INTRODUCTION:
Nature
has always renewed for our pleasure the multicolored splendours of its
adornments, leading us to recognize the richness of the presents offered by
the flora1. In Europe, in the 19th century, the textile industries
acquired huge quantities of easily available dyes. This situation triggered the
invention of synthetic dyes, offering a wide range of new colours at a lower cost,
and giving better properties to dye materials 2. West Africa, where there
is no legal and regulatory framework for the import and use of dyes, is nowadays
a vast market for the disposal of even the most toxic synthetic dyes banned in Europe.
To
this day, synthetic dyes remain the main option chosen to dye textiles, despite
the potential health and environmental risks 3, as some of them would
have carcinogenic and cytotoxic effects. However, in some parts of the world, this
discovery has led to a resurgence in the use of natural-derived dyes to replace,
at least in part, synthetic dyes. Researchers are increasingly interested in natural
dyes because of their biodegradability and higher compatibility. This renewed interest
in plant dyes is also aligned with a global concern for the development of ecological
and sustainable production, including in the textile sector 4.
This
diversity of colors offered by the flora has always oriented the choices for the
practice of tinctorial able to offer ranges of strong shades appreciated by consumers.
The
attachment of the man to the colors, allowed him, according to these preferences,
to undergo enormous transformations, his costumes, clothes and linens.
Natural
dyes for textile use today, through dyeing and its techniques 5, continue
to reveal their secrets and are the subject of extensive research to provide a guarantee
of the health of users and consumers.
The
diversity of these ranges of shades obtained in tinctorial practice derives its
deep understanding in the nature of the organic molecules responsible for the pigments
of plants in their entirety.
The
production of quality cotton fibres and the techniques of processing these fibres
in Burkina Faso is a national priority 6 and this is of paramount importance
for the accompaniment and mastery of techniques of tinctorial practices especially
artisanal.
Knowing
the structures of the molecules responsible for pigmentation and co-pigmentation
at the plant level remains an issue that can justify or promote the improvement
of tinctorial practice protocols 7, 8.
Based
on the content of various groups of chemical compounds and the identification of
major molecules by chromatographic and spectral methods (HPLC-MS and FT-IR), this
work aims to dye cotton threads using A. Leiocarpus leaves extract. Through
the phenomena of co-pigmentation 9 with many other molecules (tannins
10, phenolic acids...) and the use of non-toxic chemical bitings (alum,
iron sulphates and hydrated copper), these flavonoids have contributed to the determination
of various shades of color in dye made on
skeins
of cotton thread.
MATERIALS
AND METHODS:
Extraction
and yield:
250
g of powder obtained from Anogeissus leiocarpus dried leaves, was extracted
using water in a soxhlet 11. Water extraction was justified by the partial
preservation of the current practices of dyeing craftsmen in Burkina Faso. The extract
was concentrated by evaporation and then frozen and dried with ALPHA 1-2 LDplus
brand freeze-dryer.
The yield of the resulting dye powder was assessed by Relationship
1:
Mass of Dye extract
Yield
= -----------------------------------x 100 (1)
Mass of plant material
Total
flavonoids content:
It consisted of adding 60 µL of the extract, 150 µL of
distilled water, 15 µL of a solution of sodium nitrite (NaNO2) to 5 %,
15 L of an aluminum chloride solution (AlCl3) at 10 % and 50 µL of a
soda solution (NaOH) at 1 M. Total flavonoid content was determined by reading the
absorbances at 510 nm using the microplate reader 96-well quartz (MP96 spectrophotometer
SAFAS). Absorbance was related to the standard curve obtained from the quercetin
taken as standard (relationship 2) 12, 13.
(Abs – b) × V ×DF
C (mg
Eq/g) = ------------------------- (2)
m × a
C (mg
EQ/g): Quercetin equivalent milligram content per gram of dye powder.
Abs: Absorbance;
b: Originally ordained; a: slope; V: Volume; DF: Dilution
Factor; m: Dye mass.
Hydrolyzable
and condensed tannins rates:
Hydrolyzable tannins rate:
To
60 µL of the extract, was adding a volume of 220 µL of a mixture of iron chloride
III to 10-2 M and hydrochloric acid to 10-3 M (50 / 50 v/v),
the absorption reading was made at 660 nm using the 96-Well quartz microplate (MP96
spectrophotometer, SAFAS). Absorbance read was related to the formula of relationship
3 14:
A:
Absorbance; ε_mole: 2169 of Gallic acid; MW: Molecular weight of gallic acid;
V: Extract volume used; P: Sample weight; DF: Dilution factor; R (%): Hydrolyzable
tannins.
Condensed tannins rate:
To
90 µL of the extract was added 190 µL of a vanillin solution at 0.01% in concentrated
sulphuric acid. The absorption is read at 500 nm using a 96-well quartz microplate
reader (MP96 spectrophotometer, SAFAS). The rate of condensed tannins is obtained
by reporting the absorption read in the formula of relationship (4) 15, 16.
5,2.10-2
: Constant expressed in cyanidin equivalent;
A: Absorbance; V: Extract volume used; P: Sample weight; R (%): Condensed tannins
rate.
High
Performance Thin Layer Chromatography of dye extract:
The
chromatographic profile of the natural dye was achieved by high performance thin
layer chromatography (HPTLC) 17-19. The principle was to deposit 3 µL
extract with standard in the form of thin bands 8 mm long, on a 20x10 cm F254
HP silica gel plate using a CAMAG Automatic TLC AutoSampler 4 device.
After
a saturation stage for 20 minutes, plaque development was achieved using the mobile
phase acetate of ethyl-formic acid-acetic-water (100:11: 11:26 v/v).
To
observe polyphenols in general and flavonoids in particular, two specific revelators,
successively 2-aminodiphenylborate (1 g in 100 mL of methanol) and polyethylene
glycol (5 g in 100 mL of ethanol at 96 %), were used to spray the plate which is
then heated to 110 °C for 3 minutes.
Analysis
of dye by infra-red to transformed Fourrier (IR-TF):
The
direct use of raw natural dyes is justified in part by the difficulty of isolating
sufficient quantities of dyes for textile dyeing, given the molecular complexity
of mixtures at the level of natural substances. For example, infra-red spectra (IR)
are often recorded on raw extracts to provide a brief erict of the chemical functions
present in the total extracts, which are responsible for observing various final
colour shades of dyed textile material 20, 21. Thus, the total dye extract
containing tannins, flavonoids, xanthonoids and other compounds is subjected to
an infra-Red spectrometry analysis to Fourrier Transformed (IR-TF) type TENSOR 27
for identification of functional groups present in constituents structures.
HPLC-MS
of flavonoids from A. leiocarpus dye extract:
The
dye extract from the A. leiocarpus leaves containing flavonoids, previously
filtered using a syringe (type cellulose acetate membrane 25 mm and 0.45 µm) is
characterized by high-performance liquid chromatography (HPLC) coupled with mass
spectrometry (MS) at the National Laboratory of Public Health (LNSP) in Ouagadougou
(Burkina Faso).
The
ions are controlled in MS/MS in positive ionization mode (ESI). The HPLC separation
is performed on a Zorbax sb C18 column (250 x 4.6 mm; 5 µm) 22, 23, 24.
The
mobile phase consists of two solvents A and B in order to achieve an elity gradient
with a flow rate of 0.6 mL/min. Solvent A is 5% formic water-acid (v/v), solvent
B is made up of 5% formic acetonitrile-acid (v/v). The elion consisted of a 95 %
to 90 % stage of solvent A for 5 minutes and then the gradient was maintained at
90 % of A for 10 minutes. Then 90 % to 88 % A in 10 minutes, to 85 % A in 10 minutes,
82 % A in 15 minutes, to 75 % A in 10 minutes, 70% A in 20 minutes and finally returned
to 95 % A in 10 minutes (the total run was 90 min). The injection volume was 50
µL. The mobile phase was then injected into the electrospray ionization source.
The
data were provided by Agilent Technologies, Inc. 2012 LC/MS Data Acquisition for
6400 Series Triple Quadripole (version B.06.00 Build 6.0.6025.0). The temperature
of the gas (N2) was 200°C, the gas flow of 10 L/min and the pressure
of the nebulizer 15 psis. In the experience, Nebulizer and collision gas was nitrogen.
The mass spectrometer scans all ions with a m/z value between 100 and 1100. Comparison
of retention times and molecular weights of the observed fragments thus allowed
the identification of flavonoid molecules. Indeed, the principle was to inject the
sample in solution at a constant flow of about 0.6 µL/min into a conductive capillary.
A desolvatation gas (N2 sec) with an approximate flow of 500 L/h, surrounds
the capillary and promotes the vaporization of the sample. When the potential of
the capillary is positively charged, the positive ions generated will be analyzed
and vice versa. The ions generated inside the device are drawn to the extraction
cone where they will be fragmented. These fragmentations will continue in the collision
cell during tandem mass spectrometry analyses 25, 26.
This
characterization of flavonoids in ESI-MS/MS was based on generation in the source
of ionization of the aglycone patterns of each flavonoid compound. As a result,
the tandem MS analysis of molecular ions resulted in different fragmented ions specific
to each type of aglycone.
Tinctorial
practice:
Unwinding:
It
consisted of ridding the textile material (Cotton wire swaths) of wax, pectin and
other dirt that could influence the fixation of the dye 27, 28, 29.
Approximately
70 g of skein cotton thread was immersed in 700 mL of water brought almost to a
boil (about 90oC), to which are added 700 mg of neutral soap (SN CITEC
soap or Marseille soap) and 3.5 g of sodium carbonate.
After
1 hour of boiling, 0.7 mL of acetic acid is added to the set for the neutralization
of the base. The skein was then rinsed thoroughly with water and washed with neutral
soap and dried in a room.
Mordancing:
In
natural tinctorial practice, several kinds of biting chemical and plant origins
(tannins) are used. Three types of biting 30, 31, 32 were used: alum
[KAl(SO4)2, 12H2O], hydrated iron sulphate (FeSO4,
7H2O) and hydrated copper sulphate (CuSO4, 5H2O).
140
mg of each type of bite is dissolved in 30 mL of hot distilled water. Then, sodium
hydroxide (14 mg) is added for the revelation of different types of ions and their
colors (Al3+ white, Fe2+ pale green, Cu2+ blue).
A precise
mass of small skeins of yarn (700 mg each) was immersed in each lukewarm mixture
and the whole has been kept for 12 hours.
The
skeins are then removed and strongly wrung out and placed in lockdown in plastic
bags for 72 hours before dyeing.
Dyeing with Anogeissus leiocarpus leaves extract:
At
this stage, two different dye baths (acid and basic) were prepared in acid and basic
baths.
The
principle was to immerse the unst chlorinated and bitten yarn tangles (700 mg each)
in acidic and basic baths of each type of dye.
The
dye rate was set at 4 % and so each bath was obtained by dissolving 28 mg of each
type of dye in 14 mL of distilled water.
Thus,
after adjusting the pH to 4 for the acid bath and 10 for the basic bath using the
mobile pH (826 pH mobile / 827 pH lab, Ω Metrohm), each bath was brought to
a temperature of about 70 °C before immersion of the skeins.
These
skeins were constantly stirred in the bath to facilitate the homogenization of the
dye.
After
45 minutes, the skeins were removed from the bathing area and spread out in the
open air in dirty, and then 10 minutes later they were rinsed thoroughly and spread
out again. Then, 1 hour later, they were washed with soap (Marseille soap) and then
dried permanently in the room 33, 34, 35. Soap washing is one of the
first tests of strength carried out on dyed fibres and fabrics. Other tests such
as light, chlorinated water or sweat tests are corroboration tests of wash test
results.
For
the assessment of the homogeneity of the dye, a magnifying glass (classical-black,
Magnification: 3.5x, 5x 50 mm, 60 mm, 75 mm) was used for careful observation and
this allowed the development of a scale of assessment of the homogeneity of the
fixation, ranging from 1 to 4 (1: non-homogeneous; 2: medium homogeneity; 3: fairly
good homogeneity; 4: very good homogeneity).
RESULTS:
Yield,
Total flavonoids content (TFC), hydrolyzable tannins rate (HTR) et condensed tannins
rate (CTR):
Quantitative
results (Table 1) showed that the A. leiocarpus, with an extraction yield
of 4.94 %, contain total flavonoids content of 458.759 ± 27.773 mgEQ/g of dye powder,
hydrolysable and condensed tannins rates of 13.25 % and 12.96 % respectively.
Table
1: Yield, Total flavonoids Content (TFC), hydrolyzable tannins rate (HTR) et condensed
Tannins rate (CTR) of A. leiocarpus leaves extract
|
Extrait
|
Yield (%)
|
TFC (mg / g)
|
HTR (%)
|
CTR (%)
|
|
A. leiocarpus
|
4.94
|
458.759 ± 27.773
|
13.255 ± 0.011
|
12.965 ± 0.245
|
HPTLC flavonoids profile and IR-TF spectrum:
Chromatographic
profiles, in accordance with other works found in literature, indicated the presence
of flavonol derivatives (quercetin, kaempferol...) 36, 37.
In
addition, a review of infrared spectral data revealed the presence of essential
chemical functional groups characterized by elongation vibrations.
1: A. leiocarpus, 2: Hyperoside (3-O-galactoside
of quercetin);
3: Isorhamnetin 3-O-glucoside; 4: Rutin;
5: Hyperoside (Quercetin 3-O-galactoside); 6:
Kaempferol
Figure 1: HPTLC flavonoids profile of A. leiocarpus
extract at 366 nm
RESULTS OF TINCTORIAL PRACTICE:
Dyeing practice on cotton fibers allowed for various shades of colors based on the protocols described above
DISCUSSION:
Beyond the quantitative aspect (Table 1), the dye extracted from the leaves of A. leiocarpus on the chromatographic (HPTLC) and spectral (IR-TF) level, showed the presence of a subgroup of flavonoids (flavonol) characterized partly by the detection of essential chemical functions in IR-TF (Figures 1 and 2)
Natural
dyes, as used in natural dyeing, are complex mixtures of molecules. Each molecule
has chemical functions that give it particular properties. The most information-rich
and experimentally accessible part is the medium IR (4000 to 400 cm-1).
In this area, absorptions corresponding to wavenumbers less than 800 cm-1
form a kind of fingerprint of compounds which allows to recognize them and those
greater than 800 cm-1 were characteristic of the chemical bonds present
in the sample, allowing functional and structural analysis38. The IR
spectrum of the dye extracts has characteristic bands corresponding to specific
functional groups (Figure 3). Thus, the observed wavenumber at 3206 cm-1
characterizes an elongation vibration νO-H corresponding to the
functional hydroxyle OH bound alcohol group. Other wavenumbers at 1330 cm-1
and 1057 cm-1 corresponding to the νC-O elongation vibration
refers to the presence of functional C-O group in the extract, indicating the functions
of either esters or oxide ethers (Figure 3). According to the literature, A.
leiocarpus (νO-H : 3206 cm-1 ; νC-O :
1330-1057 cm-1) contains flavonoids belonging to the subgroups of flavonols
and flavanols 39, 40.
HPLC
of the total extract of A. leiocarpus leaves presented three (03) essential
peaks in the investigation of flavonoids [1: RT = 42.4 min; 2: RT
= 45.4 min; 3: RT = 56.7 min].
Compounds
1 and 3 are isomers whose molecular ion at m/z [M+H] +
449 u (C21H20O11). MS/MS secondary ions at m/z
303 u and 287 u respectively corresponding to losses of rhamnose [M+H-146]
+ and hexose that may be either glucose or galactose [M+H-162] +
respectively.
The
molecular ion at m/z 479 u (C21H18O13) corresponding
to compound 2, produced in MS/MS a secondary ion at m/z 303 u following to
the loss of glucuronide [M+H-176] +.
The
peaks at m/z 449 u of compound 1 and 3 would be quercetin 3-O-rhamnose
and kaempferol 3-O-hexoside respectively. The peak at m/z 479 of compound 2
would correspond to quercetin 3-O-glucuronide.
These
flavonic compounds in association with many other phenolic compounds (tannins, phenolic
acids...) present in A. leiocarpus leaves extract such as 3,4,'-tri-O-methylflavellagic
acids and its glucosylated derivative (3,4,3'-tri-O-methylflavellagic-4'-β-D-glucose),
leiocarpanes A and B glucuronomannanes, castalagin 41-44 would explain
the different colors obtained in tinctorial practice. These hydroxylated compounds,
beyond the intermolecular association, often pass through chélator metals (Al3+, Fe2+, Cu2+) for the creation of complexes favorable to the fixation
on the monomer unit (D-glucopyranose) of the cellulose of cotton fibers. These complexes
are preferred to the hydroxylated sites 2,3, and 6 of D-glucopyranose 45, 46.
In addition, the affinity of the dye molecules with the cellulosic fiber and their
fixation on the cotton fiber, depends on the acid or basic nature of the dye bath.
The
tinctorial practice has allowed the obtaining of very different shades of color
with a fairly good fixation and a fairly good homogeneity.
Dyeing (Table 3) realized with A. leiocarpus leaves
extract resulted in a range of characteristic shades of color (anise lime, military
anise, grey green anise, chartreuse green...). The quality factor (QF) based on
the product of the degree of fixation by the degree of homogeneity allowed to obtain
significant strong color shades using alum in acidic medium, hydrated iron sulphate
in acid and basic environments and copper sulphate in a basic medium. The fixation
of molecules of the coloring material from A. leiocarpus leaves requires
the intervention of mordants making it a mordanting or metal-bearing dye.
CONCLUSION:
This
study allow to understand that A. leiocarpus leaves contain flavonoids, which,
through intra- or intermolecular associations, contribute to obtain shades of colors
in tinctorial practice.
Total
flavonoids content from A. leiocarpus leaves was about 458.759 mg of EQ/g
of dye powder and total hydrolyzable and condensed tannins rates were respectively,
of 13.255 % and 12.965 %. The natural dye from the dry leaves of A. Leiocarpus,
in a dyeing process with alum, iron and copper sulphates as mordants allow the obtaining
of various shades of colors. These shades would explain the affinity of flavonols
such as kaempferol 3-O-hexoside and quercetin 3-O-glucuronide with the mordants
used (alum, iron sulphates and copper). This affinity therefore justifies the chelation
of these compounds with the metal salts (Al3+,
Fe2+, Cu2+) already
fixed by mordanting on cotton fiber (cellulose) whose monomer unit is D-glucopyranose
where hydroxyl groups in positions 2, 3 and 6 (active sites) allowed chelation.
Dye from the A. leiocarpus leaves, can be classified in groups of natural
mordanting dyes, so-called metal dyes.
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