Isolation, structure determination, and synthesis of neodysiherbaine A, a new excitatory amino acid from a marine sponge.
[structure: see text] A new excitatory amino acid, neodysiherbaine A (2), was isolated as a minor constituent of the aqueous extract from the marine sponge Dysidea herbacea. The structure was deduced by spectroscopic methods and established unambiguously by the total synthesis. The present synthesis, including as a key step cross-coupling of the 6/5-bicyclic core with an amino acid residue, is useful in constructing its structural analogues.
Sakai
R
R
School of Fisheries Science, Kitasato University, Sanriku-cho, Iwate 022-0100, Japan.
Koike
T
T
Sasaki
M
M
Shimamoto
K
K
Oiwa
C
C
Yano
A
A
Suzuki
K
K
Tachibana
K
K
Kamiya
H
H
D000409:Alanine / Q000031:analogs & derivatives*; D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic; D003292:Convulsants / Q000302:isolation & purification / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D004827:Epilepsy / Q000139:chemically induced; D004852:Epoxy Compounds / Q000138:chemical synthesis; D018690:Excitatory Amino Acid Agonists / Q000302:isolation & purification* / Q000494:pharmacology; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis; D051379:Mice; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D011869:Radioligand Assay; D051381:Rats; D018092:Kainic Acid Receptors / Q000378:metabolism; D013570:Synaptic Membranes / Q000378:metabolism
D000409:Alanine; D019086:Bridged Bicyclo Compounds, Heterocyclic; D003292:Convulsants; D004852:Epoxy Compounds; D018690:Excitatory Amino Acid Agonists; D006575:Heterocyclic Compounds, 3-Ring; D018092:Kainic Acid Receptors; C121741:dysiherbaine; C438975:phomactin C