Research Article

Received: 8 June 2013 Revised: 28 August 2013 Accepted article published: 11 September 2013 Published online in Wiley Online Library: 22 October 2013

(wileyonlinelibrary.com) DOI 10.1002/jsfa.6387

Polyphenolic compounds in date fruit seed

(Phoenix dactylifera): characterisation and
quantification by using UPLC-DAD-ESI-MS
Hosam M Habib,a Carine Platat,a∗ Emmanuelle Meudec,b
Veronique Cheynierb and Wissam H Ibrahima

Abstract
BACKGROUND: Date fruit seeds have been demonstrated to possess high antioxidant activities due to their high content of
flavonoids and phenolic compounds. The objective of this work was to identify and quantify the phenolic composition of date
seeds.

METHODS: Two UPLC-DAD-ESI-MS analyses were performed on the seed of the Khalas variety as follows: (1) an analysis of simple
phenolic compounds [phenolic acids, hydroxycinnamic acids, flavonols, flavones, flavan-3-ols (monomers, dimers and trimers)];
and (2) an analysis of all flavan-3-ols (monomers, and proanthocyanidin oligomers and polymers) after depolymerisation.

RESULTS: The amount of total phenolic compounds before depolymerisation was found to be 2.194 ± 0.040 g kg−1 date
seed. The analysis of flavan-3-ol monomers and constitutive units of proanthocyanidins after depolymerisation revealed
50.180 ± 1.360 g kg−1 flavan-3-ols with 46.800 ± 1.012 g kg−1 epicatechin and 3.380 ± 0.349 g kg−1 catechin.

CONCLUSION: The results indicate that date seeds are a very rich source of bioactive compounds, thus constituting strong
candidates for functional food additives and nutraceuticals.

c 2013 Society of Chemical Industry

Keywords: date seeds; flavonoids; phenolic compounds; antioxidants; proanthocyanidins

INTRODUCTION antioxidant activity of hydroxycinnamic acids was higher than that

Dates are largely cultivated in the Middle East and are one of the
most popular staple foods in this region of the world. Date seed
is one of the waste products, generated in a huge amount in the
date’s production process. A high nutritional value and health ben-
efits have long been demonstrated for date flesh.1 Date flesh is also
recognised as a rich source of antioxidant compounds including
phenolic acids and flavonoids.2,3 Date seeds have also been shown
to have an excellent nutritional quality due to high amounts of fibre
(676–742 g kg−1 depending on variety) and considerable amounts
of minerals, vitamins, lipids and protein.4,5 Additionally, date seeds
were shown to be rich in antioxidants4 – 6 containing mainly phe-
nolics (24.6 g kg−1 gallic acid equivalent) and total flavonoids (
63.67 g kg−1 rutin equivalent). As has already been demonstrated
in other fruits and corresponding seeds, total polyphenol content
of the date seeds was higher than in the edible flesh.7
The interest in polyphenols is largely related to their contribution
to human health through their multiple biological effects such as
antioxidant activity, antimutagenic and anticarcinogenic activities,
and anti-inflammatory actions.8,9 Flavonoids possess excellent
antioxidant properties related to their abilities to interfere with the
formation and propagation of free radicals and protect low density
lipoproteins from oxidation.10 Interestingly, it has been shown
that different classes of polyphenols contribute to the antioxidant
1084
of the corresponding hydroxybenzoic acids in grapes.11
Due to their interesting nutritional properties, date seeds
represent a potential strong candidate as functional ingredient
for human food. Moreover, a recent study showed that date seeds
exerted antioxidant activity in rats fed with diets containing 7% and
14% date seed powder for 30 days.12 This study also reported no
adverse effects of date seed on organ function, lipid profile, protein
metabolism, haematological parameters, and body weight.
Nevertheless, so far, the detailed phenolic profile of date seeds
and the quantities of these bioactive compounds have not been
comprehensively investigated. Due to the fact that the properties
of these compounds may differ according to their quantity and
chemical form in the plant sample, there is an urgent need to
more precisely identify the compounds in date seeds in order to
better understand the potential health benefits, especially their
∗ Correspondence to: Carine Platat, Department of Nutrition and Health, College
of Food and Agriculture, UAE University, P.O. Box 15551, Al Ain, United Arab
Emirates. E-mail: platatcarine@uaeu.ac.ae
a Department of Nutrition and Health, UAE University, P.O. Box 15551, Al Ain,
United Arab Emirates
b INRA, UMR1083 Sciences pour l’Oenologie, Plateforme Polyphénols, 2, place

activities of plant samples to different extents. For instance, the Viala, 34060 Montpellier Cedex, France

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c 2013 Society of Chemical Industry
Polyphenolic compounds in dates
antioxidant properties. In the present study, we determined the
phenolic composition of date fruit seed.
Sample preparation
Date seeds from the Khalas variety were obtained from Al Ain
Dates Factory (Al Ain, UAE). Field experiments were carried out in
three consecutive growing seasons (2007–2008, 2008–2009 and
2009–2010) at the Al Ain Date factory, Al Ain, United Arab Emirates
(UAE) (24◦ 13 09 N; 55◦ 47 38 E). The average annual climatic
characteristics of the field experimental location were: annual
average temperature 29◦ C, annual average maximum temperature
36.5◦ C, annual average minimum temperature 22.2◦ C, annual
average wind speed 13.7 km h−1 , total rain days 15 days, total
annual precipitation of rain 60.88 mm, with void total days with
snow or tornado. The soil type was yellow–brown sandy. The
season (summer) of collecting tamr (fully ripe dates) is usually
spread over a period of 2–3 months. Samples were collected
randomly from tamr batches at the end of the season, with no
preference to size, colour, appearance or firmness. The seeds were
first soaked in water, washed to remove any adhering date flesh,
air-dried, and ground into coarse powder using a hammer mill.
The powder was further ground into fine material in a heavy-
duty grinder (IKA M 20 Universal Mill; IKA werke GmbH Co. KG,
Staufen, Germany) to pass through a 0.5 mm screen using an
Udy cyclone mill. The fine powder was then separated into two
fractions using sieves of 0.5 mm and 0.25 mm openings. The
powder from the 0.25 mm fraction was stored at −80◦ C pending
use for all the following analyses.
Extraction procedure
Extraction was performed in triplicate starting with 50 mg solid
material with a protocol adapted from that described by Mané
et al.13 Extraction was carried out using 1 mL MeOH and then
3 mL acetone–H2 O–Trifluoroacetic acid (TFA) (60:40:0.05, v/v/v).
After 1 h stirring and centrifugation, two aliquots (400 µL each)
of the supernatant were taken to dryness with a centrifugal evap-
orator Genevac Limited (IPSWICH, UK) operated at 35◦ C and 10
mbar. The first aliquot was dissolved in 400 µL MeOH–H2 O–HCl
(10:89:1, v/v/v) and analysed by ultra-high-performance
liquid chromatography–diode array detection–electrospray
ionisation–mass spectrometry (UPLC-DAD-ESI-MS). The second
one was dissolved in 200 µL of methanol–HCl (0.2 mol L−1 ) contain-
ing phloroglucinol (50 g L−1 ) and L-ascorbic acid (10 g L−1 ) and used
for determination of proanthocyanidin composition performed by
acid catalysed depolymerisation in the presence of phloroglucinol
(phloroglucinolysis) as described by Fournand et al.14 After heating
in a water bath at 50◦ C for 20 min, the phloroglucinolysis reaction
was stopped by adding an equal volume of sodium acetate 200
mmol L−1 and the reaction medium was analysed by UPLC-DAD-
ESI-MS. Preliminary extraction experiments performed using 50, 75
and 100 mg of solid material yielded identical values [(less than 10%
Relative Standard Deviation (RSD)] for all analysed compounds,
indicating that the solid-to-solvent ratio was appropriate.
Characterisation and quantification of polyphenolic
compounds
Chromatographic analysis was performed on a Waters Acquity
UPLC-DAD system (Waters, Milford, MA, USA), using an Acquity
BEH C18 column (10 × 1 mm i.d., 1.7 µm) (Waters). The mobile
phase consisted of water–formic acid (99:1, v/v) (solvent A) and
methanol–formic acid (99:1, v/v) (solvent B). The flow rate was
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0.08 mL min−1 and the oven temperature maintained at 35◦ C.
The elution program was as follows: isocratic for 1 min with 2%
B, 2–18% B (1–7 min), isocratic with 18% B (7–9 min), 18–30%
B (9–12 min), isocratic for 2 min with 30% B, 30–75% B (14–27
min), followed by washing and reconditioning of the column. The
injection volume was 2 µL.
ESI-MS/MS analyses were performed with a Bruker Daltonics
Amazon (Bruker, Darmstadt, Germany) mass spectrometer,
hyphenated to the UPLC-DAD system and equipped with
an electrospray source and an ion trap mass analyser. The
spectrometer was operated in the negative ion mode (capillary
voltage, 4.5 kV; end plate off set, −500 V; temperature, 200◦ C;
nebuliser gas, 10 psi and dry gas, 5 L min−1 ) and in the positive
ion mode (capillary voltage, 2.5 kV; end plate off set, −500 V;
temperature, 200◦ C; nebuliser gas, 10 psi and dry gas, 5 L min−1 ).
Collision energy for fragmentation used for MS2 experiments was
set at 1. Identifications were achieved on the basis of the retention
times, UV–visible and MS spectra. The data were compared with
those obtained with standard compounds and identifications of
date polyphenols available in the literature.15,16 Concentrations
were evaluated from peak areas at 280 nm (for protocatechuic
acid, flavan-3-ol monomers and oligomers and flavan-3-ol units
released by phloroglucinolysis), 320 nm (for hydroxycinnamic
acids) or 360 nm (for flavones and flavonols), using external
calibration curves established with the corresponding standard
or with a similar molecule (i.e. caffeic acid for hydroxycinnamic
derivatives, quercetin 3-glucoside for flavones and flavonols).
Phloroglucinolysis releases proanthocyanidin terminal units as
such and extension units as the corresponding phloroglucinol
derivatives, while maintaining their stereochemistry and eventual
substituents. Total flavan-3-ol content was calculated as the sum of
constitutive units released by phloroglucinolysis and their average
degree of polymerisation was calculated as the molar ratio of the
sum of all proanthocyanidin units to the sum of terminal units.
RESULTS
Identification of polyphenolic compounds
The UPLC chromatogram at 280 nm showed a large number of
compounds eluting throughout the profile and humps that can
be attributed to poorly resolved polymers (Fig. 1). Examination
of the UV–visible spectra allowed detection of different families
of polyphenolic compounds, namely phenolic acids and flavan-
3-ols (showing absorbance maxima around 280 nm), flavones
and flavonols (with two absorbance maxima at 250–260 nm and
340–360 nm), and hydroxycinnamic acids (absorbance maximum
at 325 nm with a shoulder around 280 nm). Comparison of
the profiles at 280 nm, 320 nm and 360 nm (Fig. 1) illustrates
the distribution of compounds between these three groups.
Each compound was further analysed by mass spectrometry
(Table 1). The peak eluted at 5.7 min (peak 1) could be identified as
protocatechuic acid on the basis of its retention time, UV spectrum
(λmax at 260 and 295 nm) and m/z value ([M − H]− at 153). A
series of peaks eluting between 7 and 13 min (peaks 2–8) could
be attributed to flavan-3-ol monomers [catechin (peak 4) and
epicatechin (peak 7)], dimers and trimers, detected respectively at
m/z = 289, 577 and 865 in the negative ion mode. A number of
tetramers, in lower concentration, were also detected.
The profile at 320 nm (Fig. 1B) shows the presence of four
hydroxycinnamic acid derivatives eluted at 12.6, 12.8, 13.5 and 14.8
min. The first (peak 9) and third (peak 11), detected at m/z = 335 in
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the negative ion mode and showing characteristic fragment ions
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2 5 6 Section A
3
4 7 8 280 nm

13
Section B
Intensity (mAU)

9 11
320 nm
10

14 Section C
360 nm
12
18
15 17 19
16

Figure 1. Chromatograms at 280 nm (section A), 320 nm (section B) and 360 nm (section C) of date seeds extract. Peak identifications are given in Table 1.

Table 1. Mass spectral characteristics of compounds identified in date seeds extract

Peak number Rt (min) λmax (nm) Mass spectrum MW Tentative identification

1 5.7 260, 295 [M − H]− : 153 154 Protocatechuic acid

2 7.6 278 [M − H]− : 577 578 Proanthocyanidin dimer
3 7.8 278 [M − H]− : 865 866 Proanthocyanidin trimer
4 8 278 [M − H]− : 289 290 Catechin
5 8.8 278 [M − H]− : 865 866 Proanthocyanidin trimer
6 9.7 278 [M − H]− : 577 578 Proanthocyanidin dimer
7 9.9 278 [M − H]− : 289 290 Epicatechin
8 12.1 278 [M − H]− : 1153 1154 Proanthocyanidin tetramer
9 12.6 326 [M − H]− : 335 fragments: 291, 179 336 Caffeoylshikimic acid
10 12.8 326 [M − H]− : 547 548 Hydroxycinnamic acid (unknown)
11 13.5 326 [M − H]− : 335 fragments: 291, 179 336 Caffeoylshikimic acid
12 14.1 340 [M − H]− : 593 fragments: 473, 353 594 Apigenin di-C-hexoside
13 14.8 321 [M − H]− : 581, fragment: 419 582 Hydroxycinnamic acid (unknown)
14 15.8 257, 354 [M − H]− : 543, fragment: 301 544 Quercetin derivative (O-hexosidesulfate)
15 17.0 257, 354 [M + H]+ : 449, fragment: 287 448 Kaempferol hexoside
16 18.0 263, 349 [M − H]− : 535 536 Flavone derivative
17 18.3 356 [M − H]− : 463, fragment: 301 464 Quercetin hexoside
18 20.0 349 [M − H]− : 461, fragment : 299 462 Flavone hexoside
19 20.4 349 [M − H]− : 567, fragment: 299 568 Flavone rhamnosylhexoside

at 291 (loss of 44 a.m.u: COO− ), and 179 (caffeic acid) correspond to
caffeoylshikimic acid isomers. No identification could be proposed
for the other two (peaks 10 and 13), detected at m/z 547 and 581,
respectively. A series of compounds eluted between 14 and 21
min (Fig. 1C) exhibited UV–visible spectra characteristic of flavone
and flavonol derivatives. The compound eluted at 14.1 min (peak
12) was detected at m/z = 493 in the negative ion mode and
showed fragment ions at 473 and 353 a.m.u corresponding to
two successive losses of 120 mass units. Its UV–visible spectrum
is similar to that of apigenin and the neutral loss of 120 mass
units is characteristic of flavonoid C-hexosides. The compound
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Hong et al.16 Peaks eluted at 15.8 min (paek 14) and 18.3 min
(paek 17) were detected at m/z = 543 and m/z = 463, respectively,
and give identical fragment ions at 301, which may correspond to
quercetin aglycone. The latter may correspond to a quercetin O-
hexoside (loss of 162 a.m.u = hexoside) while the former could be
a quercetin O-hexoside sulfate, described earlier.16 The compound
eluted at 17 min (peak 15) detected at m/z = 449 in the positive
ion mode (fragment ion at 287, loss of 162 mass units) may be a
kampferol O-hexoside. The peak eluted at 18 min (peak 16) was
detected at m/z = 535 and may correspond to flavone derivative.
Peaks eluted at 20 and 20.4 min (peaks 18 and 19), were detected

may thus correspond to apigenin di-C-hexoside, as proposed by at m/z = 461 and 567, respectively, and yielded the same fragment

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Figure 2. Chromatograms at 280 nm after depolymerisation of date seeds extract. Identification of the main peaks: (1) epicatechin phloroglucinol adduct,
(2) catechin, (3) epicatechin.

ion at m/z = 299, in the negative ion mode. They may thus be a
O-hexoside (loss of 162 mass units) and a O-rhamnosylhexoside (or
O-hexoside, O-rhamnoside) (loss of 162 + 146 mass units) of the
same aglycone, presumably a flavone (chrysoeriol or diosmetin)
on the basis of its λmax at 349 nm.
HPLC analysis after phloroglucinolysis (Fig. 2) allowed detection
of three major peaks, corresponding to epicatechin phloroglucinol
adduct (arising from extension units of proanthocyanidin
oligomers and polymers) (peak 1), catechin (peak 2) and
epicatechin (peak 3) (initially present as monomers and as
terminal units of proanthocyanidins), confirming the presence
of proanthocyanidins (already detected as oligomers).
(expressed as epicatechin equivalent) were 1.655 ± 0.015 g
kg−1 , flavones or flavonols (expressed as quercetin 3-glucoside
equivalent) were 0.072 ± 0.005 g kg−1 , while hydroxycinnamic
acids (expressed as caffeic acid equivalent) were 0.388 ± 0.020
g kg−1 . Flavan-3-ols were the most abundant components. The
total amount of flavan-3-ols calculated after depolymerisation
was 50.18 ± 1.360 g kg−1 with 46.800 ± 1.012 g kg−1 epicatechin
and 3.380 ± 0.349 g kg−1 catechin and an average degree of
polymerisation of 10.4) (Table 3). Therefore, the total amount of
flavonoids and phenolic compounds in date seed was about 50.72
g kg−1 .

Quantities of the polyphenolic compounds DISCUSSION

The concentrations of individual polyphenolic compounds were
estimated from their peak areas. The total amount of individual
polyphenols was found to be 2.194 ± 0.040 g kg−1 date seeds
before depolymerisation (Table 2). Protocatechuic acid was
0.079 ± 0.005 g kg−1 , flavan-3-ol monomers and oligomers
This study is the first most comprehensive investigation of
flavonoid and phenolic compound profile and quantities in
date seeds. The UPLC-DAD-ESI-MS analyses confirmed that date
seeds are characterised by a high content of polyphenols, close
to 51 g kg−1 , which is higher than the carbohydrate content

Table 2. Concentrations of the major flavonoids and phenolic compounds detected in the date seeds extract before depolymerisation

Family Compound Quantity (g kg−1 )

Phenolic acids Protocatechuic acid (mg g−1 ) 0.079 ± 0.005

Flavan-3-ols Proanthocyanidin dimer B1 (mg g−1 epicatechin equivalent) 0.434 ± 0.011
Proanthocyanidin trimer 1 (mg g−1 epicatechin equivalent) 0.577 ± 0.009
Catechin (mg g−1 ) 0.296 ± 0.020
Proanthocyanidin dimer B2 (mg g−1 epicatechin equivalent) 0.124 ± 0.006
Proanthocyanidin trimer 2 (mg g−1 epicatechin equivalent) 0.036 ± 0.007
Epicatechin (mg g−1 ) 0.188 ± 0.028
Flavones and flavonols Apigenin derivative (mg g−1 quercetin 3-O-glucoside equivalent) 0.005 ± 0.001
Quercetin derivative (mg g−1 quercetin 3-O-glucoside equivalent) 0.034 ± 0.003
Flavone or flavonol (mg g−1 quercetin 3-O-glucoside equivalent) 0.011 ± 0.001
Flavone derivative (mg g−1 quercetin 3-O-glucoside equivalent) 0.021 ± 0.001
Hydroxycinnamic acids Caffeoyl shikimic acid (mg g−1 caffeic acid equivalents) 0.061 ± 0.007
Unknown (hydroxycinnamic acid derivative) (mg g−1 caffeic acid equivalents) 0.060 ± 0.009
Caffeoyl shikimic acid (mg g−1 caffeic acid equivalents) 0.045 ± 0.001
Unknown (hydroxycinnamic acid derivative) (mg g−1 caffeic acid equivalents) 0.222 ± 0.005
Total 2.194 ± 0.040

Means of triplicate ± SD are presented.

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Table 3. Proanthocyanidin composition of date seeds extract after
depolymerisation
Item Concentration (g kg−1 )
Quantity 50.180 ± 1.360
Epicatechin 46.800 ± 1.012
Catechin 3.380 ± 0.349
(39.400 ± 5.300 g kg−1 ) and similar to the protein content
(58.400 ± 0.100 g kg−1 ) previously measured in date seeds of
the same Khalas variety.4 The main class of compounds was by
far the flavan-3-ols in both their monomeric and polymeric forms,
representing almost 99% of total polyphenols. The amount of total
phenolic compounds before depolymerisation was found to be
2.194 ± 0.040 g kg−1 date seed. The flavan-3-ols were distributed
as 46.800 ± 1.012 g kg−1 of epicatechin and 3.380 ± 0.349 g kg−1
of catechin.
Based on these values, the date seed indeed constitutes one of
the highest sources of total polyphenols, surpassing tea, grapes,
flaxseed, nut seeds and even date flesh.6,17 – 19 Total phenolic
contents in date seeds are similar to values reported for grape
seeds, ranging between 50 and 100 g kg−1 fresh weight.13
Flaxseeds – which are at the ninth rank in the database of
polyphenolic content of food sources, with an amount of 15.28 g
kg−1 – are largely below date seeds.17 Only one previous study
related to polyphenols content was conducted in date seeds,
focusing only on phenolic acids.20 The phenolic acid content
identified in our work is lower (0.079 ± 0.005 g kg−1 ) than the
amount obtained in above-mentioned study (0.490 ± 0.029 g
kg−1 seeds) and additional compounds were identified including
coumaric and caffeic acids. The differences can be related to
the varieties of dates which were considered. Since it has been
clearly shown in many other plant seeds like grape seeds, that the
identification and estimation of phenolic components depends
on the method used, especially the type of solvent, an effect of the
methodology cannot be ruled out.20,21 Besides, identification in
the aforementioned work20 was based on comparison of retention
times with those of commercial standards, which can be very
misleading especially with a profile of such complexity. Moreover,
coumaric and caffeic acids have been identified as metabolites of
catechin after intestinal metabolisation and it can be hypothesised
that these compounds were formed with the extraction conditions
used in this work. Even though the most famous variety of dates
in the UAE was considered, however, an impact of the cultivar
cannot be ruled out.22,23 Besides, other factors such as maturity
and drying method may have an impact on the concentration of
polyphenols as it has already been shown in other seeds, such
as grape seeds.24,25 The determination of the polyphenolic profile
and the estimation of the amount of each of them is of great
importance in terms of future potential value of date seed as
functional ingredient protecting against several chronic diseases
with mechanisms of action possibly involving antioxidant, anti-
inflammatory, and vasoactive properties. As in grape seeds,18
flavan-3-ols were found to be the most abundant polyphenols
in date seeds. Interestingly, flavan-3-ols have been described
in the literature with potentially the highest beneficial health
effects among polyphenols. Epidemiological studies suggest
that proanthocyanidins, especially, could strongly reduce the
risk of cardiovascular diseases. Apart from their antioxidant
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activity, one of the mechanisms by which they could exert
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H M Habib et al.
cardiovascular protection is by improving lipid homeostasis.26
Experimental and clinical studies indicate that daily intake of
several proanthocyanidin-rich foods could improve endothelial
dysfunction and decrease vascular oxidative stress associated
with major cardiovascular risk factors such as hypertension.
Interestingly, proanthocyanidins were identified as the principal
vasoactive polyphenols,27 and they were the most abundant
components in our date seed extract.
The authors have already tested date seeds as ingredient
in developing a functional food product. The first results
showed great nutritional and antioxidant properties of the final
product whose toxicity is also under investigation in animals.28
Nonetheless, no toxicity is expected since a previous study
conducted in rat for 30 days, by using a diet with 7 and 14% of date
seed powder reported no adverse effects of date seed powder on
organ function, lipid profile, protein metabolism, haematological
parameters, and body weight.12
Since it is recognised that the most abundant polyphenols in the
food are not necessarily the most abundant bioactive metabolites
in the target tissues, prior to further development of functional
food containing date seed, bioavailability of polyphenols and their
metabolites have to be studied. Interactions of polyphenols with
the food matrix cannot be excluded, and it is well established that
polyphenols undergo transformations, methylation, sulfation or
glucuronidation in the intestine and liver before release into the
bloodstream.29
Nonetheless, previous results suggest that catechins and
flavanones, some of the major compounds identified in date
seeds, are among the best absorbed polyphenol and recent studies
conducted with green tea and apple showed that polyphenols and
their metabolites were found in great amount in plasma and urine
after oral ingestion in humans.30,31 This is in favour of a good
bioavailability of polyphenols from date seeds.
CONCLUSION
The present work has described findings that are essential for
future studies in date seeds. They represent the necessary basic
information to a better characterisation of the polyphenolic profile
of date seeds and to a better understanding of health benefits of
date seeds.
Even with the inevitable limitation linked to the unfeasibility of
quantifying all the identified polyphenols, a reasonably detailed
quantitative profile of polyphenols was provided for date seed
extract. Date seeds, which are generally considered a by-product,
are probably one of the richest edible sources of polyphenolic
compounds. This is in favour of a high antioxidant capacity for
date seeds, which makes them a very interesting and innovative
potential ingredient to increase the daily antioxidant intake with
natural ingredients.
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