Isolation, structure determination, and synthesis of neodysiherbaine A, a new excitatory amino acid from a marine sponge

R Sakai; T Koike; M Sasaki; K Shimamoto; C Oiwa; A Yano; K Suzuki; K Tachibana; H Kamiya

doi:10.1021/ol015798l

Isolation, structure determination, and synthesis of neodysiherbaine A, a new excitatory amino acid from a marine sponge

Org Lett. 2001 May 17;3(10):1479-82. doi: 10.1021/ol015798l.

Authors

R Sakai¹, T Koike, M Sasaki, K Shimamoto, C Oiwa, A Yano, K Suzuki, K Tachibana, H Kamiya

Affiliation

¹ School of Fisheries Science, Kitasato University, Sanriku-cho, Iwate 022-0100, Japan.

PMID: 11388846
DOI: 10.1021/ol015798l

Abstract

[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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alanine / analogs & derivatives*
Animals
Bridged Bicyclo Compounds, Heterocyclic
Convulsants / isolation & purification
Convulsants / pharmacology
Dose-Response Relationship, Drug
Epilepsy / chemically induced
Epoxy Compounds / chemical synthesis
Excitatory Amino Acid Agonists / isolation & purification*
Excitatory Amino Acid Agonists / pharmacology
Heterocyclic Compounds, 3-Ring / chemical synthesis
Mice
Molecular Structure
Porifera / chemistry*
Radioligand Assay
Rats
Receptors, Kainic Acid / metabolism
Synaptic Membranes / metabolism

Substances

Bridged Bicyclo Compounds, Heterocyclic
Convulsants
Epoxy Compounds
Excitatory Amino Acid Agonists
Heterocyclic Compounds, 3-Ring
Receptors, Kainic Acid
dysiherbaine
phomactin C
Alanine