Abstract
The extraction and quantitative determination of phenolic compounds (including phenolic acids, flavones, flavanols, alkaloid, tannins, procyanidins, and naphthoquinone) from the walnut kernel and its pellicle were performed by ultra-high-performance liquid chromatography coupled to tandem mass spectrometry (UHPLC-MS/MS). Effective parameters on the tandem MS conditions, chromatographic conditions, and extraction solvents were evaluated and optimized. Under optimum condition, limits of detection and linearity were 0.000565–33.3 μg/g and 10–1000 ng/mL with r-values > 0.9952, respectively. The relative standard deviation from extraction recovery was from 74.27 ± 2.81% to 109.52 ± 4.33%, with precision values of < 15%. The proposed method was applied for simultaneous extraction and determination of phenolic compounds not only in the walnut kernel and its pellicle, but also in other tree nuts.
Similar content being viewed by others
References
Acea J, Rivas D, Zonja B, Pérez S, Barceló D (2015) Liquid chromatography–mass spectrometry: quantification and confirmation aspects.
Ali J-E, Alireza O, Mahnaz T, Ryszard A (2019) A comparative review on the extraction, antioxidant content and antioxidant potential of different parts of walnut ( Juglans regia L.) fruit and tree. Molecules 24:2133–2173
Beyhan O, Gozlekci S, Gundogdu M, Ercisli S (2016) Physico-chemical and antioxidant characteristics in fruits of walnut (juglans regia L.) genotypes from inner anatolia. Notulae Botanicae Horti Agrobotanici Cluj-Napoca 44:586–592. https://doi.org/10.15835/nbha44210304
Bodoira RM, Maestri DM (2020) Phenolic compounds from nuts: extraction, chemical profiles and bioactivity. J Agric Food Chem 68:927–942. https://doi.org/10.1021/acs.jafc.9b07160
Cerdá FFJMPZaM-CJMB (2016) Total phenolics content, bioavailability and antioxidant capacity of 10 different genotypes of walnut (Juglans regia L.) J Food Nutr Res
Dang J, Zhang L, Wang Q, Mei L, Yue H, Liu Z, Shao Y, Gao Q, Tao Y (2018) Target separation of flavonoids from Saxifraga tangutica using two-dimensional hydrophilic interaction chromatography/reversed-phase liquid chromatography. J Sep Sci 41:4419–4429. https://doi.org/10.1002/jssc.201800534
Figueroa F, Marhuenda J, Zafrilla P, Villaño D, Martínez-Cachá A, Tejada L, Cerdá B, Mulero J (2016) High-performance liquid chromatography-diode array detector determination and availability of phenolic compounds in 10 genotypes of walnuts. Int J Food Prop 20:1074–1084. https://doi.org/10.1080/10942912.2016.1199036
Fuentealba C, Hernandez I, Saa S, Toledo L, Burdiles P, Chirinos R, Campos D, Brown P, Pedreschi R (2017) Colour and in vitro quality attributes of walnuts from different growing conditions correlate with key precursors of primary and secondary metabolism. Food Chem 232:664–672. https://doi.org/10.1016/j.foodchem.2017.04.029
Gao P, Liu R, Jin Q, Wang X (2019) Comparative study of chemical compositions and antioxidant capacities of oils obtained from two species of walnut: Juglans regia and Juglans sigillata. Food Chem 279:279–287. https://doi.org/10.1016/j.foodchem.2018.12.016
Gomez-Caravaca AM, Verardo V, Segura-Carretero A, Caboni MF, Fernandez-Gutierrez A (2008) Development of a rapid method to determine phenolic and other polar compounds in walnut by capillary electrophoresis-electrospray ionization time-of-flight mass spectrometry. J Chromatogr A 1209:238–245. https://doi.org/10.1016/j.chroma.2008.08.117
Jahanban-Esfahlan A, Ostadrahimi A, Tabibiazar M, Amarowicz R (2019) A comparative review on the extraction, antioxidant content and antioxidant potential of different parts of walnut (Juglans regia L.) fruit and tree. Molecules 24 doi:https://doi.org/10.3390/molecules24112133
Liu R, Su C, Xu Y, Shang K, Sun K, Li C, Lu J (2020) Identifying potential active components of walnut leaf that acton diabetes mellitus through integration of UHPLC-Q-orbitrap HRMS and network pharmacology analysis J Ethnopharmacol:112659 doi:https://doi.org/10.1016/j.jep.2020.112659
Moo-Huchin VM, Canto-Pinto JC, Cuevas-Glory LF, Sauri-Duch E, Perez-Pacheco E, Betancur-Ancona D (2019) Effect of extraction solvent on the phenolic compounds content and antioxidant activity of Ramon nut (Brosimum alicastrum). Chem Pap 73:1647–1657. https://doi.org/10.1007/s11696-019-00716-x
Paissoni MA, Rio Segade S, Carrero-Carralero C, Montanini C, Giacosa S, Rolle L (2020) Role of anthocyanin traits on the impact of oenological tannins addition in the first stage of red winegrape skin simulated maceration. Food Chem 320:126633. https://doi.org/10.1016/j.foodchem.2020.126633
Persic M, Mikulic-Petkovsek M, Halbwirth H, Solar A, Veberic R, Slatnar A (2018) Red walnut: characterization of the phenolic profiles, activities and gene expression of selected enzymes related to the phenylpropanoid pathway in pellicle during walnut development. J Agric Food Chem 66:2742–2748. https://doi.org/10.1021/acs.jafc.7b05603
Persic M, Mikulic-Petkovsek M, Slatnar A, Solar A, Veberic R (2018b) Changes in phenolic profiles of red-colored pellicle walnut and hazelnut kernel during ripening. Food Chem 252:349–355. https://doi.org/10.1016/j.foodchem.2018.01.124
Rashidipoura M, Heydari R (2018) Ultrasonic-assisted matrix solid-phase dispersion and high-performance liquid chromatography as an improved methodology for determination of oleuropein from olive leaves. Anal Bioanal Chem Res 5:307–316
Regueiro J, Sanchez-Gonzalez C, Vallverdu-Queralt A, Simal-Gandara J, Lamuela-Raventos R, Izquierdo-Pulido M (2014) Comprehensive identification of walnut polyphenols by liquid chromatography coupled to linear ion trap-Orbitrap mass spectrometry. Food Chem 152:340–348. https://doi.org/10.1016/j.foodchem.2013.11.158
Rezaeepour R, Heydari R, Ismaili A (2015) Ultrasound and salt-assisted liquid–liquid extraction as an efficient method for natural product extraction. Anal Methods 7:3253–3259. https://doi.org/10.1039/c5ay00150a
Rocchetti G, Chiodelli G, Giuberti G, Lucini L (2018) Bioaccessibility of phenolic compounds following in vitro large intestine fermentation of nuts for human consumption. Food Chem 245:633–640. https://doi.org/10.1016/j.foodchem.2017.10.146
Rosa R, Tassi L, Orteca G, Saladini M, Villa C, Veronesi P, Leonelli C, Ferrari E (2016) Process intensification by experimental design application to microwave-assisted extraction of phenolic compounds from Juglans regia L Food Anal. Methods 10:575–586. https://doi.org/10.1007/s12161-016-0624-1
Salcedo CL, Nazareno MA (2015) Effect of phenolic compounds on the oxidative stability of ground walnuts and almonds RSC. Advances 5:45878–45887. https://doi.org/10.1039/c5ra00245a
Sani T H , Hadjmohammadi M , . FMH (2020) Extraction and determination of flavonoids in fruit juices and vegetables using Fe3O4/SiO2 magnetic nanoparticles modified with mixed hemi/ad-micelle cetyltrimethylammonium bromide and high performance liquid chromatography. J Sep Sci 43(7) doi:https://doi.org/10.1002/jssc.201900527
Shen D, Wu S, Zheng Y, Han Y, Ni Z, Li S, Tang F, Mo R, Liu Y (2020) Characterization of iron walnut in different regions of China based on phytochemical composition. J Food Sci Technol:1–10
Shi BB, Zhang WN, Li X, Pan XJ (2018) Seasonal variations of phenolic profiles and antioxidant activity of walnut (Juglans sigillata Dode) green husks. Int J Food Prop 20:S2635–S2646. https://doi.org/10.1080/10942912.2017.1381706
Slatnar A, Mikulic-Petkovsek M, Stampar F, Veberic R, Solar A (2015) Identification and quantification of phenolic compounds in kernels, oil and bagasse pellets of common walnut (Juglans regia L.). Food Res Int 67:255–263. https://doi.org/10.1016/j.foodres.2014.11.016
Tapia MI, Sánchez-Morgado JR, García-Parra J, Ramírez R, Hernández T, González-Gómez D (2013) Comparative study of the nutritional and bioactive compounds content of four walnut (Juglans regia L.) cultivars. J Food Compos Anal 31:232–237. https://doi.org/10.1016/j.jfca.2013.06.004
Taş NG, Gökmen V (2017) Phenolic compounds in natural and roasted nuts and their skins: a brief review Current Opinion in Food. Science 14:103–109. https://doi.org/10.1016/j.cofs.2017.03.001
Tian-Peng Yina LC, Yang Chenb, Ying Lia, Ya-Rong Wangb, Chuan-Shui Liua, Zhong-Tao Ding (2015) Tannins and antioxidant activities of the walnut (Juglans regia) pellicle. Nat Prod Commun
Trandafir I, Cosmulescu S, Botu M, Nour V (2016) Antioxidant activity, and phenolic and mineral contents of the walnut kernel (Juglans regia L.) as a function of the pellicle color. Fruits 71:177–184. https://doi.org/10.1051/fruits/2016006
Viacava F, Santana-Galvez J, Heredia-Olea E, Perez-Carrillo E, Nair V, Cisneros-Zevallos L, Jacobo-Velazquez DA (2020) Sequential application of postharvest wounding stress and extrusion as an innovative tool to increase the concentration of free and bound phenolics in carrots. Food Chem 307:125551. https://doi.org/10.1016/j.foodchem.2019.125551
Vieira V, Prieto MA, Barros L, Coutinho JAP, Ferreira I, Ferreira O (2018) Enhanced extraction of phenolic compounds using choline chloride based deep eutectic solvents from Juglans regia L Ind Crops. Prod 115:261–271. https://doi.org/10.1016/j.indcrop.2018.02.029
Vu DC, Vo PH, Coggeshall MV, Lin CH (2018) Identification and characterization of phenolic compounds in black walnut kernels. J Agric Food Chem 66:4503–4511. https://doi.org/10.1021/acs.jafc.8b01181
Wu S, Ni Z, Wang R, Zhao B, Han Y, Zheng Y, Liu F, Gong Y, Tang F, Liu Y (2020) The effects of cultivar and climate zone on phytochemical components of walnut (Juglans regia L.). Food and Energy Security 9:e196 doi:https://doi.org/10.1002/fes3.196
Yang Z, Guo P, Han R, Gao JM (2018) Preparative separation of flavone dimers from Dysosma versipellis by counter-current chromatography: trifluoroacetic acid as a solvent system modifier. J Sep Sci 41:3631–3643. https://doi.org/10.1002/jssc.201800530
Zafrilla P, Cerdá B, Mulero J, Villaño A, Villaño D, Gironés-Vilaplana A, Marhuenda J, Figueroa F (2017) Soil and climate determine antioxidant capacity of walnuts Emirates. J Food Agric. https://doi.org/10.9755/ejfa.2016-10-1390
Zhang X, Zhang S, Gao B, Qian Z, Liu J, Wu S, Si J (2019) Identification and quantitative analysis of phenolic glycosides with antioxidant activity in methanolic extract of Dendrobium catenatum flowers and selection of quality control herb-markers. Food Res Int 123:732–745. https://doi.org/10.1016/j.foodres.2019.05.040
Funding
The authors gratefully acknowledge the funding supports from Fundamental Research Funds of CAF (CAFYBB2019QD002 and CAFYBB2017QC002).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Ethical Approval
This article does not contain any studies involving human participants or animals performed by any of the authors.
Informed Consent
Not applicable as this study does not include any human participants.
Conflict of Interest
The authors declare no competing interests. This article does not contain any studies with human or animal subjects.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Shen, D., Yuan, X., Zhao, Z. et al. Determination of Phenolic Compounds in Walnut Kernel and Its Pellicle by Ultra-high-Performance Liquid Chromatography-Tandem Mass Spectrometry. Food Anal. Methods 14, 2408–2419 (2021). https://doi.org/10.1007/s12161-021-02069-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12161-021-02069-2