International Journal of Cosmetic Science, 2009, 31, 255–261
Review Article
Natural surfactants used in cosmetics: glycolipids
N. Lourith and M. Kanlayavattanakul
School of Cosmetic Science, Mae Fah Luang University, Chiangrai, Thailand
Received 14 October 2008, Accepted 10 December 2008
Keywords: biosurfactant, cosmetics, mannosylerythritol lipids, rhamnolipids, sophorolipids
Synopsis
Cosmetic surfactant performs detergency, wetting,
emulsifying, solubilizing, dispersing and foaming
effects. Adverse reactions of chemical synthesis
surfactant have an effect on environment and
humans, particularly severe in long term. Biode-
gradability, low toxicity and ecological acceptabil-
ity which are the benefits of naturally derived
surfactant that promises cosmetic safety are, there-
fore, highly on demand. Biosurfactant producible
from microorganisms exhibiting potential surface
properties suitable for cosmetic applications espe-
cially incorporate with their biological activities.
Sophorolipids, rhamnolipids and mannosylerythri-
tol lipids are the most widely used glycolipids
biosurfactant in cosmetics. Literatures and patents
relevant to these three glycolipids reviewed were
emphasizing on the cosmetic applications includ-
ing personal care products presenting the cosmetic
efficiency, efficacy and economy benefits of glycoli-
pids biosurfactant.
Résumé
Les tensioactifs sont utilisés en cosmétique pour
leur pouvoir détergent, mouillant, émulsionnant,
solubilisant, dispersant ou moussant. Les consé-
quences graves des surfactants chimiques de syn-
thèse sur l’environnement et sur l’homme agissent
particulièrement à long terme. Aussi, la demande
de surfactant d’origine naturelle plus biodégrad-
Correspondence: Nattaya Lourith, School of Cosmetic
Science, Mae Fah Luang University, Chiangrai, 57100,
Thailand. Tel.: +66 53 916834; fax: +66 53 916831;
e-mail: nattayal@mfu.ac.th
ª 2009 The Authors. Journal compilation
ª 2009 Society of Cosmetic Scientists and the Société Française de Cosmétologie
doi: 10.1111/j.1468-2494.2009.00493.
able avec une faible toxicité et une meilleure
acceptation écologique est en hausse. Les tensioac-
tifs issus de microorganismes offrent des propriétés
de surface convenables pour des applications
cosmétiques et en particulier combinés avec leurs
activités biologiques. Les sophorolipides, les
rhamnolipides et les lipides mannosylérythritol
sont les glycolipides tensioactifs les plus largement
utilisés en cosmétique. Les applications cosmé-
tiques de ces trois glycolipides sont examinées dans
la littérature et les brevets particulièrement pour
leurs bénéfices en termes d’efficacité et d’économie.
Introduction
Surfactants are used in cosmetics and have deter-
gency, wetting, emulsifying, solubilizing, dispersing
and foaming effects [1]. Surfactants are amphi-
philic compounds and contain hydrophobic and
hydrophilic moieties which reduce surface tension
and facilitate the formation of emulsions between
liquids of different polarities. Almost half of all
surfactants produced are for the washing and
cleaning sectors [2].
Initial commercialized surfactants were used in
soap. Most of these commercial surfactants are
chemically synthesized from petroleum derivatives
[3] and are mainly used in washing applications
but can cause significant environmental problems
with long-term usage [4]. Surfactants derived from
natural products will therefore pose fewer environ-
mental problems when selected as multifunctional
cosmetic ingredients because of their safety, odour,
colour and purity [1]. A natural surfactant strictly
refers to a surfactant taken directly from a natural
source [5] as it is believed that natural products
255
Glycolipids as natural surfactants
are safe [6]. Natural surfactants are of particular
interest because of concerns about environmental
conservation, and the use of those surfactants
which are biodegradable and non-toxic would be
consistent with the current trend that natural cos-
metics which are both environmental and animal
friendly are in high demand [7].
Biosurfactants are surfactants which are pro-
duced by microorganisms and have received wide
attention regarding their biodegradability, low tox-
icity, ecological acceptability and availability from
renewable sources [8]. Biosurfactants are structur-
ally diverse depending on the microorganism from
which they were derived, the substrates employed
in the bioprocess and the fermentation conditions
[9]. There are a wide variety of parameters which
can affect the physicochemical characteristics of
biosurfactants, especially surface properties, for
instance, emulsification and foaming properties as
well as biological properties [10]. This functional
diversity, therefore, allows for a variety of applica-
tions depending on the beneficial surface properties
of the biosurfactants which are stable at extremes
of pH, salinity and temperature [11].
Biosurfactants are generally classified into
glycolipids, lipopeptides, phospholipids, fatty acids
and polymeric compounds [12] according to their
chemical structures. The major and most widely
used biosurfactants in cosmetics and personal care
products are glycolipids because of their physico-
chemical properties, biological activities, biocom-
patibility and biodegradability [11–23], and are
used as multifunctional ingredients in the formula-
tion of cosmetics. Potential glycolipid biosurfac-
tants employed in the cosmetics industry are
sophorolipids, rhamnolipids and mannosylerythri-
tol lipids. This review provides a comprehensive
overview of three glycolipid biosurfactants with
physicochemical and biological properties which
are used in the production of cosmetics.
RO
6'
5' 18 CH3
O RO
RO 1'
6" 4' OH O CH
17
5" 2'
O OH 3' (CH2)6
4" OH
4" OH 1"
O CH
2"
CH
OH 3"
OH (CH2)7
1 1
COOH
R = COCH3 and/or H
ª 2009 Society of Cosmetic Scientists and the Société Française de Cosmétologie
256
N. Lourith and M. Kanlayavattanakul
Sophorolipids
Sophorolipids were originally obtained from the
yeast Candida species. The main strains were C.
bomicola ATCC 22214 [24, 25] and Candida apicola
IMET 42747 [26] which produces sophorolipids
as a mixture of 2-O-b-d-glucopyranosyl-d-gluco-
pyranose derivatives acetylated at the 6¢ and/or
6¢¢ positions (Fig. 1). The carboxylic terminal is
either a free acid or intramoleculary esterified
into the lactonic form at the 4¢¢, 6¢ or 6¢¢ positions.
The obtained derivative mixture was composed
of homologue molecules with differing fatty acid
chain length, stereoisomers as well as lactoni-
zation and acetylation patterns. In addition to
Candida sp., Wickerhamiella domericquae was
reported to synthesize more than six glycolipids
including sophorolipids which were identical to
the major components afforded by C. apicola and
Candida bombicola [27, 28] as well as Cryptococcus
curvatus [2].
The surface tension of water is reduced by soph-
orolipids from 72 mN m)1 at 25C to 35–
60 mN m)1 with a critical micelle concentration
(cmc) of 5–80 mg L)1 [12, 29] or generally 10
times less of cmc [30] and is reduced to
26 mN m)1 in some conditions [9]. This low
molecular mass biosurfactant with a low cmc
increased the apparent solubility of hydrocarbons
by incorporating them into the hydrophobic cavi-
ties of micelles [31]. The physicochemical proper-
ties of sophorolipids are regulated by their
chemical structure. It was found that the cmc and
the minimum surface tension had an inverse rela-
tionship with the alkyl ester chain length as the
cmc decreased by 50% per additional CH2 moiety
in the homologues [9]. Sophorolipids also have
biological activity and have shown antimicrobial
properties [32–35]. Mono- and di-acetylated lac-
tones showed the strongest inhibitory effects [36]
RO
6'
5' 18CH3
O
1'
6" 4' OH O CH
17
5" 2'
O OH 3' (CH2)6
1"
O CH
2"
3" CH
OH
(CH2)7
Figure 1 Structures of sophorolipids
O CO
in free acid (left) and lactonic form
(right), respectively.
ª 2009 The Authors. Journal compilation
International Journal of Cosmetic Science, 31, 255–261
Glycolipids as natural surfactants
were the most effective biosurfactants [9] and were
generally more useful for a number of applications
than the acidic forms.
Application of sophorolipids in cosmetics and
personal care products
Sophorolipids have a wide variety of functions and
are used as emulsifiers, foaming agents, solubiliz-
ers, wetting agents and detergents and have bio-
logical activities which are employed as active
ingredients in cosmetics. Multifunctional biosurfac-
tants have several cosmetic applications [37] and
sophorolipids have been shown to have good skin
compatibility and excellent moisturizing properties
[38, 39].
In addition to their emulsifying functions, sorop-
holipids are potent bactericidal agents and are
used in the treatment of acne, dandruff and body
odours [16] and are thought to trigger several
beneficial events related to the protection of hair
and skin. Dermal fibroblast metabolism and colla-
gen neosynthesis shown to be stimulated by soph-
orolipids and inhibitory effects against free radicals
and elastase activity including macrophage activa-
tion and fibrinolytic properties have been demon-
strated. In addition, it has been claimed that
sophorolipids eliminated the surface portion of the
protective layer of the epidermis as part of the
wound healing process. In other words, sophoroli-
pids acted as desquamating and depigmenting
agents [40–42]. Sophorolipids also possibly reduce
subcutaneous fat overload by stimulating leptin
synthesis in adipocytes [43] and are suited for cel-
lulite treatment. Therefore, there are a number of
patients relating to sophorolipids in cosmetics
[44–48].
Sophorolipids are produced commercially by the
Kao Co. Ltd. as humectants, and are present in
the make-up cosmetics ‘Sofina’ and ‘Soliance’
O OH O
H H2
OH
O O C C C O C C COOH
Figure 2 Structures of monorhamn- CH (CH )
2 6
3 3
olipid (left) and dirhamnolipid (right), CH3
respectively. OH OH
ª 2009 The Authors. Journal compilation
ª 2009 Society of Cosmetic Scientists and the Société Française de Cosmétologie
International Journal of Cosmetic Science, 31, 255–261
N. Lourith and M. Kanlayavattanakul
which are produced for skin application and con-
tain ‘Sopholiance S’ as the active ingredient. In
addition, a commercial sophoron, a dish-washing
product containing sophorolipids, was launched
[45] which also has an application as a laundry
product [46]. Sophorolipids are also present in
pencil-shaped lip rouge, lip cream and eye shadow
as well as in compressed powder cosmetics and in
aqueous solutions [47, 48].
Rhamnolipids
Although glycolipids are the best known biosurfac-
tants, rhamnolipids are the most frequently studied
[49]. Two rhamnolipids were produced during the
cultivation of Pseudomonas aeruginosa on glucose,
glycerol or triglycerides. These rhamnolipids were
monorhamnolipid and dirhamnolipid [50] and are
illustrated in Fig. 2. Rhamnolipids are composed of
one or two rhamnose molecules and are bonded to
up to three molecules of hydroxyl fatty acids of
varying chain length from eight up to 14, of
which b-hydroxydecanoic acid is predominant [12,
19, 51]. Rhamnolipids are produced by Pseudomo-
nas sp., and P. aeruginosa produces the leading
commercial biosurfactant which is suitable from a
combined application/cost perspective and is pro-
duced on an industrial scale [23, 52]. Pseudomonas
aeruginosa ATCC 10145, 47T2, UG2 and LBI have
been widely studied to determine the most cost-
effective formation of microbial rhamnolipids [20,
53–55]. The excreted rhamnolipids reduced
the surface tension of water from 72 mN m)1
to 27 mN m)1 with a cmc of 110–150 mg L)1
[50, 55].
Rhamnolipids are not only effective surfactants
but have also shown excellent antimicrobial activi-
ties against fungi [55], bacteria and several other
microorganisms [20]. The surface and biological
properties of these surfactants have been used in
O
H H2 H H2
OH
O O C C C O C C COOH
CH (CH2)6 (CH2)6
3
CH3 CH3
H H2 OH
O
(CH )
2 6 CH
CH3
OH OH
257
Glycolipids as natural surfactants
many health care applications but have particular
use in cosmetics.
Application of rhamnolipids in cosmetics and per-
sonal care products
Rhamnolipids have been used in health care prod-
ucts in several different formulations, for example,
insect repellents, antacids, acne pads, anti-dandruff
products, contact lens solutions, deodorants, nail
care products and toothpastes [37, 56]. These
products require surfactants which have high sur-
face and emulsifying activities [57], particularly
emulsifying activity, which is key to the texture
consistency of these products [18]. In addition to
these special functions, the biological activities
required for cosmetics expand the application of
these surfactants and a delivery system has been
achieved not only for emulsions but also for lipo-
somes [58]. Cosmetics containing rhamnolipids
have been patented and used as anti-wrinkle and
anti-ageing products [59] and were launched in
several dosage forms as commercial skin care cos-
metics [60] because of their skin compatibility and
extremely low skin irritation [18].
Mannosylerythritol lipids
Mannosylerythritol lipids are glycolipid biosurfac-
tants containing 4-O-b-d-mannopyranosyl-meso-
erythritol as the hydrophilic moiety and fatty acids
as hydrophobic moieties [61] (Fig. 3) and were
recently shown to be one of the most promising
biosurfactants used in several applications includ-
ing cosmetics [62] because of their excellent sur-
face activity.
Mannosylerythritol lipids had a high hydrophi-
licity and low critical aggregation concentration
[63] and are suitable as emulsifiers, dispersants
OH
CH3 H2C
H3C n H C OH
OR1 O OR1
n H C OH
O O
R2O CH2
O O
n = 6 ~ 10
1 2
R and R = COCH3 and/or H
ª 2009 Society of Cosmetic Scientists and the Société Française de Cosmétologie
258
N. Lourith and M. Kanlayavattanakul
and detergents [64]. These surfactants have been
found to reduce the surface tension of water to
33.8 mN m)1 at a cmc of 3.6 · 10)4 M with a
hydrophilic–lipophilic balance (HLB) of 12.15, and
have been shown to have antimicrobial activities
[64]. Mannosylerythritol lipids produced by C. ant-
arctica also had a HLB of 8.8, a cmc of
15.8 · 10)6 M and were stable between pH 4 and
10 with thermal stability up to 90C [65]. In addi-
tion to their surface properties, mannosylerythritol
lipids acted as a mild surfactant have biological
activities and are less sensitive to the skin. There-
fore, it is possible that these surfactants may have
an application in the cosmetic industry. Skin care
formulations containing mannosylerythritol lipids
as the surfactant in anti-wrinkle cosmetics [66]
and as the active ingredient in skin care cosmetics
prevent skin roughness [67].
Conclusions
The surface characteristics of glycolipids with a
HLB value close to 10 and a cmc in the range 5
to 150 mg L)1 which are capable of reducing the
surface tension of water to 30 mN m)1, confer
excellent detergency, emulsifying, foaming and dis-
persing properties [11]. These glycolipids have the
potential for widespread use in personal care and
cosmetic products (Table I) because of their low
toxicity, biological activity, biocompatibility and
biodegradability and clearly benefit product effi-
ciency, efficacy and the economy.
Acknowledgements
The authors acknowledge Mae Fah Luang Univer-
sity for facility supported upon this manuscript
preparation.
CH3
O
C m
O
CH3 H2C
H3C n H C OH
O
n H C OH
O O
R2O CH2
O O
Figure 3 Structures of diacylated
n = 6 ~ 10, m = 12 ~ 16
(left) and triacylated (right) mann-
osylerythritol lipids, respectively.
ª 2009 The Authors. Journal compilation
International Journal of Cosmetic Science, 31, 255–261
Glycolipids as natural surfactants N. Lourith and M. Kanlayavattanakul

Table I Surface and biological properties and cosmetics and personal care applications of glycolipids

Mannosylerythritol
Sophorolipids Rhamnolipids lipids

Commercial sources Candida bomicola [12, 29] Pseudomonas Candica antarctica

Candida apicola [9] aeruginosa [50, 55] [64, 65]
Surface tension of water 35–60 mN m)1 [12, 29] 27 mN m)1 [50, 55] NA
(r = 72 mN m)1) 26 mN m)1 [9] 33.8 mN m)1 [64]
reduction at 25C
cmc 5–80 mg L)1 [12, 29] 110–150 mg L)1 3.6 · 10)4 M [64]
[50, 55] 15.8 · 10)4 M [65]
HLB NA NA 12.15 [64]
8.8 [65]
Biological properties Moisturizing [38, 39] Antimicrobial [20, 55] Antimicrobial [64]
Antibacterial [38, 39]
Antioxidant, macrophage
activating,
fibrinolytic properties,
desquamating,
depigmenting [40–42]
Leptin synthesis
stimulating [43]
Applications Dish washer [45] Insect repellent, antacid, Anti-wrinkles
Laundry detergent [46] acne pads, product [66]
Lip rouge and cream, anti-dandruff products, Skin smoothness
eye shadow [47, 48] contact lens solution, product [67]
deodorants, nail care products,
toothpastes [37, 56]
Anti-wrinkles and anti-ageing
products [59]

HLB, hydrophilic–lipophilic balance; NA, not available; cmc, critical micelle concentration.

6. Cordell, G.A. Natural products in drug discovery –

References
1. Rieger, M.N. Surfactant chemistry and classification.
In: Surfactants in Cosmetics, 2nd edn (Rieger, M.N.
and Rhein, L.D., eds), p. 2. Mercel Dekker, New York
(1997).
2. Daniel, H.-J., Reuss, M. and Syldatk, C. Production of
sophorolipids in high concentration from deprotei-
nized whey and rapeseed oil in a two stage fed batch
process using Candida bombicola ATCC 22214 and
Cryptococcus curvatus ATCC 20509. Biotechnol. Lett.
20, 1153–1156 (1998).
3. Ashby, R.D., Nuñez, A., Solaiman, D.K.Y. and Foglia,
T.A. Sophorolipid biosynthesis from a biodiesel co-
product stream. J. Am. Oil Chem. Soc. 82, 625–630
(2005).
4. Mann, R.M. and Bidwell, J.R. The acute toxicity of
agricultural surfactants to the tadpoles of four Aus-
tralian and two exotic frogs. Environ. Pollut. 114,
195–205 (2001).
5. Holmberg, K. Natural surfactants. Curr. Opin. Colloid
Interface Sci. 6, 148–159 (2001).
creating a new vision. Phytochem. Rev. 1, 261–273
(2002).
7. Corley, J.W. All that is good - naturals and their
place in personal care. In: Naturals and Organics in
Cosmetics: From R & D to the Market Place, pp. 7–12.
Allured, Carol Stream, IL (2007).
8. Makkar, R.S. and Cameotra, S.S. Biosurfactant pro-
duction by microorganisms on unconventional car-
bon sources – a review. J. Surfact. Deterg. 2, 237–
241 (1999).
9. Glenns, R.N. and Cooper, D.G. Effect of substrate on
sophorolipid properties. J. Am. Oil Chem. Soc. 83,
137–145 (2006).
10. Dehghan-Noude, G., Housaindokt, M. and Bazzaz,
B.S. Isolation, characterization and investigation
of surface and hemolytic activities of a lipopeptide
biosurfactant produced by Bacillus subtilis ATCC
6633. J. Microbiol. 436, 272–276 (2005).
11. Desai, J.D. and Banat, I.M. Microbial production of
surfactants and their commercial potential. Microbiol.
Mol. Biol. Rev. 61, 47–64 (1997).

ª 2009 The Authors. Journal compilation

ª 2009 Society of Cosmetic Scientists and the Société Française de Cosmétologie
International Journal of Cosmetic Science, 31, 255–261 259
Glycolipids as natural surfactants
12. Kumar, A.S., Mody, K. and Jha, B. Evaluation of bio-
surfactnat/bioemulsifier production by a marine bac-
terium. Bull. Environ. Contam. Toxicol. 79, 617–621
(2007).
13. Zhang, L., Somasundaran, P., Singh, S.K. et al. Syn-
thesis and interfacial properties of sophorolipid deriv-
atives. Colloids Surface A Physicochem. Eng. Asp. 240,
75–82 (2004).
14. Hu, Y. and Ju, L.-K. Purification of lactonic sophor-
olipids by crystallization. J. Biotechnol. 87, 263–272
(2001).
15. Inoue, S., Kimura, Y. and Kinta, M. Dehydrating
purification process for a fermentation product (US
Patent 4 197 166). Kao Soap Co. Ltd., Tokyo
(1980).
16. Mager, H., Rothlisberger, R. and Wagner, F. Use of
sophorose-lipid lactone for the treatment of dandruffs
and body odor (European Patent 0 209 783). Insti-
tut Francais du Petrole, Malmaison (1987).
17. Hall, P.J., Haverkamp, J., Kralingen, C. and Schmidt,
M. Syneristic dual-surfactant detergent composition
containing sophoroselipid (US Patent 5 417 879).
Lever Brothers Co., New York (1995).
18. Haba, E., Pinazo, A., Jáuregui, O. et al. Physico-
chemical characterization and antimicrobial proper-
ties of the rhamnolipids products by Pseudomonas
aeruginosa 47T2 NCIMB 40044. J. Surfact. Deterg. 6,
155–161 (2003).
19. Banat, I., Makkar, R. and Cameotra, S. Potential
commercial applications of microbial surfactants.
Appl. Microbiol. Biotechnol. 53, 495–508 (2000).
20. Benincasa, M., Abalos, A., Oliveria, I. and Manresa,
A. Chemical structure, surface properties and biologi-
cal activities of the biosurfactant produced by Pseudo-
monas aeruginosa LBI from soapstock. Antonie Van
Leeuwenhoek 85, 1–8 (2004).
21. Cameotra, S.S. and Makkar, R.S. Recent application
of biosurfactant as biological and immunological
molecules. Curr. Opin. Microbiol. 7, 262–266 (2004).
22. Kitamoto, D., Isoda, H. and Nakahara, T.J. Functions
and potential applications of glycolipid biosurfac-
tants - from energy-saving materials to gene delivery
carriers. Biosci. Bioeng. 94, 187–201 (2002).
23. Lang, S. and Wullbrandt, D. Rhamnose lipids – bio-
synthesis, microbial production and application poten-
tial. Appl. Microbiol. Biotechnol. 51, 22–32 (1999).
24. Spencer, J.F.T., Gorin, P.A.J. and Tulloch, A.P. Torul-
opsis bombicola sp. Antonie van Leeuwenhoek 36, 129–
133 (1970).
25. Ashby, R.D., Solaiman, D.K.Y. and Foglia, T.A. The
use of fatty acid esters to enhance free acid sophoroli-
pid synthesis. Biotechnol. Lett. 28, 253–260 (2006).
26. Hommel, R.K., Weber, L., Weiss, A. et al. Production
of sophorose lipid by Candida (Torulopsis) apicola
grown on glucose. J. Biotechnol. 33, 147–155
(1994).
ª 2009 Society of Cosmetic Scientists and the Société Française de Cosmétologie
260
N. Lourith and M. Kanlayavattanakul
27. Chen, J., Song, X., Zhang, H. et al. Production, struc-
ture elucidation and anticancer properties of sophor-
olipid from Wickerhamiella domericquae. Enzyme
Microb. Technol. 39, 501–506 (2006).
28. Chen, J., Song, X., Zhang, H. et al. Sophorolipid pru-
duced from the new yeast strain Wickerhamiella
domericquae induces apoptosis in H7402 human liver
cancer cells. Appl. Microbiol. Biotechnol. 72, 52–59
(2006).
29. Lang, S., Brakemeier, A., Heckmann, R. et al. Pro-
duction of native and modified sophorose lipids.
Chimica Oggi/Chem. Today 18, 76–79 (2000).
30. Schippers, C., Geßner, K., Müller, T. and Scheper, T.
Microbial degradation of phenanthrene by addition of
a sophorolipid mixture. J. Biotechnol. 83, 189–198
(2000).
31. Miller, R.M. and Zhang, Y. Measurement of biosurf-
actant-enhanced solubilization and biodegradation of
hydrocarbons. Methods Biotechnol. 2, 59–66 (1997).
32. Kim, K., Yoo, D., Kim, Y. et al. Characteristics of
sophorolipid as an antimicrobial agent. J. Microbiol.
Biotechnol. 12, 235–241 (2002).
33. Pierce, D. and Heilman, T.J. Germicidal composition
(World Patent 1998/16192). Alterna Inc., Los
Angeles, CA (1998).
34. Yoo, D.S., Lee, B.S. and Kim, E.K. Characteristics of
microbial biosurfactant as an antifungal agent
against plant pathogenic fungus. J. Microbiol. Biotech-
nol. 15, 1164–1169 (2005).
35. Van Hamme, J.D., Singh, A. and Ward, O.P. Physio-
logical aspects part 1 in a series of papers devoted to
surfactants in microbiology and biotechnology. Bio-
technol. Adv. 24, 604–620 (2006).
36. Lang, S., Katsiwela, E. and Wagner, F. Antimicrobial
effects of biosurfactants. Fett. Wiss. Technol. Fat Sci.
Technol. 91, 363–366 (1989).
37. Kleckner, V. and Kosaric, N. Biosurfactants for
cosmetics. In: Biosurfactants: Production, Properties,
Applications (Kosaric, N., ed), pp. 329–389. Marcel
Dekker, New York (1993).
38. Yamane, T. Enzyme technology for the lipid industry.
An engineering overview. J. Am. Oil Chem. Soc. 64,
1657–1662 (1987).
39. Brown, M.J. Biosurfactants for cosmetic applications.
Int. J. Cosmet. Sci. 13, 61–64 (1991).
40. Hillion, G., Marchal, R., Stoltz, C. and Boreix, C.F.
Use of a sophorolipid to provide free radical forma-
tion inhibiting activity or elastase inhibiting activity
(US Patent 5 756 471). Institut Francais du Petrole,
Malmaison (1998).
41. Borzeix, C.F. Use of sophorolipids comprising diacetyl
lactones as agent for stimulating skin fibroblast
metabolism (US Patent 6 596 265). Institut Francais
du Petrole, Malmaison (2003).
42. Maingault, M. Utilization of sophorolipids as thera-
peutically active substances or cosmetic products in
ª 2009 The Authors. Journal compilation
International Journal of Cosmetic Science, 31, 255–261
Glycolipids as natural surfactants
particular for the treatment of the skin (US Patent 5
981 497). Institut Francais du Petrole, Malmaison
(1999).
43. Pellecier, F. and André, P. Cosmetic use of sophoroli-
pids as subcutaneous adipose cushion regulation
agents and slimming application (World Patent
2004/108063). LVMH Recherche, Saint Jean de
Braye (2004).
44. Abe, Y., Inoue, S. and Ishida, A. Cosmetic composi-
tion of skin and hair treatment (US Patent 4 297
340). Kao Soap Co., Ltd., Tokyo (1981).
45. Futara, T., Igarashi, K. and Hirata, Y. Low-foaming
detergent compositions (World Patent 2003/
002700). Saraya Co., Ltd., Osaka (2002).
46. Hall, P.J., Haverkamp, J., van Kralingen, C.G. and
Schmidt, M. Laundry detergent composition contain-
ing synergistic combination of sophorose lipid and
nonionic surfactant (US Patent 5 520 839). Lever
Brothers Co., New York (1996).
47. Kawano, J., Suzuki, T., Inoue, S. and Hayashi, S.
Powered compressed cosmetic material (US Patent 4
305 931). Kao Soap Co., Ltd., Tokyo (1981).
48. Kawano, J., Suzuki, T., Inoue, S. and Hayashi, S.
Stick-shaped cosmetic material (US Patent 4 305
929). Kao Soap Co., Ltd., Tokyo (1981).
49. De Lima, C.J.B., França, F.R., Sérvulo, E.F.C. et al.
Enhancement of rhamnolipid production in residual
soybean oil by an isolated strain of Pseudomonas
aeruginosa. Appl. Biochem. Biotechnol. 137, 463–470
(2007).
50. Lang, S. Biological amphiphiles (microbial biosurfac-
tants). Curr. Opin. Colloid Interface Sci. 7, 12–20
(2002).
51. Gunther, N.W., Nunez, A., Fett, W. and Solaiman,
D.K.Y. Production of rhamnolipids by Pseudomonas
chlororaphis, a nonpathogenic bacterium. Appl. Envi-
ron. Microbiol. 71, 2288–2293 (2005).
52. Matsufuji, M., Nakata, K. and Yoshimoto, A. High
production of rhamnolipids by Pseudomonas aerugin-
osa growing on ethanol. Biotechnol. Lett. 19, 1213–
1215 (1997).
53. Chayabutra, C. and Ju, L.K. Polyhydroxyalkanoic
acids and rhamnolipids are synthesized sequentially
in hexadecane fermentation by Pseudomonas aerugin-
osa ATCC 10145. Biotechnol. Prog. 17, 419–423
(2001).
54. Mata-Sandoval, J.C., Karns, J. and Torrents, A. Effect
of nutritional and environmental conditions on the
production and composition of rhamnolipids by
P. aeruginosa UG2. Microbiol. Res. 155, 249–256
(2001).
55. Abalos, A., Pinazo, A., Infante, M.R. et al. Physico-
chemical and antimicrobial properties of new rhamn-
ª 2009 The Authors. Journal compilation
ª 2009 Society of Cosmetic Scientists and the Société Française de Cosmétologie
International Journal of Cosmetic Science, 31, 255–261
N. Lourith and M. Kanlayavattanakul
olipids produced by Pseudomonas aeruginosa AT10
from soy bean oil refinery wastes. Langmuir 17,
1367–1371 (2001).
56. Maier, R.M. and Soberon-Chavez, G. Pseudomonas
aeruginosa rhamnolipids: biosynthesis and potential
applications. Appl. Microbiol. Biotechnol. 54, 625–633
(2000).
57. Vasileva-Tonkova, E., Galabova, D., Karpenko, E. and
Shulga, A. Biosurfactant rhamnolipid effects on yeast
cells. Lett. Appl. Microbiol. 33, 280–284 (2001).
58. Ishigami, Y., Gama, Y., Nagahora, H. et al. Rhamn-
olipid liposomes (US Patent 4 902 512). Agency of
Industrial Science and Technology and Shin-Etsu
Chemical Co., Ltd., Japan (1988).
59. Piljac, T. and Piljac, G. Use of rhamnolipids in
wound healing, treating burn shock, atherosclerosis,
organ transplants, depression, schizophrenia and cos-
metics (European Patent 1 889 623). Paradigm Bio-
medical Inc., New York (1999).
60. Desanto, K. Rhamnolipid-based formulations (Word
Patent 2008/013899). Aurora Advanced Beauty
Labs, St. Petersburg, FL (2008).
61. Morita, T., Konishi, M., Fukuoka, T. et al. Discovery
of Pseudozyma rugulosa NBRC 10877 as a novel pro-
ducer of the glycolipid biosurfactants, mann-
osylerythritol lipids, based on rDNA sequence. Appl.
Microbiol. Biotechnol. 73, 305–313 (2006).
62. Kitamoto, D., Isoda, H. and Nakahara, T. Functional
and potential application of glycolipid biosurfactants.
J. Biosci. Bioeng. 94, 187–201 (2002).
63. Imura, T., Ohta, N., Inoue, K. et al. Naturally engi-
neered glycolipid biosurfactant leading to distinctive
self-assembled structures. Chem. Eur. J. 12, 2434–
2440 (2006).
64. Fukuoka, T., Morita, T. and Konishi, H. Structural
characterization and surface-active properties of a
new glycolipid biosurfactant, mono-acylated
mannosylerythritol lipid, produced from glucose by
Pseudozyma antarctica. Appl. Microbiol. Biotechnol. 76,
801–810 (2007).
65. Kim, H.-S., Jeon, J.-W., Kim, S.-B. et al. Surface and
physico-chemical properties of a glycolipid biosurfac-
tant, mannosylerythritol lipid, from Candica antarc-
tica. Biotechnol. Lett. 24, 1637–1641 (2002).
66. Eiko, K. and Toshi, T. Dermatological anti-wrinkle
agent (World Patent 2008/001921). Showa Denko
K.K., Tokyo (2008).
67. Masaru, K., Michiko, S. and Shuhei, Y. Skin care
cosmetic and skin and agent for preventing skin
roughness containing biosurfactants (World Patent
2007/060956). Toyo Boseki Kabu Shiki Kaisha and
National Industrial Science and Technology, Osaka,
Japan (2007).
261