Fungicidal sesquiterpene dialdehyde cinnamates from Pseudowintera axillaris.
Bioactivity-directed separation of a foliage extract from the New Zealand shrub Pseudowintera axillaris led to a compound with fungicidal activity against the plant pathogen Phytophthora infestans. This was identified as a new sesquiterpene dialdehyde cinnamate named paxidal. Two 6-hydroxy derivatives were present at lower levels in the extract. A further nine derivatives were synthesized from these natural products for a structure-activity study against a range of important food crop pathogens. The cinnamate group was important for fungicidal effects, and protection of the dialdehyde as a dimethyl acetal gave more potent, broader spectrum activity.
Brennan
Nerida J
NJ
New Zealand Institute for Crop and Food Research Ltd., Department of Chemistry, University of Otago, P.O. Box 56, Dunedin, New Zealand.
Larsen
Lesley
L
Lorimer
Stephen D
SD
Perry
Nigel B
NB
Chapin
Eleanor L
EL
Werk
Todd L
TL
Henry
Matthew J
MJ
Hahn
Donald R
DR
D002934:Cinnamates / Q000032:analysis* / Q000737:chemistry / Q000494:pharmacology; D005659:Fungicides, Industrial / Q000032:analysis* / Q000494:pharmacology; D008958:Models, Molecular; D009520:New Zealand; D010838:Phytophthora / Q000187:drug effects; D010936:Plant Extracts / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry; D032425:Pseudowintera / Q000737:chemistry*; D012717:Sesquiterpenes / Q000032:analysis* / Q000737:chemistry / Q000494:pharmacology
D002934:Cinnamates; D005659:Fungicides, Industrial; D010936:Plant Extracts; D012717:Sesquiterpenes; C508956:paxidal