TY - JOUR
T1 - 5,6,11-trideoxytetrodotoxin from the puffer fish, fugu poecilonotus
AU - Yotsu-Yamashita, Mari
AU - Yamagishi, Yuki
AU - Yasumoto, Takeshi
N1 - Funding Information:
Acknowledgments: The present study was supported by a grant from the Ministry of Education, Science, Sports and Culture, Japan (No.07102002). References and Notes 1. (a) Yasumoto, T.; Yotsu, M.; Murata, M.; Naoki, H. J. Am. Chem. Sot., 110, 2344-2345 (1988). (b) Khora, S. S.; Yasumoto, T. Tetrahedron Lett., 30, 4393-4394 (1989). (c) Endo, A.; Khora, S. S.; Murata, M.; Yasumoto, T. Tetruhedron L&t., 29, 4127-4129 (1988). (d) Yotsu, M.; Hayashi, Y.; Khora, S. S.; Sato, S.; Yasumoto, T. Biosci. Biotech. Biochem., 56, 370-371 (1992). (e) Yotsu, M.; Yasumoto, T.; Kim, H.; Kao, C. Y. Tetrahedron Left., 31, 3187-3190 (1990). (fl Kotaki, Y.; Shimizu, Y. J. Am. Chem. Sot., 115, 827-830 (1993). 2. The toxicity determined by mice bioassay [Hashimoto, Y .; Migita, M. Nippon Suisun Gakkaishi, 16, 341-346, (1951)] was 677 MU/g. The ratio between 4-epimer of 1 to 1 was determined to be 1:lO by the fluorometric-HPLC [Yotsu, M.; Endo, A.; Yasumoto, T. Agric. Biol. Chem., 49, 3077-3080 (1990)]. 2 and 3 were undetectable by this method. 3. Baker, M. D.; Mohammed, H. Y.; Veening, H. Anal. Chem ., 53, 1658-1662 (1981). All the analytical conditions were the same as those described in the literature except for the use of CosmosilW18-AR (4.6x 150 mm, Nakarai tesque) for separation. 4. Rf. values on TLC (silica gel 60 with pyridine-EtOAc-HOAc-H20, (0.77). Minimum lethal dose (mice, ip.): 2 (750 pg/kg), mouse death times ranged from 5 to 24 hrs after injection. 5. Two HMBC spectra were taken by setting the ./a at 2 and 10 Hz. 6. The sign of the Cotton effect reflects the configuration at C2 in Glactone [Beechamet, A. F. Tetrahedron Letr., 2355-2360 (1968)]. CD spectra (0.05 M at 23°C): 2 ( 48.7 mM, & 224.2 nm,
PY - 1995/12/18
Y1 - 1995/12/18
N2 - New tetrodotoxin analogs, 5,6,11 -trideoxytetrodotoxin and its 4-epimer, were isolated from the puffer fish, Fugu poecilonotus, and the structures were elucidated by spectroscopic methods. The discovery of the new analogs is highly significant with respect to the biosynthesis of tetrodotoxin.
AB - New tetrodotoxin analogs, 5,6,11 -trideoxytetrodotoxin and its 4-epimer, were isolated from the puffer fish, Fugu poecilonotus, and the structures were elucidated by spectroscopic methods. The discovery of the new analogs is highly significant with respect to the biosynthesis of tetrodotoxin.
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U2 - 10.1016/0040-4039(95)02020-P
DO - 10.1016/0040-4039(95)02020-P
M3 - Article
AN - SCOPUS:0028841233
VL - 36
SP - 9329
EP - 9332
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 51
ER -