TY - JOUR
T1 - Isolation of linear peptides related to the hepatotoxins nodularin and microcystins
AU - Choi, Byoung Wook
AU - Namikoshi, Michio
AU - Sun, Furong
AU - Rinehart, Kenneth L.
AU - Carmichael, Wayne W.
AU - Kaup, Anne M.
AU - Evans, William R.
AU - Beasley, Val R.
PY - 1993/12/3
Y1 - 1993/12/3
N2 - 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.
AB - 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.
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U2 - 10.1016/S0040-4039(00)61500-9
DO - 10.1016/S0040-4039(00)61500-9
M3 - Article
AN - SCOPUS:0027485857
VL - 34
SP - 7881
EP - 7884
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 49
ER -