Phenylacetaldehyde

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Miklós Tóth - One of the best experts on this subject based on the ideXlab platform.

  • Phenylacetaldehyde: A chemical attractant for common green lacewings (Chrysoperla carnea s.l., Neuroptera: Chrysopidae)
    European Journal of Endocrinology, 2020
    Co-Authors: Miklós Tóth, Ferenc Szentkiralyi, András Bozsik, Agostino Letardi, Maria Rosaria Tabilio, Marcello Verdinelli, Pietro Zandigiacomo, Judit Jekisa, István Szarukán
    Abstract:

    Keywords. Neuroptera, Chrysopidae, Chrysoperla, green lacewings, attractant, Phenylacetaldehyde Abstract. At five sites in Hungary and Italy, traps baited with Phenylacetaldehyde caught significantly higher numbers (10 to 100 times more) of green lacewings than unbaited traps, which demonstrates that this compound is an attractant. Traps with three bait dispensers usually caught more than those with one dispenser, but the difference was significant only at two out of five test sites. There was no difference in the numbers caught by sticky delta and funnel traps baited with Phenylacetaldehyde. However, funnel traps could be adapted to catch living green lacewings. The vast majority of the specimens belonged to the Chrysoperla carnea spe- cies complex. Ch. carnea sensu lato dominated the catches at all sites. At some sites 3-11% of the insects caught were Ch. lucasina Lacroix. Phenylacetaldehyde-baited traps were attractive to both sexes, but generally more females were caught than males. Funnel traps baited with three dispensers of Phenylacetaldehyde caught green lacewing adults throughout the season in Hungary.

  • Development of a Female-Targeted Lure for the Box Tree Moth Cydalima perspectalis (Lepidoptera: Crambidae): a Preliminary Report
    Journal of Chemical Ecology, 2019
    Co-Authors: Béla Péter Molnár, István Szarukán, Antal Nagy, Sandor Koczor, Zsolt Kárpáti, Judit Csabai, Miklós Tóth
    Abstract:

    The box tree moth, Cydalima perspectalis, is an invasive pest in Europe causing damage on Buxus species. In this study, we aimed to develop a “bisexual” lure to attract both female and male moths. Based on a previous screening bioassay we tested methyl salicylate, Phenylacetaldehyde and eugenol as potential attractants in different combinations. The trapping results showed that both binary and ternary blends attracted male and female moths. Catches with these blends were comparable to catches with the synthetic pheromone. Subsequently we carried out single sensillum recordings, which proved the peripheral detection of the above-mentioned compounds on male and female antennae. To identify synergistic flower volatiles, which can be also attractive and can increase the trap capture, we collected flower headspace volatiles from 12 different flowering plant species. Several components of the floral scents evoked good responses from antennae of both females and males in gas chromatography-electroantennographic detection. The most active components were tentatively identified by gas chromatography coupled mass spectrometry as benzaldehyde, cis -ß-ocimene, (±)-linalool and phenethyl alcohol. These selected compounds in combination did not increase significantly the trap capture compared to the methyl salicylate- phenyacetaldehyde blend. Based on these results we discovered the first attractive blend, which was able to attract both adult male and female C. perspectalis in field conditions. These results will yield a good basis for the optimization and development of a practically usable bisexual lure against this invasive pest.

  • improving bisexual lures for the silver y moth autographa gamma l and related plusiinae lepidoptera noctuidae
    Acta Phytopathologica Et Entomologica Hungarica, 2019
    Co-Authors: Miklós Tóth, István Szarukán, Antal Nagy, Peter J Landolt, Julia Katalin Josvai
    Abstract:

    The addition of synthetic eugenol and benzyl acetate to the known floral chemical and moth attractant Phenylacetaldehyde synergized attraction of the silver Y moth Autographa gamma, an important no...

  • an improved female targeted semiochemical lure for the european corn borer ostrinia nubilalis hbn
    Acta Phytopathologica Et Entomologica Hungarica, 2016
    Co-Authors: Miklós Tóth, István Szarukán, Antal Nagy, T Abri, V Katona, Sz Kőrosi, T Nagy, A Szarvas, Sandor Koczor
    Abstract:

    The addition of synthetic 4-methoxy-2-phenethyl alcohol to the known attractant Phenylacetaldehyde synergized attraction of the European corn borer Ostrinia nubilalis, the blend invariably catching 3 to 5 times more than Phenylacetaldehyde on its own. Highest catches were recorded by the 1:1 blend. Both females and males were attracted, supposedly in the natural sex ratio of the local population. This improved bisex O. nubilalis attractant could be more efficient and more suitable for detection and monitoring purposes than previously know lures, making possible to draw more reliable plant protection decisions.

  • interaction of acetic acid and Phenylacetaldehyde as attractants for trapping pest species of moths lepidoptera noctuidae
    Pest Management Science, 2013
    Co-Authors: Peter J Landolt, Miklós Tóth, Robert L Meagher, István Szarukán
    Abstract:

    BACKGROUND: Phenylacetaldehyde is a flower volatile and attractant for many nectar-seeking moths. Acetic acid is a microbial fermentation product that is present in insect sweet baits. It is weakly attractive to some moths and other insects, but can be additive or synergistic with other compounds to make more powerful insect lures. RESULTS: Acetic acid and Phenylacetaldehyde presented together in traps made a stronger lure than either chemical alone for moths of the alfalfa looper Autographa californica (Speyer) and the armyworm Spodoptera albula (Walker). However, this combination of chemicals reduced captures of the cabbage looper mothTrichoplusiani (H ¨ ubner), the silver Y mothAutographa gamma (L.), MacDunnoughia confusa (Stephens) and the soybean looper moth Chrysodeixis includens (Walker) by comparison with Phenylacetaldehyde alone. CONCLUSION: These results indicate both positive and negative interactions of acetic acid, a sugar fermentation odor cue, and Phenylacetaldehyde, a floral scent cue, in eliciting orientation responses of moths. This research provides a new two-component lure for the alfalfa looper A.californica and for the armyworm S.albula for potential use in pest management. c � 2012 Society of Chemical Industry

István Szarukán - One of the best experts on this subject based on the ideXlab platform.

  • Phenylacetaldehyde: A chemical attractant for common green lacewings (Chrysoperla carnea s.l., Neuroptera: Chrysopidae)
    European Journal of Endocrinology, 2020
    Co-Authors: Miklós Tóth, Ferenc Szentkiralyi, András Bozsik, Agostino Letardi, Maria Rosaria Tabilio, Marcello Verdinelli, Pietro Zandigiacomo, Judit Jekisa, István Szarukán
    Abstract:

    Keywords. Neuroptera, Chrysopidae, Chrysoperla, green lacewings, attractant, Phenylacetaldehyde Abstract. At five sites in Hungary and Italy, traps baited with Phenylacetaldehyde caught significantly higher numbers (10 to 100 times more) of green lacewings than unbaited traps, which demonstrates that this compound is an attractant. Traps with three bait dispensers usually caught more than those with one dispenser, but the difference was significant only at two out of five test sites. There was no difference in the numbers caught by sticky delta and funnel traps baited with Phenylacetaldehyde. However, funnel traps could be adapted to catch living green lacewings. The vast majority of the specimens belonged to the Chrysoperla carnea spe- cies complex. Ch. carnea sensu lato dominated the catches at all sites. At some sites 3-11% of the insects caught were Ch. lucasina Lacroix. Phenylacetaldehyde-baited traps were attractive to both sexes, but generally more females were caught than males. Funnel traps baited with three dispensers of Phenylacetaldehyde caught green lacewing adults throughout the season in Hungary.

  • Development of a Female-Targeted Lure for the Box Tree Moth Cydalima perspectalis (Lepidoptera: Crambidae): a Preliminary Report
    Journal of Chemical Ecology, 2019
    Co-Authors: Béla Péter Molnár, István Szarukán, Antal Nagy, Sandor Koczor, Zsolt Kárpáti, Judit Csabai, Miklós Tóth
    Abstract:

    The box tree moth, Cydalima perspectalis, is an invasive pest in Europe causing damage on Buxus species. In this study, we aimed to develop a “bisexual” lure to attract both female and male moths. Based on a previous screening bioassay we tested methyl salicylate, Phenylacetaldehyde and eugenol as potential attractants in different combinations. The trapping results showed that both binary and ternary blends attracted male and female moths. Catches with these blends were comparable to catches with the synthetic pheromone. Subsequently we carried out single sensillum recordings, which proved the peripheral detection of the above-mentioned compounds on male and female antennae. To identify synergistic flower volatiles, which can be also attractive and can increase the trap capture, we collected flower headspace volatiles from 12 different flowering plant species. Several components of the floral scents evoked good responses from antennae of both females and males in gas chromatography-electroantennographic detection. The most active components were tentatively identified by gas chromatography coupled mass spectrometry as benzaldehyde, cis -ß-ocimene, (±)-linalool and phenethyl alcohol. These selected compounds in combination did not increase significantly the trap capture compared to the methyl salicylate- phenyacetaldehyde blend. Based on these results we discovered the first attractive blend, which was able to attract both adult male and female C. perspectalis in field conditions. These results will yield a good basis for the optimization and development of a practically usable bisexual lure against this invasive pest.

  • improving bisexual lures for the silver y moth autographa gamma l and related plusiinae lepidoptera noctuidae
    Acta Phytopathologica Et Entomologica Hungarica, 2019
    Co-Authors: Miklós Tóth, István Szarukán, Antal Nagy, Peter J Landolt, Julia Katalin Josvai
    Abstract:

    The addition of synthetic eugenol and benzyl acetate to the known floral chemical and moth attractant Phenylacetaldehyde synergized attraction of the silver Y moth Autographa gamma, an important no...

  • an improved female targeted semiochemical lure for the european corn borer ostrinia nubilalis hbn
    Acta Phytopathologica Et Entomologica Hungarica, 2016
    Co-Authors: Miklós Tóth, István Szarukán, Antal Nagy, T Abri, V Katona, Sz Kőrosi, T Nagy, A Szarvas, Sandor Koczor
    Abstract:

    The addition of synthetic 4-methoxy-2-phenethyl alcohol to the known attractant Phenylacetaldehyde synergized attraction of the European corn borer Ostrinia nubilalis, the blend invariably catching 3 to 5 times more than Phenylacetaldehyde on its own. Highest catches were recorded by the 1:1 blend. Both females and males were attracted, supposedly in the natural sex ratio of the local population. This improved bisex O. nubilalis attractant could be more efficient and more suitable for detection and monitoring purposes than previously know lures, making possible to draw more reliable plant protection decisions.

  • interaction of acetic acid and Phenylacetaldehyde as attractants for trapping pest species of moths lepidoptera noctuidae
    Pest Management Science, 2013
    Co-Authors: Peter J Landolt, Miklós Tóth, Robert L Meagher, István Szarukán
    Abstract:

    BACKGROUND: Phenylacetaldehyde is a flower volatile and attractant for many nectar-seeking moths. Acetic acid is a microbial fermentation product that is present in insect sweet baits. It is weakly attractive to some moths and other insects, but can be additive or synergistic with other compounds to make more powerful insect lures. RESULTS: Acetic acid and Phenylacetaldehyde presented together in traps made a stronger lure than either chemical alone for moths of the alfalfa looper Autographa californica (Speyer) and the armyworm Spodoptera albula (Walker). However, this combination of chemicals reduced captures of the cabbage looper mothTrichoplusiani (H ¨ ubner), the silver Y mothAutographa gamma (L.), MacDunnoughia confusa (Stephens) and the soybean looper moth Chrysodeixis includens (Walker) by comparison with Phenylacetaldehyde alone. CONCLUSION: These results indicate both positive and negative interactions of acetic acid, a sugar fermentation odor cue, and Phenylacetaldehyde, a floral scent cue, in eliciting orientation responses of moths. This research provides a new two-component lure for the alfalfa looper A.californica and for the armyworm S.albula for potential use in pest management. c � 2012 Society of Chemical Industry

Mingfu Wang - One of the best experts on this subject based on the ideXlab platform.

  • a Phenylacetaldehyde flavonoid adduct 8 c e phenylethenyl norartocarpetin exhibits intrinsic apoptosis and mapk pathways related anticancer potential on hepg2 smmc 7721 and qgy 7703
    Food Chemistry, 2016
    Co-Authors: Zongping Zheng, Mingfu Wang, Shuang Zhang, Jie Chen, Yang Xu
    Abstract:

    Abstract Norartocarpetin, quercetin and naringenin were found to effectively inhibit 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) formation through trapping its Phenylacetaldehyde and form their adducts in roast beef patties. Six adducts [8- C - or 6- C -( E -phenylethenyl) flavonoids] formed between Phenylacetaldehyde and three flavonoids were detected in roast beef patties by UPLC–MS analyses and compared with their synthetic references. These flavonoid–Phenylacetaldehyde adducts were synthesised and further subjected to cytotoxicity tests on three liver cancer cell lines HepG2, SMMC-7721 and QGY-7703. The adduct 8- C -( E -phenylethenyl)norartocarpetin ( NARA1 ) was found to significantly induce cancer cell death with IC 50 values about 7 μM. After pre-treating with MAPK and caspase inhibitors, alteration of the cell morphology and cleaved-PARP were detected in liver cancer cell lines administered with NARA1 . These data indicated that norartocarpetin could inhibit PhIP formation in roast beef patties and form norartocarpetin–Phenylacetaldehyde adducts. The adduct NARA1 has anticancer potential via intrinsic caspase-dependent and cell context-dependent MAPKs pathways.

  • inhibitory effects of selected dietary flavonoids on the formation of total heterocyclic amines and 2 amino 1 methyl 6 phenylimidazo 4 5 b pyridine phip in roast beef patties and in chemical models
    Food & Function, 2016
    Co-Authors: Qin Zhu, Mingfu Wang, Shuang Zhang, Jie Chen, Z P Zheng
    Abstract:

    In this study, the inhibitory effects of eight kinds of dietary flavonoids on the formation of heterocyclic amines (HAs) were investigated in roast beef patties. The results showed that most of them exhibited significant inhibition on both total HAs and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), one of the most abundant HAs. Among the studied flavonoids, phlorizin, epigallocatechin gallate (EGCG), and quercetin were found to be the most effective in both the reductions of total HAs (55–70%) and PhIP (60–80%). The reaction activity between the flavonoid and Phenylacetaldehyde, a key intermediate in PhIP formation, showed a good correlation with the inhibition of PhIP formation in an aqueous model system (R2 = 0.8904) and a di(ethylene) glycol reaction system (R2 = 0.6514). However, no significant correlation was found between the flavonoid antioxidant capacity and PhIP formation (R2 = 0.2359). The postulated adducts of flavonoids–Phenylacetaldehyde were further confirmed by LC-MS analysis in the chemical models. Since Phenylacetaldehyde is the chief intermediate in PhIP formation, these results suggest that the inhibitory effects of flavonoids on PhIP formation are mainly dependent on their abilities to trap Phenylacetaldehyde as opposed to their antioxidant capacities.

  • inhibition of heterocyclic amine formation by water soluble vitamins in maillard reaction model systems and beef patties
    Food Chemistry, 2012
    Co-Authors: Daniel Wong, Kawing Cheng, Mingfu Wang
    Abstract:

    Abstract The inhibitory activities of 11 water-soluble vitamins against heterocyclic amine formation were examined in a PhIP and a MeIQx producing chemical model. Six investigated vitamins (pyridoxiamine, pyridoxine, nicotinic acid, biotin, thiamine and l -ascorbic acid) out of the 11, exhibited significant inhibition (>40%) in both models. Pyridoxamine was the most potent inhibitor, and its inhibitory effect increased with increasing concentration in the model, although not in a linear manner. The activity of pyridoxamine, niacin and ascorbic acid was investigated using fried beef. Moderate inhibition (∼20%) of the formation of PhIP, 4,8-DiMeIQx and MeIQx was found for niacin and ascorbic acid; whereas pyridoxamine reduced the levels of all three HAs by ∼40%. GC–MS analysis showed that pyridoxamine significantly reduced the level of PhIP intermediate, Phenylacetaldehyde. LC–ESI–MS/MS analysis revealed that pyridoxamine directly reacts with Phenylacetaldehyde to form an adduct, whose structure was characterised by MS and NMR spectroscopy.

  • trapping of Phenylacetaldehyde as a key mechanism responsible for naringenin s inhibitory activity in mutagenic 2 amino 1 methyl 6 phenylimidazo 4 5 b pyridine formation
    Chemical Research in Toxicology, 2008
    Co-Authors: Kawing Cheng, Chi Chun Wong, Chi Kong Cho, Ivan K Chu, Konghung Sze, Feng Chen, Mingfu Wang
    Abstract:

    Chemical model reactions were carried out to investigate the mechanism of inhibition by a citrus flavonoid, naringenin, on the formation of 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP), the most abundant mutagenic heterocyclic amine found in foods. GC-MS showed that naringenin dose dependently reduced the level of Phenylacetaldehyde, a key intermediate on the pathway to the formation of PhIP. Subsequent LC-MS analyses of samples from a wide range of model systems consisting of PhIP precursors, including phenylalanine, glucose, and creatinine, suggested that naringenin scavenged Phenylacetaldehyde via adduct formation. An isotope-labeling study showed that the postulated adducts contain fragment(s) of phenylalanine origin. Direct reaction employing Phenylacetaldehyde and naringenin further confirmed the capability of naringenin to form adducts with Phenylacetaldehyde, thus reducing its availability for PhIP formation. Two of the adducts were subsequently isolated and purified. Their structure wa...

Carlo Ignazio Giovanni Tuberoso - One of the best experts on this subject based on the ideXlab platform.

  • traceability of satsuma mandarin citrus unshiu marc honey through nectar honey sac honey pathways of the headspace volatiles and semi volatiles chemical markers
    Molecules, 2016
    Co-Authors: Igor Jerković, Zvonimir Marijanovic, Marina Zekic, Lidija Svečnjak, Saša Prđun, Dragan Bubalo, Carlo Ignazio Giovanni Tuberoso
    Abstract:

    Headspace solid-phase microextraction (HS-SPME) and ultrasonic solvent extraction (USE), followed by GC-MS/FID, were applied for monitoring the nectar (NE)/honey-sac (HoS)/honey (HO) pathways of the headspace, volatiles, and semi-volatiles. The major NE (4 varieties of Citrus unshiu) headspace compounds were linalool, α-terpineol, 1H-indole, methyl anthranilate, and phenylacetonitrile. Corresponding extracts contained, among others, 1H-indole, methyl anthranilate, 1,3-dihydro-2H-indol-2-one and caffeine. The major HoS headspace compounds were linalool, α-terpineol, 1,8-cineole, 1H-indole, methyl anthranilate, and cis-jasmone. Characteristic compounds from HoS extract were caffeine, 1H-indole, 1,3-dihydro-2H-indol-2-one, methyl anthranilate, and phenylacetonitrile. However, HO headspace composition was significantly different in comparison to NE and HoS with respect to Phenylacetaldehyde and linalool derivatives abundance that appeared as the consequence of the hive conditions and the bee enzyme activity. C. unshiu honey traceability is determined by chemical markers: Phenylacetaldehyde, phenylacetonitrile, linalool and its derivatives, as well as 1H-indole, 1,3-dihydro-2H-indol-2-one, and caffeine.

  • Traceability of Satsuma Mandarin (Citrus unshiu Marc.) Honey through Nectar/Honey-Sac/Honey Pathways of the Headspace, Volatiles, and Semi-Volatiles: Chemical Markers
    Molecules (Basel Switzerland), 2016
    Co-Authors: Igor Jerković, Lidija Svečnjak, Saša Prđun, Dragan Bubalo, Zvonimir Marijanović, Marina Zekić, Carlo Ignazio Giovanni Tuberoso
    Abstract:

    Headspace solid-phase microextraction (HS-SPME) and ultrasonic solvent extraction (USE), followed by GC-MS/FID, were applied for monitoring the nectar (NE)/honey-sac (HoS)/honey (HO) pathways of the headspace, volatiles, and semi-volatiles. The major NE (4 varieties of Citrus unshiu) headspace compounds were linalool, α-terpineol, 1H-indole, methyl anthranilate, and phenylacetonitrile. Corresponding extracts contained, among others, 1H-indole, methyl anthranilate, 1,3-dihydro-2H-indol-2-one and caffeine. The major HoS headspace compounds were linalool, α-terpineol, 1,8-cineole, 1H-indole, methyl anthranilate, and cis-jasmone. Characteristic compounds from HoS extract were caffeine, 1H-indole, 1,3-dihydro-2H-indol-2-one, methyl anthranilate, and phenylacetonitrile. However, HO headspace composition was significantly different in comparison to NE and HoS with respect to Phenylacetaldehyde and linalool derivatives abundance that appeared as the consequence of the hive conditions and the bee enzyme activity. C. unshiu honey traceability is determined by chemical markers: Phenylacetaldehyde, phenylacetonitrile, linalool and its derivatives, as well as 1H-indole, 1,3-dihydro-2H-indol-2-one, and caffeine.

  • screening of coffea spp honey by different methodologies theobromine and caffeine as chemical markers
    RSC Advances, 2014
    Co-Authors: Igor Jerkovic, Zvonimir Marijanovic, Carlo Ignazio Giovanni Tuberoso, Piotr Marek Kuś, Marina Kranjac
    Abstract:

    Coffea spp. honey was screened by UV/VIS, HS-SPME/GC-MS/FID, USE/GC-MS/FID and HPLC-DAD. The direct HPLC-DAD methodology overcame the major limitations of the other methods used. The obtained results constitute a breakthrough since dominant xanthine derivatives were found (theobromine and caffeine with HPLC-DAD and caffeine by USE/GC-MS/FID). Phenylacetaldehyde was the major headspace compound.

Kawing Cheng - One of the best experts on this subject based on the ideXlab platform.

  • a novel potent inhibitor of 2 amino 1 methyl 6 phenylimidazo 4 5 b pyridine phip formation from chinese chive identification inhibitory effect and action mechanism
    Food Chemistry, 2021
    Co-Authors: Qi Wang, Feng Chen, Weiwei Cheng, Yifeng Zhang, Qingzheng Kang, Vemana Gowd, Yuanyuan Ren, Kawing Cheng
    Abstract:

    Differential solvent extraction and phytochemical profiling of Chinse chive were employed to identify its principal PhIP-formation inhibitory constituents. Six compounds (mangiferin, isorhamnetin, luteolin, rosmarinic acid, 6-methylcoumarin, and cyanidin-3-glucoside) were further analyzed in a PhIP-producing chemical model to identify the dominant inhibitor. Its inhibitory mechanism was investigated by assessing the contribution of antioxidation and scavenging of key PhIP precursor/intermediate. No significant correlation was observed between PhIP inhibition rates and antioxidant activities. Further evaluation of the novel potent inhibitor mangiferin revealed a highly significant correlation between its dose-dependent inhibition of PhIP formation and Phenylacetaldehyde scavenging. Finally, the proposed mechanism was corroborated through organic synthesis and structural elucidation of the mangiferin-Phenylacetaldehyde adduct. This study has identified a potent novel inhibitor of the most abundant HA in heat-processed food and characterized its action mechanism. These findings may provide insight for future studies on mitigation of dietary exposure to toxic Maillard products by polyphenolic phytochemicals.

  • inhibition of heterocyclic amine formation by water soluble vitamins in maillard reaction model systems and beef patties
    Food Chemistry, 2012
    Co-Authors: Daniel Wong, Kawing Cheng, Mingfu Wang
    Abstract:

    Abstract The inhibitory activities of 11 water-soluble vitamins against heterocyclic amine formation were examined in a PhIP and a MeIQx producing chemical model. Six investigated vitamins (pyridoxiamine, pyridoxine, nicotinic acid, biotin, thiamine and l -ascorbic acid) out of the 11, exhibited significant inhibition (>40%) in both models. Pyridoxamine was the most potent inhibitor, and its inhibitory effect increased with increasing concentration in the model, although not in a linear manner. The activity of pyridoxamine, niacin and ascorbic acid was investigated using fried beef. Moderate inhibition (∼20%) of the formation of PhIP, 4,8-DiMeIQx and MeIQx was found for niacin and ascorbic acid; whereas pyridoxamine reduced the levels of all three HAs by ∼40%. GC–MS analysis showed that pyridoxamine significantly reduced the level of PhIP intermediate, Phenylacetaldehyde. LC–ESI–MS/MS analysis revealed that pyridoxamine directly reacts with Phenylacetaldehyde to form an adduct, whose structure was characterised by MS and NMR spectroscopy.

  • trapping of Phenylacetaldehyde as a key mechanism responsible for naringenin s inhibitory activity in mutagenic 2 amino 1 methyl 6 phenylimidazo 4 5 b pyridine formation
    Chemical Research in Toxicology, 2008
    Co-Authors: Kawing Cheng, Chi Chun Wong, Chi Kong Cho, Ivan K Chu, Konghung Sze, Feng Chen, Mingfu Wang
    Abstract:

    Chemical model reactions were carried out to investigate the mechanism of inhibition by a citrus flavonoid, naringenin, on the formation of 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP), the most abundant mutagenic heterocyclic amine found in foods. GC-MS showed that naringenin dose dependently reduced the level of Phenylacetaldehyde, a key intermediate on the pathway to the formation of PhIP. Subsequent LC-MS analyses of samples from a wide range of model systems consisting of PhIP precursors, including phenylalanine, glucose, and creatinine, suggested that naringenin scavenged Phenylacetaldehyde via adduct formation. An isotope-labeling study showed that the postulated adducts contain fragment(s) of phenylalanine origin. Direct reaction employing Phenylacetaldehyde and naringenin further confirmed the capability of naringenin to form adducts with Phenylacetaldehyde, thus reducing its availability for PhIP formation. Two of the adducts were subsequently isolated and purified. Their structure wa...