期刊
JOURNAL OF NATURAL PRODUCTS
卷 82, 期 6, 页码 1627-1633出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.9b00128
关键词
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资金
- Japan Society for the Promotion of Science (JSPS) through its KAKENHI [JP17H03809]
- Innovative Area, Frontier Research on Chemical Communications grant [JP17H06406]
- Innovative Area, Frontier Research on Redesigning Biosynthetic Machineries [JP19H04636]
- Tohoku University, Division for Interdisciplinary Advanced Research and Education
Four kainic acid (KA, 1)-related compounds, 4-hydroxykainic acid (2), allo-4-hydroxykainic acid (3), N-dimethylallyl-L-glutamic acid (4), and N-dimethylallyl-threo-3hydroxyglutamic acid (5), were isolated from the red alga Digenea simplex. The structures of these compounds were elucidated using spectroscopic methods. Compounds 2 and 3 are possible oxidative metabolites of KA and allo-KA (6), respectively. Compound 4 was recently reported as the biosynthetic precursor of KA, but the absolute configuration of 4 has not been previously determined. Herein, we determined the absolute configuration of 4 as 2(S) using advanced Marfey's method. Compound 5 is similar to Ngerany1-3(R)-hydroxy-L-glutamic acid (8), which was previously identified in a domoic acid (DA)-containing red alga. Compounds 5 and 8 are predicted to be biosynthetic byproducts of the radical mediated cyclization reaction to form the pyrrolidine rings of KA and DA, respectively. Furthermore, the toxicities of 1-5 in mice were examined by intracerebroventricular injection. The toxicity of 2 was less than that of KA; however, the mice injected with 2 showed symptoms similar to those induced by KA, while 3-5 did not induce typical symptoms of KA in mice.
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