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A REVIEW ON TOXICOLOGICAL STUDY AND DEGRADATION APPROACH OF

XANTHENE DYES

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GIS SCIENCE JOURNAL ISSN NO : 1869-9391

A REVIEW ON TOXICOLOGICAL STUDY AND DEGRADATION

APPROACH OF XANTHENE DYES

Priya Vithalani1 and Nikhil Bhatt 1*

1Department of biogas research and microbiology, Gujarat Vidyapith, Sadra, Gandhinagar,

Gujarat, India

Abstract

Dyes and dyestuff have wide application in all industries. After the increment in industries,
the production of dyes is increase worldwide and waste of this industry causing soil and
water pollution. Around 10000 different dyes are utilised in various industries. Dyes are
having less biodegradability and high toxicity. In classification of dyes, xanthene dye is
creating major issues in environment as it is toxic for all lifeforms. It has fluorescent nature,
carcinogenic and mutagenic properties. So, removal of xanthene dyes from wastewater is
major task. Many physicochemical methods are reported for removal of xanthene dye.
Research work are remaining for biological techniques. Usage of biological method for
removal is difficult as it is causing toxic effect. The removal of xanthene dye by biological
method having eco-friendly, high sustainability and beneficial to environment.

Keywords: Xanthene dye, toxicity, carcinogenic, treatment strategies

1. Introduction

Fresh water plays major role in daily life but after the raised industrialization the scarcity of
water is major issue for environment. As large amount of water is use in various industries
for production of various synthetic compounds. Due to increment in synthetic organic
compounds (SOC’s) production, in ecosystem availability of these compounds increase,
which creates water pollution (Kumar et al., 2019). Majorly all dyes are classified in
synthetic organic compounds. Synthetic organic compounds are generally known as
micropollutants and have toxic properties (Tian et al., 2020). Production of synthetic dyes is
started with first synthetic dye “mauveine” by William Perkin. During 20th century
production of dyestuff is initiated in Europe. Mostly in synthetic compounds classification
dyes plays major role. Dyes are generally water soluble can be use in various application
purposes, among them cosmetic industry is utilising high amount of dyes, which are having
many toxic compounds. So, removal of this compounds before discharge is one of the major
tasks. Direct exposure to environment causes serious issue in environment and ecosystem.

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SOC’s shows different effects on humans such as endocrine disturbance, reproductive,

nervous, cardiovascular system etc. These compounds have high stability and resistant to
degradation, so it needs to be treated. (Arslan et al., 2017) Their removal from environment
is one of the major issue and concerned topic for government, NGO’s and scientists (Alharbi
et al., 2018).

1.1 Xanthene dyes

In synthetic organic compounds, largest area cover by synthetic organic dyes. The general
classification of dyes is described in Figure 1. Among all groups of dyes, one of largest group
is xanthene dyes derivatives which are widely use in synthetic materials. Majorly xanthene
dyes are use in cosmetic, printing and food industry since so far. Xanthene dyes is having
xanthylium or dibenzopyran nucleus as chromophore with amino and hydroxyl group as
auxochromes. Xanthene dyes classified in majorly two groups. One is diphenylmethane
derivatives and triphenylmethane derivatives (Wight, 2000).

1.1.1 Structure and synthesis of xanthene derivatives

In structure of xanthene dye planner heterocyclic skeleton containg “O” known as xanthene.
The structure of xanthene is given in Figure 1 (Chaudhary and Violet, 2020). Synthesis of
xanthene dyes was carried out by nucleophilic compound meta phenol and electrophilic
carbonyl compound in presence of strong catalyst. Diphenylmethane derivatives are
synthesised by condensation of dialkylamino phenols and formaldehyde. These derivatives
are known as pyronins. Triphenylmethane derivatives are fused with phthalic anhydride and
dialkylamino phenols also known as rhodamines. (Wright and Staff, 2014)

Figure 1 Structure of xanthene (Wright and Staff, 2014)

1.1.2. Properties of xanthene derivatives

Properties of xanthene dye is conferring to structure and nature of dye. The nature of
xanthene dye is fluorescent, absorb the light at shorter wavelength but emits the light at
longer wavelength. Based on end group and type of substituents the absorbance spectra of

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xanthene dyes vary between 480-580 nm. Except Rhodamine 6G, all xanthene dyes show
optical properties. In alkaline condition, pyronins are oxidized by oxygen so chemically less
stable than rhodamines. The chemical interaction of rhodamines is depending on pH of
solution. In acidic pH the carboxylic group is protonated and in alkaline condition it is
dissociates. Due to this reason, main absorbance band and fluorescence are shifted toward
shorter wavelength (Drexhage, 1976).

1.1.3. Application of xanthene derivatives

The nature of xanthene dyes is fluorescent, so major application is reported in all cosmetic
products. This dye is used in food industry as well as painting industry also. In research area
these dyes are used in specially cell biology experiment for fluorescence. These dyes are
used in visualisation of biological processes in living cell. Xanthene dyes have their wide
application in biosensors (Derayea and Nagy, 2018).

2. Characteristics of xanthene dye

2.1 Phototoxic reaction

Absorbance of solar light through xanthene dyes participated in chemical reaction which
generates major toxic compounds such as free radicals, which affect the cellular processes
under the influence of visible light. Xanthene dye are absorbing the photon in singlet state,
after getting energy, excited into higher energy level. Molecules having in triplet state
participate in photooxidation and photoreduction reaction. Xanthene dye needs visible light
for activation and can be activated by artificial light or sunlight. In environment, if plants,
animals and humans are exposed to xanthene compounds, it would activated by visible light
and participate in chemical reaction and produce toxic intermediate which are harmful for
living organisms (Larson and Berenbaum, 1988). Xanthene compounds are work as
photosensitizer in presence of light generates free radicals which leads to cell lethality
(Morikawa et al., 1976). Specially from light reaction superoxide anions generated, which
are inhibiting drug metabolising enzymes. It may possible that xanthene dyes are react with
protein present in skin and lead to damage (Furumiya and Mizutani, 2008).

2.2 Carcinogenicity and mutagenicity

Carcinogenicity of xanthene compound first demonstrated with sarcoma production from

Rhodamine B subcutaneous injections in 1952 case study (Umeda, 1956). Rhodamine shows
higher fragments in anaphase and telophase of the broad bean Vicia faba (Lakdawalla and

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Netrawali, 1988). In primary screening test of Salmonella, Rhodamine B and 6G both induce
mutations (Brown et al., 1979).

3 Toxicity of xanthene dye

The dyes belonging from xanthene class are having toxic, carcinogenic as well as mutagenic
characteristics. Toxicity of xanthene dyes are described in aquatic animals, plants and insects.
Humans are also susceptible for toxicity. The detail mechanism of toxicity in described in
Figure 4.

3.1 Toxic effect on animals

Various series of xanthene dyes are studied for toxicity in adult face fly Musca autumnalis
and house fly. Results showed that mortality rate increase as concentration of dye in diet
increase. The dyes causing toxic reaction in absence of light in face fly and house fly. High
toxicity of Rhodamine B was observed in face fly in absence of light (Fondren & Heitz,
1978). Another study regarding mechanism of toxicity of xanthene dye was carried out in
larva of Artemia salina. Lactate dehydrogenase activity was completely inhibited by rose
bengal and phloxin. The death rate of Artemia salina after 24 h was 100 % with concentration
of dye 10-3 M (Kobayashi et al., 1977). Toxic effect of xanthene dye was checked on larva of
culex pipiens under laboratory condition. The results shown that mortality rate was increase
with increment in exposure. Different concentration of xanthene dye induce morphological
changes and aberration at larval stage (Shourbagy et al., 2018). The toxic damage of phloxine
B was evaluated on light brown apple moth Epiphyas postvittana and green headed leaf
froller planototrix excessana using laboratory assays. The mortality of this insects found upto
80-90 % in 0.2- 1 % of phloxine B (McNeill and Goldson, 2001).

3.2 Toxic effect on plants

Ecotoxicity of Erythrosine B on dicotyledons plant garden cress (Lepidium sativum L.) were
studied. After the 72-h exposure the length of root reduced upto 50 % than control. Seed
germination also affected with exposure of dye (Apostol et al., 2015). Photodynamic damage
of rose bengal on plant tissue was checked. Treated leaf disc with sensitizer and 1 mM rose
bengal for 24 h resulted in complete loss of chlorophyll pigment when exposed to light. In
dark the loss of chlorophyll was not found (Knox and Dodge, 1984).

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3.3 Toxic effect on human

Effect of phloxin, erythrosine and rose bengal on major class-I drug metabolising enzyme and
P- Glycoprotein major enzyme and transporter were studied. The results showed that
inhibition of Human cytochrome P-450 3A4 and p-glycoprotein was inhibited due to
exposure of dyes (Furumiya and Mizutani, 2008). Erythrosine B was inhibitor for enzymes
and protein-protein interactions and toxic to pituitary and spermatogenesis process. The
genotoxicity of this dye was investigated by using cytokinesis block micronucleus cytome
assay in HepG2 cells. Total seven concentration of erythrosine B (0.1-70 µg/mL) was
selected from that toxicity showed at two higher concentration and other six concentration
also showed mutagenicity (Chequer et al., 2012). Erythrosine b is promiscuous inhibitor for
tumour necrosis factor (TNF) family and inhibiting CD40 and CD154 protein-protein
interactions. Erythrosine B also affecting cellular cytotoxic effects around concentration of
dye (Ganesan et al., 2011). Figure 2 representing the adverse effect of Rhodamine B when
exposing to sunlight (Vithalani et al., 2022).

Figure 2 Mechanism and effect of toxicity

4. Degradation of xanthene dye

As described above the xanthene dyestuff are highly toxic to ecosystem. Direct exposure of
this compounds is creating major toxic effect in aquatic animals, plants, insects and humans

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as well. In worldwide 10 – 15 % dyestuff are release as waste products. The compounds

having colour, turbidity, bad fragrance and susceptible for growth of pathogens which all
over affecting environmental ecosystem. The removal of this compounds from waste is
mandatory. The degradation of this compounds is very difficult due to their structure and
persistent nature (Dahiya and Nigam, 2020). Many physicochemical methods are utilised for
the removal of xanthene dye. Now a day’s metal containing nanoparticles and combination is
utilised for removal of dyestuff.

4.1 Physicochemical degradation

4.1.1 Adsorption

Adsorption is physical process on which molecule are adhere to surface of other molecule by
the Van der waals attraction force. The process carried out physically, chemically and
biologically. In ancient time carbon was utilized as an adsorbent for water purification. Now
a days this process adapted by different industry to remove a toxic compound (Natarajan et
al., 2018). The toxic dye Rhodamine B was removed by using agricultural waste-based
adsorbent material and got maximum adsorption 1265 mg/g in mangosteen skin activated
carbon (Imam and Babamale, 2020). Biosorption of Erythrosine B were studied using fungus
biomass of Rhizopus arrhizus and maximum adsorption was found 355.9 mg/g and 363.6
mg/g in waste and acid treated waste biomass based on Langmuir adsorption isotherm (Salvi
2018).

4.1.2 Electrochemical Processes

Electrochemical technology has application in removal of toxic contaminants from

wastewater. Modification in electrochemical processes were also studied for removal of toxic
dyes from wastewater. Electrochemical process for the removal of Rhodamine B was
performed and complete degradation of Rhodamine obtained after 35 min, concentration of
electrolyte 0.05 M, pH 7.0 and current density 10 mA/cm2 (Vijayakumar et al., 2019). In
another study graphite based electron fenton are utilised for the removal of toxic xanthene
dye Rhodamine B and 99 % of rhodamine removal was obtained in 180 min of electrolysis
process (Nidheesh and Gandhimathi, 2014). Similarly, treatment of synthetic wastewater
containing Rhodamine 6G was carried out with electrochemical technology and results
obtained complete decolourization was found with in 5 min and 42 % dye was mineralised
with this technique (Zheng et al., 2012). Electrochemical oxidation of rhodamine 6G were

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performed using platinum and Boron dropped diamond and mineralisation efficiency 99 %
was obtained with both anodes. (Khalfaoui et al., 2012).

4.1.3 Nanoparticle Mediated removal of Xanthene dye

The size of nanoparticle is very low so having larger surface area for chemical reactions.
Nanoparticles are utilised for water purification techniques. Now a days, nanoparticles are
utilised for the treatment of wastewater. Nanoparticles are playing major role in removal of
synthetic dyes (Marimuthu et al., 2020). The details of nanoparticle study are given in Table
1. In recent trend combination of two to three nanoparticles combined with other complex are
chemically synthesised for the removal of toxic dyes. The details of nanocomposite mediated
removal are given in Table 2.

Table 1 Nanoparticle mediated removal of xanthene dye

Name of Dye Nanoparticles References

Rhodamine B Palladium reduced graphite oxide Bhat et al., (2020)

composite

Methylene Blue, Titanium oxide You et al., (2020)

Rhodamine B,
Bromocresol green

Rhodamine B Iron oxide, combination of titanium Muraro et al., (2020)

oxide and sliver oxide

Rhodamine B L- Asparagine stabilised gold Garg et al., (2020)

nanoparticles
Methyl Orange

Acid Red 27

Xylenol Orange

Rhodamine B, Combination of Sliver Halide and Phongarthit et al., (2020)

Zinc Oxide
Reactive Orange

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Bisphenol A

Xanthene Dye Sliver nanoparticles stabilised on Kahangi et al., (2020)

hybrid of sepiolite and chitin

Xanthene based on Photo assisted Sliver nanoparticles Wang et al., (2020)

fluorescent dye

Methyl Orange and Sliver and Dandelion catalyst Lai et al., (2019)
Rhodamine B

Rhodamine B L- cysteine capped Zinc Oxide Selvin et al., (2017)

Rhodamine B Zinc oxide Seo and Shin, (2015)

Table 2 Nanocomposite based degradation

Name of dye Composite References

Methylene Blue Magnetic polymer composite Wang et al., (2021)

(Fe3O4@PS@Ag)
Rhodamine B

Rhodamine B Bi2WO6 loaded biochar composite Wang et al., (2020)

Rhodamine B Strontium ferrite/ graphite carbon Bo et al., (2019)

nitride composite

Rhodamine – 6G Bio nanocomposite of zirconium Bhatt et al., (2019)

phosphate
Reactive blue 21

Reactive red 141

Rhodamine B Activated carbon and Titanium dioxide Tian et al., (2015)

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Rhodamine B Sn0.215In0.38S/reduced graphene oxide Wu et al., (2018)

(SIS/RGO)

Rhodamine B, Polyaniline bismuth selenide composite Chatterjee et al., (2019)

Methyl orange,
Malachite green

Rhodamine B Bismuth vanadate reduced graphene Zhang et al., (2018)

oxide
Malachite Green

Rhodamine B TiO2 Polydimethylsiloxane Hickman et al., (2018)

Rhodamine B Graphene- TiO2 nanocomposite Posa et al., (2016)

4.2 Biological system for removal of xanthene dye

In area of current research via biological system is utilised for removal of toxic dyes. In
biological, especially microorganism is in demand because of easily manageable, creating
less toxic waste, environmental friendly etc. Many previous studies were performed with
removal of different textile dye. In the classification Azo, nitroso, reactive, acidic, basic dye
there which creating environment issue. Remediation of this dyes was carried out since
decades many review are also written in treatment of textile effluent (Srivatsav et al., 2019).
Due to industrialisation, Cosmetic, food and paint industry are playing extensive role. The
wastewater of this industry is having highly toxic xenobiotic compound one of the major
compounds is xanthene dye. The removal of this dye by biological means since not carried
out as it is toxic to microorganisms. Thus, very less research work was carried out by of
microorganisms due to its toxicity.

Removal of Rhodamine B was performed by Agaricus brasiliensis white rot fungus (WRF).
The WRF was showed 42 % decolourization on agar plate and 93 % decolourisation in solid
state fermentation with solid bleached sulfate and polyethylene terephthalate. Packed bed

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reactor study was performed for 51 days for decolourization. Maximum laccase activity was
found at 20 days (190 IU/L) and 45 days (203 IU/L) (Hermann et al., 2020). Another
decolourisation of Rhodamine B was performed by using partially purified laccase from
Lentinus polychrous. The results showed 90 % of removal of Rhodamine B after 52 h with 10
µM concentration of dye (Lév et al., 2010). Decolourisation and degradation of xanthene dye
fluorescein was carried out by Coriolus Versicolor white rot fungus. After 14 days of
incubation 85 % decolourisation was observed. The decolourisation of Rhodamine B and 6G
was not observed (Itoh and Yatome, 2004). Adsorption of Erythrosine B dye was performed
on fungal biomass of Rhizopus arrhizus (Salvi, 2018). Adsorption of Rhodamine B was
performed by low-cost natural adsorbent Xanthium strumarium L. seed (Khamparia and
Jaspal, 2017). Mycelial waste of Trichoderma harzianum was used for decolourisation of
Rhodamine 6G (Sadhasivam et al., 2007).

6. Conclusion

Increase in industrial development is creating soil, water and air pollution as well as affecting
the whole ecosystem. The SOC’s which are synthesised in industry, from that around 20 %
SOC’s are going in waste which are generating pollution and scarcity of pure water. Removal
of SOC’s from wastewater is practically difficult. Many recent physical, chemical and
biological technique are utilised for removal of such compounds. In the classification of dye,
xanthene derivatives are generating toxic effect in all living organisms. Removal of xanthene
dye from wastewater is carried out by many physicochemical processes but techniques is not
beneficial for higher amount of wastewater. So, increment in recent technologies for removal
of xanthene dye is obligatory for treatment. Biological treatments are not reported sufficiently
for xanthene group as compare to other dyes. Now a days many recent techniques are utilised
for removal of xanthene dye. Still, lot of investigation are remaining in this area.

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