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The manufacturing process of paperboard food packaging can produce small quantities of 3-chloro-1,2-propanediol (3-MCPD or 3-monochloropropane-1,2-diol) when wet-strength resins containing epichlorohydrin are used. 3-MCPD is from the same family as 1,3-dichloro-2-propanol (1,3-DCP), which is known to cause cancer in animals. 3-MCPD has been found in acid hydrolyzed vegetable protein, Asian sauces and paperboard for food contact. In this investigation, we conducted extraction studies to measure 3-MCPD migration into food simulant solvents from the food contact side of polyethylene extrusion-coated paperboard beverage cartons and aqueous extractions of cut pieces from the entire paperboard...

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A new triterpenoid, bruceajavanin C (1), together with bruceosides A and B (2 and 3), bruceines D and E (4 and 5), yadanziosides A and G (6 and 7), (20R)-O-(3)-alpha-L-arabinopyranosylpregn-5-ene-3beta,20-diol (8), and alpha-D-glucopyranoside, (3beta, 20R)-3-hydroxypregn-5-en-20-yl (9) were isolated from the aerial parts of Brucea javanica. The structure of 1 was elucidated on the basis of 2D-NMR spectroscopic analysis. In addition, compounds 1, 3, 4, 5, and 6 exhibited mild inhibitory effect on NO production in LPS-stimulated RAW264...

Synopsis The role of antioxidants in preventing nitrosamine (N-nitroso diethanolamine) formation in shampoos and skin creams and the levels of Bronopol (2-bromo, 2-nitropropane-1, 3-diol) addition in relation to the resultant levels of N-nitroso compounds have been studied. The addition of 0.05% BHT, alpha-tocopherol or ascorbate was effective in preventing nitrosamine formation (limit of determination: 2.5 mug kg(-1)) in products preserved with 0.01% Bronopol. At 0.05% Bronopol, 0.2% of all three antioxidants was effective in preventing nitrosamine formation but at 0...

A method for selective monofunctionalition of readily available cyclodextrin diols (2(A-F),3(A-F),6(B,C,E,F)-hexadeca-O-benzyl-alpha-cyclodextrin and 2(A-G),3(A-G),6(B,C,E-G)-nonadeca-O-benzyl-beta-cyclodextrin) by regioselective nucleophilic opening of their cyclic sulfates is presented. Although the A and D products are nonequivalent in beta-cyclodextrin, only the A product is formed.

17-beta-Estradiol (E2) is a steroid hormone involved in numerous bodily functions, including several brain functions. In particular, E2 is neuroprotective against excitotoxicity and other forms of brain injuries, a property that requires the extracellular signal-regulated kinase (ERK) pathway and possibly that of other signaling molecules. The mechanism and identity of the receptor(s) involved remain unclear, although it has been suggested that E2 receptor alpha (ERalpha) and G proteins are involved. We, therefore, investigated whether E2-mediated neuroprotection and ERK activation were linked to pertussis toxin (PTX)-sensitive G-protein-coupled effector systems...

OBJECTIVE: To evaluate the association between lifestyle and dietary factors and serum concentrations of androgens in middle-aged healthy men. METHODS: We conducted a cross-sectional analysis of the association of lifestyle factors with circulating concentrations of androstenedione (A-dione), 3-alpha-androstanediol glucuronide (A-diol-g), testosterone (T), SHBG (sex hormone-binding globulin), and free testosterone (FT) among 636 men in the European Prospective Investigation into Cancer and Nutrition...

A series of alpha-cyclodextrin derivatives containing a 3, 4 or 5 membered ether-linked bridge between the 6A and 6D oxygen atoms, with and without a ketone, were prepared. The synthesis used perbenzylated alpha-cyclodextrin A,D-diol as a starting material upon which O-alkylation and further modifications led to the di-O-(buta-1,4-diyl), the di-O-(penta-1,5-diyl) and the di-O-(buta-2-on-1,4-diyl) derivatives, which were debenzylated, and compared with the previously reported di-O-(propa-2-on-1,3-diyl) derivative...

INTRODUCTION: Sexual dysfunction after breast cancer has been attributed to a variety of treatment associated and psychological factors. Data on the role of a treatment-induced decrease of testosterone for the development of sexual problems in breast cancer survivors have remained inconclusive. However, androgen metabolites constitute a more reliable measure for total androgen activity. AIM: To measure levels of total androgen activity in breast cancer patients and to investigate relevant predictors of sexual dysfunction after breast cancer...

The conformation of the 1 R,2 S,3 R,4 S-benzo[ c]phenanthrene- N (2)-dG adduct, arising from trans opening of the (+)-1 S,2 R,3 R,4 S- anti-benzo[ c]phenanthrene diol epoxide, was examined in 5'- d(ATCGC XCGGCATG)-3'.5'-d(CATGCCG CGCGAT)-3', where X = 1 R,2 S,3 R,4 S-B[ c]P- N (2)-dG. This duplex, derived from the hisD3052 frameshift tester strain of Salmonella typhimurium, contains a (CG) 3 iterated repeat, a hotspot for frameshift mutagenesis. NMR experiments showed a disconnection in sequential NOE connectivity between X (4) and C (5), and in the complementary strand, they showed another disconnection between G (18) and C (19)...

PURPOSE: Cigarette smoking is a risk factor for renal cell carcinoma. BPDE (benzo[alpha]pyrene diol epoxide) (Midwest Research Institute, Kansas City, Missouri), which is a major constituent of cigarette smoke, induces 3p aberrations that are associated with susceptibility to other smoking associated cancers. Because chromosome 3p deletions are known to be the most frequent genetic alterations in renal cell carcinoma, we tested whether 3p sensitivity to BPDE predicts susceptibility to renal cell carcinoma...

OBJECTIVE: To evaluate mifepristone (RU-486) in patients with castration-resistant prostate cancer (CRPC), with a correlative assessment of serum androgens and androgen metabolites PATIENTS AND METHODS: The androgen receptor (AR) is critical in the development and progression of prostate cancer, but available antiandrogens incompletely abrogate AR signalling. Mifepristone is a potent AR antagonist that functions by competing with androgen, preventing AR coactivator binding and by enhancing binding of AR corepressors...

3-Mono-chloropropane-1,2-diol (3-MCPD) is a contaminant that occurs in food in its free (diol) form as well as in an esterified (with fatty acids) form. Using a simple intestinal model, it was demonstrated that 3-MCPD monoesters and 3-MCPD diesters are accepted by intestinal lipase as substrates in vitro. Under the chosen conditions, the yield of 3-MCPD from a 3-MCPD monoester was greater than 95% in approximately 1 min. Release from the diesters was slower, reaching about 45, 65 and 95% of 3-MCPD after 1, 5 and 90 min of incubation, respectively...

We examined the combined effect of circulating sex hormones and SRD5A2 V89L polymorphism on prostate cancer risk in a case-control study (300 cases and 300 controls) nested within the Carotene and Retinol Efficacy Trial. A moderate increase in risk associated with above-median serum levels of androstenedione and dehydroepiandrosterone sulfate (DHEAS) was present irrespective of V89L genotype. However, in L/L or V/L men, above-median DHEAS levels were associated with an increased risk of aggressive tumors [odds ratios (OR), 3...

The conversion of beta-myrcene to the furanoid flavour compound perillene by Pleurotus ostreatus was investigated using trideutero beta-myrcene, trideutero alpha-(Z)-acaridiol and non-labeled 1,2- and 3,10-epoxy-beta-myrcene, alpha,alpha-acarilactol, and perillene as substrates. Myrcene diols were formed from the cleavage of myrcene epoxides, but only alpha-(Z)-acaridiol, a 1,4-butanediol derivative most likely generated through a base-catalysed epoxide opening, was a suitable precursor of perillene. Once formed, this key intermediate was rapidly oxidised and the resulting cyclic lactol was dehydrated to yield perillene...

The capability of biotransformation of 11 microalgae strains was tested on ethinylestradiol (EE). Seven strains were ineffective whilst Selenastrum capricornutum, Scenedesmus quadricauda, Scenedesmus vacuolatus and Ankistrodesmus braunii biotransformed the substrate. EE was converted by S. capricornutum in three products (ethinylestradiol glucoside, 3-beta-D-glucopyranosyl-2-hydroxyethinylestradiol, and 3-beta-D-glucopyranosyl-6beta-hydroxyethinyl estradiol) in 40%, 5%, and 5% yields, respectively. S. quadricauda transformed EE into 17alpha-ethinyl-1,4-estradien-10,17beta-diol-3-one (12%) and A...

Ethyl acetate extracts from heartwood of seven western conifer trees and individual volatile compounds in the extracts were tested for antimicrobial activity against Phytophthora ramorum. Extracts from incense and western redcedar exhibited the strongest activity, followed by yellow-cedar, western juniper, and Port-Orford-cedar with moderate activity, and no activity for Douglas-fir and redwood extracts. Chemical composition of the extracts varied both qualitatively and quantitatively among the species with a total of 37 compounds identified by mass spectrometry...

A sensitive liquid chromatography-electrospray ionization-tandem mass spectrometric (LC-ESI-MS/MS) method for the simultaneous determination of five 3-oxo-4-ene-neuroactive steroids, i.e. androstenedione, testosterone (T), progesterone (PROG), 20alpha-dihydroprogesterone and 20beta-dihydroprogesterone, in rat brain has been developed and validated. The brain steroids were extracted with methanol-acetic acid, purified using solid-phase extraction cartridges and subjected to LC-ESI-MS/MS. The method does not require derivatization...

Methyl 4,6-O-benzylidene-2,3-di-O-propargyl-alpha-D-glucoside (2) has been prepared and its structure determined, including its X-ray structural analysis. For comparison the structure of the corresponding allyl derivative has also been determined by X-ray crystallography. Glucoside 2 is a versatile starting material for numerous novel derivatives such as diols, a diester, a diacid, and a dialdehyde. Subjecting 2 to a Mannich reaction leads to a (bis)amine in excellent yields. The click reaction between 2 and benzyl azide furnishes a (bis)triazole as the main product...

Acquired resistance to endocrine therapy represents a major clinical obstacle to the successful management of estrogen-dependent breast cancers expressing estrogen receptor alpha (ERalpha). Because a switch from ligand-dependent to ligand-independent activation of ERalpha-regulated breast cancer cell growth and survival may define a path to endocrine resistance, enhanced mechanistic insight concerning the ligand-independent fate and function of ERalpha, including a more complete inventory of its ligand-independent cofactors, could identify novel markers of endocrine resistance and possible targets for therapeutic intervention in breast cancer...