucleus assay was used as an indicator of in vivo genotoxicity. A dose of 0.67 mmol total DATEs/kg body weight inhibited formation of micronucleated polychromatic erythrocytes (MPCEs) by 24%, and 0.33 mmol DATEs inhibited formation of MPCEs by 45%. Possibly the toxicity of DATEs accounted for less inhibition with the higher dose. Formation of MPCEs were inhibited only slightly by DATEs in C3H mice. These results indicate that the mouse bone marrow micronucleus assay can be used to identify organosulfur components of garlic that inhibit genotoxicity.

Allyl Compounds↗
PubMed1994

Pharmacodynamics of MDL 72974A: absence of effect on the pressor response to oral tyramine.

MDL 72974A, a new irreversible selective inhibitor of monoamine oxidase (MAO)-B which is not metabolized to amphetamine-like compounds, is currently being developed for the treatment of Parkinson's disease. In this double blind, placebo controlled randomized study 24 healthy volunteers (n = 6/dose) received single oral doses of placebo, 1, 12 or 24 mg of MDL 72974A qd over two weeks. Sensitivity to orally administered tyramine was determined under fasting conditions before and after drug administration and the doses of tyramine yielding a 30 mmHg increase of SBP (PD30) compared. The 2-fold increase of tyramine sensitivity at end of treatment seen at all MDL 72974A dose levels, however, is within the variability range of the tyramine pressor response. MDL 72974A selectively inhibits MAO-B at doses up to 24 mg orally and has a favourable safety profile.

Administration, Oral↗
PubMed1994

Study of the genotoxic activity of five chlorinated propanones using the SOS chromotest, the Ames-fluctuation test and the newt micronucleus test.

Three short-term assays (the SOS chromotest, the Ames-fluctuation test and the newt micronucleus test) were carried out to evaluate the genotoxicity of five chlorinated propanones identified in several chlorinated waters (monochloropropanone, 1,1-dichloropropanone, 1,3-dichloropropanone, 1,1,1-trichloropropanone and 1,1,3-trichloropropanone). In the SOS chromotest, all the compounds except monochloropropanone were found to induce primary DNA damage in Escherichia coli. With the fluctuation test, all five chloropropanones showed mutagenic activity on Salmonella typhimurium strain TA100. The newt micronucleus assay detected a clastogenic effect on the peripheral blood erythrocytes of Pleurodeles waltl larvae only for 1,3-dichloropropanone and 1,1,3-trichloropropanone. Moreover, two structure-activity relationships are noticeable: (1) chloropropanones with chlorine substituents on both carbon positions (1,3-DCP and 1,1,3-TCP) are by far more genotoxic than chloropropanones substituted only on one carbon position (1,1-DCP and 1,1,1-TCP); (2) the increase of the number of chlorine substituents decreases the mutagenic activity (fluctuation test) of the chlorinated propanones studied.

Acetone↗
PubMed1989

Role of ornithine decarboxylase in diallyl sulfide inhibition of colonic radiation injury in the mouse.

Diallyl sulfide (DAS), a major flavor component of garlic (Allium sativum) that has previously been shown to inhibit colon carcinogenesis in experimental animals, was investigated for its ability to reduce acute colonic mucosal injury following gamma-ray exposure. Female C57BL/6J mice received either vehicle or DAS (200 mg/kg) by gavage 3 h prior to a single, whole body dose of radiation from a 60Co source. After 24 h, animals were killed and their colons were excised, fixed, and sectioned. DAS significantly inhibited nuclear aberration formation (a measure of nuclear damage) over a radiation dose range of 0.5 to 10 Gy. The degree of protection was related to the dose of DAS and the compound was ineffective if given after irradiation. Following 6 Gy, both DNA synthesis in vivo (measured by [3H]thymidine incorporation into DNA) and the activity of ornithine decarboxylase (an important regulator of DNA synthesis) were elevated for more than 14 days. The induction of both these parameters was significantly suppressed by administering DAS prior to radiation exposure. To determine the role of polyamine synthesis in affecting the severity of radiation damage in the large intestine, difluoromethylornithine, an ornithine decarboxylase inhibitor, was administered in the drinking water of the animals 24 h prior to and following radiation treatment. Difluoromethylornithine abolished the ability of DAS to reduce colonic nuclear damage caused by radiation exposure. Thus DAS protects against colonic radiation injury via a polyamine-dependent pathway.

Allyl Compounds↗
PubMed2004

Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma.

Low-density lipoprotein (LDL) and plasma were isolated from patients with non-insulin-dependent diabetes. The protective effects of six organosulfur compounds (DAS, diallyl sulfide; DADS, diallyl disulfide; SAC, S-allylcysteine; SEC, S-ethylcysteine; SMC, S-methylcysteine; SPC, S-propylcysteine) against further oxidation and glycation in these already partially oxidized and glycated samples were studied. DAS and DADS showed significantly greater oxidative-delaying effects than four cysteine-containing compounds in both partially oxidized LDL and plasma samples (P < 0.05). However, cysteine-containing agents were superior to DAS and DADS in delaying glycative deterioration in already partially glycated LDL (P < 0.05). The observed delays of oxidative and glycative effects from each agent were significantly concentration-dependent (P < 0.05). Furthermore, six organosulfur agents significantly decreased the loss of catalase and glutathione peroxidase activities in plasma and increased alpha-tocopherol retention in LDL and plasma (P < 0.05). These results suggested that the use of these organosulfur agents derived from garlic at these concentrations could protect partially oxidized and glycated LDL or plasma against further oxidative and glycative deterioration, which might benefit patients with diabetic-related vascular diseases.

Allyl Compounds↗
PubMed1998

N2,7-bis(1-hydroxy-2-oxopropyl)-2'-deoxyguanosine: identical noncyclic adducts with 1,3-dichloropropene epoxides and methylglyoxal.

cis- and trans-1,3-dichloropropene epoxides (1,3-D-epoxides) are proposed to be the penultimate or ultimate genotoxic metabolites of the major soil fumigant nematicide 1,3-dichloropropene. The 1, 3-D-epoxide isomers and the potential aldehydes from their degradation readily form adducts with 2'-deoxyguanosine (dGuo) but not with 2'-deoxyadenosine or 2'-deoxycytidine. The reaction of dGuo with the 1,3-D-epoxides (1:20 molar equiv) in phosphate buffer at pH 7.4 for 24 h at 37 degreesC results in complete conversion to four adducts that can be separated by HPLC with the same UV spectra and electrospray (ES)/MS molecular ion and fragmentation patterns. These adducts contain no chlorine and are identical to those obtained more rapidly with methylglyoxal in place of the 1,3-D-epoxides. The four isomeric methylglyoxal adducts with dGuo were proposed originally by others to be the cyclic adducts 1,N2-(1, 2-dihydroxy-2-methyl)ethano-dGuo, but they are reassigned here as the four diastereomers of the noncyclic bis adducts N2, 7-bis(1-hydroxy-2-oxopropyl)-dGuo. The assignments are based on HPLC/UV and HPLC/ES/MS experiments and 1H NMR spectral analysis of the first of the four adducts eluted with HPLC. Acid-catalyzed depurination converts the four dGuo derivatives to the two corresponding isomers of N2,7-bis(1-hydroxy-2-oxopropyl)guanine, assigned by ES/MS and 1H and 13C NMR. Although identical adducts are formed from dGuo with the 1,3-D-epoxides or methylglyoxal, the latter alpha,beta-dicarbonyl compound is not an intermediate in the reaction; instead, the 1,3-D-epoxides hydrolyze to 3-chloro-2-hydroxypropanal which adds to dGuo at N2 and N7. The adducts dehydrochlorinate, in a rate-limiting reaction, thereby giving the same end products obtained on direct reaction with methylglyoxal. Thus, 3-chloro-2-hydroxypropanal (not the 1, 3-D-epoxides or methylglyoxal) is the derivatizing agent for dGuo and therefore probably the mutagenic agent on 1,3-D bioactivation. On the basis of the dGuo model studied here, the DNA adducts of 1, 3-D and its epoxides may be the same as those with methylglyoxal [Vaca, C. E., Fang, J.-L., Conradi, M., and Hou, S.-M. (1994) Carcinogenesis 15, 1887-1894].

Allyl Compounds↗
PubMed2006

Removal of E. coli from water using surface-modified activated carbon filter media and its performance over an extended use.

Modification of activated carbon (AC) by aluminum hydroxychloride (AHC), and diatomaceous earth by zinc hydroxide changed the zeta potentials of these filter media from negative to positive. The modification method is amenable to room temperature, and eliminates the essential requirement of strong base treatment for making metal hydroxide coated filter media. Solid-state MAS 27Al NMR spectra suggested the presence of Al13-mer in the AHC-treated AC. AHC-modified AC samples were further treated with silver halide, and two antibacterial compounds to prevent microbial growth on filter media. In situ precipitation of silver bromide on AC resulted in formation of nanosized AgBr crystals. Bacteria removal performances of the modified media were tested in columns. For the first time, we demonstrated that only 30 g of either AHC-treated AC (60 x 200 mesh) or nano AgBr supported AC could provide >6 log E. coli removal over approximately 1000 L when the input water had a bacterial load of 10(7) CFU/mL. The filter media were robust enough to perform even when water was passed at superficial velocities 3-10 times the typical velocity (6 cm/min) of water treatment processes. Metal leaching from the modified media was found to be less than the USEPA specified Maximum Contaminant Level.

Allyl Compounds↗
PubMed2000

Antithrombotic and antineoplastic effects of phyto-organosulfur compounds.

The antiplatelet activity of methyl allyltrisulfide (MATS), a component commonly present in steam-distilled garlic oil, has been demonstrated by the authors. MATS inhibits arachidonic acid cascade at the reaction site with PGH synthase. However, this enzyme catalyzes two successive reactions, from arachidonic acid to PGG2, and from PGG2 to PGH2. The present study revealed that MATS inhibited the latter reaction. In addition, our recent findings that to a promyelocytic leukemia cell HL60, Allium oils shows marked anti-neoplastic effects representing both growth suppression and differentiation activities are described. The garlic oil and onion oil showed almost equal ability in inducing the proliferation, which measured either by nitroblue-tetrazolium reducing activity assay or by flow cytometry for detecting CD11b expression. The combination use of one of these oils with all-trans retinoic acid or with dimethyl sulfoxide lead to the marked differentiation of the cells, and their effects were estimated to be synergistic.

Allium↗
PubMed2001

Relative activities of organosulfur compounds derived from onions and garlic in increasing tissue activities of quinone reductase and glutathione transferase in rat tissues.

There is evidence that onions and garlic protect against cancer in humans. It has been suggested that this effect is due to the organosulfur compounds in these vegetables and that these substances act through induction of phase II detoxification enzymes. In the present studies, we have compared the ability of diallyl sulfide, dially disulfide, and diallyl trisulfide, compounds that are derived from garlic, to increase the activity of the phase II enzymes quinone reductase and glutathione transferase in a variety of rat tissues. We have also examined the onion-derived substances, dipropyl sulfide, dipropyl disulfide, dipropenyl sulfide, and dipropenyl disulfide, under identical conditions. Diallyl trisulfide and diallyl disulfide were potent inducers of the phase II enzymes. Dipropenyl disulfide was much less active, while little effect on enzyme activity was seen in animals dosed with dipropyl disulfide. Diallyl sulfide and dipropyl sulfide were weak inducers of quinone reductase and glutathione transferase, but dipropenyl sulfide was very active, with an effect similar to that of diallyl disulfide. It is possible that diallyl disulfide and diallyl trisulfide are important in the anticancer action of garlic, while dipropenyl sulfide could be involved in the beneficial action of onions.

Allyl Compounds↗
PubMed1998

Differential induction of NAD(P)H:quinone oxidoreductase by anti-carcinogenic organosulfides from garlic.

This study was undertaken to elucidate the mechanism of organ specificity and differential efficacy of garlic organosulfides (OSCs) [diallyl sulfide (DAS), diallyl disulfide (DADS), diallyl trisulfide (DATS), dipropyl sulfide (DPS) and dipropyl disulfide (DPDS)] in preventing benzo(a)pyrene (BP)-induced tumorigenesis in mice. The results of the present study reveal a good correlation between chemopreventive efficacies of garlic OSCs and their inductive effects on the expression of NAD(P)H:quinone oxidoreductase (NQO), an enzyme implicated in the detoxification of activated quinone metabolites of BP. Treatment of mice with DADS and DATS, which are potent inhibitors of BP-induced forestomach tumorigenesis, resulted in a statistically significant increase (2.4- and 1.5-fold, respectively) in forestomach NQO activity. In addition, DADS and DATS were much more potent inducers of forestomach NQO activity than DAS, which is a weak inhibitor of BP-induced forestomach tumorigenesis than the former compounds. Propyl-group containing OSCs (DPS and DPDS), which do not inhibit BP-induced tumorigenesis, did not affect forestomach NQO activity. Similar to forestomach, a good correlation was also observed between effects of these OSCs against BP-induced pulmonary tumorigenesis and their effects on NQO expression in the lung. For example, treatment of mice with DAS, which is a potent inhibitor of BP-induced pulmonary tumorigenesis, resulted in about 3.2-fold increase in pulmonary NQO activity. On the other hand, this activity was increased by about 1.5-fold upon DATS administration, which does not inhibit BP-induced cancer of the lung. In conclusion, our results suggest that induction of NQO may be important in anti-cancer effects of garlic OSCs.

Allyl Compounds↗
PubMedDate not supplied

Antiproliferative effect of diallyl disulfide (DADS) on prostate cancer cell line LNCaP.

Garlic has been used throughout the world to treat coughs, toothache, earache, dandruff, hypertension, hysteria, diarrhoea, dysentery, diptheria, vaginitis and many other conditions. Garlic contains a complex mixture of oil and water-soluble organosulfur compounds. Diallyl disulfide (DADS), an oil-soluble constituent of garlic seems to be effective in reducing tumour cells originating from colon, lung and skin. Hence our present study focuses on the dose-dependent effect of DADS on an androgen-dependent prostate cancer cell line. Various concentrations of DADS ranging from 25 to 100 microM were given to LNCaP cells and the activity of lactate dehydrogenase (LDH) prostatic acid phosphatase (PAcP) and the level of prostate specific antigen were studied. DADS reduced the secretory activity of LNCaP cells with the gradual increase in dosage. DADS was found to act as a good antiproliferative agent, which was confirmed by proliferation assay. DADS also induced apoptosis and nuclear segmentation in the higher doses.

Acid Phosphatase↗