Abstract
Mannosylerythritol lipids (MELs) are glycolipid biosurfactants produced by Pseudozyma yeasts. They show not only the excellent interfacial properties but also versatile biochemical actions. In the course of MEL production from soybean oil by P. antarctica and P. rugulosa, some new extracellular glycolipids (more hydrophobic than the previously reported di-acylated MELs) were found in the culture medium. The most hydrophobic one was identified as 1-O-alka(e)noyl-4-O-[(4′,6′-di-O-acetyl-2′,3′-di-O-alka(e)noyl)-β-d-mannopyranosyl]-d-erythritol, namely tri-acylated MEL. Others were tri-acylated MELs bearing only one acetyl group. The tri-acylated MEL could be prepared by the lipase-catalyzed esterification of a di-acylated MEL with oleic acid implying that the new glycolipids are synthesized from di-acylated MELs in the culture medium containing the residual fatty acids.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Banat IM, Makkar RS, Cameotra SS (2000) Potential commercial applications of microbial surfactants. Appl Microbiol Biotechnol 53:495–508
Im JH, Ikegami T, Yanagishita H, Takeyama Y, Idemoto Y, Koura N, Kitamoto D (2003) Mannosylerythritol lipids, yeast glycolipid biosurfactants, are potential affinity ligand materials for human immunoglobulin G. J Biomed Mater Res 65:379–385
Imura T, Yanagishita H, Kitamoto D (2004) Coacervate formation from natural glycolipid: one acetyl group on the headgroup triggers coacervate-to-vesicle transition. J Am Chem Soc 126:10804–10805
Imura T, Yanagishita H, Ohira J, Sakai H, Abe M, Kitamoto D (2005) Thermodynamically stable vesicle formation from glycolipid biosurfactant sponge phase. Colloids and Surfaces B: Biointerfaces 43:114–121
Imura T, Ohta N, Inoue K, Yagi H, Negishi H, Yanagishita H, Kitamoto D (2006) Naturally engineered glycolipid biosurfactants leading to distinctive self-assembled structures. Chem Eur J 12:2434–2440
Isoda H, Shinmoto H, Kitamoto D, Matsumura M, Nakahara T (1997) Differentiation of human promyelocytic leukemia cell line HL60 by microbial extracellular glycolipids. Lipids 32:263–271
Kida T, Tanaka T, Nakatsuji Y, Akashi M (2006) Formation of micrometer-sized supramolecular assemblies with unique morphologies from triple-chain lipids with two sugar head groups. Chem Lett 35:112–113
Kitamoto D, Akiba S, Hioki C, Tabuchi T (1990) Extracellular accumulation of mannosylerythritol lipids by a strain of Candida antarctica. Agric Biol Chem 54:31–36
Kitamoto D, Yanagishita H, Shinbo T, Nakane T, Kamisawa C, Nakahara T (1993) Surface active properties and antimicrobial activities of mannosylerythritol lipids as biosurfactants produced by Candida antarctica. J Biotech 29:91–96
Kitamoto D, Ghosh S, Ourisson G, Nakatani Y (2000) Formation of giant vesicles from diacylmannosyleryhtritols, and their binding to concanavalin A. Chem Commun 10:861–862
Kitamoto D, Ikegami T, Suzuki T, Sasaki A, Takeyama Y, Idemoto Y, Koura N, Yanagishita H (2001) Microbial conversion of n-alkanes into glycolipid biosurfactants, mannosylerythritol lipids, by Pseudozyma antarctica. Biotechnol Lett 23:1709–1714
Kitamoto D, Isoda H, Nakahara T (2002) Functions and potential applications of glycolipid biosurfactants –from energy-saving materials to gene delivery carriers–. J Biosci Bioeng 94:187–201
Lang S (2002) Biological amphiphiles (microbial biosurfactants). Curr Opin Colloid Interface Sci 7:12–20
Morita T, Konishi M, Fukuoka T, Imura T, Kitamoto D (2006) Discovery of Pseudozyma rugulosa NBRC 10877 as a novel producer of the glycolipid biosurfactants, mannosylerythritol lipids, based on rDNA sequence. Appl Microbiol Biotechnol 73:305–313
Morita T, Konishi M, Fukuoka T, Imura T, Kitamoto H, Kitamoto D (2007) Physiological differences in the formation of the glycolipid biosurfactants, mannosylerythritol lipids, between Pseudozyma antarctica and Pseudozyma aphidis. Appl Microbiol Biotechnol 74:307–315
Rau U, Nguyen LA, Schulz S, Wray V, Nimtz M, Roper H, Koch H, Lang S (2005) Formation and analysis of mannosylerythritol lipids secreted by Pseudozyma aphidis. Appl Microbial Biotechnol 66:551–559
Rodorigues L, Banat IM, Teixeria J, Oliveira R (2006) Biosurfactants: potential applications in medicine. J Antimicrob Chemothera 57:609–618
Sumida Y, Masuyama A, Takasu M, Kida T, Nakatsuji Y, Ikeda I, Nojima M (2000) Behavior of self-organized molecular assemblies composed of phosphatidylcholines and synthetic triple-chain amphiphiles in water. Langmuir 16:8005–8009
Wakamatsu Y, Zhao X, Jin C, Day N, Shibahara M, Nomura N, Nakahara T, Murata T, Yokoyama KK (2001) Mannosylerythritol lipid induces characteristics of neuronal differentiation in PC12 cells through an ERK-related signal cascade. Eur J Biochem 268:374–383
Zhao X, Murata T, Ohno S, Day N, Song J, Nomura N, Nakahara T, Yokoyama KK (2001) Protein kinase Ca plays a critical role in mannosylerythritol lipid-induced differentiation of melanoma B16 cells. J Biol Chem 276:9903–9910
Acknowledgements
We would like to thank Dr. Tadashi Nemoto of our institute and Dr. Katsuo Asakura of JOEL Ltd. Co., Japan, for their help on NMR measurement. We also wish to thank Ms. Akiko Sugimura, a fellow of the Japan Industrial Technology Association, for her technical assistance. This work was supported by the Industrial Technology Research Grant Program in 05A33008c from the New Energy and Industrial Technology Development Organization (NEDO) of Japan.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Fukuoka, T., Morita, T., Konishi, M. et al. Characterization of new glycolipid biosurfactants, tri-acylated mannosylerythritol lipids, produced by Pseudozyma yeasts. Biotechnol Lett 29, 1111–1118 (2007). https://doi.org/10.1007/s10529-007-9363-0
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10529-007-9363-0