Publications by authors named "Lishuang Lv"

29 Publications

  • Page 1 of 1

Comparison of functional and structural properties of ginkgo seed protein dried by spray and freeze process.

J Food Sci Technol 2021 Jan 28;58(1):175-185. Epub 2020 May 28.

Department of Food Science and Technology, School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, No. 2 Xuelin Road, Qixia, Nanjing, 210097 People's Republic of China.

The influences of spray-drying and freeze-drying processes on functional properties of ginkgo seed proteins (GSP) were systematically investigated. It was revealed that GSP dried by spray (SGSP) displays an significantly improved water holding capacity and superior emulsifying properties than the freezing-drying GSP (FGSP), whereas, the oil binding capacity is higher in FGSP. The difference in properties of SGSP and FGSP can be attributed to their different structural characteristics. Comparing with FGSP, SGSP was demonstrated having more disulfide bonds, more amorphous and less ordered structure, accounted for big differences in functional properties. With the outstanding functional characteristics, GSP could be potentially applied in oil-in-water type food system, such as milk and mayonnaise. Finally, it is important to choose the suitable drying method according to the requirements of the specific food system.
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http://dx.doi.org/10.1007/s13197-020-04527-xDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7813916PMC
January 2021

Inhibitory Activity on the Formation of Reactive Carbonyl Species in Edible Oil by Synthetic Polyphenol Antioxidants.

J Agric Food Chem 2021 Jan 17. Epub 2021 Jan 17.

Spice and Beverage Research Institute, Chinese Academy of Tropical Agricultural Sciences, Wanning, Hainan 571533, People's Republic of China.

Food lipids play an important role in food quality, and their attributes contribute to texture, flavor, and nutrition. However, high-temperature processing leads to lipid peroxidation, degradation, and the formation of reactive carbonyl species (RCS), such as acrolein (ACR), glyoxal (GO), and methylglyoxal (MGO). We investigated the changes in the peroxidation value (POV), Rancimat induction time, formation and total amount of RCS, and inhibitory effects of synthetic polyphenol antioxidants on ACR/GO/MGO in plant oils during heating processing through an accelerated oxidation test using Rancimat. With increasing temperature and heating time, the amounts of ACR, GO, and MGO in oil increased and the level of ACR was about several times higher than that of GO and MGO. We also found that some amounts of ACR, GO, and MGO were produced at the initial stage before reaching the peak value of POV, even before oil oxidative rancidity, and the common antioxidant butyl hydroxyanisole (BHA)/butylated hydroxytoluene (BHT) could not remove them once they were generated. This is first time to purify PG-ACR-MGO and elucidate the structure based on analysis of their high resolution mass spectrometry and H, C, and two-dimensional nuclear magnetic resonance. We further found that PG rather than BHT and BHA efficiently trapped ACR, OG, and MGO to form adducts in oil and roasted beef burgers with corn oil. Additionally, after incubation at 80 °C, the trapping order of PG was as follows: ACR, MGO, and GO, and the adduct of PG-ACR was formed within 1 min; after 10 min, PG-MGO was generated; and three adducts formed at 15 min. However, PG could not trap ACR, GO, or MGO to form adducts at room temperature. This study provided novel knowledge to advance our understanding of the ability of synthetic polyphenol antioxidants to scavenge RCS simultaneously, such as ACR, MGO, and GO. Our findings demonstrated that PG, as an inhibitor of RCS, is suitable for medium- and high-temperature food processing but not for normal-temperature storage.
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http://dx.doi.org/10.1021/acs.jafc.0c07248DOI Listing
January 2021

Trapping of Acrolein by Curcumin and the Synergistic Inhibition Effect of Curcumin Combined with Quercetin.

J Agric Food Chem 2021 Jan 29;69(1):294-301. Epub 2020 Dec 29.

Department of Food Science and Technology, School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, 2 Xuelin Road, Nanjing 210023, P. R. China.

Acrolein (ACR) is a toxic unsaturated aldehyde that is formed during different steps of thermal food processing. Here, we explored the kinetics of curcumin and ACR and elucidated the pathway of curcumin trapping ACR by preparing a mono-adduct of ACR (CMA-1) conjugated with curcumin. The synergistic scavenging effect and mechanism of curcumin combined with quercetin on ACR was analyzed by liquid chromatography-tandem mass spectrometry (LC-MS/MS). Comparing the uses of curcumin and quercetin both individually and in combination, we found that quercetin in combination resulted in more curcumin being transformed into CMA-2, while curcumin in combination made the amount of di-ACR conjugated to quercetin (QDA) increase. We also added combined curcumin and quercetin into grilled chicken wings to demonstrate that curcumin and quercetin could scavenge ACR by forming their own ACR adducts and antioxidant activity during the process. Our results have noted a new strategy, in which some combinations of dietary polyphenols might contribute to the removal of toxic ACR produced during thermal food processing.
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http://dx.doi.org/10.1021/acs.jafc.0c06692DOI Listing
January 2021

Trapping Acrolein by Theophylline/Caffeine and Their Metabolites from Green Tea and Coffee in Mice and Humans.

J Agric Food Chem 2020 Dec 30;68(49):14471-14479. Epub 2020 Nov 30.

Department of Food Science and Technology, School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, 2# Xuelin Road, Nanjing 210023, P.R. China.

Acrolein (ACR) is found exogenously as a widespread environmental pollutant and endogenously, where it is thought to be involved as a pathogenic factor in the progression of many pathological conditions. Eliminating ACR by dietary-active substances has been found to be one potential strategy to prevent ACR-associated chronic diseases. This study first compared the scavenging ACR efficacy of four purine alkaloids, theophylline (TP), paraxanthine (PXT), theobromine (TB), and caffeine (CAF), and then, TP, CAF, and their metabolites were investigated for their ability to trap ACR . Our results indicated that TP, which possesses an -NH moiety at the N-7 position, exhibits the best ACR-trapping capacity , while CAF has a slight ability to trap ACR due to the substitutions by -CH at the N-1, N-3, and N-7 positions. After oral administration of TP or CAF, the ACR adducts of TP and the metabolites of TP or CAF (e.g., mono- and di-ACR-TP, mono-ACR-1,3-DMU, and mono-ACR-1-MU) were detected in urinary samples obtained from both TP- and CAF-treated mouse groups by using ultra-performance liquid chromatography-tandem mass spectrometry. The quantification studies demonstrated that TP and its metabolites significantly trapped ACR in a dose-dependent manner . Furthermore, we also detected those ACR adducts of TP and TP/CAF's metabolites in human urine after four cups of green tea (2 g tea leaf/cup) or two cups of coffee (4 g coffee/cup) were consumed per day. Those results indicated that dietary TP or CAF has the potential capacity to scavenge ACR
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http://dx.doi.org/10.1021/acs.jafc.0c05483DOI Listing
December 2020

Chemical composition, structural and functional properties of soluble dietary fiber obtained from coffee peel using different extraction methods.

Food Res Int 2020 10 26;136:109497. Epub 2020 Jun 26.

Department of Food Science and Technology, School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, 2# Xuelin Road, Nanjing 210023, China. Electronic address:

This study aimed to evaluate the effects of chemical, enzymatic, chemical-enzymatic, ultrasound-assisted enzymatic, and shear emulsifying-assisted enzymatic extraction methods on the physicochemical, structural, and functional properties of soluble dietary fiber from coffee peel. We found that the highest extraction yield of soluble dietary fiber was obtained using the shear emulsifying-assisted enzymatic method, and that similar protein contents were obtained from coffee peel using the enzymatic and shear emulsifying-assisted enzymatic methods. Compared with the other extraction methods, shear emulsifying-assisted enzymatic processing resulted in a higher water-holding capacity (7.05 g/g) and oil-holding capacity (3.61 g/g), but a lower emulsifying capacity (58.50%) when compared with that of chemical, enzymatic, and chemical-enzymatic processings. The soluble dietary fiber obtained from coffee peel using shear emulsifying-assisted enzymatic extraction was also characterized by the highest glucose absorption activity (228.06 mg/g), and enzymatic processing resulted in the highest nitrite ion absorption capacity (10.09 mg/g, pH = 2). These results indicated that shear emulsifying-assisted enzymatic extraction method was the most appropriate extraction method for coffee peel soluble dietary fiber.
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http://dx.doi.org/10.1016/j.foodres.2020.109497DOI Listing
October 2020

Trapping Methylglyoxal by Myricetin and Its Metabolites in Mice.

J Agric Food Chem 2020 Sep 19;68(35):9408-9414. Epub 2020 Aug 19.

Laboratory for Functional Foods and Human Health, Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University, North Carolina Research Campus, 500 Laureate Way, Kannapolis, North Carolina 28081, United States.

Trapping of methylglyoxal (MGO) has been determined to be one of the potential mechanisms for dietary polyphenols to prevent chronic diseases. In this study, myricetin was demonstrated to efficiently trap MGO to generate mono- and di-MGO adducts under conditions. Furthermore, the mono- and di-MGO adducts of myricetin were detected in urine and fecal samples collected from myricetin-treated mice based on LC-MS analysis. More importantly, the mono-MGO adducts of the mono- and di-methylated myricetin were also found in these mouse samples. Further dose-dependent studies demonstrated that myricetin and its methylated metabolites significantly trapped MGO in a dose-dependent manner with the 400 mg/kg dose having the highest trapping efficacy (mono-MGO-myricetin: 272.0 ± 90.9 nM in urine and 1.05 ± 0.67 μg/g in feces; mono-MGO-mono-Me-myricetin: 135.2 ± 77.6 nM in urine and 1.16 ± 0.65 μg/g in feces; and mono-MGO-di-Me-myricetin: 17.0 ± 5.9 nM in urine and 0.19 ± 0.04 μg/g in feces) compared to the 100 and 200 mg/kg doses. In conclusion, this study demonstrates for the first time the trapping efficacy of myricetin, suggesting that intake of myricetin-containing foods has the potential to scavenge MGO and to prevent MGO-induced harmful effects to human health.
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http://dx.doi.org/10.1021/acs.jafc.0c03471DOI Listing
September 2020

Acrolein-Trapping Mechanism of Theophylline in Green Tea, Coffee, and Cocoa: Speedy and Successful.

J Agric Food Chem 2020 Sep 25;68(36):9718-9724. Epub 2020 Aug 25.

Department of Food Science and Technology, School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, 2# Xuelin Road, Nanjing 210023, P. R. China.

Increasing evidence has identified the unsaturated aldehyde acrolein (ACR) as the potential factor that causes deoxyribonucleic acid cross-linking and the development of chronic diseases. The objective of this study was to investigate the mechanism by which theophylline (TP) scavenges ACR for the first time. TP efficiently scavenged ACR through forming adducts, which was demonstrated in a system in which TP was incubated with ACR at different ratios for different times for liquid chromatography with tandem mass spectrometry. Then, the mono- and di-ACR-TP adducts were purified, and their structures were elucidated by high-resolution mass spectrometry and nuclear magnetic resonance analysis. We found that the ACR residue on mono-ACR-TP further trapped one more ACR and formed di-ACR-TP adducts. Furthermore, mono- and di-ACR-TP had similar time-dependent ACR-scavenging activity to TP. Finally, we demonstrated that green tea, coffee, and cocoa inhibited ACR by trapping ACR to form mono- and di-ACR-TP adducts during the incubation of green tea, coffee, and cocoa with ACR.
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http://dx.doi.org/10.1021/acs.jafc.0c03895DOI Listing
September 2020

Mechanistic studies of inhibition on acrolein by myricetin.

Food Chem 2020 Apr 11;323:126788. Epub 2020 Apr 11.

Spice and Beverage Research Institute, Chinese Academy of Tropical Agricultural Sciences, Wanning, Hainan 571533, China. Electronic address:

Acrolein (ACR) is an unsaturated aldehyde with high activity and toxicity and is produced in vivo and in food. This study investigated the impact of B-ring structure on the trapping of ACR by flavonols and the trapping mechanism and efficacy of ACR by myricetin. Galangin, kaempferol, quercetin, and myricetin, which possess the same A- and C-ring but different numbers of -OH groups on the B-ring, were selected for this study. Our results suggested that increasing the number of -OH groups on the B-ring can enhance the ACR trapping efficacy of flavonol and myrectin was identified as the most active flavonol. The adducts of myricetin with ACR under different ratios and incubation times were analyzed using LC-MS/MS. We also purified and identified the major mono- and di-ACR-myricetin adducts. Furthermore, myricetin could dose-dependently inhibit the formation of ACR in cookies through the formation of mono- and di-ACR adducts.
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http://dx.doi.org/10.1016/j.foodchem.2020.126788DOI Listing
April 2020

Translating In Vitro Acrolein-Trapping Capacities of Tea Polyphenol and Soy Genistein to In Vivo Situation is Mediated by the Bioavailability and Biotransformation of Individual Polyphenols.

Mol Nutr Food Res 2020 01 8;64(1):e1900274. Epub 2019 Nov 8.

Laboratory for Functional Foods and Human Health, Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University, North Carolina Research Campus, 500 Laureate Way, Kannapolis, NC, 28081, USA.

Scope: Acrolein (ACR) is a highly toxic unsaturated aldehyde. Humans are both endogenously and exogenously exposed to ACR. Long-term exposure to ACR leads to various chronic diseases. Dietary polyphenols have been reported to be able to attenuate ACR-induced toxicity in vitro via formation of ACR-polyphenol conjugates. However, whether in vitro ACR-trapping abilities of polyphenols can be maintained under in vivo environments is still unknown.

Methods And Results: Two most commonly consumed dietary polyphenols, (-)-epigallocatechin-3-gallate (EGCG) from tea and genistein from soy, are evaluated for their anti-Acrolein behaviors both in vitro and in mice. Tea EGCG exerts a much higher capacity to capture ACR than soy genistein in vitro. But translation of in vitro anti-ACR activity into in vivo is mainly mediated by bioavailability and biotransformation of individual polyphenols. It is found that 1) both absorbed EGCG and genistein can trap endogenous ACR by forming mono-ACR adducts and eventually be excreted into mouse urine; 2) both absorbed EGCG and genistein can produce active metabolites, methyl-EGCG (MeEGCG) and orobol, to scavenge endogenous ACR; 3) both MeEGCG and non-absorbed EGCG show ability to trap ACR in the gut; 4) considerable amounts of microbial metabolites of genistein display enhanced anti-ACR capacity both in the body and in the gut, compared to genistein; and 5) biotransformation of genistein is able to boost its in vivo anti-ACR capacity, compared to EGCG.

Conclusion: The findings demonstrate that in vivo anti-ACR ability of dietary polyphenols cannot be reflected solely based on their in vitro ability. The bioavailability and biotransformation of individual polyphenols, and especially the gut microbiome, contribute to in vivo anti-ACR ability of dietary polyphenols.
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http://dx.doi.org/10.1002/mnfr.201900274DOI Listing
January 2020

Scavenging of Acrolein by Food-Grade Antioxidant Propyl Gallate in a Model Reaction System and Cakes.

J Agric Food Chem 2019 Aug 29;67(31):8520-8526. Epub 2019 Jul 29.

Department of Food Science and Technology, School of Food Science and Pharmaceutical Engineering , Nanjing Normal University , 2 Xuelin Road , Nanjing , Jiangsu 210023 , People's Republic of China.

Reactive carbonyl species (RCS), such as acrolein (ACR), glyoxal (GO), and methylglyoxal (MGO), have received extensive attention recently as a result of their high activity and toxicity and . In the present study, propyl gallate (PG), a common food antioxidant, was found to effectively trap more ACR than butylated hydroxytoluene and butylated hydroxyanisole through the formation of mono-ACR adducts (PG-ACR) and di-ACR adducts (PG-2ACR). The two adducts were successfully purified, and their structures were elucidated on the basis of their high-resolution mass spectrometry and H, C, and two-dimensional nuclear magnetic resonance data. We further identified that PG-ACR had the ability to continue to trap GO and MGO to form PG-ACR-GO and PG-ACR-MGO, respectively, by liquid chromatography-tandem mass spectrometry (LC-MS/MS). Furthermore, we verified that PG could inhibit the production of ACR, GO, and MGO via trapping these RCS simultaneously to form the corresponding adducts in pound cakes using LC-MS/MS.
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http://dx.doi.org/10.1021/acs.jafc.9b03486DOI Listing
August 2019

Trapping of glyoxal by propyl, octyl and dodecyl gallates and their mono-glyoxal adducts.

Food Chem 2018 Dec 4;269:396-403. Epub 2018 Jul 4.

Department of Food Science and Technology, Nanjing Normal University, 122# Ninghai Road, Nanjing 210097, PR China. Electronic address:

Glyoxal (GO) is one of the major toxic intermediates generated during lipid oxidation and degradation. We investigated the inhibitory activities and mechanisms of propyl, octyl, and dodecyl gallates (PG, OG, and DG) on the formation of GO in buffer and during thermo-processing of corn oil, and the anti-carbonyl and antioxidative activities of the mono-GO adducts of PG, OG, and DG. Our results suggested that alkyl gallates could more effectively trap GO than gallic acid. The major mono-GO adducts of PG, OG, and DG were purified and their structures were elucidated based on their H, C, 2D-NMR, and HRMS data. We further demonstrated that the mono-GO (MG) adducts retained the anti-carbonyl and antioxidative activities. This is the first study to demonstrate that alkyl gallates, the popular food additives, could prevent not only food oxidation, but also the formation of toxic reactive carbonyl species and their corresponding advanced glycation end products (AGEs) during food processing.
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http://dx.doi.org/10.1016/j.foodchem.2018.07.030DOI Listing
December 2018

Dual effects of propyl gallate and its methylglyoxal adduct on carbonyl stress and oxidative stress.

Food Chem 2018 Nov 16;265:227-232. Epub 2018 Apr 16.

Department of Food Science and Technology, Nanjing Normal University, 122# Ninghai Road, Nanjing 210097, PR China. Electronic address:

In the present study, we investigated the trapping of methylglyoxal (MGO) by propyl gallate (PG), a known food grade antioxidant, and the anti-carbonyl and anti-oxidative properties of the mono-MGO adduct of PG (MM-PG). Our result indicated that more than 77.5% MGO was suppressed by PG after a 30 min incubation of PG with MGO, which was much more effective than gallic acid (15.2%). For the first time, MM-PG was purified, and its structure was elucidated based on the analysis of its H, C, and 2D-NMR data. We also demonstrated that MM-PG had strong anti-oxidative and anti-carbonyl activities. Furthermore, PG could trap the MGO generated during the preparation of roasted pork, and both mono- and di- MGO adducts of PG were detected in the roasted pork system using LC/MS technique. Thus, PG could be widely applied in the food system for inhibiting the formation of both carbonyl species and oxidative species.
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http://dx.doi.org/10.1016/j.foodchem.2018.04.045DOI Listing
November 2018

A new method to prepare and redefine black tea thearubigins.

J Chromatogr A 2018 Aug 28;1563:82-88. Epub 2018 May 28.

Laboratory for Functional Foods and Human Health, Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University, North Carolina Research Campus, 500 Laureate Way, Kannapolis, NC 28081, United States. Electronic address:

Thearubigins (TRs) are the major components of black tea, which are formed during the fermentation reactions. Although anti-inflammatory and anti-cancer activities of TRs have been reported, the prepared TRs according to the literature methods still contain many floating peaks. It is puzzling whether the observed activities are from TRs or these floating peaks. Thus, it is urgent to develop a method to prepare pure TRs and redefine them. In the present study, we developed a new method, the combination of caffeine precipitation and Sephadex LH-20 column chromatography, to prepare pure TRs. The floating peaks on the hump of the crude TRs were removed, and pure TRs were prepared. The chemical profile of the floating peaks was established using LC/MS, and the major compounds in this fraction were identified as apigenin glycosides, quercetin glycosides, kaempferol glycosides, theaflavins, theasinensin, and galloylglucoses based on the analysis of their tandem mass spectra and in comparison with literature data. This study will pave the way to further study the chemistry and biological activities of TRs and the health effects of black tea consumption.
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http://dx.doi.org/10.1016/j.chroma.2018.05.060DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6008242PMC
August 2018

Novel Theaflavin-Type Chlorogenic Acid Derivatives Identified in Black Tea.

J Agric Food Chem 2018 Apr 21;66(13):3402-3407. Epub 2018 Mar 21.

Laboratory for Functional Foods and Human Health, Center for Excellence in Post-Harvest Technologies , North Carolina Agricultural and Technical State University, North Carolina Research Campus , 500 Laureate Way , Kannapolis , North Carolina 28081 , United States.

Consumption of black tea contributed to many health benefits including the prevention of heart disease and certain types of cancer. However, the chemical composition of black tea has not been fully explored. Most studies have examined different interactions between the four major tea catechins, and limited studies have investigated the interaction between catechins and other components in tea. In the present study, we tested our hypothesis that the ortho-dihydroxyl structure of chlorogenic acid (CGA) could react with the vic-trihydroxy structure of (-)-epigallocatechin 3-gallate (EGCG) and (-)-epigallocatechin (EGC) to generate theaflavin-type of compounds during black tea fermentation. The reaction between CGA and EGCG or EGC was catalyzed by horseradish peroxidase (POD) in the presence of HO. Two theaflavin-type compounds EGCG-CGA and EGC-CGA were purified using a Sephadex LH-20 column. Their structures were elucidated on the basis of the analysis of their MS and 1D- and 2D-NMR spectroscopic data. Furthermore, the existence of these two novel compounds was characterized by LC/MS/MS analysis. We also found that EGCG-CGA and EGC-CGA had very similar inhibitory effects on the growth of human colon cancer cells with that of theaflavin 3,3'-digallate. These findings shed light on the interactions between the major bioactive compounds, catechins, and other minor compounds in tea. The confirmation of the presence of this type of reaction in black tea may provide more understanding of the complexity of black tea chemistry.
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http://dx.doi.org/10.1021/acs.jafc.7b06044DOI Listing
April 2018

Additive Capacity of [6]-Shogaol and Epicatechin To Trap Methylglyoxal.

J Agric Food Chem 2017 Sep 18;65(38):8356-8362. Epub 2017 Sep 18.

Laboratory for Functional Foods and Human Health, Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University , North Carolina Research Campus, 500 Laureate Way, Kannapolis, North Carolina 28081, United States.

Methylglyoxal (MGO), a reactive dicarbonyl species, is thought to contribute to the development of long-term pathological diabetes as a direct toxin or as an active precursor of advanced glycation end products (AGEs). Trapping MGO by dietary phenols to inhibit the MGO induced AGE formation is an approach for alleviating diabetic complications. The present study investigated whether dietary compounds with different structures and active sites have the additive capacity to trap MGO. Ginger phenolic constituent [6]-shogaol and tea flavonoid (-)-epicatechin were selected and tested under simulated physiological conditions, showing that they additively trapped about 41% MGO at a concentration of 10 μM within 24 h. Furthermore, whether [6]-shogaol and epicatechin can retain their MGO trapping efficacy in vivo or a biotransformation limits their MGO trapping capacity remain virtually unknown. An acute mouse study was carried out by giving a single dose of [6]-shogaol, epicatechin, and the combination of both ([6]-shogaol + epicatechin) through oral gavage. A mono-MGO adduct of [6]-shogaol was identified from [6]-shogaol and [6]-shogaol + epicatechin treated mice, and mono- and di-MGO adducts of epicatechin and its metabolite, 3'-O-methyl epicatichin, were detected in urine samples collected from epicatechin and [6]-shogaol + epicatechin treated mice. To our knowledge, this is the first study demonstrating the additive MGO trapping efficacy of [6]-shogaol and epicatechin and that [6]-shogaol and epicatechin retained their MGO trapping capacity in mice.
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http://dx.doi.org/10.1021/acs.jafc.7b02917DOI Listing
September 2017

Levels and formation of α-dicarbonyl compounds in beverages and the preventive effects of flavonoids.

J Food Sci Technol 2017 Jun 27;54(7):2030-2040. Epub 2017 Apr 27.

Department of Food Science and Technology, Nanjing Normal University, 122# Ninghai Road, Nanjing, 210097 People's Republic of China.

Abstract: Methylglyoxal (MGO) and glyoxal (GO), α-dicarbonyl compounds found in the Maillard reaction, progressively and irreversibly modify proteins. Beverages are an exogenous source of α-dicarbonyl compounds and may potentially increase MGO and GO levels in vivo. Using GC-FID method, we detected the MGO and GO contents of 86 beverages in Chinese supermarkets. The highest MGO and GO 587.5 µg/100 mL and 716.7 µg/100 mL respectively found in soyamilk and coffee. Herbal beverages, which contained bioactive components, had lower average levels of MGO (48.1 µg/100 mL) and GO (25.9 µg/100 mL). A box-and-whisker plot was used to display variation of the same group drinks, and comparing distributions between six different groups. It was further discovered that fat, protein and flavonoids, in addition to sweeteners, had notable effects on the formation of MGO and GO in soybean milk. The result of LC/MS indicated that quercetin could prevent the formation of MGO by trapping MGO to form the mono-MGO and di-MGO adducts during soybean milk manufacturing.

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http://dx.doi.org/10.1007/s13197-017-2639-zDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5495730PMC
June 2017

Influence of Quercetin and Its Methylglyoxal Adducts on the Formation of α-Dicarbonyl Compounds in a Lysine/Glucose Model System.

J Agric Food Chem 2017 Mar 6;65(10):2233-2239. Epub 2017 Mar 6.

Department of Food Science and Technology, Nanjing Normal University , 122 Ninghai Road, Nanjing 210097, People's Republic of China.

Increasing evidence has identified α-dicarbonyl compounds, the reactive intermediates generated during Maillard reaction, as the potential factors to cause protein glycation and the development of chronic diseases. Therefore, there is an urgent need to decrease the levels of reactive dicarbonyl compounds in foods. In this study, we investigated the inhibitory effect of quercetin, a major dietary flavonoid, and its major mono- and di-MGO adducts on the formation of dicarbonyl compounds, such as methylglyoxal (MGO) and glyoxal (GO), in a lysine/glucose aqueous system, a model system to reflect the Maillard reaction in food process. Our result indicated that quercetin could efficiently inhibit the formation of MGO and GO in a time-dependent manner. Further mechanistic study was conducted by monitoring the formation of quercetin oxidation and conjugation products using LC-MS/MS. Quercetin MGO adducts, quercetin quinones, and the quinones of quercetin MGO adducts were detected in the system, indicating quercetin plays a dual role in inhibiting the formation of MGO and GO by scavenging free radicals generated in the system and trapping of MGO and GO to form MGO adducts. In addition, we prepared the mono- and di-MGO quercetin adducts and investigated their antioxidant activity and trapping capacity of MGO and GO. Our results indicated that both mono- and di-MGO quercetin adducts could scavenge the DPPH radical in a dose-dependent manner with >40% DPPH scavenged by the MGO adducts at 10 μM, and the di-MGO quercetin adduct could further trap MGO to generate tri-MGO adducts. Therefore, we demonstrate for the first time that quercetin MGO adducts retain the antioxidant activity and trapping capacity of reactive dicarbonyl species.
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http://dx.doi.org/10.1021/acs.jafc.6b05811DOI Listing
March 2017

Chemical components from the haulm of Artemisia selengensis and the inhibitory effect on glycation of β-lactoglobulin.

Food Funct 2015 Jun;6(6):1841-6

Department of Food Science and Technology, Ginling College, Nanjing Normal University, 122# Ninghai Road, Nanjing, 210097, P. R. China.

Artemisia selengensis (AS) has been traditionally used as both food and medicine for thousands of years in China. In our studies, l-tryptophan was first isolated from the haulm of AS together with luteolin, rutin, and kaempferol-3-O-glucuronide. Their structures were elucidated by spectroscopic methods including HRMS, 1D and 2D NMR. Three flavonoid compounds showed satisfactory suppression effects on the formation of advanced glycation end products (AGEs) in β-lactoglobulin-lactose/MGO/GO model systems, and their anti-glycation activities exhibited a dose-dependent manner. Among these compounds, kaempferol-3-O-glucuronide was demonstrated to be the strongest inhibitor against the formation of AGEs.
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http://dx.doi.org/10.1039/c5fo00117jDOI Listing
June 2015

Glycation of β-lactoglobulin and antiglycation by genistein in different reactive carbonyl model systems.

Food Chem 2015 Sep 11;183:36-42. Epub 2015 Mar 11.

Department of Food Science and Technology, Nanjing Normal University, 122# Ninghai Road, Nanjing 210097, PR China. Electronic address:

Advanced glycation end products (AGEs), which are formed in β-lactoglobulin (β-lg) glycation systems via the Maillard reaction, have been implicated in diabetes-related long-term complications. In the present study, we found that reaction conditions, including temperature, time, pH, reactant type and molar ratio of beta-lg to a sugar/MGO/GO, can significantly affect the formation of AGEs. Using SDS-PAGE, we further demonstrated that genistein, a natural isoflavone found in a number of plants including soybeans and kudzu, can efficiently inhibit cross-links of the glycated β-lg, and suppress the formation AGEs in a dose-dependent manner by trapping reactive dicarbonyl compounds. The products formed from genistein and methylglyoxal (MGO) in the β-lg-MGO assay were analyzed using LC/MS. Both mono-MGO and di-MGO adducts of genistein were detected with this method.
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http://dx.doi.org/10.1016/j.foodchem.2015.02.122DOI Listing
September 2015

Quercetin inhibits advanced glycation end product formation by trapping methylglyoxal and glyoxal.

J Agric Food Chem 2014 Dec 8;62(50):12152-8. Epub 2014 Dec 8.

Department of Food Science and Technology, Ginling College, Nanjing Normal University , 122 Ninghai Road, Nanjing 210097, People's Republic of China.

Methylglyoxal (MGO) and glyoxal (GO) not only are endogenous metabolites but also exist in exogenous resources, such as foods, beverages, urban atmosphere, and cigarette smoke. They have been identified as reactive dicarbonyl precursors of advanced glycation end products (AGEs), which have been associated with diabetes-related long-term complications. In this study, quercetin, a natural flavonol found in fruits, vegetables, leaves, and grains, could effectively inhibit the formation of AGEs in a dose-dependent manner via trapping reactive dicarbonyl compounds. More than 50.5% of GO and 80.1% of MGO were trapped at the same time by quercetin within 1 h under physiological conditions. Quercetin and MGO (or GO) were combined at different ratios, and the products generated from this reaction were analyzed with LC-MS. Both mono-MGO and di-MGO adducts of quercetin were detected in this assay using LC-MS, but only tiny amounts of mono-GO adducts of quercetin were found. Additionally, di-MGO adducts were observed as the dominant product with prolonged incubation time. In the bovine serum albumin (BSA)-MGO/GO system, quercetin traps MGO and GO directly and then significantly inhibits the formation of AGEs.
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http://dx.doi.org/10.1021/jf504132xDOI Listing
December 2014

Purification, antioxidant activity and antiglycation of polysaccharides from Polygonum multiflorum Thunb.

Carbohydr Polym 2014 Jan 8;99:765-73. Epub 2013 Sep 8.

Department of Food Science and Technology, Ginling College, Nanjing Normal University, 122# Ninghai Road, Nanjing 210097, China. Electronic address:

Polysaccharides, one of the most important constituents in Polygonum multiflorum Thunb, a famous Chinese medicinal herb, were isolated by DEAE-52, Sepharose 4B and Sephacryl S-300 column chromatography. Two polysaccharides (PMP-1 and PMP-2) were identified as homogeneous in molecular weight with HPLC. The molecular weights were 4.8 × 10(2) and 6.1 × 10(2) kDa, respectively. Antioxidant activity tests were performed with two polysaccharides at concentrations of 0.1-1.5mg/mL. The results indicated that the inhibitory activity on oxidation and glycation exhibited a dose-dependent response. PMP-2 exhibited a much stronger antioxidant capacity against free radical, lipid oxidation and protein glycation. The IC₅₀ values of PMP-2 were 0.47, 0.6 and 0.93 mg/mL for superoxide anion scavenging, hydroxyl radical scavenging, and hydroxyl peroxide scavenging, respectively. The inhibitory ability of PMP-2 on lipid oxidation was most markedly in rat liver, followed by heart and kidney. Meanwhile, PMP-2 also showed satisfactory suppression of AGEs formation. This suggested that the polysaccharides present in PM can contribute to the biological effects.
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http://dx.doi.org/10.1016/j.carbpol.2013.09.007DOI Listing
January 2014

6-gingerdiols as the major metabolites of 6-gingerol in cancer cells and in mice and their cytotoxic effects on human cancer cells.

J Agric Food Chem 2012 Nov 6;60(45):11372-7. Epub 2012 Nov 6.

Department of Food Science and Technology, Ginling College, Nanjing Normal University , 122# Ninghai Road, Nanjing 210097, P. R. China.

6-Gingerol, a major pungent component of ginger (Zingiber officinale Roscoe, Zingiberaceae), has been reported to have antitumor activities. However, the metabolic fate of 6-gingerol and the contribution of its metabolites to the observed activities are still unclear. In the present study, we investigated the biotransformation of 6-gingerol in different cancer cells and in mice, purified and identified the major metabolites from human lung cancer cells, and determined the effects of the major metabolites on the proliferation of human cancer cells. Our results show that 6-gingerol is extensively metabolized in H-1299 human lung cancer cells, CL-13 mouse lung cancer cells, HCT-116 and HT-29 human colon cancer cells, and in mice. The two major metabolites in H-1299 cells were purified and identified as (3R,5S)-6-gingerdiol (M1) and (3S,5S)-6-gingerdiol (M2) based on the analysis of their 1D and 2D NMR data. Both metabolites induced cytotoxicity in cancer cells after 24 h, with M1 having a comparable effect to 6-gingerol in H-1299 cells.
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http://dx.doi.org/10.1021/jf303879bDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3649839PMC
November 2012

Ginger stimulates hematopoiesis via Bmp pathway in zebrafish.

PLoS One 2012 25;7(6):e39327. Epub 2012 Jun 25.

The Biomedical/Biotechnology Research Institute, North Carolina Central University, North Carolina Research Campus, Kannapolis, North Carolina, United States of America.

Background: Anemia is a hematologic disorder with decreased number of erythrocytes. Erythropoiesis, the process by which red blood cells differentiate, are conserved in humans, mice and zebrafish. The only known agents available to treat pathological anemia are erythropoietin and its biologic derivatives. However, erythropoietin therapy elicits unwanted side-effects, high cost and intravenous or subcutaneous injection, warranting the development of a more cost effective and non-peptide alternative. Ginger (Zingiber officinale) has been widely used in traditional medicine; however, to date there is no scientific research documenting the potential of ginger to stimulate hematopoiesis.

Methodology/principal Findings: Here, we utilized gata1:dsRed transgenic zebrafish embryos to investigate the effect of ginger extract on hematopoiesis in vivo and we identified its bioactive component, 10-gingerol. We confirmed that ginger and 10-gingerol promote the expression of gata1 in erythroid cells and increase the expression of hematopoietic progenitor markers cmyb and scl. We also demonstrated that ginger and 10-gingerol can promote the hematopoietic recovery from acute hemolytic anemia in zebrafish, by quantifying the number of circulating erythroid cells in the dorsal aorta using video microscopy. We found that ginger and 10-gingerol treatment during gastrulation results in an increase of bmp2b and bmp7a expression, and their downstream effectors, gata2 and eve1. At later stages ginger and 10-gingerol can induce bmp2b/7a, cmyb, scl and lmo2 expression in the caudal hematopoietic tissue area. We further confirmed that Bmp/Smad pathway mediates this hematopoiesis promoting effect of ginger by using the Bmp-activated Bmp type I receptor kinase inhibitors dorsomorphin, LND193189 and DMH1.

Conclusions/significance: Our study provides a strong foundation to further evaluate the molecular mechanism of ginger and its bioactive components during hematopoiesis and to investigate their effects in adults. Our results will provide the basis for future research into the effect of ginger during mammalian hematopoiesis to develop novel erythropoiesis promoting agents.
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http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0039327PLOS
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3382625PMC
March 2013

Protective effects of lotus (Nelumbo nucifera Gaertn) germ oil against carbon tetrachloride-induced injury in mice and cultured PC-12 cells.

Food Chem Toxicol 2012 May 3;50(5):1447-53. Epub 2012 Feb 3.

Department of Food Science and Technology, Ginling College, Nanjing Normal University, 122# Ninghai Road, Nanjing 210097, PR China.

The protective effects of lotus germ oil on liver and kidney damage by carbon tetrachloride-induced chronic hepatotoxicity in mice, PC-12 cells, and DNA damage were investigated. The mice were treated orally with lotus germ oil or dl-α-tocopherol after administration CCl(4) for 49 consecutive days. The levels of key antioxidant enzymes, such as superoxide dismutase (SOD), catalase (CAT), and the concentration of glutathione (GSH), as well as the concentration of malondialdehyde (MDA), an indicator of lipid peroxidation, were determined in homogenates of the liver and the kidney. The pathological histology of the liver was also examined. The activities of SOD, CAT, and the concentration of GSH were increased significantly (p<0.05-0.01) after treated with lotus germ oil in a concentration-dependent manner. Whereas, the content of the peroxidation product MDA were decreased significantly (p<0.05), similar to the serum levels of hepatic enzyme biomarkers (alanine aminotransferase and aspartate aminotransferase). Furthermore, lotus germ oil could inhibit the conversion of super-coiled pBR322 plasmid DNA to the open circular form and apoptosis of hydrogen peroxide-induced PC-12 cells. The result of this study suggested that the lotus germ oil could be recognized as powerful "functional oil" against oxidative stress.
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http://dx.doi.org/10.1016/j.fct.2012.01.037DOI Listing
May 2012

Metabolism of [6]-shogaol in mice and in cancer cells.

Drug Metab Dispos 2012 Apr 13;40(4):742-53. Epub 2012 Jan 13.

Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University, North Carolina Research Campus, 500 Laureate Way, Kannapolis, NC 28081, USA.

Ginger has received extensive attention because of its antioxidant, anti-inflammatory, and antitumor activities. However, the metabolic fate of its major components is still unclear. In the present study, the metabolism of [6]-shogaol, one of the major active components in ginger, was examined for the first time in mice and in cancer cells. Thirteen metabolites were detected and identified, seven of which were purified from fecal samples collected from [6]-shogaol-treated mice. Their structures were elucidated as 1-(4'-hydroxy-3'-methoxyphenyl)-4-decen-3-ol (M6), 5-methoxy-1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-one (M7), 3',4'-dihydroxyphenyl-decan-3-one (M8), 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-ol (M9), 5-methylthio-1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-one (M10), 1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-one (M11), and 5-methylthio-1-(4'-hydroxy-3'-methoxyphenyl)-decan-3-ol (M12) on the basis of detailed analysis of their (1)H, (13)C, and two-dimensional NMR data. The rest of the metabolites were identified as 5-cysteinyl-M6 (M1), 5-cysteinyl-[6]-shogaol (M2), 5-cysteinylglycinyl-M6 (M3), 5-N-acetylcysteinyl-M6 (M4), 5-N-acetylcysteinyl-[6]-shogaol (M5), and 5-glutathiol-[6]-shogaol (M13) by analysis of the MS(n) (n = 1-3) spectra and comparison to authentic standards. Among the metabolites, M1 through M5, M10, M12, and M13 were identified as the thiol conjugates of [6]-shogaol and its metabolite M6. M9 and M11 were identified as the major metabolites in four different cancer cell lines (HCT-116, HT-29, H-1299, and CL-13), and M13 was detected as a major metabolite in HCT-116 human colon cancer cells. We further showed that M9 and M11 are bioactive compounds that can inhibit cancer cell growth and induce apoptosis in human cancer cells. Our results suggest that 1) [6]-shogaol is extensively metabolized in these two models, 2) its metabolites are bioactive compounds, and 3) the mercapturic acid pathway is one of the major biotransformation pathways of [6]-shogaol.
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http://dx.doi.org/10.1124/dmd.111.043331DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3310425PMC
April 2012

Chemical components of the roots of Noni (Morinda citrifolia) and their cytotoxic effects.

Fitoterapia 2011 Jun 25;82(4):704-8. Epub 2011 Feb 25.

Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University, North Carolina Research Campus, 500 Laureate Way, Kannapolis, NC 28081, USA.

Roots of Morinda citrifolia (Noni or Yor in Thai) have been used traditionally for thousands of years to treat chronic diseases such as cancer and heart disease. In this study, three new anthraquinones together with 15 known compounds were isolated from the roots of M. citrifolia (Rubiaceae). Their structures were established by spectroscopic methods, particularly 1D and 2D NMR techniques. Six known compounds, together with two new compounds (2 and 3) showed significant inhibitory effects on the proliferation of human lung and colon cancer cells.
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http://dx.doi.org/10.1016/j.fitote.2011.02.008DOI Listing
June 2011

Genistein inhibits advanced glycation end product formation by trapping methylglyoxal.

Chem Res Toxicol 2011 Apr 23;24(4):579-86. Epub 2011 Feb 23.

Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University, North Carolina Research Campus, 500 Laureate Way, Kannapolis, NC 28081, United States.

Methylglyoxal (MGO) is a highly reactive endogenous metabolite derived from several nonenzymatic and enzymatic reactions, and identified as a well-known precursor of advanced glycation end products (AGEs). In the present study, genistein, a naturally occurring isoflavone derived from soy products, demonstrated significant trapping effects of MGO and consequently formed mono- and di-MGO adducts under physiological conditions (pH 7.4, 37 °C). More than 80.0% of MGO was trapped within 4 h, and the trapping efficiency could be up to 97.7% at 24 h. The reaction adducts formed from genistein and MGO under different ratios were analyzed using LC/MS. We also successfully purified and identified the major mono- and di-MGO conjugated adducts of genistein. The NMR data showed that positions 6 and 8 of the A ring of genistein were the major active sites for trapping MGO. We further demonstrated that genistein could effectively inhibit the formation of AGEs in the human serum albumin (HSA)-MGO assay. Two mono-MGO adducts and one di-MGO adduct of genistein were detected in this assay using LC/MS. The di-MGO adduct of genistein became the dominant reaction product during prolonged incubation. Results from this study, as well as our previous findings on (-)-epigallocatechin 3-gallate (EGCG), phloridzin and phloretin, indicate that dietary flavonoids that have the same A ring structure as genistein, EGCG, phloridzin, and phloretin may have the potential to inhibit the formation of AGEs by trapping reactive dicarbonyl species.
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http://dx.doi.org/10.1021/tx100457hDOI Listing
April 2011

Quantitative analysis of ginger components in commercial products using liquid chromatography with electrochemical array detection.

J Agric Food Chem 2010 Dec 23;58(24):12608-14. Epub 2010 Nov 23.

Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University, North Carolina Research Campus, 500 Laureate Way, Kannapolis, North Carolina 28081, United States.

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.
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http://dx.doi.org/10.1021/jf1029256DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3446752PMC
December 2010

Stilbene glucoside from Polygonum multiflorum Thunb.: a novel natural inhibitor of advanced glycation end product formation by trapping of methylglyoxal.

J Agric Food Chem 2010 Feb;58(4):2239-45

Department of Food Science and Technology, Ginling College, Nanjing Normal University, 122 Ninghai Road, Nanjing 210097, People's Republic of China.

Methylglyoxal (MGO), the reactive dicarbonyl intermediate generated during the nonenzymatic glycation between reducing sugars and amino groups of proteins, lipids, and DNA, is the precursor of advanced glycation end products (AGEs). Many studies have shown that AGEs play a major pathogenic role in diabetes and its complications. This study found that 2,3,5,4'-tetrahydroxystilbene 2-O-beta-D-glucoside (THSG), the major bioactive compound from Polygonum multiflorum Thunb., can efficiently inhibit the formation of AGEs in a dose-dependent manner by trapping reactive MGO under physiological conditions (pH 7.4, 37 degrees C). More than 60% MGO was trapped by THSG within 24 h, which was much more effective than resveratrol and its methylated derivative, pterostilbene, the two major bioactive dietary stilbenes. The major mono- and di-MGO adducts of THSG were successfully purified and found to be mixtures of tautomers. LC-MS and NMR data showed that positions 4 and 6 of the A ring were the major active sites for trapping MGO. It was also found that THSG could significantly inhibit the formation of AGEs in the human serum albumin (HSA)-MGO assay and both mono- and di-MGO adducts of THSG were detected in this assay using LC-MS. The results suggest that the ability of THSG to trap reactive dicarbonyl species makes it a potential natural inhibitor of AGEs.
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http://dx.doi.org/10.1021/jf904122qDOI Listing
February 2010