2003 Fiscal Year Final Research Report Summary
Frontier in Structure Elucidation of Natural Products
| Project/Area Number |
12045243
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research on Priority Areas
|
| Allocation Type | Single-year Grants |
|---|
| Review Section |
Science and Engineering
|
|---|
| Research Institution | Osaka University |
|---|
Principal Investigator |
MURATA Michio Osaka University, Graduate School of Science, Professor, 大学院・理学研究科, 教授 (40183652)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
YOSHIDA Manabu University of Tokyo, Misaki Marine Biological Station, Lecturer, 大学院・理学系研究科, 講師 (60301785)
|
|---|
| Project Period (FY) |
2000 – 2002
|
| Keywords | Nanomolar structure determination / Sperm attractant / Sperm activating substance / Tunicates / Sterol sulfate / NMR structure determination / Tandem mass spectrometry / Total synthesis / 全合成 |
|---|
| Research Abstract |
Chemotaxis of sperm toward eggs during fertilization is a crucial event for species conservation, particularly for animals living in aquatic environments. Relevant chemical attractants have been found from a few marine organisms such as sea urchins and corals. We previously showed that sperm of the ascidian Ciona intestinalis is activated and then attracted toward the egg by a factor released from the egg, which led to the purification of sperm-activating and attracting factor (SAAF) from the egg-conditioning medium of Ciona intestinalis.
The structure of SAAF was proposed to be a novel polyhydroxysterol sulfate on the basis of 2D-^1H NMR and FAB-MS/MS analysis using no more than approximately 4 microgram of a specimen. However, there still remained small but serious ambiguity that the biological activity might be attributed to a minor constituent. Synthesis is, therefore, essential for the unequivocal identification of SAAF as the active principle, and for the complete structure elucidation including the stereochemistry at C25. SAAF and its C-25 epimer were synthesized from chenodeoxycholic acid in 19 steps via the pivotal intermediate and both the sperm-activating and attracting activity of them were bioassayed. Synthetic SAAF activated the sperms of ascidian Ciona intestinalis at 3.7 nM and concurrently exhibited the attracting activity at<10 nM, which led to the unambiguous structure determination of SAAF and the verification of its dual activity. It is noteworthy that 25-epi-SAAF turned out to possess the comparative activities as those of SAAF.
|
Research Products
(37 results)
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
[Publications] Murata, M., Matsuoka, S., Matsumori, N., Paul, G.K., Tachibana, K.: "Absolute configuration of amphidinol 3, the first complete structure determination from amphidinol hmologues : Application of a new configuration analysis based on the carbon-hydrogen spin-coupling constants."J. Am. Chem. Soc.. 121. 870-871 (1999)
Description
「研究成果報告書概要(欧文)」より
-
-
-
[Publications] Kazuaki Akasaka, K., Shichijyukari, S., Matsuoka, S., Murata, M., H.Meguro, H.Ohrui.: "Absolute configuration of a ceramide with a novel branched-chain fatty acid isolated from teh epiphytic dinoflagellate, Coolia monotis."Biosci. Biotech. Biochem.. 64. 1842 (2000)
Description
「研究成果報告書概要(欧文)」より
-
[Publications] Houdai, M., Matsuoka, S., Murata, M., Satake, M., Ota, S., Oshima, Y., Rhodes.L.L.: "Acetate labeling patterns dinoflagellate polyketides, amphidinols 2, 3 and 4."Tetrahedron. 57. 5551-5555 (2001)
Description
「研究成果報告書概要(欧文)」より
-
-
-
-
-
-
-
-
-
-
[Publications] Matsumori, N., Eiraku, N., Matsuoka, S., Oishi, T., Murata, M.: "Amphotericin B-ergosterol conjugata bearing powerful permeabilizing activity. Aoki, T., Iden, T."Chem. Biol.. (in press).
Description
「研究成果報告書概要(欧文)」より
