Nematicidal sphingolipids from the freshwater fungus Paraniesslia sp. YMF1.01400

European Journal of Lipid Science and Technology

Volumn 107, Issue 11, 2005, Pages 779-785

  Dong, Jin Yan ^a   Ru, Li ^a   He, Hong Ping ^b   Zhang, Ke Qin ^a  

^a YUNNAN UNIVERSITY   (China)

^b KUNMING INSTITUTE OF BOTANY   (China)

Author keywords

Bursaphelenchus xylophilus; Cerebroside; Fungus; Paraniesslia; Sphingolipid

Indexed keywords

BURSAPHELENCHUS XYLOPHILUS; FUNGI;

EID: 28444432744     PISSN: 14387697     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejlt.200500219     Document Type: Article

References (57)

1. H. R. Cheng, M. S. Lin, W. Q. Li, Z. D. Fang: The occurrence of pine wilt disease by a nematode found in Nanjing. For Pest Dis. 1983, 4, 1-5.
2. L. Y. Jiang: The history and control strategy of pine wilt disease in Japan. For Pest Dis. 1994, 3, 45-47.
3. Z. A. Siddiqui, I. Mahmood: Biological control of plant-parasitic nematodes by fungi: A review. Bioresource Technol. 1996, 58, 229-239.
4. H. Anke, O. Sterner: Nematicidal metabolites from higher fungi. Curr Org Chem. 1997, 1, 427-440.
5. C. Sankaranarayanan, S. Hussaini, S. Sreeramakumar, R. D. Prasad: Nematicidal effect of fungal filtrates against root-knot nematodes. J Biol Control. 1997, 11, 37-41.
6. P. R. Chattopadhyay, A. B. De: Inhibitory effects of certain fungi on the larval hatch of Meloidogyne inconita. Ind J Nematol. 1995, 25, 204-205.
7. K. N. Pathak, B. Kumar: Nematotoxic effects of Trichoderma harzianum culture filtrate on second stage juveniles of rice root knot nematode. Ind J Nematol. 1995, 25, 223-224.
8. T. A. Khan, S. I. Hussain: Effect of culture filtrates of soil fungi on the mortality and hatching of reniform nematode (Rotylenchulus reniformis). Ind J Nematol. 1989, 19, 35-40.
9. S. T. Khan, T. A. Kgan: Effect of culture filtrates of soil fungi on the hatching and mortality of root knot nematode (Meloidogyne incognita). Curr Nematol. 1992, 3, 53-60.
10. S. P. Sing, V. Pant, A. M. Khan, S. K. Saxena: Inhibitory effect of culture filtrate of some rhizosphere fungi of tomato as influenced by oil cakes on mortality and larval hatch of Meloidogyne incognita. Nematol Mediterr. 1983, 11, 119-123.
11. A. Mayer, H. Anke, O. Stemer: Omphalotin, a new cycle peptide with potent nematicidal activity from Omphalotus olearius. I. Fermentation and biological activity. Nat Prod Lett. 1997, 10, 25-32.
12. O. Stemer, W. Etzel, A. Mayer: Omphalotin, a new cycle peptide with potent nematicidal activity from Omphalotus olearius. II. Structure elucidation. Nat Prod Lett. 1997, 10, 33-38.
13. J. Y. Dong, Z. X. Zhao, L. Cai, S. Q. Liu, H. R. Zhang, M. Duan, K. Q. Zhang: Nematicidal effect of freshwater fungal cultures against the pine-wood nematode, Bursaphelenchus xylophilus. Fungal Diversity. 2004, 15, 123-135.
14. L. Cai, C. K. M. Tsui, K. Q. Zhang, K. D. Hyde: Aquatic fungi from lake Fuxian, Yunnan, China. Fungal Diversity 2002, 9, 57-70.
15. K. Clement, M. Tsui, K. D. Hyde, I. J. Hodgkiss: Paraniesslia tuberculata gen. et sp. nov., and new records or species of Clypeosphaeria, Leptosphaeria and Astrosphaeriella in Hong Kong freshwater habitats. Mycologia 2001, 93, 1002-1009.
16. J. H. Jung, C. O. Lee, Y. C. Kim, S. S. Kang: New bioactive cerebrosides from Arisaema amurense. J Nat Prod. 1996, 59, 319-322.
17. M. Stadler, H. Anke, W. R. Arendholz, F. Hansske, U. Anders, O. Sterner, K. E. Bergquist: Lachnumon and lachnumol A, new metabolites with nematocidal and antimicrobial activities from the ascomycete Lachnum papyraceum (Karst) Karst. I. Producing organism, fermentation, isolation and biological-activities. J Ant. 1993, 46, 961-967.
18. R. D. Sitrin, G. Chan, J. Dingerdissen, C. Debrosse, R. Mehta, G. Roberts, S. Rottschaefer, D Staiger, J. Valenta, K. M. Snader, R. J. Stedman, J. R. E. Hoover: Isolation and structure determination of. Pachybasium cerebrosides which potentiate the antifungal activity of aculeacin. J Ant. 1988, 41, 469-480.
19. Z. J. Zhan, J. M. Yue: New glycosphingolipids from the fungus Catathelasma ventricosa. J Nat Prod. 2003, 66, 1013-1016.
20. M. Meyer, M. Guyot: New sphingosines from the marine sponge Grayella cyatophora. J Nat Prod. 2002, 65, 1722-1723.
21. J. M. Gao, W. M. Zhu, S. Q. Zhang, X. Zhang, A. L. Zhang, H. Chen, Y. Y. Sun, M. Tan: Sphingolipids from the edible fungus Tuber indicum. Eur J Lipid Sci Technol. 2004, 106, 815-821.
22. R. Higuchi, M. Inagaki, K. Togawa, T. Miyamoto, T. Komori: Isolation and structure of cerebrosides from the sea cucumber Pentacta australis. Liebigs Ann Chem. 1994, 653-658.
23. P. K. Agrawal: NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides. Phytochemistry. 1992, 31, 3307-3330.
24. 13C] enriched monosaccharides. Signal assignments and orientational dependence of geminal and vicinal carbon-carbon and carbon-hydrogen spin-spin coupling constants. J Am Chem Soc. 1976, 98, 5807-5813.
25. T. Murakami, T. Shimizu, K. Taguchi: Synthesis of sphingadienine-type glucocerebrosides. Tetrahedron 2000, 56, 533-545.
26. S. Suglyama, M. Honda, R. Higuchi, T. Komori: Biologically active glycosides from asteroidean. XXVI. Stereochemistry of the four diastereomers of ceramide and ceramide lactoside. Liebigs Ann Chem. 1991, 349-356.
27. S. S. Kang, J. S. Kim, Y. N. Xu, Y. H. Kim: Isolation of a new cerebroside from the root bark of Aralia elata. J Nat Prod. 1999, 62, 1059-1060.
28. X. S. Chen, Y. L. Wu, D. H. Chen: Structure determination and synthesis of a new cerebroside isolated from the traditional Chinese medicine Typhonium giganteum Engl. Tetrahedron Lett. 2002, 43, 3529-3532.
29. G. Kawai, Y. Ikeda, K. Tubaki: Fruiting of Schizpphyllum commune induced by certain ceramides and cerebrosides from Penicillium funiculosum. Agric Biol Chem. 1985, 49, 2137-2146.
30. 2-ATPase activator from Symbiodinium sp. Liebigs Ann Chem. 1994, 41-48.
31. K. A. Karlsson, H. Leffler, B. E. Samuelsson: Characterization of cerebroside monoglycosylceramide from the sea anemone, Metridium senile. Identification of the major long chain base as an unusual dienic base with a methyl branch at a double bond. Biochim Biophys Acta. 1979, 574, 79-93.
32. G. W. Zhang, X. Q. Ma, C. X. Zhang, J. Y. Su, W. C. Ye, X. Q. Zhang, X. S. Yao, L. M. Zeng: Two new ceramides from the marine sponge Ircinia fasciculate. Helv Chim Acta. 2005, 88, 885-890.
33. T. Sakaki, U. Zahringer, D. C. Warnecke, A. Fahl, W. Knogge, E. Heinz: Sterol glycosides and cerebrosides accumulate in Pichia pastoris, Rhynchosporium secalis and other fungi under normal conditions or under heat shock and ethanol stress. Yeast. 2001, 18, 679-695.
34. K. M. Jenkins, P. R. Jensen, W. Fenical: Thraustochytrosides A-C: New glycosphingolipids from a unique marine protist, Thraustochytrium globosum. Tetrahedron Lett. 1999, 40, 7637-7640.
35. A. Ballio, C. G. Casinovi, M. Framondino, G. Marino, G. Nota, B. Santurbano: A new cerebroside from Fusicoccum amygdali. Biochim Biophys Acta. 1979, 573, 51-60.
36. Y. Mizushina, L. Hanashima, T. Yamaguchi, M. Takemura, F. Sugawara, M. Saneyoshi, A. Matsukage, S. Yoshida, K. Sakaguchi: A mushroom fruiting body-inducing substance inhibits activities of replicative DNA polymerases. Biochem Biophys Res Commun. 1998, 249, 17-22.
37. J. M. Yue, C. Q. Fan, J. Xu, H. D. Sun: Novel ceramides from the fungus Lactarium volemus. J Nat Prod. 2001, 64, 1246-1248.
38. J. M. Gao, J. Shen, A. L. Zhang, W. Zhu, X. Zhang, J. K. Liu: Chemical constituents of the fungus Leccinum extremiorientale. Chin J Org Chem. 2003, 23, 853-857.
39. S. G. Batrakov, I. V. Konova, V. I. Sheichenko, S. E. Esipov, L. A. Galanina, L. N. Istratova: Unusual fatty acid composition of cerebrosides from the filamentous soil fungus Mortierella alpina. Chem Phys Lipids. 2002, 117, 45-51.
40. J. M. Gao, L. Hu, Z. J. Dong, J. K. Liu: New glycosphingolipid containing an unusual sphingoid base from the basidiomycete Polyporus ellisii. Lipids. 2001, 36, 521-527.
41. J. W. Blunt, B. R. Copp, M. H. G. Munro, P. T. Northcote, M. R. Prinsep: Marine natural products. Nat Prod Rep. 2004, 21, 1-49.
42. D. J. Faulkner: Marine natural products. Nat Prod Rep. 2002, 19, 1-48.
43. G. W. Zhang, X. Q. Ma, C. X. Zhang, J. Y. Su, W. C. Ye, X. Q. Zhang, X. S. Yao, L. M. Zeng: Two new ceramides from the marine sponge Ircinia fasciculate. Helv Chim Acta. 2005, 88, 885-890.
44. C. Emura, R. Higuchi, T. Miyamoto: Amphimelibiosides A-F, six new ceramide dihexosides isolated from a Japanese marine sponge Amphimedon sp. J Org Chem. 2005, 70, 3031-3038.
45. Y. Venkateswarlu, N. S. Reddy, P. Ramesh, M. R. Rao, T. S. Ram: New ceramides from the sponges of gulf of Mannar. Ind J Chem. 1998, 37B, 1264-1268.
46. G. Kawai, Y. Ikeda: Structure of biologically active and inactive cerebrosides prepared from Schizophyllum commune. J Lipid Res. 1985, 26, 338-343.
47. J. Koga, T. Yamauchi, M. Shimura, N. Ogawa, K. Oshima, K. Umemura, M. Kikuchi, N. Ogasawara: Cerebrosides A and C, sphingolipid elicitors of hypersensitive cell death and phytoalexin accumulation in rice plants. J Biol Chem. 1998, 273, 31985-31991.
48. G. Kawai, M. Ohnishi, Y. Fujino, Y. Ikeda: Stimulatory effect of certain plant sphingolipids on fruiting of Schizophyllum commune. J Biol Chem. 1986, 261, 779-784.
49. P. Sperling, D. Warnecke, E. Heinz: Lipid metabolism and membrane biogenesis. 11. Plant sphingolipids. In: Topics in Current Genetics. Ed. G. Daum, Springer-Verlag, Heidelberg/Berlin (Germany) 2004, pp. 337-381.
50. N. Abboushi, A. El-Hed, W. Ei-Assaad, L. Kozhaya, M. E. Ei-Sabban, A. Bazarbachi, R. Badreddine, A. Bielawska, J. Usta, G. S. Dbaibo: Ceramide inhibits IL-2 production by preventing protein kinase C-dependent NF-κB activation: Possible role in protein kinase Ctheta regulation. J Immunol. 2004, 173, 3193-3200.
51. 2 from inositol trisphosphate- and phosphatidic acid-sensitive intracellular stores through a mechanism independent of inositol trisphosphate. J Biol Chem. 1996, 271, 11148-11155.
52. Y. Mizushina, L. Hanashima, T. Yamaguchi, M. Takemura, T. Sugawara, M. Sancyoshi, A. Matsukage, S. Yoshida, K. Sakaguchi: A mushroom fruiting body-inducing substance inhibits activities of replicative DNA polymerases. Biochem Biophys Res Commun. 1998, 249, 17-22.
53. T. K. Ghosh, J. Bian, D. L. Gill: Sphingosine 1-phosphate generated in the endoplasmic reticulum membrane activates release of stored calcium. J Biol Chem. 1994, 269, 22628-22635.
54. Y. Jin, E. Knudsen, L. Wang, Y. Bryceson, B. Damaj, S. Gessani, A. A. Maghazachi: Sphingosine 1-phosphate is a novel inhibitor of T-cell proliferation. Blood. 2003, 101, 4909-4915.
55. M. Manggau, D. S. Kim, L. Ruwisch, R. Vogler, H. C. Korting, M. Schafer-Korting, B. Kleuser: 1Alpha, 25-dihydroxyvitamin D3 protects human keratinocytes from apoptosis by the formation of sphingosine-1-phosphate. J Invest Dermatol. 2001, 117, 1241-1248.
56. E. M. Schmelz, P. C. Roberts, E. M. Kustin, L. A. Lemonnier, M. C. Sullards, D. L. Dillehay, A. H. Merrill: Modulation of intracellular β-catenin localization and intestinal tumorigenesis in vivo and in vitro by sphingolipids. Cancer Res. 2001, 61, 6723-6729.
57. V. E. Nava, O. Cuvillier, L. C. Edsall, K. Kimura, S. Milstien, E. P. Gelmann, S. Spiegel: Sphingosine enhances apoptosis of radiation-resistant prostate cancer cells. Cancer Res. 2000, 60, 4468-4474.