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-hexahyd...

Full description

Saved in:
Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2006-01, Vol.69 (1), p.97-102
Main Authors: Broberg, A, Menkis, A, Vasiliauskas, R
Format: Article
Language:English
Subjects:
Actinobacteria - chemistry
Antibiotics (antibacterial agents, antifungal agents)
Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents
Antifungal Agents - chemistry
Antifungal Agents - isolation & purification
Antifungal Agents - pharmacology
antifungal properties
Applied microbiology
Biological and medical sciences
biological control
Ceratobasidium bicorne
chemical structure
depsipeptides
Depsipeptides - chemistry
Depsipeptides - isolation & purification
Depsipeptides - pharmacology
Fundamental and applied biological sciences. Psychology
fungal antagonists
Fungi - drug effects
Fusarium - drug effects
Gibberella avenacea
kutzerides
Kutzneria
Lithuania
Microbiology
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
peptides
Picea - microbiology
Picea abies
plant pathogenic fungi
Plant Roots - microbiology
Pythium - drug effects
Pythium undulatum
root rot
roots
secondary metabolites
seedlings
Seedlings - microbiology
spectral analysis
stereochemistry
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np050378g