TY - JOUR
T1 - Molecular Markers for Pyrethrin Autoxidation in Stored Pyrethrum Crop: Analysis and Structure Determination
AU - Freemont, Jamie
AU - Littler, Stuart
AU - Hutt, Oliver
AU - Mauger, Stephanie
AU - Meyer, Adam
AU - Winkler, David Alan
AU - Kerr, Maurice
AU - Ryan, John
AU - Cole, Helen
AU - Duggan, Peter
PY - 2016
Y1 - 2016
N2 - Pyrethrum is a natural insecticide extracted from Tanacetum cinerariifolium. Six esters, the pyrethrins, are responsible for the extract's insecticidal activity. The oxidative degradation of pyrethrins through contact with aerial oxygen is a potential cause of pyrethrin losses during pyrethrum manufacture. Described here is the first investigation of the autoxidation chemistry of the six pyrethrin esters isolated from pyrethrum. It was found that pyrethrins I and II, the major pyrethrin esters present in pyrethrum, undergo autoxidation more readily than the minor pyrethrin esters, the jasmolins and cinerins. Chromatographic analysis of pyrethrin I and II autoxidation mixtures showed some correlation with a similar analysis performed on extracts from T. cinerariifolium crop, which had been stored for 12 weeks without added antioxidants. Two pyrethrin II autoxidation products were isolated, characterized, and shown to be present in extracts of stored T. cinerariifolium crop, confirming that autoxidation of pyrethrin esters does occur during crop storage.
AB - Pyrethrum is a natural insecticide extracted from Tanacetum cinerariifolium. Six esters, the pyrethrins, are responsible for the extract's insecticidal activity. The oxidative degradation of pyrethrins through contact with aerial oxygen is a potential cause of pyrethrin losses during pyrethrum manufacture. Described here is the first investigation of the autoxidation chemistry of the six pyrethrin esters isolated from pyrethrum. It was found that pyrethrins I and II, the major pyrethrin esters present in pyrethrum, undergo autoxidation more readily than the minor pyrethrin esters, the jasmolins and cinerins. Chromatographic analysis of pyrethrin I and II autoxidation mixtures showed some correlation with a similar analysis performed on extracts from T. cinerariifolium crop, which had been stored for 12 weeks without added antioxidants. Two pyrethrin II autoxidation products were isolated, characterized, and shown to be present in extracts of stored T. cinerariifolium crop, confirming that autoxidation of pyrethrin esters does occur during crop storage.
U2 - 10.1021/acs.jafc.6b02959
DO - 10.1021/acs.jafc.6b02959
M3 - Article
VL - 64
SP - 7134
EP - 7141
JO - Journal of Agricultural and Food Chemistry
JF - Journal of Agricultural and Food Chemistry
SN - 0021-8561
IS - 38
ER -