Antioxidative Activity of Heterocyclic Compounds Found in Coffee Volatiles Produced by Maillard Reaction
Abstract
Typical heterocyclic compounds substituted with various functional groups found in Maillard reaction products were examined for antioxidant activity. Pyrroles exhibited the greatest antioxidant activity among all heterocyclic compounds tested. All pyrroles inhibited hexanal oxidation by almost 100% at a concentration of 50 μg/mL over 40 days. Addition of formyl and acetyl groups to a pyrrole ring enhanced antioxidative activity remarkably. Pyrrole-2-carboxaldehyde, 2-acetylpyrrole, 1-methyl-2-pyrrolecarboxaldehyde, and 2-acetyl-1-methylpyrrole inhibited hexanal oxidation by >80% at 10 μg/mL. Unsubstituted furan exhibited the greatest antioxidant activity among furans tested. Addition of all functional groups used in this study to furan decreased antioxidative activity. The antioxidant activity of thiophene increased with the addition of methyl and ethyl groups, but the addition of formyl or acetyl groups to thiophene decreased antioxidant activity. Thiazoles and pyrazines were ineffective antioxidants at all concentrations tested. Reaction of all heterocyclic compounds with hydrogen peroxide resulted in the formation of various oxidized products.
Keywords: Antioxidants; heterocyclic compounds; pyrroles; furans; thiophenes
†
Japan Institute for the Control of Aging.
‡
University of California.
*
Author to whom correspondence should be addressed [telephone (530) 752-4523; fax (530) 752-3394; e-mail [email protected]].
Cited By
This article is cited by 195 publications.
- Muyao Xi, Agnes A. M. Berendsen, Madeleine Ernst, Tu Hu, Natalia Vázquez-Manjarrez, Edith J. M. Feskens, Lars Ove Dragsted, Giorgia La Barbera. Combined Urinary Biomarkers to Assess Coffee Intake Using Untargeted Metabolomics: Discovery in Three Pilot Human Intervention Studies and Validation in Cross-Sectional Studies. Journal of Agricultural and Food Chemistry 2021, 69 (25) , 7230-7242. https://doi.org/10.1021/acs.jafc.1c01155
- Clemens Kanzler, Paul T. Haase, Helena Schestkowa, and Lothar W. Kroh . Antioxidant Properties of Heterocyclic Intermediates of the Maillard Reaction and Structurally Related Compounds. Journal of Agricultural and Food Chemistry 2016, 64 (41) , 7829-7837. https://doi.org/10.1021/acs.jafc.6b03398
- Masumi Kamiyama, Joon-Kwan Moon, Hae Won Jang, and Takayuki Shibamoto . Role of Degradation Products of Chlorogenic Acid in the Antioxidant Activity of Roasted Coffee. Journal of Agricultural and Food Chemistry 2015, 63 (7) , 1996-2005. https://doi.org/10.1021/jf5060563
- Bagher Eftekhari-Sis, Maryam Zirak, and Ali Akbari . Arylglyoxals in Synthesis of Heterocyclic Compounds. Chemical Reviews 2013, 113 (5) , 2958-3043. https://doi.org/10.1021/cr300176g
- Sanghae Nam, Hae Won Jang, and Takayuki Shibamoto . Antioxidant Activities of Extracts from Teas Prepared from Medicinal Plants, Morus alba L., Camellia sinensis L., and Cudrania tricuspidata, and Their Volatile Components. Journal of Agricultural and Food Chemistry 2012, 60 (36) , 9097-9105. https://doi.org/10.1021/jf301800x
- Ana Filipa L. O. M. Santos and Manuel A. V. Ribeiro da Silva . A Combined Experimental and Computational Thermodynamic Study of the Isomers of Pyrrolecarboxaldehyde and 1-Methyl- pyrrolecarboxaldehyde. The Journal of Physical Chemistry B 2011, 115 (43) , 12549-12557. https://doi.org/10.1021/jp2068057
- Mónica Pérez-Martínez, Bettina Caemmerer, M. Paz De Peña, Concepción Cid and Lothar W. Kroh . Influence of Brewing Method and Acidity Regulators on the Antioxidant Capacity of Coffee Brews. Journal of Agricultural and Food Chemistry 2010, 58 (5) , 2958-2965. https://doi.org/10.1021/jf9037375
- Joon-Kwan Moon, Hyui Sun Yoo and Takayuki Shibamoto. Role of Roasting Conditions in the Level of Chlorogenic Acid Content in Coffee Beans: Correlation with Coffee Acidity. Journal of Agricultural and Food Chemistry 2009, 57 (12) , 5365-5369. https://doi.org/10.1021/jf900012b
- Ana Filipa L. O. M. Santos, José R. B. Gomes and Manuel A. V. Ribeiro da Silva . 2- and 3-Acetylpyrroles: A Combined Calorimetric and Computational Study. The Journal of Physical Chemistry A 2009, 113 (15) , 3630-3638. https://doi.org/10.1021/jp810407m
- I. Rodríguez-Meizoso, L. Jaime, S. Santoyo, A. Cifuentes, G. García-Blairsy Reina, F. J. Señoráns and E. Ibáñez. Pressurized Fluid Extraction of Bioactive Compounds from Phormidium Species. Journal of Agricultural and Food Chemistry 2008, 56 (10) , 3517-3523. https://doi.org/10.1021/jf703719p
- Justin Koffi Houessou, Saber Maloug, Anne-Sophie Leveque, Corine Delteil, Bertrand Heyd and Valérie Camel. Effect of Roasting Conditions on the Polycyclic Aromatic Hydrocarbon Content in Ground Arabica Coffee and Coffee Brew. Journal of Agricultural and Food Chemistry 2007, 55 (23) , 9719-9726. https://doi.org/10.1021/jf071745s
- Rahi Golani, Chinglen Leishangthem, Hongwei Xiao, Qi Zhang, P.P. Sutar. Effect of high temperature short time infrared roasting of peanuts. Journal of Future Foods 2024, 4 (2) , 173-178. https://doi.org/10.1016/j.jfutfo.2023.06.009
- Tomoyuki Narisawa, Koichiro Sakai, Hideo Nakajima, Marie Umino, Haruyuki Yamashita, Kenjiro Sugiyama, Chikako Kiribuchi-Otobe, Kiwamu Shiiba, Masaharu Yamada, Tomiko Asakura. Effects of fatty acid hydroperoxides produced by lipoxygenase in wheat cultivars during dough preparation on volatile compound formation. Food Chemistry 2024, 443 , 138566. https://doi.org/10.1016/j.foodchem.2024.138566
- Fahad Hussain, Ayesha Tahir, Muhammad Saeed Jan, Noor Fatima, Abdul Sadiq, Umer Rashid. Exploitation of the multitarget role of new ferulic and gallic acid derivatives in oxidative stress-related Alzheimer's disease therapies: design, synthesis and bioevaluation. RSC Advances 2024, 14 (15) , 10304-10321. https://doi.org/10.1039/D4RA00766B
- Habi Salim, Cherrak Sabri Ahmed, Mokhtari–Soulimane Nassima, Bekhti Sari Fadia, Souna Mimoun, Hafida Merzouk. Coffee silverskin waste as alternative to produce alkaloids with antioxidant, antihemolytic, and alpha-amylase inhibitory activities. Biomass Conversion and Biorefinery 2023, 129 https://doi.org/10.1007/s13399-023-05207-4
- Heba M. Metwally, Norhan A. Khalaf, Ehab Abdel-Latif, Mohamed A. Ismail. Synthesis, DFT investigations, antioxidant, antibacterial activity and SAR-study of novel thiophene-2-carboxamide derivatives. BMC Chemistry 2023, 17 (1) https://doi.org/10.1186/s13065-023-00917-2
- Man Wang, Yanshi Jiang, Siying Wang, Lin Fu, Zujin Liang, Ying Zhang, Xiaodan Huang, Xin Li, Meiying Feng, Danfeng Long. Yak milk protects against alcohol-induced liver injury in rats. Food & Function 2023, 14 (21) , 9857-9871. https://doi.org/10.1039/D3FO03675H
- Si Young Ha, Ji Young Jung, Hyeon Cheol Kim, Jae-Kyung Yang, . Optimizing the Fermentation Conditions of Cudrania tricuspidata Fruit Using Bacillus amyloliquefaciens for Anti-Inflammatory Activity and GC-MS-Based Volatile Component Characteristics. Evidence-Based Complementary and Alternative Medicine 2023, 2023 , 1-13. https://doi.org/10.1155/2023/5042416
- Lodsna Borkotoky, Ram Awatar Maurya. Practical Synthesis of Pharmaceutically Relevant Pyrroles from α , β ‐Unsaturated Aldehydes and Phenacyl Azides. European Journal of Organic Chemistry 2023, 26 (39) https://doi.org/10.1002/ejoc.202300822
- Archana Kumari, Rajesh Kumar Singh. Synthesis, Drug-Likeness Evaluation of Some Heterocyclic Moieties Fused Indole Derivatives as Potential Antioxidants. Combinatorial Chemistry & High Throughput Screening 2023, 26 (11) , 2077-2084. https://doi.org/10.2174/1386207326666230102111810
- Ruifang Yang, Jianhao Tang, Qi Zhao, Zhongze Piao, Gangseob Lee, Changzhao Wan, Jianjiang Bai. Starch Properties of Roasting Rice from Naturally High-Resistant Starch Rice Varieties. Molecules 2023, 28 (17) , 6408. https://doi.org/10.3390/molecules28176408
- Jingmin Cui, Yan Sun, Linqing Wang, Wenqiang Tan, Zhanyong Guo. Preparation of chitosan derivatives containing aromatic five-membered heterocycles for efficient antimicrobial and antioxidant activities. International Journal of Biological Macromolecules 2023, 247 , 125850. https://doi.org/10.1016/j.ijbiomac.2023.125850
- Abdul Rehman Sadiq Butt, Muhammad Athar Abbasi, Aziz-ur-Rehman, Sabahat Zahra Siddiqui, Shabbir Muhammad, Hussain Raza, Syed Adnan Ali Shah, Muhammad Shahid, Abdullah G. Alsehemi, Song Ja Kim. Convergent synthesis, kinetics insight and allosteric computational ascriptions of thiazole-(5-aryl)oxadiazole hybrids embraced with propanamides as alkaline phosphatase inhibitors. RSC Advances 2023, 13 (20) , 13798-13808. https://doi.org/10.1039/D3RA01348K
- Xiaotong Cao, Hanjing Wu, Claudia G. Viejo, Frank R. Dunshea, Hafiz A. R. Suleria. Effects of postharvest processing on aroma formation in roasted coffee – a review. International Journal of Food Science & Technology 2023, 58 (3) , 1007-1027. https://doi.org/10.1111/ijfs.16261
- Gulsun Akdemir Evrendilek. Application of antioxidants in beverages. 2023, 199-216. https://doi.org/10.1016/B978-0-323-85683-6.00016-8
- Anna R. Ziefuß, Tim Hupfeld, Sven W. Meckelmann, Martin Meyer, Oliver J. Schmitz, Wiebke Kaziur-Cegla, Lucie K. Tintrop, Torsten C. Schmidt, Bilal Gökce, Stephan Barcikowski. Ultrafast cold-brewing of coffee by picosecond-pulsed laser extraction. npj Science of Food 2022, 6 (1) https://doi.org/10.1038/s41538-022-00134-6
- Min-Gyun Kang, Fazlurrahman Khan, Du-Min Jo, DoKyung Oh, Nazia Tabassum, Young-Mog Kim. Antibiofilm and Antivirulence Activities of Gold and Zinc Oxide Nanoparticles Synthesized from Kimchi-Isolated Leuconostoc sp. Strain C2. Antibiotics 2022, 11 (11) , 1524. https://doi.org/10.3390/antibiotics11111524
- Ashbala Shakoor, Chenping Zhang, Jianchun Xie, Xuelian Yang. Maillard reaction chemistry in formation of critical intermediates and flavour compounds and their antioxidant properties. Food Chemistry 2022, 393 , 133416. https://doi.org/10.1016/j.foodchem.2022.133416
- Manuela Giordano, Marta Bertolino, Simona Belviso, Daniela Ghirardello, Giuseppe Zeppa. Effects of Species, Post-Harvest Treatment, and Roasting on Fibre, Volatile Compounds, and Polyphenol Contents in Coffee Silverskin. Foods 2022, 11 (19) , 3132. https://doi.org/10.3390/foods11193132
- Manikandan Arumugam, Dinesh Babu Manikandan, Arun Sridhar, Sivagaami Palaniyappan, Sudharshini Jayaraman, Thirumurugan Ramasamy. GC–MS Based Metabolomics Strategy for Cost-Effective Valorization of Agricultural Waste: Groundnut Shell Extracts and Their Biological Inhibitory Potential. Waste and Biomass Valorization 2022, 13 (10) , 4179-4209. https://doi.org/10.1007/s12649-022-01768-z
- Hui-Ju Liu, Mingchih Fang. Characterization of aroma active volatile components in roasted mullet roe. Food Chemistry 2022, 385 , 132736. https://doi.org/10.1016/j.foodchem.2022.132736
- Silpa Kunnappilly Paulose, Kajal Chakraborty. Oxaspiro Indiculides from Old Woman Octopus Cistopus indicus as Dual Inhibitors of Inducible Cyclooxygenase and Lipoxygenase. Chemistry & Biodiversity 2022, 19 (7) https://doi.org/10.1002/cbdv.202200277
- Bubun Banerjee, Anu Priya, Aditi Sharma, Gurpreet Kaur, Manmeet Kaur. Sulfonated β-cyclodextrins: efficient supramolecular organocatalysts for diverse organic transformations. Physical Sciences Reviews 2022, 7 (4-5) , 539-565. https://doi.org/10.1515/psr-2021-0080
- Xiaomei Wang, Xiaogang Xu, Genxiang Mao, Yue Guo, Guangce Wang, Xue Sun, Nianjun Xu, Zhongshan Zhang. Structural Characterization of Gracilariopsis lemaneiformis Polysaccharide and Its Property in Delaying Cellular Senescence. Frontiers in Nutrition 2022, 9 https://doi.org/10.3389/fnut.2022.876992
- Qingru Xiang, Tao Feng, Qiang Su, Lingyun Yao, . Response Surface Methodology for Optimization of L-Arabinose/Glycine Maillard Reaction through Microwave Heating. Journal of Food Quality 2022, 2022 , 1-10. https://doi.org/10.1155/2022/1535296
- Xiao Jia, Lingcheng Li, JianWen Teng, Mingjie Li, Hui Long, Ning Xia. Glycation of rice protein and d-xylose pretreated through hydrothermal cooking-assisted high hydrostatic pressure: Focus on the structural and functional properties. LWT 2022, 160 , 113194. https://doi.org/10.1016/j.lwt.2022.113194
- Damian Maksimowski, Natalia Pachura, Maciej Oziembłowski, Agnieszka Nawirska-Olszańska, Antoni Szumny. Coffee Roasting and Extraction as a Factor in Cold Brew Coffee Quality. Applied Sciences 2022, 12 (5) , 2582. https://doi.org/10.3390/app12052582
- Sraa Abu-Melha. Molecular modeling and antioxidant activity of newly synthesized 3‑hydroxy-2-substituted-thiophene derivatives. Journal of Molecular Structure 2022, 1250 , 131821. https://doi.org/10.1016/j.molstruc.2021.131821
- Shiyu Huang, Gangliang Huang. Extraction, structural analysis, and activities of rice bran polysaccharide. Chemical Biology & Drug Design 2021, 98 (4) , 631-638. https://doi.org/10.1111/cbdd.13916
- Sibel Yalçın, Merve Uzun, Özge Karakaş, Kevser Sözgen Başkan, Emine Şükran Okudan, Mustafa Reşat Apak. Determination of Total Antioxidant Capacities of Algal Pigments in Seaweed by the Combination of High-Performance Liquid Chromatography (HPLC) with A Cupric Reducing Antioxidant Capacity (CUPRAC) Assay. Analytical Letters 2021, 54 (14) , 2239-2258. https://doi.org/10.1080/00032719.2020.1855439
- Hyun-Jin Kim, Jung-Ah Han, Seung-Taik Lim, Dong-Hwa Cho. Effects of germination and roasting on physicochemical and sensory characteristics of brown rice for tea infusion. Food Chemistry 2021, 350 , 129240. https://doi.org/10.1016/j.foodchem.2021.129240
- Enoch T. Quayson, George S. Ayernor, Paa-Nii T. Johnson, Fidelis C.K. Ocloo. Effects of two pre-treatments, blanching and soaking, as processing modulation on non-enzymatic browning developments in three yam cultivars from Ghana. Heliyon 2021, 7 (6) , e07224. https://doi.org/10.1016/j.heliyon.2021.e07224
- Farhan M. Khan, Muhammad A. Abbasi, Aziz‐ur‐Rehman, Sabahat Z. Siddiqui, Abdul R. Sadiq Butt, Hussain Raza, Ayesha Zafar, Syed A. Ali Shah, Muhammad Shahid, Sung‐Yum Seo. Convergent synthesis of carbonic anhydrase inhibiting bi‐heterocyclic benzamides: Structure–activity relationship and mechanistic explorations through enzyme inhibition, kinetics, and computational studies. Journal of Heterocyclic Chemistry 2021, 58 (5) , 1089-1103. https://doi.org/10.1002/jhet.4240
- Gert W. Meijer, Liisa Lähteenmäki, Richard H. Stadler, Jochen Weiss. Issues surrounding consumer trust and acceptance of existing and emerging food processing technologies. Critical Reviews in Food Science and Nutrition 2021, 61 (1) , 97-115. https://doi.org/10.1080/10408398.2020.1718597
- Yu Fu, Yuhao Zhang, Olugbenga P. Soladoye, Rotimi E. Aluko. Maillard reaction products derived from food protein-derived peptides: insights into flavor and bioactivity. Critical Reviews in Food Science and Nutrition 2020, 60 (20) , 3429-3442. https://doi.org/10.1080/10408398.2019.1691500
- Reem A. Alenzi, Nizar El Guesmi, Mohamed R. Shaaban, Basim H. Asghar, Thoraya A. Farghaly. Assessing the nucleophilic character of 2-amino-4-arylthiazoles through coupling with 4,6-dinitrobenzofuroxan: Experimental and theoretical approaches based on structure-reactivity relationships. Journal of Saudi Chemical Society 2020, 24 (10) , 754-764. https://doi.org/10.1016/j.jscs.2020.08.004
- Shaikha S. AlNeyadi, Naheed Amer, Tony G. Thomas, Ruba Al Ajeil, Priya Breitener, N Munawar. Synthesis, Characterization, and Antioxidant Activity of Some 2-Methoxyphenols derivatives. Heterocyclic Communications 2020, 26 (1) , 112-122. https://doi.org/10.1515/hc-2020-0112
- Xu Chen, Fei Fang, Shaoyun Wang. Physicochemical properties and hepatoprotective effects of glycated Snapper fish scale peptides conjugated with xylose via maillard reaction. Food and Chemical Toxicology 2020, 137 , 111115. https://doi.org/10.1016/j.fct.2020.111115
- M Rahardjo, M Sihombing, M K Anggraeni. Color development and antioxidant activity in honey caramel. IOP Conference Series: Earth and Environmental Science 2020, 443 (1) , 012041. https://doi.org/10.1088/1755-1315/443/1/012041
- Ola Lasekan, Li Shing Teoh. Contribution of aroma compounds to the antioxidant properties of roasted white yam (Dioscorea rotundata). BMC Chemistry 2019, 13 (1) https://doi.org/10.1186/s13065-019-0650-3
- Liu, Li, Luo. Effect of Carboxymethylation and Phosphorylation on the Properties of Polysaccharides from Sepia esculenta Ink: Antioxidation and Anticoagulation in Vitro. Marine Drugs 2019, 17 (11) , 626. https://doi.org/10.3390/md17110626
- Issaraporn JINAKOT, Wannee JIRAPAKKUL. Volatile Aroma Compounds in Jasmine Rice as Affected by Degrees of Milling. Journal of Nutritional Science and Vitaminology 2019, 65 (Supplement) , S231-S234. https://doi.org/10.3177/jnsv.65.S231
- Fang Chen, Gangliang Huang, Zhiyuan Yang, Yupeng Hou. Antioxidant activity of Momordica charantia polysaccharide and its derivatives. International Journal of Biological Macromolecules 2019, 138 , 673-680. https://doi.org/10.1016/j.ijbiomac.2019.07.129
- A. M. Bumander, I. I. Althagafi, M. R. Shaaban, T. A. Farghaly. Comparative Study Between Thermal Heating and Microwave-Assisted Synthesis for New Series of Phenothiazine Derivatives. Russian Journal of Organic Chemistry 2019, 55 (9) , 1407-1415. https://doi.org/10.1134/S1070428019090227
- Shiva Prasad Kollur, Joaquín Ortega Castro, Juan Frau, Norma Flores-Holgu´ın, Govindaraju Shruthi, Chandan Shivamallu, Daniel Glossman-Mitnik. Preparation, spectroscopic investigations and chemical reactivity properties of a new schiff base ligand and its copper (II) complexes. Journal of Molecular Structure 2019, 1191 , 17-23. https://doi.org/10.1016/j.molstruc.2019.03.101
- Maciej Roman Nowak, Rafał Zdunek, Edward Pliński, Piotr Świątek, Małgorzata Strzelecka, Wiesław Malinka, Stanisława Plińska. Recognition of Pharmacological Bi-Heterocyclic Compounds by Using Terahertz Time Domain Spectroscopy and Chemometrics. Sensors 2019, 19 (15) , 3349. https://doi.org/10.3390/s19153349
- Eun Jeong Park, Jun-Hyun Oh. Antimicrobial activities of Korean mugwort (Artemisia iwayomogi and Artemisia princeps) extracts against Staphylococcus aureus and Cutibacterium acnes. Korean Journal of Food Preservation 2019, 26 (4) , 381-390. https://doi.org/10.11002/kjfp.2019.26.4.381
- Birutė Grybaitė, Rita Vaickelionienė, Maryna Stasevych, Olena Komarovska‐Porokhnyavets, Kristina Kantminienė, Volodymyr Novikov, Vytautas Mickevičius. Synthesis and Antimicrobial Activity of Novel Thiazoles with Reactive Functional Groups. ChemistrySelect 2019, 4 (23) , 6965-6970. https://doi.org/10.1002/slct.201900679
- Cheng Fang, Hai Du, Xiaojiao Zheng, Aihua Zhao, Wei Jia, Yan Xu. Solid‐state fermented Chinese alcoholic beverage (baijiu) and ethanol resulted in distinct metabolic and microbiome responses. The FASEB Journal 2019, 33 (6) , 7274-7288. https://doi.org/10.1096/fj.201802306R
- Jinsu Kim, Gahyun Baek, Jaai Kim, Changsoo Lee. Energy production from different organic wastes by anaerobic co-digestion: Maximizing methane yield versus maximizing synergistic effect. Renewable Energy 2019, 136 , 683-690. https://doi.org/10.1016/j.renene.2019.01.046
- Zhenhua Duan, Weiwen Duan, Fangping Li, Yanqun Li, Ping Luo, Huazhong Liu. Effect of carboxymethylation on properties of fucoidan from Laminaria japonica: Antioxidant activity and preservative effect on strawberry during cold storage. Postharvest Biology and Technology 2019, 151 , 127-133. https://doi.org/10.1016/j.postharvbio.2019.02.008
- Manal M. Alsharekh, Ismail I. Althagafi, Mohamed R. Shaaban, Thoraya A. Farghaly. Microwave-assisted and thermal synthesis of nanosized thiazolyl-phenothiazine derivatives and their biological activities. Research on Chemical Intermediates 2019, 45 (2) , 127-154. https://doi.org/10.1007/s11164-018-3594-7
- Y. Umar, J. Tijani, S. Abdalla. Conformational Stabilities, Rotational Barriers, and Vibrational Spectra of 2-Pyrrolecarboxaldehyde and 3-Pyrrolecarboxaldehyde Calculated Using Density Functional Theory. Journal of Structural Chemistry 2019, 60 (2) , 186-197. https://doi.org/10.1134/S0022476619020033
- Yan Zhang, Jian Guo, Lu Cai, Yaning Wang, Lili Ji, Wendong Song. Antioxidant of Maillard products derived from squid skin with different reducing sugars. 2019, 020040. https://doi.org/10.1063/1.5110834
- Cheng Fang, Hai Du, Wei Jia, Yan Xu. Compositional Differences and Similarities between Typical Chinese Baijiu and Western Liquor as Revealed by Mass Spectrometry-Based Metabolomics. Metabolites 2019, 9 (1) , 2. https://doi.org/10.3390/metabo9010002
- Hang Yu, Yi-Xin Seow, Peter K. C. Ong, Weibiao Zhou. Effects of high-intensity ultrasound and oil type on the Maillard reaction of d-glucose and glycine in oil-in-water systems. npj Science of Food 2018, 2 (1) https://doi.org/10.1038/s41538-017-0010-4
- Tiantian Zhao, Qi Zhang, Shuguang Wang, Chaoying Qiu, Yang Liu, Guowan Su, Mouming Zhao. Effects of Maillard reaction on bioactivities promotion of anchovy protein hydrolysate: The key role of MRPs and newly formed peptides with basic and aromatic amino acids. LWT 2018, 97 , 245-253. https://doi.org/10.1016/j.lwt.2018.06.051
- Haider M Alkaabi, Hadi M Almayali. Effect of Bioactive Compounds Extracted from Green Algae Spirogyra sp. in Reducing the Protoscolices Viability In vitro Compared with Albendazole Drug. Journal of Pure and Applied Microbiology 2018, 12 (3) , 1221-1231. https://doi.org/10.22207/JPAM.12.3.23
- Rani N. Patil, A. Vijay Kumar. Biomimetic Clauson‐Kass and Paal‐Knorr Pyrrole Synthesis Using β ‐Cyclodextrin‐SO 3 H under Aqueous and Neat Conditions ‐ Application to Formal Synthesis of Polygonatine †. ChemistrySelect 2018, 3 (34) , 9812-9818. https://doi.org/10.1002/slct.201801559
- Xinliu Zhang, Hao Gao, Chunyan Wang, Abdul Qayum, Zhishen Mu, Zengli Gao, Zhanmei Jiang. Characterization and comparison of the structure and antioxidant activity of glycosylated whey peptides from two pathways. Food Chemistry 2018, 257 , 279-288. https://doi.org/10.1016/j.foodchem.2018.02.155
- Samar Abdeltaif, Khitma SirElkhatim, Amro Hassan. Estimation of Phenolic and Flavonoid Compounds and Antioxidant Activity of Spent Coffee and Black Tea (Processing) Waste for Potential Recovery and Reuse in Sudan. Recycling 2018, 3 (2) , 27. https://doi.org/10.3390/recycling3020027
- Muhammad-Javeed Akhtar, Martin Mondor, Mohammed Aïder. Impact of the drying mode and ageing time on sugar profiles and antioxidant capacity of electro-activated sweet whey. International Dairy Journal 2018, 80 , 17-25. https://doi.org/10.1016/j.idairyj.2017.12.013
- Min Yu, Shudong He, Mingming Tang, Zuoyong Zhang, Yongsheng Zhu, Hanju Sun. Antioxidant activity and sensory characteristics of Maillard reaction products derived from different peptide fractions of soybean meal hydrolysate. Food Chemistry 2018, 243 , 249-257. https://doi.org/10.1016/j.foodchem.2017.09.139
- Yalian Zhou, Meng Cui, Qin Yin, Min Deng, Yingbin Hao, Xueyong Huang, Liping Luo. Analysis of coffee seed vigor by extractive electrospray ionization mass spectrometry. Analytical Methods 2018, 10 (8) , 867-873. https://doi.org/10.1039/C7AY02403G
- Loh Teng-Hern Tan, Kok-Gan Chan, Chim Kei Chan, Tahir Mehmood Khan, Learn-Han Lee, Bey-Hing Goh. Antioxidative Potential of a Streptomyces sp. MUM292 Isolated from Mangrove Soil. BioMed Research International 2018, 2018 , 1-13. https://doi.org/10.1155/2018/4823126
- Takayuki Shibamoto. Novel methods of antioxidant assay combining various principles. 2017, 209-223. https://doi.org/10.1002/9781119135388.ch11
- Su Jeong Lee, Mina K. Kim, Kwang-Geun Lee. Effect of reversed coffee grinding and roasting process on physicochemical properties including volatile compound profiles. Innovative Food Science & Emerging Technologies 2017, 44 , 97-102. https://doi.org/10.1016/j.ifset.2017.07.009
- Ibrahim Elghamry, Magdy M. Youssef, Mohammed A. Al-Omair, Hany Elsawy. Synthesis, antimicrobial, DNA cleavage and antioxidant activities of tricyclic sultams derived from saccharin. European Journal of Medicinal Chemistry 2017, 139 , 107-113. https://doi.org/10.1016/j.ejmech.2017.07.079
- Natalia Ranalli, Silvina C. Andrés, Alicia N. Califano. Dulce de leche‐like product enriched with emulsified pecan oil: Assessment of physicochemical characteristics, quality attributes, and shelf‐life. European Journal of Lipid Science and Technology 2017, 119 (7) https://doi.org/10.1002/ejlt.201600377
- Elżbieta Wojtowicz, Aldona Krupska, Renata Zawirska-Wojtasiak. Antioxidant activity and free radicals of roasted herbal materials. Herba Polonica 2017, 63 (2) , 34-41. https://doi.org/10.1515/hepo-2017-0011
- Juan Sun, Peng-Cheng Lv, Hai-Liang Zhu. Tyrosyl-tRNA synthetase inhibitors: a patent review. Expert Opinion on Therapeutic Patents 2017, 27 (5) , 557-564. https://doi.org/10.1080/13543776.2017.1273350
- Qilin Tang, Gangliang Huang, Fengying Zhao, Lu Zhou, Shiqi Huang, Hui Li. The antioxidant activities of six (1 → 3)-β- d -glucan derivatives prepared from yeast cell wall. International Journal of Biological Macromolecules 2017, 98 , 216-221. https://doi.org/10.1016/j.ijbiomac.2017.01.132
- Hanen Ben Ayed, Noomen Hmidet, Max Béchet, Philippe Jacques, Moncef Nasri. Identification and natural functions of cyclic lipopeptides from Bacillus amyloliquefaciens An6. Engineering in Life Sciences 2017, 17 (5) , 536-544. https://doi.org/10.1002/elsc.201600050
- Sirima Takeungwongtrakul, Soottawat Benjakul. Biscuits fortified with micro-encapsulated shrimp oil: characteristics and storage stability. Journal of Food Science and Technology 2017, 54 (5) , 1126-1136. https://doi.org/10.1007/s13197-017-2545-4
- Ourdia Kareb, Ahmed I. Gomaa, Claude P. Champagne, Julie Jean, Mohammed Aïder. Impact of electro-activation on antioxidant properties of defatted whey. International Dairy Journal 2017, 65 , 28-37. https://doi.org/10.1016/j.idairyj.2016.09.009
- Benjamin M. Dorsey, Marjorie A. Jones. Healthy components of coffee processing by-products. 2017, 27-62. https://doi.org/10.1016/B978-0-12-811290-8.00002-5
- Adane Tilahun Getachew, Byung Soo Chun. Influence of pretreatment and modifiers on subcritical water liquefaction of spent coffee grounds: A green waste valorization approach. Journal of Cleaner Production 2017, 142 , 3719-3727. https://doi.org/10.1016/j.jclepro.2016.10.096
- Hadeel Ali Ghazzawi, Khalid Al-Ismail. A Comprehensive Study on the Effect of Roasting and Frying on Fatty Acids Profiles and Antioxidant Capacity of Almonds, Pine, Cashew, and Pistachio. Journal of Food Quality 2017, 2017 , 1-8. https://doi.org/10.1155/2017/9038257
- Silvia De Luca, Martina De Filippis, Remo Bucci, Andrea D. Magrì, Antonio L. Magrì, Federico Marini. Characterization of the effects of different roasting conditions on coffee samples of different geographical origins by HPLC-DAD, NIR and chemometrics. Microchemical Journal 2016, 129 , 348-361. https://doi.org/10.1016/j.microc.2016.07.021
- Hadi Bagheri, Mahdi Kashaninejad, Aman M. Ziaiifar, Mehran Aalami. Novel hybridized infrared-hot air method for roasting of peanut kernels. Innovative Food Science & Emerging Technologies 2016, 37 , 106-114. https://doi.org/10.1016/j.ifset.2016.08.014
- Fan Qiu, Tian-Zhen He, Yu-Qing Zhang. The isolation and the characterization of two polysaccharides from the branch bark of mulberry (Morus alba L.). Archives of Pharmacal Research 2016, 39 (7) , 887-896. https://doi.org/10.1007/s12272-016-0742-8
- Ayman Mohammed El Anany. Nutritional composition, antinutritional factors, bioactive compounds and antioxidant activity of guava seeds (Psidium Myrtaceae) as affected by roasting processes. Journal of Food Science and Technology 2015, 52 (4) , 2175-2183. https://doi.org/10.1007/s13197-013-1242-1
- Rhan-Kee Kang, Kwan-Sik Min, Myung-Hwa Kang. Physicochemical Properties of Supremo Coffee according to Grinding and Brewing Conditions. Journal of the Korean Society of Food Science and Nutrition 2015, 44 (1) , 89-96. https://doi.org/10.3746/jkfn.2015.44.1.089
- Alex Keng-Chee Saw, Wan-Sinn Yam, Keng-Chong Wong, Choon-Sheen Lai. A Comparative Study of the Volatile Constituents of Southeast Asian Coffea arabica , Coffea liberica and Coffea robusta Green Beans and their Antioxidant Activities. Journal of Essential Oil Bearing Plants 2015, 18 (1) , 64-73. https://doi.org/10.1080/0972060X.2014.977580
- Xiaomei Wang, Zhongshan Zhang, Mingxing Zhao. Carboxymethylation of polysaccharides from Tremella fuciformis for antioxidant and moisture-preserving activities. International Journal of Biological Macromolecules 2015, 72 , 526-530. https://doi.org/10.1016/j.ijbiomac.2014.08.045
- E. Gülruh Duruk, H. Yasemin Yenilmez, Ahmet Altındal, Zehra Altuntaş Bayır. Microwave-assisted synthesis of novel non-peripherally substituted metallophthalocyanines and their sensing behaviour for a broad range of Lewis bases. Dalton Transactions 2015, 44 (21) , 10060-10068. https://doi.org/10.1039/C5DT00852B
- Hana Maalej, Dorsaf Moalla, Claire Boisset, Sana Bardaa, Hanen Ben Ayed, Zouheir Sahnoun, Tarek Rebai, Moncef Nasri, Noomen Hmidet. Rhelogical, dermal wound healing and in vitro antioxidant properties of exopolysaccharide hydrogel from Pseudomonas stutzeri AS22. Colloids and Surfaces B: Biointerfaces 2014, 123 , 814-824. https://doi.org/10.1016/j.colsurfb.2014.10.017
- Ningjian Liang, David Kitts. Antioxidant Property of Coffee Components: Assessment of Methods that Define Mechanisms of Action. Molecules 2014, 19 (11) , 19180-19208. https://doi.org/10.3390/molecules191119180
- Zhongshan Zhang, Xiaomei Wang, Mingxing Zhao, Kun Qian. Optimization of polysaccharides extraction from Clematis huchouensis Tamura and its antioxidant activity. Carbohydrate Polymers 2014, 111 , 762-767. https://doi.org/10.1016/j.carbpol.2014.04.103
- Xiaomei Wang, Zhongshan Zhang, Mingxing Zhao, Huimin Qi. Effect of phthaloylation on radical-scavenging and moisture-preserving activities of polysaccharide from Enteromorpha linza. Carbohydrate Polymers 2014, 111 , 729-733. https://doi.org/10.1016/j.carbpol.2014.04.104