Description
Sarmentine: a contact herbicide with broad-spectrum activity.
Sarmentine, 1-(1-pyrrolidinyl)-(2E,4E)-2,4-decadien-1-one, is a natural amide isolated from the fruits of Piper species. It has several biological properties, including antiplasmodial, antimycobacterial, antituberculosis activity, and antiplatelet aggregation. Sarmentine acts as a contact herbicide with broad-spectrum activity similarly to herbicidal soaps, such as nonanoic acid (pelargonic acid) or decanoic acid[1].
Chemical Properties
Light Orange to Brown Low Melting Solid
Uses
Sarmentine is used for controlling plant pests.
Definition
ChEBI: 1-[(2E,4E)-2,4-decadienoyl]pyrrolidine is a N-acylpyrrolidine. It has a role as a metabolite.
Mode of action
In cucumber cotyledon disc assays, sarmentine induced rapid light-independent loss of membrane integrity at 100 μM or higher concentration, whereas 3 mM pelargonic acid was required for a similar effect. Sarmentine was between 10 and 30 times more active than pelargonic acid on wild mustard, velvetleaf, redroot pigweed and crabgrass. Additionally, the potency of 30 μM sarmentine was greatly stimulated by light, suggesting that this natural product may also interfere with photosynthetic processes. Sarmentine also acted as an inhibitor of photosystem II (PSII) on isolated thylakoid membranes by competing for the binding site of plastoquinone. This can be attributed in part to structural similarities between herbicides like sarmentine and diuron. While this mechanism of action accounts for the light stimulation of the activity of sarmentine, it does not account for its ability to destabilize membranes in darkness. In this respect, sarmentine has some structural similarity to crotonoyl-CoA, the substrate of enoyl-ACP reductase, a key enzyme in the early steps of fatty acid synthesis. Inhibitors of this enzyme, such as triclosan, cause rapid loss of membrane integrity in the dark. Sarmentine inhibited the activity of enoyl-ACP reductase, with an I50app of 18.3 μM.
References
[1] Franck E Dayan. “Sarmentine, a natural herbicide from Piper species with multiple herbicide mechanisms of action.” Frontiers in Plant Science (2015): 222.
