메뉴 건너뛰기




Volumn 50, Issue 7, 2007, Pages 947-951

6,11-Dideoxytetrodotoxin from the puffer fish, Fugu pardalis

Author keywords

LC MS; NMR; Puffer fish; Structure determination; Tetrodotoxin

Indexed keywords

6,11 DIDEOXYTETRODOTOXIN; TETRODOTOXIN; UNCLASSIFIED DRUG;

EID: 35649001902     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxicon.2007.06.026     Document Type: Article
Times cited : (50)

References (26)
  • 1
    • 0035927211 scopus 로고    scopus 로고
    • Stereocontrolled synthesis of (-)-5,11-dideoxytetrodotoxin
    • Asai M., Nishikawa T., Ohyabu N., Yamamoto N., and Isobe M. Stereocontrolled synthesis of (-)-5,11-dideoxytetrodotoxin. Tetrahedron 57 (2001) 4543-4558
    • (2001) Tetrahedron , vol.57 , pp. 4543-4558
    • Asai, M.1    Nishikawa, T.2    Ohyabu, N.3    Yamamoto, N.4    Isobe, M.5
  • 2
    • 0000893969 scopus 로고
    • Isolation of 11-nortetrodotoxin-6(R)-ol and other tetrodotoxin derivatives from the puffer Fugu niphobles
    • Endo A., Khora S.S., Murata M., and Yasumoto T. Isolation of 11-nortetrodotoxin-6(R)-ol and other tetrodotoxin derivatives from the puffer Fugu niphobles. Tetrahedron Lett. 29 (1988) 4127-4128
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4127-4128
    • Endo, A.1    Khora, S.S.2    Murata, M.3    Yasumoto, T.4
  • 4
    • 0141534438 scopus 로고    scopus 로고
    • A stereoselective synthesis of (-)-tetrodotoxin
    • Hinman A., and Du Bois J. A stereoselective synthesis of (-)-tetrodotoxin. J. Am. Chem. Soc. 125 38 (2003) 11510-11511
    • (2003) J. Am. Chem. Soc. , vol.125 , Issue.38 , pp. 11510-11511
    • Hinman, A.1    Du Bois, J.2
  • 5
    • 33750931583 scopus 로고    scopus 로고
    • Distribution of tetrodotoxin, saxitoxin, and their analogs among tissues of the puffer fish Fugu pardalis
    • Jang J., and Yotsu-Yamashita M. Distribution of tetrodotoxin, saxitoxin, and their analogs among tissues of the puffer fish Fugu pardalis. Toxicon 48 (2006) 980-987
    • (2006) Toxicon , vol.48 , pp. 980-987
    • Jang, J.1    Yotsu-Yamashita, M.2
  • 6
    • 0022930560 scopus 로고
    • Structure activity relations of tetrodotoxin, saxitoxin, and analogues
    • Kao C.Y. Structure activity relations of tetrodotoxin, saxitoxin, and analogues. Ann. NY Acad. Sci. 479 (1986) 52-67
    • (1986) Ann. NY Acad. Sci. , vol.479 , pp. 52-67
    • Kao, C.Y.1
  • 7
    • 0002961886 scopus 로고
    • Pharmacological studies on tarichatoxin, a potent neurotoxin
    • Kao C.Y., and Fuhrman F.A. Pharmacological studies on tarichatoxin, a potent neurotoxin. J. Pharmacol. Exp. Ther. 140 (1963) 31-40
    • (1963) J. Pharmacol. Exp. Ther. , vol.140 , pp. 31-40
    • Kao, C.Y.1    Fuhrman, F.A.2
  • 8
    • 35648988339 scopus 로고    scopus 로고
    • Kodama, M., Sato, S., 2005. Pufferfish toxin. In: Bureau of Environmental Health. Ministry of Health and Welfare, Japan (Ed.), The Manual for the Methods of Food Sanitation Tests, Food Hygienic Association, Tokyo, pp. 661-666.
  • 9
    • 0343905314 scopus 로고
    • 1-Hydroxy-5,11-dideoxytetrodotoxin, the first N-hydroxy and ring-deoxy derivative of tetrodotoxin found in the newt Taricha granulosa
    • Kotaki Y., and Shimizu Y. 1-Hydroxy-5,11-dideoxytetrodotoxin, the first N-hydroxy and ring-deoxy derivative of tetrodotoxin found in the newt Taricha granulosa. J. Am. Chem. Soc. 115 (1993) 827-830
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 827-830
    • Kotaki, Y.1    Shimizu, Y.2
  • 10
    • 33646021320 scopus 로고    scopus 로고
    • Hydrophilic interaction liquid chromatography-electrospray ionization mass spectrometry of tetrodotoxin and its analogs
    • Nakagawa T., Jang J., and Yotsu-Yamashita M. Hydrophilic interaction liquid chromatography-electrospray ionization mass spectrometry of tetrodotoxin and its analogs. Anal. Biochem. 352 (2006) 142-144
    • (2006) Anal. Biochem. , vol.352 , pp. 142-144
    • Nakagawa, T.1    Jang, J.2    Yotsu-Yamashita, M.3
  • 11
    • 0037043491 scopus 로고    scopus 로고
    • Sterecontrolled synthesis of 8,11-dideoxytetrodotoxin, unnatural analogue of puffer fish toxin
    • Nishikawa T., Urabe D., Yoshida K., Iwabuchi T., Asai M., and Isobe M. Sterecontrolled synthesis of 8,11-dideoxytetrodotoxin, unnatural analogue of puffer fish toxin. Org. Lett. 4 (2002) 2679-2682
    • (2002) Org. Lett. , vol.4 , pp. 2679-2682
    • Nishikawa, T.1    Urabe, D.2    Yoshida, K.3    Iwabuchi, T.4    Asai, M.5    Isobe, M.6
  • 12
    • 0037014710 scopus 로고    scopus 로고
    • Asymmetric total synthesis of 11-deoxytetrodotoxin, a naturally occurring congener
    • Nishikawa T., Asai M., and Isobe M. Asymmetric total synthesis of 11-deoxytetrodotoxin, a naturally occurring congener. J. Am. Chem. Soc. 124 26 (2002) 7847-7852
    • (2002) J. Am. Chem. Soc. , vol.124 , Issue.26 , pp. 7847-7852
    • Nishikawa, T.1    Asai, M.2    Isobe, M.3
  • 13
    • 4644371696 scopus 로고    scopus 로고
    • An efficient total synthesis of optically active tetrodotoxin
    • Nishikawa T., Urabe D., and Isobe M. An efficient total synthesis of optically active tetrodotoxin. Angew. Chem. Int. Ed. 43 (2004) 4782-4785
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 4782-4785
    • Nishikawa, T.1    Urabe, D.2    Isobe, M.3
  • 14
    • 0022658561 scopus 로고
    • Occurrence of tetrodotoxin and anhydrotetrodotoxin in Vibrio sp. isolated from the intestines of a xantihd crab, Atergatis floridus
    • Noguchi T., Jeon J.K., Arakawa O., Sugita H., Deguchi Y., Shida Y., and Hashimoto K. Occurrence of tetrodotoxin and anhydrotetrodotoxin in Vibrio sp. isolated from the intestines of a xantihd crab, Atergatis floridus. J. Biochem. 99 (1986) 311-314
    • (1986) J. Biochem. , vol.99 , pp. 311-314
    • Noguchi, T.1    Jeon, J.K.2    Arakawa, O.3    Sugita, H.4    Deguchi, Y.5    Shida, Y.6    Hashimoto, K.7
  • 15
    • 0038637028 scopus 로고    scopus 로고
    • First asymmetric total synthesis of tetrodotoxin
    • Ohyabu N., Nishikawa T., and Isobe M. First asymmetric total synthesis of tetrodotoxin. J. Am. Chem. Soc. 125 (2003) 8798-8805
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 8798-8805
    • Ohyabu, N.1    Nishikawa, T.2    Isobe, M.3
  • 17
    • 0029978602 scopus 로고    scopus 로고
    • Chemical and etiological studies on tetrodotoxin and its analogs
    • Yasumoto T., and Yotsu-Yamashita M. Chemical and etiological studies on tetrodotoxin and its analogs. J. Toxicol. Toxin Rev. 15 (1996) 81-90
    • (1996) J. Toxicol. Toxin Rev. , vol.15 , pp. 81-90
    • Yasumoto, T.1    Yotsu-Yamashita, M.2
  • 19
    • 33845280591 scopus 로고
    • New tetrodotoxin analogues from the newt Cynops ensicauda
    • Yasumoto T., Yotsu M., Murate M., and Naoki H. New tetrodotoxin analogues from the newt Cynops ensicauda. J. Am. Chem. Soc. 110 (1988) 2344-2345
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 2344-2345
    • Yasumoto, T.1    Yotsu, M.2    Murate, M.3    Naoki, H.4
  • 21
    • 0000404977 scopus 로고
    • Isolation and structural assignment of 11-nortetrodotoxin-6(S)-ol from the puffer Arothron nigropunctatus
    • Yotsu-Yamashita M., Hayashi Y., Khora S.S., Sato S., and Yasumoto T. Isolation and structural assignment of 11-nortetrodotoxin-6(S)-ol from the puffer Arothron nigropunctatus. Biosci. Biotechnol. Biochem. 56 (1992) 370-371
    • (1992) Biosci. Biotechnol. Biochem. , vol.56 , pp. 370-371
    • Yotsu-Yamashita, M.1    Hayashi, Y.2    Khora, S.S.3    Sato, S.4    Yasumoto, T.5
  • 22
    • 0028841233 scopus 로고
    • 5,6,11-Trideoxytetrodotoxin from the puffer fish, Fugu poecilonotus
    • Yotsu-Yamashita M., Yamagishi Y., and Yasumoto T. 5,6,11-Trideoxytetrodotoxin from the puffer fish, Fugu poecilonotus. Tetrahedron Lett. 36 (1995) 9329-9332
    • (1995) Tetrahedron Lett. , vol.36 , pp. 9329-9332
    • Yotsu-Yamashita, M.1    Yamagishi, Y.2    Yasumoto, T.3
  • 23
    • 0033127752 scopus 로고    scopus 로고
    • Isolation and structural assignment of 5-deoxytetrodotoxin from the puffer fish Fugu poecilonotus
    • Yotsu-Yamashita M., Schimmele B., and Yasumoto T. Isolation and structural assignment of 5-deoxytetrodotoxin from the puffer fish Fugu poecilonotus. Biosci. Biotechnol. Biochem. 63 (1999) 961-963
    • (1999) Biosci. Biotechnol. Biochem. , vol.63 , pp. 961-963
    • Yotsu-Yamashita, M.1    Schimmele, B.2    Yasumoto, T.3
  • 24
    • 0033061210 scopus 로고    scopus 로고
    • Effects of specific modifications of several hydroxyls of tetrodotoxin on its affinity to rat brain membrane
    • Yotsu-Yamashita M., Sugimoto A., Takai A., and Yasumoto T. Effects of specific modifications of several hydroxyls of tetrodotoxin on its affinity to rat brain membrane. J. Pharmacol. Exp. Ther. 289 (1999) 1688-1696
    • (1999) J. Pharmacol. Exp. Ther. , vol.289 , pp. 1688-1696
    • Yotsu-Yamashita, M.1    Sugimoto, A.2    Takai, A.3    Yasumoto, T.4
  • 25
    • 0842326232 scopus 로고    scopus 로고
    • Biological activity of 8,11-dideoxytetrodotoxin: lethality to mice and the inhibitory activity to cytotoxicity of ouabain and veratridine in mouse neuroblastoma cells, Neuro-2a
    • Yotsu-Yamashita M., Urabe D., Asai M., Nishikawa T., and Isobe M. Biological activity of 8,11-dideoxytetrodotoxin: lethality to mice and the inhibitory activity to cytotoxicity of ouabain and veratridine in mouse neuroblastoma cells, Neuro-2a. Toxicon 42 (2003) 557-560
    • (2003) Toxicon , vol.42 , pp. 557-560
    • Yotsu-Yamashita, M.1    Urabe, D.2    Asai, M.3    Nishikawa, T.4    Isobe, M.5
  • 26
    • 18944398163 scopus 로고    scopus 로고
    • Isolation of 4-S-cysteinyltetrodotoxin from the liver of the puffer fish Fugu pardalis, and formation of the adducts of 4,9-anhydrotetrodotoxin with thiols
    • Yotsu-Yamashita M., Goto A., and Nakagawa T. Isolation of 4-S-cysteinyltetrodotoxin from the liver of the puffer fish Fugu pardalis, and formation of the adducts of 4,9-anhydrotetrodotoxin with thiols. Chem. Res. Toxicol. 18 (2005) 865-871
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 865-871
    • Yotsu-Yamashita, M.1    Goto, A.2    Nakagawa, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.