A comprehensive review on flavanones, the major citrus polyphenols Muhammad Kamran Khan, - Zill-E-Huma, Olivier Dangles
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Muhammad Kamran Khan, - Zill-E-Huma, Olivier Dangles. A comprehensive review on flavanones, the major citrus polyphenols. Journal of Food Composition and Analysis, Elsevier, 2014, 33, pp.85- 104. 10.1016/j.jfca.2013.11.004. hal-02640844
HAL Id: hal-02640844 https://hal.inrae.fr/hal-02640844 Submitted on 28 May 2020
HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Version postprint Manuscrit d’auteur / Author manuscript Manuscrit d’auteur / Author manuscript Manuscrit d’auteur / Author manuscript Journal homepage: Journal Foodof Composition and Analysis Ve Accepted Received Received Article A Citrus Keywords: Food Bioactivity Bioavailability Analysis Extraction Synthesis Metabolites Glucuronide Conjugate Chalcone Flavanone Polyphenol Grapefruit Orange http://dx.doi.org/10.1016/j.jfca.2013.11.004 0889-1575/$ Contents c b a Muhammad A Critical Khan, M. K.(Auteurde correspondance), Zill-E-Huma, Dangles,O. (2014).Acomprehensive review
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knowledge
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- D with ´ 3-
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liver -
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2001 Boumendjel
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common
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compounds (
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and 2007
for Fig.
,
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effects the (
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et
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and
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Kothakonda, ). to
Recently, our
synthesis
synthesis works al., ). antioxidant
A
Lewis
other
polyphenol elucidating by the A interest naringenin
as glucuronyl
flavanone
and
the biological flavanone
protected
by synthesis (phenolic synthesis to
and
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1996) research requires position are regiose- methyl- Botting,
biologi-
methyl groups
O
obtain
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yields et
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2000
hand,
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have
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(of 4
as or D of 93 of 0 - - ) ) Version postprint Manuscrit d’auteur / Author manuscript Manuscrit d’auteur / Author manuscript Manuscrit d’auteur / Author manuscript 7.1. been flavonol and et summarized (metabolites) ( metabolism, and been MeOH assessed animals juices 94 metabolites Fig. hydrolysed pletely populations and across ingested: the or imidazole, the glucuronides, 7. lumen detected Matsumoto Journal homepage: Journal Foodof Composition and Analysis Ve
interstitial al., Khan, M. K.(Auteurde correspondance), Zill-E-Huma, Dangles,O. (2014).Acomprehensive review Bioavailability
Intestinal After The
6.
r intestine. excretion. hesperetin, significant Intestinal
si
released
(A) reported.
(2/5), evaluated
2003
worldwide, on définitive du du m on définitive
of the known. oral
Glucuronidation
can intake
oral
NMP in
on flavanones, themajor citruspolyphenols. Journal ofFoodComposition andAnalysis, nutrients in
then
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). the small bioavailability in
provide
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vitro et intake, in For
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absorption
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sulfates are For absorption acidification
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given several
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of fate also mean glucosides by
matrix 33, 85-104. DOI: 10.1016/j.jfca.2013.11.004 converted
about
liver. of has
al., high and r
pharmacokinetics
Dowex
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flavanones of European
Finally, compared the
M.K.
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Cl and (bioaccessibility, the
Comment citer cedocument: been flavanones 2
),
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sulfates) after various their respectively,
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in is
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l nal
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Finland
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absorption, Glucuronidation
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naringenin
excretions
respective
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fruits four-time
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has not are on of theof on ma ).
Composition 33, 85- p is ester
Pyridin
of
group),
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hesperetin the
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conditions (after mol/L, Erlund co-authors
: : 20 and for absorption from higher
on 33
were
(2/5), naringenin
naringenin
1.3–2.2 10.1016/j.jfca.2013.11.004
2 a
excretion a (8
mg best (20
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naringenin
naringenin
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equiv.),
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hed 85–104
Manach h
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in
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distribution
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knowledge, 2 after
of
After
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naringin
2003
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). 1 liver of
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mg
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) range orange
+ group),
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bile ingestion,
form). liver
urine
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mol/L
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Tsai,
high 0.6–
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the (5–
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or to in O/ ) Version postprint Manuscrit d’auteur / Author manuscript Manuscrit d’auteur / Author manuscript Manuscrit d’auteur / Author manuscript Journal homepage: Journal Foodof Composition and Analysis Ve (0.38%) (flavanone dyspepsia. traditional absorbed group none the 3.7 These ly. pointed ported 2008 transcellular Intestinal back vitro circulation with glycosides structure polarized ( which fed sinensis (hesperetin membranes ( mechanism rhamnoglucoside showed naringenin the determinant The Khan, M. K.(Auteurde correspondance), Zill-E-Huma, Dangles,O. (2014).Acomprehensive review Gardana Miyake r
si The
The
source and faster consumption on définitive du du m on définitive
with
). into neohesperiosides) naringenin
models,
citrus
studied
are on flavanones, themajor citruspolyphenols. Journal ofFoodComposition andAnalysis,
The from urinary ,
permeability
and
8.5 et to
respectively,
a and
the
across
et
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naringenin
ABC absorption
present
The
( al., was rutinosides) and Chinese
side)
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faster
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al.,
intestinal glycoside).
environment involves of
2006 passive after
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T eriodictyol
proton-coupled
confirmed transporters
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membrane
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bioavailability
Felgines al., side
in hydrolysis ).
the medicine (time
Citrus
The
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are
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intestinal 2010
www.elsevier.com/locate/jfca
which than further
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that
-rhamnoglucoside
33, 85-104. DOI: 10.1016/j.jfca.2013.11.004
or
used al., probably
eriodictyol in elaborated
et r rate more
et enterocytes absorption
it
active
the
(lumen uptake hesperetin naringin
absorption.
p of
the
al.,
diet), 2000
along cells aglycones
al., have
C
ublié
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mechanisms for 2008 ( ones
formulation
cassette Kobayashi bioavailable 2007
L. Comment citer cedocument:
was
basolateral
).
was
M.K. transport to
)
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in
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with hesperidin
and ). comparison flavanones and
to
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dan
).
Khan fed
hesperetin found two glycosides
More treatment and
mechanisms
the compared of Flavanones explain Citrus An
neohesperidin or
eriocitrin related s s / Fi and
(ABC)
a C.
with et
times
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facilitate and
and
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recently,
( of
al. aurantium side newly
Kobayashi to
were
4 (201 than naringenin
sinensis vitro /
Zhi
l nal
Konishi,
Journal
urine
and the
across
is
be naringenin-7-
depending higher
to
transporters, was of
(blood). respectively. to - Fig. to
b
also Zhu
respective- ver in hesperidin
hesperetin
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-glucoside efficiently ), functional H flavanone
excretion flavonoid proposed
the
narirutin 7. involved vol vol
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Osbeck.
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Wan, a
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Composition at in
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Brand of 104, -sulfate
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The metabolites
by membrane. to has of are 10.1016/j.jfca.2013.11.004
missing S
hesperetin
colon 2010
of analyzing
)-enantiomers cell 33
that
show and/or predominantly that
human authentic made
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85–104 very
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:
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flavanone
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glycosides
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estimate involves in
permeates pattern
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Indeed, Fig. bioavailability and
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Investigations to -
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is
Those et et these
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side rats
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By
7- to D in of 95 of of - Version postprint Manuscrit d’auteur / Author manuscript Manuscrit d’auteur / Author manuscript Manuscrit d’auteur / Author manuscript ( 24 ingestion. of cases is catechol-O-methyltransferase through acid, confirmed from (0–24 in Bacteroides bearing et acids that 96 rats tumor catechol naringenin the et naringenin-7-O- tion, tions by matrices quantity conversion aglycones 3,4-dihydroxycinnamic phenolic metabolism, metabolism phenolic ( impact naringenin cleaves Addition to Manach Mullen Journal homepage: Journal Foodof Composition and Analysis Ve
metabolized the
al., catechin al., Khan, M. K.(Auteurde correspondance), Zill-E-Huma, Dangles,O. (2014).Acomprehensive review h The Recently,
analyzing UDP-glucuronosyltransferase diet,
r
the si of
fed
similar were
and
the methylation
distal
2003 h) 2000 reach on définitive du du m on définitive
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orange
on the
rats
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which
quantity
methylation
et
acids groups may on flavanones, themajor citruspolyphenols. Journal ofFoodComposition andAnalysis,
with et
did acids luminal
of flavanone of
p
However, are
estimated in the
). ). -hydroxybenzoic uniformis
al.,
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al.,
and
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of naringenin
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Likewise, Silberberg flavanone After not
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www.elsevier.com/locate/jfca any liver the et acid
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(cecum).
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sulfotransferase
Comment citer cedocument:
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Interaction s Glucuronidation Flavanones In
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Analysis
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C,
are in
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chalcones
are Flavanone / phenoli
pt publis in (reducing) (pH with
flavanone
glucuron freezing al., 0
metabolites
and : : industrially flavanones -
Flavanone 33 2007 antioxidant
were decade, The
expected O-sulfate-7- their
small 10.1016/j.jfca.2013.11.004 appeared was
of
or
activity
Phenoli which
diglyc (2014) (
2003 could Flavanone
7.5). occurs naringenin-7-O
Tripoli (
on
metabolites,
their Manach specific Colon
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).
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