Journal of Food and Nutrition Research
ISSN (Print): 2333-1119 ISSN (Online): 2333-1240 Website: Editor-in-chief: Prabhat Kumar Mandal
Open Access
Journal Browser
Journal of Food and Nutrition Research. 2014, 2(3), 101-108
DOI: 10.12691/jfnr-2-3-2
Open AccessArticle

Identification of the Oxidative Products and Ozonolysis Pathways of Polyphenols in Peanut Skins

Enjie Diao1, Xiangzhen Shen1, Zheng Zhang1, Ning Ji1, Wenwen Ma1 and Haizhou Dong1,

1College of Food Science and Engineering, Shandong Agricultural university, Taian, People’ Republic of China

Pub. Date: March 22, 2014

Cite this paper:
Enjie Diao, Xiangzhen Shen, Zheng Zhang, Ning Ji, Wenwen Ma and Haizhou Dong. Identification of the Oxidative Products and Ozonolysis Pathways of Polyphenols in Peanut Skins. Journal of Food and Nutrition Research. 2014; 2(3):101-108. doi: 10.12691/jfnr-2-3-2


Many studies have proved that ozone can decompose aflatoxins in peanuts, while polyphenols in peanut skins can also be destroyed due to its strong oxidative capacity. The polyphenols and their oxidative products in the peanut skin extracts at different ozonated times were separated and identified by HPLC-Q-TOF/MS. Based on the accurate molecular weight from mass spectrogram, and consulted the reported literatures, nine polyphenols and nine main oxidative products were identified in the peanut skins. According to the oxidative mechanism of phenols and the Criegee mechanism of ozonolysis, the ozonolysis pathways of nine polyphenols were proposed. The structures of oxidative products showed that ozone can destroy the polyphenols, so the effects of ozone treatment on the peanut skins should be considered by processors in the detoxification of aflatoxin-contaminated peanuts.

polyphenols ozone oxidative product criegee mechanism peanut skin

Creative CommonsThis work is licensed under a Creative Commons Attribution 4.0 International License. To view a copy of this license, visit


Figure of 6


[1]  Yu JM., Mohamed A., Ipek G., “Effects of processing methods and extraction solvents on concentration and antioxidant activity of peanut skin phenolics,” Food Chemistry, 90. 199-206. 2005.
[2]  Tiwari BK., O’Donnell CP., Muthukumarappan K., Cullen PJ., “Anthocyanins and color degradation in ozone treated blackberry juice,” Innovative Food Science and Emerging Technologies, 10. 70-75. 2009.
[3]  Yu J., Ahmedna M., Goktepe I., “Potential of peanut skin phenolic extract as antioxidative and antibacterial agent in cooked and raw ground beef,” International Journal of Food Science and Technology, 45.1337-1344. 2010.
[4]  Jackman RL., Yada RY., Tung MA., Speers RA., “Anthocyanins as food colorants -a review,” Journal of Food Biochemistry, 11. 201-247. 1987.
[5]  Rein MJ., Heinonen M., “Stability and enhancement of berry juice color,” Journal of Agricultural and Food Chemistry, 52. 3106-3114. 2004.
[6]  Williams JH., Phillips TD., Jolly PE., Stiles JK., Jolly CM., Aggarwal D., “Human aflatoxicosis in developing countries: a review of toxicology, exposure, potential health consequences, and interventions,” The American Journal of Clinical Nutrition, 80. 1106-1122. 2004.
[7]  Netke SP., Roomi MW., Tsao C, Niedwiecki A., “Ascorbic acid protects Guinea pigs from acute aflatoxin toxicity,” Toxicology and Applied Pharmacology, 143. 429-435. 1997.
[8]  Das C., Mishra HN., “Effect of aflatoxin B1 detoxification on the physicochemical properties and quality of ground nut meal,” Food Chemistry, 70. 483-487. 2000.
[9]  Haskard C., Binnion C., Ahokas J., “Factors affecting the sequestration of aflatoxin by Lactobacillus rhamnosus strain GG,” Chemico-Biological Interactions, 128. 39-49. 2000.
[10]  McKenzie KS., Sarr AB., Mayura K., Bailey RH., Miller DR., Rogers TD., Norred WP., Voss KA., Plattner RD., Kubena LF., Phillips TD., “Oxidative degradation and detoxification of mycotoxins using a novel source of ozone,” Food Chemistry and Toxicology, 35. 807-820. 1997.
[11]  Akbas MY., Ozdemir M., “Effect of different ozone treatments on aflatoxin degradation and physicochemical properties of pistachios,” Journal of the Science of Food and Agriculture, 86. 2099-2104. 2006.
[12]  Zorlugenç B., Zorlugenç FK., Öztekin S., Evliya IB., “The influence of gaseous ozone and ozonated water on microbial flora and degradation of aflatoxin B dried figs,” Food Chemistry and Toxicology, 46. 3593-3597. 2008.
[13]  Guzel-Seydim Z., Greene AK., Wolososhuk CP., “Use of ozone in the food industry,” Lebensmittel-Wissenschaft & Technologie, 37. 453-460. 2004.
[14]  Alencar ER., Faroni LRD., Soares NFF., Carvalho MCS., Pereira KF., “Effect of the ozonization process on the quality of peanuts and crude oil,” Reviata Brasileira de Engenharia Agrĺcola Ambiental, 15. 154-160. 2011.
[15]  Diao EJ., Shan CP., Hou HX., Wang SS., Li MH., Dong HZ., “Structures of the Ozonolysis Products and Ozonolysis Pathway of Aflatoxin B Acetonitrile Solution,” Journal of Agricultural and Food Chemistry, 60. 9364-9370. 2012.
[16]  Mortishire-Smith RJ., O’Connor D., Castro-Perez JM., Kirby J., “Accelerated throughput metabolic route screening in early drug discovery using high-resolution liquid chromatography/quadrupole time-of-flight mass spectrometry and automated data analysis,” Rapid Communications in Mass Spectrometry, 19. 2659-2670. 2005.
[17]  Bateman KP., Castro-Perez J., Wrona M., Shockor JP., Yu K., Oballa R., Nicoll-Griffith DA., “MSE with mass defect filtering for in vitro and in vivo metabolite identification,” Rapid Communications in Mass Spectrometry, 21. 1485-1496. 2007.
[18]  Lin ZS., Le J., Hong ZY., “Liquid chromatography-quadrupole-time-of-flight mass spectrometry and its application in the metabolism (metabolomics) research of traditional Chinese medicines,” Chinese Pharmaceutical Journal, 47. 401-405. 2012.
[19]  Qiu JY., Chen LL., Zhu QJ., Wang DJ., Wang WL., Sun X., Liu XY., Du FL., “Screening natural antioxidants in peanut shell using DPPH-HPLC-DAD-TOF/MS methods,” Food Chemistry, 135. 2366-2371. 2012.
[20]  Appeldoorn MM., Sanders M., Vincken JP., Cheynier V., Guernevé CL., Hollman PCH., Gruppen H., “Efficient isolation of major procyanidin A-type dimers from peanut skins and B-type dimers from grape seeds,” Food Chemistry, 117. 713-720. 2009.
[21]  Palafox-Carlos H., Yahia EM., González-Aguilar GA., “Identification and quantification of major phenolic compounds from mango (Mangifera indica, cv. Ataulfo) fruit by HPLC-DAD-MS/MS-ESI and their individual contribution to the antioxidant activity during ripening,” Food Chemistry, 135.105-111. 2012.
[22]  Sarnoski PJ., Johnson JV., Reed KA., Tanko JM., O’Keefe SF., “Separation and characterisation of proanthocyanidins in Virginia type peanut skins by LC-MSn,” Food Chemistry, 131. 927-939. 2012.
[23]  Reed KA., “Identification of phenolic compounds from peanut skin using HPLC-MSn,” Doctoral Dissertation, Virginia Polytechnic Institute and State University, USA. p 195-295. 2009.
[24]  Lazarus SA., Adamson GE., Hammerstone JF., Schmitz HH., “High-performance liquid chromatography/mass spectrometry analysis of proanthocyanidins in foods and beverages,” Journal of Agricultural and Food Chemistry, 47. 3693-3701. 1999.
[25]  Lou HX., Yamazaki Y., Sasaki T., Uchida M., Tanaka H., Oka S., “A-type proanthocyanidins from peanut skins,” Phytochemistry, 51. 297-308. 1999.
[26]  Lou HX., Yuan HQ., Ma B., Ren DM., Ji M., Oka S., “Polyphenols from peanut skins and their free radical-scavenging effects,” Phytochemistry, 65. 2391-2399. 2004.
[27]  Talcott ST., Passeretti S., Duncan CE., Gorbet DW., “Polyphenolic content and sensory properties of normal and high oleic acid peanuts,” Food Chemistry, 90. 379-388. 2005.
[28]  Lee SC., Jeong SM., Kim SY., Park HR., Nam KC., Ahn DU., “Effect of far-infrared radiation and heat treatment on the antioxidant activity of water extracts from peanut hulls,” Food Chemistry, 94. 489-493. 2006.
[29]  Davis JP., Dean LL., Price KM., Sanders TH., “Roast effects on the hydrophilic and lipophilic antioxidant capacities of peanut flours, blanched peanut seed and peanut skins,” Food Chemistry, 119. 539-547. 2010.
[30]  de Camargo AC., de Souza Vieira TM., Regitano-D’Arce FMA., Calori-Domingues BMA., Canniatti-Brazaca SG., “Gamma radiation effects on peanut skin antioxidants,” International Journal of Molecular Science, 13. 3073-3084. 2012.
[31]  Huang HN., Hu XH., Huang HQ., Yan L., Chen DS., Ou-yang GL., Zhuo HQ., “Polymer characteristics of catechin and catechin-Ge4+ measured with a technology of mass spectrometry,” Chinese Journal of Analytical Chemistry, 1. 52-56. 2006.
[32]  Devlin HR., Harris IJ., “Mechanism of the oxidation of aqueous phenol with dissolved oxygen,” Industrial and Engineering Chemistry Fundamentals, 23. 387-392. 1984.
[33]  Eftaxias A., Font J., Fortuny A., Giralt J., Fabregat A., Stüber F., “Kinetic modelling of catalytic wet air oxidation of phenol by simulated annealing,” Applied Catalysis B: Environmental, 33. 175-190. 2001.
[34]  Portela Miguélez JR., López Bemal J., Nebot Sanz E., Martínez de la Ossa E., “Kinetics of wet air oxidation of phenol,” Chemical Engineering Journal, 67.115-121. 1997.
[35]  Criegee R., “Mechanism of ozonolysis,” Angewandte Chemie International Edition in English, 14. 745-752. 1975.
[36]  Millican RC., “A thiobarbituric acid assay for shikimic acid,” Analytical Biochemistry, 6. 181-192. 1963.