Flavanones in Plants and Humans

Hădărugă, Daniel-Ioan; Hădărugă, Nicoleta-Gabriela

doi:10.1007/978-3-030-81404-5_6-1

Daniel-Ioan Hădărugă⁴ &
Nicoleta-Gabriela Hădărugă^5,6

20 Accesses

Abstract

This chapter is focused on the main (S)-2-phenylchroman-4-one derivatives, especially hydroxyl- and methoxy substituted compounds (flavanone aglycones), as well as flavanone glycosides. The first part presents the chemistry and functionality of flavanones that have been widely found in various plants and food products. It is the case of hesperetin, naringenin, and isosakuranetin, including their glycosides (hesperidin and naringin) from Citrus species, as well as liquiritigenin in Glycyrrhiza species (licorice). However, flavanone glycosides are more concentrated in these natural sources, and other glycosylated derivatives can be found, e.g., neohesperidin, didymin, prunin, or narirutin in Citrus. Antioxidant mechanisms of flavanone have been presented and discussed related to quantum-chemical descriptors obtained by molecular modeling. The hydrophobicity of flavanones glycosides well correlates with the incidence of hydroxyl/methoxy groups and with sugar units. The presence of mono- and disaccharide moieties in flavanone glycosides increases the hydrophilicity, and thus, the water solubility/bioavailability. As a consequence, the metabolism of flavanones in various organs of the human body is described in the second part. The general biosynthetic pathways of flavanones in plants, particularly of sakuranetin in rice, (2S)-pinocembrin in engineered Escherichia coli or E. coli co-culture, homoeriodictyol by recombinant flavone 3’-O-methyltransferase, and hesperetin from hesperidin in Citrus juice, are also discussed in this part. The final section is dedicated to the occurrence, separation/production, analysis, and applications of specific flavanone aglycones and glycosides as food ingredients. Special attention has been given to butin, eriodictyol, homoeriodictyol, hesperetin, liquiritigenin, naringenin, pinocembrin, and sakuranetin from flavanone aglycone class. On the other hand, hesperidin, neohesperidin, naringin, narirutin, eriocitrin, neoeriocitrin, poncirin, neoponcirin, didymin, prunin, and sakuranin are known to be the main flavanone glycosides, which have been discussed in this section. The chapter ends with conclusion and future perspectives related to this important class of flavonoids with valuable biological and food applications.

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Abbreviations

¹H/¹³C-NMR:: ¹H/¹³C-nuclear magnetic resonance
4CL:: 4-coumarate:coenzyme A ligase
ABTS·⁺:: 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation
AFM:: Atomic force microscopy
ATP:: Adenosine triphosphate
C4H:: Cinnamate 4-hydroxylase
CD:: Circular dichroism
CFI:: Chalcone-flavanone isomerase
CHS:: Chalcone synthase
CHR:: Chalcone reductase
CoA:: Coenzyme A
Cuphen:: Copper-phenanthroline assay
CUPRAC:: Cupric reducing antioxidant capacity
CYP3A4:: Cytochrome P450IIIA4
DAHP:: 3-deoxy-d-arabinoheptulosonate-7-phosphate
DPPH:: 2,2-diphenyl-1-pycrylhydrazyl radical
DSC:: Differential scanning calorimetry
DW:: Dry weight
E4P:: Erythrose 4-phospate
EPSP:: 5-enolpyruvylshikimic acid 3-phosphate
ESI-MS:: Electrospray ionization-mass spectrometry
F3′H:: Flavonoid 3′-hydroxylase
FAB-MS:: Fast atom bombardment-mass spectrometry
FAME:: Fatty acid methyl ester
FRAP:: Ferric reducing antioxidant power
FT-IR:: Fourier transform infrared spectroscopy
FW:: Fresh weight
GC-FID/MS:: Gas chromatography coupled with flame ionization detector/mass spectrometry detector
HAT:: Hydrogen atom transfer
HOMO:: Highest occupied molecular orbital
HPLC-UV-Vis/DAD/ESI-MS/MS/MS²/RID:: High-pressure liquid chromatography coupled with ultraviolet-visible spectrophotometric detector/diode array detector/electrospray ionization detector/mass spectrometry detector/tandem mass spectrometry detector/refractive index detector
HPAEC-PAD:: High-performance anion exchange chromatography-pulsed amperometric detector
HPIEC:: High-performance ion exchange chromatography
HPP:: High-pressure processing
HP-TLC:: High-performance thin layer chromatography
HSCCC:: High-speed countercurrent chromatography
ICP-MS:: Inductively coupled plasma mass spectrometry
KFT:: Karl Fischer water titration
LCV:: Liquid chromatography under vacuum
LDA:: Linear discriminant analysis
LUMO:: Lowest unoccupied molecular orbital
MAE:: Microwave-assisted extraction
NADP⁺/NADPH:: Nicotinamide adenine dinucleotide phosphate/reduced form
NOMT:: Naringenin 7-O-methyltransferase
ORAC:: Oxygen radical absorbance capacity
OsNOMT:: Oryza sativa L. naringenin 7-O-methyltransferase
PAL:: Phenylalanine ammonia lyase
PCA:: Principal component analysis
PEF:: Pulsed electric field
PEP:: Phosphoenol pyruvate
pheA ^fbr :: Feedback-inhibition-resistant (fbr) chorismate mutase/prephenate dehydratase (CM/PDT)
PLS-DA:: Projection in latent structure/partial least squares-discriminant analysis
ROMT-9:: Flavone 3’-O-methyltransferase
RT-qPCR:: Reverse transcription and quantitative polymerase chain reaction
SAH:: S-adenosyl-l-homocysteine
SAM:: S-adenosyl-l-methionine
SC-CO₂:: Supercritical carbon dioxide extraction
SDS-PAGE:: Sodium dodecyl sulfate-polyacrylamide gel electrophoresis
SEM:: Scanning electron microscopy
SET:: Single-electron transfer
SET-PT:: Single-electron transfer followed by proton transfer
SMEDDS:: Self-microemulsifying drug delivery system
SPE:: Solid-phase extraction
SPLET:: Sequential proton loss electron transfer
SPME:: Solid-phase microextraction
SWE:: Subcritical water extraction
TAL:: Tyrosine ammonia lyase
TEAC:: Trolox equivalent antioxidant capacity
TEM:: Transmission electronic microscopy
TLC:: Thin layer chromatography
TMC:: Transition metals chelation
UAE:: Ultrasound-assisted extraction
UDP-GT:: Uridine diphosphate-glucuronotransferase
UHPLC-DAD-ESI-MS/QTOF-MS/MS^2/n:: Ultrahigh-pressure liquid chromatography coupled with photodiode array detector/electrospray ionization-mass spectrometry detector/quadrupole time-of-flight mass spectrometry/tandem mass spectrometry detector
UV-Vis:: Ultraviolet-visible spectrophotometry
WPI:: Whey protein isolate
XRD:: X-ray diffractometry

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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, University of Life Sciences “King Mihai I” from Timişoara, Timişoara, Romania
Nicoleta-Gabriela Hădărugă
Research Institute for Biosecurity and Bioengineering, Timişoara, Romania
Nicoleta-Gabriela Hădărugă

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Daniel-Ioan 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). Flavanones in Plants and Humans. 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_6-1

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DOI: https://doi.org/10.1007/978-3-030-81404-5_6-1
Received: 09 July 2022
Accepted: 14 September 2022
Published: 26 April 2023
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-81404-5
Online ISBN: 978-3-030-81404-5
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