Sophorolipids (SLs), a prominent member of the biosurfactants family are produced in acidic and/or lactonic form by yeast Starmerella bombicola NRRL Y-17069 when grown on hydrophilic or hydrophobic or both carbon sources. In current study, ricinoleic acid rich castor oil (10%) was used as hydrophobic and glycerol (10%) was used as hydrophilic carbon source. The yields of 24.5 ± 0.25 g/l sophorolipids were analyzed by anthrone and HPLC method which further increased upto 40.24 ± 0.76 g/l sophorolipids using fed batch process at 5L fermenter level. The structures of sophorolipids synthesized on castor oil were elucidated by liquid chromatography-mass spectrometer (LC-MS), (13)C and (1)H NMR. The results indicated that the ricinoleic acid (RA) gets hydroxylated at ω-1 position but incorporated into sophorolipids through already available hydroxyl group at 12(th) position. It resulted in the production of a novel sophorolipids with hydroxyl fatty acid as side chain and has applications as surfactant for novel drug delivery, anti microbial agent, cosmetic ingredient and emulsifier.

sophorolipids, ricinoleic acid, castor oil, Starmerella bombicola (NRRL Y-17069), direct incorporation, ω-1 hydroxylation

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC(=O)OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](COC(C)=O)O[C@H]2OC(C/C=C/CCCCCCCC(=O)O)CCCCC(C)O)[C@H](O)[C@@H](O)[C@@H]1O

722.822 g/mol (C₃₄H₅₈O₁₆)

Sophorolipids (SLs), a prominent member of the biosurfactants family are produced in acidic and/or lactonic form by yeast Starmerella bombicola NRRL Y-17069 when grown on hydrophilic or hydrophobic or both carbon sources. In current study, ricinoleic acid rich castor oil (10%) was used as hydrophobic and glycerol (10%) was used as hydrophilic carbon source. The yields of 24.5 ± 0.25 g/l sophorolipids were analyzed by anthrone and HPLC method which further increased upto 40.24 ± 0.76 g/l sophorolipids using fed batch process at 5L fermenter level. The structures of sophorolipids synthesized on castor oil were elucidated by liquid chromatography-mass spectrometer (LC-MS), (13)C and (1)H NMR. The results indicated that the ricinoleic acid (RA) gets hydroxylated at ω-1 position but incorporated into sophorolipids through already available hydroxyl group at 12(th) position. It resulted in the production of a novel sophorolipids with hydroxyl fatty acid as side chain and has applications as surfactant for novel drug delivery, anti microbial agent, cosmetic ingredient and emulsifier.

sophorolipids, ricinoleic acid, castor oil, Starmerella bombicola (NRRL Y-17069), direct incorporation, ω-1 hydroxylation

1H NMR data:
missing...

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

[*]O[C@@H]1[C@@H](COC(C)=O)O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](COC(C)=O)O[C@H]2OC(C/C=C/CCCCCCCC([*])=O)CCCCC(C)O)[C@H](O)[C@H]1O

704.807 g/mol (C₃₄H₅₆R₂O₁₅, R = next and previous repeats, not counted in mol weight)

Sophorolipids (SLs), a prominent member of the biosurfactants family are produced in acidic and/or lactonic form by yeast Starmerella bombicola NRRL Y-17069 when grown on hydrophilic or hydrophobic or both carbon sources. In current study, ricinoleic acid rich castor oil (10%) was used as hydrophobic and glycerol (10%) was used as hydrophilic carbon source. The yields of 24.5 ± 0.25 g/l sophorolipids were analyzed by anthrone and HPLC method which further increased upto 40.24 ± 0.76 g/l sophorolipids using fed batch process at 5L fermenter level. The structures of sophorolipids synthesized on castor oil were elucidated by liquid chromatography-mass spectrometer (LC-MS), (13)C and (1)H NMR. The results indicated that the ricinoleic acid (RA) gets hydroxylated at ω-1 position but incorporated into sophorolipids through already available hydroxyl group at 12(th) position. It resulted in the production of a novel sophorolipids with hydroxyl fatty acid as side chain and has applications as surfactant for novel drug delivery, anti microbial agent, cosmetic ingredient and emulsifier.

sophorolipids, ricinoleic acid, castor oil, Starmerella bombicola (NRRL Y-17069), direct incorporation, ω-1 hydroxylation

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC(O)CCCCC(C/C=C/CCCCCCCC(=O)O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

638.748 g/mol (C₃₀H₅₄O₁₄)

Sophorolipids (SLs), a prominent member of the biosurfactants family are produced in acidic and/or lactonic form by yeast Starmerella bombicola NRRL Y-17069 when grown on hydrophilic or hydrophobic or both carbon sources. In current study, ricinoleic acid rich castor oil (10%) was used as hydrophobic and glycerol (10%) was used as hydrophilic carbon source. The yields of 24.5 ± 0.25 g/l sophorolipids were analyzed by anthrone and HPLC method which further increased upto 40.24 ± 0.76 g/l sophorolipids using fed batch process at 5L fermenter level. The structures of sophorolipids synthesized on castor oil were elucidated by liquid chromatography-mass spectrometer (LC-MS), (13)C and (1)H NMR. The results indicated that the ricinoleic acid (RA) gets hydroxylated at ω-1 position but incorporated into sophorolipids through already available hydroxyl group at 12(th) position. It resulted in the production of a novel sophorolipids with hydroxyl fatty acid as side chain and has applications as surfactant for novel drug delivery, anti microbial agent, cosmetic ingredient and emulsifier.

sophorolipids, ricinoleic acid, castor oil, Starmerella bombicola (NRRL Y-17069), direct incorporation, ω-1 hydroxylation

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC(=O)OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@H]3COC(=O)CCCCCCC/C=C/CC(CCCCC(C)O)O[C@@H]2O3)[C@H](O)[C@@H](O)[C@@H]1O

662.77 g/mol (C₃₂H₅₄O₁₄)