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Licensed Unlicensed Requires Authentication Published by De Gruyter January 20, 2022

Improved synthesis of sophorolipid biosurfactants using industrial by-products and their practical application

  • Sri Dharini Sivagiri

    Sri Dharini Sivagiri is M.Tech (Green Technology) at the Institute of Chemical Technology, Mumbai.

    , Suraj N. Mali

    Suraj N. Mali is M. Pharm (Pharmaceutical Chemistry) at the Institute of Chemical Technology, Mumbai.

    and Amit P. Pratap

    Amit P. Pratap completed his graduation and post graduation in Oil Technology in 2001 and obtained his doctorate degree in 2006 from Institute of Chemical Technology, Mumbai. He served the department as a ‘Professor J. G. Kane Academic Associate’ for over two years and worked as Assistant Professor over 10 years. At present he is Associate Professor and since 15 years he is involved in the teaching, research and development in the field of vegetable oil based lubricants, additives and biosurfactants. His research interest includes triboapplications of vegetable oils, structural modifications of oils and fats, biosurfactants and specialty products.

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Abstract

Surfactants are amphipathic molecules that are generally chemically derived. Compared to these surfactants, biosurfactants have a better environmental profile and are derived from microorganisms. Among the biosurfactants, sophorolipids (SLs) are probably the most promising biosurfactants. In general, the costs of raw materials in the synthesis of biosurfactants accounts for about 10–30% of the total costs. These costs can be reduced to some extent by using industrial by-products as substrates for the synthesis of SLs. In this study, sunflower acid oil (SAO), a by-product of sunflower oil refining, and crude glycerol (so-called “sweetwater”), which is the glycerol-rich solution from the mixed fat hydrolysis reaction, also an industrial by-product, are used for the synthesis of SLs. We obtained comparable yields (0.8/50 mL) to previous reports using a combination of treated SAO (10% w/v) and sweetwater (19% w/v). For the bleaching process, we used 1% and 3% activated earth for normal and heavy treatments over a period of 1 h and 3 h, respectively. Glycerol is inexpensively available in the form of sweetwater from fat-splitting plants and was used as the hydrophilic source. The purification of the SL can be achieved by crystallization at pH 7. The purified SL is analyzed by thin layer chromatography (TLC), Fourier transform infrared spectroscopy (FTIR), and high performance liquid chromatography (HPLC). Then, it was incorporated into different liposomal formulations for the encapsulation of the non-steroidal anti-inflammatory drug (NSAID) ibuprofen. The ratio of drug to cholesterol and SL was 1:1:0.5. The liposomal structures were examined for their size of 2 µ by direct light scattering.


Corresponding author: Amit P. Pratap, Department of Oils, Oleochemicals and Surfactants Technology, Institute of Chemical Technology (University Under Section-3 of UGC ACT 1956, Formerly UDCT/ UICT, NBA Accredited “A” Grade by MHRD), Nathalal Parekh Road, Matunga (East), Mumbai 400 019, India, E-mail:

About the authors

Sri Dharini Sivagiri

Sri Dharini Sivagiri is M.Tech (Green Technology) at the Institute of Chemical Technology, Mumbai.

Suraj N. Mali

Suraj N. Mali is M. Pharm (Pharmaceutical Chemistry) at the Institute of Chemical Technology, Mumbai.

Amit P. Pratap

Amit P. Pratap completed his graduation and post graduation in Oil Technology in 2001 and obtained his doctorate degree in 2006 from Institute of Chemical Technology, Mumbai. He served the department as a ‘Professor J. G. Kane Academic Associate’ for over two years and worked as Assistant Professor over 10 years. At present he is Associate Professor and since 15 years he is involved in the teaching, research and development in the field of vegetable oil based lubricants, additives and biosurfactants. His research interest includes triboapplications of vegetable oils, structural modifications of oils and fats, biosurfactants and specialty products.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

Appendix

Fermentation conditions

Previously reported conditions

From the previous investigations carried out, it is evident that a high yield of SLs is obtained when both hydrophobic and hydrophilic sources are provided during fermentation. The most commonly used hydrophobic source of SL synthesis is oleic acid together with a hydrophilic source such as glucose. For the synthesis of SLs, yeast extract and urea are generally used as nitrogen sources.

LC-MS of purified SL

ESI tandem mass spectra (MS Q-TOF LC-MS, AGLIENT 6550A) were used to determine the identity and concentration of the compounds within the structure of the SLs. Mass spectrum of positive ions provided by Sophisticated Analytical Instrument Facility (SAIF), IIT Bombay, Mumbai, India was used. A mixture of acetonitrile and methanol was used as the mobile phase for HPLC, which was then analyzed using the mass spectrometer.

Figure A1: 
The LCMS spectrum of Sophorolipid.
Figure A1:

The LCMS spectrum of Sophorolipid.

References

1. Hall, P., Haverkamp, J., Van Kralingen, C., Schmidt, M. Laundry detergent composition containing synergistic combination of sophorose lipid and nonionic surfactant. US Patent 5520839, 1996.Search in Google Scholar

2. Akari, S., Akari, Y. Method of modifying quality of wheat flour product, Japanese Patent 61205449, 1987.Search in Google Scholar

3. Jadhav, J. V., Pratap, A. P., Kale, S. B. Evaluation of sunflower oil refinery waste as feedstock for production of sophorolipid Process. Biochemistry 2019, 78, 15–24; https://doi.org/10.1016/j.procbio.2019.01.015.Search in Google Scholar

4. Mulligan, C., Yong, R., Gibbs, B. Heavy metal removal from sediments by biosurfactants. J. Hazard Mater. 2001, 85, 111–125; https://doi.org/10.1016/S0304-3894(01)00224-2.Search in Google Scholar

5. Morya, V., Ahn, C., Jeon, S., Kim, E. Medicinal and cosmetic potentials of sophorolipids. Mini Rev. Med. Chem. 2013, 13, 1761–1768; https://doi.org/10.2174/13895575113139990002.Search in Google Scholar

6. Kim, K., Yoo, D., Kim, Y., Lee, B., Shin, D., Kim, E. Characteristics of sophorolipid as an antimicrobial agent. J. Microbiol. Biotechnol. 2002, 12, 235–241.Search in Google Scholar

7. Fu, S., Wallner, S., Zenilman, M., Gross, R., Garnett, I., Bluth, M. Sophorolipids and their derivatives are lethal against human pancreatic cancer cells. J. Surg. Res. 2008, 148, 77–82; https://doi.org/10.1016/j.jss.2008.03.005.Search in Google Scholar

8. Hu, Y., Ju, L. Purification of lactonic sophorolipids by crystallization. J. Biotechnol. 2001, 87, 263–272; https://doi.org/10.1016/S0168-1656(01)00248-6.Search in Google Scholar

9. Van Bogaert, I., Fleurackers, S., Van Kerrebroeck, S., Develter, D., Soetaert, W. Production of new to-nature sophorolipids by cultivating the yeast Candida bombicola on unconventional hydrophobic substrates. Biotechnol. Bioeng. 2011, 108, 734–741; https://doi.org/10.1002/bit.23004.Search in Google Scholar

10. Ashby, R., Solaiman, D., Foglia, T. The use of fatty acid esters to enhance free acid sophorolipid synthesis. Biotechnol. Lett. 2006, 28, 253–260; https://doi.org/10.1007/s10529-005-5527-y.Search in Google Scholar

11. Cooper, D., Paddock, D. Production of a biosurfactant from Torulopsis bombicola. Appl. Environ. Microbiol. 1984, 47, 173–176; https://doi.org/10.1128/aem.47.1.173-176.1984.Search in Google Scholar

12. Desai, J., Banat, I. Microbial production of surfactants and their commercial potential. Microbiol. Mol. Biol. Rev. 1997, 61, 47–64; https://doi.org/10.1128/mmbr.61.1.47-64.1997.Search in Google Scholar

13. Hu, Y., Ju, L. Sophorolipids production from different lipid precursors observed with LC–MS. Enzym. Microb. Technol. 2001, 29, 593–601; https://doi.org/10.1016/S0141-0229(01)00439-2.Search in Google Scholar

14. Hirata, Y., Ryu, M., Oda, Y., Igarashi, K., Nagatsuka, A., Furuta, T., Sugiura, M. Novel characteristics of sophorolipids, yeast glycolipid biosurfactants, as biodegradable low-foaming surfactants. J. Biosci. Bioeng. 2009, 108, 142–146; https://doi.org/10.1016/j.jbiosc.2009.03.012.Search in Google Scholar

15. Garcia, O., Casas, J. Unstructured kinetic model for sophorolipid production by Candida bombicola. Enzym. Microb. Technol. 1999, 25, 613–621; https://doi.org/10.1016/S0141-0229(99)00089-7.Search in Google Scholar

16. Goldman, E., Green, L. H., Eds. Practical handbook of microbiology; Taylor and Francis: CRC Press, 2015; p. 17. https://doi.org/10.1201/9781420009330.Search in Google Scholar

17. Asmer, H., Lang, S., Wagner, F., Wray, V. Microbial production, structure elucidation and bioconversion of sophorose lipids. J. Am. Oil Chem. Soc. 1988, 65, 1460–1466; https://doi.org/10.1007/BF02898308.Search in Google Scholar

18. Casas, J., Garcia-Ochoa, F. Sophorolipid production by Candida bombicola: medium composition and culture methods. J. Biosci. Bioeng. 1999, 88, 488–494; https://doi.org/10.1016/S1389-1723(00)87664-1.Search in Google Scholar

19. Wadekar, S., Kale, S., Lali, A., Bhowmik, D., Pratap, A. Sophorolipid production by Starmerella bombicola (ATCC 22214) from virgin and waste frying oils, and the effects of activated earth treatment of the waste oil. J. Am. Oil Chem. Soc. 2012, 89, 1029–1039; https://doi.org/10.1007/s11746-011-1986-6.Search in Google Scholar

20. Oliveria, M., Camilios-Neto, D., Baldo, C., Magri, A., Celligoi, M. Biosynthesis and production of sophorolipids. Int. J. Sci. Tech. Res. 2014, 3, 133–146.Search in Google Scholar

21. Bhangale, A., Patil, S., Wadekar, S., Kale, S., Lali, A., Bhowmick, D., Pratap, D. Stabilization of Foam Produced by Sodium Lauryl Sulphate with Mannosylerythritol Lipids Synthesized on soybean oil and sucrose by Pseudozyma antarctica (ATCC 32657). Tenside Surfactants Deterg. 2013, 50, 131–136; https://doi.org/10.3139/113.110240.Search in Google Scholar

22. Wadekar, S. D., Kale, S. B., Lali, A. M., Bhowmick, D. N., Pratap, A. P. Jatropha oil and karanja oil as carbon sources for production of sophorolipids. Eur. J. Lipid Sci. Technol. 2012, 114, 823–832; https://doi.org/10.1002/ejlt.201100282.Search in Google Scholar

23. Bhangale, A. P., Wadekar, S. D., Kale, S. B., Pratap, A. P. Sophorolipids synthesized using non-traditional oils with glycerol and studies on their surfactant properties with synthetic surfactant. Tenside Surfactants Deterg. 2014, 51, 387–396; https://doi.org/10.3139/113.110320.Search in Google Scholar

24. Mawani, J., Jadhav, J., Pratap, A. Fermentative production of mannosylerythritol lipids using sweetwater as waste substrate by pseudozyma Antarctica (MTCC 2706). Tenside Surfactants Deterg. 2021, 58, 4; https://doi.org/10.1515/tsd-2020-2272.Search in Google Scholar

25. Bajaj, V., Tilay, A., Annapure, U. Enhanced production of bioactive Sophorolipids by Starmerella bombicola NRRL Y-17069 by design of experiment approach with successive purification and characterization. J. Oleo Sci. 2012, 61, 377–386; https://doi.org/10.5650/jos.61.377.Search in Google Scholar PubMed

26. Daverey, A., Pakshirajan, K. Kinetics of growth and enhanced sophorolipids production by Candida bombicola using a low-cost fermentative medium. Appl. Biochem. Biotechnol. 2010, 160, 2090–2101; https://doi.org/10.1007/s12010-009-8797-3.Search in Google Scholar PubMed

27. Davila, A., Marchal, R., Vandecasteele, J. Sophorose lipid production from lipidic precursors: predictive evaluation of industrial substrates. J. Ind. Microbiol. 1994, 13, 249–257; https://doi.org/10.1007/BF01569757.Search in Google Scholar

28. Saerens, K., Van Bogaert, I., 1 Soetaert, W. Characterization of sophorolipid biosynthetic enzymes from Starmerella bombicola. FEMS Yeast Res. 2015, 15; https://doi.org/10.1093/femsyr/fov075.Search in Google Scholar PubMed

29. Shelke, P. B., Mali, S. N., Chaudhari, H. K., Pratap, A. P. Chitosan hydrochloride mediated efficient, green catalysis for the synthesis of perimidine derivatives. J. Heterocycl. Chem. 2019, 56, 3048–3054; https://doi.org/10.1002/jhet.3700.Search in Google Scholar

Received: 2021-03-20
Accepted: 2021-05-22
Published Online: 2022-01-20
Published in Print: 2022-01-27

© 2021 Walter de Gruyter GmbH, Berlin/Boston

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