Advanced glycation endproducts in food and their effects on health.

Cyanogenic glycosides (CNglcs) are bioactive plant products derived from amino acids. Structurally, these specialized plant compounds are characterized as α-hydroxynitriles (cyanohydrins) that are stabilized by glucosylation. In recent years, improved tools within analytical chemistry have greatly increased the number of known CNglcs by enabling the discovery of less abundant CNglcs formed by additional hydroxylation, glycosylation, and acylation reactions. Cyanogenesis—the release of toxic hydrogen cyanide from endogenous CNglcs—is an effective defense against generalist herbivores but less effective against fungal pathogens. In the course of evolution, CNglcs have acquired additional roles to improve plant plasticity, i.e., establishment, robustness, and viability in response to environmental challenges. CNglc concentration is usually higher in young plants, when nitrogen is in ready supply, or when growth is constrained by nonoptimal growth conditions. Efforts are under way to engineer CNglcs into some...

Cyanogenic Glycosides: Synthesis, Physiology, and Phenotypic Plasticity

Analysis of advanced glycation endproducts in selected food items by ultra-performance liquid chromatography tandem mass spectrometry: Presentation of a dietary AGE database.

Amygdalin content of seeds, kernels and food products commercially-available in the UK.

Effect of hot air drying on volatile compounds of Flammulina velutipes detected by HS-SPME-GC-MS and electronic nose.

https://escholarship.org/content/qt92t5z02p/qt92t5z02p.pdf?t=popqcz

HS-SPME GC/MS characterization of volatiles in raw and dry-roasted almonds (Prunus dulcis)

A sensitive and reliable LC-(ESI)MS/MS method was developed and validated for the simultaneous analysis of five common advanced glycation endproducts (AGEs) after enzymatic digestion in raw and roasted almonds. AGEs included carboxymethyl-lysine (CML), carboxyethyl-lysine (CEL), pyralline (Pyr), argpyrimidine (Arg-p), and pentosidine (Pento-s). This method allows accurate quantitation of free and AGE-protein adducts of target AGEs. Results indicate that CML and CEL are found in both raw and roasted almonds. Pyr was identified for the first time in roasted almonds and accounted for 64.4% of free plus bound measured AGEs. Arg-p and Pento-s were below the limit of detection in all almond samples tested. Free AGEs accounted for 1.3-26.8% of free plus bound measured AGEs, indicating that protein-bound forms predominate. The roasting process significantly increased CML, CEL, and Pyr formation, but no significant correlation was observed between these AGEs and roasting temperature.

Determination of advanced glycation endproducts by LC-MS/MS in raw and roasted almonds (Prunus dulcis).

Amygdalin is a cynaogenic diglucoside responsible for the bitterness of almonds. Almonds display three flavor phenotypes, nonbitter, semibitter, and bitter. Herein, the amygdalin content of 20 varieties of nonbitter, semibitter, and bitter almonds from four primary growing regions of California was determined using solid-phase extraction and ultrahigh-pressure liquid chromatography electrospray triple-quadrupole mass spectrometry (UHPLC-(ESI)QqQ MS/MS). The detection limit for this method is ≤ 0.1 ng/mL (3 times the signal-to-noise ratio) and the LOQ is 0.33 ng/mL (10 times the signal-to-noise ratio), allowing for the reliable quantitation of trace levels of amygdalin in nonbitter almonds (0.13 mg/kg almond). Results indicate that amygdalin concentrations for the three flavor phenotypes were significantly different (p < 0.001). The mean concentrations of amygdalin in nonbitter, semibitter, and bitter almonds are 63.13 ± 57.54, 992.24 ± 513.04, and 40060.34 ± 7855.26 mg/kg, respectively. Levels of amygdalin ranged from 2.16 to 157.44 mg/kg in nonbitter, from 523.50 to 1772.75 mg/kg in semibitter, and from 33006.60 to 53998.30 mg/kg in bitter almonds. These results suggest that phenotype classification may be achieved on the basis of amygdalin levels. Growing region had a statistically significant effect on the amygdalin concentration in commercial varieties (p < 0.05).

/pdf/quantification-of-amygdalin-in-nonbitter-semibitter-and-2v5pof4hoq.pdf

Quantification of amygdalin in nonbitter, semibitter, and bitter almonds (Prunus dulcis) by UHPLC-(ESI)QqQ MS/MS.

Hexanal, peroxide value, and lipid hydroperoxides are common indicators of lipid oxidation in food products. However, these markers are not always reliable as levels are dynamic and often can be detected only after significant oxidation has occurred. Changes in the volatile composition of light- and dark-roast almonds were evaluated during storage over 24 weeks at 25 or 35 °C using headspace solid phase microextraction (HS-SPME) gas chromatography-mass spectrometry (GC-MS). Several volatile changes were identified in association with early oxidation events in roasted almonds. Hexenal decreased significantly during the first 6 weeks of storage and did not increase above initial levels until 20-24 weeks of storage depending upon the degree of roast. In contrast, levels of 1-heptanol and 1-octanol increased at 16-20 weeks, depending upon the degree of roast, and no initial losses were observed. Seventeen new compounds, absent in raw and freshly roasted almonds but detectable after 6 weeks of storage, were identified. Of these, 2-octanone, 2-nonanone, 3-octen-2-one, 2-decanone, (E)-2-decenal, 2,4-nonadienal, pentyl oxirane, and especially acetic acid increased significantly (that is, >10 ng/g). The degree of roasting did not correlate with the levels of these compounds. Significant decreases in roasting-related aroma volatiles such as 2-methylbutanal, 3-methylbutanal, furfural, 2-phenylacetaldehyde, 2,3-butanedione, 2-methylpyrazine, and 1-methylthio-2-propanol were observed by 4 weeks of storage independent of the degree of roast or storage conditions.

/pdf/influence-of-storage-on-volatile-profiles-in-roasted-almonds-zcqt1udg15.pdf

Influence of storage on volatile profiles in roasted almonds (Prunus dulcis).

Acrylamide is a probable human carcinogen that is found in many roasted and baked foods. This paper describes two sensitive and reliable LC-(ESI)MS/MS methods for the analysis of (1) acrylamide and (2) common acrylamide precursors (i.e., glucose, fructose, asparagine, and glutamine) in raw and roasted almonds. These methods were used to evaluate the impact of roasting temperatures (between 129 and 182 °C) and times on acrylamide formation. Controlling the roasting temperature at or below 146 °C resulted in acrylamide levels below 200 ppb at all roasting times evaluated. Six varieties of almonds collected in various regions of California over two harvest years and roasted at 138 °C for 22 min had acrylamide levels ranging from 117 ± 5 μg/kg (Sonora) to 221 ± 95 μg/kg (Butte) with an average of 187 ± 71 μg/kg. A weak correlation between asparagine content in raw almonds and acrylamide formation was observed (R(2) = 0.6787). No statistical relationship was found between acrylamide formation and almond variety, orchard region, or harvest year. Stability studies on roasted almonds indicated that acrylamide levels decreased by 12.9-68.5% (average of 50.2%) after 3 days of storage at 60 °C. Short-term elevated temperature storage may be another approach for mitigating acrylamide levels in roasted almonds.

Gong Zhang

Papers

HS-SPME GC/MS characterization of volatiles in raw and dry-roasted almonds (Prunus dulcis)

Determination of advanced glycation endproducts by LC-MS/MS in raw and roasted almonds (Prunus dulcis).

Quantification of amygdalin in nonbitter, semibitter, and bitter almonds (Prunus dulcis) by UHPLC-(ESI)QqQ MS/MS.

Influence of storage on volatile profiles in roasted almonds (Prunus dulcis).

Acrylamide formation in almonds (Prunus dulcis): influences of roasting time and temperature, precursors, varietal selection, and storage.