Yeast mannan increases Bacteroides thetaiotaomicron abundance and suppresses putrefactive compound production in in vitro fecal microbiota fermentation.

Yeast mannan is a part of yeast cell wall and can potentially affect gut microflora as a soluble dietary fiber. We demonstrated that yeast mannan suppressed putrefactive production and increased the relative abundance of Bacteroides thetaiotaomicron in in vitro fecal fermentation. These results suggest that yeast mannan can be used as a novel prebiotic food ingredient.

Fragmentation and Ionization Efficiency of Positional and Functional Isomers of Paeoniflorin Derivatives in Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry.

Paeoniflorin and albiflorin, which are functional isomers, are the major constituents of an herbal medicine derived from Paeonia lactiflora. Those functional isomers and their galloylated derivatives, which are positional isomers, were studied by matrix-assisted laser desorption/ionization-tandem mass spectrometry (MALDI-MS/MS). The resulting mass spectra are discussed based on the fragmentation patterns of the sodium adducts. The product ion spectra of 4-O-galloylalbiflorin and 4'-O-galloylpaeoniflorin differed, even though they were positional isomers. The fragmentations of the ester parts were influenced by the neighboring hydroxyl groups. The ionization efficiency of the sodium adduct of albiflorin was higher than that for paeoniflorin. These results indicate that the carboxylic ester group has a higher affinity for sodium ions than the acetal group, which can be attributed to the carbonyl oxygen being negatively polarized, allowing it to function as a Lewis base.

Suppressive effect of Yamato-mana (Brassica rapa L. Oleifera Group) constituent 3-butenyl glucosinolate (gluconapin) on postprandial hypertriglyceridemia in mice.

We examined the bioactivity of Yamato-mana (Brassica rapa L. Oleifera Group) constituent glucosinolates and found that 3-butenyl glucosinolate (gluconapin) decreased the plasma triglyceride gain induced by corn oil administration to mice. However, phenethyl glucosinolate (gluconasturtiin) had little effect. 2-Propenyl glucosinolate (sinigrin) also reduced the plasma triglyceride level, which suggests that alkenyl glucosinolates might be promising agents to prevent postprandial hypertriglyceridemia.

Novel secondary metabolites, spirosorbicillinols a, B, and C, from a fungus.

In our searching program for novel sorbicillin related compounds, three novel compounds, spirosorbicillinols A (1), B (2), and C (3), were isolated from the fermentation broth of the USF-4860 strain isolated from a soil sample. The planar structures of compounds 1-3 were determined from spectroscopic evidence and degradation reaction, and that of 1 was the same as that of 2. The relative stereochemistries of compounds 1-3 were determined by (1)H-(1)H coupling constants, the elucidation of HMBC and NOESY spectra in detail. 1 and 2 were stereoisomers at C8 position, each other. We propose that compounds 1 and 2 were formed by exo and endo intermolecular Diels-Alder reaction between sorbicillinol as a diene and scytolide (proposed precursor-1) as a dienophile, respectively. Similarly, we propose that compound 3 was formed by an endo intermolecular Diels-Alder reaction between sorbicillinol and proposed precursor-2.

Androgen modulators from the roots of Paeonia lactiflora (paeoniae radix) grown and processed in nara prefecture, Japan.

The monoterpene glycoside, 3'-O-galloylpaeoniflorin (1), and four known compounds, 6'-O-galloylalbiflorin (2), pentagalloylglucose (3), 6'-O-benzoylpaeoniflorin (4) and 6'-O-galloylpaeoniflorin (5), were isolated from the roots of Paeonia lactiflora that had been grown and processed in Nara prefecture, Japan, as androgen modulators. Their structures were elucidated based on spectroscopic analysis. Compounds 2 and 3 showed strong androgen receptor (AR) binding activity (IC(50) values 33.7 and 4.1 microg/ml, respectively), 1, 4 and 5 showed weak activity (20, 31 and 12% at 120 microg/ml, respectively). However, paeoniflorin (6) and albiflorin (7), the structures of which are related to 1, 2, 4 and 5, showed no activity. These results suggested that both the structure of albiflorin and the galloyl moiety are important for 2 to show strong AR binding activity. Furthermore, compounds 1-5 inhibited growth of an androgen-dependent LNCaP-FGC (prostate cancer cell line), and were indicated to be AR antagonists. Compounds 2 and 3 might be candidates as safe, natural anti-androgens.

Two new galloylated monoterpene glycosides, 4-O-galloylalbiflorin and 4'-O-galloylpaeoniflorin, from the roots of Paeonia lactiflora (Paeoniae radix) grown and processed in Nara Prefecture, Japan.

Two new galloylated monoterpene glycosides, 4-O-galloylalbiflorin and 4'-O-galloylpaeoniflorin, were isolated from the roots of Paeonia lactiflora that had been grown and processed in Nara prefecture, Japan. Their structures were elucidated based on spectroscopic analysis. These compounds showed androgen receptor (AR) binding activity.

Suppressive Effects of Selected Food Phytochemicals on CD74 Expression in NCI-N87 Gastric Carcinoma Cells.

Helicobacter pylori (H. pylori) is one of the most widespread human pathogens, and plays major roles in chronic gastritis and gastric cancer. CD74 of gastric epithelial cells has recently been identified as an adhesion molecule to urease in H. pylori. In this study, we found that CD74 is highly expressed in a constitutive manner in NCI-N87 human gastric carcinoma cells at both the protein and mRNA levels as compared with Hs738St./Int fetal gastric cells. Subsequently, a novel cell-based ELISA able to rapidly screen the suppressive agents of CD74 expression was established. NCI-N87 cells were treated separately with 25 different food phytochemicals (4-100 microM) for 48 h and subjected to our novel assay. From those results, a citrus coumarin, bergamottin, was indicated to be the most promising compound with an LC(50)/IC(50) value greater than 7.1, followed by luteolin (>5.4), nobiletin (>5.3), and quercetin (>5.1). Our findings suggest that these CD74 suppressants are unique candidates for preventing H. pylori adhesion and subsequent infection with reasonable action mechanisms.

[Structure identification of contaminants in a beverage product by liquid chromatography coupled with quadrupole time-of-flight mass spectrometry].

The contaminants in a beverage product that had been reported to have a strange taste were identified. By comparative analysis with the normal product using liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (LC-QTOF-MS), six unknown compounds were detected in the total ion current chromatograms of the product in question. Detailed analysis of the mass spectra and product ion spectra of these compounds strongly suggested that the compounds were capric acid diethanolamide, lauric acid diethanolamide, myristic acid diethanolamide, lauryl dimethylaminoacetic acid, lauryl sulfate, and lauric acid, all of which are surfactants commonly used as ingredients of household detergents and shampoos. We searched commercially available detergent products to check for the presence of these six surfactants, and identified products that might have been intentionally or unintentionally mixed into the beverage product after opening.

Phenethyl isothiocyanate suppresses nitric oxide production via inhibition of phosphoinositide 3-kinase/Akt-induced IFN-gamma secretion in LPS-activated peritoneal macrophages.

Phenethyl isothiocyanate (PEITC), a constituent of many cruciferous vegetables, is well known to have versatile physiological activities, including chemopreventive effects. On the other hand, its anti-inflammatory effects are poorly reported. Nitric oxide (NO) is associated with a wide variety of inflammatory diseases. In this study, we investigated the effects of PEITC on NO production in LPS-activated peritoneal macrophages from ICR mice. The signaling pathway of LPS-induced NO production was examined using neutralizing antibodies [anti-interferon (IFN)-gamma and anti-interleukin (IL-12)] and specific protein kinase inhibitors, as well as others. The activity of PEITC toward NOx production was assessed in mice that received LPS via intraperitoneal administration. The neutralizing antibody of anti-IFN-gamma, but not anti-IL-12, suppressed LPS-induced NO production by 90%. LY294002, a specific inhibitor of phosphoinositide-3-kinase, suppressed Akt and IFN-gamma mRNA expression up-regulated by LPS, whereas PEITC exhibited a similar inhibition profile. Furthermore, oral administration of PEITC significantly suppressed the serum concentration of NOx in ICR mice. Our results suggest that PEITC suppresses LPS-induced NO production via inhibition of Akt activation and the resultant decrease in expression of IFN-gamma. This is one of the first reports to demonstrate a marked anti-inflammatory effect of PEITC following its oral administration.

Novel DPPH radical scavengers, demethylbisorbibutenolide and trichopyrone, from a fungus.

In our screening program for antioxidants with 1,1-diphenyl-2-picrylhydrazyl (DPPH)-radical scavenging activity, two novel compounds, demethylbisorbibutenolide (1) and trichopyrone (2), were isolated from the fermentation broth of the fungus of USF-4860 strain isolated from a soil sample. The structures of these compounds were determined from spectroscopic evidence. The biosynthetic origin of the carbon atoms of 2 was unambiguously determined by feeding experiments using (13)C-labeled precursors and elucidation of the (13)C-NMR spectrum of (13)C-labeled 2. These studies showed that 2 was derived from five acetates and a methyl group of methionine. In the DPPH-radical scavenging assay, 1 and 2 gave ED(50) values of 149 and 167 muM after standing for 2.0 hr. Compound 2 reacted with the DPPH radical to form reaction product 3 which was determined to be 1-[4-(3,4-dihydro-3-methyl-6-{1,3-pentadienyl}-2,4-dioxo-2H-pyran-3-yl)-phenyl]-1-phenyl-2-picrylhydrazine from spectroscopic evidence.

Symbioimine and neosymbioimine, amphoteric iminium metabolites from the symbiotic marine dinoflagellate Symbiodinium sp.

Two amphoteric iminium metabolites, symbioimine (1) and neosymbioimine (2), were isolated from a cultivated symbiotic marine dinoflagellate Symbiodinium sp. Compounds 1 and 2 have a characteristic 6,6,6-tricyclic iminium ring structure and an aryl sulfate moiety. The plausible biogenetic pathway of 1 and 2 can be explained by an intramolecular Diels-Alder reaction followed by imine cyclization. Symbioimine (1) inhibited the differentiation of RAW264 cells into osteoclasts (EC50 = 44 microM), and significantly inhibited cyclooxygenase-2 activity at 10 microM. Thus, symbioimine is a potent anti-resorptive and anti-inflammatory drug.