Startseite Structures and Properties of Sophorolipids in Dependence of Microbial Strain, Lipid Substrate and Post-Modification
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Structures and Properties of Sophorolipids in Dependence of Microbial Strain, Lipid Substrate and Post-Modification

  • Timo Bollmann , Christian Zerhusen , Birgit Glüsen und Ulrich Schörken
Veröffentlicht/Copyright: 1. Oktober 2019
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Abstract

Starmerella bombicola and Candida kuoi are known to secrete structurally divergent sophorolipid type glycolipids (SLs) under nitrogen limitation. In the present work SLs were produced in titers of 3.9–78.6 g L−1 with the two yeast strains utilizing stearic, oleic and linoleic acid as substrates. HPLC-ELSD combined with HPLC-MS and NMR spectroscopy was used for qualitative and quantitative analysis of the SL mixtures. While S. bombicola almost exclusively produced lactonic diacetylated SLs with a preference for subterminal fatty acid hydroxylation, C. kuoi synthesized diacetylated, terminally hydroxylated open chain SLs with up to 25% of dimeric and trimeric products. Surface tension measurements showed a higher surface and interface activity of the lactonic products from S. bombicola in comparison to open chain C. kuoi based SLs. The lowest CMC of 5.4 mg L−1 and minimum surface tension at the CMC of 35.9 mN m−1 were obtained for the stearic acid based lactones. Similar tendencies were observed in interfacial tension analysis with 3.6 mN m−1 for oleic acid based lactonic SLs at the interface water/paraffin oil in comparison to 9.4 mN m−1 for the corresponding open-chain SL. The acidic C. kuoi SL mixtures directly exhibited foaming properties whereas the S. bombicola SLs needed alkaline deacetylation and ring opening to display foaming comparable to that of the structurally related alkyl polyglycosides.

Kurzfassung

Starmerella bombicola und Candida kuoi sekretieren strukturell divergente Glycolipide mit Sophorolipid-(SL)-Struktur unter Stickstofflimitierung. In der vorliegenden Arbeit wurden Sophorolipide mit zwei Hefestämmen und Stearin-, Öl- und Linolsäure als Substrate in Ausbeuten von 3.9–78.6 g L−1 hergestellt. HPLC-ELSD-Quantifizierung in Kombination mit HPLC-MS und NMR-Spektroskopie wurde zur Analyse der SL-Mischungen eingesetzt. S. bombicola produzierte bevorzugt subterminal hydroxylierte, lactonische Sophorolipide, während C. kuoi offenkettige Sophorolipide mit terminal hydroxylierten Fettsäuren und einem Anteil an dimeren und trimeren Produkten von bis zu 25% synthetisierte. Oberflächenspannungsmessungen in Wasser zeigten niedrigere Werte für die lactonischen Produkte aus S. bombicola im Vergleich zu den offenkettigen C. kuoi-SLs. Die niedrigsten Werte für CMC und Oberflächenspannung von 5.4 mg L−1 und 35.9 mN m−1 wurden für die Stearinsäure-basierten Lactone erhalten. Ähnliche Tendenzen zeigten sich bei Untersuchungen an der Grenzfläche Wasser/Paraffinöl mit 3.6 mN m−1 für die Lactone auf Ölsäurebasis und 9.4 mN m−1 für die korrespondierenden offenkettigen SL. Die sauren C. kuoi-SL-Mischungen zeigten sofort Schaumbildung, wohingegen die S. bombicola-SLs erst nach alkalischer Deacetylierung und Ringöffnung ein zu den strukturell verwandten Alkylpolyglykosiden vergleichbares Schaumvermögen aufwiesen.

Key words: Sophorolipids; Starmerella bombicola; Candida kuoi; surface tension; interfacial tension
Stichwörter: Sophorolipide; Starmerella bombicola; Candida kuoi; Oberflächenspannung; Grenzflächenspannung
∗Correspondence address, Prof. Dr. Ulrich Schörken, TH Köln – Campus Leverkusen, Faculty of Applied Natural Sciences, CHEMPARK E39, Kaiser-Wilhelm-Allee, 51368 Leverkusen Germany, Tel.: 0049-214-32831-4610, E-Mail:

Prof. Dr. Ulrich Schörken studied chemistry at the University of Cologne and did his Ph.D. at the Institute of Biotechnology IBT1 of the Scientific Research Centre Jülich (FZ Jülich) under the supervision of Prof. Sahm. After one year of post-doctoral research at FZ Jülich he started his industrial career in 1998 in the enzyme engineering group of company Henkel AG & Co. KGaA in Düsseldorf, Germany. In 2000, he joined the oleochemical company Cognis GmbH (now part of BASF AG), where he established the lipid biotechnology research group and worked as senior scientist in different research positions. In 2010, he got an appointment as Professor for Biotechnology & Green Chemistry at the newly founded Campus Leverkusen of TH Köln. His research focuses on lipid biotechnology, amphiphilic molecules, utilization of renewable resources and application of biocatalysts and microorganisms for the production of bio-based chemicals. Prof. Schörken is a member of the Euro Fed Lipid and the NRW Cluster of Industrial Biotechnology CLIB 2021. In total he holds more than 60 publications and patents.

Prof. Dr. Birgit Glüsen studied chemistry at the Universities of Münster and Marburg and obtained her PhD in Physical Chemistry. She worked as a Post-Doc in Gothenburg (Sweden) and as a Feodor-Lynen fellow of the Alexander-von-Humboldt Foundation at Cormell University, Itaca, NY. In 1999 she joined Henkel AG & Co KGaA in Düsseldorf to work in different positions in research and development especially for laundry and home care products. In 2013 Birgit Glüsen was appointed Professor for Physical Chemistry at the TH Köln. Her research interests are focused on interface science and in the interaction of polymers with surfactants and small molecules in bulk, solution and at interfaces. Birgit Glüsen is currently the chairwoman of the GDCh Division “Detergent Chemistry”.

Timo Bollmann received his B.Sc. in Technical Chemistry and M.Sc. in Applied Chemistry from the TH Köln – Faculty of Applied Natural Sciences. He did his Master thesis at TH Köln in the group of Ulrich Schörken. Since 2017 he is PhD student in the group of Birgit Glüsen.

Christian Zerhusen received his M.Sc. in Molecular and Applied Biotechnology from the RWTH Aachen University, Germany (2016) – specialization in Industrial Biotechnology and Biochemical Engineering. Currently works as a Ph.D student in the group of Prof. Schörken. Main research topics are microbial biosurfactants and bioprocess development.

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Received: 2019-06-10
Accepted: 2019-07-16
Published Online: 2019-10-01
Published in Print: 2019-09-16

© 2019, Carl Hanser Publisher, Munich

Artikel in diesem Heft

  1. Contents/Inhalt
  2. Contents
  3. Microbial Synthesis
  4. Production of Non-Toxic Biosurfactant – Surfactin – Through Microbial Fermentation of Biomass Hydrolysates for Industrial and Environmental Applications
  5. Characterisation Novel Biosurfactants
  6. Structures and Properties of Sophorolipids in Dependence of Microbial Strain, Lipid Substrate and Post-Modification
  7. Personal Care/Cleansing
  8. Amino-Acid Surfactants in Personal Cleansing (Review)
  9. Toward Milder Personal Care Cleansing Products: Fast ex vivo Screening of Irritating Effects of Surfactants on Skin Using Raman Microscopy
  10. Textile Surface Modification
  11. Surface Characterization of Textiles for Optimization of Functional Polymeric Nano-Capsule Attachment
  12. Enhanced Oil Recovery and Oil-Spill Dispersants
  13. Pseudo-Gemini Biosurfactants with CO2 Switchability for Enhanced Oil Recovery (EOR)
  14. Hydrophilic-Lipophilic-Difference (HLD) Guided Formulation of Oil Spill Dispersants with Biobased Surfactants
  15. Mineral Processing
  16. Floatability of Chalcopyrite by Glycolipid Biosurfactants as Compared to Traditional Thiol Surfactants
  17. Antimicrobial Properties
  18. Stability of Emulsions and Nanoemulsions Stabilized with Biosurfactants, and their Antimicrobial Performance against Escherichia coli O157:H7 and Listeria monocytogenes
https://doi.org/10.3139/113.110640
Schlagwörter für diesen Artikel
Sophorolipids; Starmerella bombicola; Candida kuoi; surface tension; interfacial tension

Artikel in diesem Heft

  1. Contents/Inhalt
  2. Contents
  3. Microbial Synthesis
  4. Production of Non-Toxic Biosurfactant – Surfactin – Through Microbial Fermentation of Biomass Hydrolysates for Industrial and Environmental Applications
  5. Characterisation Novel Biosurfactants
  6. Structures and Properties of Sophorolipids in Dependence of Microbial Strain, Lipid Substrate and Post-Modification
  7. Personal Care/Cleansing
  8. Amino-Acid Surfactants in Personal Cleansing (Review)
  9. Toward Milder Personal Care Cleansing Products: Fast ex vivo Screening of Irritating Effects of Surfactants on Skin Using Raman Microscopy
  10. Textile Surface Modification
  11. Surface Characterization of Textiles for Optimization of Functional Polymeric Nano-Capsule Attachment
  12. Enhanced Oil Recovery and Oil-Spill Dispersants
  13. Pseudo-Gemini Biosurfactants with CO2 Switchability for Enhanced Oil Recovery (EOR)
  14. Hydrophilic-Lipophilic-Difference (HLD) Guided Formulation of Oil Spill Dispersants with Biobased Surfactants
  15. Mineral Processing
  16. Floatability of Chalcopyrite by Glycolipid Biosurfactants as Compared to Traditional Thiol Surfactants
  17. Antimicrobial Properties
  18. Stability of Emulsions and Nanoemulsions Stabilized with Biosurfactants, and their Antimicrobial Performance against Escherichia coli O157:H7 and Listeria monocytogenes
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