Flavones

Hădărugă, Daniel-Ioan; Hădărugă, Nicoleta-Gabriela

doi:10.1007/978-3-030-81404-5_4-1

Daniel-Ioan Hădărugă⁴ &
Nicoleta-Gabriela Hădărugă⁵

50 Accesses

Abstract

This chapter is dedicated to the natural antioxidants having 2-phenyl-4H-1-benzopyran-4-one skeleton and hydroxyl groups on the aromatic rings only. The main physical-chemical and biological properties, as well as the natural occurrence and food applications of the main flavones, are discussed. The chemistry and functionality of the main compounds from this class allow identifying their biological activities and their further applications. This part is focused on chrysin, apigenin, acacetin, baicalein, luteolin, diosmetin, scutellarein, hispidulin, tricetin, sinensetin, tangeretin, serpyllin, nobiletin, and scaposin. However, the number of flavone compounds with pharmaceutical and food applications is much higher than this list. Correlations between structural characteristics and properties of flavones have also been presented in this chapter. We have focused on the main groups responsible for many biological and antioxidant activities and properties related to flavone bioavailability. Thus, phenolic hydroxyl groups and solubility parameters were considered. On the other hand, molecular surface accessibility, oxidation susceptibility, and antioxidant mechanisms were discussed. The biosynthesis of the main flavone compounds and enhancing their enzymatic production for industrial purposes are also presented in this chapter. A significant part of this chapter is dedicated to the identification and quantification of flavone aglycones and glycosides in plants, vegetables, fruits, grains, and foods, as well as their interactions with food ingredients and matrices, production, and applications in food products. The separation and purification techniques and modern analytical methods used for flavone evaluation were surveyed, pointing out the most recent studies in the field. Finally, conclusions and future perspectives related to flavone research, especially their applications in food and pharmaceutical fields, have been presented.

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Abbreviations

¹H/¹³C-NMR:: ¹H/¹³C-nuclear magnetic resonance
ABTS·⁺:: 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation
CD:: Circular dichroism
CFI:: Chalcone-flavanone isomerase
CHS:: Chalcone synthase
CoA:: Coenzyme A
COVID-19:: Coronavirus disease 2019
CUPRAC:: Cupric reducing antioxidant capacity
DPPH·:: 2,2-diphenyl-1-pycrylhydrazyl radical
DW:: Dry weight
EC:: Enzyme Commission numbers
EC₅₀:: Half maximal effective concentration
Ecugd:: Uridine diphosphate glucose dehydrogenase from Escherichia coli
EI/ESI-MS:: Electrospray ionization-mass spectrometry
F3′5′H:: Flavonoid 3′,5′-hydroxylase
FAB-MS:: Fast atom bombardment-mass spectrometry
FAME:: Fatty acid methyl ester
FRAP:: Ferric reducing antioxidant power
FS:: Flavone synthase
FT-IR:: Fourier transform infrared spectroscopy
FW:: Fresh weight
GAE:: Gallic acid equivalent
GC-FID/MS:: Gas chromatography coupled with flame ionization detector/mass spectrometry detector
GEArray:: Gene expression profiles of 96 genes indicative of mouse stress and toxicity
GmSUS:: Glycine max sucrose synthase
Gpx:: Glutathione peroxidase
HAT:: H-atom transfer
HHP:: High hydrostatic pressure
HOMO:: Highest occupied molecular orbital
HPLC-UV-Vis/DAD/MS:: High-pressure liquid chromatography coupled with ultraviolet-visible spectrophotometric detector/diode array detector/mass spectrometry detector
HPLC-MS/MS/MSⁿ/MRM-MS:: Liquid chromatography coupled with tandem mass spectrometry (MS/MS or MSⁿ)/ multiple reaction monitoring-mass spectrometry detector
HP-TLC:: High-performance thin layer chromatography
HSA:: Human serum albumin
iNOS:: Inducible nitric oxide synthase
IR:: Infrared spectroscopy
IUBMB:: Nomenclature Committee of the International Union of Biochemistry and Molecular Biology
LC-CE-MS:: Liquid chromatography-capillary electrophoresis-mass spectrometry
LC-ESI-MS:: Liquid chromatography coupled with electrospray ionization – mass spectrometry detector
LC-HRMS:: Liquid chromatography coupled with high-resolution mass spectrometry detector
LDL:: Low-density lipoprotein
LPO:: Lipid peroxidation
LUMO:: Lowest unoccupied molecular orbital
MAE:: Microwave-assisted extraction
MsCHI:: Chalcone isomerase from Medicago sativa
MTT:: 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide
NADP⁺/NADPH:: Nicotinamide adenine dinucleotide phosphate/reduced form
ObFOMT:: Ocimum basilicum L. flavonoid O-methyltransferase
OMT:: O-methyltransferase
ORAC:: Oxygen radical absorbance capacity
PcFNS I:: Flavone synthase I from Petroselinum crispum
pE-AmUGT10:: pET gene + uridine diphosphate-dependent glycosyltransferase specific for UDP-glucuronic acid from Antirrhinum majus
PhCHS:: Chalcone synthase from Petunia X hybrid
PLA:: Poly(lactide)
PLE:: Pressurized liquid extraction
QE:: Quercetin equivalent
rpm:: Revolutions per minute
RSC:: Radical scavenging capacity
SARS-CoV-2:: Severe acute respiratory syndrome coronavirus 2
SbFNS II:: Flavone synthase II from Scutellaria baicalensis
SbF6H:: Flavone 6-hydroxylase from S. baicalensis
SEM:: Scanning electron microscopy
SET-PT:: Single electron transfer-proton transfer
SPE:: Solid-phase extraction
SPLET:: Sequential proton loss electron transfer
SPME:: Solid-phase microextraction
SOD:: Superoxide dismutase
TaOMT2:: Triticum aestivum L. O-methyltransferase (recombinant)
TBARS:: Thiobarbituric acid reactive substances
TcCGT:: Trollius chinensis C-glycosyltransferase
TEM:: Transmission electron microscopy
TLC:: Thin layer chromatography
TPC:: Total phenolic content
TRP:: Total reducing power
UAE:: Ultrasound-assisted extraction
UAPLE:: Ultrasound-assisted pressurized liquid extraction
UDP-Glu:: Uridine diphosphate glucose
UDP-GT:: Uridine diphosphate glucuronotransferase
UHPLC-MS/MS:: Ultrahigh-pressure liquid chromatography coupled with tandem mass spectrometry detector
UPLC-PDA-ESI/QTOF-MS/MS²:: Ultrahigh-pressure liquid chromatography coupled with photodiode array detector and electrospray ionization/quadrupole time-of-flight-mass spectrometry/tandem mass spectrometry detector
UPLC-QE-HRMS:: Ultrahigh-performance liquid chromatography-high-resolution mass spectrometry detector
UV-Vis:: Ultraviolet-visible spectrophotometry
XRD:: X-ray diffractometry

References

Abbasi-Parizad P, De-Nisi P, Sciarria TP, et al. Polyphenol bioactivity evolution during the spontaneous fermentation of vegetal by-products. Food Chem. 2022;374:131791. https://doi.org/10.1016/j.foodchem.2021.131791.
Article CAS Google Scholar
Abcha I, Souilem S, Neves MA, et al. Ethyl oleate food-grade O/W emulsions loaded with apigenin: insights to their formulation characteristics and physico-chemical stability. Food Res Int. 2019;116:953–62. https://doi.org/10.1016/j.foodres.2018.09.032.
Article CAS Google Scholar
Abdelhady MIS, Motaal AA. A cytotoxic C-glycosylated derivative of apigenin from the leaves of Ocimum basilicum var. thyrsiflorum. Rev Bras Farmacogn. 2016;26:763–6. https://doi.org/10.1016/j.bjp.2016.06.004.
Article CAS Google Scholar
Aziz AHA, Putra NR, Kong H, et al. Supercritical carbon dioxide extraction of sinensetin, isosinensetin, and rosmarinic acid from Orthosiphon stamineus leaves: optimization and modeling. Arabian J Sci Eng. 2020;45:7467–76. https://doi.org/10.1007/s13369-020-04584-6.
Article CAS Google Scholar
Berim A, Gang DR. Methoxylated flavones: occurrence, importance, biosynthesis. Phytochem Rev. 2016;15:363–90. https://doi.org/10.1007/s11101-015-9426-0.
Article CAS Google Scholar
Bi F, Qin Y, Chen D, et al. Development of active packaging films based on chitosan and nano-encapsulated luteolin. Int J Biol Macromol. 2021;182:545–53. https://doi.org/10.1016/j.ijbiomac.2021.04.063.
Article CAS Google Scholar
Biesaga M. Influence of extraction methods on stability of flavonoids. J Chromatogr A. 2011;1218:2505–12. https://doi.org/10.1016/j.chroma.2011.02.059.
Article CAS Google Scholar
Bors W, Heller W, Michel C, et al. Structural Principles of Flavonoid Antioxidants. In: Csomós G, Fehér J, editors. Free Radical Liver. Berlin: Springer-Verlag; 1992. p. 77–95. https://doi.org/10.1007/978-3-642-76874-3.
Chapter Google Scholar
Bradwell J, Hurd M, Pangloli P, et al. Storage stability of sorghum phenolic extractsʼ flavones luteolin and apigenin. LWT – Food Sci Technol. 2018;97:787–93. https://doi.org/10.1016/j.lwt.2018.08.006.
Article CAS Google Scholar
Brauch D, Porzel A, Schumann E, et al. Changes in isovitexin-O-glycosylation during the development of young barley plants. Phytochemistry. 2018;148:11–20. https://doi.org/10.1016/j.phytochem.2018.01.001.
Article CAS Google Scholar
Cattaneo F, Costamagna MS, Zampini IC, et al. Flour from Prosopis alba cotyledons: a natural source of nutrient and bioactive phytochemicals. Food Chem. 2016;208:89–96. https://doi.org/10.1016/j.foodchem.2016.03.115.
Article CAS Google Scholar
Chaaban H, Ioannou I, Paris C, et al. The photostability of flavanones, flavonols and flavones and evolution of their antioxidant activity. J Photochem Photobiol A. 2017;336:131–9. https://doi.org/10.1016/j.jphotochem.2016.12.027.
Article CAS Google Scholar
Chen F, Zhang Q, Mo K, et al. Optimization of ionic liquid-based homogenate extraction of orientin and vitexin from the flowers of Trollius chinensis and its application on a pilot scale. Sep Purif Technol. 2017;175:147–57. https://doi.org/10.1016/j.seppur.2016.10.062.
Article CAS Google Scholar
Coetzee G, Joubert E, van-Zyl WH, et al. Improved extraction of phytochemicals from rooibos with enzyme treatment. Food Bioprod Process. 2014;92:393–401. https://doi.org/10.1016/j.fbp.2013.08.013.
Article CAS Google Scholar
Coneac G, Gafiţanu E, Hădărugă DI, et al. Propolis extract/β-cyclodextrin nanoparticles: synthesis, physico-chemical, and multivariate analyses. J Agroaliment Process Technol. 2008;14(1):58–70.
CAS Google Scholar
Deshmukh AB, Datir SS, Bhonde Y, et al. De novo root transcriptome of a medicinally important rare tree Oroxylum indicum for characterization of the flavonoid biosynthesis pathway. Phytochemistry. 2018;156:201–13. https://doi.org/10.1016/j.phytochem.2018.09.013.
Article CAS Google Scholar
Dong R, Li L, Gao H, et al. Safety, tolerability, pharmacokinetics, and food effect of baicalein tablets in healthy Chinese subjects: a single-center, randomized, double-blind, placebo-controlled, single-dose phase I study. J Ethnopharmacol. 2021;274:114052. https://doi.org/10.1016/j.jep.2021.114052.
Article CAS Google Scholar
Duarte-Almeida JM, Negri G, Salatino A, et al. Antiproliferative and antioxidant activities of a tricin acylated glycoside from sugarcane (Saccharum officinarum) juice. Phytochemistry. 2007;68:1165–71. https://doi.org/10.1016/j.phytochem.2007.01.015.
Article CAS Google Scholar
El-Zaeddi H, Calín-Sánchez Á, Nowicka P, et al. Preharvest treatments with malic, oxalic, and acetylsalicylic acids affect the phenolic composition and antioxidant capacity of coriander, dill and parsley. Food Chem. 2017;226:179–86. https://doi.org/10.1016/j.foodchem.2017.01.067.
Article CAS Google Scholar
Fahim JR, Hegazi GAE-M, El-Fadl RE-SA, et al. Production of rhoifolin and tiliroside from callus cultures of Chorisia chodatii and Chorisia speciosa. Phytochem Lett. 2015;13:218–27. https://doi.org/10.1016/j.phytol.2015.06.004.
Article CAS Google Scholar
Francisco V, Figueirinha A, Costa G, et al. Chemical characterization and antiinflammatory activity of luteolin glycosides isolated from lemongrass. J Funct Food. 2014;10:436–43. https://doi.org/10.1016/j.jff.2014.07.003.
Article CAS Google Scholar
Fu Y, Liu W, Soladoye OP. Towards innovative food processing of flavonoid compounds: insights into stability and bioactivity. LWT – Food Sci Technol. 2021;150:111968. https://doi.org/10.1016/j.lwt.2021.111968.
Article CAS Google Scholar
Galijatovic A, Otake Y, Walle UK, et al. Extensive metabolism of the favonoid chrysin by human Caco-2 and Hep G2 cells. Xenobiotica. 1999;29(12):1241–56.
Article CAS Google Scholar
García-Argáez AN, González-Lugo NM, Parra-Delgado H, et al. Casimiroin, zapoterin, zapotin and 5,6,2′,3′,4′-pentamethoxyflavone from Casimiroa pubescens. Biochem Syst Ecol. 2005;33:441–3. https://doi.org/10.1016/j.bse.2004.11.004.
Article CAS Google Scholar
Genovese MI, de-Moraes-Barros HR. Theobroma cacao and Theobroma grandiflorum: bioactive compounds and associated health benefits. In: Mérillon J-M, Ramawat KG, editors. Bioactive molecules in food reference series in phytochemistry. Cham: Springer Nature; 2019. p. 1049–70. https://doi.org/10.1007/978-3-319-78030-6_15.
Chapter Google Scholar
Hădărugă DI, Hădărugă NG, Bandur GN, et al. Water content of flavonoid/cyclodextrin nanoparticles: relationship with the structural descriptors of biologically active compounds. Food Chem. 2012;132:1651–9. https://doi.org/10.1016/j.foodchem.2011.06.004.
Article CAS Google Scholar
Hostetler GL, Riedl KM, Schwartz SJ. Effects of food formulation and thermal processing on flavones in celery and chamomile. Food Chem. 2013;141:1406–11. https://doi.org/10.1016/j.foodchem.2013.04.051.
Article CAS Google Scholar
Iwashina T, Kamenosono K, Ueno T. Hispidulin and nepetin 4′-glucosides from Cirsium oligophyllum. Phytochemistry. 1999;51:1109–11.
Article CAS Google Scholar
Jabeen E, Janjua NK, Ahmed S, et al. DFT predictions, synthesis, stoichiometric structures and anti-diabetic activity of Cu (II) and Fe (III) complexes of quercetin, morin, and primuletin. J Mol Struct. 2017;1150:459–68. https://doi.org/10.1016/j.molstruc.2017.09.003.
Article CAS Google Scholar
Jiang B, Song J, Jin Y. A flavonoid monomer tricin in Gramineous plants: metabolism, bio/chemosynthesis, biological properties, and toxicology. Food Chem. 2020;320:126617. https://doi.org/10.1016/j.foodchem.2020.126617.
Article CAS Google Scholar
Kalinová PJ, Vrchotová N, Tříska J. Vitexin and isovitexin levels in sprouts of selected plants. J Food Compos Anal. 2021;100:103895. https://doi.org/10.1016/j.jfca.2021.103895.
Kanaze FI, Gabrieli C, Kokkalou E, et al. Simultaneous reversed-phase high-performance liquid chromatographic method for the determination of diosmin, hesperidin and naringin in different citrus fruit juices and pharmaceutical formulations. J Pharmaceut Biomed Anal. 2003;33:243–9. https://doi.org/10.1016/S0731-7085(03)00289-9.
Article CAS Google Scholar
Khan A-u, Gilani AH. Selective bronchodilatory effect of Rooibos tea (Aspalathus linearis) and its flavonoid, chrysoeriol. Eur J Nutr. 2006;45:463–9. https://doi.org/10.1007/s00394-006-0620-0.
Article CAS Google Scholar
Khatteli A, Benabderrahim MA, Triki T, et al. Aroma volatiles, phenolic profile and hypoglycaemic activity of Ajuga iva L. Food Biosci. 2020;36:100578. https://doi.org/10.1016/j.fbio.2020.100578.
Article CAS Google Scholar
Kim YC, Higuchi R, Komori T. Thermal Degradation of Glycosides. VI. Hydrothermolysis of Cardenolide and Flavonoid Glycosides. Liebigs Ann Chem. 1992;1992(6):575–9. https://doi.org/10.1002/jlac.1992199201100.
Article Google Scholar
Kim M-J, Han J-M, Jin Y-Y, et al. In vitro antioxidant and anti-inflammatory activities of jaceosidin from Artemisia princeps Pampanini cv. Sajabal. Arch Pharm Res. 2008;31(4):429–37. https://doi.org/10.1007/s12272-001-1175-8.
Article CAS Google Scholar
Kim SY, Lee HR, Park K-s, et al. Metabolic engineering of Escherichia coli for the biosynthesis of flavonoid-O-glucuronides and flavonoid-O-galactoside. Appl Microbiol Biot. 2015;99:2233–42. https://doi.org/10.1007/s00253-014-6282-6.
Article CAS Google Scholar
Krishna MS, Joy B, Sundaresan A. Effect on oxidative stress, glucose uptake level and lipid droplet content by Apigenin 7, 4′-dimethyl ether isolated from Piper longum L. J Food Sci Technol. 2015;52(6):3561–70. https://doi.org/10.1007/s13197-014-1387-6.
Article CAS Google Scholar
Lataief SB, Zourgui MN, Rahmani R, et al. Chemical composition, antioxidant, antimicrobial and cytotoxic activities of bioactive compounds extracted from Opuntia dillenii cladodes. J Food Measur Charact. 2021;15:782–94. https://doi.org/10.1007/s11694-020-00671-2.
Article Google Scholar
Lee Y-W, Jin Y, Row KH. Extraction and purification of eupatilin from Artemisia princeps PAMPAN recycling preparative HPLC. Korean J Chem Eng. 2006;23(2):279–82.
Article CAS Google Scholar
Lee Y-H, Charles AL, Kung H-F, et al. Extraction of nobiletin and tangeretin from Citrus depressa Hayata by supercritical carbon dioxide with ethanol as modifier. Ind Crop Prod. 2010;31:59–64. https://doi.org/10.1016/j.indcrop.2009.09.003.
Article CAS Google Scholar
Lee S, Han S, Kim HM, et al. Simultaneous Determination of Luteolin and Luteoloside in Dandelions Using HPLC. Hortic Environ Biotech. 2011;52(5):536–40. https://doi.org/10.1007/s13580-011-0214-5.
Article CAS Google Scholar
Lee JH, Park MJ, Ryu H, et al. Elucidation of phenolic antioxidants in barley seedlings (Hordeum vulgare L.) by UPLC-PDA-ESI/MS and screening for their contents at different harvest times. J Funct Food. 2016;26:667–80. https://doi.org/10.1016/j.jff.2016.08.034.
Article CAS Google Scholar
Lee S, Lee D-H, Kim J-C, et al. Pectolinarigenin, an aglycone of pectolinarin, has more potent inhibitory activities on melanogenesis than pectolinarin. Biochem Biophys Res Co. 2017;493:765–72. https://doi.org/10.1016/j.bbrc.2017.08.106.
Article CAS Google Scholar
Li S, Wang H, Guo L, et al. Chemistry and bioactivity of nobiletin and its metabolites. J Funct Food. 2014;6:2–10. https://doi.org/10.1016/j.jff.2013.12.011.
Article CAS Google Scholar
Li S, Zhou S, Yang W, et al. Gastro-protective effect of edible plant Artemisia argyi in ethanol-induced rats via normalizing inflammatory responses and oxidative stress. J Ethnopharmacol. 2018;214:207–17. https://doi.org/10.1016/j.jep.2017.12.023.
Article CAS Google Scholar
Li J, Tian C, Xia Y, et al. Production of plant-specific flavones baicalein and scutellarein in an engineered E. coli from available phenylalanine and tyrosine. Metab Eng. 2019;52:124–33. https://doi.org/10.1016/j.ymben.2018.11.008.
Article CAS Google Scholar
Lu S, Tao J, Liu X, et al. Baicalin-liposomes loaded polyvinyl alcohol-chitosan electrospinning nanofibrous films: characterization, antibacterial properties and preservation effects on mushrooms. Food Chem. 2022;371:131372. https://doi.org/10.1016/j.foodchem.2021.131372.
Article CAS Google Scholar
Luthria DL. Influence of experimental conditions on the extraction of phenolic compounds from parsley (Petroselinum crispum) flakes using a pressurized liquid extractor. Food Chem. 2008;107:745–52. https://doi.org/10.1016/j.foodchem.2007.08.074.
Article CAS Google Scholar
Maldonado EM, Salamanca E, Giménez A, et al. Antileishmanial metabolites from Lantana balansae. Rev Bras Farmacogn. 2016;26:180–3. https://doi.org/10.1016/j.bjp.2015.11.007.
Article CAS Google Scholar
Min S-W, Kim N-J, Baek N-I, Kim D-H. Inhibitory effect of eupatilin and jaceosidin isolated from Artemisia princeps on carrageenan-induced inflammation in mice. J Ethnopharmacol. 2009;125:497–500. https://doi.org/10.1016/j.jep.2009.06.001.
Mohanlal S, Maney SK, Santhoshkumar TR, et al. Tricin 4′-O-(erythro-β-guaiacylglyceryl) ether and tricin 4′-O-(threo-β-guaiacylglyceryl) ether isolated from Njavara (Oryza sativa L. var. Njavara), induce apoptosis in multiple tumor cells by mitochondrial pathway. J Nat Med. 2013;67:528–33. https://doi.org/10.1007/s11418-012-0710-7.
Article CAS Google Scholar
Moheb A, Grondin M, Ibrahim RK, et al. Winter wheat hull (husk) is a valuable source for tricin, a potential selective cytotoxic agent. Food Chem. 2013;138:931–7. https://doi.org/10.1016/j.foodchem.2012.09.129.
Article CAS Google Scholar
Myoung H-J, Kim G, Nam K-W. Apigenin Isolated from the Seeds of Perilla frutescens Britton var crispa (Benth.) Inhibits Food Intake in C57BL/6J Mice. Arch Pharm Res. 2010;33(11):1741–6. https://doi.org/10.1007/s12272-010-1105-5.
Article CAS Google Scholar
Oba C, Ota M, Nomura K, et al. Extraction of nobiletin from Citrus Unshiu peels by supercritical fluid and its CRE-me diate d transcriptional activity. Phytomedicine. 2017;27:33–8. https://doi.org/10.1016/j.phymed.2017.01.014.
Article CAS Google Scholar
Pandey P, Khan F. A mechanistic review of the anticancer potential of hesperidin, a natural flavonoid from citrus fruits. Nutr Res. 2021;92:21–31. https://doi.org/10.1016/j.nutres.2021.05.011.
Article CAS Google Scholar
Park C-Y, Kim S, Lee D, et al. Enzyme and high pressure assisted extraction of tricin from rice hull and biological activities of rice hull extract. Food Sci Biotechnol. 2016;25(1):159–64. https://doi.org/10.1007/s10068-016-0024-8.
Article CAS Google Scholar
Patel K, Patel DK. Medicinal importance, pharmacological activities, and analytical aspects of hispidulin: a concise report. J Trad Complem Med. 2017;7:360–6. https://doi.org/10.1016/j.jtcme.2016.11.003.
Article Google Scholar
Peng J, Dai W, Lu M, et al. New insights into the influences of baking and storage on the nonvolatile compounds in oolong tea: a nontargeted and targeted metabolomics study. Food Chem. 2022;375:131872. https://doi.org/10.1016/j.foodchem.2021.131872.
Article CAS Google Scholar
Pereira OR, Domingues MRM, Silva AMS, et al. Phenolic constituents of Lamium album: focus on isoscutellarein derivatives. Food Res Int. 2012;48:330–5. https://doi.org/10.1016/j.foodres.2012.04.009.
Article CAS Google Scholar
Pereira DTV, Zabot GL, Reyes FGR, et al. Integration of pressurized liquids and ultrasound in the extraction of bioactive compounds from passion fruit rinds: impact on phenolic yield, extraction kinetics and technical-economic evaluation. Innov Food Sci Emerg Technol. 2021;67:102549. https://doi.org/10.1016/j.ifset.2020.102549.
Article CAS Google Scholar
Poureini F, Mohammadi M, Najafpour GD. Comparative study on the extraction of apigenin from parsley leaves (Petroselinum crispum L.) by ultrasonic and microwave methods. Chem Pap. 2020;74:3857–71. https://doi.org/10.1007/s11696-020-01208-z.
Article CAS Google Scholar
Qiu C, Wang H, Zhao L, et al. Orientin and vitexin production by a one-pot enzymatic cascade of a glycosyltransferase and sucrose synthase. Bioorg Chem. 2021;112:104926. https://doi.org/10.1016/j.bioorg.2021.104926.
Article CAS Google Scholar
Ramadevi S, Kaleeswaran B, Ilavenil S, et al. Effect of traditionally used herb Pedalium murex L. and its active compound pedalitin on urease expression – for the management of kidney stone. Saudi J Biol Sci. 2020;27:833–9. https://doi.org/10.1016/j.sjbs.2020.01.014.
Article CAS Google Scholar
Šarić A, Balog T, Sobočanec S, et al. Antioxidant effects of flavonoid from Croatian Cystus incanus L. rich bee pollen. Food Chem Toxicol. 2009;47:547–54. https://doi.org/10.1016/j.fct.2008.12.007.
Article CAS Google Scholar
Sarıkahya NB, Gören AC, Okkalı GS, et al. Chemical composition and biological activities of propolis samples from different geographical regions of Turkey. Phytochem Lett. 2021;44:129–36. https://doi.org/10.1016/j.phytol.2021.06.008.
Article CAS Google Scholar
Šatínský D, Jägerová K, Havlíková L, et al. A new and fast HPLC method for determination of rutin, troxerutin, diosmin and hesperidin in food supplements using fused-core column technology. Food Anal Method. 2013;6:1353–60. https://doi.org/10.1007/s12161-012-9551-y.
Article Google Scholar
Shafaei A, Saeed MAA, Hamil MSR, et al. Application of high performance liquid chromatography and Fourier-transform infrared spectroscopy techniques for evaluating the stability of Orthosiphon aristatus ethanolic extract and its nano liposomes. Rev Bras Farmacogn. 2018;28:658–68. https://doi.org/10.1016/j.bjp.2018.07.005.
Article CAS Google Scholar
Silva AV, Yerena LR, Necha LLB. Chemical profile and antifungal activity of plant extracts on Colletotrichum spp. isolated from fruits of Pimenta dioica (L.) Merr. Pesticide Biochem Physiol. 2021;179:104949. https://doi.org/10.1016/j.pestbp.2021.104949.
Article CAS Google Scholar
Son NT, Thanh DTM, Van-Trang N. Flavone norartocarpetin and isoflavone 20-hydroxygenistein: a spectroscopic study for structure, electronic property and antioxidant potential using DFT (Density functional theory). J Mol Struct. 2019;1193:76–88. https://doi.org/10.1016/j.molstruc.2019.05.016.
Article CAS Google Scholar
Stahlhut SG, Siedler S, Malla S, et al. Assembly of a novel biosynthetic pathway for production of the plant flavonoid fisetin in Escherichia coli. Metab Eng. 2015;31:84–93. https://doi.org/10.1016/j.ymben.2015.07.002.
Article CAS Google Scholar
Sun-Waterhouse D, Wadhwa SS. Industry-relevant approaches for minimising the bitterness of bioactive compounds in functional foods: a review. Food Bioprocess Tech. 2013;6:607–27. https://doi.org/10.1007/s11947-012-0829-2.
Article CAS Google Scholar
Tetko IV, Gasteiger J, Todeschini R, et al. Virtual computational chemistry laboratory – design and description. J Comput-Aided Mol Design. 2005;19:453–63. https://doi.org/10.1007/s10822-005-8694-y.
Article CAS Google Scholar
Theodoratou E, Kyle J, Cetnarskyj R, et al. Dietary flavonoids and the risk of colorectal cancer. Cancer Epidemiology Biomark Prevent. 2007;16(4):684–93. https://doi.org/10.1158/1055-9965.EPI-06-0785.
Article CAS Google Scholar
Tyśkiewicz K, Konkol M, Kowalski R, et al. Characterization of bioactive compounds in the biomass of black locust, poplar and willow. Trees. 2019;33:1235–63. https://doi.org/10.1007/s00468-019-01837-2.
Article CAS Google Scholar
Viganó J, Brumer IZ, de-Campos-Braga PA, et al. Pressurized liquids extraction as an alternative process to readily obtain bioactive compoundsfrom passion fruit rinds. Food Bioprod Process. 2016;100:382–90. https://doi.org/10.1016/j.fbp.2016.08.011.
Article CAS Google Scholar
Wang X, Liu Y, He L-L, et al. Spectroscopic investigation on the food components-drug interaction: the influence of flavonoids on the affinity of nifedipine to human serum albumin. Food Chem Toxicol. 2015;78:42–51. https://doi.org/10.1016/j.fct.2015.01.026.
Article CAS Google Scholar
Wang X, Guo X-Y, Xu L, et al. Studies on the competitive binding of cleviprex and flavonoids to plasma protein by multi-spectroscopic methods: a prediction of food-drug interaction. J Photochem Photobiol B: Biol. 2017;175:192–9. https://doi.org/10.1016/j.jphotobiol.2017.08.037.
Article CAS Google Scholar
Wei Y, Li L, Xi Y, et al. Sustained release and enhanced bioavailability of injectable scutellarin-loaded bovine serum albumin nanoparticles. Int J Pharm. 2014;476:142–8. https://doi.org/10.1016/j.ijpharm.2014.09.038.
Article CAS Google Scholar
Wei J, Cao P, Wang J, et al. Analysis of tilianin and acacetin in Agastache rugosa by high-performance liquid chromatography with ionic liquids-ultrasound based extraction. Chem Cent J. 2016;10:76. https://doi.org/10.1186/s13065-016-0223-7.
Article CAS Google Scholar
Weiss J, Gattuso G, Barreca D, et al. Nobiletin, sinensetin, and tangeretin are the main perpetrators in clementines provoking food-drug interactions in vitro. Food Chem. 2020;319:126578. https://doi.org/10.1016/j.foodchem.2020.126578.
Article CAS Google Scholar
Williamson G, Kay CD, Crozier A. The bioavailability, transport, and bioactivity of dietary flavonoids: a review from a historical perspective. Compr Rev Food Sci Food Safety. 2018;17(5):1054–112. https://doi.org/10.1111/1541-4337.12351.
Article Google Scholar
Wishart DS, Feunang YD, Guo AC, et al. DrugBank 5.0: a major update to the DrugBank database for 2018. Nucleic Acids Res. 2018;46:D1074–82. https://doi.org/10.1093/nar/gkx1037.
Article CAS Google Scholar
Yam MF, Mohamed EAH, Ang LF, et al. A Simple Isocratic HPLC Method for the Simultaneous Determination of Sinensetin, Eupatorin, and 3′-hydroxy-5,6,7,4′-tetramethoxyflavone in Orthosiphon stamineus Extracts. J Acupunct Merid Stud. 2012;5(4):176–82. https://doi.org/10.1016/j.jams.2012.05.005.
Article Google Scholar
Ye H, Shaw IC. Food flavonoid ligand structure/estrogen receptor-α affinity relationships – toxicity or food functionality? Food Chem Toxicol. 2019;129:328–36. https://doi.org/10.1016/j.fct.2019.04.008.
Article CAS Google Scholar
Yeh T-S, Yuan C, Ascherio A, et al. Long-term dietary flavonoid intake and subjective cognitive decline in US men and women. Neurology. 2021;97(10):e1041–56. https://doi.org/10.1212/WNL.0000000000012454.
Article CAS Google Scholar
Yong H, Bi F, Liu J, et al. Preparation and characterization of antioxidant packaging by chitosan, D-α-tocopheryl polyethylene glycol 1000 succinate and baicalein. Int J Biol Macromol. 2020;153:836–45. https://doi.org/10.1016/j.ijbiomac.2020.03.076.
Article CAS Google Scholar
Zaragozá C, Monserrat J, Mantecón C, et al. Binding and antiplatelet activity of quercetin, rutin, diosmetin, and diosmin flavonoids. Biomed Pharmacother. 2021;141:111867. https://doi.org/10.1016/j.biopha.2021.111867.
Article CAS Google Scholar
Zeraik ML, Yariwake JH. Quantification of isoorientin and total flavonoids in Passiflora edulis fruit pulp by HPLC-UV/DAD. Microchem J. 2010;96:86–91. https://doi.org/10.1016/j.microc.2010.02.003.
Article CAS Google Scholar
Zhang Y, Bao B, Lu B, et al. Determination of flavone C-glucosides in antioxidant of bamboo leaves (AOB) fortified foods by reversed-phase high-performance liquid chromatography with ultraviolet diode array detection. J Chromatogr A. 2005;1065:177–85. https://doi.org/10.1016/j.chroma.2004.12.086.
Article CAS Google Scholar
Zhang Y, Li H, Dou H, et al. Optimization of Nobiletin Extraction Assisted by Microwave from Orange Byproduct Using Response Surface Methodology. Food Sci Biotechnol. 2013;22(S):153–9. https://doi.org/10.1007/s10068-013-0061-5.
Article CAS Google Scholar
Zhao D, Xing J, Li M, et al. Optimization of growth and jaceosidin production in callus and cell suspension cultures of Saussurea medusa. Plant Cell Tiss Org Cult. 2001;67:227–34.
Article CAS Google Scholar
Zheng T, Wong ECW, Yue GGL, et al. Identification and quantification of tricin present in medicinal herbs, plant foods and by-products using UPLC-QTOF-MS. Chem Pap. 2021;75:4579–88. https://doi.org/10.1007/s11696-021-01651-6.
Article CAS Google Scholar
Zhou L, Jing T, Zhang P, et al. Kinetics and modeling for extraction of chrysin from Oroxylum indicum seeds. Food Sci Biotechnol. 2015;24(6):2045–50. https://doi.org/10.1007/s10068-015-0272-z.
Article CAS Google Scholar

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Department of Applied Chemistry, Organic and Natural Compounds Engineering, Polytechnic University of Timişoara, Timişoara, Romania
Daniel-Ioan Hădărugă
Department of Food Science, Banat’s University of Agricultural Sciences and Veterinary Medicine “King Michael I of Romania” – Timişoara, Timişoara, Romania
Nicoleta-Gabriela Hădărugă

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Daniel-Ioan Hădărugă
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Nicoleta-Gabriela Hădărugă
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Correspondence to Nicoleta-Gabriela Hădărugă .

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International Iberian Food Laboratory, University of Vigo, Vigo, Spain
Seid Mahdi Jafari
Massey University, Riddet Institute, Palmerston North, New Zealand
Ali Rashidinejad
Nutrition and Food Science Group, University of Vigo, Vigo, Spain
Jesus Simal-Gandara

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Riddet Institute, Massey University, Palmerston North, New Zealand
Ali Rashidinejad

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Hădărugă, DI., Hădărugă, NG. (2023). Flavones. In: Jafari, S.M., Rashidinejad, A., Simal-Gandara, J. (eds) Handbook of Food Bioactive Ingredients. Springer, Cham. https://doi.org/10.1007/978-3-030-81404-5_4-1

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DOI: https://doi.org/10.1007/978-3-030-81404-5_4-1
Received: 11 May 2022
Accepted: 16 September 2022
Published: 02 February 2023
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-81404-5
Online ISBN: 978-3-030-81404-5
eBook Packages: Springer Reference Biomedicine and Life SciencesReference Module Biomedical and Life Sciences

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