Fungicidal Sesquiterpene Dialdehyde Cinnamates from Pseudowintera axillaris

Abstract

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.

Antifungal activity of cinnamic acid derivatives involves inhibition of benzoate 4-hydroxylase (CYP53)

“…Cinnamic acid, chlorogenic acid, p-coumaric acid and some other cinnamic acid derivatives were active against several fungal pathogens (Kim et al 2004;Said et al 2004;Brennan et al 2006;Lattanzio et al 2006). Of the numerous structural analogues of cinnamic acid tested, the very promising results were exhibited by (E)-3-(4-methoxy-3-(3-methylbut-2-enyl)phenyl)acrylic acid, which inhibited the fungal growth of A. niger, A. terreus and A. flavus with a similar potency as miconazole (Bisogno et al 2007).…”

Removal Ability and Resistance to Cinnamic and Vanillic Acids by Fungi

“…Cinnamic acid, chlorogenic acid, p-coumaric acid, and some other cinnamic acid derivatives were active against several fungal pathogens [ 26 , 27 , 28 , 29 ]. An analogue of cinnamic acid, (E)-3-(4-methoxy-3(3-methylbut-2-enyl)phenyl) acrylic acid, strongly inhibited the growth of A. niger , A. terreus , and A. flavus , with a similar effect as miconazole [ 30 ].…”

Natural products: a strategic lead generation approach in crop protection discovery

“…Conventional biology has assumed that biodiversity is distributed unevenly, with an abundance of observable species in tropical and marine environments and in natural, as opposed to urban, landscapes. To sample diversity for NP discovery, approximately 90% of the inputs to the DAS NP program over the past 30 years were the result of collaborations with more than 50 private, academic and governmental entities . This third‐party sourcing enabled sampling of biodiversity from a wide range of geographic, environmental and taxonomic sources.…”

“…academic and governmental entities. [39][40][41][42][43][44] This third-party sourcing enabled sampling of biodiversity from a wide range of geographic, environmental and taxonomic sources. Third-party sources for DAS NP discovery over the past 25 years included more than 850 000 NP extracts and more than 2500 pure NPs.…”