Petroselinic acid purification and its use for the fermentation of new sophorolipids

AMB Express

Volumn 6, Issue 1, 2016, Pages

  Delbeke, Elisabeth I P ^a   Everaert, Jonas ^a   Uitterhaegen, Evelien ^a,b   Verweire, Stijn ^a   Verlee, Arno ^a   Talou, Thierry ^b   Soetaert, Wim ^a   Van Bogaert, Inge N A ^a   Stevens, Christian V ^a  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITÉ DE TOULOUSE   (France)

Author keywords

Chemical derivatization; Fermentation; Petroselinic acid; Sophorolipid; Starmerella bombicola

Indexed keywords

GLYCOLIPID; LONG CHAIN FATTY ACID; PETROSELINIC ACID; PETROSELINIC ACID 1; SOPHOROLIPID; SOPHOROLIPID METHYL ESTER DERIVATIVE; UNCLASSIFIED DRUG; VEGETABLE OIL;

ARTICLE; CORIANDER; CRITICAL MICELLE CONCENTRATION; FERMENTATION; HYDROLYSIS; SACCHAROMYCETALES; STARMERELLA BOMBICOLA; SURFACE TENSION;

EID: 84962355514     PISSN: None     EISSN: 21910855     Source Type: Journal    
DOI: 10.1186/s13568-016-0199-7     Document Type: Article

References (29)

1. Alaluf S, Hu H-L, Green MR, Powell JR, Rawlings AV, Rogers JS, Watkinson A, Cain FW. Cosmetic use of petroselinic acid. EP. 1999;1(013):178.
2. Baccile N, Babonneau F, Jestin J, Pehau-Arnaudet G, Van Bogaert I. Unusual, pH-induced, self-assembly of sophorolipid biosurfactants. ACS Nano. 2012;6:4763–76. doi:10.1021/nn204911k.
3. Baccile N, Nassif N, Malfatti L, Van Bogaert INA, Soetaert W, Pehau-Arnaudet G, Babonneau F. Sophorolipids: a yeast-derived glycolipid as greener structure directing agents for self-assembled nanomaterials. Green Chem. 2010;12:1564–7. doi:10.1039/C0gc00163e.
4. Baccile N, Pedersen JS, Pehau-Arnaudet G, Van Bogaert INA. Surface charge of acidic sophorolipid micelles: effect of base and time. Soft Matter. 2013;9:4911–22. doi:10.1039/c3sm50160d.
5. Barrett KE, Green MR, Hu H-L, Parmar P, Powell JR, Rawlings AV. Skin care composition. US Pat. 2000;6(455):057.
6. Cahoon EB, Dormann P, Ohlrogge JB. Petroselinic acid biosynthesis and production in transgenic plants. Prog Lipis Res. 1994;33:155–63. doi:10.1016/0163-7827(94)90018-3.
7. Cuvier AS, Babonneau F, Berton J, Stevens CV, Fadda GC, Genois I, Le Griel P, Pehau-Arnaudet G, Baccile N. Synthesis of uniform, monodisperse, sophorolipid twisted ribbons. Chem Asian J. 2015;10:2419–26. doi:10.1002/asia.201500693.
8. Cuvier AS, Berton J, Stevens CV, Fadda GC, Babonneau F, Van Bogaert INA, Soetaert W, Pehau-Arnaudet G, Baccile N. pH-triggered formation of nanoribbons from yeast-derived glycolipid biosurfactants. Soft Matter. 2014;10:3950–9. doi:10.1039/C4sm00111g.
9. Delbeke EIP, Movsisyan M, Van Geem KM, Stevens CV. Chemical and enzymatic modification of sophorolipids. Green Chem. 2016;18:76–104. doi:10.1039/C5GC02187A.
10. Delbeke EIP, Roman BI, Marin GB, Van Geem KM, Stevens CV. A new class of antimicrobial biosurfactants: quaternary ammonium sophorolipids. Green Chem. 2015;17:3373–7. doi:10.1039/c5gc00120j.
11. Dierker M, Schafer HJ. Surfactants from oleic, erucic and petroselinic acid: synthesis and properties. Eur J Lipid Sci Technol. 2010;112:122–36. doi:10.1002/ejlt.200900126.
12. Gupta R, Prabhune AA. Structural determination and chemical esterification of the sophorolipids produced by Candida bombicola grown on glucose and alpha-linolenic acid. Biotechnol Lett. 2012;34:701–7. doi:10.1007/s10529-011-0818-y.
13. Heimerma.Wh, Gordon DT, Kowalysh.De, Jensen RG, Holman RT. Effect of double-bond position in octadecenoates upon hydrolysis by pancreatic lipase. Lipids. 1973;8:45–6. doi:10.1007/Bf02533239.
14. Kasture MB, Patel P, Prabhune AA, Ramana CV, Kulkarni AA, Prasad BLV. Synthesis of silver nanoparticles by sophorolipids: effect of temperature and sophorolipid structure on the size of particles. J Chem Sci. 2008;120:515–20. doi:10.1007/s12039-008-0080-6.
15. Lang S, Brakemeier A, Heckmann R, Spockner S, Rau U. Production of native and modified sophorose lipids. Chim Oggi. 2000;18:76–9.
16. Morya VK, Ahn C, Jeon S, Kim EK. Medicinal and cosmetic potentials of sophorolipids. Mini Rev Med Chem. 2013;13:1761–8. doi:10.2174/13895575113139990002.
17. Placek LL. Review on petroselinic acid and its derivativees. J Am Oil Chem Soc. 1963;40:319–29. doi:10.1007/Bf02631548.
18. Prabhune A, Fox SR, Ratledge C. Transformation of arachidonic acid to 19-hydroxy- and 20-hydroxy-eicosatetraenoic acids using Candida bombicola. Biotechnol Lett. 2002;24:1041–4. doi:10.1023/A:1015662013985.
19. Roelants SLKW, Ciesielska K, De Maeseneire SL, Everaert B, Denon Q, Moens H, Vanlerberghe B, Van Bogaert INA, Van der Meeren P, De Vreese B, Soetaert W. Towards the industrialisation of new biosurfactants: biotechnological opportunities for the lactone esterase gene from Starmerella bombicola. Biotechnol Bioeng. 2015. doi:10.1002/bit.25815.
20. Shah S, Prabhune A. Purification by silica gel chromatography using dialysis tubing and characterization of sophorolipids produced from Candida bombicola grown on glucose and arachidonic acid. Biotechnol Lett. 2007;29:267–72. doi:10.1007/s10529-006-9221-5.
21. Shukla S, Gupta S. Coriander. In: Aggarwal BB, Kunnumakkara AB, editors. Molecular targets and therapeutic uses of spices: modern uses for ancient medicine. Singapore: World Scientific; 2009. p. 149–71.
22. Uitterhaegen E, Nguyen QH, Sampaio KA, Stevens CV, Merah O, Talou T, Rigal L, Evon P. Extraction of coriander oil using twin-screw extrusion: feasibility study and potential press cake applications. J Am Oil Chem Soc. 2015;92:1219–33. doi:10.1007/s11746-015-2678-4.
23. Van Bogaert I, Ciesielska K, Devreese B, Soetaert W, Roelants S. A lactonase derived from Candida bombicola and uses thereof. 2011a
24. 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. 2011a;108:734–41. doi:10.1002/bit.23004.
25. Van Bogaert INA, Sabirova J, Develter D, Soetaert W, Vandamme EJ. Knocking out the MFE-2 gene of Candida bombicola leads to improved medium-chain sophorolipid production. FEMS Yeast Res. 2009;9:610–7. doi:10.1111/j.1567-1364.2009.00501.x.
26. Van Bogaert INA, Saerens K, De Muynck C, Develter D, Soetaert W, Vandamme EJ. Microbial production and application of sophorolipids. Appl Microbiol Biotechnol. 2007;76:23–34. doi:10.1007/s00253-007-0988-7.
27. Van Bogaert INA, Zhang JX, Soetaert W. Microbial synthesis of sophorolipids. Process Biochem. 2011b;46:821–33. doi:10.1016/j.procbio.2011.01.010.
28. Weber N, Richter KD, Schulte E, Mukherjee KD. Petroselinic acid from dietary triacylglycerols reduces the concentration of arachidonic-acid in tissue-lipids of rats. J Nutr. 1995;125:1563–8.
29. Weinkauf R, Santhanam U, Palanker LR, Januario TG, Brinker A. Petroselinic acid as an anti-irritant in compositions containing alpha hydroxy acids. US Pat. 1998;6(022):896.