Effects of Red Sorghum-Derived Deoxyanthocyanidins and Their O-β-D-Glucosides on E-Cadherin Promoter Activity in PC-3 Prostate Cancer Cells.

Although much less common than anthocyanins, 3-Deoxyanthocyanidins (3-DAs) and their glucosides can be found in cereals such as red sorghum. It is speculated that their bioavailability is higher than that of anthocyanins. Thus far, little is known regarding the therapeutic effects of 3-DAs and their O-β-D-glucosides on cancer, including prostate cancer.

Luteolin modulates gene expression related to steroidogenesis, apoptosis, and stress response in rat LC540 tumor Leydig cells.

In males, androgens are mainly produced by Leydig cells from the testis. A critical and highly regulated step of steroidogenesis involves the importation of cholesterol within the mitochondria by the steroidogenic acute regulatory (STAR) protein. During aging, STAR protein levels in Leydig cells gradually decrease, leading to a reduced entry of cholesterol into mitochondria and lower testosterone production.

Analogs of Natural 3-Deoxyanthocyanins: O-Glucosides of the 4',7-Dihydroxyflavylium Ion and the Deep Influence of Glycosidation on Color.

3-Deoxyanthocyanidins and their -β-d-glucosides are natural pigments abundant in black sorghum. -glycosidation can perturb the acid-base properties of the chromophore and lower its electron density with a large impact on the distribution of colored and colorless forms in aqueous solution. In this work, the influence of -glycosidation on color is systematically studied from a series of 3-deoxyanthocyanin analogs.

Quantification of three galloylglucoside flavour precursors by liquid chromatography tandem mass spectrometry in brandies aged in oak wood barrels.

Vanillin-(6'-O-galloyl)-β-glucopyranoside (VGG), 3,4,5-trimethoxyphenyl-(6'-O-galloyl)-β-glucopyranoside (TMPGG), and (6R,9R)-3-oxo-α-ionol-9-O-(6'-O-galloyl)-β-glucopyranoside (macarangioside E) were identified as aroma precursors in oak wood. An LC-MS/MS method was developed and validated to quantify these three galloylglucoside compounds in brandies aged in oak barrels. The detection system consisted of a triple quadrupole mass analyser operating in multiple reaction monitoring (MRM) mode.

Chemically synthesized glycosides of hydroxylated flavylium ions as suitable models of anthocyanins: binding to iron ions and human serum albumin, antioxidant activity in model gastric conditions.

Polyhydroxylated flavylium ions, such as 3',4',7-trihydroxyflavylium chloride (P1) and its more water-soluble 7-O-β-d-glucopyranoside (P2), are readily accessible by chemical synthesis and suitable models of natural anthocyanins in terms of color and species distribution in aqueous solution. Owing to their catechol B-ring, they rapidly bind FeIII, weakly interact with FeII and promote its autoxidation to FeIII. Both pigments inhibit heme-induced lipid peroxidation in mildly acidic conditions (a model of postprandial oxidative stress in the stomach), the colorless (chalcone) forms being more potent than the colored forms.

The impact of industrial processing on health-beneficial tomato microconstituents.

The effect of industrial processing was investigated on the stability of tomato carotenoids, phenolic compounds and ascorbic acid. A deep insight in the processed products allowed the quantification of caffeic acid hexosides, which are far more important contributors than the well-known chlorogenic acid, dicaffeoylquinic acids and quercetin oligosaccharides (new feruloyl, sinapoyl and syringoyl derivatives of quercetin apiosylrhamnosylglucoside). (E)-β-Carotene and (E)-lycopene were also quantified along with different mono- and di-(Z)-isomers of lycopene which were tentatively assigned.

Synthesis of hydroxycinnamic acid glucuronides and investigation of their affinity for human serum albumin.

Hydroxycinnamic acids (HCAs) are among the most abundant dietary polyphenols. Recent bioavailability studies have shown that HCAs enter the blood circulation mainly as glucuronides, which are thus most likely to express their potential health effects. In this work, an efficient synthesis of HCA O-arylglucuronides is developed.

Chemical synthesis of hydroxycinnamic acid glucosides and evaluation of their ability to stabilize natural colors via anthocyanin copigmentation.

This work describes the chemical synthesis of O-aryl-beta-D-glucosides and 1-O-beta-D-glucosyl esters of hydroxycinnamic acids. In particular, O-aryl-beta-D-glucosides were efficiently prepared via a simple diastereoselective glycosylation procedure using phase transfer conditions. Despite the lability of its ester linkage, 1-O-beta-D-caffeoylglucose could also be obtained using a Lewis acid catalyzed glycosylation step and a set of protective groups that can be removed under neutral conditions.

Antioxidant activity of olive phenols: mechanistic investigation and characterization of oxidation products by mass spectrometry.

In this work, the antioxidant activity of olive phenols is first characterized by their stoichiometries n(tot)(number of radicals trapped per antioxidant molecule) and their rate constants for the first H-atom abstraction k(1) by the stable radical DPPH. It appears that oleuropein, hydroxytyrosol and caffeic acid have the largest k(1) values, whereas dihydrocaffeic acid, an intestinal metabolite of caffeic acid, is the best antioxidant in terms of n(tot). For phenols with a catechol moiety n(tot) is higher than two, implying an antioxidant effect of their primarily formed oxidation products.

Synthesis and surface-active properties of a new class of surfactants derived from D-gluconic acid.

Novel sugar-based surfactants were synthesized starting from D-gluconolactone. Three different functional groups were used to link the sugar moiety and the hydrophobic part. The physico-chemical properties for the use as adjuvant for pesticidal formulations of one of these compounds were evaluated and compared.