The effect of extraction of probe ultrasound on antioxidant properties of bounded and free phenols of Hyssop (Hyssopus officinalis) extract

Document Type : Research Paper

Authors

Abstract

Introduction: Excessive oxidative stress can cause multiple chronic diseases such as diabetes, cardiovascular disease, and cancer and aging-related diseases (Kawabata et al 2015). Phytochemicals reduce cardiovascular disease by decreasing the oxidation of LDL, the absorption and synthesis of cholesterol, blood pressure and increasing the blood clotting time. Also, the potential chemical prevention property of these compounds against cancer is caused by their ability to moderate the epigenetic changes of cancer cells (Mahan et al. 2012). Polyphenols have antioxidant activity, plant polyphenols have different functions and can act as a reducing agent, Phenolic acids and their derivatives form a large group of polyphenols that play an important role in the structure of plants, including the cell wall. (Keshavarz et al 2010). The phenolic acids can be classified as either free or bonded phenolic acids (Renger and Steinhart 2000). Free phenolic compounds in the gastrointestinal system can act against the incidence of colon cancer and other chronic diseases, free phenolic acids can be extracted with solvents such as water, methanol, ethanol and acetone. (Min et al 2012). Bonded phenolic acids are compounds that are insoluble, and are bonded to structural components of cellular wall such as cellulose, hemicellulose (for example arabinoxylans), lignin, pectin and structural proteins (Acosta et al 2014). They cannot be extracted by common techniques which lead to less prediction of total phenolic content from the real extent (Ti and al 2014). Hyssop, scientifically known as Hyssopus officinalis, that belongs to the Lamiaceae family (Ghasemi et al 1392). This plant is used as a flavoring and improving organoleptic properties in the food industry and has aromatic compounds that is used in soaps, cosmetics and perfumes. This plant is rich in volatile oils, flavonoids, tannins, marrubiin. This plant has antimicrobial, laxative and antispasmodic properties and has strong antiviral activity against HIV. It is antibacterial, antifungal and has antioxidant properties. Thus, the study aimed at the separation of the free and bonded phenolic factions and the determination of the phenolic content and antioxidant activity of hyssop plant leaf (Hyssopus officinalis) which partly contributes to the better prediction of the phenolic content and antioxidant activity.
Material and methods: Extraction of the hyssop plant leaf was carried out by using ultrasound probe under 10 and 20 minutes and the intensity of 60 - 100 W and the use of ethanol: water with ratios (80:20) and (50:50) and separating free phenolic fractions from the extractions using methanol and ultrasound for one hour (adjust the pH in the range of 4.5-5.5 by using 6M HCl), Then centrifuged at 4321 g, for 25 min, the supernatant is free phenolic. And then separating the bonded phenolic factions from residues resulting from the extraction of free phenolic by using caustic soda and ultrasound for two hours (adjust the pH in the range of 4.5-5.5 by using 6M HCl) and then centrifuged at 4321 g for 25 min, the supernatant was used as bonded phenolic extract (Kotásková et al 2016). The antioxidant activity was measured by free radical inhibition tests (DPPH) and the evaluation of colorlessness of beta carotene - linoleic acid, and oxidative stability test (OSI).
Results and discussion: The results of this study show that hyssop leaf extract which was extracted by ultrasound probe method contains significant amounts of phenolic and flavonoid compounds and there is a direct relationship between these compounds. Therefore, it can be concluded that hyssop leaf extract has antioxidant activity, and the highest amount of phenolic and flavonoid compounds of the extract, free and bonded phenolic compounds are (20-100-80) respectively. According to the determination of antioxidant activity by DPPH test, the maximum inhibition percentage for the obtained extract from treatment is (20-100-80) and the maximum inhibition amount for free and bonded phenols of the treatment is (20-60-80) and the least IC50 of the obtained extract from the treatment is (20-60-80); and is (20-100-80) for free and bonded phenols and the best treatment of free and bonded fractions was shown by the treatment (20-100-80) in the beta - carotene and OSI tests. Thus, there is a direct relationship between phenolic content, free and bonded phenols in beta - carotene and OSI tests. In DPPH radical inhibition, there was no correlation between phenolic content and antioxidant activity, which could be related to other factors (synergistic or antagonistic effect between active compounds, number and location of hydroxyl groups, presence of impurity in the extract, extraction method, etc.). The results also showed that free phenolic fractions had higher phenolic content and better antioxidant activity than bonded phenols. Free and bonded phenols have benefits for health. The released phenolic compounds in food matrix are used as food preservative. In order to use bonded phenolic compounds in food, pharmaceutical and cosmetic industry, some methods should be designed to release and extract them from the field crops and obtained sediments from extraction, which includes a large part of bonded phenols. Also, separation of free phenols can produce bioactive compounds with high antioxidant properties and can be used more efficiently in food and pharmaceutical industry.
Conclusion: Generally, the ratio of solvents, ultrasound intensity and extraction time affect the antioxidant power of hyssop extract. These points indicate the efficiency of ultrasound for recovery of phenolic compounds is mainly due to the cavitation phenomenon. This is due to the emission of ultrasonic waves through a liquid medium which damage the plant wall and improve the solvent penetration and subsequently release the phenolic compounds. In addition, organic solvents are replaced with those which have no toxic effects and consume less energy during the process compared to conventional methods. It also reduces the process time and temperature, which leads it to be useful for extraction of heat - sensitive compounds, such as phenolic compounds. All of these characteristics indicate that ultrasound can be used as a new and alternative process for the use of agricultural and industrial remains and efficient extraction of the phenolic compounds; and it leads to the production of products with high value which have a lot of profit in the industry and finally, it pollutes the environment less than conventional methods.

References

خلیلی م، ابراهیم‌زاده م، ۱۳۹۳.  آنتی‌اکسیدان‌ها و برخی از روش‌های متداول اندازه گیری آن‌ها، مجله دانشگاه علوم پزشکی مازندران، 24(120)، 208-188.
روحانی ر، عین افشار س و احمدزاد ر. 1394 ، استخراج ترکیبات آنتوسیانینی و آنتی اکسیدانی پرچم گل زعفران به کمک فناوری امواج فراصوت، نشریه پژوهش‌های علوم و صنایع غذایی ایران، 11(2)، 170-161.
قاسمی ع، حمیدی ح، آروس ج، معصومی ع. 1392 ، بررسی اثر شوری و دما بر جوانه‌زنی بذرگیاه دارویی زوفا(Hyssopus officinalis), مجله دانشگاه تهران. به زراعی کشاورزی، 15(3)، 169-155.
قربانی م، ابونجمی م، قربانی جاوید م، عرب حسینی ا. 1396 ، تأثیر امواج فراصوت بر میزان استخراج آسکوربیک اسید از دانه رازیانه و توانایی عصاره آن در بهبود ویژگی‌های آنتی اکسیدانی، نشریه پژوهش‌های صنایع غذایی ایران، 27(1)، 71-59.
قره خانی م، صادقی ماهونک ع، قربانی م. ۱۳۸۷ ، آنتی اکسیدان های طبیعی : ترکیبات عملگر جدید، دومین کنفرانس ملی غذای فراسودمند (عملگر)، تهران، دانشگاه تربیت مدرس،  ۴52 ‌- ۴43.
نصیری‌فر ز، صادقی‌ماهونک ع و کمالی ف. 1392 ، تاثیر شرایط عصاره‌گیری به کمک فراصوت بر میزان استخراج ترکیبات فنولی و فلاونوئیدی از  (Celtis australis)میوه داغداغان، نشریه فرآوری و نگهداری مواد غذایی، 5(2)، 130-115.
Acosta-Estrada BA, Gutiérrez-Uribe JA, Serna-Saldívar SO, 2014. Bound phenolics in foods, a review. Food    Chemistry 152: 46–55.
Alighourchi HR, Barzegar M, Sahari MA, Abbasi S, 2013. Effect of sonication on anthocyanins, total phenolic content, and antioxidant capacity of pomegranate juices. International Food Research Journal 20: 1703–1709.
Amarowicz R, Pegg RB, Rahimi-Moghaddam P, Barl B, Weil JA, 2004. Free-radical scavenging capacity and antioxidant activity of selected plant species from the Canadian prairies. Food Chemistry 84: 551–562.
Andreasen MF, Kroon PA, Williamson G, Garcia-Conesa MT, 2001. Intestinal release and uptake of phenolic antioxidant diferulic acids. Free Radical Biology and Medicine 31: 304–314.
Ashokkumar M, Sunartio D, Kentish S, Mawson R, Simons L, Vilkhu K, Versteeg C (Kees), 2008. Modification of food ingredients by ultrasound to improve functionality: A preliminary study on a model system. Innovative Food Science and Emerging Technologies 9: 155–160.
Bhat R, Kamaruddin NSBC, Min-Tze L, & Karim AA, 2011. Sonication improves kasturi lime (Citrus microcarpa) juice quality. Ultrasonics Sonochemistry 18(6): 1295–1300.
Bower JA, 2009. Statistical Methods for Food Science: Introductory procedures for the food practitioner, Statistical Methods for Food Science: Introductory procedures for the food practitioner. Wiley-Blackwell.
Capannesi C, Palchetti I, Mascini M, Parenti A, 2000. Electrochemical sensor and biosensor for polyphenols detection in olive oils. Food Chemistry 71: 553–562.
Carrera C, Ruiz-Rodríguez A, Palma M, Barroso CG, 2012. Ultrasound assisted extraction of phenolic compounds from grapes. Analytica Chimica Acta 732: 100–104.
Casal S, Malheiro R, Sendas A, Oliveira BPP, Pereira JA, 2010. Olive oil stability under deep-frying conditions. Food and Chemical Toxicology 48: 2972–2979.
Chandrasekara A, Shahidi F, 2010. Content of insoluble bound phenolics in millets and their contribution to antioxidant capacity. Journal of Agricultural and Food Chemistry 58: 6706–6714. doi:10.1021/jf100868b
Chen PX, Tang Y, Marcone MF, Pauls PK, Zhang B, Liu R, Tsao R, 2015. Characterization of free, conjugated and bound phenolics and lipophilic antioxidants in regular- and non-darkening cranberry beans (Phaseolus vulgaris L.). Food Chemistry 185: 298–308.
Chemat F, Rombaut N, Sicaire AG, Meullemiestre A, Fabiano-Tixier AS, Abert-Vian M, 2017. Ultrasound assisted extraction of food and natural products. Mechanisms, techniques, combinations, protocols and applications. A review. Ultrasonics Sonochemistry. 34: 540–560
Corbin C, Fidel T, Leclerc EA, Barakzoy E, Sagot N, Falguiéres A, Renouard S, Blondeau JP, Ferroud C, Doussot J, Lainé E, Hano C, 2015. Development and validation of an efficient ultrasound assisted extraction of phenolic compounds from flax (Linum usitatissimum L.) seeds. Ultrasonics Sonochemistry 26: 176–185.
Dayana Priyadharshini S, Bakthavatsalam AK, 2016. Optimization of phenol degradation by the microalga Chlorella pyrenoidosa using Plackett-Burman Design and Response Surface Methodology. Bioresource Technology 207: 150–156.
Dorman HJD, Peltoketo A, Hiltunen R, Tikkanen MJ, 2003. Characterisation of the antioxidant properties of de-odourised aqueous extracts from selected Lamiaceae herbs. Food Chemistry 83: 255–262.
De Guzman R, Tang H, Salley S, Ng KYS, 2009. Synergistic effects of antioxidants on the oxidative stability of soybean oil- and poultry fat-based biodiesel. JAOCS, Journal of the American Oil Chemists’ Society 86: 459–467.
Falleh H, Ksouri R, Lucchessi ME, Abdelly C, Magné C, 2012. Ultrasound-assisted extraction: Effect of extraction time and solvent power on the levels of polyphenols and antioxidant activity of Mesembryanthemum edule L. Aizoaceae shoots. Tropical Journal of Pharmaceutical Research 11: 243–249.
Farhoosh R, 2007. The effect of operational parameters of the Rancimat method on the determination of the oxidative stability measures and shelf-life prediction of soybean oil. JAOCS, Journal of the American Oil Chemists’ Society 84: 205–209.
Farhoosh R, Moosavi SMR, 2007. Rancimat test for the assessment of used frying oils quality. Journal of Food Lipids 14: 263–271
Fathiazad F, Hamedeyazdan S. (2011) A review on Hyssopus officinalis L.: Composition and biological activities. African Journal of Pharmacy and Pharmacology. 5(17):1959-1966
Ghafoor K, Choi YH, Jeon JY, & Jo IH, (2009). Optimization of ultrasound-assisted extraction of phenolic compounds, antioxidants, and anthocyanins from grape (Vitis vinifera) seeds. Journal of Agricultural and Food Chemistry 57(11): 4988–4994.
Galvan D’Alessandro L, Kriaa K, Nikov I, Dimitrov K, 2012. Ultrasound assisted extraction of polyphenols from black chokeberry. Separation and Purification Technology 93: 42–47.
Garcia-Castello EM, Rodriguez-Lopez AD, Mayor L, Ballesteros R, Conidi C, Cassano A, 2015. Optimization of conventional and ultrasound assisted extraction of flavonoids from grapefruit (Citrus paradisi L.) solid wastes. LWT - Food Science and Technology 64: 1114–1122.
Gökmen V, Serpen A, Fogliano V, 2009. Direct measurement of the total antioxidant capacity of foods: the ‘QUENCHER’ approach. Trends in Food Science & Technology 20: 278–288.
Guimarães R, Barros L, Barreira JCM, Sousa MJ, Carvalho AM, Ferreira ICFR, 2010. Targeting excessive free radicals with peels and juices of citrus fruits: Grapefruit, lemon, lime and orange. Food and Chemical Toxicology 48: 99–106.
Hatami T, Emami SA, Miraghaee SS, Mojarrab M, 2014. Total Phenolic Contents and Antioxidant Activities of Different Extracts and Fractions from the Aerial Parts of Artemisia biennis Willd. Iranian journal of pharmaceutical research 13: 551–9.
Herrera MC, Luque De Castro MD, 2004. Ultrasound-assisted extraction for the analysis of phenolic compounds in strawberries. Analytical and Bioanalytical Chemistry 37: 1106–1112.
Horžić D, Jambrak AR, Belščak-Cvitanović A, Komes D, Lelas V, 2012. Comparison of Conventional and Ultrasound Assisted Extraction Techniques of Yellow Tea and Bioactive Composition of Obtained Extracts. Food and Bioprocess Technology 5: 2858–2870.
Hossain MB, Brunton NP, Patras A, Tiwari B, O’Donnell CP, Martin-Diana AB, Barry-Ryan C, 2012. Optimization of ultrasound assisted extraction of antioxidant compounds from marjoram (Origanum majorana L.) using response surface methodology. Ultrasonics Sonochemistry 19: 582–590.
Huang HS, & Liaw ET, 2017. Extraction optimization of flavonoids from hypericum formosanum and matrix metalloproteinase-1 inhibitory activity. Molecules: 22(12).
Inglett GE, Chen D, Berhow M, Lee S, 2011. Antioxidant activity of commercial buckwheat flours and their free and bound phenolic compositions. Food Chemistry 125: 923–929.
Jovanovic A, Djordjevic V, Zdunic G, Savikin K, Pljevljakusic D, & Bugarski B ,2016. Ultrasound-assisted extraction of polyphenols from Thymus serpyllum and its antioxidant activity. Hemijska Industrija, 70(4): 391–398.
Juntachote T, & Berghofer E, 2005. Antioxidative properties and stability of ethanolic extracts of Holy basil and Galangal. Food Chemistry 92(2): 193–202.
Kallithraka S, Garcia‐Viguera C, Bridle P, Bakker J, 1995. Survey of solvents for the extraction of grape seed phenolics. Phytochemical Analysis 6: 265–267.
Kamali Roosta L, Ghavami M, Gharachoorloo M, Azizinezhad R, )2011(. Extracting cinnamon extracts and studying their effects on the stability of sunflower oil, The Journal of the Nutritional Sciences and Food Industry of Iran. 6(1): 13 – 22.
Kaisoon O, Siriamornpun S, Weerapreeyakul N, Meeso N, 2011. Phenolic compounds and antioxidant activities of edible flowers from Thailand. Journal of Functional Foods 3: 88–99.
Kawabata K, Mukai R, Ishisaka A, 2015. Quercetin and related polyphenols: New insights and implications for their bioactivity and bioavailability. Food and Function 6: 1399–1417.
Keshavarz M, Mostafaie A, Mansouri K, Bidmeshkipour A, Motlagh HRM, Parvaneh S, 2010. In vitro and ex vivo antiangiogenic activity of Salvia officinalis. Phytotherapy research 24: 1526–1531.
Khan MK, Abert-Vian M, Fabiano-Tixier AS, Dangles O, Chemat F, 2010. Ultrasound-assisted extraction of polyphenols (flavanone glycosides) from orange (Citrus sinensis L.) peel. Food Chemistry 119: 851–858.
Kotásková E, Sumczynski D, Mllček J, Valášek P, 2016. Determination of free and bound phenolics using HPLC-DAD, antioxidant activity and in vitro digestibility of Eragrostis tef. Journal of Food Composition and Analysis 46: 15–21.
Lai H, Lim Y, 2011. Evaluation of Antioxidant Activities of the Methanolic Extracts of Selected Ferns in Malaysia. International Journal of Environmental Science and Development 2: 442–447.
Lanez T, Haoua KB, 2017. The effect of soxhlet and ultrasonic-assisted extraction on antioxidant components and antioxidant properties of selected south Algerian red potatoes cultivars. Chemistry & Chemical Engineering, Biotechnology, Food Industry, 18 (4): 435 – 448
Liang YC, May CY, Foon CS, Ngan MA, Hock CC, Basiron Y, 2006. The effect of natural and synthetic antioxidants on the oxidative stability of palm diesel. Fuel 85: 867–870.
Locatelli M, Gindro R, Travaglia F, Coïsson JD, Rinaldi M, Arlorio M, 2009. Study of the DPPH {radical dot}-scavenging activity: Development of a free software for the correct interpretation of data. Food Chemistry 114: 889–897.
Lee SH, Kang MC, Moon SH, Jeon BT, Jeon YJ, 2013. Potential use of ultrasound in antioxidant extraction from Ecklonia cava. Algae 28: 371–378.
Liu X, Dong M, Chen X, Jiang M, Lv X, Yan G, 2007. Antioxidant activity and phenolics of an endophytic Xylaria sp. from Ginkgo biloba. Food Chemistry 105: 548–554.
Maghsoudlou E, Esmaeilzadeh Kenari R, Raftani Amiri Z, 2017. Evaluation of Antioxidant Activity of Fig (Ficus carica) Pulp and Skin Extract and Its Application in Enhancing Oxidative Stability of Canola Oil. Journal of Food Processing and Preservation 41(4).
Mahan L, Escott-Stump S, Raymond J, Krause M, 2012. Krause’s food & the nutrition care process, US Patent 1,503,006: 36–40.
Máriássyová M, 2006. Antioxidant activity of some herbal extracts in rapeseed and sunflower oils. Journal of Food and Nutrition Research 45: 104–109.
Meullemiestre A, Petitcolas E, Maache-Rezzoug Z, Chemat F, Rezzoug SA, 2016. Impact of ultrasound on solid-liquid extraction of phenolic compounds from maritime pine sawdust waste. Kinetics, optimization and large scale experiments. Ultrasonics Sonochemistry 28: 230–239.
Min B, Gu L, McClung AM, Bergman CJ, Chen MH, 2012. Free and bound total phenolic concentrations, antioxidant capacities, and profiles of proanthocyanidins and anthocyanins in whole grain rice (Oryza sativa L.) of different bran colours. Food Chemistry 133: 715–722.
Mohammedi Z, & Atik F, 2011. Impact of solvent extraction type on total polyphenols content and biological activity from Tamarix aphylla (L.) Karst. International Journal of Pharma and Bio Sciences, 2(1): 609–615.
Morelló JR, Romero MP, Ramo T, Motilva MJ, 2005. Evaluation of l-phenylalanine ammonia-lyase activity and phenolic profile in olive drupe (Olea europaea L.) from fruit setting period to harvesting time. Plant Science 168: 65–72.
Muñiz-Márquez B, Martínez-Ávila GC, Wong-Paz JE, Belmares-Cerda R, Rodríguez-Herrera R, Aguilar CN, 2013. Ultrasound-assisted extraction of phenolic compounds from Laurus nobilis L. and their antioxidant activity. Ultrasonics Sonochemistry 20: 1149–1154.
Osawa WO, Sahoo PK, Onyari JM, Mulaa FJ, 2016. Effects of antioxidants on oxidation and storage stability of Croton megalocarpus biodiesel. International Journal of Energy and Environmental Engineering 7: 85–91.
Patras A, Brunton NP, O’Donnell C, Tiwari BK, 2010. Effect of thermal processing on anthocyanin stability in foods; mechanisms and kinetics of degradation. Trends in Food Science and Technology. 21: 3–11
Peričin D, Krimer V, Trivić S, Radulović L, 2009. The distribution of phenolic acids in pumpkin’s hull-less seed, skin, oil cake meal, dehulled kernel and hull. Food Chemistry 113: 450–456.
Perry A, Rasmussen H, Johnson EJ, 2009. Xanthophyll (lutein, zeaxanthin) content in fruits, vegetables and corn and egg products. Journal of Food Composition and Analysis 22: 9–15.
Potterat O, 1997. Antioxidants and free radical scavengers of natural origin. Current Organic Chemistry 1(4):415–440.
Richheimer SL, Bernart MW, King GA, Kent MC, Bailey DT, 1996. Antioxidant activity of lipid-soluble phenolic diterpenes from rosemary. JAOCS, Journal of the American Oil Chemists’ Society 73: 507–514.
Renger A, Steinhart H, 2000. Ferulic acid dehydrodimers as structural elements in cereal dietary fibre. European Food Research and Technology 211: 422–428.
Roleira FMF, Tavares-Da-Silva EJ, Varela CL, Costa SC, Silva T, Garrido J, Borges F, 2015. Plant derived and dietary phenolic antioxidants: Anticancer properties. Food Chemistry 183: 235–258.
Şahin S, Şamli R, 2013. Optimization of olive leaf extract obtained by ultrasound-assisted extraction with response surface methodology. Ultrasonics Sonochemistry 20: 595–602.
Salta FN, Mylona A, Chiou A, Boskou G, Andrikopoulos NK, 2009. Oxidative stability of edible vegetable oils endriched in polyphenols with olive leaf extract. Food Science and Technology 13: 413-421
Sardarodiyan M, Mehraban ُSang Atash M, Arianfar A, 2016. 'The optimization and comparison of different extraction approaches (ultrasound and maceration) on chemical composition of Elaeagnus angustifolial L. extract', Eco-phytochemical Journal of Medicinal Plants 4(3): 74-94.
Siramon P, Ohtani Y, 2007. Antioxidative and antiradical activities of Eucalyptus camaldulensis leaf oils from Thailand. Journal of Wood Science 53: 498–504.
Sendzikiene E, Makareviciene V, Janulis P, 2005. Oxidation stability of biodiesel fuel produced from fatty wastes. Polish Journal of Environmental Studies 14: 335–339.
Subba Rao MVSST, Muralikrishna G, 2002. Evaluation of the antioxidant properties of free and bound phenolic acids from native and malted finger millet (ragi, Eleusine coracana Indaf-15). Journal of Agricultural and Food Chemistry 50: 889–892.
Sun T, Ho CT, 2005. Antioxidant activities of buckwheat extracts. Food Chemistry 90: 743–749.
Sumczynski D, Kotásková E, Družbíková H, Mlček J, 2016. Determination of contents and antioxidant activity of free and bound phenolics compounds and in vitro digestibility of commercial black and red rice (Oryza sativa L.) varieties. Food Chemistry 211: 339–346.
Ti H, Zhang R, Zhang M, Li Q, Wei Z, Zhang Y, Tang X, Deng Y, Liu L, Ma Y, 2014. Dynamic changes in the free and bound phenolic compounds and antioxidant activity of brown rice at different germination stages. Food Chemistry 161: 337–344.
Tepe B, Daferera D, Tepe AS, Polissiou M, Sokmen A, 2007. Antioxidant activity of the essential oil and various extracts of Nepeta flavida Hub-Mor. from Turkey. Food Chemistry 103: 1358–1364.
Tomšik A, Pavlić B, Vladić J, Ramić M, Brindza J, Vidović S, 2016. Optimization of ultrasound-assisted extraction of bioactive compounds from wild garlic (Allium ursinum L.). Ultrasonics Sonochemistry 29: 502–511.
Yanishlieva NV, Marinova E, Pokorný J, 2006. Natural antioxidants from herbs and spices. European Journal of Lipid Science and Technology 108: 776–793
Zieliński H, Kozłowska H, 2000. Antioxidant activity and total phenolics in selected cereal grains and their different morphological fractions. Journal of Agricultural and Food Chemistry 48: 2008–2016.
Food Research Journal
Volume 30, Issue 2
September 2020
Pages 101-129

Files

Share

How to cite

Statistics