Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1996-04-04
2000-10-03
Barts, Samuel
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
564224, C07C21500
Patent
active
061275786
ABSTRACT:
This invention provides a method of altering the metabolism of sphingolipids in a cell comprising contacting the cell with a fumonisin, or an analog thereof. The invention also provides a method of detecting the consumption of a fumonisin or a fumonisin analog in a subject comprising (A) detecting, in a sample from the subject, the state of the metabolic pathway of sphingolipids and (B) comparing the state of the metabolic pathway to that of a normal subject, the presence of a change in the state of the metabolic pathway indicating the consumption of a fumonisin or a fumonisin analog. Also provided is a method of detecting the presence of a fumonisin or fumonisin analog contamination in a sample from a food or feed comprising detecting a reaction of the metabolic pathway of sphingolipids, the presence of the reaction indicating the presence of a fumonisin or fumonisin analog contamination. Furthermore, novel fumonisin analogs and compositions comprising fumonisins and fumonisin analogs are provided.
REFERENCES:
patent: 5103002 (1992-04-01), Wieland
patent: 5110987 (1992-05-01), Liotta et al.
patent: 5190876 (1993-03-01), Merrill, Jr. et al.
patent: 5232837 (1993-08-01), Merrill, Jr. et al.
patent: 5518879 (1996-05-01), Merrill, Jr. et al.
Jimenez, C., et al., Journal of Natural Products, vol. 53, No. 4, pp. 978-982, Jul.-Aug. 1990.
Kamimura, A. et al., Tetrahedron Letters, vol. 30, No. 6, pp. 731-734, 1989.
Prostenik, M., et al., Chemical Abstracts, vol. 53, No. 1, abstract No. 1131g, 1960.
Palameta, B., et al., Chemical Abstracts, vol. 56, No. 10, abstract No. 14556g 1962.
Chem Abstract 1971:505010; RN 49794-20-9 & 49794-21-0, 1973.
Chem Abstracts 1978:503399, RN=67318-66-5, Jun. 1978.
Bezuidehout, et al., "Structure Elucidaton of the Fumonisins, Mycotoxins from Fusarium moniliforme," J. Chem. Soc. Comm. 743-745 (1988).
Bottini, et al., "Phytotoxins. II. Characterization of a Phytoxic Fraction from Alternaria Alternata F. Sp. Lycopersici," Tetrahedron Lett. 22:2723-2726 (1981).
Dillehay, et al., "Dietary Sphingolyelin Inhibits 1,2-Dimethylhydrazine-Induced Colon Cancer in CF1 Mice.sup.1-4," American Institute of Nutrition , 615-620 (1994).
Faucher, et al., "Regulation of the Epidermal Growth Factor Receptor Phosphorylation State by Sphingosine in A431 Human Epidermoid Carcinoma Cells," J. Biol. Chem. 263:5319-5327 (1988).
Ferguson, "Lipid anchors on membrane proteins," Current Opinion in Structural Biology, 1:522-529 (1991).
Gaver and Sweeley, "Chemistry and Metabolism of Sphingolipids. 3-Oxo Derivatives of N-Acetylsphingosine and N-Acetyldihydrosphingosine," J. Amer. Chem. Soc. 88:3643-3647 (1966).
Gelderblom, et al., "Fumonisins-Novel Mycotoxins with Cancer-Promoting Activity Produced by Fusarium moniliforme," Appl. Environ. Microbiol. 54:1806-1811 (1988).
Hakomori, "Bifunctional Role of Glycosphingolipids," J. Biol. Chem. 265:18713-18716 (1990).
Hakomori, "Glycosphingolipids in Cellular Interaction, Differentiation, and Oncogenesis," Ann. Rev. Biochem. 50:733-764 (1981).
Hannun and Bell, "Functions of Sphingolipids and Sphingolipid Breakdown Products in Cellular Regulation," Science 243:500-507 (1989).
Hannun, et al., "Sphingosine Inhibition of Protein Kinase C Activity and of Phorbol Dibutyrate Binding In Vitro and in Human Platelets," J. Biol. Chem. 261:12604-12609 (1986).
Harrison, et al., "Pulmonary edema and hydroxthoraz in swine produced by fumonisin B.sub.1, a toxic metabolite of Fusarium moniliforme," J. Vet. Diagn. Invest. 2:217-221 (1990).
Jamal, et al., "Plasma Membrane Fractions from Rat Liver Contain a Phosphatidate Phosphohydrolase Distinct from That in the Endoplasmic Reticulum and Cytosol," J. Biol. Chem. 266:2988-2996 (1991).
Jaskiewicz, et al., "Carcinogenicity of Fusarium moniliforme Culture Material in Rats," J. Natl. Cancer Inst. 78:321-325 (1987).
Kellerman, et al., "A Mycotoxicosis of Equidae Caused by Fusarium Moniliforme Sheldon," Onderstepoort J. Vet. Res. 39:205-208 (1972).
Kriek, et al., "A Comparative Study of the Toxicity of Fusarium Verticillioides (=F. Moniliforme) To Horses, Primates, Pigs, Sheep and Rats," Onderstepoort J. Vet. Res. 48:129-131 (1981).
Li, et al., "Experimental Studies on the Carcinogenicity of Fungus-contaminated Food from Linxian County," in Genetic and Environmental Factors in Experimental and Human Cancer (Gelboin, H. V., ed.) Japan Sci. Soc. Press, Tokyo, pp. 139-148 (1980).
Marasas, W. F. O., Cancer of the Oesophagus, (Pfeiffer, C. J., ed.) CRC Press, Boca Raton, vol. 1, pp. 29-40 (1982).
Marasas,et al.,"Leukoencephalomalacia in a Horse Induced by Fumonisin B.sub.1 Isolated from Fusarium Moniliforme," Onderstepoort J. Vet Res. 55:197-203 (198).
Marasas, "Primary Liver Cancer and Oesophageal Basal Cell Hyperplasia in Rats Caused by Fusarium Moniliforme," Int. J. Cancer 34:383-387 (1984).
Medlock and Merrill, "Rapid Turnover of Sphingosine Synthesized De Novo from [.sup.14 C]Serine by Chinese Hamster Ovary Cells," Biochem. Biophys. Res. Commun. 157:232-237 (1988).
Merrill, "Characterization of Serine Palmitoyltransferase Activity in Chinese Hamster Ovary Cells," Biochem. Biophys. Acta 754:284-291 (1983).
Merrill, A. H., Jr., "Cell Regulation by Sphingosine and More Complex Sphingolipids," J. Bioenergetics and Biomembranes, 28:83-104 (1991).
Merrill, and Jones, "An update of the enzymology and regulation of sphingomyelin metabolism," Biochem. Biophys. Acta 1044:1-12 (1990).
Merrill and Wang, "Biosynthesis of Long-chain (Sphingoid) Bases from Serine by LM Cells," J. Biol. Chem. 261:3764-3769 (1986).
Merrill, et al., "Structural Requirements for Long-Chain (Sphingoid) Base Inhibition of Protein Kinase C in Vitro and for the Cellular Effects of These Compounds," Biochemistry 28:3138-3145 (1989).
Merrill and Liotta, "Lipids as hormones and second messengers," Current Biology in Structural Biology, 1:515-521 (1991).
Merrill, et al., "Quantitation of Free Sphingosine in Liver by High-Performance Liquid Chromatography," Anal. Biochem. 171:373-381 (1988).
Merrill, Jr., "Sphingosine and Other Long-chain Bases That Alter Cell Behavior," Current Topics in Membranes, Chapter 14, 40:361-386 (1994).
Merrill, "Cell Regulation by Sphingosine and More Complex Sphingolipids," J. of Bioener. and Biomembr., 23:83-104 (1991).
Messmer, et al., "Sphingolipid Biosynthesis by Rat Liver Cells: Effects of Serine, Fatty Acids and Lipoproteins," J. Nutr. 119:534-538 (1989).
Morell and Radin, "Specificity in Ceramide Biosynthesis from Long Chain Bases and Various Fatty Acyl Coenzyme A's by Brain Microsomes," J. Biol. Chem. 245:342-350 (1970).
Oishi, et al., "Inhibition of NA,K-ATPase and Sodium Pump by Protein Kinase C Regulators Sphingosine, Lysophosphatidylcholine, and Oleic Acid," J. Biol. Chem. 265:70-75 (1990).
Slife, et al., "Free Sphingosine Formation from Endogenous Substrates by a Liver Plasma Membrane System with a Divalent Cation Dependence and a Neutral pH Optimum," J. Biol. Chem. 264:10371-10377 (1989).
Stevens, et al., "Characteristics of the growth inhibition and cytotoxicity of long-chain (sphingoid) bases for Chinese hamster ovary cells: evidence for an involvement of protein kinase C," BIochem. Biophys. Acta 1051:37-45 (1990).
Sweeley, "Sphingolipids," In Biochemistry of Lipids and Membranes (D. E. Vance and J. E. Vance, eds.) Benjamin/Cummings Pub., Menlo Park, CA., Chapter 12, pp. 361-403 (1985).
Sweeley, "Sphingolipids," Biochem. of Lipids, Lipoproteins and Membranes, Chapter 11, pp. 327-360 (D. E. Vance and J. Vance, Editors, 1991).
Sydenham, et al., "Evidence for the Natural Occurrence of Fumonisin B.sub.1, a Mycotoxin Produced by Fusarium moniliforme, in Corn," J. Agric. Food Chem. 38:285-290 (1990).
Voss, et al., "Hepatotoxicity and Renal Toxicity in Rats of Corn Samples Associated with Field Cases of Equine Leukoencephalomalacia," Food Chem. Toxicol. 27:89-96 (1989).
Voss, et al., "Comparative studies of hepatotoxicity and fumonisin B.sub.1 and B.sub.2 content of water and chloroform/methanol extracts of Fusarium moniliforme strain MRC 826 culture material," Mycopathologia 112:81-92 (1990).
Wang, et al., Inhibitions of Sphi
Liotta Dennis C.
Merrill, Jr. Alfred H.
Riley Ronald T.
Wang Elaine W.
Barts Samuel
Emory University
Knowles, Esq. Sherry M.
The United States of America as represented by the Secretary of
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