Abstract
Cultivation of Torulopsis bombicola ATCC 22214 on a mixture of glucose and oleic acid (A) or oleic acid alone (B) produced large amounts of sophorose lipids. In the case of A, 38 g/1 of crude product were finally isolated; fermentation B led to 77 g/1. After separation by MPLC and TLC, six glycolipids were obtained and identified by NMR and fast atom bombardment-mass spectrometry (FAB-MS). In general, a 17-hydroxyocta-decanoic acid at the C-1’ -position and acetate groups at the C-6’ -and C-6’ -positions of sophorose were found as substituents in the lactone and acidic forms of these lipids.
The composition of product from A was as follows: 62% of sophorolipid 1’,4’ -lactone 6’ ,6’ -diacetate (SL-1), 4% of sophorolipid 1’,4’-lactone 6’-monoacetate (SL-2), 4% of sophorolipid 1’,4 ’-lactone (SL-3), 4% of sophorolipid 1’,6’-and l’,6’-lactones (SL-4a,b), 4% of sophorolipid 6’-monoacetate acid (SL-5), 4% of sophorolipid acid (SL-6) and finally 17% of other lipids.
In B, the principal lactone (40%) had a double bond in the fatty acid moiety; the other components were identical with the above products. Yields of 13% SL-2 and of 35% lipids containing no carbohydrate were significant. SL-1 was deacetylated to SL-3 (yield: 25-307c) using acetyl-esterase in a two-phase system (cyclohexane/water).
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References
Gorin, P.A.J., J.F.T. Spencer and A.P. Tulloch,Can. J. Chem. 39:846 (1961).
Tulloch, A.P., J.F.T. Spencer and P.A.J. Gorin,Ibid. 40:1326 (1962).
Tulloch, A.P., A. Hill and J.F.T. Spencer,Ibid. 46:3337 (1968).
Tulloch, A.P., and J.F.T. Spencer,J. Org. Chem 32:2868 (1972).
Inoue, S., and S. Ito,Biotechnol Lett. 4:3 (1982).
Cooper, D.G., and D.A. Paddock,Appl Environ. Microbiol. 47:173 (1984).
Göbbert, U., S. Lang and F. Wagner,Biotechnol Lett 6:225 (1984).
Hodge, J.E., and B.T. Hofreiter,Methods in Carbohydrate Chemistry 1:390 (1962).
Kretschmer, A, H. Bock and F. Wagner,Appl. Environ. Microbiol. 44:864 (1982).
Spencer, J.F.T., D.M. Spencer and A.P. Tulloch,Economic Microbiol, edited by A.H. Rose, 1979, pp. 3, 523-540.
Laumen, K., E.H. Reimerdes and M. Schneider,Tetrahedron Lett. 26:407 (1985).
Dropsy, E.P., and A.M. Klibanov,Biotechnol Bioeng. 26:911 (1984).
U.S. Patent 4,533,632.
U.S. Patent 4,414,328.
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Asmer, HJ., Lang, S., Wagner, F. et al. Microbial production, structure elucidation and bioconversion of sophorose lipids. J Am Oil Chem Soc 65, 1460–1466 (1988). https://doi.org/10.1007/BF02898308
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DOI: https://doi.org/10.1007/BF02898308