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Licensed Unlicensed Requires Authentication Published by De Gruyter January 8, 2018

Extraction, characterization and biological activity of citrus flavonoids

Kavita Sharma

Kavita Sharma is a research professor in the School of Chemical Engineering, Yeungnam University, South Korea. She received her PhD at the Department of Molecular Biotechnology, College of Environmental and Life Sciences, Konkuk University, Seoul, South Korea, in 2015. A major part of her work is teaching graduate and post-graduate students along with mentoring research students on their work related to characterization and biological studies of active drug molecules. Apart from her excellent capabilities in the analysis, purification and characterization of many classes of challenging molecules, she is skilled in analytical instruments like HPLC, LC-MS, GC, NMR, UV/Vis spectroscopy, FTIR etc. Her research expertise includes life sciences, organic chemistry and medicinal chemistry.

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, Neelima Mahato

Neelima Mahato earned her doctoral degree in chemistry from the Indian Institute of Technology, BHU, India, in 2013. After her postdoctoral studies at IIT-Kanpur, India, and Yeungnam University, South Korea, she became an assistant professor at the latter in April 2014. Her research interests include electrochemistry, nanostructured materials and functional bioactive molecules.

and Yong Rok Lee

Yong Rok Lee is a Chunma distinguished professor at the School of Chemical Engineering at Yeungnam University, South Korea. He received his BS (1982) in chemistry from Chonbuk National University (South Korea) and his MS (1984) and PhD (1992) degrees in organic chemistry from Seoul National University (South Korea). He worked at Duke University as a postdoctoral fellow with Prof M. C. Pirrung (1993–1994), Ohio State University, as a postdoctoral fellow with Prof. L. Paquette (1995), and Michigan State University as a visiting professor with Prof. W. Wulff (2000). His current research focuses on organic synthesis and its applications, natural products syntheses and characterizations and development of medicines. He won awards for outstanding research from the Education Ministry of the Republic of Korea in 2014 and in the organic division of the Korean Chemical Society in 2017.

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Abstract

Citrus is one of the largest and most popular fruit crops commercially grown across the globe. It is not only important in terms of economy but is also popular for its nutritional benefits to human and farm animals. Citrus is available in several varieties, all with attractive colors. It is consumed either fresh or in processed form. After processing, approximately 50% of the fruit remains unconsumed and discarded as waste. The latter includes fruit pith residue, peels and seeds. Direct disposal of these wastes to the environment causes serious problems as these contain bioactive compounds. Release of these bioactive compounds to the open landfills cause bad odor and spread of diseases, and disposal to water bodies or seepage to the underground water table deteriorates water quality and harms aquatic life. In this regard, a number of research are being focused on the development of better reuse methods to obtain value-added phytochemicals as well as for safe disposal. The important phytochemicals obtained from citrus include essential oils, flavonoids, citric acid, pectin, etc., which have now become popular topics in industrial research, food and synthetic chemistry. The present article reviews recent advances in exploring the effects of flavonoids obtained from citrus wastes, the extraction procedure and their usage in view of various health benefits.

About the authors

Kavita Sharma

Kavita Sharma is a research professor in the School of Chemical Engineering, Yeungnam University, South Korea. She received her PhD at the Department of Molecular Biotechnology, College of Environmental and Life Sciences, Konkuk University, Seoul, South Korea, in 2015. A major part of her work is teaching graduate and post-graduate students along with mentoring research students on their work related to characterization and biological studies of active drug molecules. Apart from her excellent capabilities in the analysis, purification and characterization of many classes of challenging molecules, she is skilled in analytical instruments like HPLC, LC-MS, GC, NMR, UV/Vis spectroscopy, FTIR etc. Her research expertise includes life sciences, organic chemistry and medicinal chemistry.

Neelima Mahato

Neelima Mahato earned her doctoral degree in chemistry from the Indian Institute of Technology, BHU, India, in 2013. After her postdoctoral studies at IIT-Kanpur, India, and Yeungnam University, South Korea, she became an assistant professor at the latter in April 2014. Her research interests include electrochemistry, nanostructured materials and functional bioactive molecules.

Yong Rok Lee

Yong Rok Lee is a Chunma distinguished professor at the School of Chemical Engineering at Yeungnam University, South Korea. He received his BS (1982) in chemistry from Chonbuk National University (South Korea) and his MS (1984) and PhD (1992) degrees in organic chemistry from Seoul National University (South Korea). He worked at Duke University as a postdoctoral fellow with Prof M. C. Pirrung (1993–1994), Ohio State University, as a postdoctoral fellow with Prof. L. Paquette (1995), and Michigan State University as a visiting professor with Prof. W. Wulff (2000). His current research focuses on organic synthesis and its applications, natural products syntheses and characterizations and development of medicines. He won awards for outstanding research from the Education Ministry of the Republic of Korea in 2014 and in the organic division of the Korean Chemical Society in 2017.

Acknowledgments

This research was supported by the Nano Material Technology Development Program of the Korean National Research Foundation (NRF), funded by the Korea Ministry of Education, Science, and Technology (2012M3A7B4049675). This work was also supported by the National Research Foundation of Korea (NRF) grant funded by Priority Research Centers (2014R1A6A1031189).

  1. Conflict of interest statement: The authors declare that none has any conflict of interest.

  2. Human and animal rights: This article does not contain any studies with human or animal subjects.

References

Abad-García B, Berrueta LA, Garmón-Lobato S, Gallo B, Vicente F. A general analytical strategy for the characterization of phenolic compounds in fruit juices by high-performance liquid chromatography with diode array detection coupled to electrospray ionization and triple quadrupole mass spectrometry. J Chromatogr A 2009; 1216: 5398–5415.10.1016/j.chroma.2009.05.039Search in Google Scholar

Abascal K, Ganora L, Yarnell E. The effect of freeze-drying and its implications for botanical medicine: a review. Phytother Res 2005; 19: 655–660.10.1002/ptr.1651Search in Google Scholar

Abeysinghe DC, Li X, Sun C, Zhang W, Zhou C, Chen K. Bioactive compounds and antioxidant capacities in different edible tissues of citrus fruit of four species. Food Chem 2007; 104: 1338–1344.10.1016/j.foodchem.2007.01.047Search in Google Scholar

Adelina R, Supriyati MD, Nawangsari DA, Jenie RI, Meiyanto E. Citrus reticulata’s peels modulate blood cholesterol profile and increase bone density of ovariectomized rats. Indo J Biotech 2015; 13: 1092–1097.Search in Google Scholar

Agricultural Research Service. Chemistry and technology of citrus, citrus products and by-products. US Government Printing Office: Washington, DC, 1956.Search in Google Scholar

Aturki Z, Brandi V, Sinibaldi M. Separation of flavanone-7-O-glycoside diastereomers and analysis in citrus juices by multidimensional liquid chromatography coupled with mass spectrometry. J Agric Food Chem 2004; 52: 5303–5308.10.1021/jf0400967Search in Google Scholar

Baniya S, Dhananjaya DR, Acharya A, Dangi B, Sapkota A. Cardioprotective activity of ethanolic extract of Citrus grandis (L.) Osbeck peel on doxorubicin and cyclophosphamide induced cardiotoxicity in albino rats. Int J Pharma Sci Drug Res 2015; 7: 354–360.Search in Google Scholar

Barnes S, Kirk M, Coward L. Isoflavones and their conjugates in soy foods: extraction conditions and analysis by HPLC-mass spectrometry. J Agric Food Chem 1994; 42: 2466.10.1021/jf00047a019Search in Google Scholar

Bar-Peled M, Lewinsohn E, Fluhr R, Gressel J. UDP rhamnose: flavanone-7-O-glucoside-2″-O-rhamnosyltransferase. Purification and characterization of an enzyme catalyzing the production of bitter compounds in citrus. J Biol Chem 1991; 266: 20953–20959.10.1016/S0021-9258(18)54803-1Search in Google Scholar

Barreca D, Bisignano C, Ginestra G. Polymethoxylated, C- and O-glycosyl flavonoids in tangelo (Citrus reticulata×Citrus paradisi) juice and their influence on antioxidant properties. Food Chem 2013; 141: 1481–1488.10.1016/j.foodchem.2013.03.095Search in Google Scholar PubMed

Benavente-García O, Castillo J, Marin FR, Ortuño A, Del Río JA. Uses and properties of citrus flavonoids. J Agric Food Chem 1997; 45: 4505–4515.10.1021/jf970373sSearch in Google Scholar

Bilbao MdLM, Andrés-Lacueva C, Jáuregui O, Lamuela-Raventós RM. Determination of flavonoids in a citrus fruit extract by LC-DAD and LC-MS. Food Chem 2007; 101: 1742–1747.10.1016/j.foodchem.2006.01.032Search in Google Scholar

Bonaccorsi P, Caristi C, Gargiulli C, Leuzzi U. Flavonol glucoside profile of southern Italian red onion (Allium cepa L.). J Agric Food Chem 2005; 53: 2733–2740.10.1021/jf048152rSearch in Google Scholar PubMed

Bracke ME, Bruyneel EA, Vermeulen SJ, Vennekens K, Marck VV, Mareel MM. Citrus flavonoid effect on tumor invasion and metastasis. Food Technol 1994; 48: 121–124.Search in Google Scholar

Brito A, Javier E, Ramirez CA, Beatriz S, Mario JS. UV-MS profiles of phenolic compounds and antioxidant activity of fruits from three citrus species consumed in Northern Chile. Molecules 2014; 9: 17400–17421.10.3390/molecules191117400Search in Google Scholar

Calabro ML, Galtieri V, Cutroneo P, Tommasini S, Ficarra P, Ficarra R. Study of the extraction procedure by experimental design and validation of a LC method for determination of flavonoids in Citrus bergamia juice. J Pharm Biomed Anal 2004; 35: 349–363.10.1016/S0731-7085(03)00585-5Search in Google Scholar

Castillo J, Benavente-García O, Del Río JA. Hesperetin-7-glucoside and prunin in Citrus species C. aurantium and C. paradisi. A study of their quantitative distribution in immature fruits and as immediate precursors of neohesperidin and naringin in C. aurantium. J Agric Food Chem 1993; 41: 1920–1924.10.1021/jf00035a021Search in Google Scholar

Chanet A, Milenkovic D, Deval C, Potier M, Constans J, Mazur A, Bérard AM. Naringin, the major grapefruit flavonoid, specifically affects atherosclerosis development in diet-induced hypercholesterolemia in mice. J Nutr Biochem 2012; 23: 469–477.10.1016/j.jnutbio.2011.02.001Search in Google Scholar PubMed

Chang YH, Seo J, Song E, Choi HJ, Shim E, Lee O, Hwang J. Bioconverted jeju Hallabongtangor (Citrus kiyomi×ponkan) peel extracts by cytolase enhance antioxidant and anti-inflammatory capacity in RAW 264.7 cells. Nutr Res Pract 2016; 10: 131–138.10.4162/nrp.2016.10.2.131Search in Google Scholar PubMed PubMed Central

Chen J, Montanari AM, Widmer WW. Two new polymethoxylated flavones, a class of compounds with potential anticancer activity, isolated from cold pressed Dancy tangerine peel oil solids. J Agric Food Chem 1997; 45: 364–368.10.1021/jf960110iSearch in Google Scholar

Chinapongtitiwat V, Jongaroontaprangsee S, Chiewchan N, Devahastin S. Important flavonoids and limonin in selected Thai citrus residues. J Funct Foods 2013; 5: 1151–1158.10.1016/j.jff.2013.03.012Search in Google Scholar

Choi JS, Yokozawa T, Oura H. Improvement of hyperglycemia and hyperlipemia in streptozotocin diabetic rats by a methanolic extract of Prunusdavidiana stems and its main component, prunin. Planta Med 1991; 57: 208–211.10.1055/s-2006-960075Search in Google Scholar PubMed

Constant HL, Beecher CWW. A method for the dereplication of natural product extracts using electrospray HPLC/MS. Nat Prod Lett 1995; 6: 193.10.1080/10575639508043158Search in Google Scholar

Croft KD. The chemistry and biological effects of flavonoids and phenolic acids. Ann N Y Acad Sci 1998; 854: 435–442.10.1111/j.1749-6632.1998.tb09922.xSearch in Google Scholar PubMed

Dallas C, Gerbi A, Tenca G, Juchaux F, Bernard FX. Lipolytic effect of a polyphenolic citrus dry extract of red orange, grapefruit, orange (SINETROL) in human body fat adipocytes. Mechanism of action by inhibition of cAMP-phosphodiesterase (PDE). Phytomedicine 2008; 15: 783–792.10.1016/j.phymed.2008.05.006Search in Google Scholar

Dallas C, Gerbi A, Elbez Y, Caillard P, Zamaria N, Cloarec M. Clinical study to assess the efficacy and safety of a citrus polyphenolic extract of red orange, grapefruit, and orange (Sinetrol-XPur) on weight management and metabolic parameters in healthy overweight individuals. Phytother Res 2014; 28: 212–218.10.1002/ptr.4981Search in Google Scholar

Del Río JA, Fuster MD, Gómez P, Porras I, García-Lidón A, Ortuño A. Citrus limon: a source of flavonoids of pharmaceutical interest. Food Chem 2004; 84: 457–461.10.1016/S0308-8146(03)00272-3Search in Google Scholar

Di Donna L, Taverna D, Mazzotti F, Benabdelkamel H, Attya M, Napoli A, Sindona G. Comprehensive assay of flavanones in citrus juices and beverages by UHPLC-ESI-MS/MS and derivatization chemistry. Food Chem 2013; 141: 2328–2333.10.1016/j.foodchem.2013.05.034Search in Google Scholar

Di Majo D, Giammanco M, La Guardia M, Tripoli E, Giammanco S, Finotti E. Flavanones in citrus fruit: structure-antioxidant activity relationships. Food Res Int 2005; 38: 1161–1166.10.1016/j.foodres.2005.05.001Search in Google Scholar

Dow CA, Going SB, Chow HH, Patil BS, Thomson CA. The effects of daily consumption of grapefruit on body weight, lipids, and blood pressure in healthy, overweight adults. Metabolomics 2012; 61: 1026–1035.10.1016/j.metabol.2011.12.004Search in Google Scholar

Dunn, Warwick B, Erban A, Weber RJM, Creek DJ, Brown M, Breitling R, Hankemeier T. Mass appeal: metabolite identification in mass spectrometry-focused untargeted metabolomics. Metabolomics 2013; 9: 44–66.10.1007/s11306-012-0434-4Search in Google Scholar

Exarchou V, Krucker M, van Beek TA, Vervoort J, Gerothanassis IP, Albert K. LC NMR coupling technology: recent advancements and applications in natural products analysis. Magn Reson Chem 2005; 43: 681–687.10.1002/mrc.1632Search in Google Scholar

Fabre N, Rustan I, de Hoffmann E, Quetin-Leclercq J. Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry. J Am Soc Mass Spectro 2001; 12: 707–715.10.1016/S1044-0305(01)00226-4Search in Google Scholar

Ferhat MA, Meklati BY, Chemat F. Comparison of different isolation methods of essential oil from citrus fruits: cold pressing, hydrodistillation and microwave ‘dry’ distillation. Flavour Frag J 2007; 22: 494−504.10.1002/ffj.1829Search in Google Scholar

Ferreres F, Llorach R, Gil-Izquierdo A. Characterization of the interglycosidic linkage in di-, tri-, tetra- and pentaglycosylated flavonoids and differentiation of positional isomers by liquid chromatography/electrospray ionization tandem mass spectrometry. J Mass Spectrosc 2004; 39: 312–321.10.1002/jms.586Search in Google Scholar

Garcia S, Heinzen H, Martinez R, Moyna P. Identification of flavonoids by TLC scanning analysis. Chromatographia 1993; 35: 430–434.10.1007/BF02278597Search in Google Scholar

Gattuso G, Barreca D, Gargiulli C, Leuzzi U, Caristi C. Flavonoid composition of citrus juices. Molecules 2007; 12: 1641–1673.10.3390/12081641Search in Google Scholar

Gionfriddo F, Postorino E, Bovalo F. I flavanone glucosidicinelsucco di bergamotto. Essenze-Derivatiagrumari 1996; 66: 404–416.Search in Google Scholar

González-Molina E, Domínguez-Perles R, Moreno DA, García-Viguera C. Natural bioactive compounds of Citrus limon for food and health. J Pharm Biol Anal 2010; 51: 327−345.10.1016/j.jpba.2009.07.027Search in Google Scholar

Greenham J, Williams C, Harborne JB. Identification of lipophilic flavonols by a combination of chromatographic and spectral techniques. Phytochem Anal 1995; 6: 211.10.1002/pca.2800060407Search in Google Scholar

Guimaraes R, Barros L, Barreira JCM, Sousa MJ, Carvalho AM, Ferreira ICFR. Targeting excessive free radicals with peels and juices of citrus fruits: grapefruit, lemon, lime and orange. Food Chem Toxicol 2010; 48: 99–106.10.1016/j.fct.2009.09.022Search in Google Scholar

Harborne JB, Boardley M. Use of high-performance liquid chromatography in the separation of flavonol glycosides and flavonol sulphates. J Chromatogr A 1984; 299: 377.10.1016/S0021-9673(01)97853-7Search in Google Scholar

He XG, Lian LZ, Lin LZ, Bernart MW. High-performance liquid chromatography-electrospray mass spectrometry in phytochemical analysis of sour orange (Citrus aurantium L.). J Chromatogr A 1997; 791: 127–134.10.1016/S0021-9673(97)00779-6Search in Google Scholar

Heim KE, Tagliaferro AR, Bobilya DJ. Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J Nutr Biochem 2002; 13: 572–584.10.1016/S0955-2863(02)00208-5Search in Google Scholar

Horowitz RM, Gentili B. Dihydrochalcone sweeteners from citrus flavanones. In: O’Brien-Nabors L, Gelardi RC, editors. Alternative sweeteners. New York: Marcel Dekker, 1979: 135–153.Search in Google Scholar

Huong DTT, Takahashi Y, Ide T. Activity and mRNA levels of enzymes involved in hepatic fatty acid oxidation in mice fed citrus flavonoids. Nutrition 2006; 22: 546–552.10.1016/j.nut.2005.11.006Search in Google Scholar PubMed

Hvattum E. Determination of phenolic compounds in rose hip (Rosa canina) using liquid chromatography coupled to electrospray ionisation tandem mass spectrometry and diode-array detection. Rapid Commun Mass Spectrom 2002; 16: 655–662.10.1002/rcm.622Search in Google Scholar

Ishiwa J, Sato T, Mimaki Y, Sahida Y, Yano M, Ito AA. Citrus flavonoid, nobiletin, suppress production and gene expression of matrix metalloproteinase 9/gelatinase B in rabbit synovial fibroblasts. J Rheumatol 2000; 271: 20–25.Search in Google Scholar

Johnston K, Sharp P, Clifford M, Morgan L. Dietary polyphenols decrease glucose uptake by human intestinal Caco-2 cells. FEBS Letters 2005; 579: 1653–1657.10.1016/j.febslet.2004.12.099Search in Google Scholar

Jung UJ, Kim HJ, Lee JS, Lee MK, Kim HO, Park EJ, Choi MS. Naringin supplementation lowers plasma lipids and enhances erythrocyte antioxidant enzyme activities in hypercholesterolemic subjects. Clin Nutr 2003; 22: 561–568.10.1016/S0261-5614(03)00059-1Search in Google Scholar

Karas M, Bachmann D, Bahr U, Hillenkamp F. Matrix assisted ultraviolet laser desorption of nonvolatile compounds. Int J Mass Spectrom Ion Processes 1987; 78: 53–68.10.1016/0168-1176(87)87041-6Search in Google Scholar

Kawahata I, Yoshida M, Sun W, Nakajima A, Lai Y, Osaka N, Matsuzaki K. Potent activity of nobiletin-rich citrus reticulata peel extract to facilitate cAMP/PKA/ERK/CREB signaling associated with learning and memory in cultured hippocampal neurons: identification of the substances responsible for the pharmacological action. J Neural Transm 2013; 120: 1397–1409.10.1007/s00702-013-1025-xSearch in Google Scholar

Kawaii S, Tomono Y, Katase E, Ogawa K, Masamichi YANO. Antiproliferative activity of flavonoids on several cancer cell lines. Biosci Biotech Biochem 1999; 63: 896–899.10.1271/bbb.63.896Search in Google Scholar

Khan MK, Abert-Vian M, Fabiano-Tixier AS, Dangles O, Chemat F. Ultrasound-assisted extraction of polyphenols (flavanone glycosides) from orange (Citrus sinensis L.) peel. Food Chem 2010; 119: 851–858.10.1016/j.foodchem.2009.08.046Search in Google Scholar

Khokhar S, Magnusdottir SGM. Total phenol, catechin, and caffeine contents of teas commonly consumed in the United Kingdom. J Agric Food Chem 2002; 50: 565–570.10.1021/jf010153lSearch in Google Scholar

Kim HK, Jeong TS, Lee MK, Park YB, Choi MS. Lipid-lowering efficacy of hesperetin metabolites in high-cholesterol fed rats. Clin Chim Acta 2003; 327: 129–137.10.1016/S0009-8981(02)00344-3Search in Google Scholar

Kim SY, Kim HJ, Lee MK, Jeon SM, Do GM, Kwon EY, Cho YY. Naringin time-dependently lowers hepatic cholesterol biosynthesis and plasma cholesterol in rats fed high-fat and high-cholesterol diet. J Med Food 2006; 9: 582–586.10.1089/jmf.2006.9.582Search in Google Scholar PubMed

Kim JW, Nagaoka T, Ishida Y, Hasegawa T, Kitagawa K, Lee SC. Subcritical water extraction of nutraceutical compounds from citrus pomaces. Sep Sci Technol 2009; 44: 2598–2608.10.1080/01496390903014375Search in Google Scholar

Kim GN, Shin MR, Shin SH, Lee AR, Lee JY, Bu-Il S, Kim M, Kim TH, Noh JS, Rhee MH, Roh SS. Study of antiobesity effect through inhibition of pancreatic lipase activity of Diospyros kaki fruit and Citrus unshiu peel. BioMed Res Int 2016; 2016: 1723042.10.1155/2016/1723042Search in Google Scholar

Kumar KA, Narayani M, Subanthini A, Jayakumar M. Antimicrobial activity and phytochemical analysis of citrus fruit peels – utilization of fruit waste. Int J Eng Sci Technol 2011; 3: 5414–5421.Search in Google Scholar

Labarbe B, Cheynier V, Brossaud F, Souquet JM, Moutounet M. Quantitative fractionation of grape proanthocyanidins according to their degree of polymerization. J Agric Food Chem 1999; 47: 2719–2723.10.1021/jf990029qSearch in Google Scholar

Lee SH, Park YB, Bae KH, Bok SH, Kwon YK. Cholesterol-lowering activity of naringenin via inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase and acyl coenzyme A: cholesterol acyltransferase in rats. Ann Nutr Metab 1999; 43: 173–180.10.1159/000012783Search in Google Scholar

Lee JJ, Yi H, Kim IS, Kim Y, Nhiem NX, Kim YH, Myung CS. (2S)-Naringenin from Typha angustata inhibits vascular smooth muscle cell proliferation via a G 0/G 1 arrest. J Ethnopharmacol 2012; 139: 873–878.10.1016/j.jep.2011.12.038Search in Google Scholar

Lee J, Yang DS, Han SI, Yun JH, Kim Iw, Kim SJ, Kim JH. Aqueous extraction of Citrus unshiu peel induces proangiogenic effects through the FAK and ERK1/2 signaling pathway in human umbilical vein endothelial cells. J Med Food 2016; 19: 569–577.10.1089/jmf.2015.3584Search in Google Scholar

Lewinsohn E, Berman E, Mazur Y, Gressel J. (7)-Glucosylation and (1–6) rhamnosylation of exogenous flavanones by undifferentiated Citrus cell cultures. Plant Sci 1989; 61: 23–28.10.1016/0168-9452(89)90114-3Search in Google Scholar

Li WK, Fong HHS, Singletary KW, Fitzloff JF. Determination of catechins in commercial grape seed extract. J Liq Chromatogr R T 2002; 25: 397–407.10.1081/JLC-120008754Search in Google Scholar

Lim DW, Lee Y, Kim YT. Preventive effects of Citrus unshiu peel extracts on bone and lipid metabolism in OVX rats. Molecules 2014; 19: 783–794.10.3390/molecules19010783Search in Google Scholar PubMed PubMed Central

Lommen A, Godejohann M, Venema DP, Hollman PCH, Spraul M. Application of directly coupled HPLC-NMR-MS to the identification and confirmation of quercetin glycosides and phloretin glycosides in apple peel. Anal Chem 2000; 72: 1793.10.1021/ac9912303Search in Google Scholar PubMed

Londoño-Londoño J, Lima VRd, Lara O, Gil A, Pasa TBC, Arango GJ, Pineda JRR. Clean recovery of antioxidant flavonoids from citrus peel: optimizing an aqueous ultrasound-assisted extraction method. Food Chem 2010; 119: 81–87.10.1016/j.foodchem.2009.05.075Search in Google Scholar

Ma YL, Vedernikova I, Van den Heuvel H, Claeys M. Internal glucose residue loss in protonated O-diglycosyl flavonoids upon low-energy collision-induced dissociation. J Am Soc Mass Spectro 2000; 11: 136–144.10.1016/S1044-0305(99)00133-6Search in Google Scholar

Mabry TJ, Markham KR, Thomas MB. The ultraviolet spectra of flavones and flavonols. In: The systematic identification of flavonoids. Berlin: Spinger-Verlag, 1970: 35–40.10.1007/978-3-642-88458-0_4Search in Google Scholar

Macheix JJ, Fleuriet A, Billot J. The main phenolics of fruits. In: Fruit phenolics. CRC Press: Boca Raton, FL, 1990: 1–103.Search in Google Scholar

Mahato N, Sharma K, Nabybaccus F. Citrus waste reuse for health benefits and pharma-/neutraceutical applications. Era’s J Med Res 2017; 3: 20–32.Search in Google Scholar

Manach C, Morand C, Gil-Izquierdo A. Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice. Eur J Clin Nutr 2003; 57: 235–242.10.1038/sj.ejcn.1601547Search in Google Scholar

Manthey JA, Guthrie N, Grohmann K. Biological properties of citrus flavonoids pertaining to cancer and inflammation. Current Med Chem 2001; 8: 135−153.10.2174/0929867013373723Search in Google Scholar

McIntosh CA, Latchinian L, Mansell RL. Flavanone specific 7-O glucosyltransferase activity in Citrus paradise seedlings: purification and characterization. Arch Biochem Biophys 1990; 282: 50–57.10.1016/0003-9861(90)90085-DSearch in Google Scholar

Mencherini T, Campone L, Piccinelli AL. HPLC-PDA-MS and NMR characterization of a hydroalcoholic extract of Citrus aurantium L. var. amara peel with antiedematogenic activity. J Agric Food Chem 2013; 61: 1686–1693.10.1021/jf302815tSearch in Google Scholar PubMed

Merken HM, Beecher GR. Measurement of food flavonoids by high-performance liquid chromatography: a review. J Agric Food Chem 2000; 48: 577–599.10.1021/jf990872oSearch in Google Scholar PubMed

Miyake Y, Hiramitsu M. Isolation and extraction of antimicrobial substances against oral bacteria from lemon peel. J Food Sci Technol 2011; 48: 635–639.10.1007/s13197-011-0330-3Search in Google Scholar PubMed PubMed Central

Morand C, Dubray C, Milenkovic D, Lioger D, Martin JF, Scalbert A, Mazur A. Hesperidin contributes to the vascular protective effects of orange juice: a randomized crossover study in healthy volunteers. Am J Clin Nutr 2011; 93: 73–80.10.3945/ajcn.110.004945Search in Google Scholar PubMed

Moriguchi T, Kita M, Tomono Y, Endo-Inaguki T, Omura M. Gene expression in flavonoid biosynthesis: correlation with flavonoid accumulation in developing citrus fruit. Physiol Plant 2001; 114: 251–258.10.1034/j.1399-3054.2001.1110109.xSearch in Google Scholar

Mulvihill EE, Huff MW. Antiatherogenic properties of flavonoids: implications for cardiovascular health. Can J Cardio 2010; 26(Suppl. A): 17–21A.10.1016/S0828-282X(10)71056-4Search in Google Scholar

Mulvihill EE, Assini JM, Lee JK, Allister EM, Sutherland BG. Nobiletin attenuates VLDL overproduction, dyslipidemia, and atherosclerosis in mice with diet-induced insulin resistance. Diabetes 2011; 60: 1446–1457.10.2337/db10-0589Search in Google Scholar

Nafisi-Movaghar K, Druz LL, Victoria CP. US8481099 B2, 2013.Search in Google Scholar

Nagaraju B, Anand SC, Ahmed N, Chandra JNS, Ahmed F, Padmavathi GV. Antiulcer activity of aqueous extract of Citrus medicalinn fruit against ethanol induced ulcer in rats. Adv Bio Res 2012; 6: 24–29.Search in Google Scholar

Neergheen VS, Soobrattee MA, Bahorun T, Aruoma OI. Characterization of the phenolic constituents in Mauritian endemic plants as determinants of their antioxidant activities in vitro. J Plant Physiol 2006; 163: 787–799.10.1016/j.jplph.2005.09.009Search in Google Scholar

Nishimura T, Kometani T, Okada S, Kobayashi Y, Fukumoto S. Inhibitory effects of hesperidin glycosides on precipitation of hesperidin. J Jpn Soc Food Sci Technol 1998; 45: 186–191.10.3136/nskkk.45.186Search in Google Scholar

Okuyama S, Yamamoto K, Mori H, Toyoda N, Yoshimura M, Amakura Y, Yoshida T. Auraptene in the peels of Citrus kawachiensis (KawachiBankan) ameliorates lipopolysaccharide-induced inflammation in the mouse brain. J Evidence Based Complem Alternat Med 2014; 2014, Article ID 408503, 0 to 9 pages.10.1155/2014/408503Search in Google Scholar

Pantsulaia I, Iobadze M, Pantsulaia N, Chikovani T. The effect of citrus peel extracts on cytokines levels and T regulatory cells in acute liver injury. BioMed Res Int 2014; 2014, Article ID 127879, 0 to 7 pages.10.1155/2014/127879Search in Google Scholar

Pauli GF, Jaki BU, Lankin DC. Quantitative 1H NMR: development and potential of a method for natural products analysis. J Nat Prod 2005; 68: 133–149.10.1021/np0497301Search in Google Scholar

Penazzi G, Caboni MF, Zunin P, Evangelisti F, Tiscornia E, Toschi TG, Lercker G. Routine high-performance liquid chromatographic determination of free 7-ketocholesterol in some foods by two different analytical methods. J Am Oil Chem Soc 1995; 72: 1523–1527.10.1007/BF02577847Search in Google Scholar

Peter E, Peter J, Nes B, Asukwo G. Physicochemical properties and fungitoxicity of the essential. Turk J Bot 2008; 32: 161–164.Search in Google Scholar

Peterson J, Dwyer J. Flavonoids: dietary occurrence and biochemical activity. Nutr Res 1998; 18: 1995–2018.10.1016/S0271-5317(98)00169-9Search in Google Scholar

Piccinelli AL, García Mesa M, Armenteros DM, Alfonso MA, Arevalo AC, Campone L, Rastrelli L. HPLC-PDA-MS and NMR characterization of C-glycosyl flavones in a hydroalcoholic extract of Citrus aurantifolia leaves with antiplatelet activity. J Agric Food Chem 2008; 56: 1574–1581.10.1021/jf073485kSearch in Google Scholar

Prasain JK, Barnes S. Metabolism and bioavailability of flavonoids in chemoprevention: current analytical strategies and future prospectus. Mol Pharma 2007; 4: 846–864.10.1021/mp700116uSearch in Google Scholar

Ramirez-Coronel MA, Marnet N, Kolli VS, Roussos S, Guyot S, Augur C. Characterization and estimation of proanthocyanidins and other phenolics in coffee pulp (Coffeaarabica) by thiolysis-high-performance liquid chromatography. J Agric Food Chem 2004; 52: 1344–1349.10.1021/jf035208tSearch in Google Scholar

Ranganna S, Govindarajan VS, Ramana KV. Citrus fruits. Part II. Chemistry, technology, and quality evaluation. B. Technology. Crit Rev Food Sci Nutr 1983; 19: 1–98.10.1080/10408398309527369Search in Google Scholar

Raymond WR, Maier VP. Chalcone cyclase and flavonoidbiosynthesis in grapefruit. Phytochemistry 1977; 16: 1535–1539.10.1016/0031-9422(77)84018-1Search in Google Scholar

Robards K, Li X, Antolovich M, Boyd S. Characterisation of citrus by chromatographic analysis of flavonoids. J Sci Food Agric 1997; 75: 87–101.10.1002/(SICI)1097-0010(199709)75:1<87::AID-JSFA846>3.0.CO;2-BSearch in Google Scholar

Roowi S, Crozier A. Flavonoids in tropical citrus species. J Agric Food Chem 2011; 59: 12217–12225.10.1021/jf203022fSearch in Google Scholar

Sägesser M, Deinzer M. HPLC-ion spray-tandem mass spectrometry of flavonol glycosides in hops. J Am Soc Brew Chem 1996; 54: 129.10.1094/ASBCJ-54-0129Search in Google Scholar

Saalu LC, Ajayi GO, Adeneye AA, Imosemi IO, Osinubi AA. Ethanolic seed extract of grapefruit (Citrus paradisi Macfad). Int J Cancer Res 2009; 5: 44–52.10.3923/ijcr.2009.44.52Search in Google Scholar

Salerno R, Casale F, Calandruccio C, Procopio A. Characterization of flavonoids in Citrus bergamia (Bergamot) polyphenolic fraction by liquid chromatography-high resolution mass spectrometry (LC/HRMS). Pharma Nutr 2016; 4: S1–S7.10.1016/j.phanu.2015.10.001Search in Google Scholar

Schieber A, Keller P, Streker P, Klaiber I, Carle R. Detection of isorhamnetin glycosides in extracts of apples (Malus domestica cv. ‘Brettacher’) by HPLC-PDA and HPLC-APCI-MS/MS. Phytochem Anal 2002; 13: 87.10.1002/pca.630Search in Google Scholar

Shan Y. Comprehensive utilization of citrus by-products. Academic Press, Elsevier: London, UK, 2016.Search in Google Scholar

Sharma K, Mahato N, Cho MH, Lee YR. Converting citrus wastes into value-added products: economic and environmentally friendly approaches. Nutrition 2017; 34: 29–46.10.1016/j.nut.2016.09.006Search in Google Scholar

Shetty SB, Mahin-Syed-Ismail P, Thomas-George B, Varghese S, Kandathil-Thajuraj P, Baby D, Haleem S, Sreedhar S, Darshan Devang-Divakar D. Antimicrobial effects of Citrus sinensis peel extracts against dental caries bacteria: an in vitro study. J Clin Exp Dent 2016; 8: e71–e77.10.4317/jced.52493Search in Google Scholar

Shin YW, Bok SH, Jeong TS, Bae KH, Jeoung NH, Choi MS, Lee SH, Park YB. Hypocholesterolemic effect of naringin associated with hepatic cholesterol regulating enzyme changes in rats. Int J Vitam Nutr Res 1999; 69: 341–347.10.1024/0300-9831.69.5.341Search in Google Scholar

Sommer H, Bertram HJ, Krammer G, Kindel G, Kuhnle T, Reinders G, Reiss I, Schmidt CO, Schreiber K, Stumpe W, Werkhoff P. HPLC-NMR – a powerful tool for the identification of non-volatiles in lemon peel oils. Perfume Flavoure 2003; 28: 18–34.Search in Google Scholar

Sood S, Bansal S, Muthuraman A, Gill NS, Bali M. Therapeutic potential of Citrus medica L. peel extract in carrageenan induced inflammatory pain in rat. Res J Med Plant 2009; 3: 123–133.10.3923/rjmp.2009.123.133Search in Google Scholar

Sood S, Muthuraman A, Gill NS, Bali M, Sharma PD. Effect of Citrus karna peel extract on stress induced peptic ulcer in rat. J Biol Sci 2010; 10: 231–236.10.3923/jbs.2010.231.236Search in Google Scholar

Spigno G, Faveri DMD. Microwave-assisted extraction of tea phenols: a phenomenological study. J Food Eng 2009; 93: 210–217.10.1016/j.jfoodeng.2009.01.006Search in Google Scholar

Sridharan B, Shiju MT, Arya R, Roopan SM, Ganesh RN, Viswanathan P. Beneficial effect of Citrus limon peel aqueous methanol extract on experimentally induced urolithic rats. Pharma Biol 2016; 54: 759–769.10.3109/13880209.2015.1079724Search in Google Scholar

Stavric B. Antimutagens and anticarcinogens in foods. Food Chem Toxicol 1994; 32: 79–90.10.1016/0278-6915(84)90040-1Search in Google Scholar

Stobiecki M. Application of mass spectrometry for identification and structural studies of flavonoid glycosides. Phytochemistry 2000; 54: 237–256.10.1016/S0031-9422(00)00091-1Search in Google Scholar

Sun Y, Wang J, Gu S, Liu Z, Zhang Y, Zhang X. Simultaneous determination of flavonoids in different parts of Citrus reticulata ‘Chachi’ fruit by high performance liquid chromatography-photodiode array detection. Molecules 2010; 15: 5378–5388.10.3390/molecules15085378Search in Google Scholar PubMed PubMed Central

Suzawa M, Guo L, Pan MH, Ho CT, Li S. In vivo anti-carcinogenic property of a formulated citrus peel extract. Funct Food Health Dis 2014; 4: 120–129.10.31989/ffhd.v4i3.21Search in Google Scholar

Tanaka T, Makita H, Kawabata K, Mori H, Kakumoto M, Satoh K, Ogawa H. Chemoprevention of azoxymethane-induced rat colon carcinogenesis by the naturally occurring flavonoids, diosmin and hesperidin. Carcinogenesis 1997; 18: 957–965.10.1093/carcin/18.5.957Search in Google Scholar PubMed

Thimothe J, Bonsi IA, Padilla-Zakour OI, Koo H. Chemical characterization of red wine grape (Vitis vinifera and Vitis interspecific hybrids) and pomace phenolic extracts and their biological activity against Streptococcus mutans. J Agric Food Chem 2007; 55: 10200–10207.10.1021/jf0722405Search in Google Scholar PubMed

Tokunaga H, Seiwa C, Yoshioka N, Mizoguchi K, Yamamoto M, Asou H, Aiso S. An extract of chinpi, the dried peel of the Citrus fruit unshiu, enhances axonal remyelination via promoting the proliferation of oligodendrocyte progenitor cells. Evidence Based Complem Altern Med 2016; 2016, Article ID 8692698, 0 to 9 pages.10.1155/2016/8692698Search in Google Scholar PubMed PubMed Central

Tripoli E, La Guardia M, Giammanco S, Di Majo D, Giammanco M. Citrus flavonoids: molecular structure, biological activity and nutritional properties: a review. Food Chem 2007; 104: 466–479.10.1016/j.foodchem.2006.11.054Search in Google Scholar

Vinita D, Apraj N, Pandita S. Evaluation of skin antiaging potential of Citrus reticulatablanco peel. Pharmacognosy Res 2016; 8: 160–168.10.4103/0974-8490.182913Search in Google Scholar PubMed PubMed Central

Xu BJ, Chang SK. A comparative study on phenolic profiles and antioxidant activities of legumes as affected by extraction solvents. J Food Sci 2007; 72: S159–S166.10.1111/j.1750-3841.2006.00260.xSearch in Google Scholar PubMed

Zhang Y, Seeram NP, Lee R, Feng L, Heber D. Isolation and identification of strawberry phenolics with antioxidant and human cancer cell antiproliferative properties. J Agric Food Chem 2008; 56: 670–675.10.1021/jf071989cSearch in Google Scholar PubMed

Zheng G, Yang D, Wang D, Zhou F, Yang X, Jiang L. Simultaneous determination of five bioactive flavonoids in pericarpium Citri reticulatae from china by high-performance liquid chromatography with dual wavelength detection. J Agric Food Chem 2009; 57: 6552–6557.10.1021/jf901225eSearch in Google Scholar PubMed

Received: 2017-04-27
Accepted: 2017-10-26
Published Online: 2018-01-08
Published in Print: 2019-02-25

©2019 Walter de Gruyter GmbH, Berlin/Boston

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