Isolation of linear peptides related to the hepatotoxins nodularin and microcystins

Byoung Wook Choi, Michio Namikoshi, Furong Sun, Kenneth L. Rinehart, Wayne W. Carmichael, Anne M. Kaup, William R. Evans, Val R. Beasley

Research output: Contribution to journalArticlepeer-review

Abstract

Linear peptide 2, Adda-D-Glu(γ)-Mdhb-D-MeAsp(β)-L-Arg-OH, was isolated from cultured Nodularia spumigena and was analyzed in the cells after one week's (1:2 : 30:1) to eight week's (>100:1) cultivation. Three linear peptides, Adda-D-Glu(γ)-Mdha-D-Ala-L-Leu-D-MeAsp(β)-L-Arg-OH (3), L-Leu-D-MeAsp(β)-L-Arg-Adda-D-Glu(γ)-Mdha-D-Ala-OH (4), and L-Phe-D-MeAsp(β)-L-Arg-Adda-D-Glu(γ)-Mdha-D-Ala-OH (5) were obtained from a water bloom of Microcystis spp. collected from Homer Lake (Illinois). Some of these linear peptides (2,3) are thought to be biogenetic precursors of nodularin and microcystins. Linear peptides 2, 3, and 4 did not show apparent toxicity at 1.0, 1.1, and 2.25 mg/kg, respectively, in a mouse bioassay (ip). Feeding experiments using 13C-labeled precursors established that the 2-, 6- and 8-methyl and 9-methoxy carbons of the unusual (2S,3S,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid (Adda) unit of 1 were clearly derived from L-methionine.

Original languageEnglish (US)
Pages (from-to)7881-7884
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number49
DOIs
StatePublished - Dec 3 1993

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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