Kutznerides 1-4, depsipeptides from the actinomycete Kutzneria sp. 744 inhabiting mycorrhizal roots of Picea abies seedlings.
Bioassay-guided fractionation of culture supernatants of the actinomycete Kutzneria sp. 744 resulted in the isolation of four new depsipeptides (1-4). Structure analysis revealed the general structure: cyclo[2-(1-methylcyclopropyl)-D-glycine-(2S,3aR,8aS)-6,7-dichloro-3a-hydroxy-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid-3-hydroxy-D-glutamic acid-O-methyl-L-serine-L-piperazic acid-(S)-2-hydroxy-3,3-dimethylbutanoic acid]. The 3-hydroxy-d-glutamic acid was present as its threo-isomer in 1 and 2 and as its erythro-isomer in 3 and 4. The piperazic acid was modified to its (R)-4-chloro analogue in 2 and to its C-5/N unsaturated analogue in 4. Compounds 1-4 displayed moderate spore germination inhibiting activity against several common root-rotting fungi.
Broberg
Anders
A
Department of Chemistry, Swedish University of Agricultural Sciences, P.O. Box 7015, SE-750 07 Uppsala, Sweden. Anders.Broberg@kemi.slu.se
Menkis
Audrius
A
Vasiliauskas
Rimvydas
R
D039903:Actinobacteria / Q000737:chemistry*; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects; D005670:Fusarium / Q000187:drug effects; D008097:Lithuania; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D028222:Picea / Q000382:microbiology*; D018517:Plant Roots / Q000382:microbiology; D011775:Pythium / Q000187:drug effects; D036226:Seedlings / Q000382:microbiology
D000935:Antifungal Agents; D047630:Depsipeptides