Six domoic acid related compounds from the red alga, Chondria armata, and domoic acid biosynthesis by the diatom, Pseudo-nitzschia multiseries.

ABSTRACT: Domoic acid (DA, 1), a potent neurotoxin that causes amnesic shellfish poisoning, has been found in diatoms and red algae. While biosynthetic pathway towards DA from geranyl diphosphate and L-glutamate has been previously proposed, its late stage is still unclear. Here, six novel DA related compounds, 7'-methyl-isodomoic acid A (2) and B (3), N-geranyl-L-glutamic acid (4), 7'-hydroxymethyl-isodomoic acid A (5) and B (6), and N-geranyl-3(R)-hydroxy-L-glutamic acid (7), were isolated from the red alga, Chondria armata, and their structures were determined. The compounds 4 and 7, linear compounds, are predictable as the precursors to form the DA pyrrolidine ring. The compounds 2 and 3 are thought as the cyclized products of 7; therefore, dehydration and electron transfer from the internal ole

SUBMITTER: Maeno Y 

PROVIDER: S-EPMC5762911 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature