Exploratory Analysis of Deoxyanthocyanidins With Chemometric Methods

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Exploratory Analysis of Arrabidaea chica Deoxyanthocyanidins Using

Chemometric Methods
Adriana L. Schiozer a; Paulo H. Março a; Lauro E. S. Barata a; Ronei J. Poppi a
a
Instituto de Química, Universidade Estadual de Campinas, C. P, CEP Campinas, SP, Brazil
Online Publication Date: 01 June 2008
To cite this Article Schiozer, Adriana L., Março, Paulo H., Barata, Lauro E. S. and Poppi, Ronei J.(2008)'Exploratory Analysis of
Arrabidaea chica Deoxyanthocyanidins Using Chemometric Methods',Analytical Letters,41:9,1592 — 1602
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Analytical Letters, 41: 1592–1602, 2008
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DOI: 10.1080/00032710802122198
CHEMOMETRICS
Exploratory Analysis of Arrabidaea chica

Deoxyanthocyanidins Using Chemometric
Downloaded By: [UNICAMP Universidade est Campinas] At: 19:11 28 August 2008
Methods
Adriana L. Schiozer, Paulo H. Março,

Lauro E. S. Barata, and Ronei J. Poppi
Instituto de Quı́mica, Universidade Estadual de Campinas,
C. P., CEP Campinas, SP, Brazil
Abstract: A pure, isolated deoxyanthocyanidin, carajurin, and ethanol leaf

extract of Arrabidaea chica were dissolved in solutions having five different pH
values and submitted to Ultraviolet (UV) radiation and left in the dark for 24
hours. A principal component analysis was used to predict the number of species
present in each solution, and ultraviolet spectra were recovered by Multivariate
Curve Resolution (MCR). Solutions containing deoxyanthocyanidins present
quite stable profiles in general, as compared to common anthocyanidins, which
might recommend deoxyanthocyanidins and extracts rich in these compounds
as potential alternative natural pigments for food and cosmetics.
Keywords: Chemometrics, degradation, deoxyanthocyanidins, MCR
INTRODUCTION
Natural pigments approved by the United States Food and Drug Admin-
istration (USFDA) are limited due to their instability, low coloring
power, and restricted color spectrum. For this reason, several studies
have been conducted to improve the stability of natural pigments. Some
Received 11 October 2007; accepted 31 January 2008.

Address correspondence to Adriana L. Schiozer, Instituto de Quı́mica,
Universidade Estadual de Campinas, C. P. 6154, CEP 13083-970, Campinas,
SP, Brazil. E-mail: schiozer@iqm.unicamp.br
1592
MCR Analysis of Deoxyanthocyanidins 1593
natural pigments in vivo are more stable than the isolated substances.
While synthetic chemists have encountered difficulties in the synthesis
of stable molecules, plants seem to have developed other strategies for
protecting color (Wissgot and Bortlik 1996).
Anthocyanins are unstable flavonoids found in several plants,
responsible for bright colors that in general vary from red to blue as a
function of pH (Francis 1982). Their color stability is strongly affected
by pH, solvents, temperature, concentration, and molecular structure,
as well as exposure to oxygen, light, enzymes, and co-pigments.
Anthocyanins have been used in some commercial products but, due to

their color variation at different pH values and constraints on stability,
there is a preference for their use in acidic products. The ionic nature
of anthocyanins favors a change in molecular structure as a function of
pH, resulting in different colors for different pH values (Brouillard
1982; Terci and Rossi 2002). This is also true for deoxyanthocyanidins.
The 3-deoxyanthocyanidins are quite uncommon substances found
in nature and are not frequently reported in the literature. These rare
substances differ from the known anthocyanidins beacuse they lack a
hydroxyl group in the C-3 position. This difference also leads to higher
stability, although this stability is seldom discussed in the literature. They
are also found in nature as aglycones. Deoxyanthocyanidins are probably
the ancestors of anthocyanins, because they are found in mosses and
ferns, the most primitive land plants. They are the colored substances
most commonly found in the leaves of A. chica and are responsible for
the red pigmentation of the leaves. Besides carajurin (6,7-dihydroxy-
5,40 dimethoxyflavylium), there are two other deoxyanthocyanidins that
were also found in the plant (Devia et al. 2002).
A. chica Verlot (Bignoniaceae) is known by the common names of
carajiru, crajiru, pariri, and chica. It is found in Central and South
America, mainly in the Amazon region. The leaves are used in traditional
medicine to treat some diseases. Recently the antimicrobial activity of
leaf extracts was confirmed (Barata et al. 2006).
It is well established that anthocyanins, anthocyanidins, deoxyantho-
cyanidins, and synthetic flavylium salts are involved in a common array
of reactions that follow a general pattern (Melo et al. 2002). These com-
pounds all have a common 2-phenyl-benzo-pyrilium core. Scheme 1
shows conceivable structural transformations of the carajurin ion in an
acidic medium. According to Scheme 1, several species can be involved
in this complex set of equilibria: Flavylium cation (AHþ ) is the predomi-
nant species at low pH ( < 2), and it easily deprotonates to form the
quinoidal base (A) or the colorless pseudobase or carbinol (B). The car-
binol form does not absorb light and is in tautomeric equilibrium with
cis-chalcone (Cc), which also isomerizes to trans-chalcone (Ct) via a
1594 A. L. Schiozer et al.
Scheme 1. Structural transformation of carajurin ion.
cis-trans isomerization reaction (Brouillard 1982). Color intensity

increases for basic media. Nevertheless, the color and maximum wave-
length (kmax) are different when compared in solution at pH < 2 (Rein
and Heinonen 2004). There appears to be no information in the literature
on the deoxyanthocyanidins’ pure spectra along the pH range 1–12, and
no study has been found on whether deoxyanthocyanidins undergo the
transformations shown in Scheme 1, which are analogous to those
proposed for anthocyanins.
The hydration and isomerization equilibria found for these
substances can be caused by irradiation or by pH change, and the
combination of these two equilibria permits formation of a variety of
species, making these compounds very interesting model systems (Melo
et al. 2002).
Most of the studies on anthocyanins use the pH-jump method to
calculate the equilibrium constants (Brouillard 1882). Unfortunately, in
most cases, the total number of species that contribute to the spectrum
is usually unknown. To minimize this problem, chemometric methods
are being employed to estimate the number of species present in a
nonpurified system.
With the growth of chemometrics in recent years, a general approach
involving the identification of a model from numerical and statistical
analysis of data has been proposed to solve the mixture analysis problem,
without any previous assumption about the nature or composition of
the system under investigation. Mixture analysis implies the estimation
of the number of chemical species simultaneously present in the mixture,
the identification of these species, and the determination of their concen-
tration. Among the computational and statistical methods used to solve
mixture analysis problems, Factor Analysis (FA), Principal Component
Analysis (PCA), and Singular Value Decomposition (SVD) techniques
play a key role, especially in the estimation of the number of species

contributing significantly to the experimental data variance (Mendieta
et al. 1998). These pure mathematical solutions obtained with FA-derived
methods can be transformed to physically meaningful solutions by
Multivariate Curve Resolution (MCR) methods (Tauler 1995).
The objective of this work is to investigate the kinetic behavior of the
deoxyanthocyanidin carajurin isolated from A. chica, and a crude
ethanol leaf extract after decomposition by Ultraviolet (UV) radiation
at different pH values over 24 hours, using chemometric methods. The
crude extract is a mixture of several substances, including deoxyantho-

cyanidins, other flavonoids, co-pigments, and free sugars. Our aim is to
find if these other substances can affect the stability of the deoxyantho-
cyanidins. The results obtained from this work may constitute the basis
for the development of an analytical methodology for determining the
number of species involved and for a first elucidation of the mechanism
of the deoxyanthocyanidin degradation kinetics.
METHODOLOGY
Principal Component Analysis
Principal Component Analysis (PCA) is a multivariate statistical

technique used for reducing the dimensionality of a dataset. It is based
upon Eigen-analysis of the correlation or covariance matrix. Literature
on PCA is abundant, and this section will provide only a summary.
The data matrix A consists of objects (spectra) represented by p
variables (absorbances at different wavelengths). The PCA decomposes
matrix A into a product of two matrices,
A ¼ Tnq Ptqp þ Enp ; ð1Þ
where T is a scores matrix, P is a loadings matrix, and E is a matrix of

residuals. The number of factors describing the major part of the data
variance is represented by q, and Pt is the transpose of P. Each factor
corresponds to a row or column of the T and P matrices, respectively
(Beebe et al. 1998).
Multivariate Curve Resolution
All resolution methods mathematically decompose a global mixed

instrumental response into pure contributions due to each component
in the system. This global response is organized into a matrix D contain-
ing raw information about all components. Resolution methods allow for
the decomposition of matrix D into the product of two matrices, C and
ST, each of them including the pure response profiles of the n mixture
or process components associated with the row and the column direction
of the initial data matrix, respectively. In matrix notation, the expression
valid for all resolution methods is
D ¼ CST þ E; ð2Þ
where D(r c) is the original data matrix, C (r n) and ST(n c) are the
matrices containing the pure response profiles related to the data

variation in the row direction and in the column direction, respectively,
and E (r c) is the error matrix, i.e., the residual variation of the dataset
that is not related to any chemical contribution. Parameters r and c are
the number of rows and the number of columns of the original data
matrix, respectively, n is the number of chemical components in the
mixture or process, and C and ST often refer to concentration profiles
and spectra (hence their symbols), although resolution methods are
proven to work in many other problems (Juan and Tauler 2003).
MCR is included in the FA family of techniques. The main goals are
the isolation, resolution, and quantification of the sources of variation in
a particular dataset. The outstanding feature of this technique is that no a
priori assumption about the contribution of the different factors to the
global response is necessary (Mendieta et al. 1998). Here, MCR was used
on the MatLab1 program implemented with tools available from Romà
Tauler Ferré and Anna de Juan webpage (Tauler webpage, 2007).
EXPERIMENTAL
Plant Material
A. chica was collected in Maring

a city, Parana state, Brazil. A voucher
was deposited at the herbarium of the State University of Campinas-
Unicamp, access number UEC 145.956.
Ethanol Crude Extract Preparation and Carajurin Isolation
Ethanol crude extract was obtained by extracting crushed dried leaves of

A. chica with 30% ethanol and continuous stirring for one hour at room
temperature. Paper filtration resulted in a solution that was partially
evaporated and then freeze-dried.
The leaves were extracted with water (20C) for glycosides

elimination. After filtration and complete evaporation of any residual
water, the leaves were extracted three times with hexane followed by
dichloromethane under stirring at room temperature. The dichloro-
methane extract was evaporated and pretreated in C-18 cartridges,
leading to carajurin, identified using HPLC-DAD and ESI( þ )-MS=
(m=z majority ion of 299 and fragment ions of 284 and 269) (Devia
et al. 2002).
Description of Stability Experiments
The analyses were carried out with a UV-Vis spectrophotometer (Agilent

Mod. 8453–diode array) with a quartz cuvette (d ¼ 1cm). The tempera-
ture was fixed at 25C (0.1) at constant stirring. Ultraviolet absorption
spectra at different pH values were obtained from 190 to 1100 nm. The
dried ethanol crude extract and carajurin were primarily dissolved in
analytical grade ethanol and further diluted in buffer solutions of pH
1, 4, 7, 10, and 12 (1:1 v=v), at a concentration suitable for an absorbance
around 0.8 at kmax in the visible band. Solution preparation was always
carried out right before the start of each stability analysis. The samples
were analyzed with and without UV radiation for 24 hours. Buffer
solutions were prepared with analytical grade reagents at five different
pH values according to Morita and Assumpção (1981).
RESULTS AND DISCUSSION
Figure 1 shows the carajurin experimental spectra obtained by applying

MCR to the data corresponding to different pH values. From the
kinetic profiles obtained at pH 1, it can be seen that it is a stable
species related to flavylium cation structure (Terci and Rossi 2002).
After 24 hours of exposure to UV light, a small degradation can be
observed from a decrease in the absorbance at 471 nm, a flavylium
cation region, and an increase of the absorbance at 291 nm, the charac-
teristic region for carbinol base (Março and Scarminio 2007). A PCA
for this medium shows that two factors explain 99.99% of the total
data variance, whereas only one factor is used to explain the variance
of the data referred to the sample left in the dark, when a negligible
degradation was verified during the 24 hours. At pH 4, PCA requires
two factors to explain 99.97% of the data variance. From the
observation of the spectra recovered by MCR, it is evident that light
absorption leads to a degradation of the colored substance, as can
be seen from a decrease in absorption at 487 nm (Fig. 1). Changes in
Figure 1. Carajurin recovered spectra at different pH values with and without UV

radiation. Each spectrum below (dotted and full line) represents substance(s)
predicted by the chemiometric analysis.
the maximum wavelength band from 295 to 281 as well as a change in

the absorbance at this wavelength band are also observed. These results
lead to the conclusion that the substances present at pH 4 are the
flavylium cation, which turns into another substance—probably the
carbinol base, in accordance with its kmax in the UV region band. At
the same pH, the sample kept in the dark showed a smaller absorption
change, and two PCA factors explain 99.99% of the variance. As sta-
ted by Março et al. (2005), anthocyanin solutions are a mixture of dif-
ferent structural entities, so it is quite impossible to obtain the pure
spectrum of each species, and the absorption spectrum of the trans

and cis-chalcone isomers are practically identical. Despite the fact that
the MCR model was able to separate the absorption bands, these spec-
tra show no evidence of the presence of each intermediate species.
Melo et al. (2002) pointed out that the conversion of AHþ into A
and then A into B and Cc are in seconds’ timescale, and the formation
of Ct is slower, but this latter substance represents a more stable form.
At pH 7, and similarly at pH 12, PCA showed that after 24 hours
under UV light, one factor explains more than 99.95% of the total
variance. MCR results show spectra with the strongest absorption at
293 nm for pH 7 and 278 nm for pH 12, but there is still substantial
absorption in the visible region, at 484 nm. At pH 10, a strong trans-
formation was observed in the spectra obtained by MCR, with two
factors explaining 100% of the data variance, starting from band
absorbances of 276, 306, and 485 nm and switching to 276 and
380 nm, which suggests the formation of ionized cis and=or trans-
chalcone (Levi et al. 2004). According to Melo et al. (2002), negatively
charged trans-chalcones are dominant in basic conditions. Close to
276 nm, the peak absorption can be correlated to the carbinol base
structure. In this case, two factors explain 99.93% of total data
variance, and three factors explain 100%. For the same sample submit-
ted to degradation in the dark, only two species are present in the
equilibrium, because two factors explain 100% of data variance.
In contrast to what is observed for anthocyanins, carajurin does not
seem to present species A, B, and AHþ at the same time in acidic
medium. In other words, not enough changes in spectra profiles were
noticed throughout the degradation experiment to indicate different
structures.
It is important to notice that the carajurin spectral behavior, analyzed
through MCR recovered profiles, is quite different from that of extracts
containing anthocyanins, in general (Levi et al. 2004), except at acidic
media, where both present strong absorbances at the characteristic region
for flavylium structure at pH 1, and they continue to present such charac-
teristics in acidic medium with lower intensity. It is quite peculiar, from the
observation of spectra obtained from the MCR model, that carajurin at

pH 7 and 12 still presents such a characteristic profile. Carajurin presented
highest stability in the pH range analyzed, whereas with anthocyanins the
profile changes dramatically depending of the pH value. Another differ-
ence between the deoxyanthocyanidins and anthocyanins is the stability
under UV light exposure. Pure anthocyanins fade completely in minutes,
whereas deoxyanthocyanidins colors remain for hours.
The spectra recovered by MCR for the data of the ethanolic extract
of A. chica for five different pH values present a small variation after 24
hours of analysis, under UV irradiation and in the dark. The spectra

show the strongest absorbance in the 240–340 nm region when
compared to the 400–550 nm region, suggesting that there are other
colorless substances present in the extract. The small variation in
spectra absorbance confirms that co-pigmentation reactions take place,
and colored molecules react with other plant compounds through inter-
or intramolecular mechanisms, resulting in better color stability.
This explains why fruit juices are much more stable than the colored
isolated substances (Brouillard 1983; Rein and Heinonen 2004). Co-
pigmentation reactions increase color intensity as the result of a bath-
ochromic or hyperchromic shift, and this happens mainly in acidic
media. From the PCA, it can be concluded that, for the five analyzed
pH values, only one and at most two factors explain at least 99.99%
of the data variance. These results lead to the conclusion that the
ethanol extract is quite stable and that the species almost do not vary
within 24 hours, either in the dark or under UV irradiation. No bath-
ochromic shift was observed in any experiment, as was evidenced for
the anthocyanin-rich ethanol extract (Março and Scarminio 2007). This
leads to the conclusion that other substances, probably co-pigments, are
contributing to the stability of the extract.
CONCLUSIONS
The MCR recovered spectra for the ethanol extract and the pure
deoxyanthocyanidin, carajurin, showed small variations during the 24
hours of degradation in the dark or under UV light. Using PCA for
the most stable pH values (1, 7, and 12), only one, at most two,
components (in the case of pH 1 under light exposure), explained at
least 99.95% of data variance. Although it is at pH 1 that the absor-
bance in the visible spectra presented the highest absorbance compared
to other bands, at pH values of 4 and 10, two and three factors were
required, respectively, to explain total data variance. In contrast to
what happens with anthocyanins, for carajurin not enough changes in
spectra profiles were noticed in the degradation experiments to indicate

many different structures.
Experiments with the crude extract showed even better stability. The
small absorbance variation confirms that co-pigmentation reactions take
place (Rein and Heinonen 2004), and colored molecules react with other
plant compounds through inter- or intramolecular mechanisms, resulting
in more stable colors.
This study shows a potential for deoxyanthocyanidins to be used,
either isolated or in extracts, as a natural pigment for food and cosmetics,
due to their higher stability at some pH values.
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This article was downloaded by: [UNICAMP Universidade est Campinas]

On: 28 August 2008

Exploratory Analysis of Arrabidaea chica Deoxyanthocyanidins Using

Online Publication Date: 01 June 2008

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Exploratory Analysis of Arrabidaea chica

Adriana L. Schiozer, Paulo H. Março,

Abstract: A pure, isolated deoxyanthocyanidin, carajurin, and ethanol leaf

Keywords: Chemometrics, degradation, deoxyanthocyanidins, MCR

Received 11 October 2007; accepted 31 January 2008.

Anthocyanins have been used in some commercial products but, due to

Scheme 1. Structural transformation of carajurin ion.

cis-trans isomerization reaction (Brouillard 1982). Color intensity

play a key role, especially in the estimation of the number of species

crude extract is a mixture of several substances, including deoxyantho-

Principal Component Analysis

Principal Component Analysis (PCA) is a multivariate statistical

where T is a scores matrix, P is a loadings matrix, and E is a matrix of

Multivariate Curve Resolution

All resolution methods mathematically decompose a global mixed

matrices containing the pure response profiles related to the data

A. chica was collected in Maring

Ethanol Crude Extract Preparation and Carajurin Isolation

Ethanol crude extract was obtained by extracting crushed dried leaves of

The leaves were extracted with water (20C) for glycosides

Description of Stability Experiments

The analyses were carried out with a UV-Vis spectrophotometer (Agilent

RESULTS AND DISCUSSION

Figure 1 shows the carajurin experimental spectra obtained by applying

Figure 1. Carajurin recovered spectra at different pH values with and without UV

the maximum wavelength band from 295 to 281 as well as a change in

spectrum of each species, and the absorption spectrum of the trans

observation of spectra obtained from the MCR model, that carajurin at

hours of analysis, under UV irradiation and in the dark. The spectra

spectra profiles were noticed in the degradation experiments to indicate

due to their higher stability at some pH values.

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A. chica was collected in Maring