Process Biochemistry 41 (2006) 19131923

www.elsevier.com/locate/procbio

Review

Advances in the manufacture, purification and applications

of xylo-oligosaccharides as food additives and nutraceuticals
Andres Moure *, Patricia Gullon, Herminia Domnguez, Juan Carlos Parajo
Chemical Engineering Department, University of Vigo (Campus Ourense), As Lagoas, 32004 Ourense, Spain
Received 16 March 2006; received in revised form 4 May 2006; accepted 10 May 2006

Abstract
Recent developments on the manufacture, purification and biological effects of xylo-oligosaccharides are reviewed. Xylo-oligosaccharides
(XO) can be produced by chemical and/or enzymatic methods from a variety of xylan-containing raw materials, and then refined by
physicochemical treatments. Considered as food ingredients, xylo-oligosaccharides have favourable technological properties and cause prebiotic
effects derived from their ability to modulate the intestinal function. Besides the effects related to their effects in the large bowel, a range of
additional biological activities have been reported for XO. Other topic discussed include the utilization of XO in synbiotic preparations, their
technological properties and market perspectives.
# 2006 Elsevier Ltd. All rights reserved.
Keywords: Xylo-oligosaccharides; Xylanases; Hydrothermal treatments; Refining; Biological effects

Contents
1.
2.
3.
4.
5.
6.
7.

Biomass, xylan and xylan hydrolysis products. . . . . . . . . . . . . . . . . . . . . . . .

Autohydrolysis of lignocellulosic materials for producing xylo-oligosaccharides
Refining of XO . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Intestinal action of XO . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Other properties of XO. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Other biological effects of XO . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Economic and market considerations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Acknowledgement . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

1. Biomass, xylan and xylan hydrolysis products

Biomass from plant material is the most abundant and
widely spread renewable raw material for the sustainable
production of clean and affordable biofuels, biopower, and
high-value bioproducts. Lignocellulosic materials (LCM) from
forest, agriculture, set-aside lands, industry or urban solid
wastes, mainly made up lignin, cellulose and hemicelluloses,
are potential feedstocks for chemical utilization.

* Corresponding author. Tel.: +34 988 3870082; fax: +34 988 387001.
E-mail address: amoure@uvigo.es (A. Moure).
1359-5113/$ see front matter # 2006 Elsevier Ltd. All rights reserved.
doi:10.1016/j.procbio.2006.05.011

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

.
.
.
.
.
.
.
.
.

1913
1915
1915
1917
1918
1920
1920
1920
1921

LCM are heterogeneous and present a complex chemical

nature. Their integral benefit can be achieved by chemical
fractionation, following the biomass refining philosophy [1],
based on the selective separation of the main components to
yield a variety of high added-value bioproducts.
The most abundant hemicellulosic polymers are xylans,
made up of xylose units. Xylans represent an immense resource
of biopolymers for practical applications, accounting for 25
35% of the dry biomass of woody tissues of dicots and lignified
tissues of monocots, and occur up to 50% in some tissues of
cereal grains. The structure of xylans depends on the source
considered. The most common xylans are made up of a main
backbone of xylose linked by b-1!4 bonds, where the

1914

A. Moure et al. / Process Biochemistry 41 (2006) 19131923

Table 1
Recent literature on hydrothermal processing of xylan-containing feedstocks
Raw material

Processing

Objectives of the work

References

Crop residues (corncobs)

Two-step aqueous treatment

(100140 8C and below 200 8C,
respectively)
Hydrothermal processing
at 200 8C
Non-isothermal hydrothermal
treatments up to 224 8C
Hydrothermal treatment under optimal
conditions for XO production
One- or two-stage hydrothermal
treatments for optimal XO yield
Aqueous treatments in microwave
oven at 180 8C
Hydrothermal treatment under optimal
conditions for XO production
Isothermal hydrothermal treatments at
temperatures in the range 145190 8C
Hydrothermal treatments at
temperatures in the range 150190 8C
Hydrothermal treatment under optimal
conditions for XO production
Aqueous treatments under optimized
conditions for the production of oligomers
Non-isothermal hydrothermal treatments
up to 220 8C
Hydrothermal treatments at temperatures
in the range 150190 8C
Hydrothermal treatments at temperatures
in the range 150190 8C
Hydrothermal treatments at temperatures
in the range 150190 8C
Hydrothermal treatments for fractionation
(optimal temperature, 190 8C)
Aqueous fractionation at 200 8C in flowand batch-reactors
Hydrothermal processing at 160 8C for
hemicellulose solubilization

Manufacture of XO by hydrothermal
processing and further refining

[27]

Assessment of the effects of the

solid to liquor ratio
Kinetics of hemicellulose decomposition
into oligomers and monomers
Comparative evaluation of substrates for
XO production and product characterization
Manufacture of XO by hydrothermal
processing and further refining
Product purification and structural
characterization
Comparative evaluation of substrates for
XO production and product characterization
Study of fractionation effects

[28]

Kinetics of hemicellulose decomposition

into oligomers and monomers
Comparative evaluation of substrates for
XO production and product characterization
Manufacture of XO by hydrothermal
processing and further refining
Kinetics of hemicellulose decomposition
and byproduct characterization
Oligomer generation for further
manufacture of fermentation media
Kinetics of hemicellulose decomposition
into oligomers and monomers
Kinetics of hemicellulose decomposition
into oligomers and monomers
Optimization of the enzymatic digestibility
of spent solids from autohydrolysis
Comparative evaluation of reaction
technologies
Manufacture of oligosaccharide solutions
for further conversion into monosaccharides
with a macroreticular strong cation exchanger
Comparative evaluation of substrates for
XO production and product characterization
Kinetics of hemicellulose decomposition
into oligomers and monomers
Manufacture of XO by hydrothermal
processing and further refining
Manufacture of water-soluble compounds
from hemicelluloses

[34]

Sugarcane bagasse
Eucalyptus globulus wood
E. globulus wood
E. globulus wood
Aspen wood
Corncobs
Corncobs
Corncobs
Barley hulls
Barley hulls
Barley hulls
Brewery spent grains
Brewery spent grains
Almond shells
Corn stover
Corn stover
Corn fiber

Rice hulls
Rice hulls
Rice hulls
Rice hulls

Rice hulls

Flax shive

Wheat straw
Bamboo

Hydrothermal treatment under optimal

conditions for XO production
Non-isothermal hydrothermal treatments
up to 225 8C
Aqueous treatments under optimal
conditions for the production of oligomers
Hydrothermal treatments in a
percolation reactor at temperatures
in the range 140220 8C
Two-step aqueous treatment
(120 and 198 8C, respectively) for
hydrolysis of hemicellulose
and susceptible lignin
Aqueous treatments in microwave oven
for partial depolymerization and
solubilization of hemicelluloses
Steam explosion at temperatures in the
range 200220 8C
Hydrothermal processing in a percolation
reactor at temperatures in the
range 175180 8C

[29]
[30]
[31]
[32]
[30]
[33]

[30]
[35]
[36]
[37]
[38]
[25]
[16]
[22]
[39]

[30]
[40]
[41]
[19]

Production of high-DP xylan oligosaccharides

and water-soluble lignins

[42]

Structural characterization of
hemicellulose-derived products

[43]

Characterisation of degraded
hemicellulosic polymers
Optimization of XO production

[44]
[45]

A. Moure et al. / Process Biochemistry 41 (2006) 19131923

structural units are often substituted at positions C2 or C3 with

arabinofuranosyl, 4-O-methylglucuronic acid, acetyl or phenolic substituents [2].
2. Autohydrolysis of lignocellulosic materials for
producing xylo-oligosaccharides
Xylo-oligosaccharides (XO) are produced from xylancontaining LCM by chemical methods (for example, by
autohydrolysis with water or steam or in media catalyzed with
externally added mineral acids), direct enzymatic hydrolysis of
a susceptible substrate [38] or a combination of chemical and
enzymatic treatments [6,913].
The state of the art on the manufacture and applications of XO
until 2000 was reviewed previously [14]. This work aims to
provide an overview of the recent developments in the same field,
devoting a particular interest to processes involving at least one
aqueous treatment (with hot, compressed water or steam) to
cause the degradation of xylan to soluble carbohydrates.
When the aqueous processing of xylan-containing LCM
(autohydrolysis or hydrothermal treatment) is carried out under
suitable operational conditions, the hemicellulosic chains are
progressively broken down by the hydrolytic action of
hydronium ions (generated from water autoionization and
from in situ generated organic acids), yielding soluble products
(mainly oligosaccharides), and leaving both cellulose and
lignin in solid phase with little chemical alteration.
The spent solids from autohydrolysis are suitable for further
utilization, for example enzymatic hydrolysis of cellulose [15
22], utilization for feed or fuel, or as a construction material
[23]. In this field, it can be noted that multiproduct processes
from lignocellulosic materials (according to the biorefiney
approach) present better economic perspectives, and decrease
greenhouse gas emissions in agreement with the objectives of
the Kyoto Protocol [24].
The main soluble products from autohydrolysis reactions are
usually referred as oligosaccharides, even if they may
present a broad distribution of molecular weights [25]. The
term oligosaccharide is usually reserved for DP in the range
310 [26], whereas fractions of higher molecular weight can
been considered as dietary fiber. However, the definition of
this latter term has seen several revisions since it was proposed
in 1953, and a variety of definitions are available based either
on analytical determination by specific methods or on their
biological effects, leading to some confusion between the
concepts of oligosaccharide and dietary fiber. For
example, the definitions of dietary fiber by the American
Association of Cereal Chemists in 2000 assumes that
oligosaccharides makes part of dietary fiber, whereas the
National Academy of Science classified in 2002 the isolated,
non-digestible carbohydrates as functional fiber, including
oligosaccharides and compounds with higher molecular weight
[26]. Considering that the only chemical difference between
polymeric and oligomeric xylan-degradation products is the
DP, and that xylobiose (DP2) has been considered as an
oligosaccharide in food studies [14], the whole set of soluble
fragments from xylan hydrolysis (with a broad range of DP, the

1915

major fractions corresponding usually to DP
20) has been

denoted as xylo-oligosaccharides (XO) or substituted
oligosaccharides, particularly in studies where the distribution
of molecular weights was unknown.
Recent studies have been reported on the manufacture of XO
by chemical processing of a variety of feedstocks, including
crop residues [27], sugarcane bagasse [28], hardwoods [2932],
corncobs [30,33,34], barley hulls [30,35,36], brewery spent
grains [37,38], almond shells [25], corn stover and corn fiber
[16,22,39], rice hulls [19,30,4042], flax shive [43], wheat
straw [44] and bamboo [45]. Table 1 summarizes information
on this topic.
In autohydrolysis treatments, XO behave as typical reaction
intermediates, and their maximum concentration is achieved
under medium-severity conditions. The molecular weight
distribution depends on both the substrate employed and the
reaction conditions. Treatments of increased severity lead to
decreased degrees of polymerization, but also to increased
decomposition of XO into xylose. Kinetic studies dealing with
XO production from a variety of substrates have been recently
reported [25,29,34,36,37,40].
XO obtained by autohydrolysis present a rich substitution
pattern, conserving the major structural features of the native
xylan [46,47]. For example, only a part of the ester groups are
split in hydrothermal treatments, in comparison with the
saponification caused by processes involving alkaline stages.
Detailed structural information has been reported for XO
obtained from several sources, using techniques such as highperformance anion-exchange chromatography (HPAEC),
matrix-assisted laser desorption/ionization time-of-flight mass
spectrometry (MALDI-TOF MS), reversed phase chromatography (RPC), LCMS and electro- and nanospray-MS, 1H and
13
C NMR homonuclear and heteronuclear two-dimensional
techniques and SEC [32,43,4654], allowing the identification
and quantification of XO substituents, as well as their locations
in the xylopyranose rings.
3. Refining of XO
When XO are produced by water or steam treatments, a
variety of other compounds (including monosaccharides, acetic
acid, products derived from the extractive and acid-soluble
lignin fractions of the feedstock, furfural from pentose
dehydration, soluble inorganic components of the feedstock,
and protein-derived products) appear in the reaction media
[35,41].
In order to produce food-grade XO, the autohydrolysis
liquors have to be refined by removing both monosaccharides
and non-saccharide compounds, to obtain a concentrate with an
XO content as high as possible. The usual purity of commercial
XO lies in the range 7595%. Purification of XO obtained by
enzymatic processing of substrates containing susceptible
xylan is facilitated by the previous chemical processing of the
lignocellulosic raw material as well as by the specific action of
xylanases.
Purification of autohydrolysis liquors is a complex problem,
and may require multistage processing for reaction and/or

1916

A. Moure et al. / Process Biochemistry 41 (2006) 19131923

fractionation. For example, in single-stage autohydrolysis

reactions, a significant part of the dissolved feedstock
corresponds to easily extractable compounds (for example,
waxes, low molecular weight phenolics and soluble inorganic
components), which could be removed by a previous, mild
hydrothermal treatment leaving the hemicellulosic polymers
almost untouched and ready for further hydrolytic conversion
under harsher conditions. Based on this idea, two consecutive
aqueous treatments of increasing severity (the first one
intending the removal of easily extractable compounds, and
the second one intending the selective solubilization of
hemicelluloses) have been performed to obtain either XO with
improved purity or solutions with enhanced susceptibility to
further refining treatments [27,31,42].
Some processing schemes start with a vacuum evaporation
stage in order to both increase the XO concentration and
remove undesired, volatile components.
Solvent extraction is useful for removing non-saccharide
components of autohydrolysis liquors [35,41,31], yielding both
a selectively refined aqueous phase and a solvent-soluble
fraction mainly made up of phenolics and extractive-derived
compounds. Antioxidant properties have been reported for the
ethyl acetate-soluble components of liquors from hydrolytic
processing of biomass [5557], suggesting the possibility of
achieving an integrated benefit of the several fractions from
autohydrolysis of lignocellulosics (oligosaccharide-containing
aqueous phase from solvent extraction of liquors, antioxidantcontaining organic phase from solvent extraction of liquors and
cellulose-enriched solid phase from autohydrolysis treatments)
as depicted in Fig. 1.
Solvent precipitation of liquors has been employed for
refining XO using ethanol, acetone and 2-propanol
[31,35,41,58]. The degree of purification and the recovery
yield depends on the solvent employed and on the lignocellulose raw material, which control the XO substitution pattern
and the possible presence of stabilising, non-saccharide
components [31].
As the presence of even minimal amounts of water limits the
precipitation of hemicellulose-derived products, solvent
extraction of freeze-dried autohydrolysis liquors has been
carried out using the same solvents employed for precipitation
[31,35,41]. The best purification effects were achieved with
ethanol, but the process showed limited recovery yields [31].
Adsorption has been used in combination with other treatments
for the refining of XO, intending either the separation of oligofrom mono-saccharides [14,59,60] or the removal of undesired
compounds [6,11,12,61].
Chromatographic separation has been carried out for XO
purification at an analytical level, yielding high purity fractions.
For example, samples from hydrothermally treated lignocellulosics have been fractionated by anion-exchange chromatography and size-exclusion chromatography [48,49], whereas
chromatographic techniques have been employed for refining
samples before structural characterization of XO, for example by
13
C NMR [7] or MALDI-TOF or nanospray mass spectrometry
[48]. Simulated moving bed, chromatographic separation has
also been proposed for purification of oligosaccharides made up

Fig. 1. Scheme of a possible process for utilization of xylan-containing

lignocellulosic materials.

of xylose and arabinose units [59], whereas size-exclusion

chromatography has been employed in combination with other
techniques for purification of feruloylated oligosaccharides [62].
Jacobs et al. [43] purified hemicellulose-derived products from
hydrothermal microwave treatments of flax shive employing ionexchange chromatography and/or size-exclusion chromatography in combination with enzymic processing.
Ion exchange has been employed for purification of XO
[6,12,27,35,41,61,63,64] alone or in multi-step processing,
looking mainly for desalination and removal of other undesired
compounds.
Membranes are gaining importance in XO technology for a
variety of purposes, including generation by enzymatic
reactions [65,66], refining and concentration. Ultrafiltration
has been employed as an alternative to ethanol precipitation for
isolation of arabinoxylo-oligosaccharides from enzymically
hydrolyzed arabinoxylan [58], leading to fractions with similar
degree of polymerization and degree of substitution than the
precipitated ones. Izumi et al. [8] employed membranes for
concentrating enzymatic hydrolyzates of lignocellulose pulp,
and Yuan et al. [11] employed nanofiltration membranes for
concentrating XO obtained by enzymatic breakdown of xylan
from steamed corncobs, whereas concentration and fractionation of XO by sequential membrane-based steps has been
employed in multistage purification processes [6,12]. Related
membrane studies have been reported for the separation of
glucose from lactose [67], separation of monosaccharide from

A. Moure et al. / Process Biochemistry 41 (2006) 19131923

di- and oligo-saccharides from hydrolyzed starch media [68],

purification of galacto-oligosaccharides [69] and fructooligosaccharides [70,71] by nanofiltration, removal of monosaccharides from oligosaccharide fractions of honey [60],
combined ultrafiltration and nanofiltration processing of fructooligosaccharides and inulopolysaccharides [72,73], synthesis
of galactosyl-oligosaccharides from lactose [74], recovery of
milk oligosaccharides [75], separation of pectate oligosaccharides from enzymically hydrolyzed pectate [76], purification of
oligosaccharides from defatted soybean meal [77], purification
of oligosaccharides from milk [78] and production of lowlactose milk containing oligosaccharides [79].

1917

Multiple purification steps can be necessary for achieving

high-purity XO. Table 2 summarizes information on representative processes studied for this purpose.
4. Intestinal action of XO
There is increasing awareness that the human gut microflora
plays a critical role in maintaining host health, both within the
gastrointestinal tract and systemically through the absorption of
metabolites. Although little is known about the individual
species of bacteria responsible for these beneficial activities, it
is generally accepted that the bifidobacteria and lactobacilli

Table 2
Purification processes considered in literature for xylo-oligosaccharide refining
Substrate

Method for XO generation

Other process stages

References

Pulp slurry

Enzymatic/acid hydrolysis

[6,12,61]

Birchwood xylan

Enzymatic hydrolysis

Corncobs

Steaming and enzymic

hydrolysis
Two-stage hydrothermal
treatment
One- or two-step
hydrothermal treatments

Concentration (reverse osmosis),

filtration, ultrafiltration, adsorption,
ion exchange, spray-drying
Anion-exchange and size-exclusion
chromatography
Flocculation, ion exchange,
nanofiltration, adsorption, evaporation
Filtration, concentration, adsorption,
ion exchange
Concentration, solvent (ethyl acetate)
extraction, solvent (ethanol, 2-propanol,
acetone) precipitation
Solvent (ethyl acetate) extraction,
evaporation, freeze-drying, solvent
(ethanol, 2-propanol, acetone) extraction
Evaporation, ethyl acetate extraction,
solvent (ethanol, 2 propanol, acetone)
precipitation
Evaporation, ethyl acetate extraction,
freeze drying, solvent (ethanol, 2-propanol,
acetone) extraction
Evaporation, ethyl acetate extraction,
ion exchange
Evaporation, ethyl acetate extraction,
solvent (ethanol, 2-propanol, acetone)
precipitation
Evaporation, ethyl acetate extraction,
freeze drying, solvent (ethanol, 2-propanol,
acetone) extraction
Evaporation, ethyl acetate extraction,
ion exchange
Ion-exchange chromatography,
enzymatic processing and/or size-exclusion
chromatography
Graded ethanol precipitation
Ultrafiltration with membranes of
different cut-off
Chromatography (simulated
moving-bed system)
Anion-exchange and size-exclusion
chromatography
Ion exchange

Corncobs
E. globulus wood

E. globulus wood

One- or two-step
hydrothermal treatments

Barley husks

Hydrothermal treatments

Barley husks

Hydrothermal treatments

Barley husks

Hydrothermal treatments

Rice husks

Hydrothermal treatments

Rice husks

Hydrothermal treatments

Rice husks

Hydrothermal treatments

Flax shive

Hydrothermal microwave
treatments

Wheat
Wheat

Enzymatic hydrolysis
Enzymatic hydrolysis

Plant tissues

Hydrolysis liquors containing

oligo- and mono-saccharides
Enzymatic hydrolysis

Wheat arabinoxylan
Biomass
Wheat bran
Xylan

Steam explosion and further

hydrolysis
Enzymatic hydrolysis
Enzymatic hydrolysis

Xylan

Enzymatic hydrolysis

Ion exchange
Membrane reactor for one-step generation
and fractionation of XO
Membrane reactor for one-step generation
and fractionation of XO

[7]
[11]
[27]
[31]

[31]

[35]

[35]

[35]
[41]

[41]

[41]
[43]

[58]
[58]
[59]
[62]
[63]
[64]
[65]
[66]

1918

A. Moure et al. / Process Biochemistry 41 (2006) 19131923

constitute important components of the beneficial gut microflora [80].

XO cause prebiotic effects when ingested as part of the diet
(for example, as active ingredients of functional foods) through
the modulation of colonic microflora. From a nutritional point
of view, XO behave as non-digestible oligosaccharides
(NDOs) (also named short-chain carbohydrates SCCs) [81],
and show biological effects related to the ones caused by other
oligosaccharides, such as fructo-oligosaccharides, galactooligosaccharides, soybean-oligosaccharides, and isomaltooligosaccharides. Recent experimental and review articles
are available on the prebiotic action of various types of
oligosaccharides, including XO [80,8288].
As NDOs, XO are not degraded by the low-pH gastric fluid
and digestive enzymes, being metabolised in large bowel. The
colonic fermentation of carbohydrates is a complex problem,
because the end products of the metabolism of given bacterial
species can be used as a substrate by others, and some
microorganisms may grow upon substrates that they are not
able to ferment. The prebiotic character of XO is mainly related
to their ability to specifically stimulate the growth of beneficial
bacteria (bifidobacteria and lactobacilli). An in vitro evaluation
of commercial prebiotic oligosaccharides concluded that XO
increased the number of Bifidobacteria, with comparative
advantage respect to other oligosaccharides [84]. The selective
utilization of XO as a carbon source by beneficial bacteria has
been reported by Crittenden et al. [89], who found that many
Bifidobacterium species and Lactobacillus brevis were able to
grow to high yields using XO, which were also efficiently
fermented by some bacteroides isolates but not by E. coli,
Enterococci, Clostridium difficile or Clostridium perfringens.
The ability of XO with degrees of polymerization in the range
210 to increase the number of Bifidobacterium and to suppress
the growth of Clostridium has been claimed [9]. A recent study
[90] reported beneficial effects of XO derived not only from
their ability to increase the populations of bifidobacteria and
lactobacilli, but also from the reduction in concentrations of
secondary bile acids, which exert a negative action on colon and
present a dose-dependent toxic potential related to their comutagenic and tumor-promoting properties. Decreased production of secondary bile acids during the digestive process has
been claimed for dietary supplements comprising XO and
physiologically active fatty acids [91].
Besides microbial growth, the colonic XO fermentation
leads to the production of CO2, H2, short chain fatty acids
(acetate, propionate and butyrate, denoted SCFA) and lactate.
These latter may be further metabolised systemically or locally
to provide energy generation for the host. A number of health
effects have been reported for SCFA, including improvement in
bowel function, calcium absorption, lipid metabolism and
reduction of the risk of colon cancer [92], serving as fuel in
different tissues and playing a potential role in the regulation of
cellular processes [93].
Focusing on the effects of XO in gut, studies in rats proved
the ability of feruloyl oligosaccharides for stimulating the
growth of Bifidobacterium bifidum [94], and showed a higher
bioavailability of bound ferulic acid in comparison with the free

compound [95], causing favourable effects on the intestinal

microbiota that may affect the development of precancerous
colonic lesions [96].
Earlier in vitro studies with low-DP, linear XO were
followed by further assays with complex XO to highlight the
effects of molecular weight and structure (including the
presence and type of substituents) on their colonic degradation
patterns. The effects of XO structure on degradability were
assessed by Van Laere et al. [97], who tested the breakdown of
linear and arabinose-containing XO by several strains of
Bifidobacterium, Clostridium, Bacteroides, and Lactobacillus.
The slower fermentation of branched XO respect to linear XO
led to higher butyric acid production, which may result in even
more advantageous effects [98], whereas the presence of
feruloyl substituents may promote the growth of beneficial
bacteria [94]. Kabel et al. [49] studied the fermentation of four
different types of XO (acetylated, linear, substituted with
uronic acids and arabino-XO) by faecal inocula, finding that
linear- and arabino-XO were fermented quickly than the other
substrates during the first 20 h, and that after this adaptation
time, the degradation rate was the same for all the substrates
tested. Fermentation resulted in increased cell material and in
accumulation of relatively high substituted XO with DP in the
range 57. SCFA and lactate were formed during the
fermentation and their concentrations increased with the
consumption of total XOS. The fermentation presented two
stages, the first one leading mainly to the formation of acetate
and lactate, and the second one leading to the production of
butyrate and propionate.
5. Other properties of XO
Considered as food ingredients, XO show favourable
technological features, including stability in acidic media,
resistance to heat, and ability for offering lower available
energy and for achieving significant biological effects at low
daily intakes. XO are non-cariogenic, save insulin secretion
from the pancreas and stimulate intestinal mineral absorption
[99]. XO can affect bowel habit and are mildly laxative
through stimulation of bacterial growth and fermentation
[81]. A sufficiently high, regular ingestion may cause
diarrhoea due to osmogenic retention of fluid in both the
small and large intestines, which disappears within a few days
because of the increase in population of intestinal microbes
able to readily utilize XO. Although the maximum
permissible dose depends on individual factors, it has been
estimated in 0.12 g/kg body weight for male Japanese adults
[99]. A controlled administration of XO may help to restrain
the growth of pathogenic bacteria, to retard disorders caused
by imbalanced fermentation in colon [100] and to avoid
intestinal disorders such as constipation, inflammatory bowel
disease, diarrhoea and gastritis [101,102]. XO intake has been
found highly effective for the reduction of severe constipation
in pregnant women without adverse effects [103]. Nutritional
infant formulae containing XO have been claimed to have
synergistic effects all along the intestinal tract, improving gut
barrier maturation [104]. XO can be mixed with other

A. Moure et al. / Process Biochemistry 41 (2006) 19131923

1919

Table 3
Recently reported biological activities of XO additional to those related to their modulatory gut effects
Manufacture, substrate

Biological effect or application

References

Hydrothermal treatment
of rice hulls
Enzymatic hydrolysis
of wheat flour arabinoxylan
Enzymatic hydrolysis
of wheat bran
Hydrothermal processing
of bagassse and enzymatic
processing
Feruloyl xylo-oligosaccharides
from enzymatic reactions
Active principles of
pharmaceutical preparations
Mixtures of XO and
tea catechins
Active component of synbiotic
preparations with Lactobacillus
strains
Active component of
pharmaceutical preparations
with flavonoids
Enzymatic hydrolysates
of rice bran
Enzymatic hydrolysates
of wheat flour arabinoxylan
XO with DP 520 as active
components of enteral
nutrition preparation
Long chain XO from enzymatic
processing of lignocellulosic
materials
Acidic xylo-oligosaccharides
Acidic xylo-oligosaccharides
containing uronic acid residues
Acidic xylo-oligosaccharides from
chemical and enzymatic processing
of hardwood pulp
Purified acidic xylo-oligosaccharides
from the enzymatic and/or
physicochemical processing of
hardwood pulp
Acidic xylo-oligosaccharides
from the enzymatic processing
of broadleaf pulp
Acidic xylo-oligosaccharides from
enzymatic and/or physicochemical
processing of lignocellulosic materials
Active principles of pharmaceutical
preparations
Acidic xylo-oligosaccharides
containing uronic acid residues
Chemicalenzymatic processing
of pulp slurry
Acidic xylo-oligosaccharides containing
uronic acid residues from enzymatic
processing of pulps
Acidic xylo-oligosaccharides containing
uronic acid residues from enzymatic
processing of pulps
Active components of pharmaceutical
preparations
Active components of pharmaceutical
preparations
Enzymatic processing of algae

Antioxidant (DPPH-radical scavenging)

activity
Antioxidant (DPPH-radical scavenging)
activity
Antioxidant activity (erythrocyte
hemolysis assay)
Antioxidant activity

[42,108]

Protective effect against lipid (LDL)

peroxidation
Prevention and treatment of
oxidative stress
Prevention and control of anemia
and arteriosclerosis
Treatment of vaginal and urogenital
infections

[4]

Low-glycemic index carbohydrate

substitute

[112]

Cosmetics

[113]

Prevention of atherosclerosis

[62]

Antihyperlipidemic activity

[114]

Hypolipemic activity (against cholesterol,

phospholipid and triglycerides)

[115]

Antihyperlipidemic activity
Hair growth stimulation

[116]
[117]

Inhibition of melanin and inhibition of

melanoma cell proliferation

[10]

Treatment of atopic dermatitis

[61,118]

Collagen production enhancer

[119]

Active components of moisturizing

preparations

[120]

Treatment of epithelial covering tissue

[121]

Anti-inflammatory activity

[122]

Therapeutic agents for osteoporosis

treatment
Hyaluronic acid-formation promoters

[123]

Histamine-release inhibitors

[125]

Increased absorption and/or bioavailability

of magnesium
Prevention of type II diabetes

[126]

Cancer cell apoptosis inducers

[128]

[62]
[64]
[109]

[110]
[102]
[111]

[124]

[127]

1920

A. Moure et al. / Process Biochemistry 41 (2006) 19131923

Table 3 (Continued )
Manufacture, substrate

Biological effect or application

References

Hydrothermal processing of bamboo

Selective cytotoxicity against acute

lymphoblastic leukemia cells
Antimicrobial activity against
Gram-positive
bacteria and against
Helicobacter pylori
Bacteriostatic action against
Vibrio anguillarum
Antiallergy agents

[129]

Oral cavity component with

antiplaque effect
Immunomodulating activity

[131]

Immunomodulatory action preventing

common cold syndrome
Prevention and treatment of
immune disorders

[133]

Acidic oligosaccharides from enzymatic

processing of birchwood xylan

Enzymatic and acid processing of

hardwood pulps
Acidic xylo-oligosaccharides
containing uronic acid residues
Active principles of pharmaceutical
preparations
Pharmaceutical preparations containing
acidic and neutral XO
Enzymatic processing of rice bran
Active principles of synbiotic
preparations

prebiotics to achieve synergistic effects or make part of

synbiotic preparations together with probiotic microorganisms. Recent patents have been issued on this latter topic
[105107].
6. Other biological effects of XO
XO (alone or as active components of pharmaceutical
preparations) exhibit a range of biological activities different
from the prebiotic effects related to gut modulation. Table 3
summarizes representative applications claimed in the last
few years, including antioxidant activity (conferred by
phenolic substituents), blood- and skin-related effects,
antiallergy, antimicrobial, anti-infection and anti-inflammatory properties, selective cytotoxic activity, immunomodulatory action, cosmetic and a variety of other properties. It
can be noted that a significant part of the recent
developments has been proposed for acidic oligosaccharides
containing uronic substituents, which can be produced from
hardwoods by a combination of enzymatic and/or chemical
treatments.
Besides biological effects concerning human health, XO
have been employed for phytopharmaceutical [3,4,135] and
feed [9,136] applications.
7. Economic and market considerations
The most important applications of XO in terms of current
and potential market demand correspond to ingredients for
functional foods (for example, in combination with soya
milk, soft drinks, tea or cocoa drinks, nutritive preparations,
dairy products with milk, milk powder and yoghurts, candies,
cakes, biscuits, pastries, puddings, jellies, jam and honey
products, and special preparations for health food for elder
people and children) or as active components of synbiotic
preparations. The origin of the term functional food can
be traced to Japan, where the concept of foods designed to be
medically beneficial to the consumer evolved during the

[4,7]

[9]
[130]

[132]

[134]

1980s. The term refers to the practice of fortifying foods with

added ingredients that can confer health effects on the
consumer [137]. The functional food market is growing
rapidly [138], based on the consumers awareness of the link
between health, nutrition, and diet as well as on the interest
of food manufacturers due to the increased value that the
added ingredients give to food. This is particularly applicable
to XO, for which a selling price of 2500 yen/kg has been
reported (the highest one among 13 different types of
oligosaccharides) [139]. The same reference reports a total
production of 650 ton of XO per year in Japan, which
accounts for about one-half of the world market. However,
the fastest growth rate is expected for the United States
market. The manufacture of probiotics is growing, but their
long-term exploitation as health promoters is dependent on
several factors, including sound, scientifically proven clinical
evidence of health-promoting activity, accurate consumer
information, effective marketing strategies, and, above all, a
quality product that fulfils consumer expectations [137]. The
modulation of the immune system by oligosaccharides and
their role in the reduction of lifestyle-related diseases as well
as the maintenance and improvement of human health has
been also cited as an area of growing importance [140]. With
the increasing health consciousness among consumers and
the rapid progress of physiologically active functional foods,
the future profile of products containing oligosaccharides
with biological activities seems to be greatly promising
[140].
Acknowledgments
Authors are grateful to the Spanish Ministry of Science of
Technology for the financial support of this work (in the
framework of the Research Project Development of
technologies for the integral benefit of industrial byproducts, reference CTQ2005-00745/PPQ, which had partial
financial support from the FEDER funds of the European
Union).

A. Moure et al. / Process Biochemistry 41 (2006) 19131923

References
[1] Myerly RC, Nicholson MD, Katzen R, Taylor JM. The forestry refinery.
Chemtech 1981;11:18692.
[2] Ebringerova A, Heinze T. Xylan and xylan derivatives, biopolymers with
valuable properties. 1. Naturally occurring xylans structures, isolation
procedures and properties. Macromol Rapid Commun 2000;21:54256.
[3] Katapodis P, Kavarnou A, Kintzios S, Pistola E, Kekos D, Macris BJ,
et al. Production of acidic xylo-oligosaccharides by a family 10 endoxylanase from Thermoascus aurantiacus and use as plant growth regulators. Biotechnol Lett 2002;24:14136.
[4] Katapodis P, Christakopoulos P. Xylanases as a tool for the production of
novel phytopharmaceuticals. NutraCos 2005;4:1721.
[5] Vardakou M, Katapodis P, Topakas E, Kekos D, Macris BJ, Christakopoulos P. Synergy between enzymes involved in the degradation of
insoluble wheat flour arabinoxylan. Innov Food Sci Emerg Technol
2004;5:10712.
[6] Izumi Y, Ikemizu S, Shizuka F. Intestinal environment improving agents
containing acidic xylooligosaccharides. Japan Patent JP 2,004,182,609;
2004.
[7] Christakopoulos P, Katapodis P, Kalogeris E, Kekos D, Macris BJ,
Stamatis H, et al. Antimicrobial activity of acidic xylo-oligosaccharides
produced by family 10 and 11 endoxylanases. Int J Biol Macromol
2003;31:1715.
[8] Izumi Y, Sugiura J, Kagawa H, Azumi N. Process for producing
xylooligosaccharide from lignocellulose pulp. U.S. Patent US
2,002,195,213; 2002.
[9] Izumi K, Azumi N. Xylooligosaccharide compositions useful as food and
feed additives. Japan Patent JP 2,001,226,409; 2001.
[10] Ikemizu S, Azumi N. Melanin formation inhibitors containing acidic
xylooligosaccharides. Japan Patent JP 200,217,137; 2002.
[11] Yuan QP, Zhang H, Qian ZM, Yang XJ. Pilot-plant production of xylooligosaccharides from corncob by steaming, enzymatic hydrolysis and
nanofiltration. J Chem Technol Biotechnol 2004;79:10739.
[12] Kokubo I, Izumi K, Shizuka F. Preventive agents for osteoporosis containing acidic xylooligosaccharides. Japan Patent JP 2,004,182,621; 2004.
[13] Yang R, Xu S, Wang Z, Yang W. Aqueous extraction of corncob xylan
and production of xylooligosaccharides. LWT-Food Sci Technol
2005;38:67782.
[14] Vazquez MJ, Alonso JL, Domnguez H, Parajo JC. Xylooligosaccharides: manufacture and applications. Trends Food Sci Technol 2000;11:
38793.
[15] Mosier NS, Hendrickson R, Brewer M, Ho N, Sedlak M, Dreshel R, et al.
Industrial scale-up of pH-controlled liquid hot water pretreatment of corn
fiber for fuel ethanol production. Appl Biochem Biotechnol 2005;125:
7797.
[16] Mosier N, Hendrickson R, Ho N, Sedlak M, Ladisch MR. Optimization
of pH controlled liquid hot water pretreatment of corn stover. Bioresour
Technol 2005;96:198693.
[17] Lasser M, Schulman D, Allen SG, Lichwa J, Antal MJ, Lynd LR. A
comparison of liquid hot water and steam pretreatments of sugar cane
bagasse for bioconversion to ethanol. Bioresour Technol 2001;81:3344.
[18] Rivas B, Moldes AB, Domnguez JM, Parajo JC. Lactic acid production
from corncobs by simultaneous saccharification and fermentation: a
mathematical interpretation. Enzyme Microb Technol 2004;34:62734.
[19] Kumagai S, Hayashi N, Sakai T, Nakada M, Shibata M. Fractionation and
saccharification of cellulose and hemicellulose in rice hull by hotcompressed-water treatment with two-step heating. J Jpn Inst Energy
2004;83:77681.
[20] Palmarola-Adrados B, Galbe M, Zacchi G. Pretreatment of barley husk
for bioethanol production. J Chem Technol Biotechnol 2005;80:85
91.
[21] Belkacemi K, Hamoudi S. Enzymatic hydrolysis of dissolved corn stalk
hemicelluloses: reaction kinetics and modeling. J Chem Technol Biotechnol 2003;78:8028.
[22] Liu C, Wyman CE. Partial flow of compressed-hot water through corn
stover to enhance hemicellulose sugar recovery and enzymatic digestibility of cellulose. Bioresour Technol 2005;96:197885.

1921

[23] Amaral-Collaco MT, Girio FM, Carvalheiro F, Esteves MP, Parajo JC,
Domnguez H, et al. Process for production of xylo-oligosaccharides for
use in the food industry, as chemical feedstocks and energy materials.
Port. Patent PT 102,563; 2002.
[24] Arato C, Pye EK, Gjennestad G. The lignol approach to biorefining of
woody biomass to produce ethanol and chemicals. Appl Biochem
Biotechnol 2005;121124:87182.
[25] Nabarlatz D, Farriol X, Montane D. Autohydrolysis of almond shells for
the production of xylo-oligosaccharides: product characteristics and
reaction kinetics. Ind Eng Chem Res 2005;44:774655.
[26] Tungland BC, Meyer D. Non-digestible oligo- and polysaccharides
(dietary fiber): their physiology and role in human health and food.
Compr Rev Food Sci Food Safety 2002;1:7392.
[27] Endo M, Kuroda Y. Production method of xylose and xylooligosaccharides from natural compounds containing xylan by hot water pretreatment. Japan Patent JP 2,000,236,899; 2000.
[28] Jacobsen SE, Wyman CE. Xylose monomer and oligomer yields for
uncatalyzed hydrolysis of sugarcane bagasse hemicellulose at varying
solids concentration. Ind Eng Chem Res 2002;41:145461.
[29] Garrote G, Parajo JC. Non-isothermal autohydrolysis of Eucalyptus
wood. Wood Sci Technol 2002;36:11123.
[30] Parajo JC, Garrote G, Cruz JM, Domnguez H. Production of xylooligosaccharides by autohydrolysis of lignocellulosic materials. Trends
Food Sci Technol 2004;15:11520.
[31] Vazquez MJ, Garrote G, Alonso JL, Domnguez H, Parajo JC. Refining of
autohydrolysis liquors for manufacturing xylooligosaccharides: evaluation of operational strategies. Bioresour Technol 2005;96:88996.
[32] Teleman A, Lundqvist J, Tjerneld F, Stalbrand H, Dahlman O. Characterization of acetylated 4-O-methylglucuronoxylan isolated from
aspen employing 1H and 13C NMR spectroscopy. Carbohydr Res
2000;329:80715.
[33] Garrote G, Domnguez H, Parajo JC. Fractionation of corncobs in
aqueous media. Afinidad 2002;59:35763.
[34] Nabarlatz D, Farriol X, Montane D. Kinetic modeling of the autohydrolysis of lignocellulosic biomass for the production of hemicellulosederived oligosaccharides. Ind Eng Chem Res 2004;43:412431.
[35] Vegas R, Alonso JL, Domnguez H, Parajo JC. Manufacture and refining
of oligosaccharides from industrial solid wastes. Ind Eng Chem Res
2005;44:61420.
[36] Garrote G, Domnguez H, Parajo JC. Production of substituted oligosaccharides by hydrolytic processing of barley husks. Ind Eng Chem Res
2004;43:160814.
[37] Carvalheiro F, Esteves MP, Parajo JC, Pereira H, Girio FM. Production of
oligosaccharides by autohydrolysis of brewerys spent grain. Bioresour
Technol 2004;91:93100.
[38] Carvalheiro F, Garrote G, Parajo JC, Pereira H, Girio FM. Kinetic
modeling of brewerys spent grain autohydrolysis. Biotechnol Progr
2005;21:23343.
[39] Kim Y, Hendrickson R, Mosier N, Ladisch MR. Plug-flow reactor for
continuous hydrolysis of glucans and xylans from pretreated corn fiber.
Energy Fuels 2005;19:2189200.
[40] Vila C, Garrote G, Domnguez H, Parajo JC. Hydrolytic processing of
rice husks in aqueous media: a kinetic assessment. Collect Czech Chem
Commun 2002;67:50930.
[41] Vegas R, Alonso JL, Domnguez H, Parajo JC. Processing of rice husk
autohydrolysis liquors for obtaining food ingredients. J Agric Food Chem
2004;52:73117.
[42] Hayashi N, Sakaki T, Doi K. Water-soluble saccharides useful as health
foods and their manufacture by hydrolysis of hemicellulose-containing
plants with pressurized hot water. Japan Patent JP 2,005,023,041; 2005.
[43] Jacobs A, Palm M, Zacchi G, Dahlman O. Isolation and characterization
of water-soluble hemicelluloses from flax shive. Carbohydr Res 2003;
338:186976.
[44] Sun XF, Xu F, Sun RC, Geng ZC, Fowler P, Baird MS. Characteristics of
degraded hemicellulosic polymers obtained from steam exploded wheat
straw. Carbohydr Polym 2005;60:1526.
[45] Ando H, Morita S, Furukawa I, Kamino Y, Sasaki T, Hirose H. Generation of xylooligosaccharides from moso bamboo (Phyllostachys

1922

[46]

[47]

[48]

[49]

[50]

[51]

[52]

[53]

[54]

[55]

[56]

[57]

[58]

[59]
[60]

[61]

[62]

[63]
[64]
[65]

[66]

A. Moure et al. / Process Biochemistry 41 (2006) 19131923

pubescens) using hot compressed water. Mokuzai Gakkaishi
2003;49:293300.
Kabel MA, Carvalheiro F, Garrote G, Avgerinos E, Koukios E, Parajo JC,
et al. Hydrothermally treated xylan rich by-products yield different
classes of xylo-oligosaccharides. Carbohydr Polym 2002;50:4752.
Kabel MA, Schols HA, Voragen AGJ. Mass determination of oligosaccharides by matrix-assisted laser desorption/ionization time-of-flight
mass spectrometry following HPLC, assisted by on-line desalting and
automated sample handling. Carbohydr Polym 2000;44:1615.
Kabel MA, Schols HA, Voragen AGJ. Structural features of acetylated
xylo-oligosaccharides. In: Proceedings of the 223rd ACS National
Meeting; 2002.
Kabel MA, Kortenoeven L, Schols HA, Voragen AGJ. In vitro fermentability of differently substituted xylooligosaccharides. J Agric Food
Chem 2002;50:620510.
Kabel MA, Schols HA, Voragen AGJ. Identification of structural features
of various (O-acetylated) xylo-oligosaccharides from xylan-rich agricultural by-products: a review. In: Proceedings of the ACS Symposium
Series, 864; 2004. p. 10821.
Reis A, Domingues MRM, Domingues P, Ferrer-Correia AJ, Coimbra
MA. Positive and negative electrospray ionization tandem mass spectrometry as a tool for structural characterization of acid released oligosaccharides from olive pulp glucuronoxylans. Carbohydr Res 2003;338:
1497505.
Reis A, Domingues MRM, Ferrer-Correia AJ, Coimbra MA. Structural
characterisation by MALDI-MS of olive xylo-oligosaccharides obtained
by partial acid hydrolysis. Carbohydr Polym 2003;53:1017.
Matamoros-Fernandez LE, Obel N, Scheller HV, Roepstorff P. Characterization of plant oligosaccharides by matrix-assisted laser desorption/ionization and electrospray mass spectrometry. J Mass
Spectrom 2003;38:42737.
Jacobs A, Lundqvist J, Stalbrand H, Tjerneld F, Dahlman O. Characterization of water-soluble hemicelluloses from spruce and aspen employing SEC/MALDI mass spectroscopy. Carbohydr Res 2002;337:7117.
Garrote G, Cruz JM, Moure A, Domnguez H, Parajo JC. Antioxidant
activity of byproducts from the hydrolytic processing of selected lignocellulosic materials. Trends Food Sci Technol 2004;15:191200.
Cruz JM, Domnguez H, Parajo JC. Antioxidant activity of isolates from
acid hydrolysates of Eucalyptus globulus wood. Food Chem 2005;90:
50311.
Garrote G, Cruz JM, Domnguez H, Parajo JC. Valorisation of waste
fractions from autohydrolysis of selected lignocellulosic materials. J
Chem Technol Biotechnol 2003;78:3928.
Swennen K, Courtin CM, Van der Bruggen B, Vandecasteele C, Delcour
JA. Ultrafiltration and ethanol precipitation for isolation of arabinoxylooligosaccharides with different structures. Carbohydr Polym
2005;62:28392.
Ohsaki S, Tamura M, Yamaura, T. Method for purification of saccharide.
U.S. Patent US 6,548,662; 2003.
Sanz ML, Polemis N, Morales V, Corzo N, Drakoularakou A, Gibson
GR, et al. In vitro investigation into the potential prebiotic activity of
honey oligosaccharides. J Agric Food Chem 2005;53:291421.
Izumi Y, Azumi N, Kido Y, Nakabo Y. Oral preparations for atopic
dermatitis containing acidic xylooligosaccharides. Japan Patent JP
2,004,210,666; 2004.
Katapodis P, Vardakou M, Kalogeris E, Kekos D, Macris BJ, Christakopoulos P. Enzymic production of a feruloylated oligosaccharide with
antioxidant activity from wheat flour arabinoxylan. Eur J Nutr
2003;42:5560.
Van Thorre D. Process for obtaining bio-functional fractions from
biomass. U.S. Pat. US 2004138445. 2004.07.15.
Yuan X, Wang J, Yao H. Antioxidant activity of feruloylated oligosaccharides from wheat bran. Food Chem 2005;90:75964.
Yang F, Fang Z, Xu Y, Yao C, Yu S, Zhu Q. Separation of xylooligosaccharides from enzymatic hydrolytes using membrane reactor.
J Central South Univ Technol 2003;10:1225.
Freixo MR, de Pinho MN. Enzymatic hydrolysis of beechwood xylan in a
membrane reactor. Desalination 2002;149:23742.

[67] Goulas AK, Grandison AS, Rastall RA. Fractionation of oligosaccharides by nanofiltration. J Sci Food Agric 2003;83:67580.
[68] Grandison AS, Goulas AK, Rastall RA. The use of dead-end and crossflow nanofiltration to purify prebiotic oligosaccharides from reaction
mixtures. Songklanakarin J Sci Technol 2002;24:91528.
[69] Goulas AK, Kapasakalidis PG, Sinclair HR, Rastall RA, Grandison AS.
Purification of oligosaccharides by nanofiltration. J Membr Sci
2002;209:32135.
[70] Li W, Li J, Chen T, Chen C. Study on nanofiltration for purifying fructooligosaccharides. J Membr Sci 2004;245:1239.
[71] Li W, Li J, Chen T, Zhao Z, Chen C. Study on nanofiltration for purifying
fructo-oligosaccharides. J Membr Sci 2005;258:815.
[72] Kamada T, Nakajima M, Nabetani H, Iwamoto S. Pilot-scale study of the
purification and concentration of non-digestible saccharides from yacon
rootstock using membrane technology. Food Sci Technol Res 2002;8:
1727.
[73] Kamada T, Nakajima M, Nabetani H, Saglam N, Iwamoto S. Availability
of membrane technology for purifying and concentrating oligosaccharides. Eur Food Res Technol 2002;214:43540.
[74] Czermak P, Ebrahimi M, Grau K, Netz S, Sawatzki G, Pfromm PH.
Membrane-assisted enzymatic production of galactosyl-oligosaccharides from lactose in a continuous process. J Membr Sci 2004;232:85
91.
[75] Sarney DB, Hale C, Frankel G, Vulfson EN. A novel approach to the
recovery of biologically active oligosaccharides from milk using a
combination of enzymatic treatment and nanofiltration. Biotechnol
Bioeng 2000;69:4617.
[76] Iwasaki K, Matsubara Y. Purification of pectate oligosaccharides showing root-growth-promoting activity in lettuce using ultrafiltration and
nanofiltration membranes. J Biosci Bioeng 2000;89:4957.
[77] Kim S, Kim W, Hwang IK. Optimization of the extraction and purification of oligosaccharides from defatted soybean meal. Int J Food Sci
Technol 2003;38:33742.
[78] Samhaber WM. Uses and setting of tasks of nanofiltration in the food
industry. Chem Ing Tech 2005;77:5838.
[79] Chen CS, Hsu CK, Chiang BH. Optimization of the enzymic process for
manufacturing low-lactose milk containing oligosaccharides. Process
Biochem 2002;38:8018.
[80] Tuohy KM, Rouzaud GCM, Brueck WM, Gibson GR. Modulation of the
human gut microflora towards improved health using prebioticsassessment of efficacy. Curr Pharm Des 2005;11:7590.
[81] Cummings JH, Macfarlane GT, Englyst HN. Prebiotic digestion and
fermentation. Am J Clin Nutr 2001;73:415S20S.
[82] Gibson GR, Probert HM, van Loo J, Rastall RA, Roberfroid MB. Dietary
modulation of the human colonic microbiota: updating the concept of
prebiotics. Nutr Res Rev 2004;17:25975.
[83] Rastall RA, Gibson GR. Prebiotic oligosaccharides: evaluation of biological activities and potential future developments. Probiot Prebiot
2002;10748.
[84] Rycroft CE, Jones MR, Gibson GR, Rastall RA. A comparative in vitro
evaluation of the fermentation properties of prebiotic oligosaccharides. J
Appl Microbiol 2001;91:87887.
[85] Playne MJ, Crittenden RG. Prebiotics from lactose, sucrose, starch, and
plant polysaccharides. Nutraceut Sci Technol 2004;2:99134.
[86] Meyer PD. Nondigestible oligosaccharides as dietary fiber. J AOAC Int
2004;87:71826.
[87] Palframan RJ, Gibson GR, Rastall RA. Carbohydrate preferences of
Bifidobacterium species isolated from the human gut. Curr Issues Intest
Microbiol 2003;4:715.
[88] Rastall RA, Maitin V. Prebiotics and synbiotics: towards the next
generation. Curr Opin Biotechnol 2002;13:4906.
[89] Crittenden R, Karppinen S, Ojanen S, Tenkanen M, Fagerstrom R, Matto
J, et al. In vitro fermentation of cereal dietary fibre carbohydrates by
probiotic and intestinal bacteria. J Sci Food Agric 2002;82:7819.
[90] Zampa A, Silvi S, Fabiani R, Morozzi G, Orpianesi C, Cresci A. Effects
of different digestible carbohydrates on bile acid metabolism and SCFA
production by human gut micro-flora grown in an in vitro semi-continuous culture. Anaerobe 2004;10:1926.

A. Moure et al. / Process Biochemistry 41 (2006) 19131923

[91] Rull PS. Dietary supplements comprising prebiotics and physiologically
active fatty acids. Eur. Patent EP 1,614,357; 2006.
[92] Scheppach W, Luehrs H, Menzel T. Beneficial health effects of lowdigestible carbohydrate consumption. Br J Nutr 2001;85:S2330.
[93] Blaut M. Relationship of prebiotics and food to intestinal microflora. Eur
J Nutr 2002;41:1/116.
[94] Yuan X, Wang J, Yao H. Feruloyl oligosaccharides stimulate the growth
of Bifidobacterium bifidum. Anaerobe 2005;11:2259.
[95] Rondini L, Peyrat-Maillard MN, Marsset-Baglieri A, Fromentin G, Durand
P, Tome D, et al. Bound ferulic acid from bran is more bioavailable than the
free compound in rats. J Agric Food Chem 2004;52:433843.
[96] Hsu CK, Liao JW, Chung YC, Hsieh CP, Chan YC. Xylooligosaccharides
and fructo-oligosaccharides affect the intestinal microbiota and precancerous colonic lesion development in rats. J Nutr 2004;134:15238.
[97] Van Laere KMJ, Hartemink R, Bosveld M, Schols HA, Voragen AGJ.
Fermentation of plant cell wall derived polysaccharides and their corresponding oligosaccharides by intestinal bacteria. J Agric Food Chem
2000;48:164452.
[98] Rantanen HK, Tuomainen P, Arpiainen J, Tenkanen M. Enzymatic
production of arabinoxylo-oligosaccharides and their fermentability
by probiotic bacteria. In: Proceedings of the 228th ACS National Meeting, American Chemical Society; 2004. p. 226.
[99] Oku T, Sadako N. Digestion, absorption, fermentation, and metabolism
of functional sugar substitutes and their available energy. Pure Appl
Chem 2002;74:125361.
[100] Rautonen N, Apajalahti J, Kettunen A, Siikanen O. Carbohydrates use for
treating diseases and/or disorders caused by imbalanced fermentation in
colon. Int. Patent WO 2004026316; 2004.
[101] Gibson GR, Beer M. Prebiotic compositions containing oligosaccharides
for control of intestinal disorders such as inflammatory bowel disease,
diarrhoea and constipation. Int. Patent WO 2,004,052,121; 2004.
[102] Matsuoka M. Xylooligosaccharides for manufacture of dietary fiber
health foods. Int. Patent WO 2,005,092,124; 2005.
[103] Tateyama I, Hashii K, Johno I, Iino T, Hirai K, Suwa Y, et al. Effect of
xylooligosaccharide intake on severe constipation in pregnant women. J
Nutr Sci Vitaminol 2005;51:4458.
[104] Garca-Rodenas CL, Bergonzelli G, Rochat F, Turini ME, CorthesyTheulaz I, Cherbut C. Nutritional infant formula containing fats or
nondigestible oligosaccharides for optimal gut barrier function. Int.
Patent WO 2,004,112,509; 2004.
[105] Beer M, Gibson GR, Smejka C. Lactobacillusoligosaccharide combination for promoting digestive tract health. Int. Patent WO 2,004,089,115;
2004.
[106] De Jong P, Van Laere K. Preparation that contains oligosaccharides and
probiotics. Int. Patent WO 2,000,033,854; 2000.
[107] Ranganathan N. Nutritional compositions comprising probiotics. U.S.
Patent US 2,004,161,422; 2004.
[108] Hayashi N, Sakaki T, Doi K. Carbohydrate-based food having radicalscavenging activity and its manufacture. Japan Patent JP 2,005,021,111;
2005.
[109] Inafuku M, Fujino T, Kashiwagi Y, Ohara S. Antioxidant dietary fiber, its
manufacture, and processed food using it. Japan Patent JP 2,002,204,674;
2002.
[110] Gueux E, Rayssiguier Y, Busserolles J, Mazur A. Use of prebiotics for
preventing or treating oxidative stress. Fr. Patent FR 2,848,783; 2004.
[111] Murbraek BG, Brandsborg E. Lactobacillus strains. Int. Patent WO
2,003,080,813; 2003.
[112] Clayton P, Conn H. Carbohydrate substitute comprising a low-glycemic
index sugar and a flavonoid. Int Patent WO 2,005,006,891; 2005.
[113] Yukawa M, Okuda S, Ozeki K. Production of health food, drug, and
cosmetic from brewing by-products. Japan Patent JP 2,005,263,722; 2005.
[114] Izumi K, Nakagame S, Kido Y, Nakabo Y. Enteral nutrient containing
xylooligosaccharides. Japan Patent JP 2,003,055,231; 2003.
[115] Izumi Y, Kojo A. Long-chain xylooligosaccharide compositions with
intestinal function-improving and hypolipemic activities, and their manufacture. Japan Patent JP 2,003,048,901; 2003.

1923

[116] Izumi K, Ikemizu S, Shizuka F. Antihyperlipidemics containing acidic

xylooligosaccharides. Japan Patent JP 2,004,182,615; 2004.
[117] Ikemizu S, Kojo, A. Hair growth stimulants containing acidic xylooligosaccharides. Japan Patent JP 2,003,183,133; 2003.
[118] Azumi N, Ikemizu S. Topical preparations for atopic dermatitis
containing acidic xylooligosaccharides. Japan Patent JP 2,004,210,
664; 2004.
[119] Azumi N, Ikemizu S. Collagen production promoters containing acidic
xylooligosaccharides. Japan Patent JP 2,004,059,478; 2004.
[120] Obuchi, T, Takahashi T. Moisturizing agents comprising acidic xylooligosaccharides. Japan Patent JP 2,005,187,388; 2005.
[121] Schroeder KR, Holtkoetter O, Schlotmann K, Mendorf N, Hensel A,
Deters A, et al. Cosmetic or pharmaceutical preparations containing
oligo and/or polysaccharides for the treatment of epithelial covering
tissue. Int. Patent WO 2,005,034,900; 2005.
[122] Kokubo I, Ikemizu S. Acidic xylooligosaccharides as topical antiinflammatory agents. Japan Patent JP 2,003,221,339; 2003.
[123] Kokubo I, Ikemizu S. Therapeutic agents for osteoporosis containing
acidic xylooligosaccharides. Japan Patent JP 2,004,182,618; 2004.
[124] Azumi N, Ikemizu S. Hyaluronic acid-formation promoters containing
xylooligosaccharides. Japan Patent JP 2,004,059,480; 2004.
[125] Kokubo I, Ikemizu S. Histamine-release inhibitors containing xylooligosaccharides. Japan Patent JP 2,004,059,481; 2004.
[126] Brouns FJPH, Bornet FRJ, Coudray C, Rayssiguier YG. Indigestible
oligosaccharides and magnesium absorption in humans. Int. Patent WO
2,002,039,835; 2002.
[127] Monsan P, Valet P, Remaud SM, Saulnier BJS. Use of prebiotics for the
prevention of onset of Type II diabetes. Fr. Patent FR 2,844,453; 2004.
[128] Ito M, Yamaguchi K, Izumi K. Xylooligosaccharide compositions, and
cancer cell apoptosis inducers containing them. Japan Patent JP
2,001,086,999; 2001.
[129] Ando H, Ohba H, Sasaki T, Takamine K, Kamino Y, Moriwaki S, et al.
Hot-compressed-water decomposed products from bamboo manifest a
selective cytotoxicity against acute lymphoblastic leukemia cells. Toxicol in vitro 2004;18:76571.
[130] Takahashi T, Ikemizu S. Antiallergy agents containing acidic xylooligosaccharides for alleviation of allergic rhinitis. Japan Patent JP
200,112,826; 2005.
[131] Sugiyama S, Kobayashi H, Matsumoto A. Oral cavity compositions
containing lactic acid bacteria products and gluconates and/or oligosaccharides. Japan Patent JP 2,004,250,374; 2004.
[132] Stahl B, MRabet L, Vos AP, Garssen J, Boehm G. Immunomodulating
oligosaccharides, and therapeutic use thereof. Int. Patent WO
2,005,039,597; 2005.
[133] Maeda H, Ichihashi K, Fujii T, Omura K, Zhu X, Anazawa M, et al. Oral
administration of hydrolyzed rice bran prevents the common cold
syndrome in the elderly based on its immunomodulatory action. BioFactors 2004;21:1857.
[134] Speelmans G, Knol J, Haarman M, Garssen J. Pre- and probiotic
compositions for infants, especially those not breast fed in prevention
and treatment of immune disorders. Int. Patent WO 2,005,039,319;
2005.
[135] Katapodis P, Kintzios S, Konstas J, Kekos D, Macris BJ, Christakopoulos
P. Enzymic production of aldopentauronic acid and use as a bioregulator
in plant airlift bioreactors. J Biosci Bioeng 2003;95:6302.
[136] Smiricky-Tjardes MR, Flickinger EA, Grieshop CM, Bauer LL, Murphy
MR, Fahey Jr GC. In vitro fermentation characteristics of selected oligosaccharides by swine fecal microflora. J Animal Sci 2003;81: 250514.
[137] Stanton C, Gardiner G, Meehan H, Collins K, Fitzgerald G, Lynch PB,
et al. Market potential for probiotics. Am J Clin Nutr 2001;73:476S83S.
[138] Pizzoferrato L. Functional ingredients and functional components. Ingr
Aliment 2003;2:2630.
[139] Taniguchi H. Carbohydrate research and industry in Japan and the
Japanese Society of Applied Glycoscience. Starch 2004;56:15.
[140] Nakakuki T. Present status and future prospects of functional oligosaccharide development in Japan. J Appl Glycosci 2005;52:26771.