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Ginger is a widely consumed spice and possesses numerous pharmacological properties. However, studies addressing the efficacy of ginger in humans have been inconsistent. Many confounding factors need to be considered when evaluating the health effects from ginger against chronic diseases, especially the levels of bioactive components in the ginger formulations used in human trials. Gingerols, the major compounds in fresh ginger, are liable to dehydrate and convert to shogaols, the major compounds in dried ginger, as a result of the instability of β-hydroxyl ketone when exposed to heat and/or acidic conditions. As a result of various heating and processing methods, the concentrations of gingerols and shogaols in ginger products vary significantly. Increasing evidence has shown that gingerols and shogaols have different bioactivities, molecular targets, and metabolic pathways, suggesting the importance of identifying the optimal oral ginger composition for a specific disease. In this perspective, we highlighted differences in the composition between fresh ginger and dry ginger, bioactivities, molecular targets, and metabolic pathways of gingerols and shogaols as well as future perspectives regarding precision research on ginger.

Rapid and accurate measurement of polyphenol oxidase (PPO) activity is important in the food industry as PPOs play a vital role in catalyzing enzymatic reactions. The aim of this study was to develop surface-enhanced Raman scattering (SERS) approach for accurate determination of PPO activity in fruit and vegetables using the reduction in SERS intensity of catechol in reaction medium. Within a certain catechol concentration, when a purified PPO solution was analyzed, the reduction in SERS intensity (Δ I) was linear to PPO activity ( E c ) in a wide range of 500-50 000 U/L, and a linear regression equation of log Δ I/Δ t = 0.6223 log E c + 0.8072, with a correlation coefficient of 0.9689 and a limit of detection of 224.65 U/L, was obtained. The method was used for detecting PPO activity in apple and potato samples, and the results were compared with those obtained from colorimetric assay, which demonstrated that the proposed method could be successfully used for detecting PPO activity in food samples.

Ginger, a popular functional food, has been widely used throughout the world for centuries. However, its metabolic behaviors remain unclear, which entails an obstacle to further understanding of its functional components. In this study, the metabolic profiles of ginger in rats were systemically investigated by UPLC-Q/TOF-MS. The results included the characterization of 92 components of ginger based on the summarized fragmentation patterns and self-building chemical database. Furthermore, four representative compounds were selected to explore the typical metabolic pathways of ginger. Consequently, 141 ginger-related xenobiotics were characterized, following the metabolic spots of the pungent phytochemicals were summarized. These findings indicated that the in vivo effective components of ginger were mainly derived from [6]-gingerol and [6]-shogaol. Meanwhile, hydrogenation, demethylation, glucuronidation, sulfation, and thiolation were their major metabolic reactions. These results expand our knowledge about the metabolism of ginger, which will be important for discovering its functional components and the further mechanism research.

The ethanolic extract of grains of paradise (Aframomum melegueta Schum, Zingiberaceae) has been evaluated for inhibitory activity on cyclooxygenase-2 (COX-2) enzyme, in vivo for the anti-inflammatory activity and expression of several pro-inflammatory genes. Bioactivity-guided fractionation showed that the most active COX-2 inhibitory compound in the extract was [6]-paradol. [6]-Shogaol, another compound from the extract, was the most active inhibitory compound in pro-inflammatory gene expression assays. In a rat paw edema model, the whole extract reduced inflammation by 49% at 1000 mg/kg. Major gingerols from the extract [6]-paradol, [6]-gingerol, and [6]-shogaol reduced inflammation by 20, 25 and 38%. respectively when administered individually at a dose of 150 mg/kg. [6]-Shogaol efficacy was at the level of aspirin, used as a positive control. Grains of paradise extract has demonstrated an anti-inflammatory activity, which is in part due to the inhibition of COX-2 enzyme activity and expression of pro-inflammatory genes.

Caffeic acid was subjected to degradation under subcritical water conditions within 160-240 °C and at a constant pressure of 5 MPa in a continuous tubular reactor. Caffeic acid degraded quickly at these temperatures; the main products identified by liquid chromatography-diode array detection/mass spectrometry were hydroxytyrosol, protocatechuic aldehyde, and 4-vinylcatechol. The reaction rates for the degradation of caffeic acid and the formation of products were evaluated. Online high-performance liquid chromatography/2,2-diphenyl-1-picryhydrazyl assay was used to determine the antioxidant activity of each product in the solution. It was found that the overall antioxidant activity of the treated solution did not change during the degradation process. This study showed a potential of formation of antioxidants from natural phenolic compounds under these subcritical water conditions, and this may lead to a discovering of novel antioxidants compounds during the extraction by this technique.

Severe flooding of the Brahmaputra River during the monsoon season and continuous rainfall in the northeast region (NER) of India cause an enormous loss of ginger crop every year. In this context, the present study investigates the variation in the essential oil composition and oleoresin and [6]-gingerol contents in 10 different fresh ginger cultivars harvested at 6- and 9-month maturity from five different states of NER. Monoterpenes, sesquiterpenes, and citral composition in the essential oil were evaluated to ascertain their dependence upon the maturity of ginger. Except Mizoram Thinglaidum, Mizoram Thingria, Nagaland Nadia, and Tripura I ginger cultivars, all other cultivars showed an increase in the citral content during the maturity that was observed for the first time. At 6-month maturity, a higher undecanone level was found in Nagaland Nadia (7.36 ± 0.61%), Tripura I (6.23 ± 0.61%), and Tripura III (9.17 ± 0.76%) cultivars, and these data can be used as a benchmark to identify those immature varieties. Interestingly, the Nagaland Nadia cultivar showed higher ar-curcumene (9.57 ± 0.58%) content than zingiberene (5.84 ± 0.24%), which was unique among all cultivars. Ginger harvested at 9-month maturity from the Tripura II cultivar had the highest citral content (22.03 ± 0.49%), and the Meghalaya Mahima cultivar had the highest zingiberene content (29.89 ± 2.92%). The oleoresin content was found to decrease with maturity in all cultivars, except Assam Fibreless and Manipur I. Moreover, the highest oleoresin (11.43 ± 0.58 and 9.42 ± 0.63%) and [6]-gingerol (1.67 ± 0.03 and 1.67 ± 0.05 g) contents were observed for Tripura II and Nagaland Nadia, respectively. This study suggests that Tripura and Nagaland are the most ideal locations in NER for ginger cultivation to obtain high yields of oleoresin and [6]-gingerol contents and harvesting at the 6-month maturation will compensate for the loss of ginger crop caused by the Brahmaputra River flooding in NER every year.

Liquid chromatography-time-of-flight mass spectrometry (LC-TOF/MS) was established for the simultaneous separation, identification, and quantification of gingerol-related compounds in ginger products. The established method has been shown to provide a satisfactory linearity (r > 0.999) in a wide range (5-5000 ng/mL), low limits of detection and quantification, high precision, and inter- and intraday repeatability. The detection sensitivity of gingerols and shogaols by TOF/MS was 70-100 times higher than conventional UV detection at 288 nm. In this study, 19 ginerol-related compounds in the samples were identified and quantified by the established LC-TOF/MS method. The dried ginger powder products contained the highest quantity of gingerol-related compounds (7126.3-13789.0 μg/g), followed by fresh ginger products (2007.9-2790.0 μg/g), powdered ginger tea products (77.29-81.75 μg/g), and hot water ginger extracts (54.59-123.23 μg/mL). Shogaols were not found in fresh gingers. This paper represents the first report on the LC-TOF/MS analysis for the simultaneous characterization and quantification of gingerol-related compounds in ginger products.

We employed a kinetic method to determine the distributions of the antioxidants hydroxytyrosol (HT) and hydroxytyrosol acetate (HTA) between the oil, aqueous, and interfacial regions of a model food emulsion composed of stripped olive oil, acidic water, and a blend of Tween 80 and Span 80 [hydrophilic–lipophilic balance (HLB) = 8.05] as an emulsifier. HT is oil-insoluble, but HTA is both oil- and water-soluble (partition constant P(O)(W) = 0.61). Results indicate that, at a given emulsifier volume fraction Φ(I), the fraction of HTA in the interfacial region is higher than that of HT. The percentage of both antioxidants increases with an increasing Φ(I), so that % HT > 40% at Φ(I) = 0.005 and % HT > 80% at Φ(I) = 0.04. HTA appears to be a better antioxidant than HT, as shown by an accelerated oxidative test (Schaal oven method). A correlation between their distribution in the emulsion and their efficiency was established.

For the first time, a sensitive reversed-phase HPLC electrochemical array method has been developed for the quantitative analysis of 8 major ginger components ([6]-, [8]-, and [10]-gingerol, [6]-, [8]-, and [10]-shogaol, [6]-paradol, and [1]-dehydrogingerdione) in 11 ginger-containing commercial products. This method was valid with unrivaled sensitivity as low as 7.3-20.2 pg of limit of detection and a range of 14.5-40.4 pg for the limit of quantification. The levels of 8 ginger components in 11 different commercial products were quantified by use of this method. The results found that both levels and ratios among the 8 compounds vary greatly in commercial products.

Sesaminol triglucoside (STG) is the main sesame (Sesamum indicum L.) lignan. Like many other plant lignans, STG can be converted to the mammalian lignans by intestinal microbiota. The objectives of the present study were to investigate the distribution of STG metabolite in rats, and the effects of STG and its metabolite on in vitro inflammation and estrogenic activities. STG was metabolized via intestinal microflora to a biologically active catechol moiety which would then be absorbed into the body in rats. After oral administration of STG to Sprague-Dawley rats, the concentrations of major STG metabolites in rectum, cecum, colon, and small intestines are higher than those in liver, lung, kidney, and heart. Its concentration in brain is low but detectable. The present study demonstrates that STG may be metabolized to form the catechol metabolites first by intestinal microflora and then incorporated via intestine absorption into the cardiovascular system and transported to other tissues. Results showed that the catechol metabolites were found to be able to penetrate the tail end of intestines (large intestine) and go through urinary excretion. STG metabolites significantly reduced the production of IL-6 and TNF-alpha in RAW264.7 murine macrophages stimulated with lipopolysaccharide. The estrogenic activities of STG metabolites were also established by ligand-dependent transcriptional activation through estrogen receptors. This study clearly shows that STG has anti-inflammatory and estrogenic activities via metabolism of intestinal microflora.

Changes in the yields of the oleoresin and content of pungent bioactive principles: [6], [8], [10] gingerols and [6] shogaol of Jamaican ginger ( Zingiber officinale) were investigated during different stages of maturity (7-9 months). Ethanolic oleoresin extracts were prepared (95%, w/w) by cold maceration of dried ginger powder, and their percentage yields were calculated (w/w). The pungent bioactive principles in the ginger oleoresin were extracted with methanol and quantitatively analyzed by high performance liquid chromatography (HPLC). Ginger harvested at 8 months from Bourbon, Portland had the highest oleoresin yield (8.46 +/- 0.46%). [6] Gingerol was found to be the most abundant pungent bioactive principle in all the oleoresin samples investigated, with the 9 months sample from Bourbon, Portland containing the highest level (28.94 +/- 0.39%). The content of [6] gingerols was also found to be consistently high (7-9 months) in oleoresin samples from Johnson Mountain, St. Thomas (15.12 +/- 0.39 to 16.02 +/- 0.95%). The results suggest that Bourbon in Portland may be the most ideal location for cultivating ginger for high yields and quality, however, Johnson Mountain in St. Thomas could prove to be the least restrictive location, allowing for harvesting of good quality material throughout the maturity period (7-9 months).

In this paper is considered a new computerized approach to the determination of concentrations of phenolic compounds (caffeic acid and catechol). An integrated artificial neural network (ANN)/laccase biosensor is designed. The data collected (current signals) from amperometric detection of the laccase biosensor were transferred into an ANN trained computer for modeling and prediction of output. Such an integrated ANN/laccase biosensor system is capable of the prediction of caffeic acid and catechol concentrations of olive oil mill wastewater, based on the created models and patterns, without any previous knowledge of this phenomenon. The predicted results using the ANN were compared with the amperometric detection of phenolic compounds obtained at a laccase biosensor in olive oil wastewater of the 2004-2005 harvest season. The difference between the real and the predicted values was <0.5%. biosensor; olive oil mill wastewater; chemical analysis; phenolic compounds.

Aimed at elucidating intense bitter-tasting molecules in coffee, various bean ingredients were thermally treated in model experiments and evaluated for their potential to produce bitter compounds. As caffeic acid was found to generate intense bitterness reminiscent of the bitter taste of a strongly roasted espresso-type coffee, the reaction products formed were screened for bitter compounds by means of taste dilution analysis, and the most bitter tastants were isolated and purified. LC-MS/MS as well as 1-D/2-D NMR experiments enabled the identification of 10 bitter compounds with rather low recognition threshold concentrations ranging between 23 and 178 micromol/L. These bitter compounds are the previously unreported 1,3-bis(3',4'-dihydroxyphenyl) butane, trans-1,3-bis(3',4'-dihydroxyphenyl)-1-butene, and eight multiply hydroxylated phenylindanes, among which five derivatives are reported for the first time. In addition, the occurrence of each of these bitter compounds in a coffee brew was verified by means of LC-MS/MS (ESI-) operating in the multiple reaction monitoring (MRM) mode. The structures of these bitter compounds show strong evidence that they are generated by oligomerization of 4-vinylcatechol released from caffeic acid moieties upon roasting.

The objective of this study was to investigate the potential of various raw bean components as precursors of pyrogallol (1), hydroxyhydroquinone (2), catechol (3), 4-ethylcatechol (4), 4-methylcatechol (5), and 3-methylcatechol (6) under quasi "natural" roasting conditions by using the recently developed "in bean" model roast experiments. Freeze-dried, fully extracted bean shells were loaded with aqueous solutions of either single coffee compounds or fractions isolated from the raw bean solubles. After freeze-drying, these reconstituted beans were roasted, aqueous coffee brews were prepared, and the target phenols were quantified by means of a stable isotope dilution assay with LC-MS/MS detection. On the basis of the quantitative data, it can be concluded that upon coffee bean roasting, catechol (3) is primarily formed by degradation of caffeoylquinic acids from both the caffeic acid and the quinic acid moiety of the molecule, as well as from Maillard-type reactions from carbohydrates and amino acids. In contrast, pyrogallol (1) and hydroxyhydroquinone (2) are efficiently generated from carbohydrates and amino acids and, in addition, from free or chlorogenic acid bound quinic acid moieties. 4-Ethylcatechol (4) is exclusively generated upon thermal breakdown of caffeic acid moieties. 3-Methylcatechol (6) is formed primarily from the Maillard reactions and, to a minor extent, also from various phenolic precursors, whereas 4-methylcatechol (5) is produced in trace amounts only from all of the different precursors investigated. On the basis of this precursor study, reaction routes explaining the formation of the target phenols are proposed.

An extraction procedure and an analytical method have been developed to detect and quantify for the first time a series of ellagitannin derivatives formed in wine during aging in oak barrels. The method involves a preliminary purification step on XAD7 HP resin followed by a second purification step on TSK 40 HW gel. The resulting extract is analyzed for compound identification and quantitative determination by high-performance liquid chromatography-electrospray ionization-mass spectrometry in single ion recording mode. Reference compounds, which are accessible through hemisynthesis from the oak C-glycosidic ellagitannin vescalagin, were used to build calibration curves, and chlorogenic acid was selected as an internal standard. This method enabled us to estimate the content of four flavano-ellagitannins and that of another newly identified wine polyphenol, beta-1-O-ethylvescalagin, in a Bordeaux red wine aged for 18 months in oak barrels. All five ellagitannin derivatives are derived from the nucleophilic substitution reaction of vescalagin with the grape flavan-3-ols catechin and epicatechin or ethanol.

A straightforward stable isotope dilution analysis (SIDA) for the quantitative determination of the di- and trihydroxybenzenes catechol (1), pyrogallol (2), 3-methylcatechol (3), 4-methylcatechol (4), and 4-ethylcatechol (5) in foods by means of liquid chromatography-tandem mass spectrometry was developed. With or without sample preparation involving phenylboronyl solid phase extraction, the method allowed the quantification of the target compounds in complex matrices such as coffee beverages with quantification limits of 9 nmol/L for 4-ethylcatechol, 24 nmol/L for catechol, 3-methyl-, and 4-methylcatechol, and 31 nmol/L for pyrogallol. Recovery rates for the analytes ranged from 97 to 103%. Application of the developed SIDA to various commercial food samples showed that quantitative analysis of the target compounds is possible within 30 min and gave first quantitative data on the amounts of di- and trihydroxybenzenes in coffee beverage, coffee powder, coffee surrogate, beer, malt, roasted cocoa powder, bread crust, potato crisps, fruits, and cigarette smoke and human urine. Model precursor studies revealed the carbohydrate/amino acid systems as well as the plant polyphenols catechin and epicatechin as precursors of catechol and 5-O-caffeoylquinic acid, caffeic acid as a precursor of catechol and 4-ethylcatechol, and gallocatechin, epigallocatechin, and gallic acid as precursors of pyrogallol.

This paper describes atmospheric pressure ionization (API) LC-MS-MS determination of urushiols, 3-n-alkenyl- and -alkyl-substituted catechols responsible for poison oak dermatitis. Urushiol was isolated from Western poison oak according to the method of Elsohly et al. (1) (J. Nat. Prod. 1982, 45, 532-538)-the purified preparation contained C(17)- and C(15)-substituted urushiols with zero, one, two, and three double bonds as determined from GC-MS analysis of trimethylsilyl derivatives. Urushiol mixtures were separated on a C(18) reversed phase HPLC column with a methanol-water gradient with urushiols eluting in 100% methanol. Atmospheric pressure chemical ionization (APCI) produced primarily [M - H](-) and MH(+) molecule ions. Electrospray ionization (ESI) yielded [M - H](-) and adduct ions including [M + Cl](-). Daughter ions of [M - H](-) included quinoid radical anions ([M - H - H(2)](-) and m/z 122(-)) and a benzofuran phenate (m/z 135(-)). A suite of hydrocarbon fragments were produced by collision-induced dissociation of MH(+) directly or via an intermediate [MH - H(2)O](+) daughter ion. Six urushiol congeners, one not previously reported in poison oak, were determined by negative ion API-LC-MS-MS with detection limits of approximately 8 pg/microL (ESI) and approximately 800 pg/microL (APCI). API-LC-MS-MS was used to determine urushiol in surface wipes, air samples, and plant materials.