Mannosylerythritol lipids: A review

Journal of Industrial Microbiology and Biotechnology

Volumn 35, Issue 12, 2008, Pages 1559-1570

  Arutchelvi, Joseph Irudayaraj ^a   Bhaduri, Sumit ^b   Uppara, Parasu Veera ^b   Doble, Mukesh ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

^b RELIANCE INDUSTRIES LIMITED   (India)

Author keywords

Glycolipid; Immunoglobulins; Mannosylerythritol lipids; Pseudozyma yeasts; Self assembled structures

Indexed keywords

GLYCOLIPID; GLYCOPROTEIN; MANNOSYLERYTHRITOL; MICROBIAL ENZYME; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; BIOSYNTHESIS; CANDIDA; CELL DIFFERENTIATION; DRUG STRUCTURE; ENZYME STRUCTURE; FUNGUS; GENE DELIVERY SYSTEM; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; KURTZMANOMYCES; LIQUID CRYSTAL; MICROBIAL DIVERSITY; MICROORGANISM; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROTEIN PURIFICATION; PSEUDOZYMA ANTARCTICA; PSEUDOZYMA APHIDIS; PSEUDOZYMA FUSIFORMATA; PSEUDOZYMA GRAMINICOLA; PSEUDOZYMA HUBEIENSIS; PSEUDOZYMA PARANTARCTICA; PSEUDOZYMA RUGULOSA; PSEUDOZYMA SHAXIENSIS; PSEUDOZYMA SIAMENSIS; PSEUDOZYMA TSUKUBAENSIS; REGULATORY MECHANISM; REVIEW; SCHIZONELLA MELANOGRAMMA; USTILAGO; USTILAGO MAYDIS; USTILAGO NUDA;

GLYCOLIPIDS; MOLECULAR CONFORMATION; SURFACE-ACTIVE AGENTS; USTILAGINALES;

PSEUDOZYMA; USTILAGO;

EID: 55949106365     PISSN: 13675435     EISSN: 14765535     Source Type: Journal    
DOI: 10.1007/s10295-008-0460-4     Document Type: Review

References (73)

1. SS Bhattacharjee RH Haskins PAJ Gorin 1970 Location of acyl groups on two partly acylated glycolipids from strains of Ustilago (smut fungi) Carbohydr Res 13 235 246 10.1016/S0008-6215(00)80830-7
2. B Boothroyd JA Thorn RH Haskins 1956 Biochemistry of the ustilaginales. XII. Characterization of extracellular glycolipids produced by Ustilago sp Can J Biochem Physiol 34 10 14
3. SS Cameotra RS Makkar 2004 Recent applications of biosurfactants as biological and immunological molecules Curr Opin Microbiol 7 262 266 10.1016/j.mib.2004.04.006
4. ME Davey NC Caiazza GA OToole 2003 Rhamnolipid surfactant production affects biofilm architecture in Pseudomonas aeruginosa PAO1 J Bacteriol 185 1027 1036 10.1128/JB.185.3.1027-1036.2003
5. G Deml T Anke F Oberwinkler BM Gianetti W Steglich 1980 Schizonellin A and B, new glycolipids from Schizonella melanogramma Phytochemistry 19 83 87 10.1016/0031-9422(80)85018-7
6. JD Desai IM Banat 1997 Microbial production of surfactants and their commercial potential Microbiol Mol Biol Rev 61 47 64
7. E Deziel F Lepine S Milot R Villemur 2003 rhlA is required for the production of a novel biosurfactant promoting swarming motility in Pseudomonas aeruginosa: 3-(3-hydroyalkanoyloxy)alkanoic acids (HAAs), the precursors of rhamnolipids Microbiology 149 2005 2013 10.1099/mic.0.26154-0
8. AL Fluharty JS O'Brien 1969 A mannose- and erythritol-containing glycolipid from Ustilago maydis Biochemistry 8 2627 2632 10.1021/bi00834a056
9. T Fukuoka T Morita M Konishi T Imura D Kitamoto 2007 Characterization of new glycolipid biosurfactants, tri-acylated mannosylerythritol lipids, produced by Pseudozyma yeasts Biotechnol Lett 29 1111 1118 10.1007/s10529-007-9363-0
10. T Fukuoka T Morita M Konishi T Imura D Kitamoto 2007 Characterisation of new types of mannosylerythritol lipids as biosurfactants produced from soybean oil by a Basidiomycetes yeast, Pseudozyma shanxiensis J Oleo Sci 56 435 442
11. T Fukuoka T Morita M Konishi T Imura H Sakai D Kitamoto 2007 Structural characterization and surface-active properties of a new glycolipid biosurfactant, mono-acylated mannosylerythritol lipid, produced from glucose by Pseudozyma antarctica Appl Microbiol Biotechnol 76 801 810 10.1007/s00253-007- 1051-4
12. T Fukuoka T Morita M Konishi T Imura D Kitamoto 2008 A basidiomycetous yeast, Pseudozyma tsukubaensis, efficiently produces a novel glycolipid biosurfactant. The identification of a new diastereomer of mannosylerythritol lipid-B Carbohydr Res 343 555 560
13. JDV Hamme A Singh OP Ward 2006 Physiological aspects Part 1 in a series of papers devoted to surfactants in microbiology and biotechnology Biotechnol Adv 24 604 620 10.1016/j.biotechadv.2006.08.001
14. RH Haskins JA Thorn B Boothroyd 1955 Biochemistry of the ustilagenales. XI. Metabolic products of Ustilago zeae in submerged culture Can J Microbiol 1 749 756
15. Im JH, Nakane T, Yanagishita H, Ikegami T, Kitamoto D (2001) Mannosylerythritol lipid, a yeast extracellular glycolipid, shows high binding affinity towards human immunoglobulin G. BMC Biotechnol 1:5. http://www.biomedcentral.com/1472-6750/1/5. doi: 10.1186/1472-6750-1-5
16. JH Im H Yanagishita T Ikegami Y Takeyama Y Idemoto N Koura 2003 Mannosylerythritol lipids, yeast glycolipid biosurfactants, are potential affinity ligand materials for human immunoglobulin G J Biomed Mater Res 65A 379 385 10.1002/jbm.a.10491
17. T Imura H Yanagishita D Kitamoto 2004 Coacervate formation from natural glycolipid: one acetyl group on the headgroup triggers coacervate-to-vesicle transition J Am Chem Soc 126 10804 10805 10.1021/ja0400281
18. T Imura H Yanagishita J Ohira H Sakai M Abeb D Kitamoto 2005 Thermodynamically stable vesicle formation from glycolipid biosurfactant sponge phase Colloids Surf B Biointerfaces 43 115 121 10.1016/j.colsurfb.2005.03.015
19. T Imura N Ohta K Inoue N Yagi H Negishi H Yanagishita 2006 Naturally engineered glycolipid biosurfactants leading to distinctive self-assembled structures Chem Eur J 12 2434 2440 10.1002/chem.200501199
20. T Imura Y Hikosaka W Worakitkanchanakul H Sakai M Abe M Konishi 2007 Aqueous-phase behavior of natural glycolipid biosurfactant mannosylerythritol lipid A: sponge, cubic, and lamellar phases Langmuir 23 1659 1663 10.1021/la0620814
21. T Imura S Ito R Azumi H Yanagishita H Sakai M Abe 2007 Monolayers assembled from a glycolipid biosurfactant from Pseudozyma (Candida) antarctica serve as a high-affinity ligand system for immunoglobulin G and M Biotechnol Lett 29 865 870 10.1007/s10529-007-9335-4
22. H Inaba 2000 New challenge in advanced thermal energy transportation using functionally thermal fluids Int J Therm Sci 39 991 1003 10.1016/S1290-0729(00)01191-1
23. Y Inoh D Kitamoto N Hirashima M Nakanishi 2001 Biosurfactants of MEL-A increase gene transfection mediated by cationic liposomes Biochem Biophys Res Commun 289 57 61 10.1006/bbrc.2001.5930
24. Y Inoh D Kitamoto N Hirashima M Nakanishi 2004 Biosurfactant MEL-A dramatically increases gene transfection via membrane fusion J Control Release 94 423 431 10.1016/j.jconrel.2003.10.020
25. H Isoda D Kitamoto H Shinmoto M Matsumura T Nakahara 1997 Microbial extracellular glycolipid induction of differentiation and inhibition of the protein kinase C activity of human promyelocytic leukemia cell line HL60 Biosci Biotechnol Biochem 61 609 614
26. H Isoda H Shinmoto D Kitamoto M Matsumura T Nakahara 1997 Differentiation of human promyelocytic leukemia cell line HL60 by microbial extracellular glycolipids Lipids 32 263 271 10.1007/s11745-997-0033-0
27. H Isoda T Nakahara 1997 Mannosylerythritol lipid induces granulocytic differentiation and inhibits the tyrosine phosphorylation of human myelogenous leukemia cell line K562 Cytotechnology 25 191 195 10.1023/A:1007982909932
28. K Kakugawa M Tamai K Imamura K Miyamoto S Miyoshi Y Morinaga 2002 Isolation of yeast Kurtzmanomyces sp. I-11, novel producer of mannosylerythritol lipid Biosci Biotechnol Biochem 66 188 191 10.1271/bbb.66.188
29. H Kawashima T Nakahara M Oogaki T Tabuchi 1983 Extracellular production of a mannosylerythritol lipid by a mutant of Candida sp. from n-alkanes and triacylglycerols J Ferment Technol 61 143 149
30. DB Kearns R Losick 2003 Swarming motility in undomesticated Bacillus subtilis Mol Microbiol 49 581 590 10.1046/j.1365-2958.2003.03584.x
31. H-S Kim BD Yoon DH Choung HM Oh T Katsuragi Y Tani 1999 Characterization of a biosurfactant, mannosylerythritol lipid produced from Candida sp SY16 Appl Microbiol Biotechnol 52 713 721 10.1007/s002530051583
32. H-S Kim J-W Jeon B-H Kim C-Y Ahn H-M Oh B-D Yoon 2006 Extracellular production of a glycolipid biosurfactant, mannosylerythritol lipid, by Candida sp. SY16 using fed-batch fermentation Appl Microbiol Biotechnol 70 391 396 10.1007/s00253-005-0092-9
33. D Kitamoto S Akiba C Hioki T Tabuchi 1990 Extracellular accumulation of mannosylerythritol lipids by a strain of Candida antarctica Agric Biol Chem 54 31 36
34. D Kitamoto K Haneishi T Nakahara T Tabuchi 1990 Production of mannosylerythritol lipids by Candida antarctica from vegetable oils Agric Biol Chem 54 37 40
35. D Kitamoto T Fuzishiro H Yanagishita T Nakane T Nakahara 1992 Production of mannosylerythritol lipids as biosurfactants by resting cells of Candida antarctica Biotechnol Lett 14 305 310 10.1007/BF01022329
36. D Kitamoto T Nemoto H Yanagishita T Nakane H Kitamoto T Nakahara 1993 Fatty acid metabolism of mannosylerythritol lipids as biosurfactants produced by Candida antarctica J Jpn Oil Chem Soc 42 346 358
37. D Kitamoto H Yanagishita T Shinbo T Nakane C Kamisawa T Nakahara 1993 Surface active properties and antimicrobial activities of mannosylerythritol lipids as biosurfactants produced by Candida antarctica J Biotechnol 29 91 96 10.1016/0168-1656(93)90042-L
38. D Kitamoto H Yanagishita K Hayara HK Kltamoto 1998 Contribution of a chain-shortening pathway to the biosynthesis of the fatty acids of mannosyierythritol lipid (biosurfactant) in the yeast Candida antarctica: effect of β-oxidation inhibitors on biosurfactant synthesis Biotechnol Lett 20 813 818 10.1023/A:1005347022247
39. D Kitamoto SGO Ghosh Y Nakatani 2000 Formation of giant vesicle from diacylmannosylerythritols and their binding to concanavalin A Chem Commun 2000 861 862 10.1039/b000968g
40. D Kitamoto T Ikegami GT Suzuki A Sasaki Y Takeyama Y Idemoto 2001 Microbial conversion of n-alkanes into glycolipid biosurfactants, mannosylerythritol lipids, by Pseudozyma (Candida antarctica) Biotechnol Lett 23 1709 1714 10.1023/A:1012464717259
41. D Kitamoto H Yanagishita A Endo M Nakaiwa M Nakane T Akiya 2001 Remarkable antiagglomeration effect of a yeast biosurfactant, diacylmannosylerythritol, on ice-water slurry for cold thermal storage Biotechnol Prog 17 362 365 10.1021/bp000159f
42. D Kitamoto H Isoda T Nakahara 2002 Functions and potential applications of glycolipid biosurfactants-from energy-saving materials to gene delivery carriers J Biosci Bioeng 94 187 201 10.1263/jbb.94.187
43. D Kitamoto 2008 Naturally engineered glycolipid biosurfactants leading to distinctive self-assembling properties Yakugaku Zasshi 128 695 706 10.1248/yakushi.128.695
44. M Konishi T Imura T Fukuoka T Morita D Kitamoto 2007 A yeast glycolipid biosurfactant, mannosylerythritol lipid, shows high binding affinity towards lectins on a self-assembled monolayer system Biotechnol Lett 29 473 480 10.1007/s10529-006-9261-x
45. M Konishi T Morita T Fukuoka T Imura K Kakugawa D Kitamoto 2007 Production of different types of mannosylerythritol lipids as biosurfactants by the newly isolated yeast strains belonging to the genus Pseudozyma Appl Microbiol Biotechnol 75 521 531 10.1007/s00253-007-0853-8
46. M Konishi T Morita T Fukuoka T Imura K Kakugawa D Kitamoto 2008 Efficient production of mannosylerythritol lipids with high hydrophilicity by Pseudozyma hubeiensis KM-59 Appl Microbiol Biotechnol 78 37 46 10.1007/s00253-007-1292-2
47. T Matsuyama Y Nakagawa 1996 Bacterial wetting agents working incolonization of bacteria on surface environments Colloids Surf B Biointerfaces 7 207 214 10.1016/0927-7765(96)01300-8
48. T Morita M Konishi T Fukuoka T Imura D Kitamoto 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 10.1007/s00253-006-0466-7
49. T Morita M Konishi T Fukuoka T Imura HK Kitamoto D Kitamoto 2007 Characterization of the genus Pseudozyma by the formation of glycolipid biosurfactants, mannosylerythritol lipids FEMS Yeast Res 7 286 292 10.1111/j.1567-1364.2006.00154.x
50. T Morita M Konishi T Fukuoka T Imura S Yamamoto M Kitagawa 2008 Identification of Pseudozyma graminicola CBS 10092 as a producer of glycolipid biosurfactants, mannosylerythritol lipids J Oleo Sci 57 123 131
51. T Morita M Konishi T Fukuoka T Imura D Kitamoto 2008 Production of glycolipid biosurfactants, mannosylerythritol lipids, by Pseudozyma siamensis CBS 9960 and their interfacial properties J Biosci Bioeng 105 493 502 10.1263/jbb.105.493
52. CN Mulligan 2005 Environmental applications for biosurfactants Environ Pollut 133 183 198 10.1016/j.envpol.2004.06.009
53. TR Neu 1996 Significance of bacterial surface-active compounds in interaction of bacteria with interfaces Microbiol Rev 60 151 166
54. U Rau LA Nguyen S Schulz V Wray M Nimtz H Roeper 2005 Formation and analysis of mannosylerythritol lipids secreted by Pseudozyma aphidis Appl Microbiol Biotechnol 66 551 5593 10.1007/s00253-004-1672-9
55. U Rau LA Nguyen H Roeper H Koch S Lang 2005 Fed-batch bioreactor production of mannosylerythritol lipids secreted by Pseudozyma aphidis Appl Microbiol Biotechnol 68 607 613 10.1007/s00253-005-1906-5
56. U Rau LA Nguyen H Roeper H Koch S Lang 2005 Downstream processing of mannosylerythritol lipids produced by Pseudozyma aphidis Eur J Lipid Sci Technol 107 373 380 10.1002/ejlt.200401122
57. L Rodrigues IM Banat J Teixeira R Oliveira 2006 Biosurfactants: potential applications in medicine J Antimicrob Chemother 57 609 618 10.1093/jac/dkl024
58. EZ Ron E Rosenberg 2001 Natural roles of biosurfactants Environ Microbiol 3 229 236 10.1046/j.1462-2920.2001.00190.x
59. E Rosenberg EZ Ron 1999 High- and low-molecular-mass microbial surfactants Appl Microbiol Biotechnol 52 154 162 10.1007/s002530051502
60. M Shibahara X Zhao Y Wakamatsu N Nomura T Nakahara C Jin 2000 Mannosylerythritol lipid increases levels of galactoceramide in and neurite outgrowth from PC12 pheochromocytoma cells Cytotechnology 33 247 251 10.1023/A:1008155111024
61. A Singh JD Van Hamme OP Ward 2007 Surfactants in microbiology and biotechnology. Part 2. Application aspects Biotechnol Adv 25 99 121 10.1016/j.biotechadv.2006.10.004
62. P Singh SS Cameotra 2004 Potential applications of microbial surfactants in biomedical sciences Trends Biotechnol 22 142 146 10.1016/j.tibtech.2004.01. 010
63. S Spoeckner V Wray M Nimtz S Lang 1999 Glycolipids of the smut fungus Ustilago maydis from cultivation on renewable resources Appl Microbiol Biotechnol 51 33 39 10.1007/s002530051359
64. Tanaka A, Fukui S (1989) Metabolism of n-alkane. In: The yeast, vol 3, 2nd edn. Academic Press, London, p 261-287
65. Y Ueno N Hirashima Y Inoh T Furuno M Nakanishi 2007 Characterization of biosurfactant-containing liposomes and their efficiency for gene transfection Biol Pharm Bull 30 169 172 10.1248/bpb.30.169
66. Y Ueno Y Inoh T Furuno N Hirashima D Kitamoto M Nakanishi 2007 NBD-conjugated biosurfactant (MEL-A) shows a new pathway for transfection J Control Release 123 247 253 10.1016/j.jconrel.2007.08.012
67. Vertesy L, Kurz M, Wink J, Noelken G (2002) Ustilipides, method for the production and the use thereof. US Patent 6,472,158
68. Y Wakamatsu X Zhao C Jin N Day M Shibahara N Nomura 2001 Mannosylerythritol lipid induces characteristics of neuronal differentiation in PC12 cells through an ERK-related signal cascade Eur J Biochem 268 374 383 10.1046/j.1432-1033.2001.01887.x
69. RJA Wander P Vreken S Ferdiandusse GA Jansen HR Waterham CWT van Roermunde 2001 Peroxisomal fatty acid α- and β-oxida tion in humans: enzymology, peroxisomal metabolite transporters and peroxisomal diseases Biochem Soc Trans 29 250 267 10.1042/BST0290250
70. Worakitkanchanakula W, Imurab T, Fukuokab T, Moritab T, Sakaia H, Abea M et al. (2008) Aqueous-phase behavior and vesicle formation of natural glycolipid biosurfactant, mannosylerythritol lipid-B. Colloids Surf B Biointerfaces. doi: 10.1016/j.colsurfb.2008.03.009
71. X Zhao Y Wakamatsu M Shibahara N Nomura C Geltinger T Nakahara 1999 Mannosylerythritol lipid is a potent inducer of apoptosis and differentiation of mouse melanoma cells in culture Cancer Res 59 482 486
72. X Zhao X Geltinger S Kishikawa S Ohshima S Murata S Nomura 2000 Treatment of mouse melanoma cells with phorbol 12-myristate 13-acetate counteracts mannosylerythritollipid-induced growth arrest and apoptosis Cytotechnology 33 123 130 10.1023/A:1008129616127
73. α plays a critical role in mannosylerythritol lipid-induced differentiation of melanoma B16 Cells J Biol Chem 276 39903 39910 10.1074/jbc.M010281200