POTENTIAL BIOMEDICAL AND PHARMACEUTICAL APPLICATIONS OF MICROBIAL SURFACTANTS

www.wjpps.com Vol 4, Issue 04, 2015. 1557
Harjot et al. World Journal of Pharmacy and Pharmaceutical Sciences
POTENTIAL BIOMEDICAL AND PHARMACEUTICAL
APPLICATIONS OF MICROBIAL SURFACTANTS
Bhairav Prasad, Dr. Harjot Pal Kaur*
and Dr. Sukhvir Kaur
SUS College of Research and Technology, Tangori, Mohali.
ABSTRACT
Many microorganisms are able to produce a wide range of amphipathic
compounds, with both hydrophilic and hydrophobic moieties present
within the same molecule which allow them to exhibit surface
activities at interfaces and are generally called biosurfactants.
Biosurfactants are versatile, structurally diverse group of surface-active
substances produced by microorganisms and have variety of
applications in the sectors including bioremediation, food industry,
agriculture and pharmaceuticals. Interest in biosurfactant production
has markedly increased during the past decade, although large-scale
production has not been possible because of low production yields and
high total costs. At present, biosurfactants have gained importance in environmental
applications, while new applications in the pharmaceutical, biomedical, cosmetic and food
industry, with a high added value, are still developing. Recently, the potential applications of
biosurfactants in the biomedical field have increased. Their antibacterial, antifungal and
antiviral activities make them relevant molecules for applications in combating many
diseases and as therapeutic agents. In addition, their role as anti-adhesive agents against
several pathogens indicates their utility as suitable anti-adhesive coating agents for medical
insertional materials leading to a reduction in a large number of hospital infections without
the use of synthetic drugs and chemicals. This article emphasizes the medicinal and
therapeutic perspective of biosurfactants. With these specialized and cost-effective
applications, biosurfactants can be considered as an interesting option for the near future.
KEYWORDS: Antiadhesive, Anticancer, Antimicrobial, Biosurfactant, Gene transfection,
Immunoadjuvants.
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*Correspondence for
Author
Dr. Harjot Pal Kaur
SUS College of Research
and Technology, Tangori,
Mohali.
Article Received on
19 March 2015,
Revised on ------------------,
Accepted on 27 March 2015

INTRODUCTION
Biosurfactants are surface active agents with wide range of properties including reduction of
surface and interfacial tensions of liquids. Surface tension is defined as the free surface
enthalpy per unit area[1]
and is the force acting on the surface of a liquid leading to decrease
the area of that surface. Already reported surfactants, both synthetic and natural, are capable
of reducing the surface tension of water from 72 mNm−1
to 27 mNm−1
.[2]
Surfactants are
extensively used for industrial, agricultural, food, cosmetic and pharmaceutical applications.
Most of these surfactants are chemically synthesized and are potentially toxic to the
environment.[3,4]
Microbial-derived surfactants or biosurfactants are amphipathic molecules
produced by a wide variety of microbes containing hydrophilic and hydrophobic domain that
increase the solubility of poorly soluble compounds in water by reducing the surface tension.
[5]
Surface active compounds produced by microorganisms are of two main types; first, that
reduce surface tension at the air water interface (biosurfactants) and second, that reduce
interfacial tension between immiscible liquids, or at the solid-liquid interface (bioemulsifier).
Biosurfactants usually display emulsifying capacity but bioemulsifier do not necessarily
reduce surface tension.[6,7]
A wide spectra of microbial surfactants, including glycolipids,
lipopeptides, fatty acids, and polymeric biosurfactants, have been found to have surface
activity.[8]
Biosurfactants have important advantages relative to chemically synthesized
surfactants, such as higher biodegradability, low toxicity, greater environmental
compatibility, better foaming properties and stable at extreme pH, salinity and
temperature.[9,10]
Microbial surfactants are considered to be secondary metabolites, play important role for the
survival of biosurfactant producing microorganisms by facilitating nutrient transport or
microbe-host interactions or by acting as biocide agents[11, 12]
, bacterial pathogenesis and
biofilm formation.[13, 14]
Biosurfactant have been found to possess several properties of
restorative as well as biomedical importance[15]
and also have potent antibacterial,
antifungal[16]
and antiviral properties, inhibit fibrin clot formation and anti-adhesive action
against several pathogenic microorganisms.[12, 17, 18]
Here, in this article role and applications
of microbial surfactants were discussed with main focus on the most recent and appealing
medicinal and pharmaceutical perspectives.

CLASSIFICATION AND BIOLOGICAL ORIGIN OF BIOSURFACTANTS
The synthetic surfactants are generally classified according to the nature of their polar group
but biosurfactants have been categorized mainly by their chemical composition and microbial
origin.[13]
Biosurfactants have been broadly classified into low molecular-mass molecules
(efficiently lower surface and interfacial tension, include glycolipids, lipopeptides and
phospholipids) and high molecular-mass polymers (more effective as emulsion-stabilizing
agents and bioemulsifier, include polymeric and particulate surfactants).[19]
Most
biosurfactants are either anionic or neutral with a long-chain fatty acids or fatty acid
derivatives as hydrophobic moiety, whereas the hydrophilic moiety can be a carbohydrate,
amino acid, phosphate or cyclic peptide.[20]
The major classes of biosurfactants include
glycolipids, lipopeptides and lipoprotein, fatty acid, phospholipids, neutral lipids and
polymeric surfactants.
Glycolipids
Glycolipids are the most common biosurfactants contain carbohydrates in combination with
long chain aliphatic acids or hydroxyaliphatic acids.[21, 22]
Rhamnolipids, trehalolipids and
sophorolipids are best known glycolipids produced by a variety of microorganisms.[23]
Rhamnolipids
Glycolipids composed of one or two molecules of rhamnose linked with one or two
molecules of β-hydroxy-decanoic acid (Fig. 1) are called rhamnolipids. The production of
rhamanose containing glycolipids was first described in Pseudomonas aeruginosa.[24]
The
two principal types of glycolipids produced by Pseudomonas aeruginosa are L-rhamnosyl-L-
rhamnosyl-β-hydroxydecanoyl-β-hydroxydecanoate and L-rhamnosyl- β-hydroxydecanoyl-β-
hydroxydecanoate commonly referred as rhamnolipids I and II respectively.[25-27]
Trehalolipids
Trehalolipids are disaccharides trehalose linked at C-6 and C-6’ to mycolic acids which is
associated with most species of Mycobacterium, Nocardia and Corynebacterium (Fig. 2).
Mycolic acids are long-chain, α- branched β- hydroxy fatty acids. The size of the
trehalolipids, structure of mycolic acids, the number of carbon atoms and the degree of
unsaturation varies organisms to organisms.[28]
The most common trehalolipids are trehalose
dimycolate and anionic trehalose lipid produced by Rhodococcus erythropolis and
Artrobacter sp. lowered the surface and interfacial tension in culture broth from 25 to 40 and
1to 5 mN/m respectively.[29]

Sophorolipids
Sophorolipids are glycolipids consists of a dimeric carbohydrate sophorose linked to a long
chain hydroxyl fatty acid by glycosidic linkage and mainly produced by yeast such as
Torulopsis bombicola, T. petrophilum and T. apicola. [30, 31]
Usually, sophorolipids occur as a
mixture of macrolactones and free acid form (Fig. 3A & 3B). It has been shown that the
lactone form of the sophorolipid is essential, for many applications.[32]
Lipopeptides and Lipoproteins
Lipopeptides and lipoprotein are mostly consists of a lipids attached with polypeptide chain.
Cyclic peptide gramicidins (decapeptide antibiotic) and polymyxin (lipopeptide antibiotic)
produced by Bacillus brevis and B. polymyxa respectively posseses remarkable biosurfactant
activity.[33]
Surfactin
Surfactin (lipopeptide produced by Bacillus subtilis ATCC 21332), is one of the most
powerful biosurfactant (Fig. 4). It is composed of a seven amino acid ring structure coupled
to a fatty acid (3-hydroxy-13-methyl tetradecanoic acid) chain via lactone linkage.[34]
Surfactin produced by B. subtilis has been shown to increase solubility and bioavailability of
a petrochemical mixture and also stimulate indigenous microorganisms for enhanced
biodegradation of diesel contaminated soil.[35]
Fatty Acids, Phospholipids and Neutral Lipids
Several bacteria and yeasts produce large quantities of fatty acid and phospholipid surfactants
during growth on n-alkanes and other hydrocarbons. The HLB (hydrophilic and lipophilic
balance) of the produced surfactants is directly related to the length of the hydrocarbon chain
and their structures.[36]
Corynebacterium alkanolyticum produces a phospholipid
biosurfactant with a relatively low yield; however, the use of self-cycling fermentation
processes resulted in three fold increase in the biosufactant production. The yield could be
further increased to five fold by the addition of high amount of limiting substrates.[37]
Phosphatidylethanolamine produced by Rhodococcus erythropolis grown on n-alkane helps
in lowering the interfacial tension between water and hexadecane to less than 1mN/m and a
CMC of 30 mg/l.[38]

Polymeric Biosurfactants
The most common polymeric biosurfactants are emulsan (Fig. 5), liposan, alasan, lipomanan
and other polysaccharide-protein complexes. Alasan is an anionic covalently bound alanine
containing hetero-polysaccharide protein biosurfactant with a molecular weight
approximately 1MDa produced from Acinetobacter radioresistens KA-53. The protein
component of alasan appears to play an important role in both the structure and activity of the
complex and found to be 2.5 to 3 times more active after being heated at 100o
C under neutral
or alkaline condition.[39]
Similarly, Yarrowia lipolytica, a tropical marine strain produced an
emulsifier complex (lipid-carbohydrate-lipid) associated with the cell wall in earlier stages of
growth but displayed extracellularly in the stationary phase in the presence of alkanes or
crude oil.[40]
Particulate Biosurfactants
Particulate biosurfactants are extracellular membrane vesicles partition hydrocarbons that
form micro emulsion and play an important role in alkane uptake by microbial cells. Vesicles
of Acinetobacter sp. strain HO1-N with a diameter of 20-50 nm and a buoyant density of
1.158cubic g/cm are composed of protein, phospholipids and lipopolysaccharide.[13]
POTENTIAL BIOMEDICAL APPLICATIONS
The use and potential commercial applications of biosurfactants in the medical field has
increased during the past decade. It have also been demonstrated that the biosurfactants could
have a wide range of application in pharmaceutical fields.[12]
Several surfactants produced by
bacteria and fungi have strong antibacterial, antifungal, antiviral, antitumor and anticancer
activity.
Antimicrobial Activity
The diverse compositions of microbial surfactants confer them to exhibit versatile
performance.[41, 42]
Due to its configuration, biosurfactant is believed to exert its toxicity on
the plasma membrane permeability similar to detergent. The biosurfactants possess strong
antibacterial, antifungal and antiviral properties.[43]
The antimicrobial activity of two
biosurfactants obtained from probiotic bacteria, Lactococcus lactis 53 and Streptococcus
thermophilus A, have been investigated against a variety of bacterial and yeast strains isolated
from explanted voice prostheses and it was found that both the biosurfactants have a high
antimicrobial activity even at low concentration.[44]

Probiotics have long been known for their antimicrobial activity and for the capacity to
interfere with the adhesion and formation of biofilms of pathogens to epithelial cells of
urogenital and intestinal tracts,[45]
catheter materials and voice prostheses,[12,44]
and the
mechanisms of this interference have been demonstrated to include, among others, the release
of biosurfactants.[15,46]
Recently it was demonstrated that the surfactants obtained from three
Lactobacillus acidophilus strains inhibited Staphylococcus epidermidis and S. aureus biofilm
integrity and formation.[47]
Another interesting application of probiotics that is gaining more
interest is their use in preventing oral infections. The role of probiotics on oral health has
been thoroughly investigated.[48-50]
It has been reported that the biosurfactant from
Streptococcus mitis inhibited adhesion of Streptococcus sobrinus HG 1025 and Streptococcus
mutans ATCC 25175 to bare enamel, and also inhibit the adhesion of S. sobrinus HG 1025 to
salivary pellicles.[51]
It was suggested that these reductions may be attributed to increased
electrostatic repulsion between the bacteria and the biosurfactant-coated pellicles.[52]
Biosurfactants from different microorganisms viz., MELs (glycolipid biosurfactant) produced
by Candida antartica, and rhamnolipids from P. aeruginosa,[53]
lipopeptides produced by B.
subtilis 31 and B. licheniformis have been shown to have potent antimicrobial activities.[46]
A biosurfactant from B. subtilis R14 shown antibacterial activity against 29 bacterial strains
and results demonstrated that lipopeptide have a broad spectrum of action including microbial
strain with multidrug-resistant profile.[11]
Similarly, another biosurfactant produced by a
marine B. circulans had strong antibacterial activity against G (+) and G (-) pathogenic and
semi pathogenic bacteria including MDR strain.[54]
The antifungal activities of biosurfactants
have long been known, although their action against human pathogenic fungi has been rarely
described.[55,56].
Recently, a glycolipid named flocculosin isolated from yeast-like fungus, P.
flocculosa, was shown to display in vitro antifungal activity against several pathogenic
yeasts, associated with human mycoses.[57]
The antiviral activity of biosurfactants, mainly surfactin and its analogues has been
reported.[58]
The potential inactivation of enveloped viruses, such as retroviruses and herpes
viruses, compared to non-enveloped viruses, suggests that this inhibitory action may be
mainly due to physico-chemical interactions between the virus envelope and the surfactant.[59]
An antimicrobial lipopeptides produced by B. subtilis, inactivated cell-free virus of porcine
parvovirus, pseudorabies virus, newcastle disease virus and bursal disease virus, while it
effectively inhibited replication and infectivity of the newcastle disease virus and bursal

disease virus but had no effect on pseudorabies virus and porcine parvovirus.[60]
The
biosurfactant sophorolipids have activity against human immunodeficiency virus.[61]
Similarly, a rhamnolipid and its complex with alginate, both produced by a Pseudomonas sp.
strain, showed significant antiviral activity against herpes simplex virus types 1 and 2.[62]
The
suppressive effect of the compounds on herpes simplex virus replication was dose-dependent
and occurred at concentrations lower than the critical micelle concentration.[63]
Gene Rescue
Gene therapy, an efficient and safe method for introducing exogenous nucleotides into
mammalian cells is critical for basic sciences and clinical applications. It has been reported
that lipofection using cationic liposomes, a method of gene transfection is considered to be a
potential way to deliver foreign gene to the target cells without any side effects.[64-66]
A
comparative study of commercially available cationic liposomes and liposomes based on
biosurfactants shown increasing efficiency of gene transfection.[22]
Immunological Adjuvants
Adjuvants are protein when mixed with conventional antigen, surprisingly amplified the
immune response. Some bacterial lipopeptides comprise potent non-toxic and non-pyrogenic
act as immunological adjuvants when mixed with conventional antigens. A marked
improvement in the humoral immune response was obtained with the low molecular mass
antigens iturin AL, herbicolin A and microcystin (MLR) coupled to poly-L-lysine (MLR-
PLL) in rabbit and chickens.[12]
Immunomodulator Agents
It has been reported that sophorolipids are promising modulators of the immune response. It
has been also demonstrated that sophorolipids, decreased sepsis related mortality at 36 h in
vivo in a rat model of septic peritonitis by modulation of nitric oxide, adhesion molecules and
cytokine production. In addition to that it also decreased IgE production in vitro in U266 cells
possibly by affecting plasma cell activity. The results show that sophorolipids decrease IgE
production in U266 cells by suppressing the genes involved in IgE pathobiology in a
synergistic manner. This data can support the utility of sophorolipids as an anti-inflammatory
agent and a novel potential therapy in diseases of altered IgE regulation.[67,68]

Anti-human Immunodeficiency Virus and Sperm-immobilizing Activity
The increased incidence of human immunodeficiency virus (HIV)/AIDS in women aged 15-
49 years has identified the urgent need for a female-controlled, efficacious and safe vaginal
topical microbicide.[28]
It has been reported that sophorolipid produced by C. bombicola and
its structural analogues have been studied for their spermicidal, anti-HIV and cytotoxic
activities. The sophorolipid diacetate ethyl ester derivative is the most potent spermicidal and
virucidal agent of the series of sophorolipids studied.[61]
Its virucidal activity against HIV and
sperm-immobilizing activity against human semen are similar to those of nonoxynol-9.
However, it also induced enough vaginal cell toxicity to raise concerns about its applicability
for long-term microbicidal contraception.[28]
Anti-adhesive Agents in Surgical
The microbial sufactnts or biosurfactants have been found to inhibit the adhesion of
pathogenic organisms to the surgical instruments or to infection sites thus might constitute a
new alternative and effective means of combating colonization of pathogenic
microorganisms.[54,69]
It has been demonstrated that pre-coating vinyl urethral catheters
treated with surfactin solution before inoculation with media resulted in decreased amount of
biofilm formation by gram negative bacteria like S. typhimurium, S. enterica, E. coli, and P.
mirabilis. Microbial surfactants significantly reduced microbial population on prostheses and
also induced a decrease in the air flow resistance that occurs on voice prostheses after biofilm
formation.[70]
Pulmonary Surfactant
A deficiency of pulmonary surfactant, a phospholipid protein complex is responsible for the
failure of respiration in prematurely born infants. Isolation of genes for protein molecules of
this surfactant and cloning in bacteria has made possible its fermentative production for
medical applications.[13]
Anticancer Activity
It has been recently reported that the glycolipids produced by some bacteria and yeasts have
potent anticancer activity. The seven microbial extracellular glycolipids, including
mannosylerythritol lipids-A, mannosylerythritol lipids-B, polyol lipid, rhamnolipid,
sophorose lipid, succinoyl trehalose lipid (STL)-1 and succinoyl trehalose lipid-3 have been
investigated and found that except rhamnolipdis all these glycolipds involved in induced cell
differentiation instead of cell proliferation in the human pro-myelocytic leukaemia cell line

HL60.[71,72]
STL and MEL markedly increased common differentiation characteristics in
monocytes and granulocytes respectively. Exposure of B16 cells to MEL resulted in the
condensation of chromatin, DNA fragmentation and sub-G1 arrest (the sequence of events of
apoptosis). In addition, exposure of PC12 cells to MEL enhanced the activity of acetylcholine
esterase and interrupted the cell cycle at the G1 phase, with resulting outgrowth of neurites
and partial cellular differentiation. This suggests that MEL induces neuronal differentiation in
PC12 cells and provides the groundwork for the use of microbial extracellular glycolipids as
novel reagents for the treatment of cancer cells.[73]
It have been suggested that the
sophorolipid produced by W. domercqiae have anticancer activity. The cytotoxic effects of
sophorolipid on cancer cells of H7402, A549, HL60 and K562 were investigated by MTT
assay. The results showed a dose-dependent inhibition ratio on cell viability according to the
drug concentration <62.5 g/ml.[74]
Recovery of Intracellular Products
Biosurfactants are very much similar to chemical surfactant or detergents and can
permeabilise or lyse cells after the fermentation for recovery of intracellular products. It have
been reported that the permeabilization of E. coli cells was done by reverse micelle solution
to facilitate penicillin acyclase extraction.[75]
In down streaming process for the recovery of
intracellular protein from microbial cells were achieved through aggressive mechanical cell
disintegration. However these mechanical methods solubilise and disrupt most of the protein
components associated with cell walls, organelles and membrane. Therefore more selective
permeabilization achieved by using compounds that making microbial cell more porous and
release target protein with highest efficiencies. Biosurfactants can be the choice of molecule
for membrane permeabilization.[76]
Thus the biosurfactants could be a promising purification
option for the recovery of purified intracellular proteins to permeabilize cells with selective
protein. In selecting biosurfactants for these applications the primary consideration should be
the efficiency, selectivity and also important to insure the biosurfactant has no negative
impact on the stability of the product as these are bioactive molecules and may bind to
protein and other molecules.[75, 76]
Biosurfactants for Cosmetics
The biosurfactants exerts many properties such as emulsification and de-emulsification,
foaming, water binding capacity, spreading and wetting properties effect on viscosity and on
product stability can efficiently be utilized by cosmetics industry. Surfactants as emulsifiers,

foaming agents, solubilizers, wetting agents, cleansers, antimicrobial agents, mediators of
enzymes action in various dosages forms like creams, lotions, liquids, pastes, powders, sticks,
gels, films, sprays could be used and may be replaced by biosurfactants.[77-80]
Biosurfactants
are used in insect repellents, antacids, bath products, acne pads, antidandruff products,
contact lens solution, hair colours and care products, deodorants, nail care, body message
accessories, lip markers, eye shades, mascaras, soaps, tooth pastes and polishes, denture
cleansers, adhesives, antiperspirants, lubricated condoms, baby products, foot care,
antiseptics, shampoos, conditioners, shave and depilatory products, moisturizers, health and
beauty products.[3]
All of these applications of surfactants could be replaced by using
microbial surfactants.[81]
FIGURES
O O
H
C
H2
C C
(CH2)6
O
H
C
H2
C COOH
O
CH3
(CH2)6
CH3
CH3
OH
O
CH3
OH
OH OH
OH
Fig. 1. Structure of Rhamnolipid[82]
O
CH2O
OH
OH
OH
O
O
C C
H
(CH2)n
HOH
C (CH2)m
CH3
CH3
O
OH
OH
OH
CH2OOC
H
C
(CH2)n
HOHC
CH3
m(H2C)H3C
Figure 2. Structure of Trehalose Lipids[83]

O
O
0
OH
OH
CH2OH
CH
CH3
(CH2)6
O
CH2OH
OH
OH
CH
CH
(CH2)7O
Lactone form
Fig. 3A. Structure of Lactonized Form of Sophorolipids[32]
O
O
0
OH
OH
CH2OH
CH
CH3
(CH2)6
O
CH2OH
OH
OH
OH
CH
CH
(CH2)7
COOH
Acid form
Fig. 3B. Structure of Free-acid Forms of Sophorolipids[30, 31]
O
N
H
O
O
NH
FA
HN
O
O
HN O
R
O
O
NH
O
O
O
O
N
H
O
O
Fig. 4. Structure of Surfactin[84]

O
O
O
O
O
O
NH
C
OH
COO
OH
HO
OCOH2C
NHAc
H3C
AcHN
NHAc
O
Fig. 5. Structure of Emulsan Like Polymer[85]
CONCLUSIONS AND FUTURE POTENTIAL
Surfactants are an important class of chemical compounds posses both hydrophilic and
hydrophobic moieties. The microbial derived surfactants have several advantages over
synthetic counterpart such as ecofriendly, biodegradable, less toxic and non mutagenic in
nature. Due to their above trait the microbial surfactants find versatile applicability in many
household and industrial sectors. Currently, the surfactants and biosurfactants derived
products are progressively entering into the market. Another interesting feature of
biosurfactants has led to a wide range of potential applications in the pharmaceutical field.
They are useful as antibacterial, antifungal and antiviral agents, immunomodulatory
molecules and in vaccines and gene therapy. Biosurfactants have been used for gene
transfection, as ligands for binding immunoglobulins, as immunoadjuvants for antigens and
also as inhibitors for fibrin clot formation and activators of fibrin clot lysis. Promising
alternatives to produce potent biosurfactants with altered antimicrobial profiles and decreased
toxicity against mammalian cells may be exploited by genetic alteration of biosurfactants.
Furthermore, biosurfactants have the potential to be used as anti-adhesive biological coatings
for medical insertional materials, thus reducing hospital infections and use of synthetic drugs
and chemicals. They may also be incorporated into probiotic preparations to combat
gastrointestinal, urogenital tract infections and pulmonary immunotherapy. In spite of the
immense potential the commercial use of biosurfactants is still limited due to their high
production and recovery cost. Optimized growth conditions using inexpensive renewable
substrates (agro-industrial wastes), mutant high producer and novel strains, efficient methods
for isolation and purification of biosurfactants could make their production economical.
Further investigations on human cells and natural micro biota are needed to validate the use

of biosurfactants in several biomedical and health related areas. Nevertheless, there appears
to be great potential for their use in the environmental and medical science arena waiting to
be fully exploited.
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