NEW POLYCHLORINATED AMINO-ACID DERIVATIVES FROM THE MARINE SPONGE DYSIDEA-HERBACEA
NEW POLYCHLORINATED AMINO-ACID DERIVATIVES FROM THE MARINE SPONGE DYSIDEA-HERBACEA
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DOI：
10.1021/jo00075a029
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发表时间：
1993-11-05
影响因子：
3.6
通讯作者：
CLARDY, J
中科院分区：
文献类型：
--
作者：
UNSON, MD;ROSE, CB;CLARDY, J
从热带海绵Dysideaherbacea（Dictyoceratida）中分离得到一系列新的多氯代氨基酸衍生物。从波恩佩的一份标本中分离出两种主要的六氯代代谢物dysideathiazole（4）和N-甲基dysideathiazole（5），以及一种次要的五氯代化合物10-脱氯-N-甲基dysideathiazole（6）。10-Dechlorodysideathiazole（7）作为一种次要成分从帕劳样本中分离出来，同时分离出的还有主要代谢物9，10-dichloro-N-methyldysideathiazole（8）和10-dichloro-N-methyldysideathiazole（6）。来自帕劳的第二个标本含有dysideapyrrolidone（9）。化合物4-9的结构经波谱方法鉴定。通过天然产物和氨基甲酸酯衍生物17的X射线晶体学确定化合物4-6的绝对立体化学在所有手性中心处为S。
A new series of polychlorinated amino acid derivatives were isolated from the tropical marine sponge Dysidea herbacea (Dictyoceratida). Two major hexachlorinated metabolites, dysideathiazole (4) and N-methyldysideathiazole (5), and a minor pentachlorinated compound, 10-dechloro-N-methyldysideathiazole (6), were isolated from a specimen from Pohnpei. 10-Dechlorodysideathiazole (7) was isolated as a minor constituent of a Palauan specimen, together with the major metabolites 9,10-didechloro-N-methyldysideathiazole (8) and 10-dechloro-N-methyldysideathiazole (6). A second specimen from Palau contained dysideapyrrolidone (9). The structures of 4-9 were elucidated by spectroscopic methods. The absolute stereochemistry of compounds 4-6 was determined by X-ray crystallography of the natural products and of the carbamate derivative 17 to be S at all chiral centers.