ArticlePDF Available

Whole grain oats, more than just a fiber: Role of unique phytochemicals

Authors:
  • North Carolina Agricultural and Technical State University, North Carolina Research Campus, Kannapolis, NC, USA

Abstract and Figures

Oats are a good source of soluble dietary fiber, especially β-glucan, which has outstanding functional and nutritional properties. β-Glucan is considered to be the major active component of oats because of its cholesterol-lowering and anti-diabetic effects. However, the nutritional benefits of oats appear to go beyond fiber to bioactive phytochemicals with strong antioxidant and anti-inflammatory effects. In this review, we summarize current knowledge on the chemistry, stability, bioavailability, and health effects of two unique phytochemicals in oats, avenanthramides (AVAs) and avenacosides A and B. We conclude that studies on the beneficial effects of AVAs and avenacosides A and B are still in their infancy, and additional health benefits of these unique oat components may yet be identified. This article is protected by copyright. All rights reserved.
Content may be subject to copyright.
Mol. Nutr. Food Res. 61,7, 2017, 1600715 (1 of 12) 1600715
DOI 10.1002/mnfr.201600715
REVIEW
Whole grain oats, more than just a fiber: Role of unique
phytochemicals
Shengmin Sang1and YiFang Chu2
1Laboratory for Functional Foods and Human Health, Center for Excellence in Post-Harvest Technologies, North
Carolina Agricultural and Technical State University, North Carolina Research Campus, Kannapolis, NC, USA
2Quaker Oats Center of Excellence, PepsiCo R&D Nutrition, Barrington, IL, USA
Received: August 15, 2016
Revised: October 11, 2016
Accepted: December 30, 2016
Oats are a good source of soluble dietary fiber, especially -glucan, which has outstanding
functional and nutritional properties. -Glucan is considered to be the major active component
of oats because of its cholesterol-lowering and antidiabetic effects. However, the nutritional
benefits of oats appear to go beyond fiber to bioactive phytochemicals with strong antioxi-
dant and anti-inflammatory effects. In this review, we summarize current knowledge on the
chemistry, stability, bioavailability, and health effects of two unique phytochemicals in oats,
avenanthramides, and avenacosides A and B. We conclude that studies on the beneficial effects
of avenanthramides and avenacosides A and B are still in their infancy, and additional health
benefits of these unique oat components may yet be identified.
Keywords:
Avenacosides / Avenanthramides Health effect / Oats / Phytochemicals
1 Introduction
Cereal-based food products have been the basis of the human
diet for thousands of years, and contribute about 50% of di-
etary fiber intake in Western countries. Increased whole grain
consumption is inversely associated with the risk for devel-
oping certain diet-related disorders such as type 2 diabetes,
obesity, cancer, and cardiovascular disease [1,2]. Oats (Avena
sativa L.) have been cultivated for more than 2000 years in
various regions throughout the world. It is a multifunctional
crop considered to be nutritionally superior to many other
unfortified cereals. Oats are commonly consumed as whole
grains, which provide important nutrients such as proteins,
unsaturated fatty acids, vitamins, and minerals [3]. Numer-
ous laboratory and clinical studies have demonstrated that the
Correspondence: Dr. Shengmin Sang, Laboratory for Functional
Foods and Human Health, Center for Excellence in Post-Harvest
Technologies, North Carolina Agricultural and Technical State
University, North Carolina Research Campus, 500 Laureate Way,
Kannapolis, NC 28081, USA
E-mail: ssang@ncat.edu; shengminsang@yahoo.com
Abbreviations: AP-1, activator protein 1; AUC, area under the
curve; AVA, avenanthramide; dAA, 26-desglucoavenacoside A;
DPPH, 2,2-diphenyl-L-picrylhydrazyl; HAEC, human aortic en-
dothelial cell; HHT, hydroxycinnamoyl CoA:hydroxyanthranilate
N-hydroxycinnamoyl transferase; HO-1, heme oxygenase-1;
MAPK, mitogen-activated protein kinase; Nrf2, nuclear factor
erythroid-2 related factor 2; NF-B, nuclear factor-kappa B; SMC,
smooth muscle cell; UV, ultraviolet
consumption of oat-based products can lower serum choles-
terol levels, reduce glucose uptake, and decrease plasma in-
sulin response [3–6]. These nutritional benefits of oats have
attracted the attention of scientific researchers and the gen-
eral public. As a result, the food industry has increased its use
of oats as an ingredient in various food products, including
breakfast cereals, beverages, breads, and infant foods.
Oats are a good source of soluble dietary fiber, especially
-glucan, which has outstanding functional and nutritional
properties. -Glucan is considered to be the major active
component of oats because of its cholesterol-lowering and
antidiabetic effects [7]. However, oats supply more than just
fiber. This grain contains numerous bioactive phytochem-
icals, which are structurally diverse secondary metabolites
synthesized by plants [7]. For example, oats are a good source
of phenolic acids, flavonoids, carotenoids, vitamin E, and phy-
tosterols [7–9]. In addition, oats produce two unique types of
phytochemicals: avenanthramides (AVAs) [10] and steroidal
saponins [11]. In this review, we summarize current knowl-
edge on the chemistry and health effects of these two unique
phytochemicals.
2 Avenanthramides
2.1 Chemistry
AVAs are phenolic alkaloids found exclusively in oats among
the cereals. They are a type of phytoalexin that are produced
C2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.mnf-journal.com
1600715 (2 of 12) S. Sang and Y. F. Chu Mol. Nutr. Food Res. 61,7, 2017, 1600715
in response to pathogens [12]. The biosynthesis of AVAs re-
sults from the acylation of anthranilic acid and derivatives
by the CoA thioester of cinnamic acid catalyzed by hydrox-
ycinnamoyl CoA:hydroxyanthranilate N-hydroxycinnamoyl
transferase (HHT) [13]. These compounds are substituted
N-cinnamoylanthranilic acids consisting of anthranilic acid
and cinnamic acid moieties. The AVAs differ in the substitu-
tion pattern on the two moieties.
AVAs were first purified from oat groats and hulls
by Collins, who assigned an alphabetic descriptor to
each AVA congener [14, 15]. Dimberg developed a more
systematic nomenclature, assigning the anthranilate deriva-
tives a number and the accompanying cinnamate deriva-
tives the following letters: c for caffeic acid, f for fer-
ulic acid, and p for p-coumaric acid [16]. Dimberg’s
alphanumeric nomenclature is used in this review. The an-
thranilic acid moiety consists of one anthranilic acid (1), 5-
hydroxyanthranilic acid (2), 5-hydroxy-4-methoxyanthranilic
acid (3), or 4-hydroxyanthranilic acid (4). The cinnamic acid
moiety consists of cinnamic acid (a), caffeic acid (c), ferulic
acid (f), p-coumaric acid (p), or sinapic acid [17–20]. The pre-
dominant AVAs found in oats are 2c, 2f, and 2p; however,
at least 25 different AVAs have been detected in oats, al-
though some of these have not been purified from oats and
are present in very low concentrations [15, 20, 21]. If the cin-
namic moiety consists of avenalumic acid derivatives [22],
which have an additional double bond compared with cin-
namic acid derivatives, a letter d is added to the name of the
AVA (e.g., 2cd,2f
d,and2p
d) (Fig. 1). In addition, we recently
purified a novel glucoside derivative of 2c and identified a
series of AVA-glucoside derivatives from oat products (un-
published data) (Fig. 1).
The total concentration of AVAs in oat grains reported in
the literature varies widely from 2 to 289 mg/kg [9,20,23–26].
Most of the AVAs present in oats are found in oat groats,
with the highest concentration in the bran. However, these
compounds are also present in the hulls and leaves [15, 27].
The concentration of AVAs in oat leaves ranges from 5 to 120
mg/kg, with large variations between cultivars and cultiva-
tion conditions, and especially high concentrations in leaves
treated with elicitors [27–29]. The AVA content in the oat
grain also varies according to cultivar, year, location, cul-
tivation conditions, and interactions between these factors
[23,25,26]. The AVA content is negatively affected by high ni-
trogen fertilization but does not differ between conventional
or organic cropping systems [9]. The level of AVA increases
throughout grain maturation [29].
Dimberg et al. examined the effects of long-term storage,
heat treatment, pH, and ultraviolet (UV) light on the stabil-
ity of oat AVAs (2c, 2f, and 2p) [24, 30]. The results showed
that long-term storage does not significantly affect AVA con-
centration [24]. In addition, the AVAs 2f and 2p and their
corresponding cinnamic acids, ferulic acid and p-coumaric
acid, do not appear to be sensitive to pH change at room
temperature over a 24-h period, although AVA 2f and ferulic
acid are less stable at higher temperatures at pH 7 and 12
[30]. In contrast, 2c and caffeic acid degrade completely in
an alkaline solution, and the instability of 2c and caffeic acid
is even more pronounced when pH-treated samples are also
heat treated [30]. Dimberg et al. found that UV irradiation
causes the trans–cis isomerization of cinnamic acids but not
AVAs [30], in contrast to Collins et al., who reported sim-
ilar isomerization of AVAs and cinnamic acids exposed to
UV light [15, 31]. Concentrations of AVAs were also studied
before and after processing in various food products contain-
ing oats (e.g., breads, muffins, fresh pasta, and macaroni)
[30]. The results showed that the concentration of total AVAs
(2c, 2p, and 2f) increased in all food products tested, pos-
sibly through de novo synthesis, release of insoluble bound
forms, increased extractability, or a combination of these fac-
tors. Bryngelsson and co-workers investigated the effects of
commercial hydrothermal processes (steaming, autoclaving,
and drum drying) on AVA concentrations in oats [32]. They
reported that 2p decreased during the processing of rolled
oats, whereas 2c and 2f levels remained stable. The AVAs 2c
and 2p decreased during the autoclaving of oat grains, and
all three AVAs decreased during the drum drying of milled
rolled oats. This loss of AVAs may be decreased by refinement
of the processing methods, such as lower temperature and
pH during heat treatment. Alternatively, these losses could
be offset by processing steps that increase the AVA levels in
the raw material. For centuries, cereal seeds have been ger-
minated after steeping in water to soften the kernel structure,
increase nutrient content, and decrease antinutritional com-
pounds. Bryngelsson et al. compared AVA concentrations
and enzyme activity of HHT in oats that were dry or steeped,
milled or unmilled, and raw or heat treated [13]. Their results
showed that steeping intact raw groats increased AVA con-
centrations in a time- and temperature-dependent manner,
with maximum concentrations observed after 10 h of steep-
ing at 20C. In addition, AVA concentration and HHT activity
were positively correlated during the steeping of intact groats
at 8 and 20C, suggesting that this increase in AVAs was due
to de novo synthesis. However, AVA levels also increased in
the steeped heat-treated oats, which lack HHT activity; this
increase may be due to the release of bound forms during
heat treatment.
2.2 Bioavailability and biotransformation
Few studies have evaluated the uptake of AVAs. In one study
[33], 0.25 g oat bran phenol-rich powder containing 0.63 mol
2p and 0.49 mol 2f was delivered to hamsters as a slurry via
stomach gavage, and blood was collected at 0, 20, 40, 60, 80,
and 120 min. Maximum plasma concentrations (Cmax)ofAVA
2p and 2f and the major phenolic acids in oats appeared at 40
min. Cmax values of 2p and 2f were 0.04 ±0.03 and 0.03 ±
0.02 mol/L, respectively; however, the apparent bioavailabil-
ity of the AVAs was only 5% of the least bioavailable phenolic
acid (vanillic acid) and 1.3% of the most bioavailable phenolic
acid (p-coumaric acid).
C2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.mnf-journal.com
Mol. Nutr. Food Res. 61,7, 2017, 1600715 (3 of 12) 1600715
Figure 1. Structures of the major oat avenanthramides and tranilast.
A study conducted by the same group evaluated the
pharmacokinetics of AVAs 2p, 2f, and 2c in humans after
consumption of an AVA-enriched mixture containing 154
mol/g 2p, 109 mol/g 2f, and 117 mol/g 2c [34]. This
AVA-enriched mixture (0.5 or 1.0 g) was given to six healthy
older adults (three men and three women) in skim milk. A
baseline blood sample was obtained, and blood samples were
collected at 15, 30, and 45 min and at 1, 2, 3, 5, and 10 h after
drinking the test beverage. The Cmax values of 2p, 2f, and 2c
were 166.7–1002.2, 49.3–153.5, and 29.6–328.1 mol/g, re-
spectively, after consuming the beverage containing 1.0 g of
the AVA-enriched mixture [34]. These Cmax values were 231%,
627%, and 115% larger, respectively, than after consumption
of the 0.5 g dose. The Cmax of 2p at both doses was at least
twofold larger than those of 2f and 2c. For all three AVAs,
the time at which Cmax was observed (tmax) was approximately
2 h, but the tmax of 2f was shorter (1.5 h) after consuming
the 1.0 g dose. For each AVA, there was no difference in the
plasma half-life (t1/2) between the two doses; however, there
were differences between the three AVAs after the 0.5 g dose,
with a longer t1/2 for 2f compared with 2p. For all three AVAs,
the area under the curve (AUC) after the 1.0 g dose was two-
to eightfold greater than the AUC after the 0.5 g dose, even
though the difference in dose was only onefold. The AUC
of 2p was more than twofold larger than that of 2f and 2c
after the 1.0 g dose, and more than sevenfold larger than 2f
after the 0.5 g dose. The relative bioavailabilities of the three
AVAs were estimated as the ratio of the AUC to the AVA
concentration in the test beverage. The bioavailability of 2p
was considerably higher than those of 2f and 2c (9.7, 4.4, and
4.2, respectively, after the 1.0 g dose, and 5.1, 1.0, and 3.8,
respectively, after the 0.5 g dose).
Koenig et al. evaluated the tissue distribution of AVAs in
rats after ingestion of a mixture containing 20 mg/kg body
weight of each of the three major AVAs (2c, 2f, and 2p) [35].
They analyzed AVA levels in plasma, liver, heart, and gas-
trocnemius at 0, 2, 4, and 12 h (n=6 at each time point)
and found that AVAs circulate in the blood before reaching
peripheral tissues, where they are differentially taken up by
the organs [35]. All three AVAs were detected mainly in their
phase II conjugated forms. Consistent with findings in ham-
sters and humans, 2p was the most bioavailable AVA in rat
plasma. However, concentration of 2f was highest in the liver
and heart, and the concentration of 2c was highest in muscle.
Peak plasma AVA concentrations occurred 1 h postgavage in
rats, 2 h after ingestion in humans, and 40 min after inges-
tion in hamsters in the studies of Chen et al. Overall, AVA
concentrations were considerably lower in muscle than in the
liver and heart up to 12 h postgavage.
Our recent publication on the metabolism of AVA 2c
in mice and by the human gut microbiome was the first
study on the biotransformation of AVAs [36]. Mice housed in
metabolic cages received AVA 2c (200 mg/kg) by oral gavage,
and urine and fecal samples were collected over 24 h and
C2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.mnf-journal.com
1600715 (4 of 12) S. Sang and Y. F. Chu Mol. Nutr. Food Res. 61,7, 2017, 1600715
Figure 2. Major metabolic pathways of 2c.
analyzed by LC/MS. We found that 2c was extensively me-
tabolized in mice, with a total of eight metabolites (phase II
conjugated) detected in the urine. Only one major metabolite
(in its free form) was found in feces. Upon the elucidation
of the structures of these metabolites, three major metabolic
pathways were proposed (Fig. 2). Because of its catechol
structure, 2c is a substrate for catechol-O-methyltransferase
to generate the methylated metabolite 2f (M8). The C7–C8
double bonds of 2c and 2f can be reduced to generate
the metabolites DH-2c (M6) and DH-2f (M7). In addition,
cleavage of the amide bond is another major metabolic
pathway of 2c. For example, cleavage of its amide bond leads
to the formation of M1 and M3. Metabolites M1 and M5 are
generated by the cleavage of M6, and metabolites M1 and
M4 are generated by the cleavage of M7.
We also examined 2c metabolism by the highly complex
microbial ecosystem of the human colon, which contains
1012 microorganisms/g gut content [37]. Results of in vitro
fecal batch fermentation, using human fecal microbes
collected from six healthy individuals, showed that 2c was
progressively degraded by the microbes over 120 h. DH-2c
(M6), CA (M3), and DH-CA (M2) were identified as the
major microbial metabolites of 2c, indicating that human
fecal microbes are able to reduce the double bond and cleave
the amide bond of 2c. Another important finding was the
interindividual variability in 2c metabolism. For example,
the microbes of some subjects did not produce or produced
only low levels of the metabolite DH-2c, whereas the
microbes of other subjects almost completely metabolized
2c by 120 h, suggesting that an individual’s gut microbiota
composition plays a crucial role in the ability to metabolize
2c. Further mechanistic studies demonstrated that AVAs
are metabolized to the double bond reduced metabolites
mainly by gut microbiota rather than by liver and intestinal
microsomes and S9 fraction (unpublished data).
2.3 Bioactivities with implication for health
2.3.1 Antioxidant effects
Numerous clinical and preclinical studies have demonstrated
the antioxidant properties of AVAs (Fig. 3). The previously
mentioned study by Chen et al. [32] found that consuming
skimmilkcontaining1gofanAVA-enrichedmixturesignif-
icantly increased plasma levels of reduced glutathione at 15
min (21% over baseline) and increased the AUC of reduced
glutathione [34]. Another randomized study of 120 healthy
individuals who consumed oat AVA capsules (3.12 mg) or
placebo daily for 1 month showed significant differences in
plasma lipid peroxide levels and antioxidant status [38]. In
individuals taking the AVA supplements, levels of serum
superoxide dismutase increased by 8.4%, levels of reduced
glutathione increased by 17.9%, and malondialdehyde levels
decreased by 28.1%. In a more recent study, subjects ate two
cookies made from oat flour daily for 8 weeks. Those who
consumed cookies containing 9.2 mg AVAs showed signifi-
cantly higher total plasma antioxidant capacity and erythro-
cyte superoxide dismutase activity compared to subjects in
the control group, whose consumption of AVAs was 23-fold
lower [39].
A study investigating the antioxidant activity of AVAs also
found that rats fed AVAs (0.1 g/kg for 50 days) had higher
superoxide dismutase activity in the deep portion of the vas-
tus lateralis muscle, liver, and kidney and higher glutathione
peroxidase activity in the heart and deep portion of the vastus
lateralis muscle compared to control animals [40]. In addi-
tion, AVAs lower the levels of exercise-induced reactive oxy-
gen species [40,41]. In mice, injection of an AVA-rich extract
reverses D-galactose-induced oxidative stress by upregulating
gene expression and activity of antioxidant enzymes (e.g.,
superoxide dismutase) [42]. In addition, AVAs act synergisti-
cally with vitamin C to protect against low-density lipoprotein
oxidation in hamsters and humans [33].
Results of in vitro studies showed that the antioxidant
capacity of AVA 2f is approximately 20% greater than that
of -tocopherol, as assessed by oxygen consumption in a
linoleic acid system [20,43]. The antioxidant activities of AVA
2c, 2f, and 2p were also determined by testing their abil-
ity to inhibit -carotene bleaching and react with the free
radical 2,2-diphenyl-L-picrylhydrazyl (DPPH) [44]. Each AVA
exhibited antioxidant activity in both in vitro assays, with 2c
showing the strongest antioxidant capacity of the three com-
pounds. A structure–antioxidant activity relationship study
found that synthetic AVAs containing caffeic or sinapic
acid were more effective antioxidants than those containing
C2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.mnf-journal.com
Mol. Nutr. Food Res. 61,7, 2017, 1600715 (5 of 12) 1600715
Figure 3. Bioactivities of
avenanthramides.
ferulic or p-coumaric acid [18]. In addition, a recent study in-
vestigated the antioxidant capacities of 2c, 2f, and 2p against
peroxyl radicals, hydroxyl radicals, superoxide anions, singlet
oxygen, and peroxynitrite [43]. This study also found that 2c
had the highest total antioxidant capacity of the three AVAs,
although the antioxidant activity against specific reactive oxy-
gen species varied.
Despite evidence from in vivo and in vitro studies demon-
strating the strong antioxidant capacity of AVAs, the underly-
ing mechanisms for these effects are largely unknown. One
potential mechanism is related to the number and positions
of hydroxyl groups on the anthranilic acid and cinnamic acid
moieties. Previous in vitro studies demonstrated that the trap-
ping of reactive species accounts for the ability of AVAs to
combat oxidative stress [43, 45, 46]. One study evaluated the
antioxidant activities of AVAs and the drug tranilast (Fig. 1),
which is structurally similar to AVAs but has no hydroxyl
groups [45]. Tranilast showed no antioxidant activity in the
DPPH assay or the ferric reducing antioxidant potential as-
say, suggesting that the hydroxyl groups of AVAs are involved
in free radical trapping. The particularly strong antioxidant
capacity of AVA 2c appears to be due to the ortho-hydroxyl
group on the cinnamic acid moiety [43–46]. However, the an-
thranilic acid moiety might be as important as the cinnamic
acid moiety for antioxidant activity [45,46]. Fagerlund and co-
workers found that conjugation across the amide bond of the
AVAs was also important for trapping DPPH, although this
feature is less important than the hydroxyl groups on the two
aromatic rings [46].
Our recent study suggested a novel mechanism by which
AVAs activate cellular defense pathways against oxidative
stress that involves the ,β-unsaturated carbonyl moiety
[47]. The transcription factor nuclear factor erythroid-2 re-
lated factor 2 (Nrf2) regulates the expression of molecules
that protect against oxidative and electrophilic stress [48].
Under basal conditions, Nrf2 is continuously degraded by
the 26S proteasome via Kelch-like ECH-associated protein 1
mediated ubiquitination. However, in response to oxidative
and electrophilic stress, Nrf2 detaches from Kelch-like ECH-
associated protein 1, migrates to the nucleus, and binds to
the antioxidant response element sequence to activate tran-
scription of genes encoding cytoprotective and detoxifying
enzymes such as heme oxygenase-1 (HO-1) [49–51]. The ,β-
unsaturated carbonyl groups of AVAs act as Michael acceptors
for nucleophilic attack. Therefore, we hypothesized that AVAs
are able to activate the Nrf2 defense system against oxidative
stress. This hypothesis was supported by our observations
that AVAs significantly increase HO-1 expression in HK-2
cells in a dose- and time-dependent manner, and this upreg-
ulation of HO-1 expression is mediated by Nrf2 translocation
and reactive oxygen species. Pretreatment with the kinase in-
hibitors PD98059, LY294002, and SB202190 does not inhibit
AVA-induced HO-1 expression, suggesting that this effect
is not mediated by phosphoinositide 3-kinase or mitogen-
activated protein kinase (MAPK). Moreover, hydrogenation
of the double bond of the ,β-unsaturated carbonyl moiety
completely blocks AVA-induced HO-1 expression, indicating
that the ,β-unsaturated carbonyl moiety is important for
C2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.mnf-journal.com
1600715 (6 of 12) S. Sang and Y. F. Chu Mol. Nutr. Food Res. 61,7, 2017, 1600715
antioxidant activity and that the hydroxyl groups are not in-
volved in the activation of the Nrf2 pathway. Taken together,
these results show that both the hydroxyl groups and the
,β-unsaturated carbonyl moiety are crucial for the antioxi-
dant properties of AVAs, and they act directly or indirectly to
scavenge reactive oxygen species.
2.3.2 Anti-inflammatory effects
The AVAs are also thought to exert anti-inflammatory activ-
ities, as demonstrated by in vitro and in vivo studies. In a
randomized double-blind trial [39], women aged 50–80 years
consumed two cookies made up of oat flour containing either
9.2 mg AVAs or 0.4 mg AVAs (control) daily for 8 weeks.
Before and after the 8-week dietary regimen, inflammation
and antioxidant status was evaluated after exercise (down-
hill walking on a treadmill). Blood samples were collected
at rest, 24 h after exercise, and 48 h after exercise. The re-
sults showed that the AVA supplementation (9.2 mg) signif-
icantly decreased the systemic inflammatory response of the
women, as assessed by neutrophil respiratory burst at 24 h
and C-reactive protein level at 48 h. AVA supplementation
also suppressed proinflammatory cytokine production, as as-
sessed by plasma IL-1concentration and mononuclear cell
nuclear factor-kappa B (NF-B) binding. In a similar study
[52], the same authors evaluated the effect of AVA supple-
mentation on the systemic inflammatory response of younger
women (18–30 years old) after exercise (downhill running
on a treadmill). The results showed significantly decreased
neutrophil respiratory burst, NFB activation, plasma IL-6
concentration, and erythrocyte glutathione peroxidase activ-
ity and increased reduced glutathione levels. Thus, long-term
AVA supplementation appears to be a useful dietary strategy
to reduce inflammation after demanding physical exercise in
both younger and older women.
Modulation of the inflammatory response by AVAs ap-
pears to be mediated through interaction with molecular and
signaling pathways in cells. Liu et al. investigated the anti-
inflammatory and antiatherogenic effects of oat AVAs in the
human aortic endothelial cell (HAEC) culture system. Prein-
cubation of HAECs with a mixture of AVAs extracted from
oats (20 or 40 mg/mL) for 24 h significantly suppressed IL-
l-stimulated expression of intracellular adhesion molecule-
l, vascular cell adhesion molecule-1, and E-selectin, thereby
decreasing the production of inflammatory cytokines and
chemokines such as IL-6, IL-8, and monocyte chemoattrac-
tant protein 1 [53]. Further mechanistic studies suggested
that the decrease in expression of proinflammatory endothe-
lial cytokines was mediated, at least in part, by inhibiting
NF-B activation (blocking phosphorylation of IKK and IB)
and suppressing proteasome activity [54]. Furthermore, AVAs
inhibited NF-B-dependent gene expression induced by TNF
receptor associated factor-2 and factor-6 and NF-B-inducing
kinase but did not inhibit the binding of NF-B to DNA [54].
2.3.3 Antiatherosclerosis effects
Besides the anti-inflammatory effects, AVAs appears to pre-
vent atherosclerosis by inhibiting the proliferation of smooth
muscle cells (SMCs) and modulating nitric oxide production.
Under healthy conditions, vascular SMCs are maintained in
a quiescent and contractile state scattered within the inti-
mal extracellular matrix [55, 56]. In injured blood vessels or
in chronic vascular inflammation, SMCs switch to a more
synthetic phenotype and then activate, proliferate, and mi-
grate into the intima, resulting in thickening of the arterial
wall [55–57]. In an in vitro study, treatment with 40, 80, or
120 M AVA 2c significantly inhibited serum-induced SMC
proliferation by 41, 62, and 73%, respectively [55]. The mech-
anism underlying this effect involves G1 cell cycle arrest, with
AVA 2c acting on multiple steps upstream of pRb, inhibiting
cyclin D1 expression, and upregulating the cell cycle regula-
tory protein p21cip1 [56]. In addition, AVA 2c significantly
and dose-dependently increases nitric oxide production and
mRNA levels of endothelial nitric oxide synthase in both vas-
cular SMCs and HAECs [55].
It is generally believed that -glucan is responsible for the
cholesterol-lowering effect of oats. A recent human study in-
dicated that AVAs may also play a role in lowering plasma
cholesterol levels [38]. Daily supplementation with oat AVA
capsules (3.12 mg daily) for 1 month significantly decreased
total cholesterol by 11.1%, triglycerides by 28.1%, and low-
density lipoprotein cholesterol by 15.1% in 120 healthy sub-
jects (P<0.05).
2.3.4 Anticancer effects
Among the few in vitro studies that have evaluated the an-
ticancer effects of AVAs, Guo et al. reported that AVA 2c
dose-dependently inhibited proliferation of HT-29, HCT-116,
and LS-174 human colon cancer cell lines at concentrations
of 40–160 M [58]. To determine whether 2c metabolites re-
tain the biological effects of 2c, we compared the ability of
2c and its major metabolites (DH-2c, 2f, DH-2f, caffeic acid,
and 5-hydroxyanthranilic acid) to inhibit the growth of the
human colon cancer cell lines HCT-116 and HT-29 [36]. Com-
pared with 2c, the double bond reduced metabolite DH-2c was
more effective at inhibiting growth and triggering apoptosis
in human colon cancer cells, indicating that 2c continues to
be pharmacologically effective after being metabolized. Us-
ing cervical cancer HeLa cells stably transfected with a Wnt
signaling reporter, 2p was identified as a chemopreventive
compound. AVA 2p modulates upstream events in -catenin-
mediated transcription of the Wnt target gene c-Myc, inhibits
proliferation of HeLa cells, and increases -catenin degrada-
tion in the cytosol in a concentration-dependent manner [59].
Similarly, dihydroavenanthramide D (DH-1p), a synthetic
analogue of AVAs, inhibits human breast cancer cell invasion
by suppressing tetradecanoyl phorbol acetate induced matrix
C2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.mnf-journal.com
Mol. Nutr. Food Res. 61,7, 2017, 1600715 (7 of 12) 1600715
metallopeptidase 9 expression and blocking the MAPK/NF-
B and MAPK/AP-1 signaling pathways [60].
2.3.5 Anti-itch effects
Colloidal oatmeal is widely used as a topical treatment for skin
conditions such as atopic dermatitis and allergic or irritant
contact dermatitis. In a mouse model of chemically induced
pruritus, AVAs were shown to mediate the anti-itch effect
of oats, likely through their anti-inflammatory effects [61].
Compared with control mice, which scratched 79.2 times per
30 min on average, mice treated with AVAs (3 ppm) showed
a 40.7% decrease in scratching (47.0 scratches per 30 min
on average) [61]. Topical application of AVAs (2–3 ppm) sig-
nificantly decreased ear edema in the oxazolone model of
contact hypersensitivity [61]. The mean ear weights of AVA-
treated mice (6.24 mg, 2 ppm AVA; 3.58 mg, 3 ppm AVA)
were considerably lower than that of control mice (10.93 mg).
Topical application of AVAs also inhibited neurogenic inflam-
mation, as demonstrated by a 31.58% and 46.09% decrease
in resiniferatoxin-induced ear edema by 2 and 3 ppm AVA,
respectively [61]. In addition, the anti-inflammatory effects
of AVAs may suppress the secondary inflammation due to
scratching in atopic dermatitis and eczema. Furthermore,
the chemical structures of AVAs are similar to that of the
drug tranilast, which has antihistamine activity [62], suggest-
ing that the anti-itch properties of AVAs may be related to the
inhibition of histamine signaling. The synthetic analogue of
AVAs, DH-1p, also reduces histamine-related reactions such
as itching, redness, and wheals [63–65].
3 Avenacosides
3.1 Chemistry
Saponins play a role in plant defense and are widely dis-
tributed in the plant kingdom [66]. Although cereals are gen-
erally deficient in these secondary metabolites, oats contain
two types of saponins (avenacins and avenacosides), which
are synthesized by different biosynthetic pathways [67, 68].
Avenacins are triterpenoid saponins that are stored mainly in
roots, where they inhibit pathogens such as Gaeumannomyces
graminis [67, 68]. This family consists of four structurally re-
lated compounds: avenacins A-1, A-2, B-1, and B-2 (Fig. 4).
Avenacin A-1 is the most abundant of these saponins, com-
prising approximately 70% of the total avenacin content. Ave-
nacins A-1 and B-1 are esterified with N-methyl anthranilic
acid, whereas avenacins A-2 and B-2 are esterified with ben-
zoic acid (Fig. 4). The aglycone backbone of avenacins A-1 and
A-2 is the derivative of that of the B-1 and B-2 (hydroxylated
at C-4) (Fig. 4).
Avenacosides are nuatigenin-type steroid glycosides that
accumulate mainly in the leaves and grain [69, 70]. The
presence of avenacosides A and B, the two primary oat
avenacosides, in oat grains and leaves was first reported by
Tschesche et al. [71]. Their structures were established by
stepwise enzymatic degradation, hydrolysis of the perme-
thylated glycosides, and mass spectrometry as nuatigenin
3-O-{-L-rhamnopyranosyl-(14)-[β-D-glucopyranosyl-
(12)]-β-D-glucopyranoside}-26-O-β-D-glucopyranoside,
and nuatigenin 3-O-{-L-rhamnopyranosyl-(14)-[β-D-
glucopyranosyl-(13)-β-D-glucopyranosyl-(12)]-β-D-
glucopyranoside}-26-O-β-D-glucopyranoside, respectively. In
2011, Pecio and co-workers revised their structures, as shown
in Fig. 4, based on detailed 1-dimensional and 2-dimensional
nuclear magnetic resonance (NMR) analysis [71]. Avenaco-
sides A and B are glycosylated at C-3, with a trisaccharide (one
rhamnose and two glucose units) in the case of avenacoside
A, and a tetrasaccharide (one rhamnose and three glucose
units) in the case of avenacoside B; both are glycosylated at
C-26 with a glucose unit. The O-β-glucosidic bond at C-26
can be easily hydrolyzed by a special β-glucosidase (i.e.,
avenacosidase) to yield 26-deglucoavenacosides [72]. Besides,
avenacosides A [73] and B [74], 26-desglucoavenacosides A
(26-DGA) and B (26-DGB) [75, 76], avenacoside C [77], and
the sulfated avenacoside A [70] have also been detected in
oats (Fig. 4).
As part of our efforts to complete the chemical profile of oat
bran, five steroidal saponins were isolated by means of chro-
matographic methods, including silica gel and DiaionHP-20
chromatography [78]. Their structures were identified as ave-
nacosides A–D and chamaedroside E2(Fig. 4) by analyzing
their MS and NMR spectra. Among the five purified com-
pounds, avenacoside D is a new steroidal saponin with one
more glucose residue than avenacoside B at C-3 of the agly-
cone moiety. Chamaedroside E2was first identified as a com-
ponent of Veronica chamaedrys L., and we are the first to report
its presence in oats along with its full NMR assignment. Based
on the ionization and fragmentation patterns of the five pu-
rified compounds, we searched for minor steroidal saponins
in oat extract. Eleven compounds were detected, and their
structures were tentatively identified based on the analysis
of tandem mass spectra (MSn,n=2–3), as reported in our
recent article [78]. These saponins share the same aglycone
(nuatigenin) but vary according to sugar linkages or number
of sugar residues.
The avenacoside content in plants is influenced by species,
cultivar, plant part, physiological age, and geographic en-
vironment [67]. Few studies have compared saponin con-
tent across oat varieties. In an early study, Onning and co-
workers measured the levels of avenacosides A and B in
16 Scandinavian oat varieties using HPLC with UV detec-
tion at 200 nm [79]. The saponin content differed signifi-
cantly between cultivars, ranging from 200 to 500 mg/kg
with a mean of 400 mg/kg (dry matter basis). The avena-
coside A content was two to four times higher than the
avenacoside B content in these oat cultivars with mean val-
ues of 290 and 110 mg/kg, respectively. Because of the lack
of chromophores of oat saponins, the UV detection below
215 nm is not very specific or sensitive. Therefore, Pecio and
C2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.mnf-journal.com
1600715 (8 of 12) S. Sang and Y. F. Chu Mol. Nutr. Food Res. 61,7, 2017, 1600715
Figure 4. Structures of the major oat saponins.
co-workers developed a more sensitive ultraperformance
LC/MS method to quantify the levels of avenacosides A and
B and 26-desglucoavenacoside A (dAA) in 16 Polish oat culti-
vars [80]. The mean values of avenacosides A and B and dAA
were 360, 300, and 23.6 mg/kg in the grains, and 12, 10, and
3.1 mg/kg in the husks, respectively. The dAA concentration
was much lower than avenacoside A and B concentrations
in both grains and husks. Avenacoside A represented 41.9–
60.6% of the total saponin content in grains and 37.1–57.5%
in husks, whereas avenacoside B represented 35.8–55.2% of
the total saponin content in grains and 13.8–49.0% in husks.
Processing can also affect the saponin content in oat prod-
ucts. Onning and co-workers evaluated the effects of pH,
stainless steel, and iron on the stability of avenacosides A and
B during heat processing [81]. The avenacosides were stable at
room temperature for 24 h and when heated to 100Cfor3h
at pH 4–7. However, heating at 140C, especially at pH 4, led
to partial degradation. The rate of breakdown was the same
for avenacosides A and B, and the reduction was about 50%
after 3 h at pH 4. The decrease in the amount of avenacoside
A after heating at 140C for 3 h at pH 5, 6, and 7 was 19, 12,
and 13%, respectively. Iron and stainless steel dramatically
increased the rate of degradation at pH 4–6. Desrhamnoave-
nacosides A and B were identified as the major degradation
products of avenacosides A and B, respectively. We developed
an HPLC-MS method to analyze avenacosides in 15 different
commercial oat products including three oat bran products,
six oatmeal products, and six cold oat cereals [78]. In all 15
products, avenacoside A content was three to six times higher
than avenacoside B content. Saponin content differed signif-
icantly between the oat products, ranging from 37.9 to 377.5
mg/kg for avenacoside A and 11.7 to 89.2 mg/kg for avenaco-
side B. In general, concentrations of these compounds were
much lower in cold oat cereal than in oat bran or oatmeal.
3.2 Bioactivities with implication for health
Apart from their important role in plant defense, saponins
have received considerable attention for their potential as
cholesterol-lowering agents [82–85]. For example, Onning
and Asp used rodent models to investigate whether avena-
cosides contributed to the cholesterol-lowering effects of oats
[86]. Gerbils and rats fed high-cholesterol diets were treated
with avenacosides (0, 0.35, or 0.7 g/kg diet) for 21 and 19 days,
respectively. Compared with controls, the animals consum-
ing oat avenacosides showed significantly higher high-density
lipoprotein cholesterol levels and significantly lower liver
C2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.mnf-journal.com
Mol. Nutr. Food Res. 61,7, 2017, 1600715 (9 of 12) 1600715
cholesterol levels. No significant differences were observed
according to avenacoside dose (0.35 or 0.7 g/kg diet) regard-
ing total plasma cholesterol, high-density lipoprotein choles-
terol, and plasma triacylglycerol levels. However, plasma tri-
acylglycerols was significantly lower in rats given the higher
dose.
Onning and co-workers studied the effects of oat saponins
on nutrient absorption in the gut [87,88]. The treatment with
2 mg/mL avenacosides (1.7 mg avenacoside A and 0.3 mg
avenacoside B) inhibited maltase, trehalase, and lactase ac-
tivity in vitro and significantly increased starch hydrolysis by
-amylase. However, 1 mg/mL avenacosides (0.696 g avena-
coside A and 0.135 g avenacoside B per gram dry matter)
had no effect on the active transport of glucose. Avenaco-
side treatment significantly increased passive transport of the
macromolecule ovalbumin in both the proximal and the dis-
tal small intestine and appeared to increase permeability of
small marker molecules (mannitol and [51Cr]EDTA). These
in vitro effects were not observed after treatment with a crude
oat extract in either study.
The O-β-glucosidic bond at C-26 can be easily hydrolyzed
by a special β-glucosidase (avenacosidase) to yield bioac-
tive 26-deglucoavenacosides [72]. 26-Desglucoavenacosides A
and B have been shown to inhibit the phytopathogenic fun-
gus Stagonospora avenae [89], and 26-desglucoavenacoside B
strongly inhibits the fungus Pyrenophora mycelia [8]. In addi-
tion, 26-desglucoavenacosides A and B show hemolytic and
antibiotic activity [90]. The sugar moieties at C-3 are essen-
tial for the antimicrobial effects of 26-deglucoavenacosides
[89], and these saponins can be detoxified via sequential hy-
drolysis of the sugar units at C-3 by -rhamnosidase and
β-glucosidase, which are secreted by pathogenic fungi [89].
The immunoregulatory and anticancer activities of avena-
cosides have also been reported. In an in vitro model, 3 and
10 g/mL avenacoside A decreased intracellular IL-2 produc-
tion in activated T lymphocytes by 23 and 32%, respectively
[91]. In our recent study [78], we demonstrated that avena-
cosides A and B inhibit growth in human colon cancer cells.
Both avenacosides showed weak activity in the cell lines tested
(HCT-116 and HT-29); however, avenacoside B was more po-
tent than A in both cell lines with an IC50 of 175.3 Min
HCT-116 cells.
4 Conclusions and perspectives
The nutritional benefits of oats appear to go beyond fiber
to bioactive compounds with strong antioxidant and anti-
inflammatory effects, suggesting that consuming oats may
help prevent chronic diseases such as cancer and cardiovas-
cular disease. However, studies on the beneficial effects of
AVAs are still in their infancy, and additional health benefits
of AVAs may yet be identified. Similarly, few studies have
assessed the bioactivity of avenacosides A and B, indicating
the need for more research in this area.
Increased consumption of whole grain oats has been in-
versely associated with the risk for developing diet-related dis-
orders including type 2 diabetes, cancer, and cardiovascular
diseases [5, 92–94]. However, the results of epidemiological
studies have not been consistent because of the lack of tools
able to accurately assess dietary intake and internal dosage.
For example, food frequency questionnaires and 24-h food
recalls, the two methods used most often in epidemiological
studies to assess dietary intake, cannot accurately measure
the amounts of specific foods consumed. Besides food intake,
other factors must be considered including the levels of the
bioactive components, which are influenced by factors such as
plant cultivar, processing methods, and storage. Interindivid-
ual genetic differences also hamper the ability to determine
the relationship between the intake of specific foods and the
risk of chronic diseases. For example, the same compound
can be metabolized and absorbed differently in individuals
with different genetic backgrounds. Interindividual variation
of the gut microbiota adds another layer of complexity.
To better understand the beneficial health effects of whole
grains, biomarkers for their exposure and effects are needed.
The AVAs and avenacosides A and B are unique components
of oats. Therefore, these compounds and their metabolites
may be useful as markers of whole grain oat intake and in-
terindividual genetic differences.
PepsiCo, Inc. provided funding for the work. Y.C. is an em-
ployee of PepsiCo, Inc., which manufactures oatmeal products
under the brand name Quaker Oats R. The views expressed in
this article are those of the authors and do not necessarily reflect
the opinion or policies of PepsiCo, Inc.
The authors have declared no conflict of interest.
5 References
[1] Cho, S. S., Qi, L., Fahey, G. C., Jr., Klurfeld, D. M., Con-
sumption of cereal fiber, mixtures of whole grains and bran,
and whole grains and risk reduction in type 2 diabetes, obe-
sity, and cardiovascular disease. Am. J. Clin. Nutr. 2013, 98,
594–619.
[2] Aune, D., Chan, D. S., Lau, R., Vieira, R. et al., Dietary fibre,
whole grains, and risk of colorectal cancer: systematic re-
view and dose-response meta-analysis of prospective stud-
ies. BMJ 2011, 343, d6617.
[3] Singh, R., De, S., Belkheir, A., Avena sativa (oat), a potential
neutraceutical and therapeutic agent: an overview. Crit. Rev.
Food Sci. 2013, 53, 126–144.
[4] Bao, L., Cai, X., Xu, M., Li, Y., Effect of oat intake on gly-
caemic control and insulin sensitivity: a meta-analysis of
randomised controlled trials. Br. J. Nutr. 2014, 112, 457–
466.
[5] Boffetta, P., Thies, F., Kris-Etherton, P., Epidemiological stud-
ies of oats consumption and risk of cancer and overall mor-
tality. Br. J. Nutr. 2014, 112 (Suppl 2), S14–S18.
C2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.mnf-journal.com
1600715 (10 of 12) S. Sang and Y. F. Chu Mol. Nutr. Food Res. 61,7, 2017, 1600715
[6] Thies, F., Masson, L. F., Boffetta, P., Kris-Etherton, P., Oats and
bowel disease: a systematic literature review. Br.J.Nutr.
2014, 112 (Suppl 2), S31–S43.
[7] Singh, R., De, S., Belkheir, A., Avena sativa (oat), a potential
neutraceutical and therapeutic agent: an overview. Crit. Rev.
Food Sci. Nutr. 2013, 53, 126–144.
[8] Bahraminejad, S., Asenstorfer, R. E., Riley, I. T., Schultz, C.
J., Analysis of the antimicrobial activity of flavonoids and
saponins isolated from the shoots of oats (Avena sativa L.).
J. Phytopathol. 2008, 156,17.
[9] Dimberg, L. H., Gissen, C., Nilsson, J., Phenolic compounds
in oat grains (Avena sativa L.) grown in conventional and
organic systems. Ambio 2005, 34, 331–337.
[10] Dokuyucu, T., Peterson, D. M., Akkaya, A., Contents of an-
tioxidant compounds in turkish oats: simple phenolics and
avenanthramide concentrations. Cereal Chem. J. 2003, 80,
542–543.
[11] Bahraminejad, S., Asenstorfer, R. E., Riley, I. T., Schultz, C.
J., Analysis of the antimicrobial activity of flavonoids and
saponins isolated from the shoots of oats (Avena sativa L.).
J. Phytopathol. 2007, 156,17.
[12] Niemann, G. J., The anthranilamide phytoalexins of the
caryophyllaceae and related compounds. Phytochemistry
1993, 34, 319–328.
[13] Bryngelsson, S., Ishihara, A., Dimberg, L. H., Levels of
avenanthramides and activity of hydroxycinnamoyl-CoA:
hydroxyanthranilate N-hydroxycinnamoyl transferase (HHT)
in steeped or germinated oat samples. Cereal Chem. 2003,
80, 356–360.
[14] Collins, F. W., Oat phenolics—avenanthramides, substituted
N-cinnamoyl-anthranilate alkaloids from oat bran and oat
hulls. Cereal Food World 1986, 31, 593–593.
[15] Collins, F. W., Oat phenolics—avenanthramides, novel sub-
stituted N-cinnamoylanthranilate alkaloids from oat groats
and hulls. J. Agr. Food Chem. 1989, 37, 60–66.
[16] Wise,M.L.,in:Chu,Y.(Ed.),Oats Nutrition and Technology,
John Wiley & Sons, 2014, pp. 195–222.
[17] Jastrebova, J., Skoglund, M., Nilsson, J., Dimberg, L. H.,
Selective and sensitive LC-MS determination of avenan-
thramides in oats. Chromatographia 2006, 63, 419–
423.
[18] Bratt, K., Sunnerheim, K., Bryngelsson, S., Fagerlund, A.
et al., Avenanthramides in oats (Avena sativa L.) and
structure-antioxidant activity relationships. J. Agr. Food
Chem. 2003, 51, 594–600.
[19] Bryngelsson, S., Mannerstedt-Fogelfors, B., Kamal-Eldin, A.,
Andersson, R., Dimberg, L. H., Lipids and antioxidants in
groats and hulls of Swedish oats (Avena sativa L). J. Sci.
Food Agr. 2002, 82, 606–614.
[20] Dimberg, L. H., Theander, O., Lingnert, H.,
Avenanthramides—a group of phenolic antioxidants in
oats. Cereal Chem. 1993, 70, 637–641.
[21] Emmons, C. L., Peterson, D. M., Antioxidant activity and phe-
nolic contents of oat groats and hulls. Cereal Chem. 1999, 76,
902–906.
[22] Collins, F.W., McLachlan, D.C., Blackwell, B. A., Oat phenolics:
avenalumic acids, a new group of bound phenolic acids from
oat groats and hulls. Cereal Chem. 1991, 68, 184–189.
[23] Emmons, C. L., Peterson, D. M., Antioxidant activity and phe-
nolic content of oat as affected by cultivar and location. Crop
Sci. 2001, 41, 1676–1681.
[24] Dimberg, L. H., Molteberg, E. L., Solheim, R., Frolich, W., Vari-
ation in oat groats due to variety, storage and heat treatment.
1. Phenolic compounds. J. Cereal. Sci. 1996, 24, 263–272.
[25] Skoglund, M., Peterson, D. M., Andersson, R., Nilsson, J.,
Dimberg, L. H., Avenanthramide content and related enzyme
activities in oats as affected by steeping and germination. J.
Cereal Sci. 2008, 48, 294–303.
[26] Shewry, P. R., Piironen, V., Lampi, A. M., Nystrom, L. et al.,
Phytochemical and fiber components in oat varieties in the
HEALTHGRAIN diversity screen. J. Agr. Food Chem. 2008,
56, 9777–9784.
[27] Ishihara, A., Matsukawa, T., Miyagawa, H., Ueno, T. et al., In-
duction of hydroxycinnamoyl-CoA: hydroxyanthranilate N-
hydroxycinnamoyltransferase (HHT) activity in oat leaves by
victorin C. Z. Naturforsch. C. 1997, 52, 756–760.
[28] Ishihara, A., Miyagawa, H., Matsukawa, T., Ueno, T. et al.,
Induction of hydroxyanthranilate hydroxycinnamoyl trans-
ferase activity by oligo-N-acetylchitooligosaccharides in
oats. Phytochemistry 1998, 47, 969–974.
[29] Peterson, D. M., Dimberg, L. H., Avenanthramide concen-
trations and hydroxycinnamoyl-CoA : hydroxyanthranilate
N-hydroxycinnamoyltransferase activities in developing
oats. J. Cereal Sci. 2008, 47, 101–108.
[30] Dimberg, L. H., Sunnerheim, K., Sundberg, B., Walsh, K.,
Stability of oat avenanthramides. Cereal Chem. 2001, 78,
278–281.
[31] Collins, F. W., Mullin, W. J., High-Performance liquid-
chromatographic determination of avenanthramides,
N-aroylanthranilic acid alkaloids from oats. J. Chromatogr.
A1988, 445, 363–370.
[32] Bryngelsson, S., Dimberg, L. H., Kamal-Eldin, A., Effects of
commercial processing on levels of antioxidants in oats
(Avena sativa L.). J. Agric. Food Chem. 2002, 50, 1890–1896.
[33] Chen, C. Y., Milbury, P. E., Kwak, H. K., Collins, F. W. et al.,
Avenanthramides and phenolic acids from oats are bioavail-
able and act synergistically with vitamin C to enhance ham-
ster and human LDL resistance to oxidation. J. Nutr. 2004,
134, 1459–1466.
[34] Chen, C. Y. O., Milbury, P. E., Collins, F. W., Blumberg, J.
B., Avenanthramides are bioavailable and have antioxidant
activity in humans after acute consumption of an enriched
mixture from oats. J. Nutr. 2007, 137, 1375–1382.
[35] Koenig, R. T., Dickman, J. R., Wise, M. L., Ji, L. L., Avenan-
thramides are bioavailable and accumulate in hepatic, car-
diac, and skeletal muscle tissue following oral gavage in rats.
J. Agr. Food Chem. 2011, 59, 6438–6443.
[36] Wang, P., Chen, H., Zhu, Y., McBride, J. et al., Oat
avenanthramide-C (2c) is biotransformed by mice and the
human microbiota into bioactive metabolites. J. Nutr. 2015,
145, 239–245.
C2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.mnf-journal.com
Mol. Nutr. Food Res. 61,7, 2017, 1600715 (11 of 12) 1600715
[37] van Duynhoven, J., Vaughan, E. E., Jacobs, D. M., Kemper-
man, R. A. et al., Metabolic fate of polyphenols in the human
superorganism. Proc. Natl. Acad. Sci. USA 2011, 108 (Suppl
1), 4531–4538.
[38] Liu, S., Yang, N., Hou, Z. H., Yao, Y. et al., Antioxidant effects
of oats avenanthramides on human serum. Agric. Sci. China
2011, 10, 1301–1305.
[39] Koenig, R., Dickman, J. R., Kang, C. H., Zhang, T.
O. et al., Avenanthramide supplementation attenuates
exercise-induced inflammation in postmenopausal women.
Nutr. J. 2014, 13, 21.
[40] Ji, L. L., Lay, D., Chung, E., Fu, Y., Peterson, D. M., Effects
of avenanthramides on oxidant generation and antioxidant
enzyme activity in exercised rats. Nutr. Res. 2003, 23, 1579–
1590.
[41] Meydani, M., Potential health benefits of avenanthramides
of oats. Nutr. Rev. 2009, 67, 731–735.
[42] Ren, Y., Yang, X. S., Niu, X. W., Liu, S., Ren, G. X., Chemi-
cal characterization of the avenanthramide-rich extract from
oat and its effect on D-galactose-induced oxidative stress in
mice. J. Agr. Food Chem. 2011, 59, 206–211.
[43] Yang, J., Ou, B. X., Wise, M. L., Chu, Y. F., In vitro total antiox-
idant capacity and anti-inflammatory activity of three com-
mon oat-derived avenanthramides. Food Chem. 2014, 160,
338–345.
[44] Peterson, D. M., Hahn, M. J., Emmons, C. L., Oat avenan-
thramides exhibit antioxidant activities in vitro. Food Chem.
2002, 79, 473–478.
[45] Lee-Manion, A. M., Price, R. K., Strain, J. J., Dimberg, L. H.
et al., In vitro antioxidant activity and antigenotoxic effects
of avenanthramides and related compounds. J. Agr. Food
Chem. 2009, 57, 10619–10624.
[46] Fagerlund, A., Sunnerheim, K., Dimberg, L. H., Radical-
scavenging and antioxidant activity of avenanthramides.
Food Chem. 2009, 113, 550–556.
[47] Fu, J., Zhu, Y., Yerke, A., Wise, M. L. et al., Oat avenan-
thramides induce heme oxygenase-1 expression via Nrf2-
mediated signaling in HK-2 cells. Mol. Nutr. Food Res. 2015,
59, 2471–2479.
[48] Ma, Q., Role of nrf2 in oxidative stress and toxicity. Annu.
Rev. Pharmacol. Toxicol. 2013, 53, 401–426.
[49] Kensler, T. W., Wakabayashi, N., Biswal, S., Cell survival
responses to environmental stresses via the Keap1-Nrf2-
ARE pathway. Annu. Rev. Pharmacol. Toxicol. 2007, 47,
89–116.
[50] Sussan, T. E., Rangasamy, T., Blake, D. J., Malhotra, D. et al.,
Targeting Nrf2 with the triterpenoid CDDO-imidazolide at-
tenuates cigarette smoke-induced emphysema and cardiac
dysfunction in mice. Proc. Natl. Acad. Sci. USA 2009, 106,
250–255.
[51] Zhang, D. D., Mechanisticstudies of the Nrf2-Keap1 signaling
pathway. Drug Metab. Rev. 2006, 38, 769–789.
[52] Koenig, R. T., Dickman, J. R., Kang, C. H., Zhang, T.
et al., Avenanthramide supplementation attenuates ec-
centric exercise-inflicted blood inflammatory markers in
women. Eur. J. Appl. Physiol. 2016, 116, 67–76.
[53] Liu, L. P., Zubik, L., Collins, F. W., Marko, M., Meydani, M.,
The antiatherogenic potential of oat phenolic compounds.
Atherosclerosis 2004, 175, 39–49.
[54] Guo, W., Wise, M. L., Collins, F. W., Meydani, M., Avenan-
thramides, polyphenols from oats, inhibit IL-1 beta-induced
NF-kappa B activation in endothelial cells. Free Radic. Biol.
Med. 2008, 44, 415–429.
[55] Nie, L., Wise, M. L., Peterson, D. M., Meydani, M., Avenan-
thramide, a polyphenol from oats, inhibits vascular smooth
muscle cell proliferation and enhances nitric oxide produc-
tion. Atherosclerosis 2006, 186, 260–266.
[56] Nie, L., Wise, M., Peterson, D., Meydani, M., Mechanism by
which avenanthramide-c, a polyphenol of oats, blocks cell cy-
cle progression in vascular smooth muscle cells. Free Radic.
Biol. Med. 2006, 41, 702–708.
[57] Ross, R., Atherosclerosis–an inflammatory disease. N. Engl.
J. Med. 1999, 340, 115–126.
[58] Guo, W. M., Nie, L., Wu, D. Y., Wise, M. L. et al., Avenan-
thramides inhibit proliferation of human colon cancer cell
lines in vitro. Nutr. Cancer 2010, 62, 1007–1016.
[59] Wang, D., Wise, M. L., Li, F., Dey, M., Phytochemicals attenu-
ating aberrant activation of beta-catenin in cancer cells. Plos
One 2012, 7, e50508.
[60] Lee, Y. R., Noh, E. M., Oh, H. J., Hur, H. et al., Dihy-
droavenanthramide D inhibits human breast cancer cell in-
vasion through suppression of MMP-9 expression. Biochem.
Biophys. Res. Commun. 2011, 405, 552–557.
[61] Sur, R., Nigam, A., Grote, D., Liebel, F., Southall, M.
D., Avenanthramides, polyphenols from oats, exhibit anti-
inflammatory and anti-itch activity. Arch. Dermatol. Res.
2008, 300, 569–574.
[62] Darakhshan, S., Pour, A. B., Tranilast: a review of its thera-
peutic applications. Pharmacol. Res. 2015, 91, 15–28.
[63] Heuschkel, S., Wohlrab, J., Schmaus,G., Neubert, R. H., Mod-
ulation of dihydroavenanthramide D release and skin pen-
etration by 1,2-alkanediols. Eur. J. Pharm. Biopharm. 2008,
70, 239–247.
[64] Vollhardt, J. D. A. F., Redmond, M., 21st IFSCC International
Congress, Berlin 2000, p. 395.
[65] Schmaus, G. M. H., Joppe, H., Lange, S., Koch, O., Pillai, r.,
Roding, J., 24th IFSCC International Congress, Osaka 2006,
p. 36.
[66] Morant, A. V., Jørgensen, K., Jørgensen, C., Paquette, S. M.
et al., -Glucosidases as detonators of plant chemical de-
fense. Phytochemistry 2008, 69, 1795–1813.
[67] Papadopoulou, K., Melton, R. E., Leggett, M., Daniels, M. J.,
Osbourn, A. E., Compromised disease resistance in saponin-
deficient plants. Proc. Nat. Acad. Sci. USA 1999, 96, 12923–
12928.
[68] Osbourn, A. E., Saponins in cereals. Phytochemistry 2003,
62,14.
[69] Nisius, A., The stromacentre in Avena plastids: an aggrega-
tion of -glucosidase responsible for the activation of oat-
leaf saponins. Planta 1988, 173, 474–481.
[70] Pecio, Ł., J˛
edrejek, D., Masullo, M., Piacente, S. et al., Re-
vised structures of avenacosides A and B and a new sulfated
C2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.mnf-journal.com
1600715 (12 of 12) S. Sang and Y. F. Chu Mol. Nutr. Food Res. 61,7, 2017, 1600715
saponin from Avena sativa L. Magn. Reson. Chem. 2012, 50,
755–758.
[71] Pecio, L., Jedrejek, D., Masullo, M., Piacente, S. et al., Re-
vised structures of avenacosides A and B and a new sulfated
saponin from Avena sativa L. Magn. Reson. Chem. 2012, 50,
755–758.
[72] Kesselmeier, J., Steroidal saponins in etiolated, greening
and green leaves and in isolated etioplasts and chloroplasts
of Avena sativa.Protoplasma 1982, 112, 127–132.
[73] Tschesche, R., Tauscher, M., Fehlhaber, H.-W., Wulff, G.,
Steroidsaponine mit mehr als einer Zuckerkette, IV. Avena-
cosid A, ein bisdesmosidisches Steroidsaponin aus Avena
sativa.Chem. Ber. 1969, 102, 2072–2082.
[74] Tschesche, R., Lauven, P., Steroidsaponine mit mehr als einer
Zuckerkette, V. Avenacosid B, ein zweites bisdesmosidis-
ches Steroidsaponin aus Avena sativa.Chem. Ber. 1971, 104,
3549–3555.
[75] Tschesche, R., Wiemann, W., Steroidsaponine mit mehr als
einer Zuckerkette, XI. Desgluco-avenacosid-A und -B, biol-
ogisch aktive Nuatigeninglycoside. Chem. Ber. 1977, 110,
2416–2423.
[76] Bahraminejad, S., Asenstorfer, R. E., Riley, I. T., Schultz, C.
J., Analysis of the antimicrobial activity of flavonoids and
saponins isolated from the shoots of oats (Avena sativa L.).
J. Phytopathol. 2008, 156,17.
[77] Lu Can, X. D., Nuati saponins from oats. Nat. Prod. Res. Dev.
2013, 25, 68–70.
[78] Yang, J., Wang, P., Wu, W., Zhao, Y. et al., Steroidal saponins
in oat bran. J. Agric. Food Chem. 2016, 64, 1549–1556.
[79] Onning, G., Nils-Georg, A., Sivik, B., Saponin content in dif-
ferent oat varieties and in different fractions of oat grain.
Food Chem. 1993, 48, 251–254.
[80] Pecio, L., Wawrzyniak-Szolkowska, A., Oleszek, W.,
Stochmal, A., Rapid analysis of avenacosides in grain
and husks of oats by UPLC-TQ-MS. Food Chem. 2013, 141,
2300–2304.
[81] Onning, G. J., Marcel, A., Fay, L., Asp, N.-G., Degradation of
oat saponins during heat processing-effect of pH, stainless
steel, and iron at different temperatures. J. Agr. Food Chem.
1994, 42, 2578–2582.
[82] Yamamoto, M., Kumagai, A., Yamamura, Y., Plasma lipid-
lowering action of ginseng saponins and mechanism of the
action. Am. J. Chin. Med. 1983, 11, 84–87.
[83] Vinarova, L., Vinarov, Z., Atanasov, V., Pantcheva, I. et al.,
Lowering of cholesterol bioaccessibility and serum concen-
trations by saponins: in vitro and in vivo studies. Food Funct.
2015, 6, 501–512.
[84] Molteberg, E. L., Solheim, R., Dimberg, L. H., Frolich, W.,
Variation in oat groats due to variety, storage and heat
treatment. 2. Sensory quality. J. Cereal. Sci. 1996, 24, 273–
282.
[85] Morehouse, L. A., Bangerter, F.-W., DeNinno, M. P., Inskeep,
P. B. et al., Comparison of synthetic saponin cholesterol ab-
sorption inhibitors in rabbits evidence for a nonstoichiomet-
ric, intestinal mechanism of action. J. Lipid Res. 1999, 40,
464–474.
[86] Onning, G., Asp, N. G., Effect of oat saponins on plasma and
liver lipids in gerbils (Meriones unguiculatus)andrats.Br. J.
Nutr. 1995, 73, 275–286.
[87] Onning, G., Asp, N. G., Effect of oat saponins and different
types of dietary fibre on the digestion of carbohydrates. Br.
J. Nutr. 1995, 74, 229–237.
[88] Onning, G., Wang, Q., Westrom, B. R., Asp, N. G., Karlsson,
B. W., Influnce of oat saponins on intestinal permeability in
vitro and in vivo in the rat. Br. J. Nutr. 1996, 76, 141–151.
[89] Morrissey, J. P., Wubben, J. P., Osbourn, A. E., Stagonospora
avenae secretes multiple enzymes that hydrolyze oat leaf
saponins. Mol. Plant Microbe Interact. 2000, 13, 1041–
1052.
[90] Tschesche, R. W. W., Desgluco-avenacosid-A and -B, biolog-
ically active nuatigenin glycosides. Chem. Ber. 1977, 110,
2416–2423.
[91] Mandeau, A., Aries, M. F., Boe, J. F., Brenk, M. et al.,
Rhealba(R) oat plantlet extract: evidence of protein-free con-
tent and assessment of regulatory activity on immune in-
flammatory mediators. Planta Med. 2011, 77, 900–906.
[92] Wang, Q., Ellis, P. R., Oat beta-glucan: physico-chemical char-
acteristics in relation to its blood-glucose and cholesterol-
lowering properties. Br.J.Nutr.2014, 112 (Suppl 2), S4–
S13.
[93] Thies, F., Masson, L. F., Boffetta, P., Kris-Etherton, P., Oats and
CVD risk markers: a systematic literature review. Br. J. Nutr.
2014, 112 (Suppl 2), S19–S30.
[94] Rose, D. J., Impact of whole grains on the gut microbiota:
the next frontier for oats? Br. J. Nutr. 2014, 112 (Suppl 2),
S44–S49.
C2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.mnf-journal.com
... Among cereal crops, oat (Avena sativa L.) seems exceptional in that it contains a number of elements that are important for human diet, livestock feed, wellness care, and cosmetics (Butt et al., 2008;Varma et al., 2016). It is an annually crop which has been raised for more than 2000 years in several parts of the world (Sang and Chu, 2017) and is considered the ancient types of plants cultivated in human civilization (Lasztity, 1998). Thousands of years later, other grains like wheat and barley first begun cultivated (Murphy and Hoffman, 1992). ...
... The use of oats as an early grain in breakfast cereals, beverages, bread, even newborn feeds is creating novel food products thanks to the appeal of ancient grains and their higher nutritive value (Boukid, 2017). Oats are mostly used in breakfast cereals including snack bars, however, their health-promoting qualities make them an excellent addition to other products, which would substantially benefit consumers (Sang and Chu, 2017;Sang et al., 2017). The viscous polysaccharide known as oat beta-glucan (OBG), which is made up of a linear branched chain of D-glucose monosaccharaides joined by mixed (1 3) and (1 4) linkages, is one of the main components of soluble fiber (Sang and Chu, 2017). ...
... The use of oats as an early grain in breakfast cereals, beverages, bread, even newborn feeds is creating novel food products thanks to the appeal of ancient grains and their higher nutritive value (Boukid, 2017). Oats are mostly used in breakfast cereals including snack bars, however, their health-promoting qualities make them an excellent addition to other products, which would substantially benefit consumers (Sang and Chu, 2017;Sang et al., 2017). The viscous polysaccharide known as oat beta-glucan (OBG), which is made up of a linear branched chain of D-glucose monosaccharaides joined by mixed (1 3) and (1 4) linkages, is one of the main components of soluble fiber (Sang and Chu, 2017). ...
... In addition to increase in the micronutrient content, efforts to eliminate the anti-nutrients and increase the molecules that aid in nutrient absorption are also critical for bioavailability (Bouis and Welch, 2010). The importance of anti-nutrients can be determined from the fact that new research programs aimed at prophylactic or medicinal uses of these components are focusing on determining types of bioactivity (Martínez-Villaluenga and Peñ as, 2017;Sang and Chu, 2017;Tikhonova et al., 2020). ...
Chapter
Wheat, as a key component of cereal-based diets and a major staple food in most nations, must be emphasized if all forms of hunger are to be eradicated by 2030. Wheat biofortification is a promising, realistic, and cost-effective method that is becoming increasingly essential in the fight against hidden hunger, which affects nearly one-third of the world's population. Biofortification approaches such as agronomic practices, genetic, and genomic interventions could improve nutrient bioavailability and reduce anti-nutrient chemicals in the edible section of the crop. Recent advances in molecular breeding, genetic engineering, gene stacking, and metabolic engineering technologies have opened up new avenues for advancement. In addition to scientific knowledge, consumer and farmer awareness, as well as legislative initiatives, are required.
... Oats lipids are mainly composed of monoand polyunsaturated fatty acids. Besides this, oats are also dense in antioxidants and polyphenols viz., avenanthramides (2e289 mg/kg), saponins (avenacoside A-290 mg/kg, and avenacoside B-110 mg/kg) (Sang & Chu, 2017). Also, oats bglucans have known anticancerous potential by reducing the causative agents of colon cancer along with significant reduction in blood cholesterol level blood pressure. ...
Chapter
Plant-based beverages are gaining popularity among consumers who are seeking alternative and environmentally sustainable options to traditional dairy drinks. The food industry is therefore developing a range of affordable, convenient, desirable, nutritional, and sustainable plant-based milk alternatives. This chapter provides an overview of the current knowledge on fundamental processing steps to convert plant material into plant-based beverages, what are processing challenges for different plant sources, how to overcome these challenges and potential quality deficiencies, and what are the opportunities to maximize textural, nutritional, and sensory aspects of plant-based beverages.
... Examples of whole grains would include major cereals, such as wheat (durum, kamut, farro einkorn, emmer, spelt), barley (hulled, dehulled), rice (brown, black, red, etc.), rye, oats, and corn/maize; minor cereals, such as millets, job's tears, canary grass, fonio, sorghum, wild rice, triticale, and teff, as well as pseudocereals (Priebe and McMonagle, 2016;Shahidi, 2009;Zeng et al., 2018). For instance, oats contain good amounts of phenolic acids, phytosterols, vitamin E, carotenoids, soluble dietary fiber (especially β-glucan), flavonoids, etc. (Sang and Chu, 2017). Maize (corn) also contain important phytochemicals, for instance, in corn silk and corn seeds (Nawaz et al., 2018;Bujang et al., 2021;Miranda et al., 2021). ...
Article
Full-text available
Nutraceuticals play wide range of important roles, from health promotion, increasing life expectancy, maintaining body cell integrity, to reducing the risks of many diseases. As consumers continue to be attracted to nutraceuticals, such as superfoods, vegetables, fruits, high-protein foods, eating healthy intertwines with finding the right balance. Nowadays, the nutraceutical industries are among the many that target to meet the dynamically growing consumers’ expectations. Moreover, foods and agricultural commodities contain bioactive constituents, which are mostly responsible for their nutraceutical functions. How nutraceuticals, especially functional foods, etc., help in tackling health challenges increase the interest among several researchers in this subject area, and given the ever-growing need across communities around the globe for healthy living, strengthens the need for continued synthesis of published information to supplement existing knowledge. This overview, therefore, discusses natural nutraceuticals, especially functional foods, their major bioactive components, formulation, health benefits for disease prevention.
Article
Background Current clinical trials have shown controversial results regarding the effects of oat consumption on blood pressure (BP) in adults. Objective The meta-analysis was conducted to systematically evaluate the effects of oat consumption on BP in adults. Methods Electronic databases including PubMed, Web of Science, Scopus, the Cochrane Library, and Embase were searched until December 13, 2021 for eligible randomized controlled trials (RCTs). RCTs that published in English and explored the effects of oat consumption on BP in adults under matched total energy intake were included. Meta-analysis using a random-effects model was performed. The pooled effect size was expressed as mean difference (MD) and 95% confidence interval (CI). I² statistics were used to quantify heterogeneity. The risk of bias was assessed using the Cochrane Risk-of-Bias tool (RoB 2.0). Results 21 RCTs involving 1569 participants were included. The pooled results indicated that consuming oats significantly reduced systolic blood pressure (SBP) [MD = -2.82 mmHg; (95% CI -4.72, -0.93); P = 0.004]. Subgroup analyses indicated that oat consumption significantly reduced SBP in hypertensive participants, or when compared to control group participants who consumed refined grains. No significant reduction in diastolic blood pressure (DBP) after oat consumption was observed [MD = -1.16 mmHg; (95% CI -2.37, 0.04); P = 0.060]. However, the sensitivity analysis of DBP, removal of individual studies or "leave one out meta-analysis", showed a significant reduction in DBP, suggesting the pooled result in the main analysis was not robust. Subgroup analyses showed that oat consumption did significantly reduce DBP in participants with baseline BP in the prehypertensive range. Both SBP and DBP were significantly reduced when the dose of oat consumption was ≥ 5 g/d b-glucan, or the oat consumption duration was ≥ 8 weeks. Conclusions Oat consumption is effective in reducing SBP levels, particularly in individuals whose baseline BP are in the hypertensive range, or when compared to control group participants consuming refined grains at matched total energy intake.
Article
Oat is classified as a whole grain and contains high contents of protein, lipids, carbohydrates, vitamins, minerals, and phytochemicals (such as polyphenols, flavonoids, and saponins). In recent years, studies have focused on the effects of oat consumption on reducing the risk of a variety of diseases. Reports have indicated that an oat diet exerts certain biological functions, such as preventing cardiovascular diseases, reducing blood glucose, and promoting intestinal health, along with antiallergy, antioxidation, and cancer preventive effects. At present, cancer is the second leading cause of death worldwide. The natural products of oat are an important breakthrough for developing new strategies of cancer prevention, and their ability to interact with multiple cellular targets helps to combat the complexity of cancer pathogenesis. In addition, the comprehensive study of the cancer prevention activity and potential mechanism of oat nutrients and phytochemicals has become a research hotspot. In this Review, we focused on the potential functions of peptides, dietary fiber, and phytochemicals in oats on cancer prevention and further revealed novel mechanisms and prospects for clinical application. These findings might provide a novel approach to deeply understand the functions and mechanisms for cancer prevention of oat consumption.
Chapter
Beverage industry has significantly evolved in formulating diverse products to meet the requirements of nutraceutical or functional food category. In this context, plant-based extracts from diverse sources such as soybean, almond, coconut, oat, pulses, and rice called plant-based milk alternatives (PBMAs) or analogs form an integral component of beverage industry. The growth in the PBMA industry could be attributed to various reasons, namely, dietary preferences, and nutritional needs. Additionally, the plant-based milk products are rich sources of health-promoting bioactives and are devoid of cholesterol and ecologically require less energy input per unit of milk production and thus are much appreciated. Nevertheless, there are technological bottlenecks in developing a wholesome substitute for cow’s milk owing to different physicochemical properties of PBMAs. This chapter discusses various sources of PBMAs, their nutritional composition, blending of PBMAs for nutritional complementation effect and to improve the sensory profile of the product and the need for post-harvest technological intervention, alternate strategies, and challenges ahead in the production process of PBMAs.
Article
To our knowledge, the study interconnection between inherent chemical functional group spectral features and nutrient utilisation is still limited. The objective of this study was to test the adequacy of vibrational Fourier transform infrared attenuated total reflectance (ATR-FTIR) spectroscopy as a fast tool to assess the interactive relationship between the nutritive value of the Prairie cool-season oat (Avena sativa L.) varieties in dairy cows and inherent chemical functional group spectral features. The chemical functional group spectral features of the Prairie cool-season oat varieties in western Canada were determined by Fourier transform infrared attenuated total reflectance spectroscopy. The protein-related spectral parameters of chemical functional groups included peak height and peak area intensity of Amide I, Amid II, protein structural α-helix and β-sheet, and their ratios. The rumen degradation kinetics were determined using in situ techniques with four rumen-canulated lactating dairy cows. The intestinal digestion was evaluated using a three-step in vitro technique with 12 h preincubation. The experiment was an randomized complete block design. The data were analysed using the mixed-model procedure of the Statistical Analysis System. The results showed that the interconnection between rumen degradation kinetics, intestinal digestion and true nutrient supply to dairy cows and protein-related chemical functional group spectral features could be revealed by ATR-FTIR with univariate and multi-variate spectral analyses. These findings indicate that ruminant relevant nutritive value of cool-season oats could be rapidly evaluated and predicted using oat-specific functional group spectral characteristics which could be obtained by a non-distractive bioanalytical tool of ATR-FTIR spectroscopy.
Article
Full-text available
Coarse cereals are rich in dietary fiber, B vitamins, minerals, secondary metabolites, and other bioactive components, which exert numerous health benefits. To better understand the diversity of metabolites in different coarse cereals, we performed widely targeted metabolic profiling analyses of six popular coarse cereals, millet, coix, buckwheat, quinoa, oat, and grain sorghum, of which 768 metabolites are identified. Moreover, quinoa and buckwheat showed significantly different metabolomic profiles compared with other coarse cereals. Analysis of the accumulation patterns of common nutritional metabolites among six coarse cereals, we found that the accumulation of carbohydrates follows a conserved pattern in the six coarse cereals, while those of amino acids, vitamins, flavonoids, and lipids were complementary. Furthermore, the species-specific metabolites in each coarse cereal were identified, and the neighbor-joining tree for the six coarse cereals was constructed based on the metabolome data. Since sorghum contains more species-specific metabolites and occupies a unique position on the neighbor-joining tree, the metabolite differences between grain sorghum 654 and sweet sorghum LTR108 were finally compared specifically, revealing that LTR108 contained more flavonoids and had higher antioxidant activity than 654. Our work supports an overview understanding of nutrient value in different coarse cereals, which provides the metabolomic evidence for the healthy diet. Additionally, the superior antioxidant activity of sweet sorghum provides clues for its targeted uses.
Article
Objectives: To assess the association of whole grain consumption with the risk of incident knee osteoarthritis (OA). Methods: We followed 2,846 participants in the Osteoarthritis Initiative aged 45 to 79 years. Participants were free from radiographic knee OA (Kellgren-Lawrence grade < 2) in at least one knee at baseline. Dietary data from baseline were obtained using the Block Brief Food Frequency Questionnaire. We defined radiographic knee OA incidence as Kellgren-Lawrence grade ≥ 2 during the subsequent 96 months. Cox proportional hazards models were used to assess the association between whole-grain food intake and risk of incident knee OA. Results: During the 96-month follow-up, 518 participants (691 knees) developed incident radiographic knee OA. Higher total whole-grain consumption was significantly associated with a lower knee OA risk (HR quartile 4 vs 1 =0.66; 95% CI: 0.52, 0.84; p trend <0.01), after adjusting for demographic and socioeconomic factors, clinical factors, and other dietary factors related to OA. Consistently, a significant inverse association of dark bread consumption with knee OA risk was observed (HR quartile 4 vs 1 =0.68; 95% CI: 0.53, 0.87; p trend <0.01). In addition, we observed a significant inverse association between higher cereal fiber intake and reduced knee OA risk (HR quartile 4 vs 1 =0.61; 95% CI: 0.46, 0.81; p trend <0.01). Conclusion: Our findings revealed a significant inverse association of whole-grain consumption with knee OA risk. These findings provide evidence that eating a diet rich in whole grains may be a potential nutritional strategy to prevent knee OA.
Article
Full-text available
Saponins are one type of wide-spread defense compounds in plant kingdom and have been exploited for production of lead compounds with diverse pharmacological properties in drug discovery. Oats contain two unique steroidal saponins avenacosides A, 1, and B, 2. However, the chemical composition, the levels of these saponins in commercial oat products, and their health effects are still largely unknown. In this study, we directly purified five steroidal saponins (1-5) from a methanol extract of oat bran, characterized their structures by analyzing their MS and NMR spectra, and also tentatively identified 11 steroidal saponins (6-16) based on their tandem mass spectra (MSn: n = 2-3). Among the five purified saponins, 5 is a new compound and 4 is purified from oats for the first time. Using HPLC-MS techniques, a complete profile of oat steroidal saponins was determined, and the contents of the two primary steroidal saponins 1 and 2 were quantitated in fifteen different commercial oat products. The total levels of these two saponins vary from 49.6-443.0 mg/kg, and oat bran or oatmeal has higher levels of these two saponins than cold oat cereal. Furthermore, our results on the inhibitory effects of 1 and 2 against the growth of human colon cancer cells HCT-116 and HT-29 showed that both had weak activity, with 2 being more active than 1.
Article
Full-text available
Victorin C, a host-specific toxin produced by Helminthosporium victoriae, induced hydroxycinnamoyl-CoA:hydroxyanthranilate N-hydroxycinnamoyltransferase (HHT, EC 2.3.1) activity in oat leaves (Avena sativa L., a cultivar carrying Pc-2 gene). This enzyme activity catalyzes the final step of biosynthesis of oat phytoalexins, avenanthramides. The HHT activity was detected after 12 h of victorin C application and reached to a maximum by 18 h. The induction of HHT was dose-dependent. All of the putative precursors of avenanthramides acted as substrates for HHT. These findings indicate that the accumulation of avenanthramides by victorin C treatment is due to induction of HHT. The enzyme activity showed highest specificity to 5-hydroxyanthranilate for the anthranyl moiety, while feruloyl-CoA was most effective for cinnamoyl moiety. HHT induced by victorin C showed significantly lower affinity for anthranilic acid relative to the enzyme induced by oligo-N-acetylchitooligosaccharides, another elicitor, suggesting that isozymes of HHT occur in this plant.
Article
Full-text available
Numerous studies have shown that avenanthramides (AVAs), unique compounds found in oats, are strong antioxidants, though the mechanism of action remains unclear. Here, we investigated whether AVAs affect heme oxygenase-1 (HO-1) expression through the activation of Nrf2 translocation. We investigated the effects AVA 2c, 2f, and 2p on HK-2 cells, and found that AVAs could significantly increase HO-1 expression in both a dose- and time-dependent manner. Furthermore, we found that AVA-induced HO-1 expression is mediated by Nrf2 translocation. The addition of N-acetylcysteine (NAC), but not specific inhibitors of p38 (SB202190), PI3K (LY294002), and MEK1 (PD098059) attenuated AVA-induced HO-1 expression, demonstrating an important role for ROS, but not PI3K or MAPK activation, in activating the HO-1 pathway. Moreover, hydrogenation of the double bond of the functional α,β-unsaturated carbonyl group of AVAs eliminated their effects on HO-1 expression, suggesting that this group is crucial for the antioxidant activity of AVAs. Our results suggest a novel mechanism whereby AVAs exert an antioxidant function on human health. Further investigation of these markers in human is warranted to explore the beneficial health effects of whole grain oat intake. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.
Article
Full-text available
Rigorous exercise is known to generate reactive oxygen species (ROS) and inflict inflammatory response. The present study investigated whether dietary supplementation of avenanthramides (AVA) in oats would increase antioxidant protection and reduce inflammation in humans after an acute bout of eccentric exercise. Young women (age 18-30 years, N = 16) were randomly divided into two groups in a double-blinded fashion, receiving two cookies made of oat flour providing 9.2 mg AVA (AVA) or 0.4 mg AVA (Control, C) each day for 8 weeks. Before and after the dietary regimen each group of subjects ran downhill (DR) on a treadmill at -9 % grade for 1 h at a speed to elicit 75 % of maximal heart rate. Blood samples were collected at rest, immediately and 24 h post-DR. Before dietary supplementation plasma creatine kinase activity and tumor necrosis factor (TNF)-α concentration were increased immediately after DR (P < 0.05), whereas neutrophil respiratory burst (NRB) was elevated 24 h post-DR (P < 0.05). CK and TNF-α response to DR was abolished during post-supplementation tests in both AVA and C groups, whereas NRB was blunted only in AVA but not in C. Plasma interleukin-6 level and mononuclear cell nuclear factor (NF) κB activity were not affected by DR either before or after dietary supplementation, but were lowered 24 h post-DR in AVA versus C (P < 0.05). Both groups increased plasma total antioxidant activity following 8-week dietary regimen (P < 0.05), whereas only AVA group increased resting plasma glutathione (GSH) concentration (P < 0.05), decreased glutathione disulfide response to DR, and lowered erythrocyte GSH peroxidase activity (P < 0.05). Our data of pre- and post-supplementation difference reflect an interaction between repeated measure effect of eccentric exercise and AVA in diet. Long-term AVA supplementation can attenuate blood inflammation markers, decrease ROS generation and NFkB activation, and increased antioxidant capacity during an eccentric exercise bout.
Article
Full-text available
Avenanthramides (AVAs), which are found exclusively in oats, may play an important role in anti-inflammation and antiatherogenesis. Although the bioavailability of AVAs has been investigated previously, little is known about their metabolism. The aim of the present study was to investigate the metabolism of avenanthramide-C (2c), one of the major AVAs, in mice and by the human microbiota, as well as to elucidate the bioactivity of its major metabolites with the goal of finding new exposure markers to precisely reflect oat consumption. For the mouse study, 10 CF-1 female mice were divided into control (vehicle-treated) and 2c intragastrically treated (200 mg/kg) groups (5 mice/group). Twenty-four-hour urine and fecal samples were collected with use of metabolic cages. For the batch culture incubations, 2c was cultured with fecal slurries obtained from 6 human donors. Incubated samples were collected at various time points (0, 12, 24, 48, 72, 96, and 120 h). Metabolites were identified via HPLC with electrochemical detection and LC with electrospray ionization/mass spectrometry. To investigate whether 2c metabolites retain the biological effects of 2c, we compared their effects on the growth of and induction of apoptosis in HCT-116 human colon cancer cells. Eight metabolites were detected from the 2c-treated mouse urine samples. They were identified as 5-hydroxyanthranilic acid (M1), dihydrocaffeic acid (M2), caffeic acid (M3), dihydroferulic acid (M4), ferulic acid (M5), dihydroavenanthramide-C (M6), dihydroavenanthramide-B (M7), and avenanthramide-B (M8) via analysis of their MS(n) (n = 1-3) spectra. We found that the reduction of 2c's C7'-C8' double bond and the cleavage of its amide bond were the major metabolic routes. In the human microbiota study, 2c was converted into M1-M3 and M6. Moreover, interindividual differences in 2c metabolism were observed among the 6 human subjects. Subjects B, C, E, and F could rapidly metabolize 2c to M6, whereas subject D metabolized little 2c, even up to 120 h. In addition, only subjects A, B, and F could cleave the amide bond of 2c or M6 to form the cleaved metabolites. Furthermore, we showed that 2c and its major metabolite M6 are bioactive compounds against human colon cancer cells. M6 was more active than 2c with the half-inhibitory concentration (IC50) of 158 μM and could induce apoptosis at 200 μM. To our knowledge, the current study demonstrates for the first time that avenanthramide-C can be extensively metabolized by mice and the human microbiota to generate bioactive metabolites. © 2015 American Society for Nutrition.
Article
Full-text available
Using an in vitro digestion model, we studied the effect of six saponin extracts on the bioaccessibility of cholesterol and saturated fatty acids (SFAs). In the absence of saponins, around 78% of the available cholesterol was solubilized in the simulated intestinal fluids. The addition of two extracts, Quillaja Dry (QD) and Sapindin (SAP), was found to decrease cholesterol bioaccessibility to 19% and 44%, respectively. For both extracts, the main mechanism of this effect is the displacement of cholesterol molecules from the bile salt micelles, leading to formation of cholesterol precipitates that cannot pass through the mucus layer of the intestine. QD decreased strongly the SFA bioaccessibility as well, from 69 to 9%, due to formation of calcium-SFA precipitates, while SAP had no effect on SFA. We studied the in vivo activity of QD and SAP extracts by measuring serum cholesterol in mice fed with experimental diets within a 7-day period. Both extracts were found to prevent dietary hypercholesterolemia in mice fed on a cholesterol-rich diet. The other saponin extracts did not show any significant effect in vitro and, therefore, were not studied in vivo. The cholesterol lowering ability of Sapindin extract is reported for the first time in the current study.
Article
The aim of the present study was to investigate whether oat saponins (avenacosides A and B) have any effect on the permeability of the rat intestine to actively and passively transported markers in vitro and in vivo. Intestinal segments were mounted in modified Ussing chambers, and the passage of the different marker compounds from the mucosal to the serosal side was measured for 120 min. Avenacosides (1 mg/ml) gave a significantly higher passage of the macromolecule ovalbumin and there was a tendency to increased passage of [ 14C]D-mannitol and [ 51Cr]EDTA. On the other hand, the saponins did not affect the active transport of [ 3H]methyl glucose. When rats were given saponins (40 mg/kg body weight) together with markers by gastric intubation, the passage of [ 51Cr]EDTA into blood and urine was somewhat reduced. For the macromolecule bovine serum albumin, no evident effect on the passage was observed in the presence of saponins. Thus, in contrast to the in vitro results, the in vivo marker passage seemed to be unaffected or even reduced in the presence of avenacosides. The study shows that saponins can affect the permeability of the rat intestine. However, this effect needs further investigation in vivo, especially regarding proteins.