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Koga J, Yamauchi T, Shimura M, Ogawa N, Oshima K, Umemura K, Kikuchi M, Ogasawara N
Cerebrosides A and C, sphingolipid elicitors of hypersensitive cell death and phytoalexin accumulation in rice plants
Journal of Biological Chemistry 273 (1998)
31985-31991
|
b-D-Glcp-(1-1)-+
|
2HOC16={t3}-(1-2)-Sph
Sph = 9-methyl-(4E,8E)-4,8-sphingadienine-C18 |
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Magnaporthe grisea MAFF 305494
(NCBI TaxID 148305,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Oryza sativa
The structure was elucidated in this paperNCBI PubMed ID: 9822670Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Bio Science Laboratories, Meiji Seika Kaisha, Ltd., 5-3-1, Chiyoda, Sakado-shi, Saitama 350-0289, Japan
When plants interact with certain pathogens, they protect themselves by generating various chemical and physical barriers called the hypersensitive response. These barriers are induced by molecules called elicitors that are produced by pathogens. In the present study, the most active elicitors of the hypersensitive response in rice were isolated from the rice pathogenic fungus Magnaporthe grisea, and their structures were identified as cerebrosides A and C, sphingolipids that were previously isolated as inducers of cell differentiation in the fungus Schizophyllum commune. Treatment of rice leaves with cerebroside A induced the accumulation of antimicrobial compounds (phytoalexins), cell death, and increased resistance to subsequent infection by compatible pathogens. The degradation products of cerebroside A (fatty acid methyl ester, sphingoid base, and glucosyl sphingoid base) showed no elicitor activity. Hydrogenation of the 8E-double bond in the sphingoid base moiety or the 3E-double bond in the fatty acid moiety of cerebroside A did not alter the elicitor activity, whereas hydrogenation of the 4E-double bond in the sphingoid base moiety led to a 12-fold decrease in elicitor activity. Furthermore, glucocerebrosides from Gaucher's spleen consisting of (E)-4-sphingenine and cerebrosides from rice bran mainly consisting of (4E,8E)-4,8-sphingadienine and (4E,8Z)-4,8-sphingadienine showed no elicitor activity. These results indicate that the methyl group at C-9 and the 4E-double bond in the sphingoid base moiety of cerebrosides A and C are the key elements determining the elicitor activity of these compounds. This study is the first to show that sphingolipids have elicitor activity in plants.
Structure type: monomer
Location inside paper: Fig. 2, Cerebroside A
Compound class: glycolipid, glycosphingolipid, cerebroside
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5
Methods: gel filtration, 13C NMR, 1H NMR, IR, HPLC, negative FAB-MS, ePH-NMR, bioassay
Biological activity: elicitor activity in rice
Comments, role: Ceramides with the 4E-double bond and the methyl group at C-9 of sphingoid bases
Related record ID(s): 237624
NCBI Taxonomy refs (TaxIDs): 148305Reference(s) to other database(s): CCSD:
17966, CBank-STR:914
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There is only one chemically distinct structure:
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Koga J, Yamauchi T, Shimura M, Ogawa N, Oshima K, Umemura K, Kikuchi M, Ogasawara N
Cerebrosides A and C, sphingolipid elicitors of hypersensitive cell death and phytoalexin accumulation in rice plants
Journal of Biological Chemistry 273 (1998)
31985-31991
|
b-D-Glcp-(1-1)-+
|
2HOC18={t3}-(1-2)-Sph
Sph = 9-methyl-(4E,8E)-4,8-sphingadienine-C18 |
Show graphically |
Magnaporthe grisea MAFF 305494
(NCBI TaxID 148305,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Oryza sativa
The structure was elucidated in this paperNCBI PubMed ID: 9822670Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Bio Science Laboratories, Meiji Seika Kaisha, Ltd., 5-3-1, Chiyoda, Sakado-shi, Saitama 350-0289, Japan
When plants interact with certain pathogens, they protect themselves by generating various chemical and physical barriers called the hypersensitive response. These barriers are induced by molecules called elicitors that are produced by pathogens. In the present study, the most active elicitors of the hypersensitive response in rice were isolated from the rice pathogenic fungus Magnaporthe grisea, and their structures were identified as cerebrosides A and C, sphingolipids that were previously isolated as inducers of cell differentiation in the fungus Schizophyllum commune. Treatment of rice leaves with cerebroside A induced the accumulation of antimicrobial compounds (phytoalexins), cell death, and increased resistance to subsequent infection by compatible pathogens. The degradation products of cerebroside A (fatty acid methyl ester, sphingoid base, and glucosyl sphingoid base) showed no elicitor activity. Hydrogenation of the 8E-double bond in the sphingoid base moiety or the 3E-double bond in the fatty acid moiety of cerebroside A did not alter the elicitor activity, whereas hydrogenation of the 4E-double bond in the sphingoid base moiety led to a 12-fold decrease in elicitor activity. Furthermore, glucocerebrosides from Gaucher's spleen consisting of (E)-4-sphingenine and cerebrosides from rice bran mainly consisting of (4E,8E)-4,8-sphingadienine and (4E,8Z)-4,8-sphingadienine showed no elicitor activity. These results indicate that the methyl group at C-9 and the 4E-double bond in the sphingoid base moiety of cerebrosides A and C are the key elements determining the elicitor activity of these compounds. This study is the first to show that sphingolipids have elicitor activity in plants.
Structure type: monomer
C
43H
79NO
9Location inside paper: Fig. 2, Cerebroside C
Compound class: glycolipid, glycosphingolipid, cerebroside
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5
Methods: gel filtration, 13C NMR, 1H NMR, IR, HPLC, negative FAB-MS, ePH-NMR, bioassay
Biological activity: elicitor activity in rice
Comments, role: Ceramides with the 4E-double bond and the methyl group at C-9 of sphingoid bases
Related record ID(s): 137624
NCBI Taxonomy refs (TaxIDs): 148305Reference(s) to other database(s): CCSD:
17966, CBank-STR:914
Show glycosyltransferases
There is only one chemically distinct structure:
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