| Project/Area Number |
08680630
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Bioorganic chemistry
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| Research Institution | HIROSHIMA UNIVERSITY |
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Principal Investigator |
OHTA Shinji Instrument Center for Chemical Analysis, HIROSHIMA UNIVERSITY Associate Professor, 機器分析センター, 助教授 (60185270)
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| Co-Investigator(Kenkyū-buntansha) |
UNO Mihoko Instrument Center for Chemical Analysis, HIROSHIMA UNIVERSITY Academic Staff Mem, 機器分析センター, 教務員 (80263672)
IKEGAMI Susumu Faculty of Applied Biological Science, HIROSHIMA UNIVERSITY Professor, 生物生産学部, 教授 (80011980)
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| Project Period (FY) |
1996 – 1997
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| Project Status |
Completed (Fiscal Year 1997)
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| Budget Amount *help |
¥2,500,000 (Direct Cost: ¥2,500,000)
Fiscal Year 1997: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1996: ¥1,500,000 (Direct Cost: ¥1,500,000)
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| Keywords | Marine Sponge / Ancorina Sp. / Starfish Embryos / Blastulation / Specific Inhibitor / Tetramic Acid / Ancorinoside A / Absolute Configuration / ヌクレオシド / オンナミド |
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| Research Abstract |
A MeOH extract of the marine sponge Ancorina sp.collected off the coast of Tokushima Prefecture inhibited the blastulation of strfish embryos. Bioassay-guided purification of the crude extract resulted in the isolation of a novel tetramic acid glycoside, which was designated ancorinoside A (1). The structure of ancorinoside A (1) was determined to be (5R) -5-carboxymethyl-3- {22-O- [beta-D-glucopyranosyl- (1*4) -beta-D-galactopyranosyluronic acid] -1-hydroxydocosylidene} -1-methyl-2,4-pyrrolidinedione on the basis of its spectral data. Ancorinoside A (1) is the first metabolite having a tetramic acid ring the precursor of which is considered to be a D-amino acid. The structure of the dicarboxylic acid witha 21-methylene chain is also unique to ancorinoside A (1). When fertilized starfish eggs were cultured from fertilization in the presence of 1 at a concentration of 0.4 mug/mL or greater, the development proceeded normally to 256-512 cell stage after encompassing 8-9 ycles of cleavage, and the embryos ceased to develop further witout exhibiting any sign of blastulation. Fertilization of starfish gametes was unaffected by the presence of 1 even at the concentration of 110 mug/ml. Further, 2-aminoadenosine (2), 2'-deoxyguanosine (3), and thymidine (4), and onnnamide (5) were isolated from the MeOH extract of the other marine sponges and inhibited blastulation of starfish embryos at concentrations of 2,3,5, and 2 mug/ml, respectively.
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