摘要
从中国虫纹东方豚［Ｆｕｇｕ ｖｅｒｍｉｃｕｌａｒｉｓ（Ｔｅｍｍｉｎｃｋ ｅｔ Ｓｃｈｌｅｇｅｌ）］肝脏中，分离得到３种次生代谢产物，经波谱分析和化学转化等方法，确定了它们的化学结构为河豚毒素（Ⅰ）、４．９脱水河豚毒素（Ⅰ）和４．９－脱水河豚毒素－６， １１－乙二醚（ Ⅵ）。其中化合物（ Ⅵ）为一新河豚毒素衍生物。河豚毒素经 ＣＦ_３ＣＯＯＨ酸解反应，分别产生 ４，９脱水河豚毒素（Ⅱ）和 ４，９，１０，１１二脱水河豚毒素（ Ⅳ）；４，９脱水河豚毒素（Ⅱ）经乙酰化反应产生 ４，９－脱水－５，１１－二乙酰化河豚毒素（Ⅴ），其中化合物（Ⅳ）和（Ⅴ）为新的反应产物。
From a water extraction of Chinese Fugu vermiculari (Temminck et schlegel),collected from North sea near Xiamen, 3 compounds named tetrodotoxin(Ⅰ), 4,9- anhydrotetrodotoxin (Ⅰ) and 4, 9-anhydrotetrodotoxin-5, 11-diether (Ⅵ)were isolated. Their structures were identified by various spectrial (IR, HNMR, CNMR, MS et al ) analysis and comparison with chemical and physical data with authentic samples reported in literatures,is 4, 9-anhydrotetrodotoxin-6, 11-diether a new alkaloid. The 4, 9-anhydrotetrodotoxin was considered as a metabolited product by the evdience of (Ac)_2O esterification of water extraction of puffer fish to form 4, 9-anhydro-5, 11-diacetyl-tetrodotoxin (Ⅴ). The co-existence of TTX hemilactal (1)-lactone (11)tautomerism in weak acidic solution was observed in ~1H and ^(13)C NMR spectra. Under CF_3COOH acidic condition,the tetrodotoxin occcurred a anhydrolation to from 4, 9-anhydrotetrodotoxin, and further rearrangment to produce 4, 9, 10, 11-dianhy- dro-tetrodotoxin, 4, 9-anhydrotetrodotoxin.
出处
《中国海洋药物》
CAS
CSCD
1999年第2期4-8,共5页
Chinese Journal of Marine Drugs
基金
天然药物及仿生药物国家重点实验室基金
关键词
河豚
虫纹东方豚
化学成分
Fugu vermicularis (Temminck et Schlegel )
4
9-anhydrotetrodotoxin-6
11- diether
esterification
structural identification.
