TY - JOUR
T1 - Synthesis and identification of an endogenous sperm activating and attracting factor isolated from eggs of the ascidian Ciona intestinalis; An example of nanomolar-level structure elucidation of novel natural compound
AU - Oishi, Tohru
AU - Tsuchikawa, Hiroshi
AU - Murata, Michio
AU - Yoshida, Manabu
AU - Morisawa, Masaaki
N1 - Funding Information:
We thank Drs. M. Ikeda and H. Ohtake (Dokkyo University School of Medicine) for their help in the measurement of ESI/TOF-MS; Dr. H. Naoki (Suntory Institute for Bioorganic Research) for measurement of MS/MS; to Mr. S. Adachi (Osaka University) for NMR measurements; Dr. Tsutsui (Univ. of Tokyo) for his advice; and to Ms M. Ishikawa, Mr. H. Iryu, and Mr. M. Sekifuji (Univ. of Tokyo) for their technical work. We also thank the directors and staff of the Education and Research Center of Marine Bioresources (Tohoku University) and Otsuchi Marine Research Center (University of Tokyo) for supplying materials. This work was supported in part by a Grant-In-Aid for Scientific Research on Priority Area (A) (No. 12045235) from MEXT, Japan to M. Yoshida, M. Murata, and by Grant-In-Aids from the Ministry of Education, Culture, Sports, Science and Technology, Japan to M. Morisawa.
PY - 2004/8/9
Y1 - 2004/8/9
N2 - A sperm-activating and attracting factor (SAAF) was isolated from the eggs of the ascidian Ciona intestinalis, and its structure was deduced with only approximately 4 μg of the specimen. Based upon the proposed structure, two epimers were synthesized from chenodeoxycholic acid in 16 steps. Comparison between synthetic and natural compounds led to the unambiguous structure determination of SAAF to be (3R,4R,7R,25S)-3,4,7,26-tetrahydroxycholestane-3,26- disulfate. The synthetic pure specimen was also utilized to confirm that both sperm-activation and attraction were elicited by a single compound.
AB - A sperm-activating and attracting factor (SAAF) was isolated from the eggs of the ascidian Ciona intestinalis, and its structure was deduced with only approximately 4 μg of the specimen. Based upon the proposed structure, two epimers were synthesized from chenodeoxycholic acid in 16 steps. Comparison between synthetic and natural compounds led to the unambiguous structure determination of SAAF to be (3R,4R,7R,25S)-3,4,7,26-tetrahydroxycholestane-3,26- disulfate. The synthetic pure specimen was also utilized to confirm that both sperm-activation and attraction were elicited by a single compound.
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U2 - 10.1016/j.tet.2004.02.075
DO - 10.1016/j.tet.2004.02.075
M3 - Article
AN - SCOPUS:3242706203
VL - 60
SP - 6971
EP - 6980
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 33
ER -