Astonishing diversity of natural surfactants: 1. Glycosides of fatty acids and alcohols

Lipids

Volumn 39, Issue 10, 2004, Pages 933-953

  Dembitsky, Valery M ^a,b  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; FATTY ACIDS; LABORATORIES; MOLECULAR STRUCTURE;

CHEMICAL STRUCTURES; COSMETICS; FOOD INDUSTRY; GLYCOSIDES;

SURFACE ACTIVE AGENTS;

BIOSURFACTANT; BUTYROLACTONE; ELECTROLYTE; FATTY ACID; FATTY ALCOHOL; GLYCOLIPID; GLYCOSIDE; RHAMNOLIPID; SOPHOROLIPID; SORBITAN ESTER; SURFACTANT; TREHALOSE; UNCLASSIFIED DRUG;

ADSORPTION; BACTERIUM; BIOLOGICAL ACTIVITY; CHEMICAL STRUCTURE; FRUIT; FUNGUS; INVERTEBRATE; MICROEMULSION; NONHUMAN; PLANT LEAF; PLANT ROOT; PLANT SEED; REVIEW;

BIOLOGICAL FACTORS; GLYCOLIPIDS; SUGAR ALCOHOLS; SURFACE-ACTIVE AGENTS;

BACTERIA (MICROORGANISMS); FUNGI; INVERTEBRATA;

EID: 11844303432     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-004-1316-1     Document Type: Review

References (182)

1. Dembitsky, V.M. (2004) Chemistry and Biodiversity of Biologically Active Natural Glycosides, Chem. Biodiver. 1, 673-781.
2. Clayton, W. (1943) Theory of Emulsions, p. 127, McGraw-Hill, New York.
3. Griffin, W.C. (1949) Classification of Surface-Active Agents by "HLB," J. Soc. Cosmet. Chem. 1, 311-324.
4. Griffin, W.C. (1954) Calculation of HLB Values of Non-Ionic Surfactants, J. Soc. Cosmet. Chem. 5, 259-267.
5. Ikan, R. (ed.) (1999) Naturally Occurring Glycosides, John Wiley & Sons, Chichester, England.
6. Ernst, B., Hart, G.W., and Sinaÿ, P. (eds.) (2000) Carbohydrates in Chemistry and Biology, Wiley-VCH, Weinheim.
7. Levy, D.E., and Tang, C. (1995). Chemistry of C-Glycosides, Elsevier, Amsterdam.
8. Kates, M. (ed.) (1990) Glycolipids, Phosphoglycolipids and Sulfoglycolipids. Handbook of Lipid Research, Kluwer Academic/Plenum Publishers, New York.
9. Harborne, J.B., and Williams, C.A. (2001) Anthocyanins and Other Flavonoids, Nat. Prod. Rep. 18, 310-333.
10. Harborne, J.B. (1993) Flavonoids: Advances in Research Since 1986, CRC Press, Boca Raton, Florida.
11. Esko, J., Marth, J., Cummings, R., Freeze, H., Varki, A., and Hart, G. (eds.) (1999) Essentials of Glycobiology, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York.
12. Frank, H.A., Young, A.J., Britton, G., and Cogdell, R.J. (eds.) (1999) The Photochemistry of Carotenoids. Kluwer Academic Publishers, Dordrecht.
13. Kosaric, N. (1993) Biosurfactants: Production, Properties, Applications, Marcel Dekker, New York.
14. (a) Holmberg, K. (2001) Natural Surfactants, Curr. Opin. Colloid Interface Sci. 6, 148-159;
15. (b) Tyman, J.H.P. (ed.) (1992) Surfactants in Lipid Chemistry: Recent Synthetic, Physical, and Biodegradative Studies, Royal Society of Chemistry, London.
16. Satoshi, O. (ed.) (2002) Macrolide Antibiotics: Chemistry, Biology, and Practice, Academic Press, Amsterdam, Boston.
17. Rosen, M.J. (2004) Surfactants and Interfacial Phenomena, 3rd edn., p. 464, John Wiley & Sons, New York.
18. Van der Meer, M.T.J., Schouten, S., Hanada, S., Hopmans, E.C., Sinninghe Damsté, J.S., and Ward, D.M. (2002) Alkane-1,2-diol-Based Glycosides and Fatty Glycosides and Wax Esters in Roseiflexus castenholzii and Hot Spring Microbial Mats, Arch. Microbiol. 178, 229-237.
19. Rezanka, T. (2002) Glycosides of Polyenoic Branched Fatty Acids from Myxomycetes, Phytochemistry 60, 639-646.
20. Jude, A.R., Little, J.M., Freeman, J.P., Evans, J.E., Radominska-Pandya, A., and Grant, D.F. (2000) Linoleic Acid Diols Are Novel Substrates for Human UDP-Glucuronosyltransferases, Arch. Biochem. Biophys. 380, 294-302.
21. Řezanka, T., and Dembitsky, V.M. (2003) Brominated Oxylipins and Oxylipin Glycosides from Red Sea Corals, Eur. J. Org. Chem. 14, 309-316.
22. Simko, I., Omer, E.A., Ewing, E.E., McMurry, S., Koch, J.L., and Davies, P.J. (1996) Tuberonic (12-OH-jasmonic) Acid Glucoside and Its Methyl Ester in Potato, Phytochemistry 43, 727-730.
23. Matsuura, H., Yoshira, T., Ichihara, A., Kikuta, Y., and Koda, Y. (1993) Tuber-forming Substances in Jerusalem Artichoke (Helianthus tuberosus L.), Biosci. Biotech. Biochem. 57, 1253-1256.
24. Matsuura, H., Yoshihara, T., and Ichihara, A. (1993) 4 New Polyacetylenic Glucosides, Methyl β-D-Glucopyranosyl Helianthenate C-F, from Jerusalem Artichoke (Helianthus tuberosus L.), Biosci. Biotechnol. Biochem. 57, 1492-1498.
25. Wang, M., Likuzaki, H., Zhu, N., Sang, N., Nakatani, N., and Ho, C.T. (2000) Isolation and Structural Elucidation of Two New Glycosides from Sage (Salvia officinalis L.), J. Agric. Food Chem. 48, 235-238.
26. MacLeod, J.K., Rasmussen, H.B., and Wills, A.C. (1997) A New Glycoside Antimicrobial Agent from Persoonia linearis x pinifolia, J. Nat. Prod. 60, 620-622.
27. Takeda, Y., Takechi, A., Masuda, T., and Otsuka, H. (1998) An Acyclic Monoterpene Glucosyl Ester from Lantana lilacia, Planta Med. 64, 78-79.
28. Yoshikawa, K., Satou, Y., Tokunaga, Y., Tanaka, M., Arihara, S., and Nigam, S.K. (1998) Four Acylated Triterpenoid Saponins from Albizia procera, J. Nat. Prod. 61, 440-445.
29. Krajewaski, D., Duque, C., and Schreier, P. (1997) Aliphatic β-D-Glucosides from Fruits of Carica pubescens, Phytochemistry 45, 1627-1631.
30. Stermitz, F.R., Cashman, K.K., Halligan, K.M., Morel, C., Tegos, G.P., and Lewis, K. (2003) Polyacylated Neohesperidosides from Geranium caespitosum: Bacterial Multidrug Resistance Pump Inhibitors, Bioorg. Med. Chem. Lett. 13, 1915-1918.
31. Boros, C., Katz, B., Mitchell, S., Pearce, C., Swinbank, K., and Taylor, D. (2002) Emmyguyacins A and B: Unusual Glycolipids from a Sterile Fungus Species That Inhibit the Low-pH Conformational Change of Hemagglutinin A During Replication of Influenza Virus, J. Nat. Prod. 65, 108-114.
32. King, R.R., and Calhoun, L.A. (1988) 2,3-Di-O- and 1,2,3-Tri-O-Acylated Glucose Esters from the Glandular Trichomes of Datura metel, Phytochemistry 27, 3761-3763.
33. King, R.R., Colhoun, L.A., Singh, P.R., and Boucher, A. (1993) Characterization of 2,3,4,3′-Tetra-O-acylated Sucrose Esters Associated with the Glandular Trichomes of Lycopersicon typicum, J. Agric. Food Chem. 41, 469-473.
34. Severson, R.F., Arrendale, R.F., Chortyk, O.T., Green, C.R., Thome, F.A., Stewart, J.L., and Johnson, A.W. (1985) Isolation and Characterization of the Sucrose Esters of the Cuticular Waxes of Green Tobacco Leaf, J. Agric. Food Chem. 33, 870-875.
35. Arrendale, R.F., Severson, R.F., Sisson, V.A., Costello, C.E., Leary, J.A., Himmelsbach, D.S., and Van Halbeek, H. (1990) Characterization of the Sucrose Esters from Nicotiana glutinosa, J. Agric. Food Chem. 38, 75-85.
36. Matsuzaki, T., Shinozaki, Y., Hagimori, M., Tobita, T., Shigematsu, H., and Koiwai, A. (1992) Novel Glycerolipids and Glycolipids from the Surface Lipids of Nicotiana benthamiana, Biosci. Biotech. Biochem. 56, 1565-1569.
37. Ohya, I., Shinozaki, Y., Tobita, T., Takahashi, H., Matsuzaki, T., and Koiwai, A. (1994) Sucrose Esters from the Surface Lipids of Nicotiana cavicola, Phytochemistry 37, 143-145.
38. King, R.R., Singh, R.P., and Calhoun, L.A. (1988) Elucidation of Structures for a Unique Class of 2,3,4,3′-Tetra-O-acylated Sucrose Esters from the Type B Glandular Trichomes of Solanum neocardenusii Hawkes and Hjerting (PI 498129), Carbohydr. Res. 173, 235-241.
39. Kandra, L., and Wagner, G.J. (1988) Studies of the Site and Mode of Biosynthesis of Tobacco Trichome Exudate Components, Arch. Biochem. Biophys. 265, 425-432.
40. Matsuzaki, T., Koseki, K., and Koiwai, A. (1988) Germination and Growth-Inhibition of Surface Lipids from Nicotiana Species and Identification of Sucrose Esters, Agric. Biol. Chem. 52, 1889-1897.
41. Ohya, I., Shinozaki, Y., Tobita, T., Takahashi, H., and Matsuzaki, T. (1996) Sucrose Esters from the Surface Lipids of Petunia hybrida, Phytochemistry 41, 787-789.
42. King, R.R., Calhoun, L.A., Singh, R.P., and Boucher, A. (1990) Sucrose Esters Associated with Glandular Trichomes of Wild Lycopersicon Species, Phytochemistry 29, 2115-2118.
43. King, R.R., Pelletier, Y., Singh, R.P., and Calhoun, L.A. (1986) 3,4-Di-O-isobutyryl-6-O-Caprylsucrose: The Major Component of a Novel Sucrose Ester Complex from the Type B Glandular Trichomes of Solanum berthaultii Hawkes (PI 473340), J. Chem. Soc. Chem. Commun., 1078-1079.
44. King, R.R., Singh, R.P., and Boucher, A. (1987) Variation in Sucrose Esters from the Type B Glandular Trichomes of Certain Wild Potato Species, Am. Potato J. 64, 529-534.
45. King, R.R., Singh, R.P., and Calhoun, L.A. (1987) Isolation and Characterization of 3,3′,4,6-Tetra-O-acylated Sucrose Esters from the Type B Glandular Trichomes of Solanum berthaultii Hawkes (PI 265857), Carbohydr. Res. 166, 113-121.
46. King, R.R., Singh, R.P., and Calhoun, L.A. (1988) Elucidation of Structures for a Unique Class of 2,3,4,3′-Tetra-O-acylated Sucrose Esters from the Type B Glandular Trichomes of Solanum neocardenusii Hawkes and Hjerting (PI 498129), Carbohydr. Res. 173, 235-241.
47. Matsuzaki, T., Shinozaki, Y., Suhara, S., Tobita, T., Shigematsu, H., and Koiwai, A. (1991) Leaf Surface Glycolipids from Nicotiana acuminata and Nicotiana pauciflora, Agric. Biol. Chem. 55, 1417-1419.
48. King, R.R., and Calhoun, L.A. (1988) 3,4-Di-O- and 2,3,4-Tri-O-acylated Glucose Esters from the Glandular Trichomes of Nontuberous Solanum species, Phytochemistry 27, 3765-3768.
49. Burke, B.A., Goldsby, G., and Mudd, J.B. (1987) Polar Epicuticular Lipids of Lycopersicon pennellii, Phytochemistry 26, 2567-2571.
50. Hill, K., and Rhode, O. (1999) Sugar-Based Surfactants for Consumer Products and Technical Applications, FETT/Lipid 101, 25-33.
51. Akoh, C.C., and Swanson, B.G. (1994) Carbohydrate Polyesters as Fat Substitutes, Marcel Dekker, New York.
52. Kobayashi, J., Doi, Y., and Ishibashi, M. (1994) Shimofuridin-A, a Nucleoside Derivative Embracing an Acylfucopyranoside Unit Isolated from the Okinawan Marine Tunicate Aplidium multiplicatum, J. Org. Chem. 59, 255-257.
53. Doi, Y., Ishibashi, M., and Kobayashi, J. (1994) Isolation and Structure of Shimofuridins B-G from the Okinawan Marine Tunicate Aplidium multiplicatum, Tetrahedron 50, 8651-8656.
54. Riva, S. (2002) Enzymatic Modification of the Sugar Moieties of Natural Glycosides, J. Mol. Catal. B Enzymol. 19, 43-54.
55. Lang, S., and Wullbrandt, D. (1999) Rhamnose Lipids - Biosynthesis, Microbial Production and Application Potential, Appl. Microbiol. Biotechnol. 51, 22-32.
56. Rosenberg, E., and Ron, E.Z. (1999) High- and Low-Molecular Mass Microbial Surfactants, Appl. Microbiol. Biotechnol. 52, 154-162.
57. Mailer, R.M., and Soberon-Chavez, G. (2000) Pseudomonas aeruginosa Rhamnolipids: Biosynthesis and Potential Applications, Appl. Microbiol. Biotechnol. 54, 625-633.
58. Lang, S. (2002) Biological Amphiphiles (Microbial Biosurfactants), Curr. Opin. Colloid Interf. Sci. 7, 12-20.
59. Ron, E.Z., and Rosenberg, E. (2002) Biosurfactants and Oil Bioremediation, Curr. Opin. Biotechnol. 13, 249-252.
60. Bergstrom, S., Theorell, H., and Davide, H. (1946) On a Metabolic Product of Ps. pyocyanea, Pyolipic Acid, Active Against Myobacteria tuberculosis, Ark. Kem. Mineral Geol. 23A, 1-12.
61. Jarvis, F.G., and Johnson, M.J. (1949) A Glyco-Lipide Produced by Pseudomonas aeruginosa, J. Am. Chem. Soc. 71, 4124-4126.
62. Edwards, J.R., and Hayashi, J.A. (1965) Structure of a Rhamnolipid from Pseudomonas aeruginosa, Arch. Biochem. Biophys. 111, 415-421.
63. Hisatsuka, K., Nakahara, T., Sano, N., and Yamada, K. (1971) Formation of Rhamnolipid by Pseudomonas aeruginosa and Its Function in Hydrocarbon Fermentation, Agric. Biol. Chem. 35, 686-692.
64. Itoh, S., Honda, H., Tomita, F., and Suzuki, T. (1971) Rhamnolipids Produced by Pseudomonas aeruginosa Grown on n-Paraffin, J. Antibiot. (Tokyo) 24, 855-859.
65. Yamaguchi, M., Sato, A., and Yukuyama, A. (1976) Microbial Production of Sugar-Lipids, Chem. Ind. 4, 741-742.
66. Hirayama, T., and Kato, I. (1982) Novel Methyl Rhamnolipids from Pseudomonas aeruginosa, FEBS Lett. 139, 81-85.
67. Syldatk, C., Lang, S., Wagner, F., Wray, V., and Witte, L. (1985) Chemical and Physical Characterization of Four Interfacial-Active Rhamnolipids from Pseudomonas Species DSM 2874 Grown on n-Alkanes, Z. Naturforsch. 40, 51-60.
68. Syldatk, C., Lang, S., Matulovic, U., and Wagner, F. (1985) Production of Four Interfacial Active Rhamnolipids from n-Alkanes or Glycerol by Resting Cells of Pseudomonas Species DSM 2874, Z. Naturforsch. 40, 61-67.
69. Rendell, N.B., Taylor, G.W., Somerville, M., Todd, H., Wilson, R., and Cole, J. (1990) Characterization of Pseudomonas Rhamnolipids, Biochim. Biophys. Acta 1045, 189-193.
70. Abalos, A., Pinazo, A., Infante, M.R., Casals, M., Garcýa, F., and Manresa, A. (2001) Physicochemical and Antimicrobial Properties of New Rhamnolipids Produced by Pseudomonas aeruginosa AT10 from Soybean Oil Refinery Wastes, Langmuir 17, 1367-1371.
71. Kitamoto, D., Yanagishita, H., Haraya, K., and Kitamoto, H.K. (1998) Contribution of a Chain-Shortening Pathway to the Biosynthesis of the Fatty Acids of Mannosylerythritol Lipid (Biosurfactant) in the Yeast Candida antarctica: Effect of β-Oxidation Inhibitors on Biosurfactant Synthesis, Biotechnol. Lett. 20, 813-818.
72. Kitamoto, D., Sangita, G., Ourisson, G., and Nakatani, Y. (2000) Formation of Giant Vesicles from Diacylmannosylerythritols, and Their Binding to Concanavalin A, Chem. Commun., 861-862.
73. Wakamatsu, Y., Zhao, X., Jin, C., Day, N., Shibahara, M., Nomura, N., Nakahara, T., Murata, T., and Yokoyama, K.K. (2001) Mannosylerythritol Lipid Induces Characteristics of Neuronal Differentiation in PC12 Cells Through an ERK-Related Signal Cascade, Eur. J. Biochem. 268, 374-383.
74. Zhao, X., Wakamatsu, Y., Shibahara, M., Nomura, N., Geltinger, C., Nakahara, T., Murata, T., and Yokoyama, K.K. (1999) Mannosylerythritol Lipid Is a Potent Inducer of Apoptosis and Differentiation of Mouse Melanoma Cells in Culture, Cancer Res. 59, 482-486.
75. Kitamoto, D., Yanagishita, H., Endo, A., Nakaiwa, M., Nakane, T., and Akiya, T. (2001) Remarkable Antiagglomeration Effect of a Yeast Biosurfactant, Diacylmannosylerythritol, on Ice-Water Slurry for Cold Thermal Storage, Biotechnol. Prog. 17, 362-365.
76. Cameotra, S.S., and Makkar, R.S. (2004) Recent Applications of Biosurfactants as Biological and Immunological Molecules, Curr. Opin. Microbiol. 7, 262-266.
77. (a) Kitamoto, D., Ikegami, T., Suzuki, G.T., Sasaki, A., Takeyama, Y.I., Idemoto, Y., Koura, N., and Yanagishita, H. (2001) Microbial Conversion of n-Alkanes into Glycolipid Biosurfactants, Mannosylerythritol Lipids by Pseudozyma (Candida antarctica), Biotechnol. Lett. 23, 1709-1714;
78. (b) Umehara, K., Nemoto, K., Ohkubo, T., Miyase, T., Degawa, M., and Noguchi, H. (2004) Isolation of a New 15-Membered Macrocyclic Glycolipid Lactone, Cuscutic Resinoside A from the Seeds of Cuscuta chinensis: A Stimulator of Breast Cancer Cell Proliferation, Planta Med. 70, 299-304.
79. Asselineau, C., and Asselineau, J. (1978) Trehalose-Containing Glycolipids, Prog. Chem. Fats Other Lipids 16, 59-99.
80. Vilkas, E., and Rojas, A. (1964) On the Lipids of Mycobacterium fortuitum, Bull. Soc. Chim. Biol. 46, 689-701.
81. (a) Azuma, I., and Yamamura, Y.J. (1962) Studies on the Firmly Bound Lipids of Human Tubercle bacillus. I. Isolation of Arabinose Mycolate, Biochemistry (Tokyo) 52, 200-206;
82. (b) Vilkas, E., Adam, A., and Senn, M. (1968) Isolation of a New Type of Trehalose Diester from Mycobacterium fortuitum, Chem. Phys. Lipids 2, 11-16.
83. (a) Prottey, C., and Ballou, C.E. (1968) Diacyl Myoinositol Monomannoside from Propionibacterium shermanii, J. Biol. Chem. 243, 6196-6201;
84. (b) Shaw, N., and Dinglinger, F. (1969) The Structure of an Acylated Inositol Mannoside in the Lipids of Propionic Acid Bacteria, Biochem. J. 112, 769-775.
85. Noll, H., Bloch, H., Asselineau, J., and Lederer, E. (1956) The Chemical Structure of the Cord Factor of Mycobacterium tuberculosis, Biochim. Biophys. Acta 20, 299-309.
86. Asselieau, J., and Lederer, E. (1955) Constitution of the Cord Factor Isolated from a Human Strain of Mycobacterium tuberculosis, Biochim. Biophys. Acta 17, 161-168.
87. Asselineau, C., Montrozier, H., Prome, J.C., Savagnac, A., and Welby, M. (1972) Polyunsaturated Glycolipids Synthesized by Mycobacterium phlei, Eur. J. Biochem. 28, 102-109.
88. Goren, M.B. (1970) Sulfolipid I of Mycobacterium tuberculosis, Strain H37Rv: I. Purification and Properties, Biochim. Biophys. Acta 210, 116-126.
89. Goren, M.B. (1970) Sulfolipid I of Mycobacterium tuberculosis, Strain H37Rv: II. Structural Studies, Biochim. Biophys. Acta 210, 127-138.
90. Esch, S.W., Morton, M.D., Williams, T.D., and Buller, C.S. (1999) A Novel Trisaccharide Glycolipid Biosurfactant Containing Trehalose Bears Ester-Linked Hexanoate, Succinate, and Acyloxyacyl Moieties: NMR and MS Characterization of the Underivatized Structure, Carbohydr. Res. 319, 112-123.
91. Mayorga, H., Duqur, C., Knapp, H., and Winterhalter, P. (2002) Hydroxyester Disaccharides from Fruits of Cape Gooseberry (Physalis peruviana), Phytochemistry 59, 439-445.
92. Mayorga, H., Knapp, H., Winterhalter, P., and Duque, C. (2001) Glycosidically Bound Flavor Compounds of Cape Gooseberry (Physalis peruviana L.), J. Agric. Food Chem. 49, 1904-1908.
93. Batrakov, S.G., Konova, I.V., Sheichenko, V.I., and Galanina, L.A. (2003) Glycolipids of the Filamentous Fungus Absidia corymbifera F-295, Chem. Phys. Lipids 123, 157-164.
94. Tulloch, A.P. (1964) The Component Fatty Acids of Oils Found in Spores of Plant Rusts and Other Fungi. IV, Can. J. Microbiol. 10, 359-364.
95. Davila, A.M., Marchai, R., Monin, N., and Vandecasteele, J.P. (1993) Identification and Determination of Individual Sophorolipids in Fermentation Products by Gradient Elution High-Performance Liquid Chromatography with Evaporative Light-Scattering Detection, J. Chromatogr. 648, 139-149.
96. Tulloch, A.P., and Spencer, J.F. (1972) Formation of a Long-Chain Alcohol Ester of Hydroxy Fatty Acid Sophoroside by Fermentation of Fatty Alcohol by a Torulopis Species, J. Org. Chem. 37, 2868-2870.
97. Spencer, J.F., Gorin, P.A., and Tulloch, A.P. (1970) Torulopsis bombicola sp. N, Antonie Van Leeuwenhoek. 36, 129-133.
98. Rau, U., Hammen, S., Heckmann, R., Wray, V., and Lang, S. (2001) Sophorolipids: A Source for Novel Compounds, Ind. Crops Prod. 13, 85-92.
99. Hommel, R.K., Weber, L., Weiss, A., Himelreich, U., Rilke, O., and Kleber, H.P. (1994) Production of Sophorose Lipid by Candida (Torulopsis) apicola Grown on Glucose, J. Biotechnol. 33, 147-155.
100. Weber, L., Stach, J., Haufe, G., Hommel, R., and Kleber, H.-P. (1990) Structure Elucidation of an Unusual Glycolipid by Two-Dimensional N.M.R. Methods, J. Mol. Struct. 219, 353-358.
101. Cooper, D.G. (1986) Biosurfactants, Microbiol. Sci. 3, 145-149.
102. Otto, R.T., Daniel, H.J., Pekin, G., Muller-Decker, K., Furstenberger, G., Reuss, M., and Syldatk, C. (1999) Production of Sophorolipids from Whey. II. Product Composition, Surface Active Properties, Cytotoxicity and Stability Against Hydrolases by Enzymatic Treatment, Appl. Microbiol. Biotechnol. 52, 495-501.
103. Desai, J.D., and Banat, I.M. (1997) Microbial Production of Surfactants and Their Commercial Potential, Microbiol. Mol. Biol. Rev. 61, 47-64.
104. Vollbrecht, E., Rau, U., and Lang, S. (1999) Microbial Conversion of Vegetable Oils into Surface-Active Di-, Tri-, and Tetrasaccharide Lipids (Biosurfactants) by the Bacterial Strain Tsukamurella spec., Fett/Lipid 101, 389-394.
105. Levand, O., and Larson, H. (1979) Some Chemical Constituents of Morinda citrifolia, Plant Med. 36, 186-187.
106. Hirazumi, A., Furusawa, E., Chou, S.C., and Hokama, Y. (1994) Anticancer Activity of Morinda citrifolia (noni) on Intraperitoneally Implanted Lewis Lung Carcinoma in Syngeneic Mice, Proc. West. Pharmacol. Soc. 37, 145-146.
107. Hirazumi, A., Furusawa, E., Chou, S.C., and Hokama, Y. (1996) Immunomodulation Contributes to the Anticancer Activity of Morinda citrifolia (noni) Fruit Juice, Proc. West. Pharmacol. Soc. 39, 7-9.
108. Wang, M., Kikuzaki, H., Jin, Y., Nakatani, N., Zhu, N., Csisar, K., Boyd, C., Rosen, R., Ghal, G., and Ho, C.T. (2000) Novel Glycosides from Noni (Morinda citrifolia), J. Nat. Prod. 63, 1182-1183.
109. Lee, J., and Hollingsworth, R.I. (1996) Isolation and Characterization of a β-1-O-Acyl-β-1,2-diglucosyl Glycoside from the Membranes of a Gram Positive Bacterium Sarcina ventriculi, Tetrahedron 52, 3873-3878.
110. Perda-Miranda, R., and Hernandez-Carlos, B. (2002) HPLC Isolation and Structural Elucidation of Diastereomeric Niloyl Ester Tetrasaccharides from Mexican Scammony Root, Tetrahedron 58, 3145-3154.
111. Gasper, E.M.M. (1999) New Pentasaccharide Macrolactone from the European Convolvulaceae Calystegia soldanella, Tetrahedron Lett. 40, 6861-6864.
112. Font Quer, P. (1962) Plantas Medicinales, Labor, S.A. (ed.), El Dioscorides Renovado, Madrid, p. 543.
113. MacLeod, J.K., Ward, A., and Oelrichs, P.B. (1997) Structural Investigation of Resin Glycosides from Ipomoea lonchophylla, J. Nat. Prod. 60, 467-471.
114. Heacock, R.A. (1975) Psychotomimetics of the Convolvulaceae, Prog. Med. Chem. 11, 91-118.
115. Bieber, L.W., Da Silva, F., Correa Lima, R.M.O., De Andrade Chiappeta, A., Do Naschimento, S.C., De Souza, I.A., De Mello, J.F., and Veith, H.J. (1986) Anticancer and Antimicrobial Glycosides from Ipomoea bahiensis, Phytochemistry 25, 1077-1081.
116. Du, X.M., Sun, N.S., Nishi, M., Lawasaki, T., Guo, Y.T., and Miyahara, K. (1999) Components of the Ether-Insoluble Resin Glycoside Fraction from the Seed of Cuscuta australis, J. Nat. Prod. 62, 722-723.
117. Noda, N., Takahashi, N., Miyahara, K., and Yang, C.R. (1998) Stoloniferins VIII-XII, Resin Glycosides, from Ipomoea stolonifera, Phytochemistry 48, 837-841.
118. MacLeod, J.K., and Ward, A. (1997) Structural Investigation of Resin Glycosides from Ipomoea lonchophylla, J. Nat. Prod. 60, 467-471.
119. Barnes, C.C., Smalley, M.K., Manfredi, K.P., Kindscher, K., Loring, H., and Sheeley, D.M. (2003) Characterization of an Anti-Tuberculosis Resin Glycoside from the Prairie Medicinal Plant Ipomoea leptophylla, J. Nat. Prod. 66, 1457-1462.
120. Rezanka, T., and Guschina, I.A. (2001) Glycoside Esters from Lichens of Central Asia, Phytochemistry 58, 509-516.
121. Rezanka, T., and Guschina, I.A. (2000) Glycosidic Compounds of Murolic, Protoconstipatic and Allo-murolic Acids from Lichens of Central Asia, Phytochemistry 54, 635-645.
122. Vulfson, E.N. (1992) Enzymatic Synthesis of Surfactans, in Tyman, J.H.P. (ed.), Surfactants in Lipid Chemistry: Recent Synthetic, Physical, and Biodegradative Studies, Royal Society of Chemistry, London, pp. 17-37.
123. Kikuchi, H., Saito, Y., Komiya, J., Takaya, Y., Honma, S., Nakahata, N., Ito, A., and Oshima, Y. (2001) Furanodictine A and B: Amino Sugar Analogues Produced by Cellular Slime Mold Dictyostelium discoideum Showing Neuronal Differentiation Activity, J. Org. Chem. 66, 6982-6987.
124. Milkereit, G., Morr, M., Thiem, J., and Vill, V. (2004) Thermotropic and Lyotropic Properties of Long Chain Alkyl Glycopyranosides: Part III: pH-Sensitive Headgroups, Chem. Phys. Lipids 127, 47-63.
125. Gradzielski, M. (2004) Vesicle Gels - Phase Behaviour and Process of Formation, Curr. Opin. Colloid Interface Sci. 9, 149-153.
126. Platz, G., Polike, J., and Thunig, C. (1995) Phase Behavior, Lyotropic Phases, and Flow Properties of Alkyl Glycosides in Aqueous Solution, Langmuir 11, 4250-4255.
127. Hoffmann, B., and Platz, G. (2001) Phase and Aggregation Behaviour of Alkylglycosides, Curr. Opin. Colloid Interface Sci. 6, 171-177.
128. Kaneko, T., Ohtani, K., Kasai, R., Yamasaki, K., and Duc, N.M. (1998) n-Alkyl Glycosides and p-Hydroxybenzoyloxy Glucose from Fruits of Crescentia cujete, Phytochemistry 47, 259-263.
129. Boulanger, R., and Crouzet, J. (2001) Identification of the Aroma Components of Acerola (Malphigia glabra L.): Free and Bound Flavour Compounds, Food Chem. 74, 209-216.
130. Milos, M., Mastelic, J., and Jerkovic, I. (2000) Chemical Composition and Antioxidant Effect of Glycosidically Bound Volatile Compounds from Oregano (Origanum vulgare L. ssp. hirtum), Food Chem. 71, 79-83.
131. De Rosa, S., De Giulio, A., and Tommonaro, G. (1996) Aliphatic and Aromatic Glycosides from the Cell Cultures of Lycopersicon esculentum, Phytochemistry 42, 1031-1034.
132. Takayanagi, T., Ishikawa, T., and Kitajima, J. (2003) Sesquiterpene Lactone Glucosides and Alkyl Glycosides from the Fruit of Cumin, Phytochemistry 63, 479-484.
133. Ono, M., Yoshida, A., Ito, Y., and Nohara, T. (1999) Phenethyl Alcohol Glycosides and Isopentenol Glycoside from Fruit of Bupleurum falcatum, Phytochemistry 51, 819-823.
134. Çalis, I., and Kirmizibekmez, H. (2004) Glycosides from Phlomis lunariifolia, Phytochemistry 65, 2619-2625.
135. Tanahashi, T., Shimada, A., Kai, M., Nagakura, N., Inoue, K., and Chen, C.C. (1996) An Iridoid Glucoside from Jasminum hemsleyi, J. Nat. Prod. 59, 798-800.
136. Messanga, B.B., fon Kimbu, S., Sondengam, B.L., and Bodo, B. (2001) Two New Fatty Acid Glucosides from the Root Bark of Ochna calodendron, Fitoterapia 72, 732-736.
137. Simko, I., Omer, E.A., Ewing, E.E., McMurry, S., Koch, J.L., and Davies, P.J. (1996) Tuberonic (12-OH-jasmonic) Acid Glucoside and Its Methyl Ester in Potato, Phytochemistry 43, 727-730.
138. Gambacorta, A., Soriente, A., Trincone, A., and Sodano, G. (1995) Biosynthesis of the Heterocyst Glycolipids in the Cyanobacterium Anabaena cylindrica, Phytochemistry 39, 771-774.
139. Lambein, F., and Wolk, C.P. (1973) Structural Studies on the Glycolipids from the Envelope of the Heterocyst of Anabaena cylindrica, Biochemistry 12, 791-798.
140. Adams, D.G., and Duggan, P.S. (1999) Tansley Review No. 107. Heterocyst and Akinete Differentiation in Cyanobacteria, New Phytol. 144, 3-33.
141. Soriente, A., Bisogno, T., Gambacorta, A., Romano, I., Sili, C., Trincone, A., and Sodano, G. (1995) Reinvestigation of Heterocyst Glycolipids from the Cyanobacterium, Anabaena cylindrica, Phytochemistry 38, 641-645.
142. Voutquenne, L., Lavaud, C., Massiot, G., Sevenet, T., and Hadi, H.A. (1999) Cytotoxic Polyisoprenes and Glycosides of Long-Chain Fatty Alcohols from Dimocarpus fumatus, Phytochemistry 50, 63-69.
143. Linington, R.G., Robertson, M., Gauthier, A., Finlay, B.B., van Soes, R., and Andersen, R.J. (2002) Caminoside A, an Antimicrobial Glycolipid Isolated from the Marine Sponge Caminus sphaeroconia, Org. Lett. 4, 4089-4092.
144. Wu, J., Zhang, S., Xiao, Q., Li, Q., Huang, J., Long, L., and Huang, L. (2003) Phenylethanoid and Aliphatic Alcohol Glycosides from Acanthus ilicifolius, Phytochemistry 63, 491-495.
145. Babu, B.H., Shylesh, B.S., and Padikkala, J. (2001) Antioxidant and Hepatoprotective Effect of Acanthus ilicifolius, Fitoterapia 72, 272-277.
146. Babu, B.H., Shylesh, B.S., and Padikkala, J. (2002) Tumour Reducing and Anticarcinogenic Activity of Acanthus ilicifolius in Mice, J. Ethnopharmacol. 79, 27-33.
147. Kanchanapoom, T., Kasai, R., Picheansoonthon, C., and Yamasaki, K. (2001) Megastigmane, Aliphatic Alcohol and Benzoxazinoid Glycosides from Acanthus ebracteatus, Phytochemistry 55, 811-817.
148. Wu, J., Zhang, S., Huang, J., Xiao, Q., Li, Q., Long, L., and Huang, L. (2003) New Aliphatic Alcohol and (Z)-4-Coumaric Acid Glycosides from Acanthus ilicifolius, Chem. Pharm. Bull. 51, 1201-1203.
149. Kanchanapoom, T., Ruchirawat, S., Kasai, R., and Otsuka, H. (2004) Aliphatic Alcohol and Iridoid Glycosides from Asystasia intrusa, Chem. Pharm. Bull. 52, 980-982.
150. Yamamura, S., Ozawa, K., Ohtani, K., Kasai, R., and Yamasaki, K. (1998) Antihistaminic Flavones and Aliphatic Glycosides from Mentha spicata, Phytochemistry 48, 131-136.
151. Kanchanapoom, T., Kasai, R., and Yamasaki, K. (2001) Iridoid Glucosides from Barleria lupulina, Phytochemistry 58, 337-341.
152. Costantino, V., Fattorusso, E., Mangoni, A., Di Rosa, M., and Ianaro, A. (1999) Glycolipids from Sponges: VII. Simplexides, Novel Immunosuppressive Glycolipids from the Caribbean Sponge Plakortis simplex, Bioorg. Med. Chem. Lett. 9, 271-276.
153. Gunstone, F.D., Harwood, J.L., and Padley, F.B. (1994) The Lipid Handbook, pp. 39-54, Chapman & Hall, London.
154. Costantino, V., Fattorusso, E., and Mangoni, A. (2000) Glycolipids from Sponges. Part 9: Plakoside C and D, Two Further Prenylated Glycosphingolipids from the Marine Sponge Ectyoplasia ferox, Tetrahedron 56, 5953-5957
155. Costantino, V., Fattorusso, E., Imperatore, C., and Mangoni, A. (2001) Plaxyloside from the Marine Sponge Plakortis simplex: An Improved Strategy for NMR Structural Studies of Carbohydrate Chains, Eur. J. Org. Chem. 23, 4457-4462.
156. Rezanka, T., and Dvoráková, R. (2003) Polypropionate Lactones of Deoxysugars Glycosides from Slime Mold, Lycogala epidendrum, Phytochemistry 63, 945-952.
157. Tabata, N., Ohyama, Y., Tomoda, H., Abe, T., Namikoshi, M., and Omura, S. (1999) Structure Elucidation of Roselipins, Inhibitors of Diacylglycerol Acyltransferase Produced by Gliocladium roseum KF-1040, J. Antibiot. 52, 815-822.
158. Tomoda, H., Ohyama, Y., Abe, T., Tabata, N., Namikoshi, M., Yamaguchi, Y., Masuma, R., and Omura, S. (1999) Roselipins, Inhibitors of Diacylglycerol Acyltransferase Produced by Gliocladium roseum KF-1040. Production, Isolation and Biological Properties, J. Antibiot. 52, 689-704.
159. Tabata, N., Ohyama, Y., Tomoda, H., Abe, T., Namikoshi, M., and Omura, S. (1999) Structure Elucidation of Roselipins, Inhibitors of Diacylglycerol Acyltransferase Produced by Gliocladium roseum KF-1040, J. Antibiot. 52, 815-826.
160. Liu, H., Orjala, J., Rali, T., and Sticher, O. (1998) Glycosides from Stenochlaena palustris, Phytochemistry 49, 2403-2408.
161. Thomas, B.V., Schreiber, A.A., and Weisskopf, C.P. (1988) Simple Method for Quantitation of Capsaicinoids in Pepper Using Capillary Gas Chromatography, J. Agric. Food Chem. 46, 2655-2663.
162. Iorizzi, M., Lanzotti, V., De Marino, S., Zollo, F., Blanco-Molina, M., Macho, A., and Munoz, E. (2001) New Glycosides from Capsicum annuum L. var. acuminatum. Isolation, Structure Determination, and Biological Activity, J. Agric. Food Chem. 49, 2022-2029.
163. Izumitani, Y., Yahara, S., and Nohara, T. (1990) Novel Acyclic Diterpene Glycosides, Capsianosides-A-F and Capsianosides-I-V from Capsicum Plants - Solanaceous Studies, Chem. Pharm. Bull. 38, 1299-1307.
164. Yahara, S., Kobayashi, N., Izumitani, Y., and Nohara, T. (1991) Studies on the Solanaceous Plants: 23. New Acyclic Diterpene Glycosides, Capsianoside-VI, Capsianoside-G and Capsianoside-H from the Leaves and Stems of Capsicum annuum L., Chem. Pharm. Bull. 39, 3258-3260.
165. Shimizu, M. (1999) Modulation of Intestinal Functions by Food Substances, Nahrung/Food 43, 154-158.
166. Kim, Y.C., and Kingston, D.G.I. (1996) A New Caprylic Alcohol Glycoside from Circaea lutetiana ssp. canadensis, J. Nat. Prod. 59, 1096-1098.
167. Ling, S.-K., Tanaka, T., and Kouno, I. (2002) New Cyanogenic and Alkyl Glycoside Constituents from Phyllagathis rotundifolia, J. Nat. Prod. 65, 131-135.
168. Costantino, V., Fattorusso, E., Mangoni, A., Aknin, M., Fall, A., Samb, A., and Miralles, J. (1993) An Unusual Ether Glycolipid from the Senegalese Sponge Trikentrion loeve Carter, Tetrahedron 49, 2711-2716.
169. Costantino, V., Fattorusso, E., and Mangoni, A. (1993) Isolation of Five-Membered Cyclitol Glycolipids, Crasserides: Unique Glycerides from the Sponge Pseudoceratina crassa, J. Org. Chem. 58, 186-191.
170. Wang, N.L., Yao, X.S., Ishii, R., and Kitanaka, S. (2001) Antiallergic Agents from Natural Sources: 3. Structures and Inhibitory Effects on Nitric Oxide Production and Histamine Release of Five Novel Polyacetylene Glucosides from Bidens parviflora WILLD, Chem. Pharm. Bull. 49, 938-942.
171. Ubillas, R.P., Mendez, C.D., Jolad, S.D., Luo, J., King, S.R., Carlson, T.J., and Fort, D.M. (2000) Antihyperglycemic Acetylenic Glucosides from Bidens pilosa, Planta Med. 66, 82-83.
172. Mateo, J.J., and Jimenez, M. (2000) Monoterpenes in Grape Juice and Wines, J. Chromatogr. A 881, 557-567.
173. Mateo, J.J., Gentilini, N., Huerta, T., Jimnez, M., and Di Stefano, R. (1997) Fractionation of Glycoside Precursors of Aroma in Grapes and Wine, J. Chromatogr. A 778, 219-224.
174. Schneider, R., Charrier, F., Moutounet, M., and Baumes, R. (2004) Rapid Analysis of Grape Aroma Glycoconjugates Using Fourier-Transform Infrared Spectrometry and Chemometric Techniques, Anal. Chim. Acta 513, 91-96.
175. Ayestarán, B., Guadalupe, Z., and León, D. (2004) Quantification of Major Grape Polysaccharides (Tempranillo v.) Released by Maceration Enzymes During the Fermentation Process, Anal. Chim. Acta 513, 29-39.
176. Williams, P.J., Strauss, C.R., Wilson, B., and Massywestropp, R.A. (1982) Novel Monoterpene Disaccharide Glycosides of Vitis vinifera Grapes and Wines, Phytochemistry 21, 2013-2020.
177. Sarry, J.-E., and Günata, Z. (2004) Plant and Microbial Glycoside Hydrolases: Volatile Release from Glycosidic Aroma Precursors, Food Chem. 87, 509-521.
178. D'Incecco, N., Bartowsky, E., Kassara, S., Lante, A., Spettoli, P., and Henschke, P. (2004) Release of Glycosidically Bound Flavour Compounds of Chardonnay by Oenococcus oeni During Malolactic Fermentation, Food Microbiol. 21, 257-265.
179. Whitehurst, R.J. (ed.) (2004) Emulsifiers in Food Technology. Blackwell Publ., Ames, Iowa, p. 264.
180. De Roode, B.M., Franssen, A.C.R., Van Der Padt, A., Boom, R.M. (2003) Perspectives for the Industrial Enzymatic Production of Glycosides, Biotechnol. Prog. 19, 1391-1402.
181. Zhang, Q.S., Guo, B.N., and Zhang, H.M. (2004) Development and Application of Gemini Surfactants, Prog. Chem. 16, 343-348.
182. Hait, S.K., and Moulik, S.P. (2002) Gemini Surfactants: A Distinct Class of Self-Assembling Molecules, Curr. Sci. 82, 1101-1111.