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A Novel β‐Amino Acid in Cytotoxic Peptides from the Cyanobacterium Tychonema sp.
Author(s) -
Mehner Christian,
Müller Daniela,
Krick Anja,
Kehraus Stefan,
Löser Reik,
Gütschow Michael,
Maier Armin,
Fiebig HeinzHerbert,
Brun Reto,
König Gabriele M.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200701033
Subject(s) - chemistry , antiprotozoal , clonogenic assay , cytotoxic t cell , amino acid , stereochemistry , cytotoxicity , biochemistry , cell , in vitro
The cyclic dodecapeptides tychonamide A ( 1 ) and B ( 2 ) isolated from the methanolic extract of the cyanobacterium Tychonema sp. contain the novel β‐amino acid 3‐amino‐2,5,7‐trihydroxy‐8‐phenyloctanoic acid (Atpoa). Compounds 1 and 2 have cytotoxic activity towards cancer cell linesin a monolayer assay with mean IC 50 values of 0.9 and 3.3 μg mL –1 , respectively. Compound 2 was shown to be active against tumor cell suspensions derived fromsolid tumor xenografts in a clonogenic assay (mean IC 50 2.4 μg mL –1 ). Additionally, antiprotozoal activity was observed ( Trypanosoma b. rhodesiense , IC 50 0.1 μg mL –1 ) for compound 1 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)