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PubMed2000

Antifungal activity of magnolol and honokiol.

Two neolignan compounds, magnolol (5,5'-diallyl-2,2'-dihydroxybiphenyl, 1) and honokiol (5,5'-diallyl-2,4'-dihydroxybiphenyl, 2), were isolated from the stem bark of Magnolia obovata and evaluated for antifungal activity against various human pathogenic fungi. Compound 1 and 2 showed significant inhibitory activities against Trichophyton mentagrophytes, Microsporium gypseum, Epidermophyton floccosum, Aspergillus niger, Cryptococcus neoformans, and Candida albicans with minimum inhibitory concentrations (MIC) in a range of 25-100 microg/ml. Therefore, compound 1 and 2 could be used as lead compounds for the development of novel antifungal agents.

Antifungal Agents↗
PubMed2003

Synthesis of new sugar amino acid derivatives of D-glucosamine.

The synthesis of several new sugar amino acid derivatives of 2-acetamido-2-deoxy-D-glucose, bearing a C-glycosyl functionality as building blocks for the design and synthesis of natural glycoconjugates mimetics, is described. These compounds were prepared from the readily accessible per-benzylated amino C-allyl glucopyranosyl compounds, with TMSOTf/Ac(2)O-mediated selective acetolysis of the 6-O-benzyl group as the key step.

Acetylglucosamine↗
PubMed2003

The reaction of allyl and benzylarsonic acids with thiols: mechanistic aspects and implications for dioxygen activation by trivalent arsenic compounds.

The reaction of allyl and benzylarsonic acids with thiophenol gives not only the expected diphenyl alkyldithioarsonites and diphenyl disulfide but also various other compounds arising from the decomposition at the arsenic(V) oxidation level (the arsonic acids) by thiophenol and at the arsenic(III) oxidation level (mainly the alkyldithioarsonites) by thiophenol and by dissolved dioxygen. The reaction of these arsonic acids with 4-nitrothiophenol, which is not oxidized by dioxygen, revealed that the arsenic(III) of these alkyldithioarsonites is the active atom towards dioxygen. However, the reaction of allyl, benzyl, and 2-picolylarsonic acids with DL-penicillamine gives the expected products with no or very small oxidative decomposition. The decomposition pathways of allyl and benzylarsonic acids were elucidated. The results are briefly discussed in the contexts of the use of arsonic acids in chemotherapy and the ability of arsenic(III) compounds to generate reactive oxygen species.

Allyl Compounds↗
PubMed2004

Multinuclear magnetic resonance and molecular modeling investigations as unambiguous methods for the determination of silacycle 3D structures.

An unexpected six-membered silacycle was obtained using ring-closing metathesis of diallylsilane 3. The ring size of the compound formed was derived using a 2D 13C-13C inadequate experiment. All proton and carbon-13 resonances were assigned from classical 2D NMR experiments and the proton coupling pattern was clarified. Molecular modeling calculation was then applied using NMR data as constraints, giving the 3D structure of the synthesized compound.

Algorithms↗
PubMed1988

Effects of organosulfur compounds from garlic and onions on benzo[a]pyrene-induced neoplasia and glutathione S-transferase activity in the mouse.

In the present study, eight organosulfur compounds from garlic and onions were studied for their inhibitory effects on benzo[a]pyrene (BP)-induced neoplasia of forestomach and lung of female A/J mice when administered 96 and 48 h prior to carcinogen challenge. These compounds had one, two or three linearly connected sulfur atoms. They included the four allyl group-containing derivatives: allyl methyl trisulfide (AMT), allyl methyl disulfide (AMD), diallyl trisulfide (DAT), and diallyl sulfide (DAS), and also four corresponding saturated compounds in which propyl groups were substituted for the allyl groups. All four allylic compounds inhibited BP-induced neoplasia of the forestomach. The saturated analogs were almost without inhibitory activity, indicating the importance of the allyl groups. DAT, which contains two allyl groups, was more potent than AMT, which contains only one allyl group, thus providing further evidence for the role of allyl groups in the inhibitory effects observed. DAS and AMD, but not DAT or AMT, inhibited pulmonary adenoma formation. The fact that in the lung the monosulfide and disulfide inhibited, but the trisulfide did not inhibit, indicates that the number of sulfur atoms in the molecule can control the organ sites at which protection against carcinogenesis will occur. All four allylic compounds induced increased glutathione S-transferase (GST) activity in the forestomach, but varied in their capacity to induce GST in lung, liver and small bowel. Their saturated analogs produced little or no induction. In evaluating relationships between diet and cancer, it would be useful to consider the possible role of garlic and onion organosulfur compounds as protective agents. In addition, further studies of this class of chemicals might lead to the identification and development of useful new chemopreventive compounds.

Allium↗
PubMed1996

Protective effects of garlic and related organosulfur compounds on acetaminophen-induced hepatotoxicity in mice.

In previous studies, we have demonstrated that diallyl sulfide, a flavor component of garlic, protects against chemically induced hepatotoxicity. The present study examined the activities of fresh garlic homogenates (FGH) and related organosulfur compounds in the protection against acetaminophen (APAP)-induced hepatotoxicity and the possible mechanisms involved in this protection. When FGH (5 g/kg) was administered to Swiss-Webster mice 2 hr prior to, or immediately after, an APAP treatment (0.2 g/kg), APAP-induced hepatotoxicity was essentially prevented as indicated by serum levels of alanine aminotransferase and lactate dehydrogenase and by liver histopathology. Partial protection was observed with a lower dose of FGH (0.5 g/kg). FGH also prevented APAP-induced hepatic glutathione depletion in a dose-dependent manner. FGH significantly inhibited the formation of APAP-oxidized metabolites, as indicated by decreased plasma levels of oxidized APAP metabolites. The amount of APAP excreted as oxidized metabolites in the 24 hr urine samples was also significantly lower in the mice pretreated with FGH. FGH supernatant inhibited cytochrome P450-dependent APAP oxidation in microsomal incubations. The results suggest that the protection against APAP-induced hepatotoxicity by FGH is mainly due to its inhibition of P450-mediated APAP bioactivation. Several garlic-derived organosulfur compounds and structurally related compounds were examined for their abilities to protect against APAP-induced hepatotoxicity. An S-allyl structure appears to be a common feature for most sulfides to inhibit P450 2E1-dependent activity and to display good protective activities.

Acetaminophen↗
PubMed1990

Glutathione S-transferase subunit induction patterns of Brussels sprouts, allyl isothiocyanate and goitrin in rat liver and small intestinal mucosa: a new approach for the identification of inducing xenobiotics.

Effects of Brussels sprouts (2.5-30%), allyl isothiocyanate (0.03 and 0.1%) and goitrin (0.02%), in the diet, on the glutathione S-transferase subunit pattern in the liver and small intestinal mucosa of male Fisher rats were investigated. A statistically significant linear relationship was found between the amount of Brussels sprouts in the diet and the induction of glutathione S-transferase subunits in two experiments. Increases in total activity of glutathione S-transferases towards 1-chloro-2,4-dinitrobenzene ranged from about 15% (2.5% Brussels sprouts in the diet) to 180% (30% Brussels sprouts in the diet) in the liver, and from 3% (2.5% Brussels sprouts) to 150% (30% Brussels sprouts) in the small intestinal mucosa. There were similar increases in the total amounts of glutathione S-transferase subunits. In the first experiment, when the average sinigrin and progoitrin levels found in the sprouts were 1835 and 415 mumol/kg, respectively, subunit induction patterns in both the liver and the small intestinal mucosa were very similar to the pattern observed after feeding allyl isothiocyanate. In the second experiment, when the average sinigrin level found in the sprouts was as low as the progoitrin level (both about 540 mumol/kg), a goitrin-like induction pattern was observed. The most pronounced difference between the glutathione S-transferase subunit induction patterns due to administration of allyl isothiocyanate and goitrin is the much stronger enhancement of subunit 2 by allyl isothiocyanate. The induction patterns of both experiments indicate that in Brussels sprouts at least two compounds, probably allyl isothiocyanate and goitrin, are responsible for the induction of glutathione S-transferases.

Animals↗
PubMed2005

Internally solvated cyclopentadienyllithium compounds: structural integrity of the Cp-Li+ moiety. NMR, dynamics, X-ray crystallography, and calculations.

[Structure: see text]. N(CH2CH2OCH3)2 are as follows: T = CHCH(CH3)2, 6; T = (CH2)2, 10; T = (CH2)3, 14. The results of NOE NMR experiments for 6, 10, and 14 together with X-ray crystallography of 14 support internally coordinated monomeric structures for all three compounds. Models have been constructed for 6, 10, and 14 from modifications of an internally solvated allylic lithium compound at the B3LYP level of theory using basis set 6-311G*. The resulting structural features are very similar to those obtained from the NMR and crystallographic data. In addition, 13C NMR shifts obtained with the GIAO procedure using the results of the B3LYP/6-311G* calculations are closely similar to the experimental shifts, which validate B3LYP as a suitable model for these compounds. The Li+ centroid distance of ca. 1.9 A to 2.0 A obtained for 6, 10, and 14 is common to most crystallographic data for externally solvated Cp-Li+ compounds as well as one which incorporates a (CpLiCp)- triple ion. It is concluded that the ligand tether and the stereochemistry around Li+ accommodate to maintain the structural integrity of Cp-Li+. NMR and crystallography show 14 to be chiral. Carbon-13 NMR line shape changes are attributed to inversion via a lateral wobble mechanism with DeltaH++ = 6 kcal x mol(-1) and DeltaS++ = -2 eu. It is also shown that a 6,6-dimethylfulvene is deprotonated at methyl by LiN(CH2CH2OCH3)3 as well as by butyllithium in the presence of PMDTA producing isopropenyl Cp-Li+ compounds 24 and 25, respectively. NMR line shape changes of the sample containing 24 have been qualitatively interpreted to result from a combination of fast transfer of coordinated ligand between faces of the carbanion plane as well as a lithium-exchange process.

Journal Article↗
PubMed2004

Effects of Magnolol and Honokiol on the activities of streptococcal glucosyltransferases both in solution and adsorbed on an experimental pellicle.

AIMS: To investigate the inhibitory effects of Magnolol and Honokiol on the activity of streptococcal glucosyltransferases (Gtfs). METHODS AND RESULTS: The effect of Magnolol and Honokiol that inhibits the activities of streptococcal GtfB, GtfC, GtfD and GtfS was explored with standard assays. The results showed that both samples can efficiently inhibit the activity of all Gtfs in solution (66.4-96.3%) and adsorbed on the surface of saliva-coated hydroxyapatite (sHA) beads (65.5-92.7%) at concentrations between 1.25 and 5.0 mg ml(-1). Furthermore, Magnolol had a stronger inhibition of four kinds of Gtfs than Honokiol both in solution and adsorbed on the surface of sHA beads at concentrations between 0.04 and 0.63 mg ml(-1) (P < 0.05). CONCLUSIONS: Magnolol had significant effects on the activities of streptococcal Gtfs. SIGNIFICANCE AND IMPACT OF THE STUDY: Magnolol as a natural herb can be developed into a new oral hygiene product to prevent plaque formation.

Adsorption↗
PubMed2002

Alleviation of cyclophosphamide-induced urotoxicity by naturally occurring sulphur compounds.

Treatment of Swiss albino mice with naturally occurring sulphur compounds such as Diallyl sulphide (DAS) (500 microg/dose/animal, i.p) and Diallyl Disulphide (DADS) (250 microg/dose/animal, i.p) for five days along with cyclophosphamide (CTX) (1.5 mmol/kg.body.wt; i.p) reduced the CTX induced urotoxicity. Morphological analysis of the urinary bladders of the CTX treated group showed severe inflammation and dark colouration whereas the sulphur compounds treated group showed almost normal bladder morphology. Treatment with DAS and DADS was found to reduce the urine urea N2 level DAS (15.31+/-0.01 g/l), DADS (12.38+/-0.17 g/l) 4 hrs after CTX administration which was elevated in the CTX alone treated group (26.87+/-1.86 g/l). Urine protein level, which was enhanced drastically (8.66+/-0.47 g/l) after the CTX treatment, was significantly reduced (2.9+/-0.25 g/l) by the treatment with DADS. Similarly GSH content (which was drastically reduced by the CTX administration) in both bladder (0.87+/-0.1 nmol/mg protein) and liver (2.47+/-0.6 nmol/mg protein) was enhanced significantly (P<0.001) by the treatment with DAS and DADS both in bladder (DAS--1.56+/-0.17 nmol/mg protein; DADS--2.65+/-0.21 nmol/mg protein) and liver (DAS--5.30+/-0.07 nmol/mg protein; DADS--6.93+/-0.06 nmol/mg protein). Histopathological analysis of the bladder of the CTX alone treated group showed severe necrosis of the tissue whereas the sulphur compounds treated group showed normal bladder pathology.

Allyl Compounds↗