Skip to main content

Advertisement

SpringerLink
Log in

Biological activity of sophorolipids and their possible use as antiviral agents

  • Published:
Folia Microbiologica Aims and scope Submit manuscript

Abstract

Sophorolipids are surface active glycolipids consisting of a hydrophilic sophorose unit and a hydrophobic portion composed of a fatty acid tail. Crude sophorolipid sample contains both acidic and lactonic forms of sophorolipid with different degrees of acetylation and varying lengths of the fatty acid chains depending on the substrates used in the production process. Carboxylic end in the acidic form of the fatty acid is free, whereas in the lactonic form, it is internally esterified. Sophorolipids show different physicochemical properties with wide range of applications for each structural compound. Lactonic form of sophorolipids shows surface tension reducing ability and biological activity, whereas the acidic form possesses better foam forming ability and higher solubility. Presence of acetyl groups gives hydrophilic nature to the sophorolipids which promotes its antiviral and cytokine-stimulating properties. The aim of this review is to explore and suggest the plausibility of sophorolipids as therapeutic and prophylactic agents for the treatment of viral diseases.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  • Ashby RD, Solaiman DKY, Foglia TA (2006) The use of fatty acid esters to enhance free acid sophorolipid synthesis. Biotechnol Lett 28:253–260. doi:10.1007/s10529-005-5527-y

    Article  PubMed  CAS  Google Scholar 

  • Azim A, Shah V, Doncel GF, Peterson N, Gao W, Gross R (2006) Amino acid conjugated sophorolipids: a new family of biologically active functionalized glycolipids. Bioconjug Chem 17:1523–1529. doi:10.1021/bc060094n

    Article  PubMed  CAS  Google Scholar 

  • Banat IM, Makkar RS, Cameotra SS (2000) Potential commercial applications of microbial surfactants. Appl Microbiol Biotechnol 53:495–508

    Article  PubMed  CAS  Google Scholar 

  • Borsanyiova M, Kollarcikova V, Joshi-Navare K, Stipalova D, Storcelova M, Mistrikova J, Zavodska E, Vareckova E, Prabhune A, Bopegamage S (2012) Antiviral activity of sophorolipid a novel biosurfactant. Biopolym Cell 28:59, ISSN 0233-7657

  • Borzeix CF (1999) Use of sophorolipids comprising diacetyl lactones as agent for stimulating skin fibroblast metabolism. Patent WO99/ 62479

  • Cavalero D (2001) Production of sophorolipids by Candida bombicola. Master of Engineering Thesis, McGill University, Montreal, Canada

  • Chattopadhyay D, Chattopadhyay S, Lyon WG, Wilson JT (2002) Effect of surfactants on the survival and sorption of viruses. Environ Sci Technol 36:4017–4024. doi:10.1021/es0114097

    Article  PubMed  CAS  Google Scholar 

  • Chen J, Song X, Zhang H, Qu YB, Miao JY (2006) Production, structure elucidation and anticancer properties of sophorolipid from Wickerhamiella domercqiae. Enzyme Microb Technol 39:501–506. doi:10.1016/j.enzmictec.2005.12.022

    Article  CAS  Google Scholar 

  • Concaix FB (2003) Use of sophorolipids comprising diacetyl lactones as agent for stimulating skin fibroblast metabolism. Patent US 6596265:B1

    Google Scholar 

  • Davila AM, Marchal R, Vandecasteele JP (1994) Sophorose lipid production from lipidic precursors: predictive evaluation of industrial substrates. J Ind Microbiol 13:249–257

    Article  CAS  Google Scholar 

  • Fleurackers SJJ (2006) On the use of waste frying oil in the synthesis of sophorolipids. Eur J Lipid Sci Technol 108:5–12. doi:10.1002/ejlt.200500237

    Article  CAS  Google Scholar 

  • Fu SL, Walner SR, Bowne WB, Hagler MD, Zenilman ME, Gross R, Bluth MH (2008) Sophorolipids and their derivatives are lethal against human pancreatic cancer cells. J Surg Res 148:77–82. doi:10.1016/j.jss.2008.03.005

    Article  PubMed  CAS  Google Scholar 

  • Gorin PAJ, Spencer JFT, Tulloch AP (1961) Hydroxy fatty acid glycosides of sophorose from Torulopsis magnoliae. Can J Chem 39:846–855. doi:10.1111/j.1574-6968.2010.02082

    Article  CAS  Google Scholar 

  • Gross RA (2005) Treatment and prophylaxis of sepsis and septic shock. Patent WO 2005094268:A2

    Google Scholar 

  • Gross RA, Shah V (2004) Antimicrobial properties of various forms of sophorolipids. Patent WO2004044216 A1

  • Gross RA, Shah V (2006) Antifungal properties of various forms of sophorolipids. Patent WO2006069175 A2

  • Gross RA, Shah V (2007) Anti-herpes virus properties of various forms of sophorolipids. Patent WO2007130738 A1

  • Gross RA, Thavasi TR (2013) Modified sophorolipids combinations as antimicrobial agents. Patent US20130142855 A1

  • Gross RA, Shah V, Doncel G (2004) Spermicidal and virucidal properties of various forms of sophorolipids. Patent US 20040242501:A1

    Google Scholar 

  • Gross RA, Shah V, Doncel G (2014) Virucidal properties of various forms of sophorolipids. Patent US 8648055:B2

    Google Scholar 

  • Hardin R, Pierre J, Schulze R et al (2007) Sophorolipids improve sepsis survival: effects of dosing and derivatives. J Surg Res 142:314–319. doi:10.1016/j.jss.2007.04.025

    Article  PubMed  CAS  Google Scholar 

  • Hirata Y, Ryu M, Igarashi K, Nagatsuka A, Furuta T, Kanaya S, Sugiura M (2009) Natural synergism of acid and lactone type mixed sophorolipids in interfacial activities and cytotoxicities. J Oleo Sci 58:565–572. doi:10.5650/jos.58.565

    Article  PubMed  CAS  Google Scholar 

  • Joshi-Navare K, Prabhune A (2013) A biosurfactant-sophorolipid acts in synergy with antibiotics to enhance their efficiency. Biomed Res Int 2013:512495. doi:10.1155/2013/512495

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Joshi-Navare K, Khanvilkar P, Prabhune A (2013) Jatropha oil derived sophorolipids: production and characterization as laundry detergent additive. Biochem Res Int 2013:ID 169797, 11 pages. doi: 10.1155/2013/169797

  • Konishi M, Fukuoka T, Morita T, Imura T, Kitamoto D (2008) Production of new types of sophorolipids by Candida batistae. J Oleo Sci 57:359–369. doi:10.5650/jos.57.359

    Article  PubMed  CAS  Google Scholar 

  • Kurtzman CP, Price NPJ, Ray KJ, Kuo TM (2010) Production of sophorolipid biosurfactants by multiple species of the Starmerella (Candida) bombicola yeast clade. FEMS Microbiol Lett 311:140–146. doi:10.1111/j.1574-6968.2010.02082.x

    Article  PubMed  CAS  Google Scholar 

  • Lang S, Katsiwela E, Wagner F (1989) Antimicrobial effects of biosurfactants. Fett-Lipid 91:363–366. doi:10.1002/lipi.19890910908

    Article  CAS  Google Scholar 

  • Lovaglio RB, dos Santos FJ, Jafelicci M Jr, Contiero J (2011) Rhamnolipid emulsifying activity and emulsion stability: pH rules. Colloids Surf B: Biointerfaces 85:301–305. doi:10.1016/j.colsurfb.2011.03.001

    Article  PubMed  CAS  Google Scholar 

  • Mager H, Rothlisberger R, Wagner F (1987) Use of sophorolse-lipid lactone for the treatment of dandruffs and body odour. Patent EP 0209783:A1

    Google Scholar 

  • Maingault M (1999) Utilization of sophorolipids as therapeutically active substances or cosmetic products, in particular for the treatment of the skin. Patent US 5981497 A

  • Morya VK, Kim EK (2014) Sophorolipids: characteristics, production and application (chapter 4). In: Mulligan CN, Sharma SK, Mudhoo A (eds) Biosurfactants: Research Trends and Application. CRC Press, pp 105-124

  • Mukherji R, Prabhune A (2014) Novel glycolipids synthesized using plant essential oilsand their application in quorum sensing inhibition and as antibiofilm agents. The Scientific World Journal 2014:ID 890709, 7 pp. doi: 10.1155/2014/890709

  • Otto RT, Daniel HJ, Pekin G, Muller-Decker K, Furstenberger G, Reuss M, Syldatk C (1999) Production of sophorolipids from whey. II. product composition, surface active properties, cytotoxicity and stability against hydrolases by enzymatic treatment. Appl Microbiol Biotechnol 52:495–501

    Article  PubMed  CAS  Google Scholar 

  • Prabhune A, Fox SR, Ratledge C (2002) Transformation of arachidonic acid to 19-hydroxy- and 20-hydroxy-eicosatetraenoic acids using Candida bombicola. Biotechnol Lett 24:1041–1044

    Article  CAS  Google Scholar 

  • Schofield MH, Thavasi TR, Gross RA (2013) Modified sophorolipids for the inhibition of plant pathogens. Patent US 20130085067:A1

    Google Scholar 

  • Shah V, Doncel GF, Seyoum T, Eaton KM, Zalenskaya I, Hagver R, Azim A, Gross R (2005) Sophorolipids: novel glycolipid preventive agents for conception and sexual transmission. Antimicrob Agents Chemother 49:4093–4100

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Shah V, Badia D, Ratsep P (2007) Sophorolipids having enhanced antibacterial activity. Antimicrob Agents Chemother 51:397–400. doi:10.1128/AAC.01118-06

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Shao L, Song X, Ma X, Li H, Qu Y (2012) Bioactivities of sophorolipid with different structures against human esophageal cancer cells. J Surg Res 173:286–291. doi:10.1016/j.jss.2010.09.013

    Article  PubMed  CAS  Google Scholar 

  • Shin JD, Lee J, Kima YB, Han I, Kima E (2010) Production and characterization of methyl ester sophorolipids with 22-carbon-fatty acids. Bioresour Technol 101:3170–3174. doi:10.1016/j.biortech.2009.12.019

    Article  PubMed  CAS  Google Scholar 

  • Sleiman JN, Kohlhoff SA, Roblin PM, Wallner S, Gross R, Hammerschlag MR, Zenilman ME, Bluth MH (2009) Sophorolipids as antibacterial agents. Ann Clin Lab Sci 39:60–63

    PubMed  CAS  Google Scholar 

  • Solaiman DKY (2005) Applications of microbial biosurfactants. Inform 16:408–410

    Google Scholar 

  • Spencer JFT, Gorin PAJ, Tulloch AP (1970) Torulopsis bombicola sp. n. Antonie Van Leeuwenhoek 36:129–133

    Article  PubMed  CAS  Google Scholar 

  • Sun XX, Choi JK, Kim EK (2004) A preliminary study on the mechanism of harmful algal bloom mitigation by use of sophorolipid treatment. J Exp Mar Biol Ecol 304:35–49. doi:10.1016/j.jembe.2003.11.020

    Article  CAS  Google Scholar 

  • Tulloch AP, Spencer JFT (1968) Fermentation of long chain compounds by Torulopsis apicola. IV. products from esters and hydrocarbons with 14 and 15 carbon atoms and from methyl palmitoleate. Can J Chem 46:1523–1528

    Article  CAS  Google Scholar 

  • Tulloch AP, Spencer JFT, Deinema MH (1968) A new hydroxy fatty acid sophoroside from Candida bogoriensis. Can J Chem 46:345–348

    Article  CAS  Google Scholar 

  • Van Bogaert INA, Saerens K, De Muynck C, Develter D, Soetaert W, Vandamme EJ (2007) Microbial production and application of sophorolipids. Appl Microbiol Biotechnol 76:23–34. doi:10.1007/s00253-007-0988-7

    Article  PubMed  CAS  Google Scholar 

  • Vollenbroich D, Ozel M, Vater J, Kamp RM, Pauli G (1997) Mechanism of inactivation of enveloped viruses by the biosurfactant surfactin from Bacillus subtilis. Biologicals 25:289–297. doi:10.1006/biol.1997.0099

    Article  PubMed  CAS  Google Scholar 

  • Zhang L, Somasundaran P, Singh SK, Felse AP, Gross R (2004) Synthesis and interfacial properties of sophorolipid derivatives. Colloids Surf A: Physicochem Eng Aspects 240:75–82. doi:10.1016/j.colsurfa.2004.02.016

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Norwegian Financial Mechanism, Mechanism EEA, and Slovak Government and the State Budget of the Slovak Republic (SK 0082) received by S.B., Center of excelence of environmental health, ITMS No. 24240120033 grant of Agency of the Ministry of Education, Science, Research and Sport of the Slovak Republic for the Structural Funds of EU (ASFEU), received by the Slovak Medical University, University Grants Commision, India for the PhD fellowships of R.M. and A.P.

Conflict of interest

None.

Author information

Authors and Affiliations

  1. Enterovirus Laboratory, Faculty of Medicine, Slovak Medical University, Limbova 12, 83303, Bratislava, Slovak Republic

    Maria Borsanyiova & Shubhada Bopegamage

  2. Division of Biochemical Sciences, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India

    Amrita Patil, Ruchira Mukherji & Asmita Prabhune

Authors
  1. Maria Borsanyiova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Amrita Patil
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ruchira Mukherji
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Asmita Prabhune
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Shubhada Bopegamage
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Asmita Prabhune or Shubhada Bopegamage.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Borsanyiova, M., Patil, A., Mukherji, R. et al. Biological activity of sophorolipids and their possible use as antiviral agents. Folia Microbiol 61, 85–89 (2016). https://doi.org/10.1007/s12223-015-0413-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12223-015-0413-z

Keywords

Search

Navigation